WO2024071216A1 - Pyrazole compound and pest control agent containing same as active ingredient - Google Patents

Pyrazole compound and pest control agent containing same as active ingredient Download PDF

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WO2024071216A1
WO2024071216A1 PCT/JP2023/035193 JP2023035193W WO2024071216A1 WO 2024071216 A1 WO2024071216 A1 WO 2024071216A1 JP 2023035193 W JP2023035193 W JP 2023035193W WO 2024071216 A1 WO2024071216 A1 WO 2024071216A1
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group
substituent
optionally substituted
ylmethyl
ethyl
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PCT/JP2023/035193
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French (fr)
Japanese (ja)
Inventor
英明 生島
駿 岡谷
大貴 林
寛俊 金城
有希 野田
直也 田中
宏貴 石井
愉海 福谷
遼 岡本
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三井化学クロップ＆ライフソリューション株式会社
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Publication of WO2024071216A1 publication Critical patent/WO2024071216A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
    • A01M1/00—Stationary means for catching or killing insects
    • A01M1/20—Poisoning, narcotising, or burning insects
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to pyrazole compounds and their salts, as well as pest control agents or pest arthropod control agents that contain the compounds as active ingredients.
  • Controlling pests plays an extremely important role in ensuring a stable and sustainable supply of agricultural and horticultural crops.
  • a wide variety of pest control agents have been developed and put to practical use.
  • many pests have developed resistance to these existing pesticides due to their long-term use, and damage to agricultural and horticultural crop production remains a serious issue, making it desirable to develop new pesticides that are effective against not only susceptible pests but also resistant pests.
  • pyrazole compounds having a substituted amide group at the 3rd or 5th position of the pyrazole ring are known.
  • azolopyridylpyrazole compounds such as imidazo[1,2-a]pyridine ring and [1,2,4]triazolo[1,5-a]pyridine ring
  • azolopyridylpyrazole compounds having an aromatic amide group have been disclosed as forkhead protein O1 (FOXO1) inhibitors (see, for example, Patent Document 1).
  • the azolopyridylpyrazole compounds described in the specification of Patent Document 1 are limited to compounds having an aromatic amide group.
  • only azolopyridylpyrazole compounds having a 3-chloro-4-methoxybenzamide group as the aromatic amide group are described, and azolopyridylpyrazole compounds having an aliphatic amide group or an oxalic acid amide group are not disclosed at all.
  • the uses of this compound group relate to the pharmaceutical field, which differs from the technical field of pest control agents or pest arthropod control agents according to the present invention.
  • the object of the present invention is to provide compounds that have excellent control effects against harmful organisms or arthropods, mainly in the agricultural field, and intermediates useful for the production of such compounds.
  • the inventors focused on azolopyridylpyrazole compounds and conducted extensive research. As a result, they discovered that a novel group of azolopyridylpyrazole compounds in which an aliphatic amide substituent or the like is introduced at the 3rd or 5th position of the pyrazole ring exhibits excellent control effects against harmful arthropods, which led to the completion of the present invention.
  • the present invention includes the following aspects:
  • R5 is, Cyano group, Halogen atoms, a C1-C6 alkoxy group optionally substituted with a substituent A; C1 to C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted by a substituent A; a C2-
  • a C6 haloalkoxy group a C3-C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group;
  • R2 is, Hydrogen atoms, A C1-C6 alkyl group optionally substituted with a substituent A; C1 to C6 halo
  • R5 is, Cyano group, Halogen atoms, a C1-C6 alkoxy group optionally substituted with a substituent A; C1 to C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted by a substituent A; or Rx4
  • R1 is Hydrogen atoms, A C1-C6 alkyl group optionally substituted with a substituent A; C1 to C6 haloalkyl groups, or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
  • R2 is, Hydrogen atoms, A C1-C6 alkyl group optionally substituted with a substituent A; C1 to C6 haloalkyl groups, or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
  • R3 is, Hydrogen atoms, A C1-C6 alkyl group optionally substituted with a substituent A; C1 to C6 haloalkyl groups, A C3-C8 cycloalkyl group optionally substituted with a substituent A;
  • Rx1Rx2NC( O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyan
  • R1 is represents a C1-C6 alkyl group optionally substituted with a substituent A
  • R2 is, represents a C1-C6 alkyl group optionally substituted with a substituent A
  • R3 is, Hydrogen atoms, A C1-C6 alkyl group optionally substituted with a substituent A
  • R5 is, Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent
  • R1 represents a methyl group or an ethyl group. [5], or a salt thereof.
  • R2 represents a methyl group or an ethyl group.
  • R3 represents a hydrogen atom, a methyl group, an ethyl group, an acetyl group, a cyclopropionyl group, or a methoxycarbonyl group; [0027] The compound or salt thereof according to any one of [1] to [4], [5], and [6].
  • R4 represents a methyl group, an ethyl group, a propyl group, a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a chlorodifluoromethyl group, a dichlorofluoromethyl group, a 1,1-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a heptafluoropropyl group, a nonafluorobutyl group, a cyclopropyl group, a methoxy group, a t-butoxy group, a dimethylcarbamoyl group, a
  • R5 represents an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, an isopropylsulfanyl group, an isopropylsulfinyl group, or an isopropylsulfonyl group; the compound or salt thereof according to any one of [1] to [4] and [5] to [8].
  • R8 represents a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, or a trifluoromethyl group; [0034] The compound or salt thereof according to any one of [1] to [4] and [5] to [12]. [14] [0036] [0037] R9 represents a hydrogen atom, a chlorine atom, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, or a heptafluoropropyl group; [0038] The compound or salt thereof according to any one of [1] to [4] and [5] to [13].
  • [15] The compound or salt thereof according to any one of [1] to [4] and [5] to [14], wherein R10 represents a hydrogen atom.
  • a pest control agent comprising the compound or a salt thereof according to any one of [1] to [4] and [5] to [15] as an active ingredient.
  • the pest control agent according to [16], wherein the pest is an arthropod pest.
  • a method for controlling pests comprising applying the pest control agent according to [16] to a plant, a plant seed, or soil in which a plant is grown. [19] The method for controlling pests according to [18], wherein the pests are arthropod pests.
  • [20] Use of the compound or a salt thereof according to any one of [1] to [4] and [5] to [15] as a pest control agent. [21] The use according to [20], wherein the pest is an arthropod pest. [22] Use of the compound or a salt thereof according to any one of [1] to [4] and [5] to [15] for preparing a pesticide.
  • the present invention provides novel compounds that are effective as pest control agents, particularly as pest control agents for arthropod pests.
  • Cx-Cy means that there are x to y carbon atoms, where x and y are integers, and all integers between x and y are understood to be individually disclosed.
  • C1-C6 means that there are 1, 2, 3, 4, 5, or 6 carbon atoms
  • C2-C6 means that there are 2, 3, 4, 5, or 6 carbon atoms
  • C3-C8 means that there are 3, 4, 5, 6, 7, or 8 carbon atoms
  • C3-C6 means that there are 3, 4, 5, or 6 carbon atoms.
  • Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.
  • the C1 to C6 alkyl group may be linear or branched, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, 1-isopropylpropyl, 1,1,2-trimethylpropyl, and 1,2,2-trimethylpropyl groups.
  • a C1-C6 haloalkyl group refers to the above C1-C6 alkyl group in which the hydrogen atoms are arbitrarily substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents.
  • C1 to C6 haloalkyl group examples include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoro
  • C3 to C8 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.
  • C2-C6 alkenyl groups refer to unsaturated hydrocarbon groups that have one or more double bonds and are linear or branched.
  • geometric isomers they are either the E or Z form alone, or a mixture of the E and Z forms in any ratio, and are not particularly limited as long as they are within the specified carbon number range.
  • C2-C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylallyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 4-methyl-3-pentenyl, and 3-methyl-2-pentenyl.
  • C2-C6 haloalkenyl group refers to the above C2-C6 alkenyl group in which hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents.
  • C2-C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 2,3,3-trifluoroallyl group, 3,3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, and 6,6-difluoro-5-hexenyl group.
  • C2-C6 alkynyl groups refer to unsaturated hydrocarbon groups that have one or more triple bonds and are linear or branched. Specific examples of C2-C6 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1,1-dimethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, and 5-hexynyl.
  • a C2-C6 haloalkynyl group refers to the above C2-C6 alkynyl group in which the hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents.
  • C2 to C6 haloalkynyl groups 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, Examples of such groups include 4-bromo-4,4
  • a C1 to C6 alkoxy group refers to the above-mentioned C1 to C6 alkyl group bonded via an oxygen atom.
  • Specific examples of C1 to C6 alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropyloxy, 1,2-dimethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, 1-isopropylpropyloxy,
  • a C1-C6 haloalkoxy group refers to an alkoxy group having C1-C6 in which the hydrogen atoms are arbitrarily substituted with one or more halogen atoms.
  • the halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents.
  • C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a pentafluoroethoxy group, a 2,2,2-trichloroethoxy group, a 3,3-difluoropropyloxy group, a 3,3,3-trifluoropropyloxy group, a 2,3,3,3-tetrafluoropropyloxy group, a 2,2,3,3,3-pentafluoropropyloxy group, a 1,2,2,3,3,3-hexafluoropropyloxy group, a
  • Examples of such groups include propyloxy, heptafluoropropyloxy, heptafluoroisopropyloxy, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 1,2,2,3,3,4,4,4-octafluorobutoxy, nonafluorobutoxy, nonafluoro-sec-butoxy, 3,3,4,4,5,5,5-heptafluoropentyloxy, 2,3,3,4,4,5,5,5-octafluoropentyloxy, 2,2,3,3,4,4,5,5,5-nonafluoropentyloxy, undecafluoropentyloxy, and tridecafluorohexyloxy.
  • C3-C8 cycloalkoxy groups refer to the above-mentioned C3-C8 cycloalkyl groups bonded via an oxygen atom.
  • Specific examples of C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy groups.
  • 5- to 6-membered aromatic heterocyclic group refers to a cyclic aromatic substituent selected from the group consisting of nitrogen, oxygen, and sulfur atoms, and containing at least one heteroatom as a constituent atom of the ring.
  • Specific examples of 5- to 6-membered aromatic heterocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 5- to 6-membered partially unsaturated heterocyclic group refers to a 5- to 6-membered heterocyclic group in which some bonds are partially saturated, among cyclic aromatic substituents containing at least one heteroatom as a ring constituent atom selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. However, it has one or more unsaturated bonds.
  • 5- to 6-membered partially unsaturated heterocyclic groups include a pyrroline ring group, a pyrazoline ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, an isoxazoline ring group, an oxazine ring group, and a thiooxazine ring group.
  • 8- to 10-membered partially unsaturated heterocyclic group refers to an 8- to 10-membered heterocyclic group in which some bonds are partially saturated, among cyclic aromatic substituents containing at least one heteroatom as a ring constituent atom selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. However, it has one or more unsaturated bonds.
  • 8- to 10-membered partially unsaturated heterocyclic groups include 3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole ring group, 3a,4,5,6,7,7a-hexahydrobenzo[d]isoxazole ring group, and 3a,5,6,7,8,8a-hexahydro-4H-cyclohepta[d]isoxazole ring group.
  • 3- to 6-membered ring groups containing 1 or 2 oxygen atoms include oxiranyl, oxetanyl, oxolanyl, oxanyl, 1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, dihydrofuran-2(3H)-one, and tetrahydro-2H-pyran-2-one.
  • the pyrazole compound of the present invention includes compounds represented by the following formula (1-1) or formula (1-2) and salts thereof.
  • R1 is preferably a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A;
  • R1 is preferably a C1-C6
  • R1 in formula (1-1) includes a hydrogen atom.
  • the C1-C6 alkyl group in the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a pentyl group, and particularly preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or a sec-butyl group.
  • a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent in the description of the substituent A.
  • Preferred examples of the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, a hexyl group, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a 3-cyanopropyl group, a 2-cyanopropan-2-yl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxy
  • chlorophenylmethyl group 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphenylmethyl group, 3-trifluoromethylphenylmethyl group, 4-trifluoromethylphenylmethyl group, 3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 2-methoxyphenylmethyl group , 3-methoxyphenylmethyl group, 4-methoxyphenylmethyl group, 4-phenoxyphenylmethyl group, 4-methanesulfonylphenylmethyl group, 4-trifluoromethylsulfanylphenylmethyl group, 4-trifluorosulfinylphenylmethyl group, 4-trifluorosulfonylpheny
  • C1 to C6 haloalkyl group in R1 of formula (1-1) is defined as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentafluoropropyl group.
  • a difluoromethyl group is preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, and particularly preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, or a 2,2,3,3,4,4,4-heptafluorobutyl group.
  • the C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) is as defined above and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with the substituent A.
  • C1 to C6 cycloalkyl group which may be appropriately substituted with a substituent A" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-(cyclopropane-1-carbonitrile) group, a 2-(cyclopropane-1-carbonitrile) group, a 1-(1-nitrocyclopropyl) group, a 1-(2-nitrocyclopropyl) group, a 1-(1-cyclopropylcyclopropyl) group, a 1-(2-cyclopropylcyclopropyl) group, a 1-(2-methoxycyclopropyl) group, a 1-(2-ethoxycyclopropyl) group, a 1-(1-phenylcyclopropyl) group, a 1-(2-phenylcyclopropyl) group, a 1-(cyclopropylethan-1-one) group,
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) is the same as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
  • the "C2 to C6 haloalkenyl group" in R1 of formula (1-1) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) is as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group.
  • substituent A one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • the "C2 to C6 haloalkynyl group" in R1 of formula (1-1) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
  • the "phenyl group which may be optionally substituted with 0 to 5 substituents B" in R1 of formula (1-1) is a phenyl group in which hydrogen atoms are arbitrarily substituted with 1 to 5 independent substituents B.
  • the "phenyl group which may be optionally substituted with 0 to 5 substituents B" is preferably a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a toluyl group, a methoxyphenyl group, a phenoxyphenyl group, a methylsulfanylphenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, more
  • the 5- to 6-membered aromatic heterocyclic group of "a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" in R1 of formula (1-1) is the same as defined above, and is preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a
  • Preferred examples of the "5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" include a pyridyl group, a 2-cyanopyridyl group, a 3-cyanopyridyl group, a 4-cyanopyridyl group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-iodopyridyl group, a 3-iodopyridyl group, a 4-iodopyridyl group, a 2-methylpyridyl group, a 3-methylpyr
  • Rx4S(O)p- in R1 of formula (1-1) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) has the same meaning as defined above.
  • Rx4S(O)p- is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group, a phenylsulfonyl group, a 4-fluorophenylsulfonyl group, a 4-chlorophenylsulfonyl group, a 4-methylphenylsulfonyl group, or a 4-trifluoromethylphenylsulfonyl group, more preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 4-methylphenylsulfonyl group, or
  • the term "3- to 6-membered ring group containing 1 to 2 oxygen atoms" in R1 of formula (1-1) has the same meaning as above.
  • the "3- to 6-membered ring group containing 1 to 2 oxygen atoms” is preferably an oxiran-2-yl group, an oxetan-3-yl group, a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 1,4-dioxan-2-yl group, a 3-dihydrofuran-2(3H)-one group, a 4-dihydrofuran-2(3H)-one group, a 3-tetrahydro-2H-pyran-2-one group, or a 4-tetra
  • Rx4S(O)p- wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2.
  • R2 is preferably a hydrogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A; Furthermore, R2 is preferably a C1 to C6 alkyl group which may be appropriately substituted with a substituent A.
  • R2 in formula (1-2) includes a hydrogen atom.
  • the C1-C6 alkyl group in the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a pentyl group, and particularly preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or a sec-butyl group.
  • a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent in the description of the substituent A.
  • Preferred examples of the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, a hexyl group, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a 3-cyanopropyl group, a 2-cyanopropan-2-yl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxy
  • chlorophenylmethyl group 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphenylmethyl group, 3-trifluoromethylphenylmethyl group, 4-trifluoromethylphenylmethyl group, 3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 2-methoxyphenylmethyl group , 3-methoxyphenylmethyl group, 4-methoxyphenylmethyl group, 4-phenoxyphenylmethyl group, 4-methanesulfonylphenylmethyl group, 4-trifluoromethylsulfanylphenylmethyl group, 4-trifluorosulfinylphenylmethyl group, 4-trifluorosulfonylpheny
  • C1 to C6 haloalkyl group in R2 of formula (1-2) is defined as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentaethyl group.
  • a difluoromethyl group is preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, and particularly preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, or a 2,2,3,3,4,4,4-heptafluorobutyl group.
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) is as defined above and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
  • C1 to C6 cycloalkyl group which may be appropriately substituted with a substituent A" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-(cyclopropane-1-carbonitrile) group, a 2-(cyclopropane-1-carbonitrile) group, a 1-(1-nitrocyclopropyl) group, a 1-(2-nitrocyclopropyl) group, a 1-(1-cyclopropylcyclopropyl) group, a 1-(2-cyclopropylcyclopropyl) group, a 1-(2-methoxycyclopropyl) group, a 1-(2-ethoxycyclopropyl) group, a 1-(1-phenylcyclopropyl) group, a 1-(2-phenylcyclopropyl) group, a 1-(cyclopropylethan-1-one) group,
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) is the same as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
  • C2-C6 haloalkenyl group in R2 of formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) is as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group.
  • substituent A one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • the "C2 to C6 haloalkynyl group" in R2 of formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
  • the "phenyl group which may be optionally substituted with 0 to 5 substituents B" in R2 of formula (1-2) is a phenyl group in which hydrogen atoms are arbitrarily substituted with 1 to 5 independent substituents B.
  • the "phenyl group which may be optionally substituted with 0 to 5 substituents B" is preferably a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a toluyl group, a methoxyphenyl group, a phenoxyphenyl group, a methylsulfanylphenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, more
  • the 5- to 6-membered aromatic heterocyclic group of "a 5- to 6-membered aromatic heterocyclic group which may be appropriately substituted with 0 to 4 substituents B" in R2 of formula (1-2) is the same as defined above, and is preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thi
  • Preferred examples of the "5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" include a pyridyl group, a 2-cyanopyridyl group, a 3-cyanopyridyl group, a 4-cyanopyridyl group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-iodopyridyl group, a 3-iodopyridyl group, a 4-iodopyridyl group, a 2-methylpyridyl group, a 3-methylpyr
  • Rx4S(O)p- represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) has the same meaning as defined above.
  • Rx4S(O)p- is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group, a phenylsulfonyl group, a 4-fluorophenylsulfonyl group, a 4-chlorophenylsulfonyl group, a 4-methylphenylsulfonyl group, or a 4-trifluoromethylphenylsulfonyl group, more preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 4-methylphenylsulfonyl group, or
  • the term "3- to 6-membered ring group containing 1 to 2 oxygen atoms" in R2 of formula (1-2) has the same meaning as above.
  • the "3- to 6-membered ring group containing 1 to 2 oxygen atoms" is preferably an oxiran-2-yl group, an oxetan-3-yl group, a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 1,4-dioxan-2-yl group, a 3-dihydrofuran-2(3H)-one group, a 4-dihydrofuran-2(3H)-one group, a 3-tetrahydro-2H-pyran-2-one group, or a 4-tetra
  • R3 in formula (1-1) or formula (1-2) includes a hydrogen atom.
  • the C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with the substituent A" in R3 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethyl butyl
  • C1 to C6 haloalkyl group in R3 of formula (1-1) or formula (1-2) is defined as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, and particularly preferably a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R3 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and particularly preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with a substituent as described for the substituent A.
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R3 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
  • the "C2 to C6 haloalkenyl group" in R3 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R3 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group.
  • substituent A one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • the "C2 to C6 haloalkynyl group" in R3 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propyn
  • phosphoruscarbonyl group dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocanecarbonyl group, dimethylcarbamoyl group, ethylmethylcarbamoyl group, diethylcarbamoyl group, methylpropylcarbamoyl group, ethylpropylcarbamoyl group, isopropylmethylcarbamoyl group, isopropylethylcarbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, butylethylcarbamoyl group, sec -butylmethylcarbamoyl group, sec-butylethylcarbamoyl group, isobutylmethylcarbamoyl group, isobutylethylcarbamoyl group, t-butylmethylcar
  • Examples of the above-listed groups include (propyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)
  • bromoacetyl group 2,2,2-trifluoroacetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2,2-trichloroacetyl group, 2,2,3,3-tetrafluoropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoropropionyl group, 2,2,3,3,4,4-hexafluorobutyryl group, 2,2,3,3,4,4,4-heptafluorobutyryl group, 2,2,3 ,3,4,4,5,5-octafluoropentanoyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl group, 2,2,3,3,4,4,5,5,6,6-decafluorohexanoyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, cyclopropion
  • a 5- to 6-membered partially unsaturated heterocyclic group or an 8- to 10-membered partially unsaturated heterocyclic group
  • the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent, or may be the same to form a 3- to 6-membered ring)] is preferred,
  • R4 in formula (1-1) or formula (1-2) includes a hydrogen atom.
  • the C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with the substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl
  • the "C1 to C6 haloalkyl group" in R4 of formula (1-1) or formula (1-2) has the same meaning as defined above, and is preferably a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-tri ...
  • a fluoroethyl group a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 2,3,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, ethyl group, 2,2,3,3,4,4,4-h
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, even more preferably a cyclopropyl group or a cyclohexyl group, and particularly preferably a cyclopropyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with a substituent
  • the C1 to C6 alkoxy group in the "C1 to C6 alkoxy group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, or a t-butoxy group, more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a t-butoxy group, and particularly preferably a methoxy group or a t-butoxy group.
  • the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with a substituent as described for the substituent A.
  • the "C1 to C6 haloalkoxy group" in R4 of formula (1-1) or formula (1-2) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a trifluoromethoxy group or a 1,1,2,2,2-pentafluoroethoxy group.
  • the C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
  • the "C2 to C6 haloalkenyl group" in R4 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group.
  • substituent A one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • the "C2 to C6 haloalkynyl group" in R4 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propyn
  • a propyloxymethylcarbamoyl group an isopropyloxymethylcarbamoyl group, a 2-methoxyethylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a cyanomethylcarbamoyl group, a 1-cyanoethylcarbamoyl group, a 2-cyanoethylcarbamoyl group, a cyclopropylmethylcarbamoyl group, a cyclobutylmethylcarbamoyl group, a benzylcarbamoyl group, a 1-phenethylcarbamoyl group, a 1-difluoroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group, a 2,2,2-trifluoroethyl carbamoyl group, 2,2,3,3,3-pentafluoropropyl
  • methylpropylcarbamoyl group isopropylmethylcarbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, isobutylmethylcarbamoyl group, methylpentylcarbamoyl group, (neopentyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, methyl(2,2-difluoroethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (methoxy)methylcarbamoyl group, Particularly preferred is a dimethylcarbamoyl group or a diethylcarbamoyl group.
  • 2-(1H-1,2,4-triazol-1-yl)acetyl group 2-chloroacetyl group, 2,2-difluoroacetyl group, 2,2-dichloroacetyl group, 2,2-dibromoacetyl group, 2,2,2-trifluoroacetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2,2-trichloroacetyl group, 2,2,3,3-tetrafluoropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoroacetyl group, fluoropropionyl group, 2,2,3,3,4,4-hexafluorobutyryl group, 2,2,3,3,4,4,4-heptafluorobutyryl group, 2,2,3,3,4,4,5,5-octafluoropentanoyl group, 2,2,3,3,4,4,5,5,5
  • each term in the "5- to 6-membered partially unsaturated heterocyclic group, or 8- to 10-membered partially unsaturated heterocyclic group" in R4 of formula (1-1) or formula (1-2) [the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring)] has the same meaning as defined above.
  • the "5- to 6-membered partially unsaturated heterocyclic group or 8- to 10-membered partially unsaturated heterocyclic group” is preferably a pyrroline ring group, a pyrazoline ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, an isoxazoline ring group, an oxazine ring group, or a thiooxazine ring group, and the pyrroline ring group, the pyrazoline ring group, the imidazoline ring group, the oxazoline ring group, the thiazoline ring group, the isoxazoline ring group, the oxazine ring group, or the thiooxazine ring group is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent independent substituents or may be the same to form a
  • an oxazoline ring group or an isoxazoline ring group and the oxazoline ring group or the isoxazoline ring group is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring.)
  • substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring.
  • the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring.
  • the isoxazoline ring group in the "5- to 6-membered partially unsaturated heterocyclic group or 8- to 10-membered partially unsaturated heterocyclic group” is preferably a structure represented by formula (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), or (4-7) shown in [Chemical Formula 7] (wherein, in the formula, the substituent B is absent or, if present, has the same meaning as above). More preferably, it is a structural formula shown in [Chemical Formula 8], Particularly preferred is the structural formula shown in [Chemical Formula 9].
  • R5 in formula (1-1) or formula (1-2) is a cyano group, a halogen atom, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or Rx4S(O)p- (where Rx4 is hydrogen).
  • R5 is preferably a cyano group, a halogen atom, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A, or Rx4S(O)p- (where Rx4 and p are as defined above),
  • R5 is preferably a cyano group, a halogen atom, a C1-C6 alkoxy group optionally substituted with a substituent A, or Rx4S(O)p- (where Rx4 and p are as defined above),
  • R5 is preferably Rx4S(O)p- (wherein Rx4 and p are as defined above).
  • R5 in formula (1-1) or formula (1-2) includes a cyano group.
  • the halogen atom in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom or a chlorine atom.
  • the C1 to C6 alkoxy group in the "C1 to C6 alkoxy group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) is the same as defined above, and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, or a t-butoxy group, more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a t-butoxy group, and particularly preferably a methoxy group or an ethoxy group.
  • the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with a substituent as described for the substituent A.
  • the "C1 to C6 haloalkoxy group" in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, or a 1,1,2,2,2-pentaflu
  • the C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
  • the "C2 to C6 haloalkenyl group" in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group.
  • substituent A one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • the "C2 to C6 haloalkynyl group" in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propyn
  • Rx4S(O)p- represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above.
  • a phenyl group which may be optionally substituted with 0 to 5 substituents B when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B.
  • Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group.
  • Rx4S(O)p- examples include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, an isopropylsulfanyl group, an isopropylsulfinyl group, an isopropylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulf
  • Sulfonyl group isopropylsulfanyl group, isopropylsulfinyl group, isopropylsulfonyl group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyclopropylsulfanyl group, cyclopropylsulfinyl group, or cyclopropylsulfonyl group, and particularly preferably ethylsulfanyl group, ethylsulfinyl group, ethylsulfonyl group, propylsulfanyl group, propylsulfinyl group, propylsulfonyl group, isopropylsulfanyl group, isopropylsulfinyl group, or isopropylsulfonyl group.
  • Het represents the formula (Het); G in the formula (Het) represents C-R6 or a nitrogen atom.
  • R6 in formula (Het) represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group.
  • R6 is preferably a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A;
  • R6 is preferably a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent A;
  • R6 is preferably a hydrogen atom.
  • R6 in formula (Het) includes a hydrogen atom and a cyano group.
  • halogen atom in R6 of formula (Het) is defined as above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a chlorine atom or a bromine atom.
  • the C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, or a 1,1-dimethylbutyl group.
  • substituent A one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
  • C1-C6 haloalkyl group in R6 of formula (Het) is the same as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a dibromomethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, or a 2,2,3,3,3-pentafluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, or a 2,2,3,3,3-pentafluoropropyl group, and particularly preferably a difluoromethyl group, a trifluoromethyl group
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) is the same as defined above, and is preferably a vinyl group, a 1-propenyl group, or an allyl group, more preferably a vinyl group or an allyl group, and particularly preferably an allyl group.
  • a substituent A one hydrogen atom in the C2-C6 alkenyl group is substituted with the substituent A.
  • C2-C6 haloalkenyl group in R6 of formula (Het) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) has the same definition as above, and is preferably an ethynyl group, a 1-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, and particularly preferably an ethynyl group or a propargyl group.
  • substituent A one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • C2-C6 haloalkynyl group in R6 of formula (Het) is defined as above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group, more preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group,
  • R7 in formula (Het) represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group.
  • R7 is preferably a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A;
  • R7 is preferably a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent A;
  • R7 is preferably a hydrogen atom.
  • R7 in formula (Het) includes a hydrogen atom and a cyano group.
  • the halogen atom in R7 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom or a chlorine atom.
  • the C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, or a 1,1-dimethylbutyl group.
  • substituent A one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
  • C1-C6 haloalkyl group in R7 of formula (Het) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-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 a 2,2,2-trifluoroethyl group, and particularly preferably a difluoromethyl group or a trifluoromethyl group.
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
  • the C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) is as defined above, and is preferably a vinyl group, a 1-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, and particularly preferably a vinyl group or an allyl group.
  • substituent A one hydrogen atom in the C2-C6 alkenyl group is substituted with the substituent A.
  • C2-C6 haloalkenyl group in R7 of formula (Het) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, more preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, and particularly preferably a 2,2-difluorovinyl group or a 3,3-difluoroallyl group.
  • the C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, or a propargyl group, and particularly preferably an ethynyl group.
  • the C2-C6 alkynyl group has a substituent described for the substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
  • the "C2-C6 haloalkynyl group" in R7 of formula (Het) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
  • R8 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1-C6 alkoxy group which may be optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom , a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8
  • R8 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
  • R8 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above)
  • R8 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl
  • R8 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
  • the halogen atom in R8 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a chlorine atom, a bromine atom, or an iodine atom.
  • the C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R8 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethyl butyl group, 1,
  • C1-C6 haloalkyl group in R8 of formula (Het) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a penta
  • a 2-chloro-1,1,2,2-tetrafluoroethyl group a 2-fluoropropyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3,3,3-trichloropropyl group, a 2,3,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 1,1,1,3,3,3-hexafluoro-2-methylpropyl group, a 1,1,1-trifluoro-2-methylpropyl group, a 2-fluoroisopropyl group, and a heptafluoroisopropyl group, More preferred are a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloro
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R8 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
  • the C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be appropriately substituted with a substituent A" in R8 of formula (Het) is the same as defined above, and is 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 or an ethoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with a substituent as described for the substituent A.
  • the "C1-C6 haloalkoxy group" in R8 of formula (Het) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a trifluoromethoxy group or a 1,1,2,2,2-pentafluoroethoxy group.
  • the C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R8 of formula (Het) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
  • Rx4S(O)p- represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above.
  • a phenyl group which may be optionally substituted with 0 to 5 substituents B when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B.
  • Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group.
  • Rx4S(O)p- examples include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfanyl group, a cyclopropylsulfinyl group, a cyclopropylsulfonyl group, a
  • R9 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1-C6 alkoxy group which may be optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom , a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8
  • R9 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
  • R9 is preferably a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above)
  • R9 is preferably a hydrogen atom, a halogen atom, or a C1-C6 haloalkyl group.
  • R9 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
  • the halogen atom in R9 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, even more preferably a fluorine atom or a chlorine atom, and particularly preferably a chlorine atom.
  • the C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R9 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethyl butyl group, 1,
  • C1-C6 haloalkyl group in R9 of formula (Het) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a penta
  • a 2-chloro-1,1,2,2-tetrafluoroethyl group a 2-fluoropropyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3,3,3-trichloropropyl group, a 2,3,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 1,1,1,3,3,3-hexafluoro-2-methylpropyl group, a 1,1,1-trifluoro-2-methylpropyl group, a 2-fluoroisopropyl group, and a heptafluoroisopropyl group, More preferred are a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloro
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R9 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
  • the C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be appropriately substituted with a substituent A" in R9 of formula (Het) is the same as defined above, and is 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 or an ethoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is substituted with the substituent A.
  • the "C1-C6 haloalkoxy group" in R9 of formula (Het) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a difluoromethoxy group or a trifluoromethoxy group.
  • the C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R9 of formula (Het) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
  • Rx4S(O)p- in R9 of formula (Het) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above.
  • a phenyl group which may be optionally substituted with 0 to 5 substituents B when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B.
  • Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group.
  • Rx4S(O)p- examples include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfanyl group, a cyclopropylsulfinyl group, a cyclopropylsulfonyl group, a
  • R10 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1-C6 alkoxy group which may be optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom , a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8
  • R10 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
  • R10 is preferably a hydrogen atom, a halogen atom, or a C1-C6 haloalkyl group.
  • R10 is preferably a hydrogen atom.
  • R10 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
  • the halogen atom in R10 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom or a chlorine atom.
  • the C1-C6 alkyl group in the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" in R10 of formula (Het) has the same definition as above, and is 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, or an isopropyl group, and particularly preferably a methyl group or an ethyl group.
  • substituent A one hydrogen atom in the C1-C6 alkyl group is substituted with the substituent A.
  • C1-C6 haloalkyl group in R10 of formula (Het) is the same as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group, and particularly preferably a difluoromethyl group, a trifluoromethyl group, a 1,1,2,2,2-pentafluoro
  • the C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R10 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
  • the C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be appropriately substituted with a substituent A" in R10 of formula (Het) is as defined above, and is 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 or an ethoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is substituted with the substituent A.
  • the "C1-C6 haloalkoxy group" in R10 of formula (Het) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a difluoromethoxy group or a trifluoromethoxy group.
  • the C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R10 of formula (Het) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group.
  • substituent A one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
  • Rx4S(O)p- in R10 of formula (Het) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above.
  • a phenyl group which may be optionally substituted with 0 to 5 substituents B when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B.
  • Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group.
  • Rx4S(O)p- examples include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfanyl group, a cyclopropylsulfinyl group, a cyclopropylsulfonyl group, a
  • Substituent A is selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group optionally substituted with 0-5 substituents C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents C, and a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.
  • substituted A is selected from the group consisting of a cyano group, a halogen atom, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a phenyl group optionally substituted with 0-5 substituents C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents C, and a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.
  • substituted A is selected from the group consisting of a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a phenyl group optionally substituted with 0-5 substituents C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents C, and a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.
  • substituted A include a hydroxyl group, a cyano group, a nitro group, Halogen atoms include fluorine, chlorine, bromine, and iodine atoms; C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group; C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropyloxy group, and a 2,2,3,3,3-pentafluoropropyl
  • substituted A include a cyano group
  • Halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms
  • C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group
  • C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group
  • C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropyloxy group, and a 2,2,3,3,3-pentafluoropropyloxy group
  • Examples of the phenyl group which may be optional
  • substituted alkoxy groups include methoxy and ethoxy groups
  • phenyl groups which may be optionally substituted with 0 to 5 substituents C include a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a dichlorophenyl group, a toluyl group, a trifluoromethylphenyl group, a cyclopropylphenyl group, a methoxyphenyl group, a trifluoromethoxyphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, and a trifluoromethylsulfonylphenyl group; Examples of the 5- to 6-membered
  • Substituent B is selected from the group consisting of hydroxyl, cyano, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, and Rx5S(O)p- (wherein Rx5 represents hydroxyl, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, or C2-C6 haloalkynyl, and p represents an integer of 0, 1, or 2).
  • substituted B is selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, and Rx5S(O)p- (wherein Rx5 and p are as defined above).
  • substituted B is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and Rx5S(O)p- (wherein Rx5 and p are as defined above).
  • substituted alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, and hexyl;
  • C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, dibromomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,2,2,2-tetrafluoroethyl, pentafluor
  • substituted B include a hydroxyl group; a cyano group;
  • Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
  • C1 to C6 alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group;
  • C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, and a heptafluoropropyl group;
  • a C3 to C8 cycloalkyl group a cycloalky
  • substituted B include a cyano group
  • Halogen atoms include fluorine, chlorine, bromine, and iodine atoms
  • C1-C6 alkyl groups include a methyl group, an ethyl group, a propyl group, and an isopropyl group
  • C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group
  • C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, and a propyloxy group
  • Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and
  • Substituent C is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, and Rx5S(O)p- (wherein Rx5 and p are as defined above).
  • substituted C is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group.
  • substituted C is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, and a C1-C6 alkoxy group.
  • substituted C include a cyano group
  • Halogen atoms include fluorine, chlorine, bromine, and iodine atoms
  • C1-C6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, and hexyl
  • C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, dibromomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,2,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2,3,3,3-pent
  • substituted C include a cyano group
  • Halogen atoms include fluorine, chlorine, bromine, and iodine atoms
  • C1 to C6 alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group
  • C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, and a heptafluoropropyl group
  • As a C3 to C8 cycloalkyl group a cyclopropyl group
  • substituted C include a cyano group
  • Halogen atoms include fluorine, chlorine, bromine, and iodine atoms
  • C1-C6 alkyl groups include a methyl group, an ethyl group, a propyl group, and an isopropyl group
  • C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group
  • C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, and a propyloxy group
  • Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and
  • the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain one or more asymmetric atoms.
  • the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
  • the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may have one or two axial chiralities.
  • the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
  • the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain geometric isomers.
  • the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
  • the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain rotational isomers.
  • the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
  • the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may be capable of forming salts.
  • Examples include, but are not limited to, acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium. Salts that can be used as agricultural and horticultural pest control agents are preferred.
  • Specific compounds of the present invention are those having structural formulas C-1 to C-168 shown in Table 1 (wherein the bond position cut by the wavy line represents the bond position of Het in Table 2), structural formulas Pyra-1 to Pyra-48 shown in Table 2 (wherein R1, R2, R3, R4, Het, and p in Table 2 are as defined above), and substituents R1-1 to R1-203, R1-500 to R1-1315 showing R1 (wherein R1 is as defined above) shown in Table 3 (wherein the bond position cut by the wavy line in the structural formulas in Table 3 represents the bond position of Het in Table 2).
  • 2-F-Ph means a phenyl group with a fluorine atom bonded to the 2-position
  • 2-N ⁇ C-Ph means a phenyl group with a cyano group bonded to the 2-position
  • 2-Py represents a pyridin-2-yl group
  • 3-Py represents a pyridin-3-yl group
  • 4-Py represents a pyridin-4-yl group
  • 1-Pyra represents a 1H-pyrazol-1-yl group
  • 1-Tria represents a 1H-triazol-1-yl group
  • Rk is R1 or R2, and R1 and R2 are a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, Rx1Rx2NC ( ⁇ O)-(wherein Rx1 and Rx2 are each independently
  • Rx4S(O)p- where Rx4 and p are as defined above
  • Ra is a hydrogen atom, or a C1-C6 alkyl group optionally substituted with substituent A.
  • Production method A is a method for obtaining compounds represented by formula (3-1) and formula (3-2) including production intermediates of the compound of the present invention, and comprises reacting a compound represented by formula (2) with Rk- NHNH2 in a solvent.
  • the compound represented by formula (3-1) and the compound represented by formula (3-2) may be either alone or in any mixture in any ratio, and there is no particular limitation on their ratio.
  • Rk-NHNH 2 used in this reaction can be obtained as a commercial product or produced by a known method.
  • Rk-NHNH 2 may be a salt formed with an acidic compound such as hydrochloric acid or hydrobromic acid, and is not particularly limited as long as the desired reaction proceeds.
  • the amount of Rk- NHNH2 used in this reaction may be 1 equivalent or more relative to the compound represented by formula (2), and is not particularly limited as long as the intended reaction proceeds, but is preferably 1 equivalent or more and 20 equivalents or less.
  • This reaction can be carried out in the presence of an acid.
  • the acid to be used include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and p-toluenesulfonic acid.
  • inorganic acids such as hydrochloric acid and sulfuric acid
  • organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and p-toluenesulfonic acid.
  • acetic acid or trifluoroacetic acid is preferred.
  • the use of an acid is not essential.
  • the amount of acid used in this reaction may be at least 1 equivalent relative to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 50 equivalents.
  • the acid used is liquid, it can also be used as a solvent.
  • a solvent can be used in this reaction, but is not essential.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol, isopropanol, and trifluoroethanol, 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, and N,N-dimethylacetamide, ure
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (2).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained above can be subjected to solvent distillation under reduced pressure as long as the compounds do not decompose.
  • the reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. After purification, the compounds of formula (3-1) and formula (3-2) may be separated, which may be set appropriately depending on the desired purity.
  • Production method B is a method for obtaining a compound represented by formula (3-3), which includes a production intermediate of the compound of the present invention, and includes reacting a compound represented by formula (3-2) with Rb-Lv in a solvent in the presence of a base.
  • Rb-Lv used in this reaction can be obtained commercially or produced by a known method.
  • Rb-Lv may be an acid anhydride.
  • the amount of Rb-Lv used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3-2), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • bases examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[2.2.2]octane, and dimethylaminopyridine; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbon
  • the amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3-2), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloro
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-2).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
  • a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (3-3) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-3) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-3) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Rc represents a halogen atom
  • HalR represents a halogenating agent
  • R2, Ra, and Rb are as defined above.
  • Production method C is a method for obtaining a compound represented by formula (3-4) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-3) with a halogenating agent (HalR) in a solvent.
  • Rc represents a halogen atom
  • HalR halogenating agent
  • Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, chlorine, bromine, iodine, etc.
  • the amount of halogenating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-3) as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.
  • the amount of halogenating agent containing hydantoin is not particularly limited as long as it is at least 0.5 equivalents as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 5 equivalents or less.
  • acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid can be added.
  • the amount of acid used in this reaction is not particularly limited as long as it is 0.01 equivalents or more relative to the compound represented by formula (3-3) and the desired reaction proceeds, but is preferably 0.1 equivalents or more and 3 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; ether solvents such as diethyl ether, 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, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-di
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-3).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (3-4) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-4) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-4) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • R5a represents a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A
  • Q represents an oxygen atom or a sulfur atom
  • R2, Ra, Rb, and Rc are as defined above.
  • Production method D is a method for synthesizing a compound represented by formula (3-5), which comprises reacting a compound represented by formula (3-4) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
  • Rc is preferably a chlorine atom, a bromine atom, or an iodine atom, more preferably a bromine atom or an iodine atom, and particularly preferably an iodine atom.
  • R5a-QH (wherein R5a and Q have the same meanings as defined above) used in this reaction is commercially available or can be prepared by a known method.
  • R5a-OH is preferably methanol, ethanol, propanol, isopropanol, 2,2,2-trifluoroethanol, or 2,2,3,3,3-pentafluoropropanol, and more preferably methanol, ethanol, or 2,2,2-trifluoroethanol.
  • R5a-SH is preferably methyl mercaptan, ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, or butyl mercaptan, more preferably methyl mercaptan, ethyl mercaptan, or isopropyl mercaptan, and particularly preferably ethyl mercaptan.
  • the amount of R5a-QH used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-4) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 20 equivalents.
  • This reaction can be carried out by a coupling reaction using transition metals.
  • the transition metals used in this reaction may have a ligand, and include palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)palladium dichloride.
  • the amount of transition metals used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (3-4), but is not particularly limited as long as the desired reaction proceeds.
  • phosphine ligands such as triphenylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, 2-di-t-butylphosphino-2'4'6'-triisopropylbiphenyl, and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene can be added.
  • triphenylphosphine 1,1'-bis(diphenylphosphino)ferrocene
  • 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl 2-di-t-butylphosphino-2'4'6'-triisopropylbiphenyl
  • 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene can be
  • the amount of phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (3-4), but is not particularly limited as long as the desired reaction proceeds.
  • the bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate, and organic bases such as triethylamine, tributylamine, and diisopropylethylamine.
  • the amount of base used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-4) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 50 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include alcohol solvents such as methanol, ethanol, and t-butyl alcohol; ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in a mixture of two or more in any ratio.
  • alcohol solvents such as methanol, ethanol, and t-butyl alcohol
  • ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane
  • benzene solvents such as
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-4).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 30°C and 180°C or below the boiling point of the solvent.
  • a separation operation by adding water or a suitable aqueous solution to the reaction mixture.
  • an aqueous solution it is possible to arbitrarily use an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary.
  • a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene
  • an ester-based solvent such
  • these solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield. In addition, it is possible to remove insoluble matter by performing a filtration operation, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-5) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-5) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-5) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Rd represents a C1-C6 alkyl group which may be appropriately substituted with a substituent A
  • R2, R5a, Q, and Rb are as defined above.
  • Production method E is a method for synthesizing a compound represented by formula (3-6), which includes reacting a compound represented by formula (3-5) in a solvent under acidic or basic conditions.
  • the acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, etc., or organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. There are no particular limitations as long as the desired reaction proceeds.
  • the amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more relative to the compound represented by formula (3-5).
  • liquid acids can also be used as a solvent.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, 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, and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-5).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
  • 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 desired reaction proceeds.
  • the amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-5), but is preferably 1 equivalent or more and 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and the like, alcohol solvents such as methanol, ethanol, isopropanol, and the like, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, and the like, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-5).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
  • Reactions under acidic and basic conditions can be treated by the same method after the reaction.
  • a 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, or saline solution can be used as desired.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary.
  • solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired
  • reaction mixture containing the compound represented by formula (3-6) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-6) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-6) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • r represents an integer of 1 or 2
  • Ox represents an oxidizing agent
  • R2, R5a, Ra, and Rb are as defined above.
  • Production method F is a method for obtaining a compound represented by formula (3-7), which includes reacting a compound represented by formula (3-6a) with an oxidizing agent (Ox) in a solvent.
  • the oxidizing agent used in this reaction includes peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid. Transition metals such as sodium tungstate can also be added.
  • the amount of oxidizing agent used in this reaction is usually 1.0 equivalent or more and less than 1.2 equivalents relative to the compound represented by formula (3-6a) when producing a compound represented by formula (3-7) where r is an integer of 1, and usually 2 equivalents or more and 10 equivalents or less when producing a compound represented by formula (3-7) where r is an integer of 2.
  • the amount of transition metal added is usually 0.001 equivalent or more and 1 equivalent or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water solvents, acidic solvents such as acetic acid, benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, nitrile-based solvents such as acetonitrile, and halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-6a).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 120°C, or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (3-7) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-7) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-7) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Rd represents a C1-C6 alkyl group which may be appropriately substituted with a substituent A
  • R2, R5a, Rb, and r are as defined above.
  • Production method G is a method for synthesizing a compound represented by formula (3-8), which includes reacting a compound represented by formula (3-7) in a solvent under acidic or basic conditions.
  • the acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, etc., or organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. There are no particular limitations as long as the desired reaction proceeds.
  • the amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more relative to the compound represented by formula (3-7).
  • liquid acids can also be used as a solvent.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, 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, and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-7).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
  • 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 desired reaction proceeds.
  • the amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-7), but is preferably 1 equivalent or more and 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and the like, alcohol solvents such as methanol, ethanol, isopropanol, and the like, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, and the like, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-7).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
  • Reactions under acidic and basic conditions can be treated by the same method after the reaction.
  • a 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, or saline solution can be used as desired.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary.
  • solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired
  • reaction mixture containing the compound represented by formula (3-8) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-8) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-8) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Ra, R1, Rb, and Lv are as defined above.
  • Production method H is a method for obtaining a compound represented by formula (3-9), which includes a production intermediate of the compound of the present invention, and includes reacting a compound represented by formula (3-1) with Rb-Lv in a solvent in the presence of a base.
  • manufacturing method H By using the compound represented by formula (3-2) in place of the compound represented by formula (3-1) in manufacturing method B, manufacturing method H can be carried out in accordance with manufacturing method B.
  • Production method I is a method for obtaining a compound represented by formula (3-10) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-9) with a halogenating agent (HalR) in a solvent.
  • a halogenating agent HalR
  • production method I By using the compound represented by formula (3-3) in place of the compound represented by formula (3-9) in production method C, production method I can be carried out in accordance with production method C.
  • Production method J is a method for synthesizing a compound represented by formula (3-11), which comprises reacting a compound represented by formula (3-10) with R5a-QH (wherein R5a and Q are as defined above) in a solvent in the presence of a base.
  • production method J By replacing the compound represented by formula (3-4) in production method D with the compound represented by formula (3-10), production method J can be carried out in accordance with production method D.
  • Production method K is a method for synthesizing a compound represented by formula (3-13), which includes reacting a compound represented by formula (3-12) in a solvent under acidic or basic conditions.
  • manufacturing method K By replacing the compound represented by formula (3-5) in manufacturing method E with the compound represented by formula (3-12), manufacturing method K can be carried out in accordance with manufacturing method E.
  • R1, R5a, Ra, Rb, r, and Ox are as defined above.
  • Production method L is a method for obtaining a compound represented by formula (3-14), which includes reacting a compound represented by formula (3-6b) with an oxidizing agent (Ox) in a solvent.
  • production method L By using the compound represented by formula (3-6a) in place of the compound represented by formula (3-6b) in production method F, production method L can be carried out in accordance with production method F.
  • R1, R5a, Rb, Rd, and r are as defined above.
  • Production method M is a method for synthesizing a compound represented by formula (3-16), which includes reacting a compound represented by formula (3-15) in a solvent under acidic or basic conditions.
  • manufacturing method M can be carried out in accordance with manufacturing method G.
  • R6 represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group, and R2, Rc, Rd, and HalR are as defined above.
  • Production method N is a method for obtaining a compound represented by formula (3-18) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-17) with a halogenating agent (HalR) in a solvent.
  • Rc represents a halogen atom
  • manufacturing method N By replacing the compound represented by formula (3-3) in manufacturing method C with the compound represented by formula (3-17), manufacturing method N can be carried out in accordance with manufacturing method C.
  • Re represents a halogen atom
  • HalR represents a halogenating agent
  • R2, R6, Rc, and Rd are as defined above.
  • Production method O is a method for obtaining a compound represented by formula (3-19) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-18) with a halogenating agent (HalR) in a solvent.
  • Re represents a halogen atom
  • Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine, trimethylphenylammonium tribromide, benzyltrimethylammonium tribromide, etc.
  • the amount of halogenating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-18) as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less.
  • the amount of halogenating agent containing hydantoin is not particularly limited as long as it is at least 0.5 equivalents as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 5 equivalents or less.
  • acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid can be added.
  • the amount of acid used in this reaction is not particularly limited as long as it is 0.01 equivalents or more relative to the compound represented by formula (3-18) and the desired reaction proceeds, but is preferably 0.1 equivalents or more and 3 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; ether solvents such as diethyl ether, 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, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-di
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-18).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
  • the reaction mixture containing the compound represented by formula (3-19) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (3-19) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (3-19) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Production method P is a method for synthesizing a compound represented by formula (3-20), which comprises reacting a compound represented by formula (3-18) with R5a-QH (wherein R5a and Q are as defined above) in a solvent in the presence of a base.
  • manufacturing method P By replacing the compound represented by formula (3-4) in manufacturing method D with the compound represented by formula (3-18), manufacturing method P can be carried out in accordance with manufacturing method D.
  • HalR represents a halogenating agent
  • R2, R5a, Q, R6, Rd and Re are as defined above.
  • Production method Q is a method for obtaining a compound represented by formula (3-21) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-20) with a halogenating agent (HalR) in a solvent.
  • Re represents a halogen atom
  • manufacturing method Q By replacing the compound represented by formula (3-18) in manufacturing method O with the compound represented by formula (3-20), manufacturing method Q can be carried out in accordance with manufacturing method O.
  • R1, R6, Rc, Rd, and HalR are as defined above.
  • Production method R is a production method for obtaining a compound represented by formula (3-23) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-22) with a halogenating agent (HalR) in a solvent.
  • Rc represents a halogen atom
  • manufacturing method R can be carried out in accordance with manufacturing method C.
  • R1, R6, Rc, Rd, Re and HalR are as defined above.
  • Production method S is a method for obtaining a compound represented by formula (3-24) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-23) with a halogenating agent (HalR) in a solvent.
  • Re represents a halogen atom
  • manufacturing method S By replacing the compound represented by formula (3-18) in manufacturing method O with the compound represented by formula (3-23), manufacturing method S can be carried out in accordance with manufacturing method O.
  • Production method T is a method for synthesizing a compound represented by formula (3-25), which comprises reacting a compound represented by formula (3-23) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
  • production method T By substituting the compound represented by formula (3-23) for the compound represented by formula (3-4) in production method D, production method T can be carried out in accordance with production method D.
  • HalR represents a halogenating agent
  • R1, R5a, Q, R6, Rd, and Re are as defined above.
  • Production method U is a method for obtaining a compound represented by formula (3-26) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-25) with a halogenating agent (HalR) in a solvent.
  • Re represents a halogen atom
  • manufacturing method U By replacing the compound represented by formula (3-18) in manufacturing method O with the compound represented by formula (3-25), manufacturing method U can be carried out in accordance with manufacturing method O.
  • R7 represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group;
  • R8 represents a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group.
  • a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a substituted R9 represents a hydrogen atom, a
  • R10 represents a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 and p are as defined above), and Lv2 represents a leaving group such as a sulfonate group, a mesitylsulfonate group, a 2,
  • Production method V is a production method for obtaining a compound represented by formula (4-2), which comprises reacting a compound represented by formula (4-1) with an aminating agent (NH 2 -Lv2) in a solvent.
  • Aminating agents used in this reaction include hydroxylamine-O-sulfonic acid, O-(diphenylphosphinyl)hydroxylamine, (O-(mesitylsulfonyl)hydroxylamine), O-(2,4-dinitrophenyl)hydroxylamine, etc.
  • the amount of the aminating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (4-1) and the desired reaction proceeds, but is preferably at least 1 equivalent and at most 10 equivalents, and more preferably at least 1 equivalent and at most 5 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; ether solvents such as diethyl ether, 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, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-di
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (4-1).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (4-2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (4-2) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (4-2) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • R5 is a cyano group, a halogen atom, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, C1-C6 alkyl group, C1-C6 haloalky
  • Production method W is a production method for obtaining the compound of the present invention represented by formula (1-a), which includes reacting a compound represented by formula (4-2) with a compound represented by formula (3-27) in a solvent.
  • the pyrazole carboxylic acid represented by formula (3-27) can be converted into an carboxylic acid halide and then reacted with a compound represented by formula (4-2) in the presence of a base.
  • the pyrazole carboxylic acid represented by formula (3-27) can be reacted with a compound represented by formula (4-2) in the presence of a base using a condensing agent.
  • Halogenating agents used to synthesize carboxylic acid halides include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide, etc.
  • the amount of halogenating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-27) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • N,N-dimethylformamide When synthesizing carboxylic acid halides, N,N-dimethylformamide can be used as a catalyst.
  • the amount of catalyst used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (3-27), but is preferably 0.01 equivalents 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 examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.; ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc.; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc.; urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc.; and halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrach
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-27).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C, or below the boiling point of the solvent.
  • the reaction mixture containing the carboxylic acid halide obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the carboxylic acid halide obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the carboxylic acid halide obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent.
  • the method can be set appropriately depending on the desired purity.
  • the amount of the carboxylic acid halide obtained above to be used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less relative to the compound represented by formula (4-2). Next, the reaction in the presence of a base will be described.
  • bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium
  • the amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-27), but is preferably 1 equivalent or more and 30 equivalents or less.
  • a catalyst can be used as an activator for this reaction.
  • catalysts include 4-dimethylaminopyridine and 4-pyrrolidinopyridine.
  • the amount of catalyst used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (4-2), but is preferably 0.01 equivalents 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 examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; 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, and butyl acetate; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolid
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (4-2).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C, or below the boiling point of the solvent.
  • a separation operation by adding water or a suitable aqueous solution to the reaction mixture.
  • an aqueous solution it is possible to arbitrarily use an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary.
  • a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene
  • an ester-based solvent such
  • these solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield. In addition, it is possible to remove insoluble matter by performing a filtration operation, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • reaction mixture containing the compound represented by formula (1-a) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the amount of formula (3-27) used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less relative to the compound represented by formula (4-2).
  • Condensing agents used in this reaction include carbodiimide-based condensing agents such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, N,N'-dicyclohexylcarbodiimide, and N,N'-diisopropylcarbodiimide; imidazole-based dehydration condensing agents such as N,N'-carbonyldiimidazole and 1,1'-carbonyldi(1,2,4-triazole); triazine-based condensing agents such as 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1H-benzotri
  • the amount of condensing agent used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (3-27), but is preferably 1 equivalent or more and 10 equivalents or less.
  • additives can be used together with the condensing agent.
  • additives include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide, N,N'-disuccinimidyl carbonate, and dimethylaminopyridine.
  • the amount of additive used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (3-27), but is preferably 0.1 equivalents or more and 10 equivalents or less.
  • bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium
  • the amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-27), but is preferably 1 equivalent or more and 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.; ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc.; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc.; urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc.; halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachlor
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-27).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C, or below the boiling point of the solvent.
  • a separation operation by adding water or a suitable aqueous solution to the reaction mixture.
  • an aqueous solution it is possible to arbitrarily use an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary.
  • a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene
  • an ester-based solvent such
  • these solvents can be used alone or in any combination of two or more types in any ratio.
  • reaction mixture containing the compound represented by formula (1-a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-a) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • G represents C-R6 or a nitrogen atom
  • R6 represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group
  • Rf represents a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group
  • bases examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[2.2.2]octane, and dimethylaminopyridine; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbon
  • the amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-a), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloro
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-a).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
  • a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (1-b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-b) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Production method Y is a method for obtaining a compound represented by formula (1-d), and includes reacting a compound represented by formula (1-c) with an oxidizing agent (Ox) in a solvent.
  • production method Y can be carried out in accordance with production method F.
  • R1, R5, R7, R8, R9, R10, and Rb are as defined above.
  • Production method Z is a production method for obtaining the compound of the present invention represented by formula (1-e), which includes reacting a compound represented by formula (4-2) with a compound represented by formula (3-28) in a solvent.
  • the pyrazole carboxylic acid represented by formula (3-28) can be converted into an carboxylic acid halide and then reacted with a compound represented by formula (4-2) in the presence of a base.
  • the pyrazole carboxylic acid represented by formula (3-28) can be reacted with a compound represented by formula (4-2) in the presence of a base using a condensing agent.
  • manufacturing method Z By replacing the compound represented by formula (3-27) in manufacturing method W with the compound represented by formula (3-28), manufacturing method Z can be carried out in accordance with manufacturing method W.
  • G, R1, R5, R6, R7, R8, R9, R10, Rb, Rf, and Lv3 are as defined above.
  • Production method AA is a method for obtaining a compound represented by formula (1-f), including the compound of the present invention, and includes reacting a compound represented by formula (1-e) with Rf-C( ⁇ O)-Lv3 in a solvent.
  • Production method AA can be carried out in accordance with production method X by using the compound represented by formula (1-a) in place of the compound represented by formula (1-e).
  • G, R1, R3, R4, R5a, R6, R8, R9, R10, r, and Ox are as defined above.
  • Production method AB is a method for obtaining a compound represented by formula (1-h), and includes reacting a compound represented by formula (1-g) with an oxidizing agent (Ox) in a solvent.
  • manufacturing method AB can be carried out in accordance with manufacturing method F.
  • Production method AC is a method for obtaining a compound represented by formula (1-j), and includes reacting a compound represented by formula (1-i) with R2a-Lv in a solvent in the presence of a base.
  • the compound represented by formula (1-i) is represented by formula (1-k) (In the formula, G, R3, R4, R5, R6, R7, R8, R9, and R10 are as defined above.)
  • the compound represented by formula (1-i) can be handled in the same manner as the compound represented by formula (1-k), and manufacturing method AC can be applied to it. It may be a mixture of the compound represented by formula (1-i) and the compound represented by formula (1-k), and the isomer mixture ratio may be a single isomer or a mixture of any ratio.
  • the R2a-Lv used in this reaction can be obtained commercially or produced by known methods.
  • the amount of R2a-Lv used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-i), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium
  • the amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-i), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloro
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-i).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
  • a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (1-j) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-j) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-j) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • R1a is a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a C2 to C6 phenyl group which may be optionally substituted with 0 to 4 substituents B.
  • Production method AD is a method for obtaining a compound represented by formula (1-L), which includes reacting a compound represented by formula (1-k) with R1a-Lv in a solvent in the presence of a base.
  • manufacturing method AD By substituting the compound represented by formula (1-i) in manufacturing method AC with the compound represented by formula (1-k) and substituting R2a-Lv for R1a-Lv, manufacturing method AD can be carried out in accordance with manufacturing method AC.
  • R2, R6, R7, R8, R9, R10, Rc, Rd, and Re are as defined above.
  • Production method AE is a method for obtaining a compound represented by formula (1-m), which includes reacting a compound represented by formula (4-1) with a compound represented by formula (3-19) in a solvent.
  • a base can be used in this reaction.
  • bases include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • the amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3-19), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloro
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-19).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
  • a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (1-m) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-m) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-m) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • R2, R5a, R6, R7, R8, R9, R10, Q, Rc, and Rd are as defined above.
  • Production method AF is a method for synthesizing a compound represented by formula (1-n), which includes reacting a compound represented by formula (1-m) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
  • manufacturing method AF can be carried out in accordance with manufacturing method P.
  • R2, R5a, R6, R7, R8, R9, R10, Q, and Rd are as defined above.
  • Production method AG is a method for synthesizing a compound represented by formula (1-o), which is a production intermediate for the compound of the present invention, and includes reacting a compound represented by formula (1-n) in a solvent under acidic or basic conditions.
  • the acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, etc., or organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. There are no particular limitations as long as the desired reaction proceeds.
  • the amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more relative to the compound represented by formula (1-n).
  • liquid acids can also be used as a solvent.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, 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, and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-n).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
  • 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 desired reaction proceeds.
  • the amount of base used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (1-n) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 30 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and the like, alcohol solvents such as methanol, ethanol, isopropanol, and the like, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, and the like, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-n).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
  • Reactions under acidic and basic conditions can be treated by the same method after the reaction.
  • a 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, or saline solution can be used as desired.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary.
  • solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired
  • reaction mixture containing the compound represented by formula (1-o) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-o) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-o) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Production method AH is a method for obtaining a compound represented by formula (1-p), which includes reacting a compound represented by formula (1-o) with an azide compound in a solvent in the presence of t-butanol.
  • Azide compounds used in this reaction include diphenylphosphoryl azide, etc.
  • the amount of the azide compound used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-o), and is not particularly limited as long as the desired reaction proceeds, but is usually at least 1 equivalent and no more than 10 equivalents.
  • t-butanol used in this reaction is not particularly limited as long as it is at least one equivalent relative to the compound represented by formula (1-o), and the desired reaction proceeds.
  • t-butanol itself can also be used as the solvent.
  • Solvents used in this reaction include alcohol solvents such as t-butanol, ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any ratio.
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-o).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
  • a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (1-p) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-p) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-p) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Production method AI is a method for obtaining a compound represented by formula (1-r), and includes reacting a compound represented by formula (1-q) with an acid in a solvent.
  • the acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid or hydrobromic acid, or organic acids such as methanesulfonic acid, p-toluenesulfonic acid, or trifluoroacetic acid. There are no particular limitations as long as the desired reaction proceeds.
  • the amount of acid used in this reaction is not particularly limited as long as it is a catalytic amount relative to the compound represented by formula (1-q) and the desired reaction proceeds, but is usually at least one equivalent, and can also be used as a solvent.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acid solvents such as hydrochloric acid and trifluoroacetic acid, ether solvents such as diethyl ether, 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, and butyl acetate, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-q).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary.
  • solvents can be used alone or in a mixture of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according
  • reaction mixture containing the compound represented by formula (1-r) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-r) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-r) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • the compound represented by formula (1-r) can be a useful intermediate for obtaining the compound represented by formula (1-2), which is the compound of the present invention.
  • manufacturing method AJ can be carried out in accordance with manufacturing method X.
  • R1, R6, R7, R8, R9, R10, Rc, Rd, and Re are as defined above.
  • Production method AK is a method for obtaining a compound represented by formula (1-t), and includes reacting a compound represented by formula (4-1) with a compound represented by formula (3-24) in a solvent.
  • manufacturing method AK can be carried out in accordance with manufacturing method AE.
  • R1, R5a, R6, R7, R8, R9, R10, Q, Rc, and Rd are as defined above.
  • Production method AL is a method for synthesizing a compound represented by formula (1-u), which includes reacting a compound represented by formula (1-t) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
  • manufacturing method AL can be carried out in accordance with manufacturing method AF.
  • Production method AM is a method for synthesizing a compound represented by formula (1-v), which includes reacting a compound represented by formula (1-u) in a solvent under acidic or basic conditions.
  • manufacturing method AM can be carried out in accordance with manufacturing method AG.
  • Production method AN is a method for obtaining a compound represented by formula (1-w), which includes reacting a compound represented by formula (1-v) with an azide compound in a solvent in the presence of t-butanol.
  • Azide compounds used in this reaction include diphenylphosphoryl azide, etc.
  • the amount of the azide compound used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-v), and is not particularly limited as long as the desired reaction proceeds, but is usually at least 1 equivalent and no more than 10 equivalents.
  • the amount of t-butanol used in this reaction is not particularly limited as long as it is at least one equivalent relative to the compound represented by formula (1-v), and the desired reaction proceeds.
  • Tertiary butanol itself can also be used as a solvent.
  • Solvents used in this reaction include alcohol solvents such as t-butanol, ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any ratio.
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-v).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane.
  • solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
  • reaction mixture containing the compound represented by formula (1-w) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-w) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-w) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • Production method AO is a method for obtaining a compound represented by formula (1-y), which includes reacting a compound represented by formula (1-x) with an acid in a solvent.
  • the acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid or hydrobromic acid, or organic acids such as methanesulfonic acid, p-toluenesulfonic acid, or trifluoroacetic acid. There are no particular limitations as long as the desired reaction proceeds.
  • the amount of acid used in this reaction is not particularly limited as long as it is a catalytic amount relative to the compound represented by formula (1-x) and the desired reaction proceeds, but is usually at least one equivalent, and can also be used as a solvent.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acid solvents such as hydrochloric acid and trifluoroacetic acid, ether solvents such as diethyl ether, 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, and butyl acetate, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
  • the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-x).
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
  • an aqueous solution any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution.
  • a solvent that is not compatible with water such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary.
  • solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according
  • reaction mixture containing the compound represented by formula (1-y) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
  • reaction mixture containing the compound represented by formula (1-y) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
  • the reaction mixture containing the compound represented by formula (1-y) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
  • the method may be appropriately set depending on the desired purity.
  • the compound represented by formula (1-y) can be a useful intermediate for obtaining the compound represented by formula (1-1), which is the compound of the present invention.
  • manufacturing method AP can be carried out in accordance with manufacturing method AA.
  • the compounds represented by formula (1-1) and formula (1-2) can be produced by arbitrarily combining the above-mentioned Production Method A to Production Method AP.
  • the compounds represented by formula (1-1) and formula (1-2) can be produced by arbitrarily combining known methods with Production Method A to Production Method AP.
  • the compound of the present invention can be used as an agricultural chemical because it can control organisms harmful to plants or animals (e.g., humans, and non-human mammals such as livestock and pets, and birds), especially plants.
  • plants or animals e.g., humans, and non-human mammals such as livestock and pets, and birds
  • Specific examples include insecticides, fungicides, herbicides, and plant growth regulators.
  • it is an insecticide.
  • Methods for applying the composition containing the compound of the present invention include contacting the composition with a plant body or seed, or including the composition in cultivation soil and contacting the roots or rhizomes of the plant.
  • Specific examples include foliage spraying of the composition onto individual plants, injection, seedling box treatment, cell tray treatment, spraying onto plant seeds, smearing onto plant seeds, soaking into plant seeds, dressing onto plant seeds, spraying onto the soil surface, soil incorporation after spraying onto the soil surface, injection into soil, soil incorporation after injection into soil, soil drenching, soil incorporation after soil drenching, etc.
  • any application method used by those skilled in the art will be sufficiently effective.
  • plants refers to things that live without moving and use photosynthesis.
  • Specific examples include rice, wheat, barley, corn, coffee, bananas, grapes, apples, pears, peaches, cherries, persimmons, citrus, soybeans, beans, cotton, strawberries, potatoes, cabbage, lettuce, tomatoes, cucumbers, eggplants, watermelons, sugar beets, spinach, snow peas, pumpkins, sugarcane, tobacco, peppers, sweet potatoes, taro, konjac, cotton, sunflowers, roses, tulips, chrysanthemums, grass, and F1 varieties thereof.
  • genetically modified crops that are produced by artificially manipulating genes and do not originally exist in nature, such as soybeans, corn, cotton, etc.
  • plant body as used in the present invention collectively refers to all parts that constitute the above-mentioned plant individual, including, for example, stems, leaves, roots, seeds, flowers, and fruits.
  • seeds refers to those that store nutrients for young plants to germinate and are used for agricultural propagation.
  • Specific examples include seeds of corn, soybeans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, snow peas, pumpkin, sugar cane, tobacco, bell pepper, rapeseed, etc., seeds of F1 varieties of these, seed potatoes such as taro, potato, sweet potato, and konjac, bulbs such as edible lilies and tulips, seed bulbs such as scallions, and seeds and tubers of genetically modified crops.
  • the compound of the present invention has excellent effects as an active ingredient of a pest control agent, and can be used against pests, particularly harmful arthropods, that are the subject of control in various agricultural settings, such as farm fields, paddy fields, tea plantations, orchards, pastures, lawns, forests, gardens, and roadside trees.
  • pests particularly harmful arthropods
  • the compound of the present invention exhibits a controlling effect against stored grain pests which damage grains and the like stored in warehouses.
  • the compound of the present invention has a controlling effect against insects such as wood-eating pests which damage wood in buildings, furniture, stored wood and the like.
  • the compound of the present invention has an exterminating effect against sanitary pests which adversely affect human living environments such as houses.
  • the compounds of the present invention have an antiparasitic effect against external and internal parasites of mammals and birds.
  • the compound of the present invention can control any of the pests such as mites, crustaceans, mollusks and nematodes which appear and cause damage in the same situations as those mentioned above.
  • the compound of the present invention is effective against pests such as insects, mites, crustaceans, spiders, centipedes and other arthropods, mollusks, nematodes, etc. Specific examples of pests are shown below, but are not limited to these.
  • Tea spine whitefly (Aleurocanthus camelliae), citrus spine whitefly (Aleurocanthus spiniferus), grape whitefly (Aleurolobus taonabae), Amrasca biguttula biguttula, red scale insect (Aonidiella aurantii), bean black aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), snow willow aphid (Aphis spiraecola), Arboridia apicalis, Aulacorthum solani, Balculutha saltuella, Bemisia argentifolii, Bemisia tabaci, Blissus leucopterus, Brachycaudus helichrysi, Brevicoryne brassicae, Cacopsylla chinensis, Cacopsylla pyricola,
  • the pest animal is preferably an arthropod pest, more preferably a Hemiptera pest or a Lepidoptera pest.
  • the compound of the present invention has a remarkable control effect against the above-mentioned pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc., and the effect as the pest control agent of the present invention can be obtained by treating the paddy field water, stems, leaves, or soil of paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc. before the emergence of the pests or at the time when their emergence is confirmed, in accordance with the time when the emergence of the pests is predicted.
  • the compound of the present invention has a remarkable control effect against stored grain pests that occur during the storage of harvested crops, etc.
  • a pest control agent containing the compound of the present invention as an active ingredient may be applied to the harvested crops or the storage location of the harvested crops by post-harvest treatment such as spraying, smearing, coating, immersion, powder coating, fumigation, smoking, or pressurized injection.
  • the compound of the present invention when applied to plant seeds, can prevent damage caused by pests such as agricultural pests that occur in plants after sowing. That is, the compound of the present invention can be brought into contact with the plant seeds by applying an effective amount for pest control of a pest control agent containing the compound of the present invention as an active ingredient directly or after appropriate dilution or suspension in water or the like to the plant seeds through treatment such as spraying, smearing, immersion or dusting.
  • the compound of the present invention has a remarkable control effect against wood-eating pests such as termites, powderpost beetles, long-horn beetles, lacertilia beetles and long-horn beetles, and can control the above wood-eating pests by treating the soil or wood of buildings, etc.
  • the compound of the present invention shows a control effect against various pests, and has an effect of protecting useful crops, and also shows an excellent control effect as an insecticide or acaricide at a low dose, so that it has an effect of greatly contributing to reducing the burden on the environment.
  • the compound of the present invention also shows an excellent control effect when used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides, etc.
  • the compound of the present invention may be used alone, but is preferably mixed with a solid carrier, liquid carrier, gas carrier, surfactant, adhesive, dispersant, stabilizer, etc., and can be used as a composition such as a dust, hydrated powder, hydrated granule, water-soluble powder, water-soluble granule, granule, emulsion, liquid, microemulsion, aqueous suspension preparation, aqueous emulsion preparation, suspoemulsion preparation, etc. As long as the effect is exhibited, there is no limitation to these compositions.
  • the compound of the present invention may be used alone, but is preferably mixed with a suitable solid or liquid carrier, and further, if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anti-caking agents, disintegrants, antifoaming agents, preservatives, anti-decomposition agents, etc. may be added to produce a liquid concentrate, an emulsifiable concentrate, a wettable powder, a water soluble powder, a water dispersible granule, etc.
  • the composition can be used in any dosage form, such as water-soluble granules, water-soluble granules, suspension concentrates, concentrated emulsions, suspoemulsions, microemulsions, dustable powders, granules, tablets, and emulsifiable gels.
  • the above-mentioned formulations can be provided in water-soluble packaging such as water-soluble capsules and water-soluble film bags. As long as the effect is exhibited, the composition is not limited to these compositions.
  • the inert carrier that can be used in the present invention may be either solid or liquid.
  • materials that can be used as a solid inert carrier include soybean flour, grain flour, wood flour, bark powder, sawdust, tobacco stem powder, walnut shell powder, bran, cellulose powder, residues after plant extract extraction, synthetic polymers such as crushed synthetic resins, clays (e.g., kaolin, bentonite, acid clay, etc.), talcs (e.g., talc, pyrophyllide, etc.), silicas (e.g., diatomaceous earth, silica sand, mica, white carbon [a synthetic highly dispersed silicic acid also known as hydrous fine powder silicon or hydrous silicic acid, some products contain calcium silicate as the main component.]), activated carbon, sulfur powder, pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammoni
  • Materials that can be liquid inert carriers are selected from those that have solvent properties themselves, as well as those that can disperse active ingredient compounds with the aid of an auxiliary even if they do not have solvent properties.
  • the following carriers can be exemplified as representative examples. These are used alone or in the form of a mixture of two or more types.
  • water For example, water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (e.g., diethyl ether, dioxane, cellosolve, diisobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), and the like.
  • alcohols e.g., methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.
  • ketones e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.
  • Surfactants include, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono or di)phenyl ethers, polyoxyethylene (mono, di or tri)styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono or di) esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol, and nonionic surfactants such as alkyl glycosides, alkyl sulfate ester salts, alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, and the
  • anionic surfactants such as phosphates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfates or phosphate ester salts, polyoxyethylene (mono- or di-) alkylphenyl ether sulfates or phosphate ester salts, polyoxyethylene (mono-, di-, or tri-) styrylphenyl ether sulfates or phosphate ester salts, polycarboxylates (e.g., polyacrylates, polymaleates, and copolymers of maleic acid and olefins, etc.) and polystyrenesulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such
  • the content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. These surfactants may be used alone or in combination of two or more types.
  • the application amount and application concentration of the composition containing the compound of the present invention vary depending on various factors, such as the purpose, the target pest, the growth condition of the crop, the tendency of the pest to occur, weather, environmental conditions, the formulation type, the application method, the application location, and the application time, but generally, an amount of 0.0001 to 5000 ppm as the active ingredient is appropriate, and it is preferable to use it at a concentration of 0.01 to 1000 ppm. Furthermore, it is generally preferable to use it at a concentration of 1 to 300 g of active ingredient per 10 a. Furthermore, the amount used in the case of seed treatment is 0.0001 to 1000 g as the active ingredient per 1 kg of seeds, and preferably 0.001 to 100 g.
  • composition containing the compound of the present invention When used as a foliage spray treatment for plant individuals, a spray treatment for the soil surface, a soil injection treatment, or a soil drenching treatment, it may be diluted with an appropriate carrier at an appropriate concentration before treatment. When the composition containing the compound of the present invention is brought into contact with plant seeds, it may be diluted to an appropriate concentration and then used by immersing, coating, spraying or smearing the plant seeds.
  • the amount of the composition used when immersing, coating, spraying or smearing is usually about 0.05 to 50% of the weight of the dry plant seeds as the amount of active ingredient, preferably 0.1 to 30%, but this may be set appropriately depending on the form of the composition and the type of plant seeds to be treated, and is not limited to these ranges.
  • the amount of the active ingredient of the compound of the present invention represented by formula (1-1) or formula (1-2) is 0.1 to 90% by weight, preferably 1 to 90% by weight, more preferably 1 to 50% by weight, and particularly preferably 3 to 50% by weight.
  • the amount of the active ingredient of the compound of the present invention represented by formula (1-1) or formula (1-2) is usually 0.1-20% by weight for dusts, 5-50% by weight for emulsifiable concentrates, 3-90% by weight for wettable powders, 0.1-20% by weight for granules, 5-90% by weight for flowable formulations, and 3-90% by weight for water dispersible granules.
  • the amount of the carrier in each formulation is usually 60-99.9% by weight for dusts, 40-95% by weight for emulsifiable concentrates, 10-90% by weight for wettable powders, 80-99.9% by weight for granules, 10-95% by weight for flowable formulations, and 10-90% by weight for water dispersible granules.
  • the amount of adjuvant is usually 0.1 to 20% by weight for dusts, 1 to 20% by weight for emulsifiable concentrates, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, 0.1 to 20% by weight for flowable preparations, and 0.1 to 20% by weight for wettable powders.
  • composition containing the compound of the present invention may be used in a mixture with other pesticides, such as fungicides, insecticides, acaricides, nematicides, herbicides, biological pesticides, and plant growth regulators, disease control agents having nucleic acids as active ingredients (WO 2014/062775), soil conditioners, or fertilizers, as necessary.
  • pesticides such as fungicides, insecticides, acaricides, nematicides, herbicides, biological pesticides, and plant growth regulators, disease control agents having nucleic acids as active ingredients (WO 2014/062775), soil conditioners, or fertilizers, as necessary.
  • Methods for using the compound of the present invention represented by formula (1-1) or formula (1-2) and other pesticides in a mixture include a method of formulating the compound of the present invention represented by formula (1-1) or formula (1-2) and other pesticides in one formulation, a method of mixing the two before use, a method of using both simultaneously, each formulated in a different formulation, or a method of using one of the two formulated in a different formulation and then using the other.
  • insecticides are as shown in group b below, and include their salts, isomers and N-oxides. However, known insecticides are not limited to these.
  • Group b ⁇ b-1: Carbamate Acetylcholinesterase (AChE) Inhibitor> b-1: Carbamate acetylcholinesterase (AChE) inhibitors, such as [b-1.1] phosphocarb, [b-1.2] alanycarb, [b-1.3] butocarboxim, [b-1.4] butoxycarboxim, and [b-1.5] thiodicarb.
  • ⁇ b-2 Organophosphorus acetylcholinesterase (AChE) inhibitors>
  • b-2 As an organophosphorus acetylcholinesterase (AChE) inhibitor, [b-2.1] acephate, [b-2.2] azamethiphos, [b-2.3] azinphos-methyl, [b-2.4] azinphos-ethyl, [b-2.5] ethephon, [b-2.6] cadusafos usafos), [b-2.7] chlorethoxyphos, [b-2.8] chlorfenvinphos, [b-2.9] chlormephos, [b-2.10] chlorpyrifos, [b-2.11] chlorpyrifos-methyl pyrifos-methyl, [b-2.12] coumaphos, [b-2.13] cyanophos, [b-2.14] demeton-S-methyl, [b-2.15] diazinon, [b-2.16] diclof
  • ⁇ b-5 sodium channel modulator>
  • b-5 sodium channel modulators, including [b-5.1] acrinathrin, [b-5.2] allethrin, [b-5.3] bifenthrin, [b-5.4] bioallethrin, and [b-5.5] bioallethrin S-cyclopentenyl isomer.
  • ⁇ b-6 Nicotinic acetylcholine receptor (nAChR) competitive modulator>
  • b-6 Nicotinic acetylcholine receptor (nAChR) competitive modulators, including: [b-6.1] acetamiprid, [b-6.2] clothianidin, [b-6.3] dinotefuran, [b-6.4] imidacloprid, [b-6.5] nitenpyram, [b-6.6] thiacloprid, [b-6.7] thiamethoxam, [b-6.8] nicotine, [b-6.9] nicotine sulfate sulfate), [b-6.10] sulfoxaflor, [b-6.11] flupyradifurone, [b-6.12] triflumezopyrim, and the like.
  • ⁇ b-7 Nicotinic acetylcholine receptor (nAChR) allosteric modulator - site I> b-7: Nicotinic acetylcholine receptor (nAChR) allosteric modulators - site I include [b-7.1] spinosad, [b-7.2] spinetoram, and the like.
  • ⁇ b-8 Glutamate-gated chloride channel (GluCl) allosteric modulator>
  • b-8 Glutamate-gated chloride ion channel (GluCl) Allosteric modulators include [b-8.1] abamectin, [b-8.2] emamectin benzoate, [b-8.3] lepimectin, [b-8.4] milbemectin, and the like.
  • Juvenile hormone analogues include, for example, [b-9.1] hydroprene, [b-9.2] kinoprene, [b-9.3] methoprene, [b-9.4] fenoxycarb, and [b-9.5] pyriproxyfen.
  • non-specific (multi-site) inhibitors include: [b-10.1] methyl bromide, [b-10.2] chloropicrin, [b-10.3] cryolite, [b-10.4] sulfuryl fluoride, [b-10.5] borax, [b-10.6] boric acid, [b-10.7] disodium octaborate, [b-10.8] sodium metaborate [b-10.10] dazomet, [b-10.11] metam, [b-10.12] carbam sodium salt, and the like.
  • ⁇ b-11 Chordotonal organ TRPV channel modulator>
  • b-11 Chordotonal organ TRPV channel modulators include, for example, [b-11.1] pymetrozine, [b-11.2] pyrifluquinazon, [b-11.3] afidopyropene, and the like.
  • ⁇ b-12 Mite growth inhibitor acting on CHS1>
  • b-12 Examples of mite growth inhibitors acting on CHS1 include [b-12.1] clofentezine, [b-12.2] diflovidazin, [b-12.3] hexythiazox, and [b-12.4] etoxazole.
  • ⁇ b-13 Microorganism-derived insect midgut membrane disrupting agent>
  • b-13 As microbial insect midgut membrane disrupting agents, [b-13.1] Bacillus thuringiensis, [b-13.2] B. t. israensis, [b-13.3] B. t. aizawai, [b-13.4] B. t. kurstaki, [b-13.5] B. t. tenebrionis, [b-13.6] Proteins contained in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.
  • Mitochondrial ATP synthase inhibitors include, for example, [b-14.1] diafenthiuron, [b-14.2] azocyclotin, [b-14.3] cyhexatin, [b-14.4] fenbutatin oxide, [b-14.5] propargite, and [b-14.6] tetradifon.
  • ⁇ b-15 Oxidative phosphorylation uncouplers that disrupt the proton gradient> b-15: as an oxidative phosphorylation uncoupler that disrupts the proton gradient; [b-15.1] chlorfenapyr, [b-15.2] DNOC (dinitro-ortho-cresol), [b-15.3] binapacryl, [b-15.4] sulfuramide,
  • nAChR Nicotinic acetylcholine receptor
  • b-16 Nicotinic acetylcholine receptor (nAChR) channel blockers include, for example, [b-16.1] bensultap, [b-16.2] cartap hydrochloride, [b-16.3] thiocyclam, [b-16.4] thiosultap, [b-16.5] thiosultap sodium salt, and [b-16.6] monosultap.
  • Chitin biosynthesis inhibitor acting on CHS1 include: [b-17.1] bistrifluron, [b-17.2] chlorfluazuron, [b-17.3] diflubenzuron, [b-17.4] flucycloxuron, and [b-17.5] flufenoxuron. on), [b-17.6] hexaflumuron, [b-17.7] lufenuron, [b-17.8] novaluron, [b-17.9] noviflumuron, [b-17.10] teflubenzuron, [b-17.11] triflumuron, and the like.
  • ⁇ b-18 Chitin biosynthesis inhibitor type 1> b-18: Chitin biosynthesis inhibitor type 1 includes [b-18.1] buprofezin, etc.
  • b-19 Diptera insect molting inhibitor>
  • b-19 Diptera molting inhibitors include [b-19.1] cyromazine, and the like.
  • ⁇ b-20: ecdysone receptor agonist> b-20: Molting hormone (ecdysone) receptor agonists include, for example, [b-20.1] chromafenozide, [b-20.2] halofenozide, [b-20.3] methoxyfenozide, and [b-20.4] tebufenozide.
  • Octopamine receptor agonist includes [b-21.1] amitraz, and the like.
  • ⁇ b-22 mitochondrial electron transport complex III inhibitor>
  • Mitochondrial electron transport complex III inhibitors include, for example, [b-22.1] hydramethylnon, [b-22.2] acequinocyl, [b-22.3] fluacrypyrim, and [b-22.4] bifenazate.
  • Mitochondrial electron transport complex I inhibitors include, for example, [b-23.1] fenazaquin, [b-23.2] fenpyroximate, [b-23.3] pyridaben, [b-23.4] pyrimidifen, [b-23.5] tebufenpyrad, [b-23.6] tolfenpyrad, and [b-23.7] rotenone.
  • b-24 Voltage-dependent sodium channel blocker>
  • Voltage-dependent sodium channel blockers include, for example, [b-24.1] indoxacarb, [b-24.2] metaflumizone, and the like.
  • Acetyl CoA carboxylase inhibitor >
  • Acetyl CoA carboxylase inhibitors include, for example, [b-25.1] spirodiclofen, [b-25.2] spiromesifen, [b-25.3] spiropidion, and [b-25.4] spirotetramat.
  • ⁇ b-26 mitochondrial electron transport chain complex IV inhibitor>
  • Mitochondrial electron transport complex IV inhibitors include, for example, [b-26.1] aluminum phosphide, [b-26.2] calcium phosphide, [b-26.3] hydrogen phosphide, [b-26.4] zinc phosphide, [b-26.5] calcium cyanide, [b-26.6] potassium cyanide, and [b-26.7] sodium cyanide.
  • ⁇ b-27 mitochondrial electron transport complex II inhibitor>
  • Mitochondrial electron transport complex II inhibitors include [b-27.1] cyenopyrafen, [b-27.2] cyflumetofen, [b-27.3] pyflubumid, and the like.
  • b-28 Ryanodine receptor modulator>
  • b-28 Ryanodine receptor modulators include, for example, [b-28.1] chlorantraniliprole, [b-28.2] cyantraniliprole, [b-28.3] flubendiamide, [b-28.4] cyclaniliprole, and [b-28.5] tetraniliprole.
  • ⁇ b-29 Chordotonal organ modulator target site unidentified> b-29: Chordotonal organ modulators.
  • Target site unspecified insecticides include [b-29.1] flonicamid, and the like.
  • GABA-gated chloride ion channel allosteric modulator > b-30: GABA-gated chloride ion channel allosteric modulators include, for example, [b-30.1] broflanilide, [b-30.2] fluxametamide, and the like.
  • baculovirus> b-31 Baculovirus> b-31: Examples of baculoviruses include [b-31.1] Cydia pomonella GV (Cydia pomonella GV), [b-31.2] Thaumatotibia leucotreta GV (Thaumatotibia leucotreta GV), [b-31.3] Anticarsia gemmatalis MNPV (Anticarsia gemmatalis MNPV), [b-31.4] Helicoverpa armigera NPV (Helicoverpa armigera NPV), and the like.
  • ⁇ b-32 Nicotinic acetylcholine receptor (nAChR) allosteric modulator site II> b-32: Nicotinic acetylcholine receptor (nAChR) allosteric modulator site II includes [b-32.1] GS-omega/kappa HXTX-Hv1a peptide and the like.
  • b-33 Other insecticides> b-33: Other insecticides include, [b-33.1] azadirachtin, [b-33.2] benzoximate, [b-33.3] phenisobromolate, [b-33.4] chinomethionate, [b-33.5] dicofol, [ b-33.6] lime sulfur (CaSx), [b-33.7] manzeb, [b-33.8] pyridalyl, [b-33.9] sulfur, [b-33.10] bromopropylate, [b-33.11] Burkholderia spp.
  • the components contained in the fungicide are as shown in group c below, and include their salts, isomers and N-oxides. However, known fungicides are not limited to these.
  • Phenylamide fungicides include, for example, [c-1.1] benalaxyl, [c-1.2] benalaxyl M or kiraraxyl, [c-1.3] furalaxyl, [c-1.4] metalaxyl, [c-1.5] metalaxyl M or mefenoxam, [c-1.6] oxadixyl, and [c-1.7] ofurace.
  • ⁇ c-2 Hydroxy(2-amino)pyrimidine fungicide>
  • c-2 Hydroxy(2-amino)pyrimidine fungicides include [c-2.1] bupirimate, [c-2.2] dimethylimol, and [c-2.3] ethirimol.
  • ⁇ c-4 Carboxylic acid fungicide>
  • c-4 Carboxylic acid fungicides include [c-4.1]octhilinone, etc.
  • ⁇ c-5 ⁇ -tubulin polymerization inhibitor>
  • c-5 ⁇ -tubulin polymerization inhibitors include, for example, [c-5.1] benomyl, [c-5.2] carbendazim, [c-5.3] fuberidazole, [c-5.4] thiabendazole, [c-5.5] thiophanate, [c-5.6] thiophanate-methyl, [c-5.7] diethofencarb, [c-5.8] zoxamide, and [c-5.9] ethaboxam.
  • ⁇ C-6 Cell division inhibitor>
  • c-6 Cell division inhibitors include, for example, [c-6.1] pencycuron, etc.
  • ⁇ c-7 Delocalization of Spectrin-like Protein>
  • c-7 Examples of fungicides involved in the delocalization of spectrin-like proteins include [c-7.1] fluopicolide, [c-7.2] fluopimomide, and the like.
  • ⁇ c-8 Actin/myosin/fimbrin functions>
  • c-8 Bactericides relating to actin/myosin/fimbrin function include [c-8.1] phenamacril, [c-8.2] metrafenone, and [c-8.3] pyriofenone.
  • ⁇ c-9 Complex I: NADH oxidoreductase inhibitor>
  • c-9 Complex I: NADH oxidoreductase inhibitors include [c-9.1] diflumetrim, [c-9.2] tolfenpyrad, [c-9.3] fenazaquin, and the like.
  • ⁇ c-10 SDHI agents (succinate dehydrogenase inhibitors)> c-10: SDHI agents (succinate dehydrogenase inhibitors): [c-10.1] benodanil, [c-10.2] benzovindiflupyr, [c-10.3] bixafen, [c-10.4] boscalid, [c-10.5] carboxin, [c-10.6] phenoxyethanol, fenfuram, [c-10.7] fluopyram, [c-10.8] flutolanil, [c-10.9] fluxapyroxad, [c-10.10] furametpyr, [c-10.11] isofetamide, [c-10.12] isopyrazam sopyrazam, [c-10.13] mepronil, [c-10.14] oxycarboxin, [c-10.15] penthiopyrad, [c-10.16] penflufen, [c-10.17] pydiflumetofen, [c-10.18] sed
  • QoI agents include, [c-11.1] azoxystrobin, [c-11.2] coumoxystrobin, [c-11.3] dimoxystrobin, [c-11.4] enoxastrobin, [c-11.5] famoxadone, [c- 11.6] fenamidone, [c-11.7] phenaminestrobin, [c-11.8] flufenoxystrobin, [c-11.9] fluoxastrobin, [c-11.10] kresoxim-methyl, [c-11.11] mandestrobin (mandestrobin), [c-11.12] metominostrobin, [c-11.13] orysastrobin, [c-11.14] picoxystrobin, [c-11.15] pyraclostrobin, [c-11.16] pyrametostrobin n), [c-11.17] pyraoxystrobin, [c-11
  • c-12 QiI agent (quinone internal inhibitor)>
  • QiI agents (quinone internal inhibitors) include, for example, [c-12.1] amisulbrom, [c-12.2] cyazofamid, and [c-12.3] fenpicoxamid.
  • c-14: ATP synthase inhibitors include, for example, [c-14.1] triphenyltin acetate (fentin acetate), [c-14.2] triphenyltin chloride (fentin chloride), [c-14.3] triphenyltin hydroxide (fentin hydroxide), and the like.
  • ⁇ c-15 ATP transport> c-15: Examples of fungicides related to ATP transport include [c-15.1]silthiofam.
  • ⁇ c-16 QoSI agent (quinone external stigmatellin binding subsite inhibitor)> c-16: QoSI agents (quinone external stigmatellin binding subsite inhibitors) include [c-16.1] ametoctradin, etc.
  • c-18 Protein biosynthesis inhibitors include, for example, [c-18.1] blasticidin S, [c-18.2] kasugamycin, [c-18.3] streptomycin, and [c-18.4] oxytetracycline.
  • c-19 Signal transduction inhibitors include, for example, [c-19.1] quinoxyfen, [c-19.2] proquinazid, [c-19.3] fenpiclonil, [c-19.4] fludioxonil, [c-19.5] chlorzolinate, [c-19.6] dimethachlon, [c-19.7] iprodione, [c-19.8] procymidone, and [c-19.9] vinclozolin.
  • ⁇ C-20 Lipid and cell membrane biosynthesis inhibitor> c-20: As an inhibitor of lipid and cell membrane biosynthesis, [c-20.1] edifenphos, [c-20.2] iprobenfos, [c-20.3] isoprothiolane, [c-20.4] pyrazophos, [c-20.5] biphenyl, [c-20.6] chloroneb, [c-20.7] dicloran, [c-20.8] quintozene, [c-20.9] tecnazene, [c-20.10] tolclofos-methyl, [c-20.11] etridiazole [c-20.12] iodocarb, [c-20.13] propamocarb, and [c-20.14] prothiocarb.
  • C-21 Fungicides related to cell membrane disruptors include, for example, [C-21.1] extract from Melaleuca alternifolia, [C-21.2] plant oils (mixtures): eugenol, geraniol, thymol, and the like.
  • ⁇ c-22 Ergosterol binder>
  • c-22 Examples of fungicides related to ergosterol binding include [c-22.1] natamycin.
  • c-24 DMI agents (demethylation inhibitors)> c-24: DMI agents (demethylation inhibitors): [c-24.1] azaconazole, [c-24.2] bitertanol, [c-24.3] bromuconazole, [c-24.4] cyproconazole, [c-24.5] difenoconazole, [c-24.6] diniconazole [c-24.7] diniconazole M, [c-24.8] epoxyconazole, [c-24.9] etaconazole, [c-24.10] fenarimol, [c-24.11] fenbuconazole, [c-24.12] fluquinconazole [c-24.13] quinconazole, [c-24.14] flusilazole, [c-24.15] flutriafol, [c-24.16] hexaconazole, [c-24.17] imazalil, [c-24.18] imibenconazole azol, [
  • c-25 Amine-based disinfectants>
  • Amine fungicides include, for example, [c-25.1] aldimorph, [c-25.2] dodemorph, [c-25.3] fenpropimorph, [c-25.4] tridemorph, [c-25.5] fenpropidin, [c-25.6] piperalin, and [c-25.7] spiroxamine.
  • ⁇ c-26 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis> c-26: 3-keto reductase inhibitors in the C4 demethylation of sterol biosynthesis include [c-26.1] fenhexamid, [c-26.2] fenpyrazamine, and the like.
  • ⁇ c-27 Squalene epoxidase inhibitor in sterol biosynthesis>
  • c-27 Squalene epoxidase inhibitors of sterol biosynthesis include [c-27.1] pyributicarb, [c-27.2] naftifine, [c-27.3] terbinafine, and the like.
  • c-28 Cell wall biosynthesis inhibitor>
  • c-28 Cell wall biosynthesis inhibitors include, for example, [c-28.1] polyoxins, [c-28.2] dimethomorph, [c-28.3] flumorph, [c-28.4] pyrimorph, [c-28.5] benthiavalicarb, [c-28.6] benthiavalicarb-isopropyl, [c-28.7] iprovalicarb, [c-28.8] mandipropamid, and [c-28.9] valifenalate.
  • c-29 Melanin biosynthesis inhibitors include, for example, [c-29.1] phthalide or phthalide, [c-29.2] pyroquilone, [c-29.3] tricyclazole, [c-29.4] carpropamid, [c-29.5] diclocymet, [c-29.6] fenoxanil, and [c-29.7] tolprocarb.
  • ⁇ C-30 Host plant resistance inducer> c-30: Host plant resistance inducers: [c-30.1] acibenzolar-S-methyl, [c-30.2] probenazole, [c-30.3] tiadinil, [c-30.4] isotianil, [c-30.5] laminarin, [c-30.6] extract from Reynoutria sachalinensis (giant knotweed), [c-30.7] Bacillus mycoides isolate J ), [c-30.8] cell walls of Saccharomyces cerevisiae strain LAS117, [c-30.9] fosetyl, [c-30.10] phosphorous acid, [c-30.11] sodium phosphorous acid, [c-30.12] ammonium phosphorous acid, [c-30.13] potassium phosphorous acid, and the like.
  • Dithiocarbamate fungicides include, for example, [c-31.1] mancozeb, [c-31.2] manzeb, [c-31.3] maneb, [c-31.4] metiram, [c-31.5] propineb, [c-31.6] thiuram, [c-31.7] zinc thiazole, [c-31.8] zineb, [c-31.9] ziram, and [c-31.10] ferbam.
  • Phthalimide fungicides include, for example, [c-32.1] captan, [c-32.2] captafol, [c-32.3] folpet, and [c-32.4] fluorofolpet.
  • c-33 Guanidine-based fungicide>
  • Guanidine fungicides include, for example, [c-33.1] guazatine, [c-33.2] iminoctadine, [c-33.3] iminoctadine albesilate, and [c-33.4] iminoctadine triacetate.
  • ⁇ C-34 Multi-site contact-activated fungicide>
  • c-34 As a multi-site contact-activated fungicide, [c-34.1] chlorothalonil, [c-34.2] dichlofluanid, [c-34.3] tolylfluanid, [c-34.4] basic copper chloride, [c-34.5] copper II hydroxide, [c-34.6] basic copper sulfate, [c-34.7] organocuprolide compound), [c-34.8] dodecylbenzenesulphonic acid bisethylenediamine copper complex salt [II] dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt), [c-34.9] sulfur, [c-34.10] fluoroimide, [c-34.11] anilazine, [c-34.12] dithianon, [c-34.13] chinomethionate or quinomethionate, [c-34.14] methasulfocarb, and the like
  • ⁇ C-35 Biological pesticides with multiple modes of action> c-35: As a biological control agent having multiple modes of action, [c-35.1] extract from cotyledons of lupin seedlings (BLAD), [c-35.2] extract from Swinglea glutinosa, [c-35.3] Trichoderma atroviride strain I-1237, [c-35.4] Trichoderma atroviride strain LU132, [c-35.5] Trichoderma atroviride strain SC1 strain SC1), [c-35.6] Trichoderma asperellum strain T34, [c-35.7] Gliocladium catenulatum strain J1446, [c-35.8] Clonostachys rosea strain CR-7, [c-35.9] Bacillus amyloliquefaciens strain QST713, [c-35.10] Bacillus amyloliquefaciens FZB24 strain (Bacillus amyloliquefaciens strain FZB24),
  • c-36 Other fungicides> c-36: Other fungicides include, [c-36.1] tecloftalam, [c-36.2] triazoxide, [c-36.3] flusulfamide, [c-36.4] diclomezine, [c-36.5] cyflufenamid, [c -36.6] dodine, [c-36.7] flutianil, [c-36.8] tebufloquin, [c-36.9] validamycins, [c-36.10] cymoxanil, [c-36.11] picarbutrazox, [c -36.12] Quinofumelin, [c-36.13] Aminopyrifen, [c-36.14] Pyridaclomethyl, [c-36.15] Ipflufenoquin, [c-36.16] Florylpicoxamid , [c-36.17] dichlobentiazox, [c-36.18
  • the mixing ratio of the compound of the present invention to the other insecticide or fungicide in a mixture of the compound of the present invention and the other insecticide or fungicide is not particularly limited, but may be, for example, the compound of the present invention:other insecticide or fungicide ratio of 0.01:100-100:0.01, 0.1:100-100:0.1, 1:100-100:1, 1:10-10:1, or 1:1 (all by weight). Furthermore, any combination of these upper and lower limit values is also included as the mixing ratio.
  • the above mixing ratio refers to the ratio of the total value of the other insecticides or fungicides to the compound of the present invention.
  • the compound of the present invention has a remarkable extermination effect against sanitary pests such as Diptera (Culex pipiens, Culex pipiens, midges, house flies, moth flies, horse flies, etc.) and Dictyoptera (Berber's cockroach, Smoky-brown cockroach, American cockroach, etc.).
  • sanitary pests such as Diptera (Culex pipiens, Culex pipiens, midges, house flies, moth flies, horse flies, etc.) and Dictyoptera (Berber's cockroach, Smoky-brown cockroach, American cockroach, etc.).
  • the compound of the present invention can be used as an anthelmintic agent for arthropods that directly harm or arthropods that are vectors of diseases, in the surrounding environment where such harmful organisms may be latent, by spraying, injecting, irrigating, or applying oil solutions, emulsions, wettable powders, etc., spraying powders, etc., treating with heated aerosols such as fumigants, mosquito coils, self-burning type fumigants, chemical reaction type aerosols, fumigants such as fogging, ULV agents, etc., setting granules, tablets, and poison bait, or dropping floating powders, granules, etc. into waterways, wells, reservoirs, water tanks, and other running or standing water.
  • heated aerosols such as fumigants, mosquito coils, self-burning type fumigants, chemical reaction type aerosols, fumigants such as fogging, ULV agents, etc.
  • setting granules, tablets, and poison bait or dropping floating
  • tussock moths for agricultural and forest pests such as tussock moths, it is possible to control them in the same manner as described above, or for flies, etc., a method of mixing the compound in livestock feed so that it mixes with feces, and for mosquitoes, a method of volatilizing the compound into the air using an electric mosquito repellent, etc. are also effective.
  • These formulations for use may also be present as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, and these formulations suitably contain the compound of the present invention in a total amount of, for example, 0.0001% by weight to 95% by weight.
  • the compounds of the present invention can control external or internal parasites of mammals and birds other than humans, such as livestock and pets, including cat fleas, dog fleas, Haemaphysalis longicornis, and nematodes of the family Filariidae.
  • the extermination of external and internal parasites can be achieved by oral administration, parenteral administration or transdermal administration.
  • oral administration a small amount of the compound of the present invention can be mixed into food or feed, or can be prepared into oral administration agents such as suitable orally ingestible compounded pharmaceutical compositions, for example, tablets, pills, capsules, sustained release large pills, pastes, gels, medicated drinks, medicated feed, medicated drinking water, animal feed, medicated follow-up feed, and other sustained release devices that are retained in the gastrointestinal tract, which can be orally administered to livestock and pets.
  • the medicinal drinking water When the compound is orally administered as medicinal drinking water, the medicinal drinking water may be prepared as a solution, suspension or dispersion in a suitable non-toxic solvent or water together with a suspending agent such as bentonite or a wetting agent or other excipients.
  • a suspending agent such as bentonite or a wetting agent or other excipients.
  • medicinal drinking water generally further contains an antifoaming agent.
  • the medicinal drinking water may generally contain the compound of the present invention in an amount of 0.01% by weight to 1.0% by weight, preferably 0.01% by weight to 0.1% by weight.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used.
  • These dose forms are prepared by intimately mixing the active ingredient with a suitable finely divided diluent, filler, disintegrant and/or binder, such as starch, lactose, talc, magnesium stearate, vegetable gums, etc.
  • a suitable finely divided diluent, filler, disintegrant and/or binder such as starch, lactose, talc, magnesium stearate, vegetable gums, etc.
  • Such dry solid unit dose formulations can vary widely in mass and content of anthelmintic agent depending on the type of host animal to be treated, the degree of infection and the type of parasite and the weight of the host.
  • the compound of the invention can be present in the final feed in an amount of, for example, 0.0001% to 0.05% by weight, preferably 0.0005% to 0.01% by weight.
  • Transdermal administration may be by topical or percutaneous administration in the form of a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc.
  • Transdermal or topical administration may also be accomplished by the use of a device (e.g., a collar, medallion, ear tag, etc.) attached to the animal for local or systemic arthropod control.
  • a device e.g., a collar, medallion, ear tag, etc.
  • the compound of the present invention may generally be administered at 0.0001% to 0.1% by weight, preferably 0.001% to 0.01% by weight.
  • the compound dissolved or dispersed in a liquid carrier excipient may be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection.
  • the active compound is preferably mixed with a suitable vegetable oil such as peanut oil or cottonseed oil.
  • a suitable vegetable oil such as peanut oil or cottonseed oil.
  • Such a formulation may generally contain the compound of the present invention at 0.05% to 50% by weight, preferably 0.1% to 5.0% by weight.
  • the compound may also be administered topically by mixing with a suitable carrier such as dimethylsulfoxide or a hydrocarbon solvent.
  • the formulation may be applied directly to the external surface of an animal by spraying or direct pouring.
  • Aqueous sodium thiosulfate solution and ethyl acetate were added to this reaction mixture and the layers were separated.
  • the obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 11.1 mg of the title compound was obtained as a yellow solid.
  • Aqueous sodium thiosulfate solution and ethyl acetate were added to this reaction mixture for separation.
  • the obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 44.0 mg of the title compound was obtained as a white solid.
  • the solvent was distilled off under reduced pressure, and 65.0 ml of pyridine and 6.00 g of 1,2-diamino-4-(trifluoromethyl)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate were added to the resulting solution.
  • the reaction mixture was heated to 80° C. and then stirred for another 6 hours. After cooling to room temperature, 1N aqueous hydrochloric acid and ethyl acetate were added and the mixture was separated. The resulting organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, and dried over sodium sulfate.
  • the solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (2.88 g) as a white solid.
  • the solvent was distilled off under reduced pressure, and 28.6 ml of isobutene (15% tetrahydrofuran solution) and 1.77 ml of triethylamine were added to the residue at 0° C.
  • the reaction mixture was heated to room temperature and stirred for 19 hours. Water and ethyl acetate were added to the reaction mixture and separated the mixture. The organic phase was washed with saline, and dried over magnesium sulfate.
  • the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound was obtained as 1.47 g of a colorless oil.
  • This reaction solution was added to 1.00 ml of a tetrahydrofuran solution containing 60.0 mg of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-amine and 141 ⁇ l of pyridine at 0° C., and stirred for 15 minutes. Water and ethyl acetate were added to this reaction mixture, and the mixture was separated. The organic layer obtained was washed with a saturated aqueous solution of sodium bicarbonate and saline, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 63.1 mg of the title compound was obtained as a white solid.
  • Table 8 shows compounds of the present invention synthesized according to the above examples, but the present invention is not limited to these.
  • Ph represents a phenyl group
  • 2-Py represents a pyridin-2-yl group
  • 3-Py represents a pyridin-3-yl group
  • 4-Py represents a pyridin-4-yl group
  • 1-Pyra represents a 1H-pyrazol-1-yl group
  • 1-Tria represents a 1H-triazol-1-yl group.
  • Structure B shows the following:

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Abstract

The present invention addresses the problem of providing a novel compound for controlling pests. A pyrazole amide compound according to the invention is a novel compound that can control pests. The pyrazole amide compound according to the invention includes a compound represented by formula (1-1) or formula (1-2) and a salt thereof.

Description

ピラゾール化合物およびそれを有効成分とする有害生物防除剤Pyrazole compound and pest control agent containing the same as an active ingredient
　本発明は、ピラゾール化合物およびそれらの塩、並びに該化合物を有効成分として含有することを特徴とする有害生物防除剤または有害節足動物防除剤に関するものである。 The present invention relates to pyrazole compounds and their salts, as well as pest control agents or pest arthropod control agents that contain the compounds as active ingredients.
　安定かつ持続的に農園芸作物を供給する上で、害虫を防除することは極めて重要な役割を果たす。これまでに多種多様な有害生物防除剤の開発が進められ、実用化されてきた。
　しかしながら、近年、このような既存薬剤を長年に渡って使用することにより、薬剤抵抗性を獲得した害虫が多発している。その為、農園芸等の作物生産における被害は、今なお深刻な課題であり、感受性のみならず抵抗性害虫に効果を示す新規剤開発が望まれている。 Controlling pests plays an extremely important role in ensuring a stable and sustainable supply of agricultural and horticultural crops. A wide variety of pest control agents have been developed and put to practical use.
However, in recent years, many pests have developed resistance to these existing pesticides due to their long-term use, and damage to agricultural and horticultural crop production remains a serious issue, making it desirable to develop new pesticides that are effective against not only susceptible pests but also resistant pests.
　ところで、ピラゾール環の３位、または５位に置換アミド基を有するピラゾール化合物は数多く知られている。中でも、イミダゾ［１，２－ａ］ピリジン環、および［１，２，４］トリアゾロ［１，５－ａ］ピリジン環のようなアゾロピリジルピラゾール化合物に着目すると、フォークヘッドタンパク質О１（ＦＯＸＯ１）阻害剤として、芳香族アミド基を持つアゾロピリジルピラゾール化合物が開示されている（例えば、特許文献１参照）。 By the way, many pyrazole compounds having a substituted amide group at the 3rd or 5th position of the pyrazole ring are known. Among them, focusing on azolopyridylpyrazole compounds such as imidazo[1,2-a]pyridine ring and [1,2,4]triazolo[1,5-a]pyridine ring, azolopyridylpyrazole compounds having an aromatic amide group have been disclosed as forkhead protein O1 (FOXO1) inhibitors (see, for example, Patent Document 1).
国際公開第２０２２／０６６９３８号International Publication No. 2022/066938
　特許文献１の明細書に記載されているアゾロピリジルピラゾール化合物は、芳香族アミド基を持つ化合物に限定されている。とりわけ、当該芳香族アミド基として３－クロロ－４－メトキシベンズアミド基を持つアゾロピリジルピラゾール化合物のみが記載されており、脂肪族アミド基やシュウ酸アミド基を持つアゾロピリジルピラゾール化合物は一切開示されていない。また、当該化合物群の用途は、医薬分野に関するものであり、本発明に係る有害生物防除剤または有害節足動物防除剤に属する技術分野とは相違する。 The azolopyridylpyrazole compounds described in the specification of Patent Document 1 are limited to compounds having an aromatic amide group. In particular, only azolopyridylpyrazole compounds having a 3-chloro-4-methoxybenzamide group as the aromatic amide group are described, and azolopyridylpyrazole compounds having an aliphatic amide group or an oxalic acid amide group are not disclosed at all. Furthermore, the uses of this compound group relate to the pharmaceutical field, which differs from the technical field of pest control agents or pest arthropod control agents according to the present invention.
　本発明の課題は、主に農業分野において有害生物または有害節足動物に対して優れた防除効果を有する化合物およびその製造に有用な中間体などを提供することである。 The object of the present invention is to provide compounds that have excellent control effects against harmful organisms or arthropods, mainly in the agricultural field, and intermediates useful for the production of such compounds.
　本発明者らは、前記課題を解決すべく、アゾロピリジルピラゾール化合物に着目し、鋭意検討を行った結果、当該ピラゾール環３位、または５位に、脂肪族アミド置換基等を導入した新規なアゾロピリジルピラゾール化合物群が、有害節足動物に対して優れた防除効果を示すことを見出し、本発明を完成するに至った。 In order to solve the above problems, the inventors focused on azolopyridylpyrazole compounds and conducted extensive research. As a result, they discovered that a novel group of azolopyridylpyrazole compounds in which an aliphatic amide substituent or the like is introduced at the 3rd or 5th position of the pyrazole ring exhibits excellent control effects against harmful arthropods, which led to the completion of the present invention.
　すなわち、本発明は、以下の態様を含む。 In other words, the present invention includes the following aspects:
［１］
　式（１－１）または、式（１－２）
Figure JPOXMLDOC01-appb-C000003
［式中、
Ｒ１は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　置換基Ｂで適宜０～５置換されてもよいフェニル基、
　置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）、
　または１～２個の酸素原子を含む３～６員環の基を表し；  
Ｒ２は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　置換基Ｂで適宜０～５置換されてもよいフェニル基、
　置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）、
　または１～２個の酸素原子を含む３～６員環の基を表し；  
Ｒ３は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
Ｒ４は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
Ｒ５は、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｈｅｔは、式（Ｈｅｔ）を表し；
Figure JPOXMLDOC01-appb-C000004
Ｇは、Ｃ－Ｒ６または窒素原子を表し；
Ｒ６は、
　水素原子、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、     
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　またはＣ２～Ｃ６のハロアルキニル基を表し；
Ｒ７は、
　水素原子、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　またはＣ２～Ｃ６のハロアルキニル基を表し；
Ｒ８は、
　水素原子、
　水酸基、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ９は、
　水素原子、
　水酸基、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ１０は、
　水素原子、
　水酸基、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
置換基Ａは、
　水酸基、
　シアノ基、
　ニトロ基、
　ハロゲン原子、
　Ｃ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　Ｃ３～Ｃ８のシクロアルコキシ基、
　置換基Ｃで適宜０～５置換されてもよいフェニル基、
　置換基Ｃで適宜０～４置換されてもよい５～６員芳香族複素環基、
　および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
置換基Ｂは、
　水酸基、
　シアノ基、
　ニトロ基、
　ハロゲン原子、
　Ｃ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　Ｃ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　Ｃ３～Ｃ８のシクロアルコキシ基、
　およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５は、水酸基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、Ｃ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、ｐは前記と同義である。）からなる群から選択される少なくとも１種であり；
置換基Ｃは、
　シアノ基、
　ハロゲン原子、
　Ｃ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　Ｃ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　Ｃ３～Ｃ８のシクロアルコキシ基、
　およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５およびｐは前記と同義である。）からなる群から独立して選択される少なくとも１種である。］で表される化合物またはその塩。
［２］
Ｒ１は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　またはＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）を表し；
Ｒ２は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　またはＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）を表し；
Ｒ３は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
　または、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
Ｒ４は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
Ｒ５は、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し；
Ｇは、Ｃ－Ｒ６または窒素原子を表し；
Ｒ６は、
　水素原子、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
Ｒ７は、
　水素原子、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
Ｒ８は、
　水素原子、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、     
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ９は、
　水素原子、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ１０は、
　水素原子、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表す［１］に記載の化合物またはその塩。
［３］
Ｒ１は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
Ｒ２は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
Ｒ３は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
　または、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
Ｒ４は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
Ｒ５は、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し；
Ｇは、Ｃ－Ｒ６または窒素原子を表し；
Ｒ６は、
　水素原子、
　ハロゲン原子、
　または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
Ｒ７は、
　水素原子、
　ハロゲン原子、
　または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
Ｒ８は、
　水素原子、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ９は、
　水素原子、
　ハロゲン原子、
　Ｃ１～Ｃ６のハロアルキル基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ１０は、
　水素原子、
　ハロゲン原子、
　またはＣ１～Ｃ６のハロアルキル基を表す［２］に記載の化合物またはその塩。
［４］
Ｒ１は、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
Ｒ２は、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
Ｒ３は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
　または、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
Ｒ４は、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
Ｒ５は、
　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し；
Ｇは、Ｃ－Ｒ６または窒素原子を表し；
Ｒ６は、
　水素原子を表し；
Ｒ７は、
　水素原子を表し；
Ｒ８は、
　水素原子、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　またはＣ１～Ｃ６のハロアルキル基を表し；
Ｒ９は、
　水素原子、
　ハロゲン原子、
　またはＣ１～Ｃ６のハロアルキル基を表し；
Ｒ１０は、
　水素原子を表す［３］に記載の化合物またはその塩。
［５］
　Ｒ１は、メチル基、またはエチル基を表す、[１]～［４］のいずれか一項に記載の化合物またはその塩。
［６］
　Ｒ２は、メチル基、またはエチル基を表す、[１]～［４］、および［５］のいずれか一項に記載の化合物またはその塩。
［７］
　Ｒ３は、水素原子、メチル基、エチル基、アセチル基、シクロプロピオニル基、またはメトキシカルボニル基を表す、[１]～［４］、［５］、および［６］のいずれか一項に記載の化合物またはその塩。
［８］
　Ｒ４は、メチル基、エチル基、プロピル基、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、クロロジフルオロメチル基、ジクロロフルオロメチル基、１，１－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、ヘプタフルオロプロピル基、ノナフルオロブチル基、シクロプロピル基、メトキシ基、ｔ－ブトキシ基、ジメチルカルバモイル基、ジエチルカルバモイル基、または化３中に示されるイソキザゾリン環を表す、[１]～［４］、［５］～［７］のいずれか一項に記載の化合物またはその塩。
Figure JPOXMLDOC01-appb-C000005
［９］
　Ｒ５は、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、イソプロピルスルファニル基、イソプロピルスルフィニル基、またはイソプロピルスルホニル基を表す、[１]～［４］、［５］～［８］のいずれか一項に記載の化合物またはその塩。
［１０］
　Ｇは、窒素原子を表す[１]～［４］、［５］～［９］のいずれか一項に記載の化合物またはその塩。
［１１］
　Ｒ６は、水素原子を表す、[１]～［４］、［５］～［１０］のいずれか一項に記載の化合物またはその塩。
［１２］
　Ｒ７は、水素原子を表す、[１]～［４］、［５］～［１１］のいずれか一項に記載の化合物またはその塩。
［１３］
　Ｒ８は、水素原子、塩素原子、臭素原子、ヨウ素原子、メチル基、またトリフルオロメチル基を表す、[１]～［４］、［５］～［１２］のいずれか一項に記載の化合物またはその塩。
［１４］
　Ｒ９は、水素原子、塩素原子、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、またはヘプタフルオロプロピル基を表す、[１]～［４］、［５］～［１３］のいずれか一項に記載の化合物またはその塩。
［１５］
　Ｒ１０は、水素原子を表す、[１]～［４］、［５］～［１４］のいずれか一項に記載の化合物またはその塩。
［１６］
　［１］～［４］、［５］～［１５］のいずれか一項に記載の化合物またはその塩を有効成分として含有する有害生物防除剤。
［１７］
　有害生物が有害節足動物である、［１６］に記載の有害生物防除剤。
［１８］
　［１６］に記載の有害生物防除剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、有害生物を防除する方法。
［１９］
　有害生物が有害節足動物である、［１８］に記載の有害生物を防除する方法。
［２０］
　有害生物防除剤としての［１］～［４］、［５］～［１５］のいずれか一項に記載の化合物またはその塩の使用。
［２１］
　有害生物が有害節足動物である、［２０］に記載の使用。
［２２］
　有害生物防除剤を調製するための［１］～［４］、［５］～［１５］のいずれか一項に記載の化合物またはその塩の使用。
［２３］
　式（１－３）、または式（１－４）中、
Figure JPOXMLDOC01-appb-C000006
［式中、
Ｒ１は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　置換基Ｂで適宜０～５置換されてもよいフェニル基、
　置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）、
　または１～２個の酸素原子を含む３～６員環の基を表し；  
Ｒ２は、
　水素原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　置換基Ｂで適宜０～５置換されてもよいフェニル基、
　置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、
　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）　、
　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）、
　または１～２個の酸素原子を含む３～６員環の基を表し；  
Ｒ５は、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　Ｃ２～Ｃ６のハロアルキニル基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｈｅｔは、式（Ｈｅｔ）を表し；
Figure JPOXMLDOC01-appb-C000007
Ｇは、Ｃ－Ｒ６または窒素原子を表し；
Ｒ６は、
　水素原子、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、     
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　またはＣ２～Ｃ６のハロアルキニル基を表し；
Ｒ７は、
　水素原子、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　Ｃ２～Ｃ６のハロアルケニル基、
　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　またはＣ２～Ｃ６のハロアルキニル基を表し；
Ｒ８は、
　水素原子、
　水酸基、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ９は、
　水素原子、
　水酸基、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
Ｒ１０は、
　水素原子、
　水酸基、
　シアノ基、
　ハロゲン原子、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
置換基Ａは、
　水酸基、
　シアノ基、
　ニトロ基、
　ハロゲン原子、
　Ｃ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　Ｃ３～Ｃ８のシクロアルコキシ基、
　置換基Ｃで適宜０～５置換されてもよいフェニル基、
　置換基Ｃで適宜０～４置換されてもよい５～６員芳香族複素環基、
　および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
置換基Ｂは、
　水酸基、
　シアノ基、
　ニトロ基、
　ハロゲン原子、
　Ｃ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　Ｃ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　Ｃ３～Ｃ８のシクロアルコキシ基、
　およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５は、水酸基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、Ｃ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、ｐは前記と同義である。）からなる群から選択される少なくとも１種であり；
置換基Ｃは、
　シアノ基、
　ハロゲン原子、
　Ｃ１～Ｃ６のアルキル基、
　Ｃ１～Ｃ６のハロアルキル基、
　Ｃ３～Ｃ８のシクロアルキル基、
　Ｃ１～Ｃ６のアルコキシ基、
　Ｃ１～Ｃ６のハロアルコキシ基、
　Ｃ３～Ｃ８のシクロアルコキシ基、
　およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５およびｐは前記と同義である。）からなる群から独立して選択される少なくとも１種である。］で表される化合物またはその塩。 [1]
Formula (1-1) or Formula (1-2)
Figure JPOXMLDOC01-appb-C000003
[Wherein,
R1 is
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents B;
a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2.),
or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R2 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents B;
a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
Rx3C(=O)- (wherein Rx3 has the same meaning as above),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
Rx4S(O)p- (wherein Rx4 and p are as defined above),
or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R3 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above.)
Rx3C(=O)- (wherein Rx3 has the same meaning as above),
Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
R4 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
Rx3C(=O)- (wherein Rx3 has the same meaning as above),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (provided that when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
R5 is,
Cyano group,
Halogen atoms,
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
Het represents the formula (Het);
Figure JPOXMLDOC01-appb-C000004
G represents C-R6 or a nitrogen atom;
R6 is,
Hydrogen atoms,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
or a C2-C6 haloalkynyl group;
R7 is,
Hydrogen atoms,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
or a C2-C6 haloalkynyl group;
R8 is,
Hydrogen atoms,
Hydroxyl group,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R9 is,
Hydrogen atoms,
Hydroxyl group,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R10 is,
Hydrogen atoms,
Hydroxyl group,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
The substituent A is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atoms,
a C3 to C8 cycloalkyl group,
C1 to C6 alkoxy group,
C1 to C6 haloalkoxy group,
a C3 to C8 cycloalkoxy group,
a phenyl group optionally substituted with 0 to 5 substituents C;
a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents C;
and at least one selected from the group consisting of 3- to 6-membered ring groups containing 1 to 2 oxygen atoms;
The substituent B is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atoms,
C1 to C6 alkyl group,
C1 to C6 haloalkyl groups,
a C3 to C8 cycloalkyl group,
C1 to C6 alkoxy group,
C1 to C6 haloalkoxy group,
a C3 to C8 cycloalkoxy group,
and Rx5S(O)p- (wherein Rx5 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, or a C2-C6 haloalkynyl group, and p is as defined above);
The substituent C is
Cyano group,
Halogen atoms,
C1 to C6 alkyl group,
C1 to C6 haloalkyl groups,
a C3 to C8 cycloalkyl group,
C1 to C6 alkoxy group,
C1 to C6 haloalkoxy group,
a C3 to C8 cycloalkoxy group,
and Rx5S(O)p- (wherein Rx5 and p are as defined above).
[2]
R1 is
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2-C6 alkynyl group optionally substituted by a substituent A;
or Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... a C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group;
R2 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2-C6 alkynyl group optionally substituted by a substituent A;
Or Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above);
R3 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2-C6 alkynyl group optionally substituted by a substituent A;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
R4 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2-C6 alkynyl group optionally substituted by a substituent A;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
Rx3C(=O)- (wherein Rx3 has the same meaning as above),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
R5 is,
Cyano group,
Halogen atoms,
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2);
G represents C-R6 or a nitrogen atom;
R6 is,
Hydrogen atoms,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
R7 is,
Hydrogen atoms,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
R8 is,
Hydrogen atoms,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R9 is,
Hydrogen atoms,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R10 is,
Hydrogen atoms,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
or Rx4S(O)p- (wherein Rx4 and p are as defined above), or a salt thereof.
[3]
R1 is
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
R2 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
R3 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
R4 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
Rx3C(=O)- (wherein Rx3 has the same meaning as above),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
R5 is,
Cyano group,
Halogen atoms,
a C1-C6 alkoxy group optionally substituted with a substituent A;
or Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2);
G represents C-R6 or a nitrogen atom;
R6 is,
Hydrogen atoms,
Halogen atoms,
or a C1-C6 alkyl group optionally substituted with a substituent A;
R7 is,
Hydrogen atoms,
Halogen atoms,
or a C1-C6 alkyl group optionally substituted with a substituent A;
R8 is,
Hydrogen atoms,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
C1 to C6 haloalkoxy group,
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R9 is,
Hydrogen atoms,
Halogen atoms,
C1 to C6 haloalkyl groups,
C1 to C6 haloalkoxy group,
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R10 is,
Hydrogen atoms,
Halogen atoms,
or a salt thereof.
[4]
R1 is
represents a C1-C6 alkyl group optionally substituted with a substituent A;
R2 is,
represents a C1-C6 alkyl group optionally substituted with a substituent A;
R3 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
R4 is,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
R5 is,
Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2);
G represents C-R6 or a nitrogen atom;
R6 is,
represents a hydrogen atom;
R7 is,
represents a hydrogen atom;
R8 is,
Hydrogen atoms,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
or a C1-C6 haloalkyl group;
R9 is,
Hydrogen atoms,
Halogen atoms,
or a C1-C6 haloalkyl group;
R10 is,
The compound or salt thereof according to [3], wherein R represents a hydrogen atom.
[5]
[4], wherein R1 represents a methyl group or an ethyl group. [5], or a salt thereof.
[6]
The compound or salt thereof according to any one of [1] to [4] and [5], wherein R2 represents a methyl group or an ethyl group.
[7]
[0026] R3 represents a hydrogen atom, a methyl group, an ethyl group, an acetyl group, a cyclopropionyl group, or a methoxycarbonyl group; [0027] The compound or salt thereof according to any one of [1] to [4], [5], and [6].
[8]
R4 represents a methyl group, an ethyl group, a propyl group, a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a chlorodifluoromethyl group, a dichlorofluoromethyl group, a 1,1-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a heptafluoropropyl group, a nonafluorobutyl group, a cyclopropyl group, a methoxy group, a t-butoxy group, a dimethylcarbamoyl group, a diethylcarbamoyl group, or an isoxazoline ring shown in Chemical formula 3, or a compound according to any one of [1] to [4] and [5] to [7], or a salt thereof.
Figure JPOXMLDOC01-appb-C000005
[9]
[0036] R5 represents an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, an isopropylsulfanyl group, an isopropylsulfinyl group, or an isopropylsulfonyl group; the compound or salt thereof according to any one of [1] to [4] and [5] to [8].
[10]
The compound or salt thereof according to any one of [1] to [4] and [5] to [9], wherein G represents a nitrogen atom.
[11]
The compound or salt thereof according to any one of [1] to [4] and [5] to [10], wherein R6 represents a hydrogen atom.
[12]
The compound or salt thereof according to any one of [1] to [4] and [5] to [11], wherein R7 represents a hydrogen atom.
[13]
[0033] R8 represents a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, or a trifluoromethyl group; [0034] The compound or salt thereof according to any one of [1] to [4] and [5] to [12].
[14]
[0036] [0037] R9 represents a hydrogen atom, a chlorine atom, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, or a heptafluoropropyl group; [0038] The compound or salt thereof according to any one of [1] to [4] and [5] to [13].
[15]
The compound or salt thereof according to any one of [1] to [4] and [5] to [14], wherein R10 represents a hydrogen atom.
[16]
A pest control agent comprising the compound or a salt thereof according to any one of [1] to [4] and [5] to [15] as an active ingredient.
[17]
The pest control agent according to [16], wherein the pest is an arthropod pest.
[18]
A method for controlling pests, comprising applying the pest control agent according to [16] to a plant, a plant seed, or soil in which a plant is grown.
[19]
The method for controlling pests according to [18], wherein the pests are arthropod pests.
[20]
Use of the compound or a salt thereof according to any one of [1] to [4] and [5] to [15] as a pest control agent.
[21]
The use according to [20], wherein the pest is an arthropod pest.
[22]
Use of the compound or a salt thereof according to any one of [1] to [4] and [5] to [15] for preparing a pesticide.
[23]
In formula (1-3) or formula (1-4),
Figure JPOXMLDOC01-appb-C000006
[Wherein,
R1 is
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents B;
a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2.),
or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R2 is,
Hydrogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 substituents B;
a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B;
Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above),
Rx3C(=O)- (wherein Rx3 has the same meaning as above),
Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
Rx4S(O)p- (wherein Rx4 and p are as defined above),
or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
R5 is,
Cyano group,
Halogen atoms,
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
a C2 to C6 haloalkynyl group,
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
Het represents the formula (Het);
Figure JPOXMLDOC01-appb-C000007
G represents C-R6 or a nitrogen atom;
R6 is,
Hydrogen atoms,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
or a C2-C6 haloalkynyl group;
R7 is,
Hydrogen atoms,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C2-C6 alkenyl group optionally substituted by a substituent A;
a C2 to C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted by a substituent A;
or a C2-C6 haloalkynyl group;
R8 is,
Hydrogen atoms,
Hydroxyl group,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R9 is,
Hydrogen atoms,
Hydroxyl group,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
R10 is,
Hydrogen atoms,
Hydroxyl group,
Cyano group,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with a substituent A;
C1 to C6 haloalkyl groups,
A C3-C8 cycloalkyl group optionally substituted with a substituent A;
a C1-C6 alkoxy group optionally substituted with a substituent A;
C1 to C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
or Rx4S(O)p- (wherein Rx4 and p are as defined above);
The substituent A is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atoms,
a C3 to C8 cycloalkyl group,
C1 to C6 alkoxy group,
C1 to C6 haloalkoxy group,
a C3 to C8 cycloalkoxy group,
a phenyl group optionally substituted with 0 to 5 substituents C;
a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents C;
and at least one selected from the group consisting of 3- to 6-membered ring groups containing 1 to 2 oxygen atoms;
The substituent B is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atoms,
C1 to C6 alkyl group,
C1 to C6 haloalkyl groups,
a C3 to C8 cycloalkyl group,
C1 to C6 alkoxy group,
C1 to C6 haloalkoxy group,
a C3 to C8 cycloalkoxy group,
and Rx5S(O)p- (wherein Rx5 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, or a C2-C6 haloalkynyl group, and p is as defined above);
The substituent C is
Cyano group,
Halogen atoms,
C1 to C6 alkyl group,
C1 to C6 haloalkyl groups,
a C3 to C8 cycloalkyl group,
C1 to C6 alkoxy group,
C1 to C6 haloalkoxy group,
a C3 to C8 cycloalkoxy group,
and Rx5S(O)p- (wherein Rx5 and p are as defined above), or a salt thereof.
　本発明によれば、有害生物防除剤、特に有害節足動物防除剤として有効である新規な化合物を提供することができる。 The present invention provides novel compounds that are effective as pest control agents, particularly as pest control agents for arthropod pests.
　以下、本発明を実施するための形態について詳細に説明する。 The following provides a detailed explanation of how to implement the present invention.
　なお、特許請求の範囲および明細書中において用いられる各用語は、特に断らない限り、当該技術分野において一般的に用いられる定義によるものとする。 In addition, unless otherwise specified, the terms used in the claims and specification shall be defined according to the definitions commonly used in the relevant technical field.
　本明細書において、使用する略号を以下に説明する。 The abbreviations used in this specification are explained below.
　ＤＭＦ：Ｎ，Ｎ－ジメチルホルムアミド、ＴＨＦ：テトラヒドロフラン、Ｍｅ：メチル基、Ｅｔ：エチル基、Ｐｒ：プロピル基、Ｂｕ：ブチル基、Ｐｅｎｔ：ペンチル基、Ｈｅｘ：ヘキシル基、Ｈｅｐｔ：へプチル基、Ｏｃｔ：オクチル基、Ａｃ：アセチル基、Ｐｈ：フェニル基、Ｐｙ：ピリジル基、ｃ：シクロ、ｉ：イソ、ｓｅｃ：セカンダリ、ｔ：ターシャリ、＝：二重結合、≡：三重結合を表す。表のカラム中、Ｐｒ、Ｂｕ、Ｐｅｎｔ、Ｈｅｘに関しては、接頭辞がない場合は、ノルマルを意味する。 DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pent: pentyl group, Hex: hexyl group, Hept: heptyl group, Oct: octyl group, Ac: acetyl group, Ph: phenyl group, Py: pyridyl group, c: cyclo, i: iso, sec: secondary, t: tertiary, =: double bond, ≡: triple bond. In the table columns, Pr, Bu, Pent, and Hex mean normal when there is no prefix.
　以下に、本明細書中に使用される用語の定義を説明する。 The following are definitions of the terms used in this specification.
　Ｃｘ～Ｃｙとの記載は、ｘ個からｙ個の炭素原子を有することを表す。ここで、ｘ及びｙは整数を表し、また、ｘとｙとの間に存在する全ての整数も個別に開示されているものと理解される。例えば、Ｃ１～Ｃ６は、１、２、３、４、５、または６個の炭素原子を、Ｃ２～Ｃ６は、２、３、４、５、または６個の炭素原子を、Ｃ３～Ｃ８は、３、４、５、６、７、または８個の炭素原子を、Ｃ３～Ｃ６は、３、４、５、または６個の炭素原子をそれぞれ有することを意味する。 Cx-Cy means that there are x to y carbon atoms, where x and y are integers, and all integers between x and y are understood to be individually disclosed. For example, C1-C6 means that there are 1, 2, 3, 4, 5, or 6 carbon atoms, C2-C6 means that there are 2, 3, 4, 5, or 6 carbon atoms, C3-C8 means that there are 3, 4, 5, 6, 7, or 8 carbon atoms, and C3-C6 means that there are 3, 4, 5, or 6 carbon atoms.
　用語「適宜置換されてもよい」とは、１つの置換基で置換されるか、または無置換であることを意味する。一方で、例えば、「適宜０～５置換されてもよい」と置換基の数が指定されている場合、０と５との間に存在する全ての整数も個別に開示されているものと理解される。即ち、置換基が、なし、または１、２、３、４、あるいは５個の置換基数であることを意味する。同様に、「適宜０～４置換されてもよい」では、置換基が、なし、または１、２、３、あるいは４個の置換基数をそれぞれ有することを意味する。２置換以上の置換基で構成される場合、置換基はそれぞれ独立した置換基を表し、同一または異なっていてもよい。 The term "optionally substituted" means that it is substituted with one substituent or is unsubstituted. On the other hand, when the number of substituents is specified, for example, "optionally substituted with 0 to 5 substituents," it is understood that all integers between 0 and 5 are also individually disclosed. That is, it means that the number of substituents is none, 1, 2, 3, 4, or 5. Similarly, "optionally substituted with 0 to 4 substituents" means that the number of substituents is none, 1, 2, 3, or 4, respectively. When composed of two or more substituted substituents, each of the substituents represents an independent substituent and may be the same or different.
　ハロゲン原子とは、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられる。 Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.
　Ｃ１～Ｃ６のアルキル基とは、直鎖状または分岐状でよく、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、１，２，２－トリメチルプロピル基等が挙げられる。 The C1 to C6 alkyl group may be linear or branched, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, 1-isopropylpropyl, 1,1,2-trimethylpropyl, and 1,2,2-trimethylpropyl groups.
　Ｃ１～Ｃ６のハロアルキル基とは、前記のＣ１～Ｃ６のアルキル基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ１～Ｃ６のハロアルキル基の具体例として、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、モノクロロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、１，２，２，３，３，４，４，４－オクタフルオロブチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、３，３，４，４，５，５，５－ヘプタフルオロペンチル基、２，３，３，４，４，５，５，５－オクタフルオロペンチル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基、ウンデカフルオロペンチル基、トリデカフルオロヘキシル基等が挙げられる。 A C1-C6 haloalkyl group refers to the above C1-C6 alkyl group in which the hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents. Specific examples of the C1 to C6 haloalkyl group include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoroethyl group, a 4,4-difluoropropyl group, a 5,4-difluoropropyl group, a 6,4-difluoropropyl group, a 7,4-difluoropropyl group, a 8,4-difluoropropyl group, a 9,4-difluoropropyl group, a 10,4-difluoropropyl group, a 11,4-difluoropropyl group, a 12,4-difluoropropyl group, a 13,4-difluoropropyl group, a 14,4-difluoropropyl group, a 15,4-difluoropropyl group, a 16,4-difluoropropyl group, a 17,4-difluoropropyl group, a 18,4-difluoropropyl group, a 19,4-difluoropropyl group, a 21,4-difluoropropyl group, a 22,4-difluoropropyl group, a 23,4-difluoropropyl group, a 24,4-difluoropropyl group, a 25,4-difluoropropyl group, a 26,4-difluoropropyl group, a 27,4 Examples of such groups include trifluoropropyl group, 2,3,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,2,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,2,2,3,3,4,4,4-octafluorobutyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, 2,3,3,4,4,5,5,5-octafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, undecafluoropentyl group, and tridecafluorohexyl group.
　Ｃ３～Ｃ８のシクロアルキル基とは、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基等が挙げられる。 C3 to C8 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.
　Ｃ２～Ｃ６のアルケニル基とは、１個または２個以上の二重結合を有し、直鎖状または分岐状である不飽和炭化水素基のものを表す。また、幾何異性体がある場合、Ｅ体またはＺ体のどちらか一方のみ、あるいはＥ体とＺ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に限定されることはない。Ｃ２～Ｃ６のアルケニル基の具体例として、ビニル基、１－プロペニル基、アリル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、２－メチルアリル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、３－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基、４－メチル－３－ペンテニル基、３－メチル－２－ペンテニル基等が挙げられる。 C2-C6 alkenyl groups refer to unsaturated hydrocarbon groups that have one or more double bonds and are linear or branched. In addition, when there are geometric isomers, they are either the E or Z form alone, or a mixture of the E and Z forms in any ratio, and are not particularly limited as long as they are within the specified carbon number range. Specific examples of C2-C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylallyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 4-methyl-3-pentenyl, and 3-methyl-2-pentenyl.
　Ｃ２～Ｃ６のハロアルケニル基とは、前記のＣ２～Ｃ６のアルケニル基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ２～Ｃ６のハロアルケニル基の具体例として、２－フルオロビニル基、２，２－ジフルオロビニル基、２，２－ジクロロビニル基、３－フルオロアリル基、３，３－ジフルオロアリル基、２，３，３－トリフルオロアリル基、３，３－ジクロロアリル基、４，４－ジフルオロ－３－ブテニル基、５，５－ジフルオロ－４－ペンテニル基、６，６－ジフルオロ－５－ヘキセニル基等が挙げられる。 C2-C6 haloalkenyl group refers to the above C2-C6 alkenyl group in which hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents. Specific examples of C2-C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 2,3,3-trifluoroallyl group, 3,3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, and 6,6-difluoro-5-hexenyl group.
　Ｃ２～Ｃ６のアルキニル基とは、１個または２個以上の三重結合を有し、直鎖状または分岐状である不飽和炭化水素基のものを表す。Ｃ２～Ｃ６のアルキニル基の具体例として、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１，１－ジメチル－２－プロピニル基、１－ヘキシニル基、２－ヘキシニル基、３－ヘキシニル基、４－ヘキシニル基、５－ヘキシニル基等が挙げられる。 C2-C6 alkynyl groups refer to unsaturated hydrocarbon groups that have one or more triple bonds and are linear or branched. Specific examples of C2-C6 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1,1-dimethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, and 5-hexynyl.
　Ｃ２～Ｃ６のハロアルキニル基とは、前記のＣ２～Ｃ６のアルキニル基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ２～Ｃ６のハロアルキニル基の具体例として、２－フルオロエチニル基、２－クロロエチニル基、２－ブロモエチニル基、２－ヨードエチニル基、３，３－ジフルオロ－１－プロピニル基、３－クロロ－３，３－ジフルオロ－１－プロピニル基、３－ブロモ－３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４－クロロ－４，４－ジフルオロ－１－ブチニル基、４－クロロ－４，４－ジフルオロ－２－ブチニル基、４－ブロモ－４，４－ジフルオロ－１－ブチニル基、４－ブロモ－４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、４，４，４－トリフルオロ－２－ブチニル基、５，５－ジフルオロ－３－ペンチニル基、５－クロロ－５，５－ジフルオロ－３－ペンチニル基、５－ブロモ－５，５－ジフルオロ－３－ペンチニル基、５，５，５－トリフルオロ－３－ペンチニル基、６，６－ジフルオロ－４－ヘキシニル基、６－クロロ－６，６－ジフルオロ－４－ヘキシニル基、６－ブロモ－６，６－ジフルオロ－４－ヘキシニル基、６，６，６－トリフルオロ－４－ヘキシニル基等が挙げられる。 A C2-C6 haloalkynyl group refers to the above C2-C6 alkynyl group in which the hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents. Specific examples of C2 to C6 haloalkynyl groups 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, Examples of such groups include 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group, 5,5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro-3-pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, and 6,6,6-trifluoro-4-hexynyl group.
　Ｃ１～Ｃ６のアルコキシ基とは、前記のＣ１～Ｃ６のアルキル基が酸素原子を介して結合したものを表す。Ｃ１～Ｃ６のアルコキシ基として、具体的には、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、ｓｅｃ－ブトキシ基、ｔ－ブトキシ基、ペンチルオキシ基、イソペンチルオキシ基、１－メチルブトキシ基、２－メチルブトキシ基、ネオペンチルオキシ基、１－エチルプロピルオキシ基、１，２－ジメチルプロピルオキシ基、ヘキシルオキシ基、１－メチルペンチルオキシ基、２－メチルペンチルオキシ基、３－メチルペンチルオキシ基、４－メチルペンチルオキシ基、１，１－ジメチルブトキシ基、２，２－ジメチルブトキシ基、３，３－ジメチルブトキシ基、１，２－ジメチルブトキシ基、１，３－ジメチルブトキシ基、２，３－ジメチルブトキシ基、２－エチルブトキシ基、１－イソプロピルプロピルオキシ基、１，１，２－トリメチルプロピルオキシ基、１，２，２－トリメチルプロピルオキシ基等が挙げられる。 A C1 to C6 alkoxy group refers to the above-mentioned C1 to C6 alkyl group bonded via an oxygen atom. Specific examples of C1 to C6 alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropyloxy, 1,2-dimethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, 1-isopropylpropyloxy, 1,1,2-trimethylpropyloxy, and 1,2,2-trimethylpropyloxy groups.
　Ｃ１～Ｃ６のハロアルコキシ基とは、前記のＣ１～Ｃ６のアルコキシ基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ１～Ｃ６のハロアルコキシ基の具体例として、ジフルオロメトキシ基、トリフルオロメトキシ基、クロロジフルオロメトキシ基、ブロモジフルオロメトキシ基、２－フルオロエトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，１，２，２－テトラフルオロエトキシ基、１，２，２，２－テトラフルオロエトキシ基、ペンタフルオロエトキシ基、２，２，２－トリクロロエトキシ基、３，３－ジフルオロプロピルオキシ基、３，３，３－トリフルオロプロピルオキシ基、２，３，３，３－テトラフルオロプロピルオキシ基、２，２，３，３，３－ペンタフルオロプロピルオキシ基、１，２，２，３，３，３－ヘキサフルオロプロピルオキシ基、ヘプタフルオロプロピルオキシ基、ヘプタフルオロイソプロピルオキシ基、２，２，２－トリフルオロ－１－（トリフルオロメチル）－エトキシ基、２，２，３，３，４，４，４－ヘプタフルオロブトキシ基、１，２，２，３，３，４，４，４－オクタフルオロブトキシ基、ノナフルオロブトキシ基、ノナフルオロ－ｓｅｃ－ブトキシ基、３，３，４，４，５，５，５－ヘプタフルオロペンチルオキシ基、２，３，３，４，４，５，５，５－オクタフルオロペンチルオキシ基、２，２，３，３，４，４，５，５，５－ノナフルオロペンチルオキシ基、ウンデカフルオロペンチルオキシ基、トリデカフルオロヘキシルオキシ基等が挙げられる。 A C1-C6 haloalkoxy group refers to an alkoxy group having C1-C6 in which the hydrogen atoms are arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and there is no particular restriction on the number of substitutions as long as they can exist as substituents. Specific examples of C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a pentafluoroethoxy group, a 2,2,2-trichloroethoxy group, a 3,3-difluoropropyloxy group, a 3,3,3-trifluoropropyloxy group, a 2,3,3,3-tetrafluoropropyloxy group, a 2,2,3,3,3-pentafluoropropyloxy group, a 1,2,2,3,3,3-hexafluoropropyloxy group, a ... Examples of such groups include propyloxy, heptafluoropropyloxy, heptafluoroisopropyloxy, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 1,2,2,3,3,4,4,4-octafluorobutoxy, nonafluorobutoxy, nonafluoro-sec-butoxy, 3,3,4,4,5,5,5-heptafluoropentyloxy, 2,3,3,4,4,5,5,5-octafluoropentyloxy, 2,2,3,3,4,4,5,5,5-nonafluoropentyloxy, undecafluoropentyloxy, and tridecafluorohexyloxy.
　Ｃ３～Ｃ８のシクロアルコキシ基とは、前記のＣ３～Ｃ８のシクロアルキル基が酸素原子を介して結合したものを表す。Ｃ３～Ｃ８のシクロアルコキシ基の具体例として、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基等が挙げられる。 C3-C8 cycloalkoxy groups refer to the above-mentioned C3-C8 cycloalkyl groups bonded via an oxygen atom. Specific examples of C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy groups.
　５～６員芳香族複素環基とは、窒素原子、酸素原子および硫黄原子からなる群より選ばれ、少なくとも１つのヘテロ原子を環の構成原子として含む環状芳香族置換基を表す。５～６員芳香族複素環基の具体例として、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、チアジアゾリル基、フリル基、ピロリル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基等が挙げられる。 The term "5- to 6-membered aromatic heterocyclic group" refers to a cyclic aromatic substituent selected from the group consisting of nitrogen, oxygen, and sulfur atoms, and containing at least one heteroatom as a constituent atom of the ring. Specific examples of 5- to 6-membered aromatic heterocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
　５～６員の部分的不飽和ヘテロ環基とは、窒素原子、酸素原子および硫黄原子からなる群より選ばれ、少なくとも１つのヘテロ原子を環の構成原子として含む環状芳香族置換基のうち、一部の結合が部分的に飽和である５～６員のヘテロ環基を表す。ただし、１つ以上の不飽和結合を有する。５～６員の部分的不飽和ヘテロ環基の具体例として、ピロリン環基、ピラゾリン環基、イミダゾリン環基、オキサゾリン環基、チアゾリン環基、イソキサゾリン環基、オキサジン環基、チオオキサジン環基等が挙げられる。 The term "5- to 6-membered partially unsaturated heterocyclic group" refers to a 5- to 6-membered heterocyclic group in which some bonds are partially saturated, among cyclic aromatic substituents containing at least one heteroatom as a ring constituent atom selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. However, it has one or more unsaturated bonds. Specific examples of 5- to 6-membered partially unsaturated heterocyclic groups include a pyrroline ring group, a pyrazoline ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, an isoxazoline ring group, an oxazine ring group, and a thiooxazine ring group.
　８～１０員の部分的不飽和ヘテロ環基とは、窒素原子、酸素原子および硫黄原子からなる群より選ばれ、少なくとも１つのヘテロ原子を環の構成原子として含む環状芳香族置換基のうち、一部の結合が部分的に飽和である８～１０員のヘテロ環基を表す。ただし、１つ以上の不飽和結合を有する。８～１０員の部分的不飽和ヘテロ環基の具体例として、３ａ，５，６，６ａ－テトラヒドロ－４Ｈ－シクロペンタ［ｄ］イソキサゾール環基、３ａ，４，５，６，７，７ａ－ヘキサヒドロベンゾ［ｄ］イソキサゾール環基、３ａ，５，６，７，８，８ａ－ヘキサヒドロ－４Ｈ－シクロヘプタ［ｄ］イソキサゾール環基等が挙げられる。 The term "8- to 10-membered partially unsaturated heterocyclic group" refers to an 8- to 10-membered heterocyclic group in which some bonds are partially saturated, among cyclic aromatic substituents containing at least one heteroatom as a ring constituent atom selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. However, it has one or more unsaturated bonds. Specific examples of 8- to 10-membered partially unsaturated heterocyclic groups include 3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoxazole ring group, 3a,4,5,6,7,7a-hexahydrobenzo[d]isoxazole ring group, and 3a,5,6,7,8,8a-hexahydro-4H-cyclohepta[d]isoxazole ring group.
　１～２個の酸素原子を含む３～６員環の基の具体例として、オキシラニル基、オキセタニル基、オキソラニル基、オキサニル基、１，３－ジオキソラニル基、１，３－ジオキサニル基、１，４－ジオキサニル基、ジヒドロフラン－２（３Ｈ）－オン基、テトラヒドロ－２Ｈ－ピラン－２－オン基等が挙げられる。 Specific examples of 3- to 6-membered ring groups containing 1 or 2 oxygen atoms include oxiranyl, oxetanyl, oxolanyl, oxanyl, 1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, dihydrofuran-2(3H)-one, and tetrahydro-2H-pyran-2-one.
　本発明のピラゾール化合物は、下記式（１―１）、または式（１－２）で表される化合物とその塩を包含する。
Figure JPOXMLDOC01-appb-C000008
 The pyrazole compound of the present invention includes compounds represented by the following formula (1-1) or formula (1-2) and salts thereof.
Figure JPOXMLDOC01-appb-C000008
　以下、式（１―１）、または式（１－２）について説明する。 The following describes formula (1-1) and formula (1-2).
　式（１－１）中のＲ１は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、
置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）、または１～２個の酸素原子を含む３～６員環の基を表す。 R1 in formula (1-1) is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B,
a 5- to 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent A, a C2 to C6 alkenyl group optionally substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy group Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group.), Rx3C(=O)-(where Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B.), Rx3OC(=O)-(wherein and Rx3 has the same meaning as above.), Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2.), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.
　中でもＲ１は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、前記と同義である。）が好ましく、
　特にＲ１は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基が好ましく、
　さらにＲ１は、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基が好ましい。 Among these, R1 is preferably a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above),
In particular, R1 is preferably a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A;
Furthermore, R1 is preferably a C1 to C6 alkyl group which may be appropriately substituted with a substituent A.
　式（１－１）のＲ１には、水素原子が含まれる。 R1 in formula (1-1) includes a hydrogen atom.
　式（１－１）のＲ１における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ペンチル基、またはヘキシル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、またはペンチル基であり、特に好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、またはｓｅｃ－ブチル基である。置換基Ａ記載中の置換基を有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。
「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」として好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ペンチル基、ヘキシル基、シアノメチル基、１－シアノエチル基、２－シアノエチル基、３－シアノプロピル基、２－シアノプロパン－２－イル基、シクロプロピルメチル基、シクロブチルメチル基、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基、イソプロピルオキシメチル基、イソプロピルオキシエチル基、
ベンジル基、１－フェネチル基、２－フェネチル基、４－シアノフェニルメチル基、２－フルオロフェニルメチル基、３－フルオロフェニルメチル基、４－フルオロフェニルメチル基、２－クロロフェニルメチル基、３－クロロフェニルメチル基、３，５－ジクロロフェニルメチル基、４－クロロフェニルメチル基、２－メチルフェニルメチル基、３－メチルフェニルメチル基、４－メチルフェニルメチル基、２－トリフルオロメチルフェニルメチル基、３－トリフルオロメチルフェニルメチル基、４－トリフルオロメチルフェニルメチル基、２－メトキシフェニルメチル基、３－メトキシフェニルメチル基、４－メトキシフェニルメチル基、４－フェノキシフェニルメチル基、４－メタンスルホニルフェニルメチル基、トリフルオロメチルスルファニルフェニルメチル基、
ピリジン－２－イルメチル基、ピリジン－２－イルメチルＮ－オキシド基、３－フルオロピリジン－２－イルメチル基、４－フルオロピリジン－２－イルメチル基、５－フルオロピリジン－２－イルメチル基、６－フルオロピリジン－２－イルメチル基、３－クロロピリジン－２－イルメチル基、４－クロロピリジン－２－イルメチル基、５－クロロピリジン－２－イルメチル基、６－クロロピリジン－２－イルメチル基、３－ブロモピリジン－２－イルメチル基、４－ブロモピリジン－２－イルメチル基、５－ブロモピリジン－２－イルメチル基、６－ブロモピリジン－２－イルメチル基、３－メチルピリジン－２－イルメチル基、４－メチルピリジン－２－イルメチル基、５－メチルピリジン－２－イルメチル基、６－メチルピリジン－２－イルメチル基、３－トリフルオロメチルピリジン－２－イルメチル基、４－トリフルオロメチルピリジン－２－イルメチル基、５－トリフルオロメチルピリジン－２－イルメチル基、６－トリフルオロメチルピリジン－２－イルメチル基、３－シクロプロピルピリジン－２－イルメチル基、４－シクロプロピルピリジン－２－イルメチル基、５－シクロプロピルピリジン－２－イルメチル基、６－シクロプロピルピリジン－２－イルメチル基、３－メトキシピリジン－２－イルメチル基、４－メトキシピリジン－２－イルメチル基、５－メトキシピリジン－２－イルメチル基、６－メトキシピリジン－２－イルメチル基、
ピリジン－３－イルメチル基、２－フルオロピリジン－３－イルメチル基、４－フルオロピリジン－３－イルメチル基、５－フルオロピリジン－３－イルメチル基、６－フルオロピリジン－３－イルメチル基、２－クロロピリジン－３－イルメチル基、４－クロロピリジン－３－イルメチル基、５－クロロピリジン－３－イルメチル基、６－クロロピリジン－３－イルメチル基、２－ブロモピリジン－３－イルメチル基、４－ブロモピリジン－３－イルメチル基、５－ブロモピリジン－３－イルメチル基、６－ブロモピリジン－３－イルメチル基、２－メチルピリジン－３－イルメチル基、４－メチルピリジン－３－イルメチル基、５－メチルピリジン－３－イルメチル基、６－メチルピリジン－３－イルメチル基、２－トリフルオロメチルピリジン－３－イルメチル基、４－トリフルオロメチルピリジン－３－イルメチル基、５－トリフルオロメチルピリジン－３－イルメチル基、６－トリフルオロメチルピリジン－３－イルメチル基、２－メトキシピリジン－３－イルメチル基、４－メトキシピリジン－３－イルメチル基、５－メトキシピリジン－３－イルメチル基、６－メトキシピリジン－３－イルメチル基、
ピリジン－４－イルメチル基、２－フルオロピリジン－４－イルメチル基、３－フルオロピリジン－４－イルメチル基、２－クロロピリジン－４－イルメチル基、３－クロロピリジン－４－イルメチル基、２－ブロモピリジン－４－イルメチル基、３－ブロモピリジン－４－イルメチル基、２－メチルピリジン－４－イルメチル基、３－メチルピリジン－４－イルメチル基、２－トリフルオロメチルピリジン－４－イルメチル基、３－トリフルオロメチルピリジン－４－イルメチル基、２－メトキシピリジン－４－イルメチル基、３－メトキシピリジン－４－イルメチル基、
ピリダジン－３－イルメチル基、４－フルオロピリダジン－３－イルメチル基、５－フルオロピリダジン－３－イルメチル基、６－フルオロピリダジン－３－イルメチル基、４－クロロピリダジン－３－イルメチル基、５－クロロピリダジン－３－イルメチル基、６－クロロピリダジン－３－イルメチル基、４－ブロモピリダジン－３－イルメチル基、５－ブロモピリダジン－３－イルメチル基、６－ブロモピリダジン－３－イルメチル基、４－メチルピリダジン－３－イルメチル基、５－メチルピリダジン－３－イルメチル基、６－メチルピリダジン－３－イルメチル基、４－トリフルオロメチルピリダジン－３－イルメチル基、５－トリフルオロメチルピリダジン－３－イルメチル基、６－トリフルオロメチルピリダジン－３－イルメチル基、４－メトキシピリダジン－３－イルメチル基、５－メトキシピリダジン－３－イルメチル基、６－メトキシピリダジン－３－イルメチル基、
ピリダジン－４－イルメチル基、３－フルオロピリダジン－４－イルメチル基、５－フルオロピリダジン－４－イルメチル基、６－フルオロピリダジン－４－イルメチル基、３－クロロピリダジン－４－イルメチル基、５－クロロピリダジン－４－イルメチル基、６－クロロピリダジン－４－イルメチル基、３－ブロモピリダジン－４－イルメチル基、５－ブロモピリダジン－４－イルメチル基、６－ブロモピリダジン－４－イルメチル基、３－メチルピリダジン－４－イルメチル基、５－メチルピリダジン－４－イルメチル基、６－メチルピリダジン－４－イルメチル基、３－トリフルオロメチルピリダジン－４－イルメチル基、５－トリフルオロメチルピリダジン－４－イルメチル基、６－トリフルオロメチルピリダジン－４－イルメチル基、３－メトキシピリダジン－４－イルメチル基、５－メトキシピリダジン－４－イルメチル基、６－メトキシピリダジン－４－イルメチル基、
ピリミジン－２－イルメチル基、４－フルオロピリミジン－２－イルメチル基、５－フルオロピリミジン－２－イルメチル基、４－クロロピリミジン－２－イルメチル基、５－クロロピリミジン－２－イルメチル基、４－ブロモピリミジン－２－イルメチル基、５－ブロモピリミジン－２－イルメチル基、４－メチルピリミジン－２－イルメチル基、５－メチルピリミジン－２－イルメチル基、４－トリフルオロメチルピリミジン－２－イルメチル基、５－トリフルオロメチルピリミジン－２－イルメチル基、４－メトキシピリミジン－２－イルメチル基、５－メトキシピリミジン－２－イルメチル基、
ピリミジン－４－イルメチル基、２－フルオロピリミジン－４－イルメチル基、５－フルオロピリミジン－４－イルメチル基、６－フルオロピリミジン－４－イルメチル基、２－クロロピリミジン－４－イルメチル基、５－クロロピリミジン－４－イルメチル基、６－クロロピリミジン－４－イルメチル基、２－ブロモピリミジン－４－イルメチル基、５－ブロモピリミジン－４－イルメチル基、６－ブロモピリミジン－４－イルメチル基、２－メチルピリミジン－４－イルメチル基、５－メチルピリミジン－４－イルメチル基、６－メチルピリミジン－４－イルメチル基、２－トリフルオロメチルピリミジン－４－イルメチル基、５－トリフルオロメチルピリミジン－４－イルメチル基、６－トリフルオロメチルピリミジン－４－イルメチル基、２－メトキシピリミジン－４－イルメチル基、５－メトキシピリミジン－４－イルメチル基、６－メトキシピリミジン－４－イルメチル基、
ピリミジン－５－イルメチル基、２－フルオロピリミジン－５－イルメチル基、４－フルオロピリミジン－５－イルメチル基、６－フルオロピリミジン－５－イルメチル基、２－クロロピリミジン－５－イルメチル基、４－クロロピリミジン－５－イルメチル基、６－クロロピリミジン－５－イルメチル基、２－ブロモピリミジン－５－イルメチル基、４－ブロモピリミジン－５－イルメチル基、６－ブロモピリミジン－５－イルメチル基、２－メチルピリミジン－５－イルメチル基、４－メチルピリミジン－５－イルメチル基、６－メチルピリミジン－５－イルメチル基、２－トリフルオロメチルピリミジン－５－イルメチル基、４－トリフルオロメチルピリミジン－５－イルメチル基、６－トリフルオロメチルピリミジン－５－イルメチル基、２－メトキシピリミジン－５－イルメチル基、４－メトキシピリミジン－５－イルメチル基、６－メトキシピリミジン－５－イルメチル基、
ピラジン－２－イルメチル基、３－フルオロピラジン－２－イルメチル基、５－フルオロピラジン－２－イルメチル基、６－フルオロピラジン－２－イルメチル基、３－クロロピラジン－２－イルメチル基、５－クロロピラジン－２－イルメチル基、６－クロロピラジン－２－イルメチル基、３－ブロモピラジン－２－イルメチル基、５－ブロモピラジン－２－イルメチル基、６－ブロモピラジン－２－イルメチル基、３－メチルピラジン－２－イルメチル基、５－メチルピラジン－２－イルメチル基、６－メチルピラジン－２－イルメチル基、３－トリフルオロメチルピラジン－２－イルメチル基、５－トリフルオロメチルピラジン－２－イルメチル基、６－トリフルオロメチルピラジン－２－イルメチル基、３－メトキシピラジン－２－イルメチル基、５－メトキシピラジン－２－イルメチル基、６－メトキシピラジン－２－イルメチル基、
１－（ピリジン－２－イル）エチル基、１－（３－フルオロピリジン－２－イル）エチル基、１－（４－フルオロピリジン－２－イル）エチル基、１－（５－フルオロピリジン－２－イル）エチル基、１－（６－フルオロピリジン－２－イル）エチル基、１－（３－クロロピリジン－２－イル）エチル基、１－（４－クロロピリジン－２－イル）エチル基、１－（５－クロロピリジン－２－イル）エチル基、１－（６－クロロピリジン－２－イル）エチル基、１－（３－ブロモピリジン－２－イル）エチル基、１－（４－ブロモピリジン－２－イル）エチル基、１－（５－ブロモピリジン－２－イル）エチル基、１－（６－ブロモピリジン－２－イル）エチル基、１－（３－メチルピリジン－２－イル）エチル基、１－（４－メチルピリジン－２－イル）エチル基、１－（５－メチルピリジン－２－イル）エチル基、１－（６－メチルピリジン－２－イル）エチル基、１－（３－トリフルオロメチルピリジン－２－イル）エチル基、１－（４－トリフルオロメチルピリジン－２－イル）エチル基、１－（５－トリフルオロメチルピリジン－２－イル）エチル基、１－（６－トリフルオロメチルピリジン－２－イル）エチル基、１－（３－メトキシピリジン－２－イル）エチル基、１－（４－メトキシピリジン－２－イル）エチル基、１－（５－メトキシピリジン－２－イル）エチル基、１－（６－メトキシピリジン－２－イル）エチル基、
１－（ピリジン－３－イル）エチル基、１－（２－フルオロピリジン－３－イル）エチル基、１－（４－フルオロピリジン－３－イル）エチル基、１－（５－フルオロピリジン－３－イル）エチル基、１－（６－フルオロピリジン－３－イル）エチル基、１－（２－クロロピリジン－３－イル）エチル基、１－（４－クロロピリジン－３－イル）エチル基、１－（５－クロロピリジン－３－イル）エチル基、１－（６－クロロピリジン－３－イル）エチル基、１－（２－ブロモピリジン－３－イル）エチル基、１－（４－ブロモピリジン－３－イル）エチル基、１－（５－ブロモピリジン－３－イル）エチル基、１－（６－ブロモピリジン－３－イル）エチル基、１－（２－メチルピリジン－３－イル）エチル基、１－（４－メチルピリジン－３－イル）エチル基、１－（５－メチルピリジン－３－イル）エチル基、１－（６－メチルピリジン－３－イル）エチル基、１－（２－トリフルオロメチルピリジン－３－イル）エチル基、１－（４－トリフルオロメチルピリジン－３－イル）エチル基、１－（５－トリフルオロメチルピリジン－３－イル）エチル基、１－（６－トリフルオロメチルピリジン－３－イル）エチル基、１－（２－メトキシピリジン－３－イル）エチル基、１－（４－メトキシピリジン－３－イル）エチル基、１－（５－メトキシピリジン－３－イル）エチル基、１－（６－メトキシピリジン－３－イル）エチル基、
１－（ピリジン－４－イル）エチル基、１－（２－フルオロピリジン－４－イル）エチル基、１－（３－フルオロピリジン－４－イル）エチル基、１－（２－クロロピリジン－４－イル）エチル基、１－（３－クロロピリジン－４－イル）エチル基、１－（２－ブロモピリジン－４－イル）エチル基、１－（３－ブロモピリジン－４－イル）エチル基、１－（２－メチルピリジン－４－イル）エチル基、１－（３－メチルピリジン－４－イル）エチル基、１－（２－トリフルオロメチルピリジン－４－イル）エチル基、１－（３－トリフルオロメチルピリジン－４－イル）エチル基、１－（２－メトキシピリジン－４－イル）エチル基、１－（３－メトキシピリジン－４－イル）エチル基、
１－（ピリダジン－３－イル）エチル基、１－（４－フルオロピリダジン－３－イル）エチル基、１－（５－フルオロピリダジン－３－イル）エチル基、１－（６－フルオロピリダジン－３－イル）エチル基、１－（４－クロロピリダジン－３－イル）メチル基、１－（５－クロロピリダジン－３－イル）エチル基、１－（６－クロロピリダジン－３－イル）エチル基、１－（４－ブロモピリダジン－３－イル）エチル基、１－（５－ブロモピリダジン－３－イル）エチル基、１－（６－ブロモピリダジン－３－イル）エチル基、１－（４－メチルピリダジン－３－イル）エチル基、１－（５－メチルピリダジン－３－イル）エチル基、１－（６－メチルピリダジン－３－イル）エチル基、１－（４－トリフルオロメチルピリダジン－３－イル）エチル基、１－（５－トリフルオロメチルピリダジン－３－イル）エチル基、１－（６－トリフルオロメチルピリダジン－３－イル）エチル基、１－（４－メトキシピリダジン－３－イル）エチル基、１－（５－メトキシピリダジン－３－イル）エチル基、１－（６－メトキシピリダジン－３－イル）エチル基、
１－（ピリダジン－４－イル）エチル基、１－（３－フルオロピリダジン－４－イル）エチル基、１－（５－フルオロピリダジン－４－イル）エチル基、１－（６－フルオロピリダジン－４－イル）エチル基、１－（３－クロロピリダジン－４－イル）エチル基、１－（５－クロロピリダジン－４－イル）エチル基、１－（６－クロロピリダジン－４－イル）エチル基、１－（３－ブロモピリダジン－４－イル）エチル基、１－（５－ブロモピリダジン－４－イル）エチル基、１－（６－ブロモピリダジン－４－イル）エチル基、１－（３－メチルピリダジン－４－イル）エチル基、１－（５－メチルピリダジン－４－イル）エチル基、１－（６－メチルピリダジン－４－イル）エチル基、１－（３－トリフルオロメチルピリダジン－４－イル）エチル基、１－（５－トリフルオロメチルピリダジン－４－イル）エチル基、１－（６－トリフルオロメチルピリダジン－４－イル）エチル基、１－（３－メトキシピリダジン－４－イル）エチル基、１－（５－メトキシピリダジン－４－イル）エチル基、１－（６－メトキシピリダジン－４－イル）エチル基、
１－（ピリミジン－２－イル）エチル基、１－（４－フルオロピリミジン－２－イル）エチル基、１－（５－フルオロピリミジン－２－イル）エチル基、１－（４－クロロピリミジン－２－イル）エチル基、１－（５－クロロピリミジン－２－イル）エチル基、１－（４－ブロモピリミジン－２－イル）エチル基、１－（５－ブロモピリミジン－２－イル）エチル基、１－（４－メチルピリミジン－２－イル）エチル基、１－（５－メチルピリミジン－２－イル）エチル基、１－（４－トリフルオロメチルピリミジン－２－イル）エチル基、１－（５－トリフルオロメチルピリミジン－２－イル）エチル基、１－（４－メトキシピリミジン－２－イル）エチル基、１－（５－メトキシピリミジン－２－イル）エチル基、
１－（ピリミジン－４－イル）エチル基、１－（２－フルオロピリミジン－４－イル）エチル基、１－（５－フルオロピリミジン－４－イル）エチル基、１－（６－フルオロピリミジン－４－イル）エチル基、１－（２－クロロピリミジン－４－イル）エチル基、１－（５－クロロピリミジン－４－イル）エチル基、１－（６－クロロピリミジン－４－イル）エチル基、１－（２－ブロモピリミジン－４－イル）エチル基、１－（５－ブロモピリミジン－４－イル）エチル基、１－（６－ブロモピリミジン－４－イル）エチル基、１－（２－メチルピリミジン－４－イル）エチル基、１－（５－メチルピリミジン－４－イル）エチル基、１－（６－メチルピリミジン－４－イル）エチル基、１－（２－トリフルオロメチルピリミジン－４－イル）エチル基、１－（５－トリフルオロメチルピリミジン－４－イル）エチル基、１－（６－トリフルオロメチルピリミジン－４－イル）エチル基、１－（２－メトキシピリミジン－４－イル）エチル基、１－（５－メトキシピリミジン－４－イル）エチル基、１－（６－メトキシピリミジン－４－イル）エチル基、
１－（ピリミジン－５－イル）エチル基、１－（２－フルオロピリミジン－５－イル）エチル基、１－（４－フルオロピリミジン－５－イル）エチル基、１－（６－フルオロピリミジン－５－イル）エチル基、１－（２－クロロピリミジン－５－イル）エチル基、１－（４－クロロピリミジン－５－イル）エチル基、１－（６－クロロピリミジン－５－イル）エチル基、１－（２－ブロモピリミジン－５－イル）エチル基、１－（４－ブロモピリミジン－５－イル）エチル基、１－（６－ブロモピリミジン－５－イル）エチル基、１－（２－メチルピリミジン－５－イル）エチル基、１－（４－メチルピリミジン－５－イル）エチル基、１－（６－メチルピリミジン－５－イル）エチル基、１－（２－トリフルオロメチルピリミジン－５－イル）エチル基、１－（４－トリフルオロメチルピリミジン－５－イル）エチル基、１－（６－トリフルオロメチルピリミジン－５－イル）エチル基、１－（２－メトキシピリミジン－５－イル）エチル基、１－（４－メトキシピリミジン－５－イル）エチル基、１－（６－メトキシピリミジン－５－イル）エチル基、
１－（ピラジン－２－イル）エチル基、１－（３－フルオロピラジン－２－イル）エチル基、１－（５－フルオロピラジン－２－イル）エチル基、１－（６－フルオロピラジン－２－イル）エチル基、１－（３－クロロピラジン－２－イル）エチル基、１－（５－クロロピラジン－２－イル）エチル基、１－（６－クロロピラジン－２－イル）エチル基、１－（３－ブロモピラジン－２－イル）エチル基、１－（５－ブロモピラジン－２－イル）エチル基、１－（６－ブロモピラジン－２－イル）エチル基、１－（３－メチルピラジン－２－イル）エチル基、１－（５－メチルピラジン－２－イル）エチル基、１－（６－メチルピラジン－２－イル）エチル基、１－（３－トリフルオロメチルピラジン－２－イル）エチル基、１－（５－トリフルオロメチルピラジン－２－イル）エチル基、１－（６－トリフルオロメチルピラジン－２－イル）エチル基、１－（３－メトキシピラジン－２－イル）エチル基、１―（５－メトキシピラジン－２－イル）エチル基、１－（６－メトキシピラジン－２－イル）エチル基、
３－メチル－１,２,４－オキサジアゾリル基、５－フルオロ－３－メチル－１,２,４－オキサジアゾリル基、５－クロロ－３－メチル－１,２,４－オキサジアゾリル基、５－ブロモ－３－メチル－１,２,４－オキサジアゾリル基、５－メチル－３－メチル－１,２,４－オキサジアゾリル基、５－トリフルオロメチル－３－メチル－１,２,４－オキサジアゾリル基、５－メトキシ－３－メチル－１,２,４－オキサジアゾリル基、チアゾール－２－イルメチル基、チアゾール－４－イルメチル基、チアゾール－５－イルメチル基、
テトラヒドロフラン－２－イルメチル基、テトラヒドロフラン－３－イルメチル基、テトラヒドロ－２Ｈ－ピラン－２－イルメチル基、テトラヒドロ－２Ｈ－ピラン－４－イルメチル基、１，３－ジオキソラン－２－イルメチル基、または３－（ジヒドロフラン－２（３Ｈ）－オン）メチル基であり、
　より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ペンチル基、シアノメチル基、１－シアノエチル基、２－シアノエチル基、シクロプロピルメチル基、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基、イソプロピルオキシメチル基、ベンジル基、１－フェネチル基、２－フェネチル基、４－シアノフェニルメチル基、２－フルオロフェニルメチル基、３－フルオロフェニルメチル基、４－フルオロフェニルメチル基、２－クロロフェニルメチル基、３－クロロフェニルメチル基、３，５－ジクロロフェニルメチル基、４－クロロフェニルメチル基、２－メチルフェニルメチル基、３－メチルフェニルメチル基、４－メチルフェニルメチル基、２－トリフルオロメチルフェニルメチル基、３－トリフルオロメチルフェニルメチル基、４－トリフルオロメチルフェニルメチル基、３－シクロプロピルピリジン－２－イルメチル基、４－シクロプロピルピリジン－２－イルメチル基、５－シクロプロピルピリジン－２－イルメチル基、６－シクロプロピルピリジン－２－イルメチル基、２－メトキシフェニルメチル基、３－メトキシフェニルメチル基、４－メトキシフェニルメチル基、４－フェノキシフェニルメチル基、４－メタンスルホニルフェニルメチル基、４－トリフルオロメチルスルファニルフェニルメチル基、４－トリフルオロスルフィニルフェニルメチル基、４－トリフルオロスルホニルフェニルメチル基、ピリジン－２－イルメチル基、ピリジン－２－イルメチルＮ－オキシド基、３－クロロピリジン－２－イルメチル基、４－クロロピリジン－２－イルメチル基、５－クロロピリジン－２－イルメチル基、６－クロロピリジン－２－イルメチル基、３－ブロモピリジン－２－イルメチル基、４－ブロモピリジン－２－イルメチル基、５－ブロモピリジン－２－イルメチル基、６－ブロモピリジン－２－イルメチル基、３－メチルピリジン－２－イルメチル基、４－メチルピリジン－２－イルメチル基、５－メチルピリジン－２－イルメチル基、６－メチルピリジン－２－イルメチル基、３－トリフルオロメチルピリジン－２－イルメチル基、４－トリフルオロメチルピリジン－２－イルメチル基、５－トリフルオロメチルピリジン－２－イルメチル基、６－トリフルオロメチルピリジン－２－イルメチル基、
３－シクロプロピルピリジン－２－イルメチル基、４－シクロプロピルピリジン－２－イルメチル基、５－シクロプロピルピリジン－２－イルメチル基、６－シクロプロピルピリジン－２－イルメチル基、３－メトキシピリジン－２－イルメチル基、４－メトキシピリジン－２－イルメチル基、５－メトキシピリジン－２－イルメチル基、６－メトキシピリジン－２－イルメチル基、ピリジン－３－イルメチル基、２－クロロピリジン－３－イルメチル基、４－クロロピリジン－３－イルメチル基、５－クロロピリジン－３－イルメチル基、６－クロロピリジン－３－イルメチル基、２－メチルピリジン－３－イルメチル基、４－メチルピリジン－３－イルメチル基、５－メチルピリジン－３－イルメチル基、６－メチルピリジン－３－イルメチル基、２－トリフルオロメチルピリジン－３－イルメチル基、４－トリフルオロメチルピリジン－３－イルメチル基、５－トリフルオロメチルピリジン－３－イルメチル基、６－トリフルオロメチルピリジン－３－イルメチル基、ピリジン－４－イルメチル基、２－クロロピリジン－４－イルメチル基、３－クロロピリジン－４－イルメチル基、２－メチルピリジン－４－イルメチル基、３－メチルピリジン－４－イルメチル基、２－トリフルオロメチルピリジン－４－イルメチル基、３－トリフルオロメチルピリジン－４－イルメチル基、ピリダジン－３－イルメチル基、４－クロロピリダジン－３－イルメチル基、５－クロロピリダジン－３－イルメチル基、６－クロロピリダジン－３－イルメチル基、４－メチルピリダジン－３－イルメチル基、５－メチルピリダジン－３－イルメチル基、６－メチルピリダジン－３－イルメチル基、４－トリフルオロメチルピリダジン－３－イルメチル基、５－トリフルオロメチルピリダジン－３－イルメチル基、６－トリフルオロメチルピリダジン－３－イルメチル基、ピリダジン－４－イルメチル基、３－クロロピリダジン－４－イルメチル基、５－クロロピリダジン－４－イルメチル基、６－クロロピリダジン－４－イルメチル基、３－メチルピリダジン－４－イルメチル基、５－メチルピリダジン－４－イルメチル基、６－メチルピリダジン－４－イルメチル基、３－トリフルオロメチルピリダジン－４－イルメチル基、５－トリフルオロメチルピリダジン－４－イルメチル基、６－トリフルオロメチルピリダジン－４－イルメチル基、３－メトキシピリダジン－４－イルメチル基、ピリミジン－２－イルメチル基、
４－クロロピリミジン－２－イルメチル基、５－クロロピリミジン－２－イルメチル基、４－メチルピリミジン－２－イルメチル基、５－メチルピリミジン－２－イルメチル基、４－トリフルオロメチルピリミジン－２－イルメチル基、５－トリフルオロメチルピリミジン－２－イルメチル基、ピリミジン－４－イルメチル基、２－クロロピリミジン－４－イルメチル基、５－クロロピリミジン－４－イルメチル基、６－クロロピリミジン－４－イルメチル基、２－メチルピリミジン－４－イルメチル基、５－メチルピリミジン－４－イルメチル基、６－メチルピリミジン－４－イルメチル基、２－トリフルオロメチルピリミジン－４－イルメチル基、５－トリフルオロメチルピリミジン－４－イルメチル基、６－トリフルオロメチルピリミジン－４－イルメチル基、ピリミジン－５－イルメチル基、２－クロロピリミジン－５－イルメチル基、４－クロロピリミジン－５－イルメチル基、６－クロロピリミジン－５－イルメチル基、２－メチルピリミジン－５－イルメチル基、４－メチルピリミジン－５－イルメチル基、６－メチルピリミジン－５－イルメチル基、２－トリフルオロメチルピリミジン－５－イルメチル基、４－トリフルオロメチルピリミジン－５－イルメチル基、６－トリフルオロメチルピリミジン－５－イルメチル基、ピラジン－２－イルメチル基、３－クロロピラジン－２－イルメチル基、５－クロロピラジン－２－イルメチル基、６－クロロピラジン－２－イルメチル基、３－メチルピラジン－２－イルメチル基、５－メチルピラジン－２－イルメチル基、６－メチルピラジン－２－イルメチル基、３－トリフルオロメチルピラジン－２－イルメチル基、５－トリフルオロメチルピラジン－２－イルメチル基、６－トリフルオロメチルピラジン－２－イルメチル基、１－（ピリジン－２－イル）エチル基、１－（３－クロロピリジン－２－イル）エチル基、１－（４－クロロピリジン－２－イル）エチル基、１－（５－クロロピリジン－２－イル）エチル基、１－（６－クロロピリジン－２－イル）エチル基、１－（３－メチルピリジン－２－イル）エチル基、１－（４－メチルピリジン－２－イル）エチル基、１－（５－メチルピリジン－２－イル）エチル基、１－（６－メチルピリジン－２－イル）エチル基、１－（３－トリフルオロメチルピリジン－２－イル）エチル基、１－（４－トリフルオロメチルピリジン－２－イル）エチル基、１－（５－トリフルオロメチルピリジン－２－イル）エチル基、１－（６－トリフルオロメチルピリジン－２－イル）エチル基、
１－（ピリジン－３－イル）エチル基、１－（２－クロロピリジン－３－イル）エチル基、１－（４－クロロピリジン－３－イル）エチル基、１－（５－クロロピリジン－３－イル）エチル基、１－（６－クロロピリジン－３－イル）エチル基、１－（２－メチルピリジン－３－イル）エチル基、１－（４－メチルピリジン－３－イル）エチル基、１－（５－メチルピリジン－３－イル）エチル基、１－（６－メチルピリジン－３－イル）エチル基、１－（２－トリフルオロメチルピリジン－３－イル）エチル基、１－（４－トリフルオロメチルピリジン－３－イル）エチル基、１－（５－トリフルオロメチルピリジン－３－イル）エチル基、１－（６－トリフルオロメチルピリジン－３－イル）エチル基、１－（ピリジン－４－イル）エチル基、１－（２－クロロピリジン－４－イル）エチル基、１－（３－クロロピリジン－４－イル）エチル基、１－（２－メチルピリジン－４－イル）エチル基、１－（３－メチルピリジン－４－イル）エチル基、１－（２－トリフルオロメチルピリジン－４－イル）エチル基、１－（３－トリフルオロメチルピリジン－４－イル）エチル基、１－（ピリダジン－３－イル）エチル基、１－（４－クロロピリダジン－３－イル）メチル基、１－（５－クロロピリダジン－３－イル）エチル基、１－（６－クロロピリダジン－３－イル）エチル基、１－（４－メチルピリダジン－３－イル）エチル基、１－（５－メチルピリダジン－３－イル）エチル基、１－（６－メチルピリダジン－３－イル）エチル基、１－（４－トリフルオロメチルピリダジン－３－イル）エチル基、１－（５－トリフルオロメチルピリダジン－３－イル）エチル基、１－（６－トリフルオロメチルピリダジン－３－イル）エチル基、１－（ピリダジン－４－イル）エチル基、１－（３－クロロピリダジン－４－イル）エチル基、１－（５－クロロピリダジン－４－イル）エチル基、１－（６－クロロピリダジン－４－イル）エチル基、１－（３－メチルピリダジン－４－イル）エチル基、１－（５－メチルピリダジン－４－イル）エチル基、１－（６－メチルピリダジン－４－イル）エチル基、１－（３－トリフルオロメチルピリダジン－４－イル）エチル基、１－（５－トリフルオロメチルピリダジン－４－イル）エチル基、１－（６－トリフルオロメチルピリダジン－４－イル）エチル基、１－（ピリミジン－２－イル）エチル基、１－（４－クロロピリミジン－２－イル）エチル基、１－（５－クロロピリミジン－２－イル）エチル基、１－（４－メチルピリミジン－２－イル）エチル基、１－（５－メチルピリミジン－２－イル）エチル基、１－（４－トリフルオロメチルピリミジン－２－イル）エチル基、１－（５－トリフルオロメチルピリミジン－２－イル）エチル基、１－（ピリミジン－４－イル）エチル基、１－（２－クロロピリミジン－４－イル）エチル基、１－（５－クロロピリミジン－４－イル）エチル基、１－（６－クロロピリミジン－４－イル）エチル基、１－（２－メチルピリミジン－４－イル）エチル基、１－（５－メチルピリミジン－４－イル）エチル基、１－（６－メチルピリミジン－４－イル）エチル基、１－（２－トリフルオロメチルピリミジン－４－イル）エチル基、１－（５－トリフルオロメチルピリミジン－４－イル）エチル基、１－（６－トリフルオロメチルピリミジン－４－イル）エチル基、１－（ピリミジン－５－イル）エチル基、１－（２－クロロピリミジン－５－イル）エチル基、１－（４－クロロピリミジン－５－イル）エチル基、１－（６－クロロピリミジン－５－イル）エチル基、１－（２－メチルピリミジン－５－イル）エチル基、１－（４－メチルピリミジン－５－イル）エチル基、１－（６－メチルピリミジン－５－イル）エチル基、１－（２－トリフルオロメチルピリミジン－５－イル）エチル基、１－（４－トリフルオロメチルピリミジン－５－イル）エチル基、１－（６－トリフルオロメチルピリミジン－５－イル）エチル基、１－（ピラジン－２－イル）エチル基、１－（３－クロロピラジン－２－イル）エチル基、１－（５－クロロピラジン－２－イル）エチル基、１－（６－クロロピラジン－２－イル）エチル基、１－（３－メチルピラジン－２－イル）エチル基、１－（５－メチルピラジン－２－イル）エチル基、１－（６－メチルピラジン－２－イル）エチル基、１－（３－トリフルオロメチルピラジン－２－イル）エチル基、１－（５－トリフルオロメチルピラジン－２－イル）エチル基、１－（６－トリフルオロメチルピラジン－２－イル）エチル基、３－メチル－１,２,４－オキサジアゾリル基、５－トリフルオロメチル－３－メチル－１,２,４－オキサジアゾリル基、チアゾール－２－イルメチル基、チアゾール－４－イルメチル基、チアゾール－５－イルメチル基、プロパン－２－オン基、メトキシカルボニルメチル基、メトキシカルボニルエチル基、エトキシカルボニルメチル基、エトキシカルボニルエチル基、ジメチルアミノカルボニルメチル基、エチルメチルアミノカルボニルメチル基、メチルスルファニルメチル基、メチルスルフィニルメチル基、メチルスルホニルメチル基、エチルスルファニルメチル基、エチルスルフィニルメチル基、エチルスルホニルメチル基、トリフルオロメチルスルファニルメチル基、トリフルオロメチルスルフィニルメチル基、トリフルオロスルホニルメチル基、テトラヒドロフラン－２－イルメチル基、テトラヒドロフラン－３－イルメチル基、テトラヒドロ－２Ｈ－ピラン－２－イルメチル基、テトラヒドロ－２Ｈ－ピラン－４－イルメチル基、または１，３－ジオキソラン－２－イルメチル基、３－（ジヒドロフラン－２（３Ｈ）－オン）メチル基であり、
　さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、シアノメチル基、２－シアノエチル基、シクロプロピルメチル基、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基である。
　特に好ましくは、メチル基、またはエチル基である。 The C1-C6 alkyl group in the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a pentyl group, and particularly preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or a sec-butyl group. When the C1-C6 alkyl group has a substituent in the description of the substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent in the description of the substituent A.
Preferred examples of the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, a hexyl group, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a 3-cyanopropyl group, a 2-cyanopropan-2-yl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, an isopropyloxymethyl group, an isopropyloxyethyl group,
benzyl group, 1-phenethyl group, 2-phenethyl group, 4-cyanophenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphenylmethyl group, 3-trifluoromethylphenylmethyl group, 4-trifluoromethylphenylmethyl group, 2-methoxyphenylmethyl group, 3-methoxyphenylmethyl group, 4-methoxyphenylmethyl group, 4-phenoxyphenylmethyl group, 4-methanesulfonylphenylmethyl group, trifluoromethylsulfanylphenylmethyl group,
pyridin-2-ylmethyl group, pyridin-2-ylmethyl N-oxide group, 3-fluoropyridin-2-ylmethyl group, 4-fluoropyridin-2-ylmethyl group, 5-fluoropyridin-2-ylmethyl group, 6-fluoropyridin-2-ylmethyl group, 3-chloropyridin-2-ylmethyl group, 4-chloropyridin-2-ylmethyl group, 5-chloropyridin-2-ylmethyl group, 6-chloropyridin-2-ylmethyl group, 3-bromopyridin-2-ylmethyl group, 4-bromopyridin-2-ylmethyl group, 5-bromopyridin-2-ylmethyl group, 6-bromopyridin-2-ylmethyl group, 3-methylpyridin-2-ylmethyl group, 4-methylpyridin-2-ylmethyl group, 5-methylpyridin-2-ylmethyl group, ethylpyridin-2-ylmethyl group, 6-methylpyridin-2-ylmethyl group, 3-trifluoromethylpyridin-2-ylmethyl group, 4-trifluoromethylpyridin-2-ylmethyl group, 5-trifluoromethylpyridin-2-ylmethyl group, 6-trifluoromethylpyridin-2-ylmethyl group, 3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 3-methoxypyridin-2-ylmethyl group, 4-methoxypyridin-2-ylmethyl group, 5-methoxypyridin-2-ylmethyl group, 6-methoxypyridin-2-ylmethyl group,
pyridin-3-ylmethyl group, 2-fluoropyridin-3-ylmethyl group, 4-fluoropyridin-3-ylmethyl group, 5-fluoropyridin-3-ylmethyl group, 6-fluoropyridin-3-ylmethyl group, 2-chloropyridin-3-ylmethyl group, 4-chloropyridin-3-ylmethyl group, 5-chloropyridin-3-ylmethyl group, 6-chloropyridin-3-ylmethyl group, 2-bromopyridin-3-ylmethyl group, 4-bromopyridin-3-ylmethyl group, 5-bromopyridin-3-ylmethyl group, 6-bromopyridin-3-ylmethyl group, 2-methyl pyridin-3-ylmethyl group, 4-methylpyridin-3-ylmethyl group, 5-methylpyridin-3-ylmethyl group, 6-methylpyridin-3-ylmethyl group, 2-trifluoromethylpyridin-3-ylmethyl group, 4-trifluoromethylpyridin-3-ylmethyl group, 5-trifluoromethylpyridin-3-ylmethyl group, 6-trifluoromethylpyridin-3-ylmethyl group, 2-methoxypyridin-3-ylmethyl group, 4-methoxypyridin-3-ylmethyl group, 5-methoxypyridin-3-ylmethyl group, 6-methoxypyridin-3-ylmethyl group,
pyridin-4-ylmethyl group, 2-fluoropyridin-4-ylmethyl group, 3-fluoropyridin-4-ylmethyl group, 2-chloropyridin-4-ylmethyl group, 3-chloropyridin-4-ylmethyl group, 2-bromopyridin-4-ylmethyl group, 3-bromopyridin-4-ylmethyl group, 2-methylpyridin-4-ylmethyl group, 3-methylpyridin-4-ylmethyl group, 2-trifluoromethylpyridin-4-ylmethyl group, 3-trifluoromethylpyridin-4-ylmethyl group, 2-methoxypyridin-4-ylmethyl group, 3-methoxypyridin-4-ylmethyl group,
pyridazin-3-ylmethyl group, 4-fluoropyridazin-3-ylmethyl group, 5-fluoropyridazin-3-ylmethyl group, 6-fluoropyridazin-3-ylmethyl group, 4-chloropyridazin-3-ylmethyl group, 5-chloropyridazin-3-ylmethyl group, 6-chloropyridazin-3-ylmethyl group, 4-bromopyridazin-3-ylmethyl group, 5-bromopyridazin-3-ylmethyl group, 6-bromopyridazin-3-ylmethyl group, 4 -methylpyridazin-3-ylmethyl group, 5-methylpyridazin-3-ylmethyl group, 6-methylpyridazin-3-ylmethyl group, 4-trifluoromethylpyridazin-3-ylmethyl group, 5-trifluoromethylpyridazin-3-ylmethyl group, 6-trifluoromethylpyridazin-3-ylmethyl group, 4-methoxypyridazin-3-ylmethyl group, 5-methoxypyridazin-3-ylmethyl group, 6-methoxypyridazin-3-ylmethyl group,
pyridazin-4-ylmethyl group, 3-fluoropyridazin-4-ylmethyl group, 5-fluoropyridazin-4-ylmethyl group, 6-fluoropyridazin-4-ylmethyl group, 3-chloropyridazin-4-ylmethyl group, 5-chloropyridazin-4-ylmethyl group, 6-chloropyridazin-4-ylmethyl group, 3-bromopyridazin-4-ylmethyl group, 5-bromopyridazin-4-ylmethyl group, 6-bromopyridazin-4-ylmethyl group, 3 -methylpyridazin-4-ylmethyl group, 5-methylpyridazin-4-ylmethyl group, 6-methylpyridazin-4-ylmethyl group, 3-trifluoromethylpyridazin-4-ylmethyl group, 5-trifluoromethylpyridazin-4-ylmethyl group, 6-trifluoromethylpyridazin-4-ylmethyl group, 3-methoxypyridazin-4-ylmethyl group, 5-methoxypyridazin-4-ylmethyl group, 6-methoxypyridazin-4-ylmethyl group,
pyrimidin-2-ylmethyl group, 4-fluoropyrimidin-2-ylmethyl group, 5-fluoropyrimidin-2-ylmethyl group, 4-chloropyrimidin-2-ylmethyl group, 5-chloropyrimidin-2-ylmethyl group, 4-bromopyrimidin-2-ylmethyl group, 5-bromopyrimidin-2-ylmethyl group, 4-methylpyrimidin-2-ylmethyl group, 5-methylpyrimidin-2-ylmethyl group, 4-trifluoromethylpyrimidin-2-ylmethyl group, 5-trifluoromethylpyrimidin-2-ylmethyl group, 4-methoxypyrimidin-2-ylmethyl group, 5-methoxypyrimidin-2-ylmethyl group,
pyrimidin-4-ylmethyl group, 2-fluoropyrimidin-4-ylmethyl group, 5-fluoropyrimidin-4-ylmethyl group, 6-fluoropyrimidin-4-ylmethyl group, 2-chloropyrimidin-4-ylmethyl group, 5-chloropyrimidin-4-ylmethyl group, 6-chloropyrimidin-4-ylmethyl group, 2-bromopyrimidin-4-ylmethyl group, 5-bromopyrimidin-4-ylmethyl group, 6-bromopyrimidin-4-ylmethyl group, 2 -methylpyrimidin-4-ylmethyl group, 5-methylpyrimidin-4-ylmethyl group, 6-methylpyrimidin-4-ylmethyl group, 2-trifluoromethylpyrimidin-4-ylmethyl group, 5-trifluoromethylpyrimidin-4-ylmethyl group, 6-trifluoromethylpyrimidin-4-ylmethyl group, 2-methoxypyrimidin-4-ylmethyl group, 5-methoxypyrimidin-4-ylmethyl group, 6-methoxypyrimidin-4-ylmethyl group,
pyrimidin-5-ylmethyl group, 2-fluoropyrimidin-5-ylmethyl group, 4-fluoropyrimidin-5-ylmethyl group, 6-fluoropyrimidin-5-ylmethyl group, 2-chloropyrimidin-5-ylmethyl group, 4-chloropyrimidin-5-ylmethyl group, 6-chloropyrimidin-5-ylmethyl group, 2-bromopyrimidin-5-ylmethyl group, 4-bromopyrimidin-5-ylmethyl group, 6-bromopyrimidin-5-ylmethyl group, 2 -methylpyrimidin-5-ylmethyl group, 4-methylpyrimidin-5-ylmethyl group, 6-methylpyrimidin-5-ylmethyl group, 2-trifluoromethylpyrimidin-5-ylmethyl group, 4-trifluoromethylpyrimidin-5-ylmethyl group, 6-trifluoromethylpyrimidin-5-ylmethyl group, 2-methoxypyrimidin-5-ylmethyl group, 4-methoxypyrimidin-5-ylmethyl group, 6-methoxypyrimidin-5-ylmethyl group,
pyrazin-2-ylmethyl group, 3-fluoropyrazin-2-ylmethyl group, 5-fluoropyrazin-2-ylmethyl group, 6-fluoropyrazin-2-ylmethyl group, 3-chloropyrazin-2-ylmethyl group, 5-chloropyrazin-2-ylmethyl group, 6-chloropyrazin-2-ylmethyl group, 3-bromopyrazin-2-ylmethyl group, 5-bromopyrazin-2-ylmethyl group, 6-bromopyrazin-2-ylmethyl group, 3-methylpyrazin-2-ylmethyl group, 5-methylpyrazin-2-ylmethyl group, 6-methylpyrazin-2-ylmethyl group, 3-trifluoromethylpyrazin-2-ylmethyl group, 5-trifluoromethylpyrazin-2-ylmethyl group, 6-trifluoromethylpyrazin-2-ylmethyl group, 3-methoxypyrazin-2-ylmethyl group, 5-methoxypyrazin-2-ylmethyl group, 6-methoxypyrazin-2-ylmethyl group,
1-(pyridin-2-yl)ethyl group, 1-(3-fluoropyridin-2-yl)ethyl group, 1-(4-fluoropyridin-2-yl)ethyl group, 1-(5-fluoropyridin-2-yl)ethyl group, 1-(6-fluoropyridin-2-yl)ethyl group, 1-(3-chloropyridin-2-yl)ethyl group, 1-(4-chloropyridin-2-yl)ethyl group, 1-(5-chloropyridin-2-yl)ethyl group, 1-(6-chloropyridin-2-yl)ethyl group, 1-(3-bromopyridin-2-yl)ethyl group, 1-(4-bromopyridin-2-yl)ethyl group, 1-(5-bromopyridin-2-yl)ethyl group, 1-(6-bromopyridin-2-yl)ethyl group, 1-( 3-methylpyridin-2-yl)ethyl group, 1-(4-methylpyridin-2-yl)ethyl group, 1-(5-methylpyridin-2-yl)ethyl group, 1-(6-methylpyridin-2-yl)ethyl group, 1-(3-trifluoromethylpyridin-2-yl)ethyl group, 1-(4-trifluoromethylpyridin-2-yl)ethyl group, 1-(5-trifluoromethylpyridin-2-yl)ethyl group, 1-(6-trifluoromethylpyridin-2-yl)ethyl group, 1-(3-methoxypyridin-2-yl)ethyl group, 1-(4-methoxypyridin-2-yl)ethyl group, 1-(5-methoxypyridin-2-yl)ethyl group, 1-(6-methoxypyridin-2-yl)ethyl group,
1-(pyridin-3-yl)ethyl group, 1-(2-fluoropyridin-3-yl)ethyl group, 1-(4-fluoropyridin-3-yl)ethyl group, 1-(5-fluoropyridin-3-yl)ethyl group, 1-(6-fluoropyridin-3-yl)ethyl group, 1-(2-chloropyridin-3-yl)ethyl group, 1-(4-chloropyridin-3-yl)ethyl group, 1-(5-chloropyridin-3-yl)ethyl group, 1-(6-chloropyridin-3-yl)ethyl group, 1-(2-bromopyridin-3-yl)ethyl group, 1-(4-bromopyridin-3-yl)ethyl group, 1-(5-bromopyridin-3-yl)ethyl group, 1-(6-bromopyridin-3-yl)ethyl group, 2-methylpyridin-3-yl)ethyl group, 1-(4-methylpyridin-3-yl)ethyl group, 1-(5-methylpyridin-3-yl)ethyl group, 1-(6-methylpyridin-3-yl)ethyl group, 1-(2-trifluoromethylpyridin-3-yl)ethyl group, 1-(4-trifluoromethylpyridin-3-yl)ethyl group, 1-(5-trifluoromethylpyridin-3-yl)ethyl group, 1-(6-trifluoromethylpyridin-3-yl)ethyl group, 1-(2-methoxypyridin-3-yl)ethyl group, 1-(4-methoxypyridin-3-yl)ethyl group, 1-(5-methoxypyridin-3-yl)ethyl group, 1-(6-methoxypyridin-3-yl)ethyl group,
1-(pyridin-4-yl)ethyl group, 1-(2-fluoropyridin-4-yl)ethyl group, 1-(3-fluoropyridin-4-yl)ethyl group, 1-(2-chloropyridin-4-yl)ethyl group, 1-(3-chloropyridin-4-yl)ethyl group, 1-(2-bromopyridin-4-yl)ethyl group, 1-(3-bromopyridin-4-yl)ethyl group, 1-(2-methylpyridin-4-yl)ethyl group, 1-(3-methylpyridin-4-yl)ethyl group, 1-(2-trifluoromethylpyridin-4-yl)ethyl group, 1-(3-trifluoromethylpyridin-4-yl)ethyl group, 1-(2-methoxypyridin-4-yl)ethyl group, 1-(3-methoxypyridin-4-yl)ethyl group,
1-(pyridazin-3-yl)ethyl group, 1-(4-fluoropyridazin-3-yl)ethyl group, 1-(5-fluoropyridazin-3-yl)ethyl group, 1-(6-fluoropyridazin-3-yl)ethyl group, 1-(4-chloropyridazin-3-yl)methyl group, 1-(5-chloropyridazin-3-yl)ethyl group, 1-(6-chloropyridazin-3-yl)ethyl group, 1-(4-bromopyridazin-3-yl)ethyl group, 1-(5-bromopyridazin-3-yl)ethyl group, 1-(6-bromopyridazin-3-yl)ethyl group , 1-(4-methylpyridazin-3-yl)ethyl group, 1-(5-methylpyridazin-3-yl)ethyl group, 1-(6-methylpyridazin-3-yl)ethyl group, 1-(4-trifluoromethylpyridazin-3-yl)ethyl group, 1-(5-trifluoromethylpyridazin-3-yl)ethyl group, 1-(6-trifluoromethylpyridazin-3-yl)ethyl group, 1-(4-methoxypyridazin-3-yl)ethyl group, 1-(5-methoxypyridazin-3-yl)ethyl group, 1-(6-methoxypyridazin-3-yl)ethyl group,
1-(pyridazin-4-yl)ethyl group, 1-(3-fluoropyridazin-4-yl)ethyl group, 1-(5-fluoropyridazin-4-yl)ethyl group, 1-(6-fluoropyridazin-4-yl)ethyl group, 1-(3-chloropyridazin-4-yl)ethyl group, 1-(5-chloropyridazin-4-yl)ethyl group, 1-(6-chloropyridazin-4-yl)ethyl group, 1-(3-bromopyridazin-4-yl)ethyl group, 1-(5-bromopyridazin-4-yl)ethyl group, 1-(6-bromopyridazin-4-yl)ethyl group , 1-(3-methylpyridazin-4-yl)ethyl group, 1-(5-methylpyridazin-4-yl)ethyl group, 1-(6-methylpyridazin-4-yl)ethyl group, 1-(3-trifluoromethylpyridazin-4-yl)ethyl group, 1-(5-trifluoromethylpyridazin-4-yl)ethyl group, 1-(6-trifluoromethylpyridazin-4-yl)ethyl group, 1-(3-methoxypyridazin-4-yl)ethyl group, 1-(5-methoxypyridazin-4-yl)ethyl group, 1-(6-methoxypyridazin-4-yl)ethyl group,
1-(pyrimidin-2-yl)ethyl group, 1-(4-fluoropyrimidin-2-yl)ethyl group, 1-(5-fluoropyrimidin-2-yl)ethyl group, 1-(4-chloropyrimidin-2-yl)ethyl group, 1-(5-chloropyrimidin-2-yl)ethyl group, 1-(4-bromopyrimidin-2-yl)ethyl group, 1-(5-bromopyrimidin-2-yl)ethyl group, 1-(4-methylpyrimidin-2-yl)ethyl group, 1-(5-methylpyrimidin-2-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(4-methoxypyrimidin-2-yl)ethyl group, 1-(5-methoxypyrimidin-2-yl)ethyl group,
1-(pyrimidin-4-yl)ethyl group, 1-(2-fluoropyrimidin-4-yl)ethyl group, 1-(5-fluoropyrimidin-4-yl)ethyl group, 1-(6-fluoropyrimidin-4-yl)ethyl group, 1-(2-chloropyrimidin-4-yl)ethyl group, 1-(5-chloropyrimidin-4-yl)ethyl group, 1-(6-chloropyrimidin-4-yl)ethyl group, 1-(2-bromopyrimidin-4-yl)ethyl group, 1-(5-bromopyrimidin-4-yl)ethyl group, 1-(6-bromopyrimidin-4-yl)ethyl group , 1-(2-methylpyrimidin-4-yl)ethyl group, 1-(5-methylpyrimidin-4-yl)ethyl group, 1-(6-methylpyrimidin-4-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(2-methoxypyrimidin-4-yl)ethyl group, 1-(5-methoxypyrimidin-4-yl)ethyl group, 1-(6-methoxypyrimidin-4-yl)ethyl group,
1-(pyrimidin-5-yl)ethyl group, 1-(2-fluoropyrimidin-5-yl)ethyl group, 1-(4-fluoropyrimidin-5-yl)ethyl group, 1-(6-fluoropyrimidin-5-yl)ethyl group, 1-(2-chloropyrimidin-5-yl)ethyl group, 1-(4-chloropyrimidin-5-yl)ethyl group, 1-(6-chloropyrimidin-5-yl)ethyl group, 1-(2-bromopyrimidin-5-yl)ethyl group, 1-(4-bromopyrimidin-5-yl)ethyl group, 1-(6-bromopyrimidin-5-yl)ethyl group , 1-(2-methylpyrimidin-5-yl)ethyl group, 1-(4-methylpyrimidin-5-yl)ethyl group, 1-(6-methylpyrimidin-5-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(2-methoxypyrimidin-5-yl)ethyl group, 1-(4-methoxypyrimidin-5-yl)ethyl group, 1-(6-methoxypyrimidin-5-yl)ethyl group,
1-(pyrazin-2-yl)ethyl group, 1-(3-fluoropyrazin-2-yl)ethyl group, 1-(5-fluoropyrazin-2-yl)ethyl group, 1-(6-fluoropyrazin-2-yl)ethyl group, 1-(3-chloropyrazin-2-yl)ethyl group, 1-(5-chloropyrazin-2-yl)ethyl group, 1-(6-chloropyrazin-2-yl)ethyl group, 1-(3-bromopyrazin-2-yl)ethyl group, 1-(5-bromopyrazin-2-yl)ethyl group, 1-(6-bromopyrazin-2-yl)ethyl group, 1-(3-methylpyrazin-2-yl)ethyl group, 1-(5-methylpyrazin-2-yl)ethyl group, 1-(6-methylpyrazin-2-yl)ethyl group, 1-(3-trifluoromethylpyrazin-2-yl)ethyl group, 1-(5-trifluoromethylpyrazin-2-yl)ethyl group, 1-(6-trifluoromethylpyrazin-2-yl)ethyl group, 1-(3-methoxypyrazin-2-yl)ethyl group, 1-(5-methoxypyrazin-2-yl)ethyl group, 1-(6-methoxypyrazin-2-yl)ethyl group,
3-methyl-1,2,4-oxadiazolyl group, 5-fluoro-3-methyl-1,2,4-oxadiazolyl group, 5-chloro-3-methyl-1,2,4-oxadiazolyl group, 5-bromo-3-methyl-1,2,4-oxadiazolyl group, 5-methyl-3-methyl-1,2,4-oxadiazolyl group, 5-trifluoromethyl-3-methyl-1,2,4-oxadiazolyl group, 5-methoxy-3-methyl-1,2,4-oxadiazolyl group, thiazol-2-ylmethyl group, thiazol-4-ylmethyl group, thiazol-5-ylmethyl group,
a tetrahydrofuran-2-ylmethyl group, a tetrahydrofuran-3-ylmethyl group, a tetrahydro-2H-pyran-2-ylmethyl group, a tetrahydro-2H-pyran-4-ylmethyl group, a 1,3-dioxolan-2-ylmethyl group, or a 3-(dihydrofuran-2(3H)-one)methyl group;
More preferred are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a cyclopropylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, an isopropyloxymethyl group, a benzyl group, a 1-phenethyl group, a 2-phenethyl group, a 4-cyanophenylmethyl group, a 2-fluorophenylmethyl group, a 3-fluorophenylmethyl group, a 4-fluorophenylmethyl group, a 2-chlorophenylmethyl group, a 3-chlorophenylmethyl group, a 4-chlorophenylmethyl group, a 2 ... chlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphenylmethyl group, 3-trifluoromethylphenylmethyl group, 4-trifluoromethylphenylmethyl group, 3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 2-methoxyphenylmethyl group , 3-methoxyphenylmethyl group, 4-methoxyphenylmethyl group, 4-phenoxyphenylmethyl group, 4-methanesulfonylphenylmethyl group, 4-trifluoromethylsulfanylphenylmethyl group, 4-trifluorosulfinylphenylmethyl group, 4-trifluorosulfonylphenylmethyl group, pyridin-2-ylmethyl group, pyridin-2-ylmethyl N-oxide group, 3-chloropyridin-2-ylmethyl group, 4-chloropyridin-2-ylmethyl group, 5-chloropyridin-2-ylmethyl group, 6-chloropyridin-2-ylmethyl group, 3- bromopyridin-2-ylmethyl group, 4-bromopyridin-2-ylmethyl group, 5-bromopyridin-2-ylmethyl group, 6-bromopyridin-2-ylmethyl group, 3-methylpyridin-2-ylmethyl group, 4-methylpyridin-2-ylmethyl group, 5-methylpyridin-2-ylmethyl group, 6-methylpyridin-2-ylmethyl group, 3-trifluoromethylpyridin-2-ylmethyl group, 4-trifluoromethylpyridin-2-ylmethyl group, 5-trifluoromethylpyridin-2-ylmethyl group, 6-trifluoromethylpyridin-2-ylmethyl group,
3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 3-methoxypyridin-2-ylmethyl group, 4-methoxypyridin-2-ylmethyl group, 5-methoxypyridin-2-ylmethyl group, 6-methoxypyridin-2-ylmethyl group, pyridin-3-ylmethyl group, 2-chloropyridin-3-ylmethyl group, 4-chloropyridin-3-ylmethyl group, 5-chloropyridin-3-ylmethyl group, 6-chloropyridin-3-ylmethyl group group, 2-methylpyridin-3-ylmethyl group, 4-methylpyridin-3-ylmethyl group, 5-methylpyridin-3-ylmethyl group, 6-methylpyridin-3-ylmethyl group, 2-trifluoromethylpyridin-3-ylmethyl group, 4-trifluoromethylpyridin-3-ylmethyl group, 5-trifluoromethylpyridin-3-ylmethyl group, 6-trifluoromethylpyridin-3-ylmethyl group, pyridin-4-ylmethyl group, 2-chloropyridin-4-ylmethyl group, 3-chloropyridin-4-ylmethyl group, 2-methylpyridin-4-ylmethyl group, 3-methylpyridin-4 -ylmethyl group, 2-trifluoromethylpyridin-4-ylmethyl group, 3-trifluoromethylpyridin-4-ylmethyl group, pyridazin-3-ylmethyl group, 4-chloropyridazin-3-ylmethyl group, 5-chloropyridazin-3-ylmethyl group, 6-chloropyridazin-3-ylmethyl group, 4-methylpyridazin-3-ylmethyl group, 5-methylpyridazin-3-ylmethyl group, 6-methylpyridazin-3-ylmethyl group, 4-trifluoromethylpyridazin-3-ylmethyl group, 5-trifluoromethylpyridazin-3-ylmethyl group, 6-trifluoromethylpyridazin-3-ylmethyl group, a pyridazin-3-ylmethyl group, a pyridazin-4-ylmethyl group, a 3-chloropyridazin-4-ylmethyl group, a 5-chloropyridazin-4-ylmethyl group, a 6-chloropyridazin-4-ylmethyl group, a 3-methylpyridazin-4-ylmethyl group, a 5-methylpyridazin-4-ylmethyl group, a 6-methylpyridazin-4-ylmethyl group, a 3-trifluoromethylpyridazin-4-ylmethyl group, a 5-trifluoromethylpyridazin-4-ylmethyl group, a 6-trifluoromethylpyridazin-4-ylmethyl group, a 3-methoxypyridazin-4-ylmethyl group, a pyrimidin-2-ylmethyl group,
4-chloropyrimidin-2-ylmethyl group, 5-chloropyrimidin-2-ylmethyl group, 4-methylpyrimidin-2-ylmethyl group, 5-methylpyrimidin-2-ylmethyl group, 4-trifluoromethylpyrimidin-2-ylmethyl group, 5-trifluoromethylpyrimidin-2-ylmethyl group, pyrimidin-4-ylmethyl group, 2-chloropyrimidin-4-ylmethyl group, 5-chloropyrimidin-4-ylmethyl group, 6-chloropyrimidin-4-ylmethyl group, 2-methylpyrimidin-4-ylmethyl group, 5-methylpyrimidin-4-ylmethyl group, 6-methylpyrimidin-4-ylmethyl group, 2- Trifluoromethylpyrimidin-4-ylmethyl group, 5-trifluoromethylpyrimidin-4-ylmethyl group, 6-trifluoromethylpyrimidin-4-ylmethyl group, pyrimidin-5-ylmethyl group, 2-chloropyrimidin-5-ylmethyl group, 4-chloropyrimidin-5-ylmethyl group, 6-chloropyrimidin-5-ylmethyl group, 2-methylpyrimidin-5-ylmethyl group, 4-methylpyrimidin-5-ylmethyl group, 6-methylpyrimidin-5-ylmethyl group, 2-trifluoromethylpyrimidin-5-ylmethyl group, 4-trifluoromethylpyrimidin-5-ylmethyl group, 6-trifluoromethylpyrimidin-5-ylmethyl group fluoromethylpyrimidin-5-ylmethyl group, pyrazin-2-ylmethyl group, 3-chloropyrazin-2-ylmethyl group, 5-chloropyrazin-2-ylmethyl group, 6-chloropyrazin-2-ylmethyl group, 3-methylpyrazin-2-ylmethyl group, 5-methylpyrazin-2-ylmethyl group, 6-methylpyrazin-2-ylmethyl group, 3-trifluoromethylpyrazin-2-ylmethyl group, 5-trifluoromethylpyrazin-2-ylmethyl group, 6-trifluoromethylpyrazin-2-ylmethyl group, 1-(pyridin-2-yl)ethyl group, 1-(3-chloropyridin-2-yl)ethyl group, 1-(4-chloropyrazin-2-yl)ethyl group, 1-(5-chloropyridin-2-yl)ethyl group, 1-(6-chloropyridin-2-yl)ethyl group, 1-(3-methylpyridin-2-yl)ethyl group, 1-(4-methylpyridin-2-yl)ethyl group, 1-(5-methylpyridin-2-yl)ethyl group, 1-(6-methylpyridin-2-yl)ethyl group, 1-(3-trifluoromethylpyridin-2-yl)ethyl group, 1-(4-trifluoromethylpyridin-2-yl)ethyl group, 1-(5-trifluoromethylpyridin-2-yl)ethyl group, 1-(6-trifluoromethylpyridin-2-yl)ethyl group,
1-(pyridin-3-yl)ethyl group, 1-(2-chloropyridin-3-yl)ethyl group, 1-(4-chloropyridin-3-yl)ethyl group, 1-(5-chloropyridin-3-yl)ethyl group, 1-(6-chloropyridin-3-yl)ethyl group, 1-(2-methylpyridin-3-yl)ethyl group, 1-(4-methylpyridin-3-yl)ethyl group, 1-(5-methylpyridin-3-yl)ethyl group, 1-(6-methylpyridin-3-yl)ethyl group, 1-(2-trifluoromethylpyridin-3-yl)ethyl group, 1-(4-trifluoromethylpyridin-3-yl)ethyl group, 1-(5-trifluoromethylpyridin-3-yl)ethyl group, 1-(6-trifluoromethylpyridin-3-yl)ethyl group, 1-(pyridazin-3-yl)ethyl group, 1-(pyridin-4-yl)ethyl group, 1-(2-chloropyridin-4-yl)ethyl group, 1-(3-chloropyridin-4-yl)ethyl group, 1-(2-methylpyridin-4-yl)ethyl group, 1-(3-methylpyridin-4-yl)ethyl group, 1-(2-trifluoromethylpyridin-4-yl)ethyl group, 1-(3-trifluoromethylpyridin-4-yl)ethyl group, 1-(pyridazin-3-yl)ethyl group, 1-(4-chloropyridazin-3-yl)methyl group, 1-(5-chloropyridazin-3-yl)ethyl group, 1-(6-chloropyridazin-3-yl)ethyl group, 1-(4-methylpyridazin-3-yl)ethyl group ethyl group, 1-(5-methylpyridazin-3-yl)ethyl group, 1-(6-methylpyridazin-3-yl)ethyl group, 1-(4-trifluoromethylpyridazin-3-yl)ethyl group, 1-(5-trifluoromethylpyridazin-3-yl)ethyl group, 1-(6-trifluoromethylpyridazin-3-yl)ethyl group, 1-(pyridazin-4-yl)ethyl group, 1-(3-chloropyridazin-4-yl)ethyl group, 1-(5-chloropyridazin-4-yl)ethyl group, 1-(6-chloropyridazin-4-yl)ethyl group, 1-(3-methylpyridazin-4-yl)ethyl group, 1-(5-methylpyridazin-4-yl)ethyl group, 1-(6-methylpyridazin-4-yl)ethyl group, ethyl group, 1-(3-trifluoromethylpyridazin-4-yl)ethyl group, 1-(5-trifluoromethylpyridazin-4-yl)ethyl group, 1-(6-trifluoromethylpyridazin-4-yl)ethyl group, 1-(pyrimidin-2-yl)ethyl group, 1-(4-chloropyrimidin-2-yl)ethyl group, 1-(5-chloropyrimidin-2-yl)ethyl group, 1-(4-methylpyrimidin-2-yl)ethyl group, 1-(5-methylpyrimidin-2-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(pyrimidin-4-yl)ethyl group, 1-(2-chloropyrimidin 1-(2-methylpyrimidin-4-yl)ethyl group, 1-(5-methylpyrimidin-4-yl)ethyl group, 1-(6-methylpyrimidin-4-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(pyrimidin-5-yl)ethyl group, 1-(2-chloropyrimidin-5-yl)ethyl group, 1-(4-chloropyrimidin-5-yl)ethyl group, 1-(6-chloropyrimidin-4-yl)ethyl group, 1-(2-methylpyrimidin-4-yl)ethyl group, 1-(5-methylpyrimidin-4-yl)ethyl group, 1-(6-methylpyrimidin-4-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(pyrimidin-5-yl)ethyl group, 1-(2-chloropyrimidin-5-yl)ethyl group, 1-(4-chloropyrimidin-5-yl)ethyl group, pyrimidin-5-yl)ethyl group, 1-(2-methylpyrimidin-5-yl)ethyl group, 1-(4-methylpyrimidin-5-yl)ethyl group, 1-(6-methylpyrimidin-5-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(pyrazin-2-yl)ethyl group, 1-(3-chloropyrazin-2-yl)ethyl group, 1-(5-chloropyrazin-2-yl)ethyl group, 1-(6-chloropyrazin-2-yl)ethyl group, 1-(3-methylpyrazin-2-yl)ethyl group, 1-(5-methylpyrazin 1-(6-methylpyrazin-2-yl)ethyl group, 1-(3-trifluoromethylpyrazin-2-yl)ethyl group, 1-(5-trifluoromethylpyrazin-2-yl)ethyl group, 1-(6-trifluoromethylpyrazin-2-yl)ethyl group, 3-methyl-1,2,4-oxadiazolyl group, 5-trifluoromethyl-3-methyl-1,2,4-oxadiazolyl group, thiazol-2-ylmethyl group, thiazol-4-ylmethyl group, thiazol-5-ylmethyl group, propan-2-one group, methoxycarbonylmethyl group, methoxycarbonylethyl group, ethoxycarbonylmethyl group, ethoxycarbonylethyl group, dimethylaminocarbonyl group, a 1,3-dioxolan-2-ylmethyl group, or a 3-(dihydrofuran-2(3H)-one)methyl group;
More preferred are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a cyanomethyl group, a 2-cyanoethyl group, a cyclopropylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, and an ethoxyethyl group.
Particularly preferred is a methyl group or an ethyl group.
　式（１－１）のＲ１における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，２，２，２－テトラフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、２，２，３，３，３－ペンタフルオロプロピル基、１，１，２，２，３，３，３－ヘプタフルオロプロピル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、または２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基であり、さらに好ましくは、ジフルオロメチル基、２，２，２－トリフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、または１，１，２，２，３，３，３－ヘプタフルオロプロピル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、または２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基であり、特に好ましくは、ジフルオロメチル基、２，２，２－トリフルオロエチル基、２，２，３，３，３－ペンタフルオロプロピル基、または２，２，３，３，４，４，４－ヘプタフルオロブチル基である。 The "C1 to C6 haloalkyl group" in R1 of formula (1-1) is defined as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentafluoropropyl group. is preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, and particularly preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, or a 2,2,3,3,4,4,4-heptafluorobutyl group.
　式（１－１）のＲ１における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａに置換される。「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のシクロアルキル基」として好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、１－（シクロプロパン－１－カルボニトリル）基、２－（シクロプロパン－１－カルボニトリル）基、１－（１－ニトロシクロプロピル）基、１－（２－ニトロシクロプロピル）基、１－（１－シクロプロピルシクロプロピル）基、１－（２－シクロプロピルシクロプロピル）基、１－（２－メトキシシクロプロピル）基、１－（２－エトキシシクロプロピル）基、１－（１－フェニルシクロプロピル）基、１－（２－フェニルシクロプロピル）基、１－（シクロプロピルエタン－１－オン）基、２－（シクロプロピルエタン－１オン）基、１－（１－メトキシカルボニルシクロプロピル）基、１－（２－メトキシカルボニルシクロプロピル）基、１－（１－エトキシカルボニルシクロプロピル）基、または１－（２－エトキシカルボニルシクロプロピル）基であり、より好ましくは、シクロプロピル基、シクロブチル基、１－（シクロプロパン－１－カルボニトリル）基、２－（シクロプロパン－１－カルボニトリル）基、１－（１－ニトロシクロプロピル）基、１－（２－ニトロシクロプロピル）基、１－（１－メトキシカルボニルシクロプロピル）基、１－（２－メトキシカルボニルシクロプロピル）基、１－（１－エトキシカルボニルシクロプロピル）基、または１－（２－エトキシカルボニルシクロプロピル）基であり、さらに好ましくは、シクロプロピル基、１－（シクロプロパン－１－カルボニトリル）基、または１－（１－メトキシカルボニルシクロプロピル）基である。特に好ましくは、シクロプロピル基、または１－（シクロプロパン－１－カルボニトリル）基である。 The C3 to C8 cycloalkyl group in the "C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) is as defined above and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with the substituent A. Preferred examples of the "C1 to C6 cycloalkyl group which may be appropriately substituted with a substituent A" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-(cyclopropane-1-carbonitrile) group, a 2-(cyclopropane-1-carbonitrile) group, a 1-(1-nitrocyclopropyl) group, a 1-(2-nitrocyclopropyl) group, a 1-(1-cyclopropylcyclopropyl) group, a 1-(2-cyclopropylcyclopropyl) group, a 1-(2-methoxycyclopropyl) group, a 1-(2-ethoxycyclopropyl) group, a 1-(1-phenylcyclopropyl) group, a 1-(2-phenylcyclopropyl) group, a 1-(cyclopropylethan-1-one) group, a 2-(cyclopropylethan-1-one) group, a 1-(1-methoxycarbonylcyclopropyl) group, a 1-(2-methoxy cyclopropyl) group, 1-(1-ethoxycarbonylcyclopropyl) group, or 1-(2-ethoxycarbonylcyclopropyl) group, more preferably cyclopropyl group, cyclobutyl group, 1-(cyclopropane-1-carbonitrile) group, 2-(cyclopropane-1-carbonitrile) group, 1-(1-nitrocyclopropyl) group, 1-(2-nitrocyclopropyl) group, 1-(1-methoxycarbonylcyclopropyl) group, 1-(2-methoxycarbonylcyclopropyl) group, 1-(1-ethoxycarbonylcyclopropyl) group, or 1-(2-ethoxycarbonylcyclopropyl) group, and even more preferably cyclopropyl group, 1-(cyclopropane-1-carbonitrile) group, or 1-(1-methoxycarbonylcyclopropyl) group. Particularly preferably, it is a cyclopropyl group or a 1-(cyclopropane-1-carbonitrile) group.
　式（１－１）のＲ１における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、または３－ブテニル基であり、特に好ましくは、アリル基、２－メチルアリル基、または３－ブテニル基である。置換基Ａ記載中の置換基を有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) is the same as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group. When it has a substituent as described in the substituent A, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
　式（１－１）のＲ１における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、３，３－ジフルオロアリル基である。 The "C2 to C6 haloalkenyl group" in R1 of formula (1-1) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
　式（１－１）のＲ１における「置換基Ａで適宜置換されてよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、プロパルギル基、または２－ブチニル基であり、特に好ましくは、プロパルギル基、または２－ブチニル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R1 of formula (1-1) is as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（１－１）のＲ１における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、または４，４，４－トリフルオロ－１－ブチニル基であり、特に好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2 to C6 haloalkynyl group" in R1 of formula (1-1) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（１－１）のＲ１における「置換基Ｂで適宜０～５置換されてよいフェニル基」はフェニル基における水素原子が独立した置換基Ｂによって１～５置換の間で任意に置換される。「置換基Ｂで適宜０～５置換されてよいフェニル基」として好ましくは、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、トルイル基、メトキシフェニル基、フェノキシフェニル基、メチルスルファニルフェニル基、メチルスルフィニルフェニル基、メチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、トリフルオロメチルスルフィニルフェニル基、またはトリフルオロメチルスルホニルフェニル基であり、さらに好ましくは、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、トルイル基、メトキシフェニル基、メチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、トリフルオロメチルスルフィニルフェニル基、またはトリフルオロメチルスルホニルフェニル基であり、特に好ましくは、フェニル基である。 The "phenyl group which may be optionally substituted with 0 to 5 substituents B" in R1 of formula (1-1) is a phenyl group in which hydrogen atoms are arbitrarily substituted with 1 to 5 independent substituents B. The "phenyl group which may be optionally substituted with 0 to 5 substituents B" is preferably a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a toluyl group, a methoxyphenyl group, a phenoxyphenyl group, a methylsulfanylphenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, more preferably a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a toluyl group, a methoxyphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, and particularly preferably a phenyl group.
　式（１－１）のＲ１における「置換基Ｂで適宜０～４置換されてよい５～６員芳香族複素環基」の５～６員芳香族複素環基は、前記の定義と同義であり、好ましくは、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基であり、さらに好ましくは、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、チエニル基、チアゾリル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、トリアゾリル基、オキサジアゾリル基であり、特に好ましくは、ピリジル基、またはピリミジニル基である。「置換基Ｂで適宜０～４置換されてよい５～６員芳香族複素環基」として好ましくは、ピリジル基、２－シアノピリジル基、３－シアノピリジル基、４－シアノピリジル基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－ヨードピリジル基、３－ヨードピリジル基、４－ヨードピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリダジニル基、３－シアノピリダジニル基、４－シアノピリダジニル基、３－フルオロピリダジニル基、４－フルオロピリダジニル基、３－クロロピリダジニル基、４－クロロピリダジニル基、３－ブロモピリダジニル基、４－ブロモピリダジニル基、３－ヨードピリダジニル基、４－ヨードピリダジニル基、３－メチルピリダジニル基、４－メチルピリダジニル基、３－トリフルオロメチルピリダジニル基、４－トリフルオロメチルピリダジニル基、３－メトキシピリダジニル基、４－メトキシピリダジニル基、ピリミジニル基、２－シアノピリミジニル基、４－シアノピリミジニル基、５－シアノピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－ブロモピリミジニル基、４－ブロモピリミジニル基、５－ブロモピリミジニル基、２－ヨードピリミジニル基、４－ヨードピリミジニル基、５－ヨードピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、５－メトキシピリミジニル基、ピラジニル基、２－シアノピラジニル基、２－フルオロピラジニル基、２－クロロピラジニル基、２－ブロモピラジニル基、２－ヨードピラジニル基、２－メチルピラジニル基、２－トリフルオロメチルピラジニル基、または２－メトキシピラジニル基であり、
　さらに好ましくは、ピリジル基、２－シアノピリジル基、３－シアノピリジル基、４－シアノピリジル基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－ヨードピリジル基、３－ヨードピリジル基、４－ヨードピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリミジル基、２－シアノピリミジニル基、４－シアノピリミジニル基、５－シアノピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－ブロモピリミジニル基、４－ブロモピリミジニル基、５－ブロモピリミジニル基、２－ヨードピリミジニル基、４－ヨードピリミジニル基、５－ヨードピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、または５－メトキシピリミジニル基であり、
　特に好ましくは、ピリジル基、３－トリフルオロメチルピリジル基、またはピリミジル基である。 The 5- to 6-membered aromatic heterocyclic group of "a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" in R1 of formula (1-1) is the same as defined above, and is preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, or an oxadiazolyl group, and particularly preferably a pyridyl group or a pyrimidinyl group. Preferred examples of the "5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" include a pyridyl group, a 2-cyanopyridyl group, a 3-cyanopyridyl group, a 4-cyanopyridyl group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-iodopyridyl group, a 3-iodopyridyl group, a 4-iodopyridyl group, a 2-methylpyridyl group, a 3-methylpyridyl group, a 4-methylpyridyl group, a 2-trifluoromethylpyridyl group, a pyridyl group, a 3-trifluoromethylpyridyl group, a 4-trifluoromethylpyridyl group, a 2-methoxypyridyl group, a 3-methoxypyridyl group, a 4-methoxypyridyl group, a pyridazinyl group, a 3-cyanopyridazinyl group, a 4-cyanopyridazinyl group, a 3-fluoropyridazinyl group, a 4-fluoropyridazinyl group, a 3-chloropyridazinyl group, a 4-chloropyridazinyl group, a 3-bromopyridazinyl group, a 4-bromopyridazinyl group, a 3-iodopyridazinyl group, a 4-iodopyridazinyl group, a 3-methylpyridazinyl group, a 4-methylpyridazinyl group, a 3-trifluoromethylpyridazinyl group, pyridazinyl group, 4-trifluoromethylpyridazinyl group, 3-methoxypyridazinyl group, 4-methoxypyridazinyl group, pyrimidinyl group, 2-cyanopyrimidinyl group, 4-cyanopyrimidinyl group, 5-cyanopyrimidinyl group, 2-fluoropyrimidinyl group, 4-fluoropyrimidinyl group, 5-fluoropyrimidinyl group, 2-chloropyrimidinyl group, 4-chloropyrimidinyl group, 5-chloropyrimidinyl group, 2-bromopyrimidinyl group, 4-bromopyrimidinyl group, 5-bromopyrimidinyl group, 2-iodopyrimidinyl group, 4-iodopyrimidinyl group, 5-iodopyrimidinyl a 2-methylpyrimidinyl group, a 4-methylpyrimidinyl group, a 5-methylpyrimidinyl group, a 2-trifluoromethylpyrimidinyl group, a 4-trifluoromethylpyrimidinyl group, a 5-trifluoromethylpyrimidinyl group, a 2-methoxypyrimidinyl group, a 4-methoxypyrimidinyl group, a 5-methoxypyrimidinyl group, a pyrazinyl group, a 2-cyanopyrazinyl group, a 2-fluoropyrazinyl group, a 2-chloropyrazinyl group, a 2-bromopyrazinyl group, a 2-iodopyrazinyl group, a 2-methylpyrazinyl group, a 2-trifluoromethylpyrazinyl group, or a 2-methoxypyrazinyl group;
More preferred are pyridyl groups, 2-cyanopyridyl groups, 3-cyanopyridyl groups, 4-cyanopyridyl groups, 2-fluoropyridyl groups, 3-fluoropyridyl groups, 4-fluoropyridyl groups, 2-chloropyridyl groups, 3-chloropyridyl groups, 4-chloropyridyl groups, 2-bromopyridyl groups, 3-bromopyridyl groups, 4-bromopyridyl groups, 2-iodopyridyl groups, 3-iodopyridyl groups, 4-iodopyridyl groups, 2-methylpyridyl groups, 3-methylpyridyl groups, 4-methylpyridyl groups, 2-trifluoromethylpyridyl groups, 3-trifluoromethylpyridyl groups, 4-trifluoromethylpyridyl groups, 2-methoxypyridyl groups, 3-methoxypyridyl groups, 4-methoxypyridyl groups, pyrimidyl groups, 2-cyanopyrimidinyl groups, 4-cyanopyridyl groups, an anopyrimidinyl group, a 5-cyanopyrimidinyl group, a 2-fluoropyrimidinyl group, a 4-fluoropyrimidinyl group, a 5-fluoropyrimidinyl group, a 2-chloropyrimidinyl group, a 4-chloropyrimidinyl group, a 5-chloropyrimidinyl group, a 2-bromopyrimidinyl group, a 4-bromopyrimidinyl group, a 5-bromopyrimidinyl group, a 2-iodopyrimidinyl group, a 4-iodopyrimidinyl group, a 5-iodopyrimidinyl group, a 2-methylpyrimidinyl group, a 4-methylpyrimidinyl group, a 5-methylpyrimidinyl group, a 2-trifluoromethylpyrimidinyl group, a 4-trifluoromethylpyrimidinyl group, a 5-trifluoromethylpyrimidinyl group, a 2-methoxypyrimidinyl group, a 4-methoxypyrimidinyl group, or a 5-methoxypyrimidinyl group;
Particularly preferred is a pyridyl group, a 3-trifluoromethylpyridyl group, or a pyrimidyl group.
　式（１－１）のＲ１におけるＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）の各用語は、前記と同義である。
　「Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－」として好ましくは、カルバモイル基、メチルカルバモイル基、エチルカルバモイル基、プロピルカルバモイル基、イソプロピルカルバモイル基、ブチルカルバモイル基、イソブチルカルバモイル基、ｓｅｃ－ブチルカルバモイル基、ｔ－ブチルカルバモイル基、ペンチルカルバモイル基、イソペンチルカルバモイル基、２－メチルブチルカルバモイル基、ネオペンチルカルバモイル基、１－エチルプロピルカルバモイル基、ヘキシルカルバモイル基、メトキシメチルカルバモイル基、エトキシメチルカルバモイル基、プロピルオキシメチルカルバモイル基、イソプロピルオキシメチルカルバモイル基、２－メトキシエチルカルバモイル基、２－エトキシエチルカルバモイル基、シアノメチルカルバモイル基、１－シアノエチルカルバモイル基、２－シアノエチルカルバモイル基、シクロプロピルメチルカルバモイル基、シクロブチルメチルカルバモイル基、
ベンジルカルバモイル基、１－フェネチルカルバモイル基、１，１－ジフルオロエチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、２，２，２－トリフルオロエチルカルバモイル基、２，２，３，３，３－ペンタフルオロプロピルカルバモイル基、２，２，３，３，４，４，４－ヘプタフルオロブチルカルバモイル基、３，３，４，４，５，５，５－ヘプタフルオロペンチルカルバモイル基、シクロプロピルカルバモイル基、１－シアノシクロプロピルカルバモイル基、アリルカルバモイル基、３，３－ジフルオロアリルカルバモイル基、プロパルギルカルバモイル基、メトキシカルバモイル基、トリフルオロエトキシカルバモイル基、フェニルカルバモイル基、４－シアノフェニルカルバモイル基、２－フルオロフェニルカルバモイル基、３－フルオロフェニルカルバモイル基、４－フルオロフェニルカルバモイル基、２－クロロフェニルカルバモイル基、３－クロロフェニルカルバモイル基、４－クロロフェニルカルバモイル基、２－トリフルオロメチルフェニルカルバモイル基、３－トリフルオロメチルフェニルカルバモイル基、４－トリフルオロメチルフェニルカルバモイル基、２－メトキシフェニルカルバモイル基、３－メトキシフェニルカルバモイル基、４－メトキシフェニルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、
ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、
メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　より好ましくは、メチルカルボニル基、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　さらに好ましくは、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　特に好ましくは、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、イソブチルメチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基である。 Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group which may be optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.) each term has the same meaning as above.
Preferred examples of "Rx1Rx2NC(=O)-" include a carbamoyl group, a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, an isopropylcarbamoyl group, a butylcarbamoyl group, an isobutylcarbamoyl group, a sec-butylcarbamoyl group, a t-butylcarbamoyl group, a pentylcarbamoyl group, an isopentylcarbamoyl group, a 2-methylbutylcarbamoyl group, a neopentylcarbamoyl group, a 1-ethylpropylcarbamoyl group, a hexylcarbamoyl group, a methoxymethylcarbamoyl group, an ethoxymethylcarbamoyl group, a propyloxymethylcarbamoyl group, an isopropyloxymethylcarbamoyl group, a 2-methoxyethylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a cyanomethylcarbamoyl group, a 1-cyanoethylcarbamoyl group, a 2-cyanoethylcarbamoyl group, a cyclopropylmethylcarbamoyl group, a cyclobutylmethylcarbamoyl group,
benzylcarbamoyl group, 1-phenethylcarbamoyl group, 1,1-difluoroethylcarbamoyl group, 2,2-difluoroethylcarbamoyl group, 2,2,2-trifluoroethylcarbamoyl group, 2,2,3,3,3-pentafluoropropylcarbamoyl group, 2,2,3,3,4,4,4-heptafluorobutylcarbamoyl group, 3,3,4,4,5,5,5-heptafluoropentylcarbamoyl group, cyclopropylcarbamoyl group, 1-cyanocyclopropylcarbamoyl group, Allylcarbamoyl group, 3,3-difluoroallylcarbamoyl group, propargylcarbamoyl group, methoxycarbamoyl group, trifluoroethoxycarbamoyl group, phenylcarbamoyl group, 4-cyanophenylcarbamoyl group, 2-fluorophenylcarbamoyl group, 3-fluorophenylcarbamoyl group, 4-fluorophenylcarbamoyl group, 2-chlorophenylcarbamoyl group, 3-chlorophenylcarbamoyl group, 4-chlorophenylcarbamoyl group, 2-trifluoromethyl Phenylcarbamoyl group, 3-trifluoromethylphenylcarbamoyl group, 4-trifluoromethylphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxyphenylcarbamoyl group, pyrrolidinecarbonyl group, piperidinecarbonyl group, piperazinecarbonyl group, morpholinecarbonyl group, thiomorpholinecarbonyl group, dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocane a carbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an ethylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, an isopropylethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, a butylethylcarbamoyl group, a sec-butylmethylcarbamoyl group, a sec-butylethylcarbamoyl group, an isobutylmethylcarbamoyl group, an isobutylethylcarbamoyl group,
t-butylmethylcarbamoyl group, t-butylethylcarbamoyl group, methylpentylcarbamoyl group, ethylpentylcarbamoyl group, isopentylmethylcarbamoyl group, isopentylethylcarbamoyl group, methyl(2-methylbutyl)carbamoyl group, ethyl(2-methylbutyl)carbamoyl group, hexylmethylcarbamoyl group, hexylethylcarbamoyl group, (methoxymethyl)methylcarbamoyl group, (ethoxymethyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, ( (ethoxyethyl)methylcarbamoyl group, (propyloxymethyl)methylcarbamoyl group, (isopropyloxymethyl)methylcarbamoyl group, (methoxymethyl)ethylcarbamoyl group, (ethoxymethyl)ethylcarbamoyl group, (cyanomethyl)methylcarbamoyl group, (cyanomethyl)ethylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pyridin-3-ylmethyl)carbamoyl group, a methyl(2,2,2-trifluoroethyl)carbamoyl group, a methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, a methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, a methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, a (cyclopropyl)methylcarbamoyl group, a (cyclopropyl)ethylcarbamoyl group, a (1-cyanocyclopropyl)methylcarbamoyl group, a (1-cyanocyclopropyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group,
a methyl(6-methyl-pyridin-2-yl)carbamoyl group, a methyl(pyridin-3-yl)carbamoyl group, or a methyl(pyridin-4-yl)carbamoyl group;
More preferably, a methylcarbonyl group, an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a piperazinecarbonyl group, a morpholinecarbonyl group, a thiomorpholinecarbonyl group, a dioxothiomorpholinecarbonyl group, a thiazolidinecarbonyl group, an azepanecarbonyl group, an azocanecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an ethylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, an isopropylethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, a butylethylcarbamoyl group, a sec-butylmethylcarbamoyl group, a sec-butylethylcarbamoyl group, an isobutylmethylcarbamoyl group, a methylcarbamoyl group, an isobutylethylcarbamoyl group, a t-butylmethylcarbamoyl group, a t-butylethylcarbamoyl group, a methylpentylcarbamoyl group, an ethylpentylcarbamoyl group, an isopentylmethylcarbamoyl group, an isopentylethylcarbamoyl group, a methyl(2-methylbutyl)carbamoyl group, an ethyl(2-methylbutyl)carbamoyl group, a hexylmethylcarbamoyl group, a hexylethylcarbamoyl group, a (methoxymethyl)methylcarbamoyl group, an (ethoxymethyl)methylcarbamoyl group, a (methoxyethyl)methylcarbamoyl group, an (ethoxyethyl)methylcarbamoyl group, a (propyloxymethyl)methylcarbamoyl group, an (isopropyloxymethyl)methylcarbamoyl group, a (methoxymethyl)ethylcarbamoyl group, an (ethoxymethyl)methylcarbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopropyl)ethylcarbamoyl group, (1-cyanocyclopropyl)methylcarbamoyl group, methylcarbamoyl group, (1-cyanocyclopropyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group,
More preferred are an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a morpholinecarbonyl group, a thiomorpholinecarbonyl group, a dioxothiomorpholinecarbonyl group, a thiazolidinecarbonyl group, an azepanecarbonyl group, an azocanecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, a butylethylcarbamoyl group, a sec-butylmethylcarbamoyl group, a sec-butylethylcarbamoyl group, an isobutylmethylcarbamoyl group, an isobutylethylcarbamoyl group, a t-butylmethylcarbamoyl group, a (methoxyethyl)methylcarbamoyl group, a (cyanomethyl)methylcarbamoyl group, a (cyanomethyl)ethylcarbamoyl group, and a (cyclopropylmethyl)methylcarbamoyl group. (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pyridin-3-ylmethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (pyridin-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group,
Particularly preferred are an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a morpholinecarbonyl group, a thiomorpholinecarbonyl group, a thiazolidinecarbonyl group, an azepanecarbonyl group, an azocanecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, an isobutylmethylcarbamoyl group, a t-butylmethylcarbamoyl group, a (methoxyethyl)methylcarbamoyl group, a (cyanomethyl)methylcarbamoyl group, and methyl(pyridin-3-yl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group.
　式（１－１）のＲ１における「Ｒｘ３Ｃ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３Ｃ（＝Ｏ）－」として好ましくは、アセチル基、１－シアノアセチル基、１－メトキシアセチル基、プロピオニル基、イソブチリル基、ジフルオロアセチル基、トリフルオロアセチル基、ベンゾイル基、４－フルオロベンゾイル基、または４－トリフルオロベンゾイル基であり、さらに好ましくは、アセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、またはベンゾイル基であり、特に好ましくはアセチル基、トリフルオロアセチル基、またはベンゾイル基である。 Each term in "Rx3C(=O)-" in R1 of formula (1-1) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. "Rx3C(=O)-" is preferably an acetyl group, a 1-cyanoacetyl group, a 1-methoxyacetyl group, a propionyl group, an isobutyryl group, a difluoroacetyl group, a trifluoroacetyl group, a benzoyl group, a 4-fluorobenzoyl group, or a 4-trifluorobenzoyl group, more preferably an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, or a benzoyl group, and particularly preferably an acetyl group, a trifluoroacetyl group, or a benzoyl group.
　式（１－１）のＲ１における「Ｒｘ３ＯＣ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３ＯＣ（＝Ｏ）－」として好ましくは、メトキシカルボニル基、エトキシカルボニル基、イソプロピルオキシカルボニル基、ジフルオロメトキシカルボニル基、トリフルオロメトキシカルボニル基、シクロプロピルオキシカルボニル基、シクロペンチルオキシカルボニル基、アリルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、さらに好ましくは、メトキシカルボニル基、エトキシカルボニル基、イソプロピルオキシカルボニル基、シクロプロピルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、特に好ましくは、メトキシカルボニル基、またはエトキシカルボニル基である。 Each term in "Rx3OC(=O)-" in R1 of formula (1-1) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with substituent A, a C2 to C6 alkenyl group which may be optionally substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. "Rx3OC(=O)-" is preferably a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a cyclopropyloxycarbonyl group, a cyclopentyloxycarbonyl group, an allyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, more preferably a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, a cyclopropyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, and particularly preferably a methoxycarbonyl group or an ethoxycarbonyl group.
　式（１－１）のＲ１における「Ｒｘ４Ｓ（Ｏ）ｐ－」（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）の各用語は、前記の定義と同義である。「Ｒｘ４Ｓ（Ｏ）ｐ－」として好ましくは、メチルスルホニル基、エチルスルホニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルホニル基、シクロペンチルスルホニル基、フェニルスルホニル基、４－フルオロフェニルスルホニル基、４－クロロフェニルスルホニル基、４－メチルフェニルスルホニル基、または４－トリフルオロメチルフェニルスルホニル基であり、さらに好ましくは、メチルスルホニル基、エチルスルホニル基、トリフルオロメチルスルホニル基、４－メチルフェニルスルホニル基、または４－トリフルオロメチルフェニルスルホニル基であり、特に好ましくは、メチルスルホニル基、エチルスルホニル基、または４－メチルフェニルスルホニル基である。 Each term in "Rx4S(O)p-" in R1 of formula (1-1) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) has the same meaning as defined above. "Rx4S(O)p-" is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group, a phenylsulfonyl group, a 4-fluorophenylsulfonyl group, a 4-chlorophenylsulfonyl group, a 4-methylphenylsulfonyl group, or a 4-trifluoromethylphenylsulfonyl group, more preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 4-methylphenylsulfonyl group, or a 4-trifluoromethylphenylsulfonyl group, and particularly preferably a methylsulfonyl group, an ethylsulfonyl group, or a 4-methylphenylsulfonyl group.
　式（１－１）のＲ１における「１～２個の酸素原子を含む３～６員環の基」の用語は、前記と同義である。「１～２個の酸素原子を含む３～６員環の基」として好ましくは、オキシラン－２－イル基、オキセタン－３－イル基、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、１，４－ジオキサン－２－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、４－ジヒドロフラン－２（３Ｈ）－オン基、３－テトラヒドロ－２Ｈ－ピラン－２－オン基、または４－テトラヒドロ－２Ｈ－ピラン－２－オン基であり、より好ましくは、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、または４－ジヒドロフラン－２（３Ｈ）－オン基であり、さらに好ましくは、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、または３－ジヒドロフラン－２（３Ｈ）－オン基であり、特に好ましくは、テトラヒドロ－２Ｈ－ピラン－４－イル基、または３－ジヒドロフラン－２（３Ｈ）－オン基である。 The term "3- to 6-membered ring group containing 1 to 2 oxygen atoms" in R1 of formula (1-1) has the same meaning as above. The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" is preferably an oxiran-2-yl group, an oxetan-3-yl group, a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 1,4-dioxan-2-yl group, a 3-dihydrofuran-2(3H)-one group, a 4-dihydrofuran-2(3H)-one group, a 3-tetrahydro-2H-pyran-2-one group, or a 4-tetrahydro-2H-pyran-2-one group, and more preferably a tetrahydro It is preferably a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 3-dihydrofuran-2(3H)-one group, or a 4-dihydrofuran-2(3H)-one group, more preferably a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-4-yl group, or a 3-dihydrofuran-2(3H)-one group, and particularly preferably a tetrahydro-2H-pyran-4-yl group, or a 3-dihydrofuran-2(3H)-one group.
　式（１－２）中のＲ２は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）、または１～２個の酸素原子を含む３～６員環の基を表す。 R2 in formula (1-2) is a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C group which may be optionally substituted with a substituent A, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, represent an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group optionally substituted with 0 to 5 substituents B, or a 5- to 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B; or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, represent an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a cycloalkoxy group, a phenyl group optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B, represents a group that forms a phenyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group; Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be appropriately substituted with 0 to 5 substituents B, or represents a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B. ), Rx3OC(=O)- (wherein Rx3 has the same meaning as above), Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2. ), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.
　中でもＲ２は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）が好ましく、 Among them, R2 is preferably a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above),
　特にＲ２は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基が好ましく、
　さらにＲ２は、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基が好ましい。 In particular, R2 is preferably a hydrogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A;
Furthermore, R2 is preferably a C1 to C6 alkyl group which may be appropriately substituted with a substituent A.
　式（１－２）のＲ２には、水素原子が含まれる。 R2 in formula (1-2) includes a hydrogen atom.
　式（１－２）のＲ２における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ペンチル基、またはヘキシル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、またはペンチル基であり、特に好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、またはｓｅｃ－ブチル基である。置換基Ａ記載中の置換基を有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。
「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」として好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ペンチル基、ヘキシル基、シアノメチル基、１－シアノエチル基、２－シアノエチル基、３－シアノプロピル基、２－シアノプロパン－２－イル基、シクロプロピルメチル基、シクロブチルメチル基、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基、イソプロピルオキシメチル基、イソプロピルオキシエチル基、
ベンジル基、１－フェネチル基、２－フェネチル基、４－シアノフェニルメチル基、２－フルオロフェニルメチル基、３－フルオロフェニルメチル基、４－フルオロフェニルメチル基、２－クロロフェニルメチル基、３－クロロフェニルメチル基、３，５－ジクロロフェニルメチル基、４－クロロフェニルメチル基、２－メチルフェニルメチル基、３－メチルフェニルメチル基、４－メチルフェニルメチル基、２－トリフルオロメチルフェニルメチル基、３－トリフルオロメチルフェニルメチル基、４－トリフルオロメチルフェニルメチル基、２－メトキシフェニルメチル基、３－メトキシフェニルメチル基、４－メトキシフェニルメチル基、４－フェノキシフェニルメチル基、４－メタンスルホニルフェニルメチル基、トリフルオロメチルスルファニルフェニルメチル基、
ピリジン－２－イルメチル基、ピリジン－２－イルメチルＮ－オキシド基、３－フルオロピリジン－２－イルメチル基、４－フルオロピリジン－２－イルメチル基、５－フルオロピリジン－２－イルメチル基、６－フルオロピリジン－２－イルメチル基、３－クロロピリジン－２－イルメチル基、４－クロロピリジン－２－イルメチル基、５－クロロピリジン－２－イルメチル基、６－クロロピリジン－２－イルメチル基、３－ブロモピリジン－２－イルメチル基、４－ブロモピリジン－２－イルメチル基、５－ブロモピリジン－２－イルメチル基、６－ブロモピリジン－２－イルメチル基、３－メチルピリジン－２－イルメチル基、４－メチルピリジン－２－イルメチル基、５－メチルピリジン－２－イルメチル基、６－メチルピリジン－２－イルメチル基、３－トリフルオロメチルピリジン－２－イルメチル基、４－トリフルオロメチルピリジン－２－イルメチル基、５－トリフルオロメチルピリジン－２－イルメチル基、６－トリフルオロメチルピリジン－２－イルメチル基、３－シクロプロピルピリジン－２－イルメチル基、４－シクロプロピルピリジン－２－イルメチル基、５－シクロプロピルピリジン－２－イルメチル基、６－シクロプロピルピリジン－２－イルメチル基、３－メトキシピリジン－２－イルメチル基、４－メトキシピリジン－２－イルメチル基、５－メトキシピリジン－２－イルメチル基、６－メトキシピリジン－２－イルメチル基、
ピリジン－３－イルメチル基、２－フルオロピリジン－３－イルメチル基、４－フルオロピリジン－３－イルメチル基、５－フルオロピリジン－３－イルメチル基、６－フルオロピリジン－３－イルメチル基、２－クロロピリジン－３－イルメチル基、４－クロロピリジン－３－イルメチル基、５－クロロピリジン－３－イルメチル基、６－クロロピリジン－３－イルメチル基、２－ブロモピリジン－３－イルメチル基、４－ブロモピリジン－３－イルメチル基、５－ブロモピリジン－３－イルメチル基、６－ブロモピリジン－３－イルメチル基、２－メチルピリジン－３－イルメチル基、４－メチルピリジン－３－イルメチル基、５－メチルピリジン－３－イルメチル基、６－メチルピリジン－３－イルメチル基、２－トリフルオロメチルピリジン－３－イルメチル基、４－トリフルオロメチルピリジン－３－イルメチル基、５－トリフルオロメチルピリジン－３－イルメチル基、６－トリフルオロメチルピリジン－３－イルメチル基、２－メトキシピリジン－３－イルメチル基、４－メトキシピリジン－３－イルメチル基、５－メトキシピリジン－３－イルメチル基、６－メトキシピリジン－３－イルメチル基、
ピリジン－４－イルメチル基、２－フルオロピリジン－４－イルメチル基、３－フルオロピリジン－４－イルメチル基、２－クロロピリジン－４－イルメチル基、３－クロロピリジン－４－イルメチル基、２－ブロモピリジン－４－イルメチル基、３－ブロモピリジン－４－イルメチル基、２－メチルピリジン－４－イルメチル基、３－メチルピリジン－４－イルメチル基、２－トリフルオロメチルピリジン－４－イルメチル基、３－トリフルオロメチルピリジン－４－イルメチル基、２－メトキシピリジン－４－イルメチル基、３－メトキシピリジン－４－イルメチル基、
ピリダジン－３－イルメチル基、４－フルオロピリダジン－３－イルメチル基、５－フルオロピリダジン－３－イルメチル基、６－フルオロピリダジン－３－イルメチル基、４－クロロピリダジン－３－イルメチル基、５－クロロピリダジン－３－イルメチル基、６－クロロピリダジン－３－イルメチル基、４－ブロモピリダジン－３－イルメチル基、５－ブロモピリダジン－３－イルメチル基、６－ブロモピリダジン－３－イルメチル基、４－メチルピリダジン－３－イルメチル基、５－メチルピリダジン－３－イルメチル基、６－メチルピリダジン－３－イルメチル基、４－トリフルオロメチルピリダジン－３－イルメチル基、５－トリフルオロメチルピリダジン－３－イルメチル基、６－トリフルオロメチルピリダジン－３－イルメチル基、４－メトキシピリダジン－３－イルメチル基、５－メトキシピリダジン－３－イルメチル基、６－メトキシピリダジン－３－イルメチル基、
ピリダジン－４－イルメチル基、３－フルオロピリダジン－４－イルメチル基、５－フルオロピリダジン－４－イルメチル基、６－フルオロピリダジン－４－イルメチル基、３－クロロピリダジン－４－イルメチル基、５－クロロピリダジン－４－イルメチル基、６－クロロピリダジン－４－イルメチル基、３－ブロモピリダジン－４－イルメチル基、５－ブロモピリダジン－４－イルメチル基、６－ブロモピリダジン－４－イルメチル基、３－メチルピリダジン－４－イルメチル基、５－メチルピリダジン－４－イルメチル基、６－メチルピリダジン－４－イルメチル基、３－トリフルオロメチルピリダジン－４－イルメチル基、５－トリフルオロメチルピリダジン－４－イルメチル基、６－トリフルオロメチルピリダジン－４－イルメチル基、３－メトキシピリダジン－４－イルメチル基、５－メトキシピリダジン－４－イルメチル基、６－メトキシピリダジン－４－イルメチル基、
ピリミジン－２－イルメチル基、４－フルオロピリミジン－２－イルメチル基、５－フルオロピリミジン－２－イルメチル基、４－クロロピリミジン－２－イルメチル基、５－クロロピリミジン－２－イルメチル基、４－ブロモピリミジン－２－イルメチル基、５－ブロモピリミジン－２－イルメチル基、４－メチルピリミジン－２－イルメチル基、５－メチルピリミジン－２－イルメチル基、４－トリフルオロメチルピリミジン－２－イルメチル基、５－トリフルオロメチルピリミジン－２－イルメチル基、４－メトキシピリミジン－２－イルメチル基、５－メトキシピリミジン－２－イルメチル基、
ピリミジン－４－イルメチル基、２－フルオロピリミジン－４－イルメチル基、５－フルオロピリミジン－４－イルメチル基、６－フルオロピリミジン－４－イルメチル基、２－クロロピリミジン－４－イルメチル基、５－クロロピリミジン－４－イルメチル基、６－クロロピリミジン－４－イルメチル基、２－ブロモピリミジン－４－イルメチル基、５－ブロモピリミジン－４－イルメチル基、６－ブロモピリミジン－４－イルメチル基、２－メチルピリミジン－４－イルメチル基、５－メチルピリミジン－４－イルメチル基、６－メチルピリミジン－４－イルメチル基、２－トリフルオロメチルピリミジン－４－イルメチル基、５－トリフルオロメチルピリミジン－４－イルメチル基、６－トリフルオロメチルピリミジン－４－イルメチル基、２－メトキシピリミジン－４－イルメチル基、５－メトキシピリミジン－４－イルメチル基、６－メトキシピリミジン－４－イルメチル基、
ピリミジン－５－イルメチル基、２－フルオロピリミジン－５－イルメチル基、４－フルオロピリミジン－５－イルメチル基、６－フルオロピリミジン－５－イルメチル基、２－クロロピリミジン－５－イルメチル基、４－クロロピリミジン－５－イルメチル基、６－クロロピリミジン－５－イルメチル基、２－ブロモピリミジン－５－イルメチル基、４－ブロモピリミジン－５－イルメチル基、６－ブロモピリミジン－５－イルメチル基、２－メチルピリミジン－５－イルメチル基、４－メチルピリミジン－５－イルメチル基、６－メチルピリミジン－５－イルメチル基、２－トリフルオロメチルピリミジン－５－イルメチル基、４－トリフルオロメチルピリミジン－５－イルメチル基、６－トリフルオロメチルピリミジン－５－イルメチル基、２－メトキシピリミジン－５－イルメチル基、４－メトキシピリミジン－５－イルメチル基、６－メトキシピリミジン－５－イルメチル基、
ピラジン－２－イルメチル基、３－フルオロピラジン－２－イルメチル基、５－フルオロピラジン－２－イルメチル基、６－フルオロピラジン－２－イルメチル基、３－クロロピラジン－２－イルメチル基、５－クロロピラジン－２－イルメチル基、６－クロロピラジン－２－イルメチル基、３－ブロモピラジン－２－イルメチル基、５－ブロモピラジン－２－イルメチル基、６－ブロモピラジン－２－イルメチル基、３－メチルピラジン－２－イルメチル基、５－メチルピラジン－２－イルメチル基、６－メチルピラジン－２－イルメチル基、３－トリフルオロメチルピラジン－２－イルメチル基、５－トリフルオロメチルピラジン－２－イルメチル基、６－トリフルオロメチルピラジン－２－イルメチル基、３－メトキシピラジン－２－イルメチル基、５－メトキシピラジン－２－イルメチル基、６－メトキシピラジン－２－イルメチル基、
１－（ピリジン－２－イル）エチル基、１－（３－フルオロピリジン－２－イル）エチル基、１－（４－フルオロピリジン－２－イル）エチル基、１－（５－フルオロピリジン－２－イル）エチル基、１－（６－フルオロピリジン－２－イル）エチル基、１－（３－クロロピリジン－２－イル）エチル基、１－（４－クロロピリジン－２－イル）エチル基、１－（５－クロロピリジン－２－イル）エチル基、１－（６－クロロピリジン－２－イル）エチル基、１－（３－ブロモピリジン－２－イル）エチル基、１－（４－ブロモピリジン－２－イル）エチル基、１－（５－ブロモピリジン－２－イル）エチル基、１－（６－ブロモピリジン－２－イル）エチル基、１－（３－メチルピリジン－２－イル）エチル基、１－（４－メチルピリジン－２－イル）エチル基、１－（５－メチルピリジン－２－イル）エチル基、１－（６－メチルピリジン－２－イル）エチル基、１－（３－トリフルオロメチルピリジン－２－イル）エチル基、１－（４－トリフルオロメチルピリジン－２－イル）エチル基、１－（５－トリフルオロメチルピリジン－２－イル）エチル基、１－（６－トリフルオロメチルピリジン－２－イル）エチル基、１－（３－メトキシピリジン－２－イル）エチル基、１－（４－メトキシピリジン－２－イル）エチル基、１－（５－メトキシピリジン－２－イル）エチル基、１－（６－メトキシピリジン－２－イル）エチル基、
１－（ピリジン－３－イル）エチル基、１－（２－フルオロピリジン－３－イル）エチル基、１－（４－フルオロピリジン－３－イル）エチル基、１－（５－フルオロピリジン－３－イル）エチル基、１－（６－フルオロピリジン－３－イル）エチル基、１－（２－クロロピリジン－３－イル）エチル基、１－（４－クロロピリジン－３－イル）エチル基、１－（５－クロロピリジン－３－イル）エチル基、１－（６－クロロピリジン－３－イル）エチル基、１－（２－ブロモピリジン－３－イル）エチル基、１－（４－ブロモピリジン－３－イル）エチル基、１－（５－ブロモピリジン－３－イル）エチル基、１－（６－ブロモピリジン－３－イル）エチル基、１－（２－メチルピリジン－３－イル）エチル基、１－（４－メチルピリジン－３－イル）エチル基、１－（５－メチルピリジン－３－イル）エチル基、１－（６－メチルピリジン－３－イル）エチル基、１－（２－トリフルオロメチルピリジン－３－イル）エチル基、１－（４－トリフルオロメチルピリジン－３－イル）エチル基、１－（５－トリフルオロメチルピリジン－３－イル）エチル基、１－（６－トリフルオロメチルピリジン－３－イル）エチル基、１－（２－メトキシピリジン－３－イル）エチル基、１－（４－メトキシピリジン－３－イル）エチル基、１－（５－メトキシピリジン－３－イル）エチル基、１－（６－メトキシピリジン－３－イル）エチル基、
１－（ピリジン－４－イル）エチル基、１－（２－フルオロピリジン－４－イル）エチル基、１－（３－フルオロピリジン－４－イル）エチル基、１－（２－クロロピリジン－４－イル）エチル基、１－（３－クロロピリジン－４－イル）エチル基、１－（２－ブロモピリジン－４－イル）エチル基、１－（３－ブロモピリジン－４－イル）エチル基、１－（２－メチルピリジン－４－イル）エチル基、１－（３－メチルピリジン－４－イル）エチル基、１－（２－トリフルオロメチルピリジン－４－イル）エチル基、１－（３－トリフルオロメチルピリジン－４－イル）エチル基、１－（２－メトキシピリジン－４－イル）エチル基、１－（３－メトキシピリジン－４－イル）エチル基、
１－（ピリダジン－３－イル）エチル基、１－（４－フルオロピリダジン－３－イル）エチル基、１－（５－フルオロピリダジン－３－イル）エチル基、１－（６－フルオロピリダジン－３－イル）エチル基、１－（４－クロロピリダジン－３－イル）メチル基、１－（５－クロロピリダジン－３－イル）エチル基、１－（６－クロロピリダジン－３－イル）エチル基、１－（４－ブロモピリダジン－３－イル）エチル基、１－（５－ブロモピリダジン－３－イル）エチル基、１－（６－ブロモピリダジン－３－イル）エチル基、１－（４－メチルピリダジン－３－イル）エチル基、１－（５－メチルピリダジン－３－イル）エチル基、１－（６－メチルピリダジン－３－イル）エチル基、１－（４－トリフルオロメチルピリダジン－３－イル）エチル基、１－（５－トリフルオロメチルピリダジン－３－イル）エチル基、１－（６－トリフルオロメチルピリダジン－３－イル）エチル基、１－（４－メトキシピリダジン－３－イル）エチル基、１－（５－メトキシピリダジン－３－イル）エチル基、１－（６－メトキシピリダジン－３－イル）エチル基、
１－（ピリダジン－４－イル）エチル基、１－（３－フルオロピリダジン－４－イル）エチル基、１－（５－フルオロピリダジン－４－イル）エチル基、１－（６－フルオロピリダジン－４－イル）エチル基、１－（３－クロロピリダジン－４－イル）エチル基、１－（５－クロロピリダジン－４－イル）エチル基、１－（６－クロロピリダジン－４－イル）エチル基、１－（３－ブロモピリダジン－４－イル）エチル基、１－（５－ブロモピリダジン－４－イル）エチル基、１－（６－ブロモピリダジン－４－イル）エチル基、１－（３－メチルピリダジン－４－イル）エチル基、１－（５－メチルピリダジン－４－イル）エチル基、１－（６－メチルピリダジン－４－イル）エチル基、１－（３－トリフルオロメチルピリダジン－４－イル）エチル基、１－（５－トリフルオロメチルピリダジン－４－イル）エチル基、１－（６－トリフルオロメチルピリダジン－４－イル）エチル基、１－（３－メトキシピリダジン－４－イル）エチル基、１－（５－メトキシピリダジン－４－イル）エチル基、１－（６－メトキシピリダジン－４－イル）エチル基、
１－（ピリミジン－２－イル）エチル基、１－（４－フルオロピリミジン－２－イル）エチル基、１－（５－フルオロピリミジン－２－イル）エチル基、１－（４－クロロピリミジン－２－イル）エチル基、１－（５－クロロピリミジン－２－イル）エチル基、１－（４－ブロモピリミジン－２－イル）エチル基、１－（５－ブロモピリミジン－２－イル）エチル基、１－（４－メチルピリミジン－２－イル）エチル基、１－（５－メチルピリミジン－２－イル）エチル基、１－（４－トリフルオロメチルピリミジン－２－イル）エチル基、１－（５－トリフルオロメチルピリミジン－２－イル）エチル基、１－（４－メトキシピリミジン－２－イル）エチル基、１－（５－メトキシピリミジン－２－イル）エチル基、
１－（ピリミジン－４－イル）エチル基、１－（２－フルオロピリミジン－４－イル）エチル基、１－（５－フルオロピリミジン－４－イル）エチル基、１－（６－フルオロピリミジン－４－イル）エチル基、１－（２－クロロピリミジン－４－イル）エチル基、１－（５－クロロピリミジン－４－イル）エチル基、１－（６－クロロピリミジン－４－イル）エチル基、１－（２－ブロモピリミジン－４－イル）エチル基、１－（５－ブロモピリミジン－４－イル）エチル基、１－（６－ブロモピリミジン－４－イル）エチル基、１－（２－メチルピリミジン－４－イル）エチル基、１－（５－メチルピリミジン－４－イル）エチル基、１－（６－メチルピリミジン－４－イル）エチル基、１－（２－トリフルオロメチルピリミジン－４－イル）エチル基、１－（５－トリフルオロメチルピリミジン－４－イル）エチル基、１－（６－トリフルオロメチルピリミジン－４－イル）エチル基、１－（２－メトキシピリミジン－４－イル）エチル基、１－（５－メトキシピリミジン－４－イル）エチル基、１－（６－メトキシピリミジン－４－イル）エチル基、
１－（ピリミジン－５－イル）エチル基、１－（２－フルオロピリミジン－５－イル）エチル基、１－（４－フルオロピリミジン－５－イル）エチル基、１－（６－フルオロピリミジン－５－イル）エチル基、１－（２－クロロピリミジン－５－イル）エチル基、１－（４－クロロピリミジン－５－イル）エチル基、１－（６－クロロピリミジン－５－イル）エチル基、１－（２－ブロモピリミジン－５－イル）エチル基、１－（４－ブロモピリミジン－５－イル）エチル基、１－（６－ブロモピリミジン－５－イル）エチル基、１－（２－メチルピリミジン－５－イル）エチル基、１－（４－メチルピリミジン－５－イル）エチル基、１－（６－メチルピリミジン－５－イル）エチル基、１－（２－トリフルオロメチルピリミジン－５－イル）エチル基、１－（４－トリフルオロメチルピリミジン－５－イル）エチル基、１－（６－トリフルオロメチルピリミジン－５－イル）エチル基、１－（２－メトキシピリミジン－５－イル）エチル基、１－（４－メトキシピリミジン－５－イル）エチル基、１－（６－メトキシピリミジン－５－イル）エチル基、
１－（ピラジン－２－イル）エチル基、１－（３－フルオロピラジン－２－イル）エチル基、１－（５－フルオロピラジン－２－イル）エチル基、１－（６－フルオロピラジン－２－イル）エチル基、１－（３－クロロピラジン－２－イル）エチル基、１－（５－クロロピラジン－２－イル）エチル基、１－（６－クロロピラジン－２－イル）エチル基、１－（３－ブロモピラジン－２－イル）エチル基、１－（５－ブロモピラジン－２－イル）エチル基、１－（６－ブロモピラジン－２－イル）エチル基、１－（３－メチルピラジン－２－イル）エチル基、１－（５－メチルピラジン－２－イル）エチル基、１－（６－メチルピラジン－２－イル）エチル基、１－（３－トリフルオロメチルピラジン－２－イル）エチル基、１－（５－トリフルオロメチルピラジン－２－イル）エチル基、１－（６－トリフルオロメチルピラジン－２－イル）エチル基、１－（３－メトキシピラジン－２－イル）エチル基、１―（５－メトキシピラジン－２－イル）エチル基、１－（６－メトキシピラジン－２－イル）エチル基、
３－メチル－１,２,４－オキサジアゾリル基、５－フルオロ－３－メチル－１,２,４－オキサジアゾリル基、５－クロロ－３－メチル－１,２,４－オキサジアゾリル基、５－ブロモ－３－メチル－１,２,４－オキサジアゾリル基、５－メチル－３－メチル－１,２,４－オキサジアゾリル基、５－トリフルオロメチル－３－メチル－１,２,４－オキサジアゾリル基、５－メトキシ－３－メチル－１,２,４－オキサジアゾリル基、チアゾール－２－イルメチル基、チアゾール－４－イルメチル基、チアゾール－５－イルメチル基、
テトラヒドロフラン－２－イルメチル基、テトラヒドロフラン－３－イルメチル基、テトラヒドロ－２Ｈ－ピラン－２－イルメチル基、テトラヒドロ－２Ｈ－ピラン－４－イルメチル基、１，３－ジオキソラン－２－イルメチル基、または３－（ジヒドロフラン－２（３Ｈ）－オン）メチル基であり、
　より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ペンチル基、シアノメチル基、１－シアノエチル基、２－シアノエチル基、シクロプロピルメチル基、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基、イソプロピルオキシメチル基、ベンジル基、１－フェネチル基、２－フェネチル基、４－シアノフェニルメチル基、２－フルオロフェニルメチル基、３－フルオロフェニルメチル基、４－フルオロフェニルメチル基、２－クロロフェニルメチル基、３－クロロフェニルメチル基、３，５－ジクロロフェニルメチル基、４－クロロフェニルメチル基、２－メチルフェニルメチル基、３－メチルフェニルメチル基、４－メチルフェニルメチル基、２－トリフルオロメチルフェニルメチル基、３－トリフルオロメチルフェニルメチル基、４－トリフルオロメチルフェニルメチル基、３－シクロプロピルピリジン－２－イルメチル基、４－シクロプロピルピリジン－２－イルメチル基、５－シクロプロピルピリジン－２－イルメチル基、６－シクロプロピルピリジン－２－イルメチル基、２－メトキシフェニルメチル基、３－メトキシフェニルメチル基、４－メトキシフェニルメチル基、４－フェノキシフェニルメチル基、４－メタンスルホニルフェニルメチル基、４－トリフルオロメチルスルファニルフェニルメチル基、４－トリフルオロスルフィニルフェニルメチル基、４－トリフルオロスルホニルフェニルメチル基、ピリジン－２－イルメチル基、ピリジン－２－イルメチルＮ－オキシド基、３－クロロピリジン－２－イルメチル基、４－クロロピリジン－２－イルメチル基、５－クロロピリジン－２－イルメチル基、６－クロロピリジン－２－イルメチル基、３－ブロモピリジン－２－イルメチル基、４－ブロモピリジン－２－イルメチル基、５－ブロモピリジン－２－イルメチル基、６－ブロモピリジン－２－イルメチル基、３－メチルピリジン－２－イルメチル基、４－メチルピリジン－２－イルメチル基、５－メチルピリジン－２－イルメチル基、６－メチルピリジン－２－イルメチル基、３－トリフルオロメチルピリジン－２－イルメチル基、４－トリフルオロメチルピリジン－２－イルメチル基、５－トリフルオロメチルピリジン－２－イルメチル基、６－トリフルオロメチルピリジン－２－イルメチル基、
３－シクロプロピルピリジン－２－イルメチル基、４－シクロプロピルピリジン－２－イルメチル基、５－シクロプロピルピリジン－２－イルメチル基、６－シクロプロピルピリジン－２－イルメチル基、３－メトキシピリジン－２－イルメチル基、４－メトキシピリジン－２－イルメチル基、５－メトキシピリジン－２－イルメチル基、６－メトキシピリジン－２－イルメチル基、ピリジン－３－イルメチル基、２－クロロピリジン－３－イルメチル基、４－クロロピリジン－３－イルメチル基、５－クロロピリジン－３－イルメチル基、６－クロロピリジン－３－イルメチル基、２－メチルピリジン－３－イルメチル基、４－メチルピリジン－３－イルメチル基、５－メチルピリジン－３－イルメチル基、６－メチルピリジン－３－イルメチル基、２－トリフルオロメチルピリジン－３－イルメチル基、４－トリフルオロメチルピリジン－３－イルメチル基、５－トリフルオロメチルピリジン－３－イルメチル基、６－トリフルオロメチルピリジン－３－イルメチル基、ピリジン－４－イルメチル基、２－クロロピリジン－４－イルメチル基、３－クロロピリジン－４－イルメチル基、２－メチルピリジン－４－イルメチル基、３－メチルピリジン－４－イルメチル基、２－トリフルオロメチルピリジン－４－イルメチル基、３－トリフルオロメチルピリジン－４－イルメチル基、ピリダジン－３－イルメチル基、４－クロロピリダジン－３－イルメチル基、５－クロロピリダジン－３－イルメチル基、６－クロロピリダジン－３－イルメチル基、４－メチルピリダジン－３－イルメチル基、５－メチルピリダジン－３－イルメチル基、６－メチルピリダジン－３－イルメチル基、４－トリフルオロメチルピリダジン－３－イルメチル基、５－トリフルオロメチルピリダジン－３－イルメチル基、６－トリフルオロメチルピリダジン－３－イルメチル基、ピリダジン－４－イルメチル基、３－クロロピリダジン－４－イルメチル基、５－クロロピリダジン－４－イルメチル基、６－クロロピリダジン－４－イルメチル基、３－メチルピリダジン－４－イルメチル基、５－メチルピリダジン－４－イルメチル基、６－メチルピリダジン－４－イルメチル基、３－トリフルオロメチルピリダジン－４－イルメチル基、５－トリフルオロメチルピリダジン－４－イルメチル基、６－トリフルオロメチルピリダジン－４－イルメチル基、３－メトキシピリダジン－４－イルメチル基、ピリミジン－２－イルメチル基、
４－クロロピリミジン－２－イルメチル基、５－クロロピリミジン－２－イルメチル基、４－メチルピリミジン－２－イルメチル基、５－メチルピリミジン－２－イルメチル基、４－トリフルオロメチルピリミジン－２－イルメチル基、５－トリフルオロメチルピリミジン－２－イルメチル基、ピリミジン－４－イルメチル基、２－クロロピリミジン－４－イルメチル基、５－クロロピリミジン－４－イルメチル基、６－クロロピリミジン－４－イルメチル基、２－メチルピリミジン－４－イルメチル基、５－メチルピリミジン－４－イルメチル基、６－メチルピリミジン－４－イルメチル基、２－トリフルオロメチルピリミジン－４－イルメチル基、５－トリフルオロメチルピリミジン－４－イルメチル基、６－トリフルオロメチルピリミジン－４－イルメチル基、ピリミジン－５－イルメチル基、２－クロロピリミジン－５－イルメチル基、４－クロロピリミジン－５－イルメチル基、６－クロロピリミジン－５－イルメチル基、２－メチルピリミジン－５－イルメチル基、４－メチルピリミジン－５－イルメチル基、６－メチルピリミジン－５－イルメチル基、２－トリフルオロメチルピリミジン－５－イルメチル基、４－トリフルオロメチルピリミジン－５－イルメチル基、６－トリフルオロメチルピリミジン－５－イルメチル基、ピラジン－２－イルメチル基、３－クロロピラジン－２－イルメチル基、５－クロロピラジン－２－イルメチル基、６－クロロピラジン－２－イルメチル基、３－メチルピラジン－２－イルメチル基、５－メチルピラジン－２－イルメチル基、６－メチルピラジン－２－イルメチル基、３－トリフルオロメチルピラジン－２－イルメチル基、５－トリフルオロメチルピラジン－２－イルメチル基、６－トリフルオロメチルピラジン－２－イルメチル基、１－（ピリジン－２－イル）エチル基、１－（３－クロロピリジン－２－イル）エチル基、１－（４－クロロピリジン－２－イル）エチル基、１－（５－クロロピリジン－２－イル）エチル基、１－（６－クロロピリジン－２－イル）エチル基、１－（３－メチルピリジン－２－イル）エチル基、１－（４－メチルピリジン－２－イル）エチル基、１－（５－メチルピリジン－２－イル）エチル基、１－（６－メチルピリジン－２－イル）エチル基、１－（３－トリフルオロメチルピリジン－２－イル）エチル基、１－（４－トリフルオロメチルピリジン－２－イル）エチル基、１－（５－トリフルオロメチルピリジン－２－イル）エチル基、１－（６－トリフルオロメチルピリジン－２－イル）エチル基、
１－（ピリジン－３－イル）エチル基、１－（２－クロロピリジン－３－イル）エチル基、１－（４－クロロピリジン－３－イル）エチル基、１－（５－クロロピリジン－３－イル）エチル基、１－（６－クロロピリジン－３－イル）エチル基、１－（２－メチルピリジン－３－イル）エチル基、１－（４－メチルピリジン－３－イル）エチル基、１－（５－メチルピリジン－３－イル）エチル基、１－（６－メチルピリジン－３－イル）エチル基、１－（２－トリフルオロメチルピリジン－３－イル）エチル基、１－（４－トリフルオロメチルピリジン－３－イル）エチル基、１－（５－トリフルオロメチルピリジン－３－イル）エチル基、１－（６－トリフルオロメチルピリジン－３－イル）エチル基、１－（ピリジン－４－イル）エチル基、１－（２－クロロピリジン－４－イル）エチル基、１－（３－クロロピリジン－４－イル）エチル基、１－（２－メチルピリジン－４－イル）エチル基、１－（３－メチルピリジン－４－イル）エチル基、１－（２－トリフルオロメチルピリジン－４－イル）エチル基、１－（３－トリフルオロメチルピリジン－４－イル）エチル基、１－（ピリダジン－３－イル）エチル基、１－（４－クロロピリダジン－３－イル）メチル基、１－（５－クロロピリダジン－３－イル）エチル基、１－（６－クロロピリダジン－３－イル）エチル基、１－（４－メチルピリダジン－３－イル）エチル基、１－（５－メチルピリダジン－３－イル）エチル基、１－（６－メチルピリダジン－３－イル）エチル基、１－（４－トリフルオロメチルピリダジン－３－イル）エチル基、１－（５－トリフルオロメチルピリダジン－３－イル）エチル基、１－（６－トリフルオロメチルピリダジン－３－イル）エチル基、１－（ピリダジン－４－イル）エチル基、１－（３－クロロピリダジン－４－イル）エチル基、１－（５－クロロピリダジン－４－イル）エチル基、１－（６－クロロピリダジン－４－イル）エチル基、１－（３－メチルピリダジン－４－イル）エチル基、１－（５－メチルピリダジン－４－イル）エチル基、１－（６－メチルピリダジン－４－イル）エチル基、１－（３－トリフルオロメチルピリダジン－４－イル）エチル基、１－（５－トリフルオロメチルピリダジン－４－イル）エチル基、１－（６－トリフルオロメチルピリダジン－４－イル）エチル基、１－（ピリミジン－２－イル）エチル基、１－（４－クロロピリミジン－２－イル）エチル基、１－（５－クロロピリミジン－２－イル）エチル基、１－（４－メチルピリミジン－２－イル）エチル基、１－（５－メチルピリミジン－２－イル）エチル基、１－（４－トリフルオロメチルピリミジン－２－イル）エチル基、１－（５－トリフルオロメチルピリミジン－２－イル）エチル基、１－（ピリミジン－４－イル）エチル基、１－（２－クロロピリミジン－４－イル）エチル基、１－（５－クロロピリミジン－４－イル）エチル基、１－（６－クロロピリミジン－４－イル）エチル基、１－（２－メチルピリミジン－４－イル）エチル基、１－（５－メチルピリミジン－４－イル）エチル基、１－（６－メチルピリミジン－４－イル）エチル基、１－（２－トリフルオロメチルピリミジン－４－イル）エチル基、１－（５－トリフルオロメチルピリミジン－４－イル）エチル基、１－（６－トリフルオロメチルピリミジン－４－イル）エチル基、１－（ピリミジン－５－イル）エチル基、１－（２－クロロピリミジン－５－イル）エチル基、１－（４－クロロピリミジン－５－イル）エチル基、１－（６－クロロピリミジン－５－イル）エチル基、１－（２－メチルピリミジン－５－イル）エチル基、１－（４－メチルピリミジン－５－イル）エチル基、１－（６－メチルピリミジン－５－イル）エチル基、１－（２－トリフルオロメチルピリミジン－５－イル）エチル基、１－（４－トリフルオロメチルピリミジン－５－イル）エチル基、１－（６－トリフルオロメチルピリミジン－５－イル）エチル基、１－（ピラジン－２－イル）エチル基、１－（３－クロロピラジン－２－イル）エチル基、１－（５－クロロピラジン－２－イル）エチル基、１－（６－クロロピラジン－２－イル）エチル基、１－（３－メチルピラジン－２－イル）エチル基、１－（５－メチルピラジン－２－イル）エチル基、１－（６－メチルピラジン－２－イル）エチル基、１－（３－トリフルオロメチルピラジン－２－イル）エチル基、１－（５－トリフルオロメチルピラジン－２－イル）エチル基、１－（６－トリフルオロメチルピラジン－２－イル）エチル基、３－メチル－１,２,４－オキサジアゾリル基、５－トリフルオロメチル－３－メチル－１,２,４－オキサジアゾリル基、チアゾール－２－イルメチル基、チアゾール－４－イルメチル基、チアゾール－５－イルメチル基、プロパン－２－オン基、メトキシカルボニルメチル基、メトキシカルボニルエチル基、エトキシカルボニルメチル基、エトキシカルボニルエチル基、ジメチルアミノカルボニルメチル基、エチルメチルアミノカルボニルメチル基、メチルスルファニルメチル基、メチルスルフィニルメチル基、メチルスルホニルメチル基、エチルスルファニルメチル基、エチルスルフィニルメチル基、エチルスルホニルメチル基、トリフルオロメチルスルファニルメチル基、トリフルオロメチルスルフィニルメチル基、トリフルオロスルホニルメチル基、テトラヒドロフラン－２－イルメチル基、テトラヒドロフラン－３－イルメチル基、テトラヒドロ－２Ｈ－ピラン－２－イルメチル基、テトラヒドロ－２Ｈ－ピラン－４－イルメチル基、または１，３－ジオキソラン－２－イルメチル基、３－（ジヒドロフラン－２（３Ｈ）－オン）メチル基であり、
　さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、シアノメチル基、２－シアノエチル基、シクロプロピルメチル基、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基である。
　特に好ましくは、メチル基、またはエチル基である。 The C1-C6 alkyl group in the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a pentyl group, and particularly preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or a sec-butyl group. When the C1-C6 alkyl group has a substituent in the description of the substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted with a substituent in the description of the substituent A.
Preferred examples of the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, a hexyl group, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a 3-cyanopropyl group, a 2-cyanopropan-2-yl group, a cyclopropylmethyl group, a cyclobutylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, an isopropyloxymethyl group, an isopropyloxyethyl group,
benzyl group, 1-phenethyl group, 2-phenethyl group, 4-cyanophenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphenylmethyl group, 3-trifluoromethylphenylmethyl group, 4-trifluoromethylphenylmethyl group, 2-methoxyphenylmethyl group, 3-methoxyphenylmethyl group, 4-methoxyphenylmethyl group, 4-phenoxyphenylmethyl group, 4-methanesulfonylphenylmethyl group, trifluoromethylsulfanylphenylmethyl group,
pyridin-2-ylmethyl group, pyridin-2-ylmethyl N-oxide group, 3-fluoropyridin-2-ylmethyl group, 4-fluoropyridin-2-ylmethyl group, 5-fluoropyridin-2-ylmethyl group, 6-fluoropyridin-2-ylmethyl group, 3-chloropyridin-2-ylmethyl group, 4-chloropyridin-2-ylmethyl group, 5-chloropyridin-2-ylmethyl group, 6-chloropyridin-2-ylmethyl group, 3-bromopyridin-2-ylmethyl group, 4-bromopyridin-2-ylmethyl group, 5-bromopyridin-2-ylmethyl group, 6-bromopyridin-2-ylmethyl group, 3-methylpyridin-2-ylmethyl group, 4-methylpyridin-2-ylmethyl group, 5-methylpyridin-2-ylmethyl group, ethylpyridin-2-ylmethyl group, 6-methylpyridin-2-ylmethyl group, 3-trifluoromethylpyridin-2-ylmethyl group, 4-trifluoromethylpyridin-2-ylmethyl group, 5-trifluoromethylpyridin-2-ylmethyl group, 6-trifluoromethylpyridin-2-ylmethyl group, 3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 3-methoxypyridin-2-ylmethyl group, 4-methoxypyridin-2-ylmethyl group, 5-methoxypyridin-2-ylmethyl group, 6-methoxypyridin-2-ylmethyl group,
pyridin-3-ylmethyl group, 2-fluoropyridin-3-ylmethyl group, 4-fluoropyridin-3-ylmethyl group, 5-fluoropyridin-3-ylmethyl group, 6-fluoropyridin-3-ylmethyl group, 2-chloropyridin-3-ylmethyl group, 4-chloropyridin-3-ylmethyl group, 5-chloropyridin-3-ylmethyl group, 6-chloropyridin-3-ylmethyl group, 2-bromopyridin-3-ylmethyl group, 4-bromopyridin-3-ylmethyl group, 5-bromopyridin-3-ylmethyl group, 6-bromopyridin-3-ylmethyl group, 2-methyl pyridin-3-ylmethyl group, 4-methylpyridin-3-ylmethyl group, 5-methylpyridin-3-ylmethyl group, 6-methylpyridin-3-ylmethyl group, 2-trifluoromethylpyridin-3-ylmethyl group, 4-trifluoromethylpyridin-3-ylmethyl group, 5-trifluoromethylpyridin-3-ylmethyl group, 6-trifluoromethylpyridin-3-ylmethyl group, 2-methoxypyridin-3-ylmethyl group, 4-methoxypyridin-3-ylmethyl group, 5-methoxypyridin-3-ylmethyl group, 6-methoxypyridin-3-ylmethyl group,
pyridin-4-ylmethyl group, 2-fluoropyridin-4-ylmethyl group, 3-fluoropyridin-4-ylmethyl group, 2-chloropyridin-4-ylmethyl group, 3-chloropyridin-4-ylmethyl group, 2-bromopyridin-4-ylmethyl group, 3-bromopyridin-4-ylmethyl group, 2-methylpyridin-4-ylmethyl group, 3-methylpyridin-4-ylmethyl group, 2-trifluoromethylpyridin-4-ylmethyl group, 3-trifluoromethylpyridin-4-ylmethyl group, 2-methoxypyridin-4-ylmethyl group, 3-methoxypyridin-4-ylmethyl group,
pyridazin-3-ylmethyl group, 4-fluoropyridazin-3-ylmethyl group, 5-fluoropyridazin-3-ylmethyl group, 6-fluoropyridazin-3-ylmethyl group, 4-chloropyridazin-3-ylmethyl group, 5-chloropyridazin-3-ylmethyl group, 6-chloropyridazin-3-ylmethyl group, 4-bromopyridazin-3-ylmethyl group, 5-bromopyridazin-3-ylmethyl group, 6-bromopyridazin-3-ylmethyl group, 4 -methylpyridazin-3-ylmethyl group, 5-methylpyridazin-3-ylmethyl group, 6-methylpyridazin-3-ylmethyl group, 4-trifluoromethylpyridazin-3-ylmethyl group, 5-trifluoromethylpyridazin-3-ylmethyl group, 6-trifluoromethylpyridazin-3-ylmethyl group, 4-methoxypyridazin-3-ylmethyl group, 5-methoxypyridazin-3-ylmethyl group, 6-methoxypyridazin-3-ylmethyl group,
pyridazin-4-ylmethyl group, 3-fluoropyridazin-4-ylmethyl group, 5-fluoropyridazin-4-ylmethyl group, 6-fluoropyridazin-4-ylmethyl group, 3-chloropyridazin-4-ylmethyl group, 5-chloropyridazin-4-ylmethyl group, 6-chloropyridazin-4-ylmethyl group, 3-bromopyridazin-4-ylmethyl group, 5-bromopyridazin-4-ylmethyl group, 6-bromopyridazin-4-ylmethyl group, 3 -methylpyridazin-4-ylmethyl group, 5-methylpyridazin-4-ylmethyl group, 6-methylpyridazin-4-ylmethyl group, 3-trifluoromethylpyridazin-4-ylmethyl group, 5-trifluoromethylpyridazin-4-ylmethyl group, 6-trifluoromethylpyridazin-4-ylmethyl group, 3-methoxypyridazin-4-ylmethyl group, 5-methoxypyridazin-4-ylmethyl group, 6-methoxypyridazin-4-ylmethyl group,
pyrimidin-2-ylmethyl group, 4-fluoropyrimidin-2-ylmethyl group, 5-fluoropyrimidin-2-ylmethyl group, 4-chloropyrimidin-2-ylmethyl group, 5-chloropyrimidin-2-ylmethyl group, 4-bromopyrimidin-2-ylmethyl group, 5-bromopyrimidin-2-ylmethyl group, 4-methylpyrimidin-2-ylmethyl group, 5-methylpyrimidin-2-ylmethyl group, 4-trifluoromethylpyrimidin-2-ylmethyl group, 5-trifluoromethylpyrimidin-2-ylmethyl group, 4-methoxypyrimidin-2-ylmethyl group, 5-methoxypyrimidin-2-ylmethyl group,
pyrimidin-4-ylmethyl group, 2-fluoropyrimidin-4-ylmethyl group, 5-fluoropyrimidin-4-ylmethyl group, 6-fluoropyrimidin-4-ylmethyl group, 2-chloropyrimidin-4-ylmethyl group, 5-chloropyrimidin-4-ylmethyl group, 6-chloropyrimidin-4-ylmethyl group, 2-bromopyrimidin-4-ylmethyl group, 5-bromopyrimidin-4-ylmethyl group, 6-bromopyrimidin-4-ylmethyl group, 2 -methylpyrimidin-4-ylmethyl group, 5-methylpyrimidin-4-ylmethyl group, 6-methylpyrimidin-4-ylmethyl group, 2-trifluoromethylpyrimidin-4-ylmethyl group, 5-trifluoromethylpyrimidin-4-ylmethyl group, 6-trifluoromethylpyrimidin-4-ylmethyl group, 2-methoxypyrimidin-4-ylmethyl group, 5-methoxypyrimidin-4-ylmethyl group, 6-methoxypyrimidin-4-ylmethyl group,
pyrimidin-5-ylmethyl group, 2-fluoropyrimidin-5-ylmethyl group, 4-fluoropyrimidin-5-ylmethyl group, 6-fluoropyrimidin-5-ylmethyl group, 2-chloropyrimidin-5-ylmethyl group, 4-chloropyrimidin-5-ylmethyl group, 6-chloropyrimidin-5-ylmethyl group, 2-bromopyrimidin-5-ylmethyl group, 4-bromopyrimidin-5-ylmethyl group, 6-bromopyrimidin-5-ylmethyl group, 2 -methylpyrimidin-5-ylmethyl group, 4-methylpyrimidin-5-ylmethyl group, 6-methylpyrimidin-5-ylmethyl group, 2-trifluoromethylpyrimidin-5-ylmethyl group, 4-trifluoromethylpyrimidin-5-ylmethyl group, 6-trifluoromethylpyrimidin-5-ylmethyl group, 2-methoxypyrimidin-5-ylmethyl group, 4-methoxypyrimidin-5-ylmethyl group, 6-methoxypyrimidin-5-ylmethyl group,
pyrazin-2-ylmethyl group, 3-fluoropyrazin-2-ylmethyl group, 5-fluoropyrazin-2-ylmethyl group, 6-fluoropyrazin-2-ylmethyl group, 3-chloropyrazin-2-ylmethyl group, 5-chloropyrazin-2-ylmethyl group, 6-chloropyrazin-2-ylmethyl group, 3-bromopyrazin-2-ylmethyl group, 5-bromopyrazin-2-ylmethyl group, 6-bromopyrazin-2-ylmethyl group, 3-methylpyrazin-2-ylmethyl group, 5-methylpyrazin-2-ylmethyl group, 6-methylpyrazin-2-ylmethyl group, 3-trifluoromethylpyrazin-2-ylmethyl group, 5-trifluoromethylpyrazin-2-ylmethyl group, 6-trifluoromethylpyrazin-2-ylmethyl group, 3-methoxypyrazin-2-ylmethyl group, 5-methoxypyrazin-2-ylmethyl group, 6-methoxypyrazin-2-ylmethyl group,
1-(pyridin-2-yl)ethyl group, 1-(3-fluoropyridin-2-yl)ethyl group, 1-(4-fluoropyridin-2-yl)ethyl group, 1-(5-fluoropyridin-2-yl)ethyl group, 1-(6-fluoropyridin-2-yl)ethyl group, 1-(3-chloropyridin-2-yl)ethyl group, 1-(4-chloropyridin-2-yl)ethyl group, 1-(5-chloropyridin-2-yl)ethyl group, 1-(6-chloropyridin-2-yl)ethyl group, 1-(3-bromopyridin-2-yl)ethyl group, 1-(4-bromopyridin-2-yl)ethyl group, 1-(5-bromopyridin-2-yl)ethyl group, 1-(6-bromopyridin-2-yl)ethyl group, 1-( 3-methylpyridin-2-yl)ethyl group, 1-(4-methylpyridin-2-yl)ethyl group, 1-(5-methylpyridin-2-yl)ethyl group, 1-(6-methylpyridin-2-yl)ethyl group, 1-(3-trifluoromethylpyridin-2-yl)ethyl group, 1-(4-trifluoromethylpyridin-2-yl)ethyl group, 1-(5-trifluoromethylpyridin-2-yl)ethyl group, 1-(6-trifluoromethylpyridin-2-yl)ethyl group, 1-(3-methoxypyridin-2-yl)ethyl group, 1-(4-methoxypyridin-2-yl)ethyl group, 1-(5-methoxypyridin-2-yl)ethyl group, 1-(6-methoxypyridin-2-yl)ethyl group,
1-(pyridin-3-yl)ethyl group, 1-(2-fluoropyridin-3-yl)ethyl group, 1-(4-fluoropyridin-3-yl)ethyl group, 1-(5-fluoropyridin-3-yl)ethyl group, 1-(6-fluoropyridin-3-yl)ethyl group, 1-(2-chloropyridin-3-yl)ethyl group, 1-(4-chloropyridin-3-yl)ethyl group, 1-(5-chloropyridin-3-yl)ethyl group, 1-(6-chloropyridin-3-yl)ethyl group, 1-(2-bromopyridin-3-yl)ethyl group, 1-(4-bromopyridin-3-yl)ethyl group, 1-(5-bromopyridin-3-yl)ethyl group, 1-(6-bromopyridin-3-yl)ethyl group, 2-methylpyridin-3-yl)ethyl group, 1-(4-methylpyridin-3-yl)ethyl group, 1-(5-methylpyridin-3-yl)ethyl group, 1-(6-methylpyridin-3-yl)ethyl group, 1-(2-trifluoromethylpyridin-3-yl)ethyl group, 1-(4-trifluoromethylpyridin-3-yl)ethyl group, 1-(5-trifluoromethylpyridin-3-yl)ethyl group, 1-(6-trifluoromethylpyridin-3-yl)ethyl group, 1-(2-methoxypyridin-3-yl)ethyl group, 1-(4-methoxypyridin-3-yl)ethyl group, 1-(5-methoxypyridin-3-yl)ethyl group, 1-(6-methoxypyridin-3-yl)ethyl group,
1-(pyridin-4-yl)ethyl group, 1-(2-fluoropyridin-4-yl)ethyl group, 1-(3-fluoropyridin-4-yl)ethyl group, 1-(2-chloropyridin-4-yl)ethyl group, 1-(3-chloropyridin-4-yl)ethyl group, 1-(2-bromopyridin-4-yl)ethyl group, 1-(3-bromopyridin-4-yl)ethyl group, 1-(2-methylpyridin-4-yl)ethyl group, 1-(3-methylpyridin-4-yl)ethyl group, 1-(2-trifluoromethylpyridin-4-yl)ethyl group, 1-(3-trifluoromethylpyridin-4-yl)ethyl group, 1-(2-methoxypyridin-4-yl)ethyl group, 1-(3-methoxypyridin-4-yl)ethyl group,
1-(pyridazin-3-yl)ethyl group, 1-(4-fluoropyridazin-3-yl)ethyl group, 1-(5-fluoropyridazin-3-yl)ethyl group, 1-(6-fluoropyridazin-3-yl)ethyl group, 1-(4-chloropyridazin-3-yl)methyl group, 1-(5-chloropyridazin-3-yl)ethyl group, 1-(6-chloropyridazin-3-yl)ethyl group, 1-(4-bromopyridazin-3-yl)ethyl group, 1-(5-bromopyridazin-3-yl)ethyl group, 1-(6-bromopyridazin-3-yl)ethyl group , 1-(4-methylpyridazin-3-yl)ethyl group, 1-(5-methylpyridazin-3-yl)ethyl group, 1-(6-methylpyridazin-3-yl)ethyl group, 1-(4-trifluoromethylpyridazin-3-yl)ethyl group, 1-(5-trifluoromethylpyridazin-3-yl)ethyl group, 1-(6-trifluoromethylpyridazin-3-yl)ethyl group, 1-(4-methoxypyridazin-3-yl)ethyl group, 1-(5-methoxypyridazin-3-yl)ethyl group, 1-(6-methoxypyridazin-3-yl)ethyl group,
1-(pyridazin-4-yl)ethyl group, 1-(3-fluoropyridazin-4-yl)ethyl group, 1-(5-fluoropyridazin-4-yl)ethyl group, 1-(6-fluoropyridazin-4-yl)ethyl group, 1-(3-chloropyridazin-4-yl)ethyl group, 1-(5-chloropyridazin-4-yl)ethyl group, 1-(6-chloropyridazin-4-yl)ethyl group, 1-(3-bromopyridazin-4-yl)ethyl group, 1-(5-bromopyridazin-4-yl)ethyl group, 1-(6-bromopyridazin-4-yl)ethyl group , 1-(3-methylpyridazin-4-yl)ethyl group, 1-(5-methylpyridazin-4-yl)ethyl group, 1-(6-methylpyridazin-4-yl)ethyl group, 1-(3-trifluoromethylpyridazin-4-yl)ethyl group, 1-(5-trifluoromethylpyridazin-4-yl)ethyl group, 1-(6-trifluoromethylpyridazin-4-yl)ethyl group, 1-(3-methoxypyridazin-4-yl)ethyl group, 1-(5-methoxypyridazin-4-yl)ethyl group, 1-(6-methoxypyridazin-4-yl)ethyl group,
1-(pyrimidin-2-yl)ethyl group, 1-(4-fluoropyrimidin-2-yl)ethyl group, 1-(5-fluoropyrimidin-2-yl)ethyl group, 1-(4-chloropyrimidin-2-yl)ethyl group, 1-(5-chloropyrimidin-2-yl)ethyl group, 1-(4-bromopyrimidin-2-yl)ethyl group, 1-(5-bromopyrimidin-2-yl)ethyl group, 1-(4-methylpyrimidin-2-yl)ethyl group, 1-(5-methylpyrimidin-2-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(4-methoxypyrimidin-2-yl)ethyl group, 1-(5-methoxypyrimidin-2-yl)ethyl group,
1-(pyrimidin-4-yl)ethyl group, 1-(2-fluoropyrimidin-4-yl)ethyl group, 1-(5-fluoropyrimidin-4-yl)ethyl group, 1-(6-fluoropyrimidin-4-yl)ethyl group, 1-(2-chloropyrimidin-4-yl)ethyl group, 1-(5-chloropyrimidin-4-yl)ethyl group, 1-(6-chloropyrimidin-4-yl)ethyl group, 1-(2-bromopyrimidin-4-yl)ethyl group, 1-(5-bromopyrimidin-4-yl)ethyl group, 1-(6-bromopyrimidin-4-yl)ethyl group , 1-(2-methylpyrimidin-4-yl)ethyl group, 1-(5-methylpyrimidin-4-yl)ethyl group, 1-(6-methylpyrimidin-4-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(2-methoxypyrimidin-4-yl)ethyl group, 1-(5-methoxypyrimidin-4-yl)ethyl group, 1-(6-methoxypyrimidin-4-yl)ethyl group,
1-(pyrimidin-5-yl)ethyl group, 1-(2-fluoropyrimidin-5-yl)ethyl group, 1-(4-fluoropyrimidin-5-yl)ethyl group, 1-(6-fluoropyrimidin-5-yl)ethyl group, 1-(2-chloropyrimidin-5-yl)ethyl group, 1-(4-chloropyrimidin-5-yl)ethyl group, 1-(6-chloropyrimidin-5-yl)ethyl group, 1-(2-bromopyrimidin-5-yl)ethyl group, 1-(4-bromopyrimidin-5-yl)ethyl group, 1-(6-bromopyrimidin-5-yl)ethyl group , 1-(2-methylpyrimidin-5-yl)ethyl group, 1-(4-methylpyrimidin-5-yl)ethyl group, 1-(6-methylpyrimidin-5-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(2-methoxypyrimidin-5-yl)ethyl group, 1-(4-methoxypyrimidin-5-yl)ethyl group, 1-(6-methoxypyrimidin-5-yl)ethyl group,
1-(pyrazin-2-yl)ethyl group, 1-(3-fluoropyrazin-2-yl)ethyl group, 1-(5-fluoropyrazin-2-yl)ethyl group, 1-(6-fluoropyrazin-2-yl)ethyl group, 1-(3-chloropyrazin-2-yl)ethyl group, 1-(5-chloropyrazin-2-yl)ethyl group, 1-(6-chloropyrazin-2-yl)ethyl group, 1-(3-bromopyrazin-2-yl)ethyl group, 1-(5-bromopyrazin-2-yl)ethyl group, 1-(6-bromopyrazin-2-yl)ethyl group, 1-(3-methylpyrazin-2-yl)ethyl group, 1-(5-methylpyrazin-2-yl)ethyl group, 1-(6-methylpyrazin-2-yl)ethyl group, 1-(3-trifluoromethylpyrazin-2-yl)ethyl group, 1-(5-trifluoromethylpyrazin-2-yl)ethyl group, 1-(6-trifluoromethylpyrazin-2-yl)ethyl group, 1-(3-methoxypyrazin-2-yl)ethyl group, 1-(5-methoxypyrazin-2-yl)ethyl group, 1-(6-methoxypyrazin-2-yl)ethyl group,
3-methyl-1,2,4-oxadiazolyl group, 5-fluoro-3-methyl-1,2,4-oxadiazolyl group, 5-chloro-3-methyl-1,2,4-oxadiazolyl group, 5-bromo-3-methyl-1,2,4-oxadiazolyl group, 5-methyl-3-methyl-1,2,4-oxadiazolyl group, 5-trifluoromethyl-3-methyl-1,2,4-oxadiazolyl group, 5-methoxy-3-methyl-1,2,4-oxadiazolyl group, thiazol-2-ylmethyl group, thiazol-4-ylmethyl group, thiazol-5-ylmethyl group,
a tetrahydrofuran-2-ylmethyl group, a tetrahydrofuran-3-ylmethyl group, a tetrahydro-2H-pyran-2-ylmethyl group, a tetrahydro-2H-pyran-4-ylmethyl group, a 1,3-dioxolan-2-ylmethyl group, or a 3-(dihydrofuran-2(3H)-one)methyl group;
More preferred are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a pentyl group, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a cyclopropylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, an isopropyloxymethyl group, a benzyl group, a 1-phenethyl group, a 2-phenethyl group, a 4-cyanophenylmethyl group, a 2-fluorophenylmethyl group, a 3-fluorophenylmethyl group, a 4-fluorophenylmethyl group, a 2-chlorophenylmethyl group, a 3-chlorophenylmethyl group, a 4-chlorophenylmethyl group, a 2 ... chlorophenylmethyl group, 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphenylmethyl group, 3-trifluoromethylphenylmethyl group, 4-trifluoromethylphenylmethyl group, 3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 2-methoxyphenylmethyl group , 3-methoxyphenylmethyl group, 4-methoxyphenylmethyl group, 4-phenoxyphenylmethyl group, 4-methanesulfonylphenylmethyl group, 4-trifluoromethylsulfanylphenylmethyl group, 4-trifluorosulfinylphenylmethyl group, 4-trifluorosulfonylphenylmethyl group, pyridin-2-ylmethyl group, pyridin-2-ylmethyl N-oxide group, 3-chloropyridin-2-ylmethyl group, 4-chloropyridin-2-ylmethyl group, 5-chloropyridin-2-ylmethyl group, 6-chloropyridin-2-ylmethyl group, 3- bromopyridin-2-ylmethyl group, 4-bromopyridin-2-ylmethyl group, 5-bromopyridin-2-ylmethyl group, 6-bromopyridin-2-ylmethyl group, 3-methylpyridin-2-ylmethyl group, 4-methylpyridin-2-ylmethyl group, 5-methylpyridin-2-ylmethyl group, 6-methylpyridin-2-ylmethyl group, 3-trifluoromethylpyridin-2-ylmethyl group, 4-trifluoromethylpyridin-2-ylmethyl group, 5-trifluoromethylpyridin-2-ylmethyl group, 6-trifluoromethylpyridin-2-ylmethyl group,
3-cyclopropylpyridin-2-ylmethyl group, 4-cyclopropylpyridin-2-ylmethyl group, 5-cyclopropylpyridin-2-ylmethyl group, 6-cyclopropylpyridin-2-ylmethyl group, 3-methoxypyridin-2-ylmethyl group, 4-methoxypyridin-2-ylmethyl group, 5-methoxypyridin-2-ylmethyl group, 6-methoxypyridin-2-ylmethyl group, pyridin-3-ylmethyl group, 2-chloropyridin-3-ylmethyl group, 4-chloropyridin-3-ylmethyl group, 5-chloropyridin-3-ylmethyl group, 6-chloropyridin-3-ylmethyl group group, 2-methylpyridin-3-ylmethyl group, 4-methylpyridin-3-ylmethyl group, 5-methylpyridin-3-ylmethyl group, 6-methylpyridin-3-ylmethyl group, 2-trifluoromethylpyridin-3-ylmethyl group, 4-trifluoromethylpyridin-3-ylmethyl group, 5-trifluoromethylpyridin-3-ylmethyl group, 6-trifluoromethylpyridin-3-ylmethyl group, pyridin-4-ylmethyl group, 2-chloropyridin-4-ylmethyl group, 3-chloropyridin-4-ylmethyl group, 2-methylpyridin-4-ylmethyl group, 3-methylpyridin-4 -ylmethyl group, 2-trifluoromethylpyridin-4-ylmethyl group, 3-trifluoromethylpyridin-4-ylmethyl group, pyridazin-3-ylmethyl group, 4-chloropyridazin-3-ylmethyl group, 5-chloropyridazin-3-ylmethyl group, 6-chloropyridazin-3-ylmethyl group, 4-methylpyridazin-3-ylmethyl group, 5-methylpyridazin-3-ylmethyl group, 6-methylpyridazin-3-ylmethyl group, 4-trifluoromethylpyridazin-3-ylmethyl group, 5-trifluoromethylpyridazin-3-ylmethyl group, 6-trifluoromethylpyridazin-3-ylmethyl group, a pyridazin-3-ylmethyl group, a pyridazin-4-ylmethyl group, a 3-chloropyridazin-4-ylmethyl group, a 5-chloropyridazin-4-ylmethyl group, a 6-chloropyridazin-4-ylmethyl group, a 3-methylpyridazin-4-ylmethyl group, a 5-methylpyridazin-4-ylmethyl group, a 6-methylpyridazin-4-ylmethyl group, a 3-trifluoromethylpyridazin-4-ylmethyl group, a 5-trifluoromethylpyridazin-4-ylmethyl group, a 6-trifluoromethylpyridazin-4-ylmethyl group, a 3-methoxypyridazin-4-ylmethyl group, a pyrimidin-2-ylmethyl group,
4-chloropyrimidin-2-ylmethyl group, 5-chloropyrimidin-2-ylmethyl group, 4-methylpyrimidin-2-ylmethyl group, 5-methylpyrimidin-2-ylmethyl group, 4-trifluoromethylpyrimidin-2-ylmethyl group, 5-trifluoromethylpyrimidin-2-ylmethyl group, pyrimidin-4-ylmethyl group, 2-chloropyrimidin-4-ylmethyl group, 5-chloropyrimidin-4-ylmethyl group, 6-chloropyrimidin-4-ylmethyl group, 2-methylpyrimidin-4-ylmethyl group, 5-methylpyrimidin-4-ylmethyl group, 6-methylpyrimidin-4-ylmethyl group, 2- Trifluoromethylpyrimidin-4-ylmethyl group, 5-trifluoromethylpyrimidin-4-ylmethyl group, 6-trifluoromethylpyrimidin-4-ylmethyl group, pyrimidin-5-ylmethyl group, 2-chloropyrimidin-5-ylmethyl group, 4-chloropyrimidin-5-ylmethyl group, 6-chloropyrimidin-5-ylmethyl group, 2-methylpyrimidin-5-ylmethyl group, 4-methylpyrimidin-5-ylmethyl group, 6-methylpyrimidin-5-ylmethyl group, 2-trifluoromethylpyrimidin-5-ylmethyl group, 4-trifluoromethylpyrimidin-5-ylmethyl group, 6-trifluoromethylpyrimidin-5-ylmethyl group fluoromethylpyrimidin-5-ylmethyl group, pyrazin-2-ylmethyl group, 3-chloropyrazin-2-ylmethyl group, 5-chloropyrazin-2-ylmethyl group, 6-chloropyrazin-2-ylmethyl group, 3-methylpyrazin-2-ylmethyl group, 5-methylpyrazin-2-ylmethyl group, 6-methylpyrazin-2-ylmethyl group, 3-trifluoromethylpyrazin-2-ylmethyl group, 5-trifluoromethylpyrazin-2-ylmethyl group, 6-trifluoromethylpyrazin-2-ylmethyl group, 1-(pyridin-2-yl)ethyl group, 1-(3-chloropyridin-2-yl)ethyl group, 1-(4-chloropyrazin-2-yl)ethyl group, 1-(5-chloropyridin-2-yl)ethyl group, 1-(6-chloropyridin-2-yl)ethyl group, 1-(3-methylpyridin-2-yl)ethyl group, 1-(4-methylpyridin-2-yl)ethyl group, 1-(5-methylpyridin-2-yl)ethyl group, 1-(6-methylpyridin-2-yl)ethyl group, 1-(3-trifluoromethylpyridin-2-yl)ethyl group, 1-(4-trifluoromethylpyridin-2-yl)ethyl group, 1-(5-trifluoromethylpyridin-2-yl)ethyl group, 1-(6-trifluoromethylpyridin-2-yl)ethyl group,
1-(pyridin-3-yl)ethyl group, 1-(2-chloropyridin-3-yl)ethyl group, 1-(4-chloropyridin-3-yl)ethyl group, 1-(5-chloropyridin-3-yl)ethyl group, 1-(6-chloropyridin-3-yl)ethyl group, 1-(2-methylpyridin-3-yl)ethyl group, 1-(4-methylpyridin-3-yl)ethyl group, 1-(5-methylpyridin-3-yl)ethyl group, 1-(6-methylpyridin-3-yl)ethyl group, 1-(2-trifluoromethylpyridin-3-yl)ethyl group, 1-(4-trifluoromethylpyridin-3-yl)ethyl group, 1-(5-trifluoromethylpyridin-3-yl)ethyl group, 1-(6-trifluoromethylpyridin-3-yl)ethyl group, 1-(pyridazin-3-yl)ethyl group, 1-(pyridin-4-yl)ethyl group, 1-(2-chloropyridin-4-yl)ethyl group, 1-(3-chloropyridin-4-yl)ethyl group, 1-(2-methylpyridin-4-yl)ethyl group, 1-(3-methylpyridin-4-yl)ethyl group, 1-(2-trifluoromethylpyridin-4-yl)ethyl group, 1-(3-trifluoromethylpyridin-4-yl)ethyl group, 1-(pyridazin-3-yl)ethyl group, 1-(4-chloropyridazin-3-yl)methyl group, 1-(5-chloropyridazin-3-yl)ethyl group, 1-(6-chloropyridazin-3-yl)ethyl group, 1-(4-methylpyridazin-3-yl)ethyl group ethyl group, 1-(5-methylpyridazin-3-yl)ethyl group, 1-(6-methylpyridazin-3-yl)ethyl group, 1-(4-trifluoromethylpyridazin-3-yl)ethyl group, 1-(5-trifluoromethylpyridazin-3-yl)ethyl group, 1-(6-trifluoromethylpyridazin-3-yl)ethyl group, 1-(pyridazin-4-yl)ethyl group, 1-(3-chloropyridazin-4-yl)ethyl group, 1-(5-chloropyridazin-4-yl)ethyl group, 1-(6-chloropyridazin-4-yl)ethyl group, 1-(3-methylpyridazin-4-yl)ethyl group, 1-(5-methylpyridazin-4-yl)ethyl group, 1-(6-methylpyridazin-4-yl)ethyl group, ethyl group, 1-(3-trifluoromethylpyridazin-4-yl)ethyl group, 1-(5-trifluoromethylpyridazin-4-yl)ethyl group, 1-(6-trifluoromethylpyridazin-4-yl)ethyl group, 1-(pyrimidin-2-yl)ethyl group, 1-(4-chloropyrimidin-2-yl)ethyl group, 1-(5-chloropyrimidin-2-yl)ethyl group, 1-(4-methylpyrimidin-2-yl)ethyl group, 1-(5-methylpyrimidin-2-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-2-yl)ethyl group, 1-(pyrimidin-4-yl)ethyl group, 1-(2-chloropyrimidin 1-(2-methylpyrimidin-4-yl)ethyl group, 1-(5-methylpyrimidin-4-yl)ethyl group, 1-(6-methylpyrimidin-4-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(pyrimidin-5-yl)ethyl group, 1-(2-chloropyrimidin-5-yl)ethyl group, 1-(4-chloropyrimidin-5-yl)ethyl group, 1-(6-chloropyrimidin-4-yl)ethyl group, 1-(2-methylpyrimidin-4-yl)ethyl group, 1-(5-methylpyrimidin-4-yl)ethyl group, 1-(6-methylpyrimidin-4-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(5-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-4-yl)ethyl group, 1-(pyrimidin-5-yl)ethyl group, 1-(2-chloropyrimidin-5-yl)ethyl group, 1-(4-chloropyrimidin-5-yl)ethyl group, pyrimidin-5-yl)ethyl group, 1-(2-methylpyrimidin-5-yl)ethyl group, 1-(4-methylpyrimidin-5-yl)ethyl group, 1-(6-methylpyrimidin-5-yl)ethyl group, 1-(2-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(4-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(6-trifluoromethylpyrimidin-5-yl)ethyl group, 1-(pyrazin-2-yl)ethyl group, 1-(3-chloropyrazin-2-yl)ethyl group, 1-(5-chloropyrazin-2-yl)ethyl group, 1-(6-chloropyrazin-2-yl)ethyl group, 1-(3-methylpyrazin-2-yl)ethyl group, 1-(5-methylpyrazin 1-(6-methylpyrazin-2-yl)ethyl group, 1-(3-trifluoromethylpyrazin-2-yl)ethyl group, 1-(5-trifluoromethylpyrazin-2-yl)ethyl group, 1-(6-trifluoromethylpyrazin-2-yl)ethyl group, 3-methyl-1,2,4-oxadiazolyl group, 5-trifluoromethyl-3-methyl-1,2,4-oxadiazolyl group, thiazol-2-ylmethyl group, thiazol-4-ylmethyl group, thiazol-5-ylmethyl group, propan-2-one group, methoxycarbonylmethyl group, methoxycarbonylethyl group, ethoxycarbonylmethyl group, ethoxycarbonylethyl group, dimethylaminocarbonyl group, a 1,3-dioxolan-2-ylmethyl group, or a 3-(dihydrofuran-2(3H)-one)methyl group;
More preferred are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a cyanomethyl group, a 2-cyanoethyl group, a cyclopropylmethyl group, a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, and an ethoxyethyl group.
Particularly preferred is a methyl group or an ethyl group.
　式（１－２）のＲ２における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，２，２，２－テトラフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、２，２，３，３，３－ペンタフルオロプロピル基、１，１，２，２，３，３，３－ヘプタフルオロプロピル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、または２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基であり、さらに好ましくは、ジフルオロメチル基、２，２，２－トリフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、または１，１，２，２，３，３，３－ヘプタフルオロプロピル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、または２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基であり、特に好ましくは、ジフルオロメチル基、２，２，２－トリフルオロエチル基、２，２，３，３，３－ペンタフルオロプロピル基、または２，２，３，３，４，４，４－ヘプタフルオロブチル基である。 The "C1 to C6 haloalkyl group" in R2 of formula (1-2) is defined as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentaethyl group. is preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 1,1,2,2,3,3,3-heptafluoropropyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, and particularly preferably a difluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, or a 2,2,3,3,4,4,4-heptafluorobutyl group.
　式（１－２）のＲ２における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａに置換される。「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のシクロアルキル基」として好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、１－（シクロプロパン－１－カルボニトリル）基、２－（シクロプロパン－１－カルボニトリル）基、１－（１－ニトロシクロプロピル）基、１－（２－ニトロシクロプロピル）基、１－（１－シクロプロピルシクロプロピル）基、１－（２－シクロプロピルシクロプロピル）基、１－（２－メトキシシクロプロピル）基、１－（２－エトキシシクロプロピル）基、１－（１－フェニルシクロプロピル）基、１－（２－フェニルシクロプロピル）基、１－（シクロプロピルエタン－１－オン）基、２－（シクロプロピルエタン－１オン）基、１－（１－メトキシカルボニルシクロプロピル）基、１－（２－メトキシカルボニルシクロプロピル）基、１－（１－エトキシカルボニルシクロプロピル）基、または１－（２－エトキシカルボニルシクロプロピル）基であり、より好ましくは、シクロプロピル基、シクロブチル基、１－（シクロプロパン－１－カルボニトリル）基、２－（シクロプロパン－１－カルボニトリル）基、１－（１－ニトロシクロプロピル）基、１－（２－ニトロシクロプロピル）基、１－（１－メトキシカルボニルシクロプロピル）基、１－（２－メトキシカルボニルシクロプロピル）基、１－（１－エトキシカルボニルシクロプロピル）基、または１－（２－エトキシカルボニルシクロプロピル）基であり、さらに好ましくは、シクロプロピル基、１－（シクロプロパン－１－カルボニトリル）基、または１－（１－メトキシカルボニルシクロプロピル）基である。特に好ましくは、シクロプロピル基、または１－（シクロプロパン－１－カルボニトリル）基である。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) is as defined above and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A. Preferred examples of the "C1 to C6 cycloalkyl group which may be appropriately substituted with a substituent A" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-(cyclopropane-1-carbonitrile) group, a 2-(cyclopropane-1-carbonitrile) group, a 1-(1-nitrocyclopropyl) group, a 1-(2-nitrocyclopropyl) group, a 1-(1-cyclopropylcyclopropyl) group, a 1-(2-cyclopropylcyclopropyl) group, a 1-(2-methoxycyclopropyl) group, a 1-(2-ethoxycyclopropyl) group, a 1-(1-phenylcyclopropyl) group, a 1-(2-phenylcyclopropyl) group, a 1-(cyclopropylethan-1-one) group, a 2-(cyclopropylethan-1-one) group, a 1-(1-methoxycarbonylcyclopropyl) group, a 1-(2-methoxy cyclopropyl) group, 1-(1-ethoxycarbonylcyclopropyl) group, or 1-(2-ethoxycarbonylcyclopropyl) group, more preferably cyclopropyl group, cyclobutyl group, 1-(cyclopropane-1-carbonitrile) group, 2-(cyclopropane-1-carbonitrile) group, 1-(1-nitrocyclopropyl) group, 1-(2-nitrocyclopropyl) group, 1-(1-methoxycarbonylcyclopropyl) group, 1-(2-methoxycarbonylcyclopropyl) group, 1-(1-ethoxycarbonylcyclopropyl) group, or 1-(2-ethoxycarbonylcyclopropyl) group, and even more preferably cyclopropyl group, 1-(cyclopropane-1-carbonitrile) group, or 1-(1-methoxycarbonylcyclopropyl) group. Particularly preferably, it is a cyclopropyl group or a 1-(cyclopropane-1-carbonitrile) group.
　式（１－２）のＲ２における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、または３－ブテニル基であり、特に好ましくは、アリル基、２－メチルアリル基、または３－ブテニル基である。置換基Ａ記載中の置換基を有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) is the same as defined above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group. When it has a substituent as described in the substituent A, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
　式（１－２）のＲ２における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、３，３－ジフルオロアリル基である。 The "C2-C6 haloalkenyl group" in R2 of formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
　式（１－２）のＲ２における「置換基Ａで適宜置換されてよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、プロパルギル基、または２－ブチニル基であり、特に好ましくは、プロパルギル基、または２－ブチニル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R2 of formula (1-2) is as defined above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（１－２）のＲ２における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、または４，４，４－トリフルオロ－１－ブチニル基であり、特に好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2 to C6 haloalkynyl group" in R2 of formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（１－２）のＲ２における「置換基Ｂで適宜０～５置換されてよいフェニル基」はフェニル基における水素原子が独立した置換基Ｂによって１～５置換の間で任意に置換される。「置換基Ｂで適宜０～５置換されてよいフェニル基」として好ましくは、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、トルイル基、メトキシフェニル基、フェノキシフェニル基、メチルスルファニルフェニル基、メチルスルフィニルフェニル基、メチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、トリフルオロメチルスルフィニルフェニル基、またはトリフルオロメチルスルホニルフェニル基であり、さらに好ましくは、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、トルイル基、メトキシフェニル基、メチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、トリフルオロメチルスルフィニルフェニル基、またはトリフルオロメチルスルホニルフェニル基であり、特に好ましくは、フェニル基である。 The "phenyl group which may be optionally substituted with 0 to 5 substituents B" in R2 of formula (1-2) is a phenyl group in which hydrogen atoms are arbitrarily substituted with 1 to 5 independent substituents B. The "phenyl group which may be optionally substituted with 0 to 5 substituents B" is preferably a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a toluyl group, a methoxyphenyl group, a phenoxyphenyl group, a methylsulfanylphenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, more preferably a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a toluyl group, a methoxyphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, and particularly preferably a phenyl group.
　式（１－２）のＲ２における「置換基Ｂで適宜０～４置換されてよい５～６員芳香族複素環基」の５～６員芳香族複素環基は、前記の定義と同義であり、好ましくは、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基であり、さらに好ましくは、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、チエニル基、チアゾリル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、トリアゾリル基、オキサジアゾリル基であり、特に好ましくは、ピリジル基、またはピリミジニル基である。「置換基Ｂで適宜０～４置換されてよい５～６員芳香族複素環基」として好ましくは、ピリジル基、２－シアノピリジル基、３－シアノピリジル基、４－シアノピリジル基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－ヨードピリジル基、３－ヨードピリジル基、４－ヨードピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリダジニル基、３－シアノピリダジニル基、４－シアノピリダジニル基、３－フルオロピリダジニル基、４－フルオロピリダジニル基、３－クロロピリダジニル基、４－クロロピリダジニル基、３－ブロモピリダジニル基、４－ブロモピリダジニル基、３－ヨードピリダジニル基、４－ヨードピリダジニル基、３－メチルピリダジニル基、４－メチルピリダジニル基、３－トリフルオロメチルピリダジニル基、４－トリフルオロメチルピリダジニル基、３－メトキシピリダジニル基、４－メトキシピリダジニル基、ピリミジニル基、２－シアノピリミジニル基、４－シアノピリミジニル基、５－シアノピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－ブロモピリミジニル基、４－ブロモピリミジニル基、５－ブロモピリミジニル基、２－ヨードピリミジニル基、４－ヨードピリミジニル基、５－ヨードピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、５－メトキシピリミジニル基、ピラジニル基、２－シアノピラジニル基、２－フルオロピラジニル基、２－クロロピラジニル基、２－ブロモピラジニル基、２－ヨードピラジニル基、２－メチルピラジニル基、２－トリフルオロメチルピラジニル基、または２－メトキシピラジニル基であり、
　さらに好ましくは、ピリジル基、２－シアノピリジル基、３－シアノピリジル基、４－シアノピリジル基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－ヨードピリジル基、３－ヨードピリジル基、４－ヨードピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリミジル基、２－シアノピリミジニル基、４－シアノピリミジニル基、５－シアノピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－ブロモピリミジニル基、４－ブロモピリミジニル基、５－ブロモピリミジニル基、２－ヨードピリミジニル基、４－ヨードピリミジニル基、５－ヨードピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、または５－メトキシピリミジニル基であり、
特に好ましくは、ピリジル基、３－トリフルオロメチルピリジル基、またはピリミジル基である。 The 5- to 6-membered aromatic heterocyclic group of "a 5- to 6-membered aromatic heterocyclic group which may be appropriately substituted with 0 to 4 substituents B" in R2 of formula (1-2) is the same as defined above, and is preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group, more preferably a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, or an oxadiazolyl group, and particularly preferably a pyridyl group or a pyrimidinyl group. Preferred examples of the "5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" include a pyridyl group, a 2-cyanopyridyl group, a 3-cyanopyridyl group, a 4-cyanopyridyl group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-iodopyridyl group, a 3-iodopyridyl group, a 4-iodopyridyl group, a 2-methylpyridyl group, a 3-methylpyridyl group, a 4-methylpyridyl group, a 2-trifluoromethylpyridyl group, a pyridyl group, a 3-trifluoromethylpyridyl group, a 4-trifluoromethylpyridyl group, a 2-methoxypyridyl group, a 3-methoxypyridyl group, a 4-methoxypyridyl group, a pyridazinyl group, a 3-cyanopyridazinyl group, a 4-cyanopyridazinyl group, a 3-fluoropyridazinyl group, a 4-fluoropyridazinyl group, a 3-chloropyridazinyl group, a 4-chloropyridazinyl group, a 3-bromopyridazinyl group, a 4-bromopyridazinyl group, a 3-iodopyridazinyl group, a 4-iodopyridazinyl group, a 3-methylpyridazinyl group, a 4-methylpyridazinyl group, a 3-trifluoromethylpyridazinyl group, pyridazinyl group, 4-trifluoromethylpyridazinyl group, 3-methoxypyridazinyl group, 4-methoxypyridazinyl group, pyrimidinyl group, 2-cyanopyrimidinyl group, 4-cyanopyrimidinyl group, 5-cyanopyrimidinyl group, 2-fluoropyrimidinyl group, 4-fluoropyrimidinyl group, 5-fluoropyrimidinyl group, 2-chloropyrimidinyl group, 4-chloropyrimidinyl group, 5-chloropyrimidinyl group, 2-bromopyrimidinyl group, 4-bromopyrimidinyl group, 5-bromopyrimidinyl group, 2-iodopyrimidinyl group, 4-iodopyrimidinyl group, 5-iodopyrimidinyl a 2-methylpyrimidinyl group, a 4-methylpyrimidinyl group, a 5-methylpyrimidinyl group, a 2-trifluoromethylpyrimidinyl group, a 4-trifluoromethylpyrimidinyl group, a 5-trifluoromethylpyrimidinyl group, a 2-methoxypyrimidinyl group, a 4-methoxypyrimidinyl group, a 5-methoxypyrimidinyl group, a pyrazinyl group, a 2-cyanopyrazinyl group, a 2-fluoropyrazinyl group, a 2-chloropyrazinyl group, a 2-bromopyrazinyl group, a 2-iodopyrazinyl group, a 2-methylpyrazinyl group, a 2-trifluoromethylpyrazinyl group, or a 2-methoxypyrazinyl group;
More preferred are pyridyl, 2-cyanopyridyl, 3-cyanopyridyl, 4-cyanopyridyl, 2-fluoropyridyl, 3-fluoropyridyl, 4-fluoropyridyl, 2-chloropyridyl, 3-chloropyridyl, 4-chloropyridyl, 2-bromopyridyl, 3-bromopyridyl, 4-bromopyridyl, 2-iodopyridyl, 3-iodopyridyl, 4-iodopyridyl, 2-methylpyridyl, 3-methylpyridyl, 4-methylpyridyl, 2-trifluoromethylpyridyl, 3-trifluoromethylpyridyl, 4-trifluoromethylpyridyl, 2-methoxypyridyl, 3-methoxypyridyl, 4-methoxypyridyl, pyrimidyl, 2-cyanopyrimidinyl, 4-cyanopyrid ... an anopyrimidinyl group, a 5-cyanopyrimidinyl group, a 2-fluoropyrimidinyl group, a 4-fluoropyrimidinyl group, a 5-fluoropyrimidinyl group, a 2-chloropyrimidinyl group, a 4-chloropyrimidinyl group, a 5-chloropyrimidinyl group, a 2-bromopyrimidinyl group, a 4-bromopyrimidinyl group, a 5-bromopyrimidinyl group, a 2-iodopyrimidinyl group, a 4-iodopyrimidinyl group, a 5-iodopyrimidinyl group, a 2-methylpyrimidinyl group, a 4-methylpyrimidinyl group, a 5-methylpyrimidinyl group, a 2-trifluoromethylpyrimidinyl group, a 4-trifluoromethylpyrimidinyl group, a 5-trifluoromethylpyrimidinyl group, a 2-methoxypyrimidinyl group, a 4-methoxypyrimidinyl group, or a 5-methoxypyrimidinyl group;
Particularly preferred is a pyridyl group, a 3-trifluoromethylpyridyl group, or a pyrimidyl group.
　式（１－２）のＲ２におけるＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）の各用語は、前記と同義である。
　「Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－」として好ましくは、カルバモイル基、メチルカルボニル基、エチルカルバモイル基、プロピルカルバモイル基、イソプロピルカルバモイル基、ブチルカルバモイル基、イソブチルカルバモイル基、ｓｅｃ－ブチルカルバモイル基、ｔ－ブチルカルバモイル基、ペンチルカルバモイル基、イソペンチルカルバモイル基、２－メチルブチルカルバモイル基、ネオペンチルカルバモイル基、１－エチルプロピルカルバモイル基、ヘキシルカルバモイル基、メトキシメチルカルバモイル基、エトキシメチルカルバモイル基、プロピルオキシメチルカルバモイル基、イソプロピルオキシメチルカルバモイル基、２－メトキシエチルカルバモイル基、２－エトキシエチルカルバモイル基、シアノメチルカルバモイル基、１－シアノエチルカルバモイル基、２－シアノエチルカルバモイル基、シクロプロピルメチルカルバモイル基、シクロブチルメチルカルバモイル基、
ベンジルカルバモイル基、１－フェネチルカルバモイル基、１，１－ジフルオロエチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、２，２，２－トリフルオロエチルカルバモイル基、２，２，３，３，３－ペンタフルオロプロピルカルバモイル基、２，２，３，３，４，４，４－ヘプタフルオロブチルカルバモイル基、３，３，４，４，５，５，５－ヘプタフルオロペンチルカルバモイル基、シクロプロピルカルバモイル基、１－シアノシクロプロピルカルバモイル基、アリルカルバモイル基、３，３－ジフルオロアリルカルバモイル基、プロパルギルカルバモイル基、メトキシカルバモイル基、トリフルオロエトキシカルバモイル基、フェニルカルバモイル基、４－シアノフェニルカルバモイル基、２－フルオロフェニルカルバモイル基、３－フルオロフェニルカルバモイル基、４－フルオロフェニルカルバモイル基、２－クロロフェニルカルバモイル基、３－クロロフェニルカルバモイル基、４－クロロフェニルカルバモイル基、２－トリフルオロメチルフェニルカルバモイル基、３－トリフルオロメチルフェニルカルバモイル基、４－トリフルオロメチルフェニルカルバモイル基、２－メトキシフェニルカルバモイル基、３－メトキシフェニルカルバモイル基、４－メトキシフェニルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、
ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、
メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　より好ましくは、メチルカルボニル基、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　さらに好ましくは、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　特に好ましくは、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、イソブチルメチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基である。 Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group which may be optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.) each term has the same meaning as above.
Preferred examples of "Rx1Rx2NC(=O)-" include a carbamoyl group, a methylcarbonyl group, an ethylcarbamoyl group, a propylcarbamoyl group, an isopropylcarbamoyl group, a butylcarbamoyl group, an isobutylcarbamoyl group, a sec-butylcarbamoyl group, a t-butylcarbamoyl group, a pentylcarbamoyl group, an isopentylcarbamoyl group, a 2-methylbutylcarbamoyl group, a neopentylcarbamoyl group, a 1-ethylpropylcarbamoyl group, a hexylcarbamoyl group, a methoxymethylcarbamoyl group, an ethoxymethylcarbamoyl group, a propyloxymethylcarbamoyl group, an isopropyloxymethylcarbamoyl group, a 2-methoxyethylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a cyanomethylcarbamoyl group, a 1-cyanoethylcarbamoyl group, a 2-cyanoethylcarbamoyl group, a cyclopropylmethylcarbamoyl group, a cyclobutylmethylcarbamoyl group,
benzylcarbamoyl group, 1-phenethylcarbamoyl group, 1,1-difluoroethylcarbamoyl group, 2,2-difluoroethylcarbamoyl group, 2,2,2-trifluoroethylcarbamoyl group, 2,2,3,3,3-pentafluoropropylcarbamoyl group, 2,2,3,3,4,4,4-heptafluorobutylcarbamoyl group, 3,3,4,4,5,5,5-heptafluoropentylcarbamoyl group, cyclopropylcarbamoyl group, 1-cyanocyclopropylcarbamoyl group, Allylcarbamoyl group, 3,3-difluoroallylcarbamoyl group, propargylcarbamoyl group, methoxycarbamoyl group, trifluoroethoxycarbamoyl group, phenylcarbamoyl group, 4-cyanophenylcarbamoyl group, 2-fluorophenylcarbamoyl group, 3-fluorophenylcarbamoyl group, 4-fluorophenylcarbamoyl group, 2-chlorophenylcarbamoyl group, 3-chlorophenylcarbamoyl group, 4-chlorophenylcarbamoyl group, 2-trifluoromethyl Phenylcarbamoyl group, 3-trifluoromethylphenylcarbamoyl group, 4-trifluoromethylphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxyphenylcarbamoyl group, pyrrolidinecarbonyl group, piperidinecarbonyl group, piperazinecarbonyl group, morpholinecarbonyl group, thiomorpholinecarbonyl group, dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocane a carbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an ethylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, an isopropylethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, a butylethylcarbamoyl group, a sec-butylmethylcarbamoyl group, a sec-butylethylcarbamoyl group, an isobutylmethylcarbamoyl group, an isobutylethylcarbamoyl group,
t-butylmethylcarbamoyl group, t-butylethylcarbamoyl group, methylpentylcarbamoyl group, ethylpentylcarbamoyl group, isopentylmethylcarbamoyl group, isopentylethylcarbamoyl group, methyl(2-methylbutyl)carbamoyl group, ethyl(2-methylbutyl)carbamoyl group, hexylmethylcarbamoyl group, hexylethylcarbamoyl group, (methoxymethyl)methylcarbamoyl group, (ethoxymethyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, ( (ethoxyethyl)methylcarbamoyl group, (propyloxymethyl)methylcarbamoyl group, (isopropyloxymethyl)methylcarbamoyl group, (methoxymethyl)ethylcarbamoyl group, (ethoxymethyl)ethylcarbamoyl group, (cyanomethyl)methylcarbamoyl group, (cyanomethyl)ethylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pyridin-3-ylmethyl)carbamoyl group, a methyl(2,2,2-trifluoroethyl)carbamoyl group, a methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, a methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, a methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, a (cyclopropyl)methylcarbamoyl group, a (cyclopropyl)ethylcarbamoyl group, a (1-cyanocyclopropyl)methylcarbamoyl group, a (1-cyanocyclopropyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group,
a methyl(6-methyl-pyridin-2-yl)carbamoyl group, a methyl(pyridin-3-yl)carbamoyl group, or a methyl(pyridin-4-yl)carbamoyl group;
More preferably, a methylcarbonyl group, an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a piperazinecarbonyl group, a morpholinecarbonyl group, a thiomorpholinecarbonyl group, a dioxothiomorpholinecarbonyl group, a thiazolidinecarbonyl group, an azepanecarbonyl group, an azocanecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an ethylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, an isopropylethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, a butylethylcarbamoyl group, a sec-butylmethylcarbamoyl group, a sec-butylethylcarbamoyl group, an isobutylmethylcarbamoyl group, a methylcarbamoyl group, an isobutylethylcarbamoyl group, a t-butylmethylcarbamoyl group, a t-butylethylcarbamoyl group, a methylpentylcarbamoyl group, an ethylpentylcarbamoyl group, an isopentylmethylcarbamoyl group, an isopentylethylcarbamoyl group, a methyl(2-methylbutyl)carbamoyl group, an ethyl(2-methylbutyl)carbamoyl group, a hexylmethylcarbamoyl group, a hexylethylcarbamoyl group, a (methoxymethyl)methylcarbamoyl group, an (ethoxymethyl)methylcarbamoyl group, a (methoxyethyl)methylcarbamoyl group, an (ethoxyethyl)methylcarbamoyl group, a (propyloxymethyl)methylcarbamoyl group, an (isopropyloxymethyl)methylcarbamoyl group, a (methoxymethyl)ethylcarbamoyl group, an (ethoxymethyl)methylcarbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopropyl)ethylcarbamoyl group, (1-cyanocyclopropyl)methylcarbamoyl group, methylcarbamoyl group, (1-cyanocyclopropyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group,
More preferred are an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a morpholinecarbonyl group, a thiomorpholinecarbonyl group, a dioxothiomorpholinecarbonyl group, a thiazolidinecarbonyl group, an azepanecarbonyl group, an azocanecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, a butylethylcarbamoyl group, a sec-butylmethylcarbamoyl group, a sec-butylethylcarbamoyl group, an isobutylmethylcarbamoyl group, an isobutylethylcarbamoyl group, a t-butylmethylcarbamoyl group, a (methoxyethyl)methylcarbamoyl group, a (cyanomethyl)methylcarbamoyl group, a (cyanomethyl)ethylcarbamoyl group, a (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pyridin-3-ylmethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (pyridin-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group,
Particularly preferred are an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a morpholinecarbonyl group, a thiomorpholinecarbonyl group, a thiazolidinecarbonyl group, an azepanecarbonyl group, an azocanecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methylpropylcarbamoyl group, an isopropylmethylcarbamoyl group, a diisopropylcarbamoyl group, a butylmethylcarbamoyl group, an isobutylmethylcarbamoyl group, a t-butylmethylcarbamoyl group, a (methoxyethyl)methylcarbamoyl group, a (cyanomethyl)methylcarbamoyl group, and methyl(pyridin-3-yl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group.
　式（１－２）のＲ２における「Ｒｘ３Ｃ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３Ｃ（＝Ｏ）－」として好ましくは、アセチル基、１－シアノアセチル基、１－メトキシアセチル基、プロピオニル基、イソブチリル基、ジフルオロアセチル基、トリフルオロアセチル基、ベンゾイル基、４－フルオロベンゾイル基、または４－トリフルオロベンゾイル基であり、さらに好ましくは、アセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、またはベンゾイル基であり、特に好ましくはアセチル基、トリフルオロアセチル基、またはベンゾイル基である。 Each term in "Rx3C(=O)-" in R2 of formula (1-2) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. "Rx3C(=O)-" is preferably an acetyl group, a 1-cyanoacetyl group, a 1-methoxyacetyl group, a propionyl group, an isobutyryl group, a difluoroacetyl group, a trifluoroacetyl group, a benzoyl group, a 4-fluorobenzoyl group, or a 4-trifluorobenzoyl group, more preferably an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, or a benzoyl group, and particularly preferably an acetyl group, a trifluoroacetyl group, or a benzoyl group.
　式（１－２）のＲ２における「Ｒｘ３ＯＣ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３ＯＣ（＝Ｏ）－」として好ましくは、メトキシカルボニル基、エトキシカルボニル基、イソプロピルオキシカルボニル基、ジフルオロメトキシカルボニル基、トリフルオロメトキシカルボニル基、シクロプロピルオキシカルボニル基、シクロペンチルオキシカルボニル基、アリルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、さらに好ましくは、メトキシカルボニル基、エトキシカルボニル基、イソプロピルオキシカルボニル基、シクロプロピルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、特に好ましくは、メトキシカルボニル基、またはエトキシカルボニル基である。 Each term in "Rx3OC(=O)-" in R2 of formula (1-2) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. "Rx3OC(=O)-" is preferably a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a cyclopropyloxycarbonyl group, a cyclopentyloxycarbonyl group, an allyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, more preferably a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, a cyclopropyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, and particularly preferably a methoxycarbonyl group or an ethoxycarbonyl group.
　式（１－２）のＲ２における「Ｒｘ４Ｓ（Ｏ）ｐ－」（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）の各用語は、前記の定義と同義である。「Ｒｘ４Ｓ（Ｏ）ｐ－」として好ましくは、メチルスルホニル基、エチルスルホニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルホニル基、シクロペンチルスルホニル基、フェニルスルホニル基、４－フルオロフェニルスルホニル基、４－クロロフェニルスルホニル基、４－メチルフェニルスルホニル基、または４－トリフルオロメチルフェニルスルホニル基であり、さらに好ましくは、メチルスルホニル基、エチルスルホニル基、トリフルオロメチルスルホニル基、４－メチルフェニルスルホニル基、または４－トリフルオロメチルフェニルスルホニル基であり、特に好ましくは、メチルスルホニル基、エチルスルホニル基、または４－メチルフェニルスルホニル基である。 Each term in "Rx4S(O)p-" in R2 of formula (1-2) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) has the same meaning as defined above. "Rx4S(O)p-" is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group, a phenylsulfonyl group, a 4-fluorophenylsulfonyl group, a 4-chlorophenylsulfonyl group, a 4-methylphenylsulfonyl group, or a 4-trifluoromethylphenylsulfonyl group, more preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 4-methylphenylsulfonyl group, or a 4-trifluoromethylphenylsulfonyl group, and particularly preferably a methylsulfonyl group, an ethylsulfonyl group, or a 4-methylphenylsulfonyl group.
　式（１－２）のＲ２における「１～２個の酸素原子を含む３～６員環の基」の用語は、前記と同義である。「１～２個の酸素原子を含む３～６員環の基」として好ましくは、オキシラン－２－イル基、オキセタン－３－イル基、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、１，４－ジオキサン－２－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、４－ジヒドロフラン－２（３Ｈ）－オン基、３－テトラヒドロ－２Ｈ－ピラン－２－オン基、または４－テトラヒドロ－２Ｈ－ピラン－２－オン基であり、より好ましくは、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、または４－ジヒドロフラン－２（３Ｈ）－オン基であり、さらに好ましくは、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、または３－ジヒドロフラン－２（３Ｈ）－オン基であり、特に好ましくは、テトラヒドロ－２Ｈ－ピラン－４－イル基、または３－ジヒドロフラン－２（３Ｈ）－オン基である。 The term "3- to 6-membered ring group containing 1 to 2 oxygen atoms" in R2 of formula (1-2) has the same meaning as above. The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" is preferably an oxiran-2-yl group, an oxetan-3-yl group, a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 1,4-dioxan-2-yl group, a 3-dihydrofuran-2(3H)-one group, a 4-dihydrofuran-2(3H)-one group, a 3-tetrahydro-2H-pyran-2-one group, or a 4-tetrahydro-2H-pyran-2-one group, and more preferably a tetrahydro It is preferably a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 3-dihydrofuran-2(3H)-one group, or a 4-dihydrofuran-2(3H)-one group, more preferably a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-4-yl group, or a 3-dihydrofuran-2(3H)-one group, and particularly preferably a tetrahydro-2H-pyran-4-yl group, or a 3-dihydrofuran-2(3H)-one group.
　式（１－１）または式（１－２）中のＲ３は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表す。 R3 in formula (1-1) or formula (1-2) is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group; Rx3C(=O)- (wherein Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 aryl group optionally substituted with a substituent A) alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B. ), or Rx3OC(=O)- (wherein Rx3 has the same meaning as above).
　中でもＲ３は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）が好ましく、 Among them, R3 is preferably a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, Rx1Rx2NC(=O)- (where Rx3 has the same meaning as above), Rx3C(=O)- (where Rx3 has the same meaning as above), or Rx3OC(=O)- (where Rx3 has the same meaning as above),
　特にＲ３は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）が好ましく、 In particular, R3 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A,
C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with a substituent A, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above), Rx3C(=O)- (wherein Rx3 is as defined above), or Rx3OC(=O)- (wherein Rx3 is as defined above) are preferred;
　さらにＲ３は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）が好ましい。 R3 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent A,
Rx3C(=O)-- (wherein Rx3 has the same meaning as defined above) or Rx3OC(=O)-- (wherein Rx3 has the same meaning as defined above) is preferred.
　式（１－１）または式（１－２）のＲ３には、水素原子が含まれる。 R3 in formula (1-1) or formula (1-2) includes a hydrogen atom.
　式（１－１）または式（１－２）のＲ３における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、または１，２，２－トリメチルプロピル基であり、より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、またはイソペンチル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、特に好ましくは、メチル基、またはエチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with the substituent A" in R3 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethyl butyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, or 1,2,2-trimethylpropyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, or isopentyl group, even more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and particularly preferably methyl group or ethyl group. When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ３における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，２，２，２－テトラフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、または１，１，２，２，３，３，３－ヘプタフルオロプロピル基であり、さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基であり、特に好ましくは、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基である。 The "C1 to C6 haloalkyl group" in R3 of formula (1-1) or formula (1-2) is defined as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group, and particularly preferably a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
　式（１－１）または式（１－２）のＲ３における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基であり、さらに好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、特に好ましくは、シクロプロピル基、またはシクロブチル基である。置換基Ａ記載中の置換基を有する場合、Ｃ３～Ｃ８のシクロアルキル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R3 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and particularly preferably a cyclopropyl group or a cyclobutyl group. When it has a substituent as described for the substituent A, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with a substituent as described for the substituent A.
　式（１－１）または式（１－２）のＲ３における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、または３－ブテニル基であり、特に好ましくは、アリル基、２－メチルアリル基、または３－ブテニル基である。置換基Ａ記載中の置換基を有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R3 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group. When it has a substituent as described in the substituent A, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
　式（１－１）または式（１－２）のＲ３における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、３，３－ジフルオロアリル基である。 The "C2 to C6 haloalkenyl group" in R3 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
　式（１－１）または式（１－２）のＲ３における「置換基Ａで適宜置換されてよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、プロパルギル基、または２－ブチニル基であり、特に好ましくは、プロパルギル基、または２－ブチニル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R3 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ３における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、または４，４，４－トリフルオロ－１－ブチニル基であり、特に好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2 to C6 haloalkynyl group" in R3 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（１－１）または式（１－２）のＲ３におけるＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）の各用語は、前記と同義である。「Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－」として好ましくは、
カルバモイル基、メチルカルバモイル基、エチルカルバモイル基、プロピルカルバモイル基、イソプロピルカルバモイル基、ブチルカルバモイル基、イソブチルカルバモイル基、ｓｅｃ－ブチルカルバモイル基、ｔ－ブチルカルバモイル基、ペンチルカルバモイル基、イソペンチルカルバモイル基、２－メチルブチルカルバモイル基、ネオペンチルカルバモイル基、１－エチルプロピルカルバモイル基、ヘキシルカルバモイル基、メトキシメチルカルバモイル基、エトキシメチルカルバモイル基、プロピルオキシメチルカルバモイル基、イソプロピルオキシメチルカルバモイル基、２－メトキシエチルカルバモイル基、２－エトキシエチルカルバモイル基、シアノメチルカルバモイル基、１－シアノエチルカルバモイル基、２－シアノエチルカルバモイル基、シクロプロピルメチルカルバモイル基、シクロブチルメチルカルバモイル基、ベンジルカルバモイル基、１－フェネチルカルバモイル基、１－ジフルオロエチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、２，２，２－トリフルオロエチルカルバモイル基、２，２，３，３，３－ペンタフルオロプロピルカルバモイル基、２，２，３，３，４，４，４－ヘプタフルオロブチルカルバモイル基、３，３，４，４，５，５，５－ヘプタフルオロペンチルカルバモイル基、シクロプロピルカルバモイル基、１－シアノシクロプロピルカルバモイル基、アリルカルバモイル基、３，３－ジフルオロアリルカルバモイル基、プロパルギルカルバモイル基、メトキシカルバモイル基、トリフルオロエトキシカルバモイル基、フェニルカルバモイル基、４－シアノフェニルカルバモイル基、２－フルオロフェニルカルバモイル基、３－フルオロフェニルカルバモイル基、４－フルオロフェニルカルバモイル基、２－クロロフェニルカルバモイル基、３－クロロフェニルカルバモイル基、４－クロロフェニルカルバモイル基、２－トリフルオロメチルフェニルカルバモイル基、３－トリフルオロメチルフェニルカルバモイル基、４－トリフルオロメチルフェニルカルバモイル基、２－メトキシフェニルカルバモイル基、３－メトキシフェニルカルバモイル基、４－メトキシフェニルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　より好ましくは、カルバモイル基、メチルカルバモイル基、エチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、４－シアノピペリジンカルボニル基、４－フルオロピペリジンカルボニル基、４，４－ジフルオロピペリジンカルボニル基、４－メチルピペリジンカルボニル基、４－トリフルオロメチルピペリジンカルボニル基、４－メトキシカルボニルピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、
（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、メチル（ピリジン－４－イル）カルバモイル基であり、
　特に好ましくは、カルバモイル基、メチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ジメチルカルバモイル基、またはエチルメチルカルバモイル基である。 Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy group) , a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group.) are as defined above. As "Rx1Rx2NC(=O)-", preferably,
Carbamoyl group, methylcarbamoyl group, ethylcarbamoyl group, propylcarbamoyl group, isopropylcarbamoyl group, butylcarbamoyl group, isobutylcarbamoyl group, sec-butylcarbamoyl group, t-butylcarbamoyl group, pentylcarbamoyl group, isopentylcarbamoyl group, 2-methylbutylcarbamoyl group, neopentylcarbamoyl group, 1-ethylpropylcarbamoyl group, hexylcarbamoyl group, methoxymethylcarbamoyl group, ethoxymethylcarbamoyl group, propyloxymethylcarbamoyl group, isopropyloxymethylcarbamoyl group, 2-methoxyethylcarbamoyl group, 2-ethyl a methoxyethylcarbamoyl group, a cyanomethylcarbamoyl group, a 1-cyanoethylcarbamoyl group, a 2-cyanoethylcarbamoyl group, a cyclopropylmethylcarbamoyl group, a cyclobutylmethylcarbamoyl group, a benzylcarbamoyl group, a 1-phenethylcarbamoyl group, a 1-difluoroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group, a 2,2,2-trifluoroethylcarbamoyl group, a 2,2,3,3,3-pentafluoropropylcarbamoyl group, a 2,2,3,3,4,4,4-heptafluorobutylcarbamoyl group, a 3,3,4,4,5,5,5-heptafluoropentylcarbamoyl group, a cyclopropyl a propylcarbamoyl group, a 1-cyanocyclopropylcarbamoyl group, an allylcarbamoyl group, a 3,3-difluoroallylcarbamoyl group, a propargylcarbamoyl group, a methoxycarbamoyl group, a trifluoroethoxycarbamoyl group, a phenylcarbamoyl group, a 4-cyanophenylcarbamoyl group, a 2-fluorophenylcarbamoyl group, a 3-fluorophenylcarbamoyl group, a 4-fluorophenylcarbamoyl group, a 2-chlorophenylcarbamoyl group, a 3-chlorophenylcarbamoyl group, a 4-chlorophenylcarbamoyl group, a 2-trifluoromethylphenylcarbamoyl group, a 3-trifluoromethylphenylcarbamoyl group, a moyl group, 4-trifluoromethylphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxyphenylcarbamoyl group, pyrrolidinecarbonyl group, piperidinecarbonyl group, piperazinecarbonyl group, morpholinecarbonyl group, thiomorpholinecarbonyl group, dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocanecarbonyl group, dimethylcarbamoyl group, ethylmethylcarbamoyl group, diethylcarbamoyl group, methylpropylcarbamoyl group, ethylpropylcarbamoyl group, isopropylmethylcarbamoyl group, isopropylethylcarbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, butylethylcarbamoyl group, sec-butylmethylcarbamoyl group, sec-butylethylcarbamoyl group, isobutylmethylcarbamoyl group, isobutylethylcarbamoyl group, t-butylmethylcarbamoyl group, t-butylethylcarbamoyl group, methylpentylcarbamoyl group, ethylpentylcarbamoyl group, isopentylmethylcarbamoyl group, isopentylethylcarbamoyl group, methyl(2-methylbutyl)carbamoyl group, ethyl(2-methylbutyl)carbamoyl group, hexylmethylcarbamoyl group, Hexylethylcarbamoyl group, (methoxymethyl)methylcarbamoyl group, (ethoxymethyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, (ethoxyethyl)methylcarbamoyl group, (propyloxymethyl)methylcarbamoyl group, (isopropyloxymethyl)methylcarbamoyl group, (methoxymethyl)ethylcarbamoyl group, (ethoxymethyl)ethylcarbamoyl group, (cyanomethyl)methylcarbamoyl group, (cyanomethyl)ethylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl a methyl(pyridin-3-ylmethyl)carbamoyl group, a methyl(2,2,2-trifluoroethyl)carbamoyl group, a methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, a methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, a methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, a (cyclopropyl)methylcarbamoyl group, a (cyclopropyl)ethylcarbamoyl group, a (1-cyanocyclopropyl)methylcarbamoyl group, a (1-cyanocyclopropyl)ethylcarbamoyl group, a (cyclobutyl)methylcarbamoyl group, a (cyclopentyl) a methyl(2-propyn-1-yl)carbamoyl group, a (cyclohexyl)methylcarbamoyl group, a (allyl)methylcarbamoyl group, a methyl(2-propyn-1-yl)carbamoyl group, an ethyl(2-propyn-1-yl)carbamoyl group, a (methoxy)methylcarbamoyl group, a (ethoxy)methylcarbamoyl group, a (trifluoroethoxy)methylcarbamoyl group, a methylphenylcarbamoyl group, a diphenylcarbamoyl group, a methyl(pyridin-2-yl)carbamoyl group, a methyl(6-methyl-pyridin-2-yl)carbamoyl group, a methyl(pyridin-3-yl)carbamoyl group, or a methyl(pyridin-4-yl)carbamoyl group;
More preferably, a carbamoyl group, a methylcarbamoyl group, an ethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a 4-cyanopiperidinecarbonyl group, a 4-fluoropiperidinecarbonyl group, a 4,4-difluoropiperidinecarbonyl group, a 4-methylpiperidinecarbonyl group, a 4-trifluoromethylpiperidinecarbonyl group, a 4-methoxycarbonylpiperidinecarbonyl group, a piperazinecarbonyl group, a morpholinecarbonyl group, a thiomorphoyl group, or a methylpiperidinecarbonyl group is preferably a methylpiperidinecarbonyl group. phosphoruscarbonyl group, dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocanecarbonyl group, dimethylcarbamoyl group, ethylmethylcarbamoyl group, diethylcarbamoyl group, methylpropylcarbamoyl group, ethylpropylcarbamoyl group, isopropylmethylcarbamoyl group, isopropylethylcarbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, butylethylcarbamoyl group, sec -butylmethylcarbamoyl group, sec-butylethylcarbamoyl group, isobutylmethylcarbamoyl group, isobutylethylcarbamoyl group, t-butylmethylcarbamoyl group, t-butylethylcarbamoyl group, methylpentylcarbamoyl group, ethylpentylcarbamoyl group, isopentylmethylcarbamoyl group, isopentylethylcarbamoyl group, methyl(2-methylbutyl)carbamoyl group, ethyl(2-methylbutyl)carbamoyl group, hexylmethyl carbamoyl group, hexylethylcarbamoyl group, (methoxymethyl)methylcarbamoyl group, (ethoxymethyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, (ethoxyethyl)methylcarbamoyl group, (propyloxymethyl)methylcarbamoyl group, (isopropyloxymethyl)methylcarbamoyl group, (methoxymethyl)ethylcarbamoyl group, (ethoxymethyl)ethylcarbamoyl group, (cyanomethyl)methylcarbamoyl group,
(cyanomethyl)ethylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pyridin-3-ylmethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopropyl)ethylcarbamoyl group, (1-cyanocyclopropyl)methylcarbamoyl group, (1-cyanocyclopropyl)methylcarbamoyl group, and the like. Examples of the above-listed groups include (propyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, and methyl(pyridin-4-yl)carbamoyl group.
Particularly preferred are a carbamoyl group, a methylcarbamoyl group, a pyrrolidine carbonyl group, a piperidine carbonyl group, a dimethylcarbamoyl group, and an ethylmethylcarbamoyl group.
　式（１－１）または式（１－２）のＲ３における「Ｒｘ３Ｃ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３Ｃ（＝Ｏ）－」として好ましくは、ホルミル基、アセチル基、プロピオニル基、イソプロピオニル基、ブチリル基、イソブチリル基、ｔ－ブチリル基、ペンタノイル基、ヘキサノイル基、（１Ｈ－ピラゾール－１－イル）アセチル基、（１Ｈ－１，２，４－トリアゾール－１－イル）アセチル基、２－フルオロアセチル基、２－クロロアセチル基、２－ブロモアセチル基、２，２－ジフルオロアセチル基、２，２－ジクロロアセチル基、２，２－ジブロモアセチル基、２，２，２－トリフルオロアセチル基、２－クロロ－２，２－ジフルオロアセチル基、２，２，２－トリクロロアセチル基、２，２，３，３－テトラフルオロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基、２，２－ジフルオロプロピオニル基、３，３，３－トリフルオロプロピオニル基、２，２，３，３，４，４－ヘキサフルオロブチリル基、２，２，３，３，４，４，４－ヘプタフルオロブチリル基、２，２，３，３，４，４，５，５－オクタフルオロペンタノイル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンタノイル基、２，２，３，３，４，４，５，５，６，６－デカフルオロヘキサノイル基、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキサノイル基、シクロプロピオニル基、シクロブチリル基、シクロペンチノイル基、シクロヘキサノイル基、ベンゾイル基、２－フルオロベンゾイル基、３－フルオロベンゾイル基、４－フルオロベンゾイル基、２－クロロベンゾイル基、３－クロロベンゾイル基、４－クロロベンゾイル基、２－ブロモベンゾイル基、３－ブロモベンゾイル基、４－ブロモベンゾイル基、２－メチルベンゾイル基、３－メチルベンゾイル基、４－メチルベンゾイル基、２－トリフルオロメチルベンゾイル基、３－トリフルオロメチルベンゾイル基、４－トリフルオロメチルベンゾイル基、ピコリノイル基、ニコチノイル基、またはイソニコチノイル基であり、
より好ましくは、アセチル基、プロピオニル基、イソプロピオニル基、ブチリル基、イソブチリル基、ｔ－ブチリル基、ペンタノイル基、ヘキサノイル基、２－（１Ｈ－ピラゾール－１－イル）アセチル基、２－（１Ｈ－１，２，４－トリアゾール－１－イル）アセチル基、２－クロロアセチル基、２，２－ジフルオロアセチル基、２，２－ジクロロアセチル基、２，２－ジブロモアセチル基、２，２，２－トリフルオロアセチル基、２－クロロ－２，２－ジフルオロアセチル基、２，２，２－トリクロロアセチル基、２，２，３，３－テトラフルオロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基、２，２－ジフルオロプロピオニル基、３，３，３－トリフルオロプロピオニル基、２，２，３，３，４，４－ヘキサフルオロブチリル基、２，２，３，３，４，４，４－ヘプタフルオロブチリル基、２，２，３，３，４，４，５，５－オクタフルオロペンタノイル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンタノイル基、２，２，３，３，４，４，５，５，６，６－デカフルオロヘキサノイル基、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキサノイル基、シクロプロピオニル基、シクロブチリル基、シクロペンチノイル基、シクロヘキサノイル基、ベンゾイル基、２－フルオロベンゾイル基、３－フルオロベンゾイル基、４－フルオロベンゾイル基、２－クロロベンゾイル基、３－クロロベンゾイル基、４－クロロベンゾイル基、２－トリフルオロメチルベンゾイル基、３－トリフルオロメチルベンゾイル基、４－トリフルオロメチルベンゾイル基、ピコリノイル基、ニコチノイル基、またはイソニコチノイル基であり、
さらに好ましくは、アセチル基、プロピオニル基、イソプロピオニル基、ブチリル基、イソブチリル基、ｔ－ブチリル基、ペンタノイル基、ヘキサノイル基、２－（１Ｈ－ピラゾール－１－イル）アセチル基、２－（１Ｈ－１，２，４－トリアゾール－１－イル）アセチル基、２－クロロアセチル基、２，２－ジフルオロアセチル基、２，２－ジクロロアセチル基、２，２－ジブロモアセチル基、２，２，２－トリフルオロアセチル基、２－クロロ－２，２－ジフルオロアセチル基、２，２，２－トリクロロアセチル基、２，２，３，３－テトラフルオロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基、２，２－ジフルオロプロピオニル基、３，３，３－トリフルオロプロピオニル基、２，２，３，３，４，４－ヘキサフルオロブチリル基、２，２，３，３，４，４，４－ヘプタフルオロブチリル基、２，２，３，３，４，４，５，５－オクタフルオロペンタノイル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンタノイル基、２，２，３，３，４，４，５，５，６，６－デカフルオロヘキサノイル基、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキサノイル基、シクロプロピオニル基、ベンゾイル基、ピコリノイル基、またはニコチノイル基であり、
　特に好ましくは、アセチル基、またはシクロプロピオニル基である。 Each term in "Rx3C(=O)-" in R3 of formula (1-1) or formula (1-2) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be appropriately substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be appropriately substituted with 0 to 4 substituents B) has the same meaning as defined above. Preferred examples of "Rx3C(=O)-" include a formyl group, an acetyl group, a propionyl group, an isopropionyl group, a butyryl group, an isobutyryl group, a t-butyryl group, a pentanoyl group, a hexanoyl group, a (1H-pyrazol-1-yl)acetyl group, a (1H-1,2,4-triazol-1-yl)acetyl group, a 2-fluoroacetyl group, a 2-chloroacetyl group, a 2-bromoacetyl group, a 2,2-difluoroacetyl group, a 2,2-dichloroacetyl group, a 2,2-dibutyryl group, a 2-phenylacetyl ... bromoacetyl group, 2,2,2-trifluoroacetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2,2-trichloroacetyl group, 2,2,3,3-tetrafluoropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoropropionyl group, 2,2,3,3,4,4-hexafluorobutyryl group, 2,2,3,3,4,4,4-heptafluorobutyryl group, 2,2,3 ,3,4,4,5,5-octafluoropentanoyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl group, 2,2,3,3,4,4,5,5,6,6-decafluorohexanoyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, cyclopropionyl group, cyclobutyryl group, cyclopentynoyl group, cyclohexanoyl group, benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4 2-fluorobenzoyl group, 2-chlorobenzoyl group, 3-chlorobenzoyl group, 4-chlorobenzoyl group, 2-bromobenzoyl group, 3-bromobenzoyl group, 4-bromobenzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 2-trifluoromethylbenzoyl group, 3-trifluoromethylbenzoyl group, 4-trifluoromethylbenzoyl group, picolinoyl group, nicotinoyl group, or isonicotinoyl group;
More preferred are an acetyl group, a propionyl group, an isopropionyl group, a butyryl group, an isobutyryl group, a t-butyryl group, a pentanoyl group, a hexanoyl group, a 2-(1H-pyrazol-1-yl)acetyl group, a 2-(1H-1,2,4-triazol-1-yl)acetyl group, a 2-chloroacetyl group, a 2,2-difluoroacetyl group, a 2,2-dichloroacetyl group, a 2,2-dibromoacetyl group, a 2 , 2,2-trifluoroacetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2,2-trichloroacetyl group, 2,2,3,3-tetrafluoropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoropropionyl group, 2,2,3,3,4,4-hexafluorobutyryl group, 2,2,3,3,4,4,4- heptafluorobutyryl group, 2,2,3,3,4,4,5,5-octafluoropentanoyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl group, 2,2,3,3,4,4,5,5,6,6-decafluorohexanoyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, cyclopropionyl group, cyclobutyryl group, cyclopentynoyl group, cyclohexanoyl group, benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4-fluorobenzoyl group, 2-chlorobenzoyl group, 3-chlorobenzoyl group, 4-chlorobenzoyl group, 2-trifluoromethylbenzoyl group, 3-trifluoromethylbenzoyl group, 4-trifluoromethylbenzoyl group, picolinoyl group, nicotinoyl group, or isonicotinoyl group;
More preferred are an acetyl group, a propionyl group, an isopropionyl group, a butyryl group, an isobutyryl group, a t-butyryl group, a pentanoyl group, a hexanoyl group, a 2-(1H-pyrazol-1-yl)acetyl group, a 2-(1H-1,2,4-triazol-1-yl)acetyl group, a 2-chloroacetyl group, a 2,2-difluoroacetyl group, a 2,2-dichloroacetyl group, a 2,2-dibromoacetyl group, a 2,2,2-trifluoroacetyl group, a 2-chloro-2,2-difluoroacetyl group, a 2,2,2-trichloroacetyl group, a 2,2,3,3-tetrafluoropropionyl group, a 2,2,3,3,3-pentafluoroacetyl group, and a 2,2-difluoropropionyl group, a 3,3,3-trifluoropropionyl group, a 2,2,3,3,4,4-hexafluorobutyryl group, a 2,2,3,3,4,4,4-heptafluorobutyryl group, a 2,2,3,3,4,4,5,5-octafluoropentanoyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl group, a 2,2,3,3,4,4,5,5,6,6-decafluorohexanoyl group, a 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, a cyclopropionyl group, a benzoyl group, a picolinoyl group, or a nicotinoyl group;
Particularly preferred is an acetyl group or a cyclopropionyl group.
　式（１－１）または式（１－２）のＲ３における「Ｒｘ３ＯＣ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３ＯＣ（＝Ｏ）－」として好ましくは、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、ｔ－ブチルオキシカルボニル基、ジフルオロメトキシカルボニル基、トリフルオロメトキシカルボニル基、シクロプロピルオキシカルボニル基、シクロペンチルオキシカルボニル基、アリルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、より好ましくは、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、ｔ－ブチルオキシカルボニル基、シクロプロピルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、さらに好ましくは、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、またはｔ－ブチルオキシカルボニル基であり、特に好ましくは、メトキシカルボニル基である。 Each term in "Rx3OC(=O)-" in R3 of formula (1-1) or formula (1-2) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. "Rx3OC(=O)-" is preferably a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a t-butyloxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a cyclopropyloxycarbonyl group, a cyclopentyloxycarbonyl group, an allyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, more preferably a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a t-butyloxycarbonyl group, a cyclopropyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, even more preferably a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, or a t-butyloxycarbonyl group, and particularly preferably a methoxycarbonyl group.
　式（１－１）または式（１－２）中のＲ４は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表す。 R4 in formula (1-1) or formula (1-2) is a hydrogen atom, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1 to C6 alkoxy group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be appropriately substituted with a substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with a substituent A, a C2 to C6 haloalkynyl group, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are, each independently represents a hydrogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or R x1 and Rx2, together with the nitrogen atom to which they are bonded, represent an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.), Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a substituent A represents a C2-C6 alkynyl group optionally substituted with, a C2-C6 haloalkynyl group, a phenyl group optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B. ), Rx3OC(=O)- (wherein Rx3 has the same meaning as above), or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group [the 5- to 6-membered partially unsaturated heterocyclic ring or the 8- to 10-membered partially unsaturated heterocyclic ring is optionally substituted with 0-6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent independent substituents or may be the same to form a 3- to 6-membered ring. )].
　中でもＲ４は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕が好ましく、 Among them, R4 is a hydrogen atom, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1 to C6 alkoxy group which may be appropriately substituted with a substituent A, a C1 to C6 haloalkoxy group, a C2 to C6 alkenyl group which may be appropriately substituted with a substituent A, a C2 to C6 alkynyl group which may be appropriately substituted with a substituent A, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above. ), Rx3C(=O)- (wherein Rx3 has the same meaning as above), Rx3OC(=O)- (wherein Rx3 has the same meaning as above), or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group [the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent, or may be the same to form a 3- to 6-membered ring)] is preferred,
　特にＲ４は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕が好ましく、 R4 is preferably a hydrogen atom, a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C1-C6 alkoxy group which may be substituted with a substituent A, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above), Rx3C(=O)- (wherein Rx3 is as defined above), Rx3OC(=O)- (wherein Rx3 is as defined above), or a 5- to 6-membered partially unsaturated heterocyclic group or an 8- to 10-membered partially unsaturated heterocyclic group [the 5- to 6-membered partially unsaturated heterocyclic ring or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent independent substituents or may be the same to form a 3- to 6-membered ring). ],
　さらにＲ４は、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕が好ましい。 Furthermore, R4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 have the same meanings as above), or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group [the 5- to 6-membered partially unsaturated heterocyclic ring or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent independent substituents or may be the same to form a 3- to 6-membered ring). ].
　式（１－１）または式（１－２）のＲ４には、水素原子が含まれる。 R4 in formula (1-1) or formula (1-2) includes a hydrogen atom.
　式（１－１）または式（１－２）のＲ４における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、または１，２，２－トリメチルプロピル基であり、より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、またはイソペンチル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、特に好ましくは、メチル基、エチル基、またはプロピル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with the substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethylbutyl group, group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, or 1,2,2-trimethylpropyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, or isopentyl group, even more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and particularly preferably methyl group, ethyl group, or propyl group. When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ４における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、モノクロロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、１，２，２，３，３，４，４，４－オクタフルオロブチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、３，３，４，４，５，５，５－ヘプタフルオロペンチル基、２，３，３，４，４，５，５，５－オクタフルオロペンチル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基、ウンデカフルオロペンチル基、トリデカフルオロヘキシル基であり、より好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、ジブロモメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、１，２，２，３，３，４，４，４－オクタフルオロブチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、３，３，４，４，５，５，５－ヘプタフルオロペンチル基、２，３，３，４，４，５，５，５－オクタフルオロペンチル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基、ウンデカフルオロペンチル基、またはトリデカフルオロヘキシル基であり、さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、１，２，２，３，３，４，４，４－オクタフルオロブチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、ウンデカフルオロペンチル基、またはトリデカフルオロヘキシル基であり、特に好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、クロロジフルオロメチル基、ジクロロフルオロメチル基、１，１－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、ヘプタフルオロプロピル基、またはノナフルオロブチル基である。 The "C1 to C6 haloalkyl group" in R4 of formula (1-1) or formula (1-2) has the same meaning as defined above, and is preferably a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-tri ... a fluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 2,3,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, ethyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,2,2,3,3,4,4,4-octafluorobutyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, 2,3,3,4,4,5,5,5-octafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, undecafluoropentyl group, tridecafluorohexyl group, more preferably difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, dibromomethyl group , diiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl 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, 1,2,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2,2,2-trichloroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 2,3,3,3-tetrafluoro propyl group, 2,2,3,3,3-pentafluoropropyl group, 1,2,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,2,2,3,3,4,4,4-octafluorobutyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, 2,3,3,4,4,5,5,5-octafluoropentyl group, 2,2,3,3 , 4,4,5,5,5-nonafluoropentyl group, undecafluoropentyl group, or tridecafluorohexyl group, and more preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 2,3,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,2,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,2,2,3,3,4,4,4-octafluorobutyl group, nonafluorobutyl group, nonafluoro -sec-butyl group, undecafluoropentyl group, or tridecafluorohexyl group, and particularly preferred are difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, chlorodifluoromethyl group, dichlorofluoromethyl group, 1,1-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,2,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, heptafluoropropyl group, or nonafluorobutyl group.
　式（１－１）または式（１－２）のＲ４における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基であり、より好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロヘキシル基であり、特に好ましくは、シクロプロピル基である。置換基Ａ記載中の置換基を有する場合、Ｃ３～Ｃ８のシクロアルキル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, even more preferably a cyclopropyl group or a cyclohexyl group, and particularly preferably a cyclopropyl group. When the C3-C8 cycloalkyl group has a substituent as described for the substituent A, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted with a substituent as described for the substituent A.
　式（１－１）または式（１－２）のＲ４における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、ｔ－ブトキシ基であり、さらに好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、またはｔ－ブトキシ基であり、特に好ましくは、メトキシ基、またはｔ－ブトキシ基である。置換基Ａ記載中の置換基を有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C1 to C6 alkoxy group in the "C1 to C6 alkoxy group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, or a t-butoxy group, more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a t-butoxy group, and particularly preferably a methoxy group or a t-butoxy group. When it has a substituent as described for the substituent A, the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with a substituent as described for the substituent A.
　式（１－１）または式（１－２）のＲ４における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、さらに好ましくは、トリフルオロメトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、特に好ましくは、トリフルオロメトキシ基、または１，１，２，２，２－ペンタフルオロエトキシ基である。 The "C1 to C6 haloalkoxy group" in R4 of formula (1-1) or formula (1-2) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a trifluoromethoxy group or a 1,1,2,2,2-pentafluoroethoxy group.
　式（１－１）または式（１－２）のＲ４における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基であり、特に好ましくは、シクロプロピルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ４における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、または３－ブテニル基であり、特に好ましくは、アリル基、２－メチルアリル基、または３－ブテニル基である。置換基Ａ記載中の置換基を有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group. When it has a substituent as described in the substituent A, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
　式（１－１）または式（１－２）のＲ４における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、３，３－ジフルオロアリル基である。 The "C2 to C6 haloalkenyl group" in R4 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
　式（１－１）または式（１－２）のＲ４における「置換基Ａで適宜置換されてよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、プロパルギル基、または２－ブチニル基であり、特に好ましくは、プロパルギル基、または２－ブチニル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R4 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ４における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、または４，４，４－トリフルオロ－１－ブチニル基であり、特に好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2 to C6 haloalkynyl group" in R4 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（１－１）または式（１－２）のＲ４におけるＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）の各用語は、前記と同義である。「Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－」として好ましくは、カルバモイル基、メチルカルバモイル基、エチルカルバモイル基、プロピルカルバモイル基、イソプロピルカルバモイル基、ブチルカルバモイル基、イソブチルカルバモイル基、ｓｅｃ－ブチルカルバモイル基、ｔ－ブチルカルバモイル基、ペンチルカルバモイル基、イソペンチルカルバモイル基、２－メチルブチルカルバモイル基、ネオペンチルカルバモイル基、１－エチルプロピルカルバモイル基、ヘキシルカルバモイル基、メトキシメチルカルバモイル基、エトキシメチルカルバモイル基、プロピルオキシメチルカルバモイル基、イソプロピルオキシメチルカルバモイル基、２－メトキシエチルカルバモイル基、２－エトキシエチルカルバモイル基、シアノメチルカルバモイル基、１－シアノエチルカルバモイル基、２－シアノエチルカルバモイル基、シクロプロピルメチルカルバモイル基、シクロブチルメチルカルバモイル基、ベンジルカルバモイル基、１－フェネチルカルバモイル基、１－ジフルオロエチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、２，２，２－トリフルオロエチルカルバモイル基、２，２，３，３，３－ペンタフルオロプロピルカルバモイル基、２，２，３，３，４，４，４－ヘプタフルオロブチルカルバモイル基、３，３，４，４，５，５，５－ヘプタフルオロペンチルカルバモイル基、シクロプロピルカルバモイル基、１－シアノシクロプロピルカルバモイル基、アリルカルバモイル基、３，３－ジフルオロアリルカルバモイル基、プロパルギルカルバモイル基、メトキシカルバモイル基、トリフルオロエトキシカルバモイル基、フェニルカルバモイル基、４－シアノフェニルカルバモイル基、２－フルオロフェニルカルバモイル基、３－フルオロフェニルカルバモイル基、４－フルオロフェニルカルバモイル基、２－クロロフェニルカルバモイル基、３－クロロフェニルカルバモイル基、４－クロロフェニルカルバモイル基、２－トリフルオロメチルフェニルカルバモイル基、３－トリフルオロメチルフェニルカルバモイル基、４－トリフルオロメチルフェニルカルバモイル基、２－メトキシフェニルカルバモイル基、３－メトキシフェニルカルバモイル基、４－メトキシフェニルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、（ネオペンチル）メチルカルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２－ジフルオロエチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（アリル）メチルカルバモイル基、メチル（２－プロピン－１－イル）カルバモイル基、エチル（２－プロピン－１－イル）カルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基、メチルフェニルカルバモイル基、ジフェニルカルバモイル基、メチル（ピリジン－２－イル）カルバモイル基、メチル（６－メチル－ピリジン－２－イル）カルバモイル基、メチル（ピリジン－３－イル）カルバモイル基、またはメチル（ピリジン－４－イル）カルバモイル基であり、
　より好ましくは、カルバモイル基、メチルカルバモイル基、エチルカルバモイル基、プロピルカルバモイル基、イソプロピルカルバモイル基、ブチルカルバモイル基、イソブチルカルバモイル基、ｓｅｃ－ブチルカルバモイル基、ｔ－ブチルカルバモイル基、ペンチルカルバモイル基、イソペンチルカルバモイル基、２－メチルブチルカルバモイル基、ネオペンチルカルバモイル基、１－エチルプロピルカルバモイル基、ヘキシルカルバモイル基、メトキシメチルカルバモイル基、エトキシメチルカルバモイル基、プロピルオキシメチルカルバモイル基、イソプロピルオキシメチルカルバモイル基、２－メトキシエチルカルバモイル基、２－エトキシエチルカルバモイル基、シアノメチルカルバモイル基、１－シアノエチルカルバモイル基、２－シアノエチルカルバモイル基、シクロプロピルメチルカルバモイル基、シクロブチルメチルカルバモイル基、ベンジルカルバモイル基、１－フェネチルカルバモイル基、１－ジフルオロエチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、２，２，２－トリフルオロエチルカルバモイル基、２，２，３，３，３－ペンタフルオロプロピルカルバモイル基、２，２，３，３，４，４，４－ヘプタフルオロブチルカルバモイル基、３，３，４，４，５，５，５－ヘプタフルオロペンチルカルバモイル基、シクロプロピルカルバモイル基、１－シアノシクロプロピルカルバモイル基、アリルカルバモイル基、３，３－ジフルオロアリルカルバモイル基、プロパルギルカルバモイル基、メトキシカルバモイル基、トリフルオロエトキシカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、ピペラジンカルボニル基、モルホリンカルボニル基、チオモルホリンカルボニル基、ジオキソチオモルホリンカルボニル基、チアゾリジンカルボニル基、アゼパンカルボニル基、アゾカンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、エチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、イソプロピルエチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、ブチルエチルカルバモイル基、ｓｅｃ－ブチルメチルカルバモイル基、ｓｅｃ－ブチルエチルカルバモイル基、イソブチルメチルカルバモイル基、イソブチルエチルカルバモイル基、ｔ－ブチルメチルカルバモイル基、ｔ－ブチルエチルカルバモイル基、メチルペンチルカルバモイル基、エチルペンチルカルバモイル基、イソペンチルメチルカルバモイル基、イソペンチルエチルカルバモイル基、メチル（２－メチルブチル）カルバモイル基、（ネオペンチル）メチルカルバモイル基、エチル（２－メチルブチル）カルバモイル基、ヘキシルメチルカルバモイル基、ヘキシルエチルカルバモイル基、（メトキシメチル）メチルカルバモイル基、（エトキシメチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（エトキシエチル）メチルカルバモイル基、（プロピルオキシメチル）メチルカルバモイル基、（イソプロピルオキシメチル）メチルカルバモイル基、（メトキシメチル）エチルカルバモイル基、（エトキシメチル）エチルカルバモイル基、（シアノメチル）メチルカルバモイル基、（シアノメチル）エチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、（シクロプロピルメチル）エチルカルバモイル基、（ベンジル）メチルカルバモイル基、メチル（ピリジン－３－イルメチル）カルバモイル基、メチル（２，２－ジフルオロエチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、メチル（２，２，３，３，３－ペンタフルオロプロピル）カルバモイル基、メチル（２，２，３，３，４，４，４－ヘプタフルオロブチル）カルバモイル基、メチル（３，３，４，４，５，５，５－ヘプタフルオロペンチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（シクロプロピル）エチルカルバモイル基、（１－シアノシクロプロピル）メチルカルバモイル基、（１－シアノシクロプロピル）エチルカルバモイル基、（シクロブチル）メチルカルバモイル基、（シクロペンチル）メチルカルバモイル基、（シクロヘキシル）メチルカルバモイル基、（メトキシ）メチルカルバモイル基、（エトキシ）メチルカルバモイル基、（トリフルオロエトキシ）メチルカルバモイル基であり、
　さらに好ましくは、カルバモイル基、メチルカルバモイル基、エチルカルバモイル基、プロピルカルバモイル基、イソプロピルカルバモイル基、ブチルカルバモイル基、イソブチルカルバモイル基、ペンチルカルバモイル基、ネオペンチルカルバモイル基、２－メトキシエチルカルバモイル基、シクロプロピルメチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、ピロリジンカルボニル基、ピペリジンカルボニル基、モルホリンカルボニル基、ジメチルカルバモイル基、エチルメチルカルバモイル基、ジエチルカルバモイル基、メチルプロピルカルバモイル基、イソプロピルメチルカルバモイル基、ジイソプロピルカルバモイル基、ブチルメチルカルバモイル基、イソブチルメチルカルバモイル基、メチルペンチルカルバモイル基、（ネオペンチル）メチルカルバモイル基、（メトキシエチル）メチルカルバモイル基、（シクロプロピルメチル）メチルカルバモイル基、メチル（２，２－ジフルオロエチル）カルバモイル基、メチル（２，２，２－トリフルオロエチル）カルバモイル基、（シクロプロピル）メチルカルバモイル基、（メトキシ）メチルカルバモイル基であり、
　特に好ましくは、ジメチルカルバモイル基、またはジエチルカルバモイル基である。 Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy group) , a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group.) have the same meaning as defined above. Preferred examples of "Rx1Rx2NC(=O)-" include a carbamoyl group, a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, an isopropylcarbamoyl group, a butylcarbamoyl group, an isobutylcarbamoyl group, a sec-butylcarbamoyl group, a t-butylcarbamoyl group, a pentylcarbamoyl group, an isopentylcarbamoyl group, a 2-methylbutylcarbamoyl group, a neopentylcarbamoyl group, a 1-ethylpropylcarbamoyl group, a hexylcarbamoyl group, a methoxymethylcarbamoyl group, an ethoxymethylcarbamoyl group, a propyloxymethylcarbamoyl group, an isopropyloxymethylcarbamoyl group, a 2-methylbutylcarbamoyl group, a 1-ethylpropylcarbamoyl group, a hexylcarbamoyl group, a methoxymethylcarbamoyl group, a ...methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group, a methoxymethylcarbamoyl group methoxyethylcarbamoyl group, 2-ethoxyethylcarbamoyl group, cyanomethylcarbamoyl group, 1-cyanoethylcarbamoyl group, 2-cyanoethylcarbamoyl group, cyclopropylmethylcarbamoyl group, cyclobutylmethylcarbamoyl group, benzylcarbamoyl group, 1-phenethylcarbamoyl group, 1-difluoroethylcarbamoyl group, 2,2-difluoroethylcarbamoyl group, 2,2,2-trifluoroethylcarbamoyl group, 2,2,3,3,3-pentafluoropropylcarbamoyl group, 2,2,3,3,4,4,4-heptafluorobutylcarbamoyl group, 3,3,4,4,5,5,5-heptafluoropentylcarbamoyl group, a cyclopropylcarbamoyl group, a 1-cyanocyclopropylcarbamoyl group, an allylcarbamoyl group, a 3,3-difluoroallylcarbamoyl group, a propargylcarbamoyl group, a methoxycarbamoyl group, a trifluoroethoxycarbamoyl group, a phenylcarbamoyl group, a 4-cyanophenylcarbamoyl group, a 2-fluorophenylcarbamoyl group, a 3-fluorophenylcarbamoyl group, a 4-fluorophenylcarbamoyl group, a 2-chlorophenylcarbamoyl group, a 3-chlorophenylcarbamoyl group, a 4-chlorophenylcarbamoyl group, a 2-trifluoromethylphenylcarbamoyl group, a 3-trifluoromethylphenylcarbamoyl group, azocarbonyl group, 4-trifluoromethylphenylcarbamoyl group, 2-methoxyphenylcarbamoyl group, 3-methoxyphenylcarbamoyl group, 4-methoxyphenylcarbamoyl group, pyrrolidinecarbonyl group, piperidinecarbonyl group, piperazinecarbonyl group, morpholinecarbonyl group, thiomorpholinecarbonyl group, dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocanecarbonyl group, dimethylcarbamoyl group, ethylmethylcarbamoyl group, diethylcarbamoyl group, methylpropylcarbamoyl group, ethylpropylcarbamoyl group, isopropylmethylcarbamoyl group, isopropylethylcarbamoyl group, carbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, butylethylcarbamoyl group, sec-butylmethylcarbamoyl group, sec-butylethylcarbamoyl group, isobutylmethylcarbamoyl group, isobutylethylcarbamoyl group, t-butylmethylcarbamoyl group, t-butylethylcarbamoyl group, methylpentylcarbamoyl group, ethylpentylcarbamoyl group, isopentylmethylcarbamoyl group, isopentylethylcarbamoyl group, methyl(2-methylbutyl)carbamoyl group, (neopentyl)methylcarbamoyl group, ethyl(2-methylbutyl)carbamoyl group, hexylmethylcarbamoyl group , hexylethylcarbamoyl group, (methoxymethyl)methylcarbamoyl group, (ethoxymethyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, (ethoxyethyl)methylcarbamoyl group, (propyloxymethyl)methylcarbamoyl group, (isopropyloxymethyl)methylcarbamoyl group, (methoxymethyl)ethylcarbamoyl group, (ethoxymethyl)ethylcarbamoyl group, (cyanomethyl)methylcarbamoyl group, (cyanomethyl)ethylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pi (lysine-3-ylmethyl)carbamoyl group, methyl(2,2-difluoroethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, methyl(3,3,4,4,5,5,5-heptafluoropentyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopropyl)ethylcarbamoyl group, (1-cyanocyclopropyl)methylcarbamoyl group, (1-cyanocyclopropyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group , (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (allyl)methylcarbamoyl group, methyl(2-propyn-1-yl)carbamoyl group, ethyl(2-propyn-1-yl)carbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group, methylphenylcarbamoyl group, diphenylcarbamoyl group, methyl(pyridin-2-yl)carbamoyl group, methyl(6-methyl-pyridin-2-yl)carbamoyl group, methyl(pyridin-3-yl)carbamoyl group, or methyl(pyridin-4-yl)carbamoyl group,
More preferred are a carbamoyl group, a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, an isopropylcarbamoyl group, a butylcarbamoyl group, an isobutylcarbamoyl group, a sec-butylcarbamoyl group, a t-butylcarbamoyl group, a pentylcarbamoyl group, an isopentylcarbamoyl group, a 2-methylbutylcarbamoyl group, a neopentylcarbamoyl group, a 1-ethylpropylcarbamoyl group, a hexylcarbamoyl group, a methoxymethylcarbamoyl group, an ethoxymethylcarbamoyl group, a procarbamoyl group, a propyl ... a propyloxymethylcarbamoyl group, an isopropyloxymethylcarbamoyl group, a 2-methoxyethylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a cyanomethylcarbamoyl group, a 1-cyanoethylcarbamoyl group, a 2-cyanoethylcarbamoyl group, a cyclopropylmethylcarbamoyl group, a cyclobutylmethylcarbamoyl group, a benzylcarbamoyl group, a 1-phenethylcarbamoyl group, a 1-difluoroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group, a 2,2,2-trifluoroethyl carbamoyl group, 2,2,3,3,3-pentafluoropropylcarbamoyl group, 2,2,3,3,4,4,4-heptafluorobutylcarbamoyl group, 3,3,4,4,5,5,5-heptafluoropentylcarbamoyl group, cyclopropylcarbamoyl group, 1-cyanocyclopropylcarbamoyl group, allylcarbamoyl group, 3,3-difluoroallylcarbamoyl group, propargylcarbamoyl group, methoxycarbamoyl group, trifluoroethoxycarbamoyl group, pyrrolidinecarbonyl group, piperidinecarbamoyl group, nyl group, piperazinecarbonyl group, morpholinecarbonyl group, thiomorpholinecarbonyl group, dioxothiomorpholinecarbonyl group, thiazolidinecarbonyl group, azepanecarbonyl group, azocanecarbonyl group, dimethylcarbamoyl group, ethylmethylcarbamoyl group, diethylcarbamoyl group, methylpropylcarbamoyl group, ethylpropylcarbamoyl group, isopropylmethylcarbamoyl group, isopropylethylcarbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, butylethyl Carbamoyl group, sec-butylmethylcarbamoyl group, sec-butylethylcarbamoyl group, isobutylmethylcarbamoyl group, isobutylethylcarbamoyl group, t-butylmethylcarbamoyl group, t-butylethylcarbamoyl group, methylpentylcarbamoyl group, ethylpentylcarbamoyl group, isopentylmethylcarbamoyl group, isopentylethylcarbamoyl group, methyl(2-methylbutyl)carbamoyl group, (neopentyl)methylcarbamoyl group, ethyl(2-methylbutyl)carbamoyl group , hexylmethylcarbamoyl group, hexylethylcarbamoyl group, (methoxymethyl)methylcarbamoyl group, (ethoxymethyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, (ethoxyethyl)methylcarbamoyl group, (propyloxymethyl)methylcarbamoyl group, (isopropyloxymethyl)methylcarbamoyl group, (methoxymethyl)ethylcarbamoyl group, (ethoxymethyl)ethylcarbamoyl group, (cyanomethyl)methylcarbamoyl group, (cyanomethyl)ethylcarbamoyl group methylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, (cyclopropylmethyl)ethylcarbamoyl group, (benzyl)methylcarbamoyl group, methyl(pyridin-3-ylmethyl)carbamoyl group, methyl(2,2-difluoroethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, methyl(2,2,3,3,3-pentafluoropropyl)carbamoyl group, methyl(2,2,3,3,4,4,4-heptafluorobutyl)carbamoyl group, methyl(3,3,4,4,5,5 , 5-heptafluoropentyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (cyclopropyl)ethylcarbamoyl group, (1-cyanocyclopropyl)methylcarbamoyl group, (1-cyanocyclopropyl)ethylcarbamoyl group, (cyclobutyl)methylcarbamoyl group, (cyclopentyl)methylcarbamoyl group, (cyclohexyl)methylcarbamoyl group, (methoxy)methylcarbamoyl group, (ethoxy)methylcarbamoyl group, (trifluoroethoxy)methylcarbamoyl group,
More preferred are a carbamoyl group, a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, an isopropylcarbamoyl group, a butylcarbamoyl group, an isobutylcarbamoyl group, a pentylcarbamoyl group, a neopentylcarbamoyl group, a 2-methoxyethylcarbamoyl group, a cyclopropylmethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group, a pyrrolidinecarbonyl group, a piperidinecarbonyl group, a morpholinecarbonyl group, a dimethylcarbamoyl group, an ethylmethylcarbamoyl group, a diethylcarbamoyl group, a methyl ... methylpropylcarbamoyl group, isopropylmethylcarbamoyl group, diisopropylcarbamoyl group, butylmethylcarbamoyl group, isobutylmethylcarbamoyl group, methylpentylcarbamoyl group, (neopentyl)methylcarbamoyl group, (methoxyethyl)methylcarbamoyl group, (cyclopropylmethyl)methylcarbamoyl group, methyl(2,2-difluoroethyl)carbamoyl group, methyl(2,2,2-trifluoroethyl)carbamoyl group, (cyclopropyl)methylcarbamoyl group, (methoxy)methylcarbamoyl group,
Particularly preferred is a dimethylcarbamoyl group or a diethylcarbamoyl group.
　式（１－１）または式（１－２）のＲ４における「Ｒｘ３Ｃ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３Ｃ（＝Ｏ）－」として好ましくは、ホルミル基、アセチル基、プロピオニル基、イソプロピオニル基、ブチリル基、イソブチリル基、ｔ－ブチリル基、ペンタノイル基、ヘキサノイル基、（１Ｈ－ピラゾール－１－イル）アセチル基、（１Ｈ－１，２，４－トリアゾール－１－イル）アセチル基、２－フルオロアセチル基、２－クロロアセチル基、２－ブロモアセチル基、２，２－ジフルオロアセチル基、２，２－ジクロロアセチル基、２，２－ジブロモアセチル基、２，２，２－トリフルオロアセチル基、２－クロロ－２，２－ジフルオロアセチル基、２，２，２－トリクロロアセチル基、２，２，３，３－テトラフルオロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基、２，２－ジフルオロプロピオニル基、３，３，３－トリフルオロプロピオニル基、２，２，３，３，４，４－ヘキサフルオロブチリル基、２，２，３，３，４，４，４－ヘプタフルオロブチリル基、２，２，３，３，４，４，５，５－オクタフルオロペンタノイル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンタノイル基、２，２，３，３，４，４，５，５，６，６－デカフルオロヘキサノイル基、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキサノイル基、シクロプロピオニル基、シクロブチリル基、シクロペンチノイル基、シクロヘキサノイル基、ベンゾイル基、２－フルオロベンゾイル基、３－フルオロベンゾイル基、４－フルオロベンゾイル基、２－クロロベンゾイル基、３－クロロベンゾイル基、４－クロロベンゾイル基、２－ブロモベンゾイル基、３－ブロモベンゾイル基、４－ブロモベンゾイル基、２－メチルベンゾイル基、３－メチルベンゾイル基、４－メチルベンゾイル基、２－トリフルオロメチルベンゾイル基、３－トリフルオロメチルベンゾイル基、４－トリフルオロメチルベンゾイル基、ピコリノイル基、ニコチノイル基、またはイソニコチノイル基であり、より好ましくは、アセチル基、プロピオニル基、イソプロピオニル基、ブチリル基、イソブチリル基、ｔ－ブチリル基、ペンタノイル基、ヘキサノイル基、２－（１Ｈ－ピラゾール－１－イル）アセチル基、２－（１Ｈ－１，２，４－トリアゾール－１－イル）アセチル基、２－クロロアセチル基、２，２－ジフルオロアセチル基、２，２－ジクロロアセチル基、２，２－ジブロモアセチル基、２，２，２－トリフルオロアセチル基、２－クロロ－２，２－ジフルオロアセチル基、２，２，２－トリクロロアセチル基、２，２，３，３－テトラフルオロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基、２，２－ジフルオロプロピオニル基、３，３，３－トリフルオロプロピオニル基、２，２，３，３，４，４－ヘキサフルオロブチリル基、２，２，３，３，４，４，４－ヘプタフルオロブチリル基、２，２，３，３，４，４，５，５－オクタフルオロペンタノイル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンタノイル基、２，２，３，３，４，４，５，５，６，６－デカフルオロヘキサノイル基、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキサノイル基、シクロプロピオニル基、ベンゾイル基、ピコリノイル基、またはニコチノイル基であり、さらに好ましくは、アセチル基、プロピオニル基、イソプロピオニル基、ブチリル基、イソブチリル基、ｔ－ブチリル基、２－（１Ｈ－ピラゾール－１－イル）アセチル基、２－（１Ｈ－１，２，４－トリアゾール－１－イル）アセチル基、２－クロロアセチル基、２，２－ジフルオロアセチル基、２，２－ジクロロアセチル基、２，２，２－トリフルオロアセチル基、２－クロロ－２，２－ジフルオロアセチル基、２，２，３，３－テトラフルオロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基、２，２－ジフルオロプロピオニル基、３，３，３－トリフルオロプロピオニル基、２，２，３，３，４，４，４－ヘプタフルオロブチリル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンタノイル基、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキサノイル基、シクロプロピオニル基、ベンゾイル基、ピコリノイル基、またはニコチノイル基であり、特に好ましくは、アセチル基、またはシクロプロピオニル基である。 Each term in "Rx3C(=O)-" in R4 of formula (1-1) or formula (1-2) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. Preferred examples of "Rx3C(=O)-" include a formyl group, an acetyl group, a propionyl group, an isopropionyl group, a butyryl group, an isobutyryl group, a t-butyryl group, a pentanoyl group, a hexanoyl group, a (1H-pyrazol-1-yl)acetyl group, a (1H-1,2,4-triazol-1-yl)acetyl group, a 2-fluoroacetyl group, a 2-chloroacetyl group, a 2-bromoacetyl group, a 2,2-difluoroacetyl group, a 2,2-dichloroacetyl group, a 2,2-dibromoacetyl group, a 2,2,2-trifluoroacetyl group, and a 2,2,2-trifluoroacetyl group. Acetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2,2-trichloroacetyl group, 2,2,3,3-tetrafluoropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoropropionyl group, 2,2,3,3,4,4-hexafluorobutyryl group, 2,2,3,3,4,4,4-heptafluorobutyryl group, 2,2,3,3,4,4,5,5-octafluoropentanoyl group, 2,2,3,3,4,4,5, 5,5-nonafluoropentanoyl group, 2,2,3,3,4,4,5,5,6,6-decafluorohexanoyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, cyclopropionyl group, cyclobutyryl group, cyclopentynoyl group, cyclohexanoyl group, benzoyl group, 2-fluorobenzoyl group, 3-fluorobenzoyl group, 4-fluorobenzoyl group, 2-chlorobenzoyl group, 3-chlorobenzoyl group, 4-chlorobenzoyl group, 2-bromobenzoyl group, 3-bromobenzoyl group, 4-bromobenzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 2-trifluoromethylbenzoyl group, 3-trifluoromethylbenzoyl group, 4-trifluoromethylbenzoyl group, picolinoyl group, nicotinoyl group, or isonicotinoyl group, and more preferably, acetyl group, propionyl group, isopropionyl group, butyryl group, isobutyryl group, t-butyryl group, pentanoyl group, hexanoyl group, 2-(1H-pyrazole)- ... 2-(1H-1,2,4-triazol-1-yl)acetyl group, 2-chloroacetyl group, 2,2-difluoroacetyl group, 2,2-dichloroacetyl group, 2,2-dibromoacetyl group, 2,2,2-trifluoroacetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2,2-trichloroacetyl group, 2,2,3,3-tetrafluoropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoroacetyl group, fluoropropionyl group, 2,2,3,3,4,4-hexafluorobutyryl group, 2,2,3,3,4,4,4-heptafluorobutyryl group, 2,2,3,3,4,4,5,5-octafluoropentanoyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl group, 2,2,3,3,4,4,5,5,6,6-decafluorohexanoyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, cyclopropionyl group, benzoyl group, picolinoyl group, or is a nicotinoyl group, and more preferably an acetyl group, a propionyl group, an isopropionyl group, a butyryl group, an isobutyryl group, a t-butyryl group, a 2-(1H-pyrazol-1-yl)acetyl group, a 2-(1H-1,2,4-triazol-1-yl)acetyl group, a 2-chloroacetyl group, a 2,2-difluoroacetyl group, a 2,2-dichloroacetyl group, a 2,2,2-trifluoroacetyl group, a 2-chloro-2,2-difluoroacetyl group, a 2,2,3,3-tetrafluoropropionyl group, a 2,2, 3,3,3-pentafluoropropionyl group, 2,2-difluoropropionyl group, 3,3,3-trifluoropropionyl group, 2,2,3,3,4,4,4-heptafluorobutyryl group, 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoyl group, cyclopropionyl group, benzoyl group, picolinoyl group, or nicotinoyl group, and particularly preferably acetyl group or cyclopropionyl group.
　式（１－１）または式（１－２）のＲ４における「Ｒｘ３ＯＣ（＝Ｏ）－」（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）の各用語は、前記の定義と同義である。「Ｒｘ３ＯＣ（＝Ｏ）－」として好ましくは、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、ｔ－ブチルオキシカルボニル基、ジフルオロメトキシカルボニル基、トリフルオロメトキシカルボニル基、シクロプロピルオキシカルボニル基、シクロペンチルオキシカルボニル基、アリルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、さらに好ましくは、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、イソプロピルオキシカルボニル基、ｔ－ブチルオキシカルボニル基、シクロプロピルオキシカルボニル基、プロパルギルオキシカルボニル基、フェニルオキシカルボニル基、または４－ニトロフェニルオキシカルボニル基であり、特に好ましくは、メトキシカルボニル基、エトキシカルボニル基、プロピルオキシカルボニル基、またはｔ－ブチルオキシカルボニル基であり、さらに好ましくは、メトキシカルボニル基である。 Each term in "Rx3OC(=O)-" in R4 of formula (1-1) or formula (1-2) (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be appropriately substituted with substituent A, a C2 to C6 alkenyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be appropriately substituted with substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a 5 to 6 membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B) has the same meaning as defined above. "Rx3OC(=O)-" is preferably a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a t-butyloxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a cyclopropyloxycarbonyl group, a cyclopentyloxycarbonyl group, an allyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, more preferably a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a t-butyloxycarbonyl group, a cyclopropyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, particularly preferably a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, or a t-butyloxycarbonyl group, and more preferably a methoxycarbonyl group.
　式（１－１）または式（１－２）のＲ４における「５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基」〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕の各用語は、前記の定義と同義である。「５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基」として好ましくは、ピロリン環基、ピラゾリン環基、イミダゾリン環基、オキサゾリン環基、チアゾリン環基、イソキサゾリン環基、オキサジン環基、またはチオオキサジン環基であり、該ピロリン環基、該ピラゾリン環基、該イミダゾリン環基、該オキサゾリン環基、該チアゾリン環基、該イソキサゾリン環基、該オキサジン環基、または該チオオキサジン環基は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。さらに好ましくは、オキサゾリン環基、またはイソキサゾリン環基であり、該オキサゾリン環基、または該イソキサゾリン環基は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。特に好ましくは、イソキサゾリン環基であり、該イソキサゾリン環基は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。
　「５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基」中のイソキサゾリン環基として好ましくは、〔化７〕に示される、式（４－１）、式（４－２）、式（４－３）、式（４－４）、式（４－５）、式（４－６）、または式（４－７）で表される構造であり（ここで式中、置換基Ｂは存在していないか、存在している場合は前記と同義である。）、
Figure JPOXMLDOC01-appb-C000009
　さらに好ましくは、［化８］に示される構造式であり、
Figure JPOXMLDOC01-appb-C000010
　特に好ましくは、［化９］に示される構造式である。
Figure JPOXMLDOC01-appb-C000011
 Each term in the "5- to 6-membered partially unsaturated heterocyclic group, or 8- to 10-membered partially unsaturated heterocyclic group" in R4 of formula (1-1) or formula (1-2) [the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring)] has the same meaning as defined above. The "5- to 6-membered partially unsaturated heterocyclic group or 8- to 10-membered partially unsaturated heterocyclic group" is preferably a pyrroline ring group, a pyrazoline ring group, an imidazoline ring group, an oxazoline ring group, a thiazoline ring group, an isoxazoline ring group, an oxazine ring group, or a thiooxazine ring group, and the pyrroline ring group, the pyrazoline ring group, the imidazoline ring group, the oxazoline ring group, the thiazoline ring group, the isoxazoline ring group, the oxazine ring group, or the thiooxazine ring group is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent independent substituents or may be the same to form a 3- to 6-membered ring). More preferred is an oxazoline ring group or an isoxazoline ring group, and the oxazoline ring group or the isoxazoline ring group is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring.) Particularly preferred is an isoxazoline ring group, and the isoxazoline ring group is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituted substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring.).
The isoxazoline ring group in the "5- to 6-membered partially unsaturated heterocyclic group or 8- to 10-membered partially unsaturated heterocyclic group" is preferably a structure represented by formula (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), or (4-7) shown in [Chemical Formula 7] (wherein, in the formula, the substituent B is absent or, if present, has the same meaning as above).
Figure JPOXMLDOC01-appb-C000009
More preferably, it is a structural formula shown in [Chemical Formula 8],
Figure JPOXMLDOC01-appb-C000010
Particularly preferred is the structural formula shown in [Chemical Formula 9].
Figure JPOXMLDOC01-appb-C000011
　式（１－１）または式（１－２）中のＲ５は、シアノ基、  ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表す。 R5 in formula (1-1) or formula (1-2) is a cyano group, a halogen atom, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or Rx4S(O)p- (where Rx4 is hydrogen). represents an acid group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2.)
　中でもＲ５は、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）が好ましく、 Among them, R5 is preferably a cyano group, a halogen atom, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A, or Rx4S(O)p- (where Rx4 and p are as defined above),
　特にＲ５は、シアノ基、ハロゲン原子、    置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）が好ましく、 In particular, R5 is preferably a cyano group, a halogen atom, a C1-C6 alkoxy group optionally substituted with a substituent A, or Rx4S(O)p- (where Rx4 and p are as defined above),
　さらにＲ５は、Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）が好ましい。 Furthermore, R5 is preferably Rx4S(O)p- (wherein Rx4 and p are as defined above).
　式（１－１）または式（１－２）のＲ５には、シアノ基が含まれる。 R5 in formula (1-1) or formula (1-2) includes a cyano group.
　式（１－１）または式（１－２）のＲ５におけるハロゲン原子は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子であり、さらに好ましくは、フッ素原子、塩素原子、または臭素原子であり、特に好ましくは、フッ素原子、または塩素原子である。 The halogen atom in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom or a chlorine atom.
　式（１－１）または式（１－２）のＲ５における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、ｔ－ブトキシ基であり、さらに好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、またはｔ－ブトキシ基であり、特に好ましくは、メトキシ基、またはエトキシ基である。置換基Ａ記載中の置換基を有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C1 to C6 alkoxy group in the "C1 to C6 alkoxy group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) is the same as defined above, and is preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, or a t-butoxy group, more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a t-butoxy group, and particularly preferably a methoxy group or an ethoxy group. When it has a substituent as described for the substituent A, the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with a substituent as described for the substituent A.
　式（１－１）または式（１－２）のＲ５における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、さらに好ましくは、トリフルオロメトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、特に好ましくは、トリフルオロメトキシ基、２，２，２－トリフルオロエトキシ基、または１，１，２，２，２－ペンタフルオロエトキシ基である。 The "C1 to C6 haloalkoxy group" in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, or a 1,1,2,2,2-pentafluoroethoxy group.
　式（１－１）または式（１－２）のＲ５における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基であり、特に好ましくは、シクロプロピルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ５における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、アリル基、２－メチルアリル基、または３－ブテニル基であり、特に好ましくは、アリル基、２－メチルアリル基、または３－ブテニル基である。置換基Ａ記載中の置換基を有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, an allyl group, a 2-methylallyl group, or a 3-butenyl group, and particularly preferably an allyl group, a 2-methylallyl group, or a 3-butenyl group. When it has a substituent as described in the substituent A, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with a substituent as described in the substituent A.
　式（１－１）または式（１－２）のＲ５における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、３，３－ジフルオロアリル基である。 The "C2 to C6 haloalkenyl group" in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
　式（１－１）または式（１－２）のＲ５における「置換基Ａで適宜置換されてよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、プロパルギル基、または２－ブチニル基であり、特に好ましくは、プロパルギル基、または２－ブチニル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R5 of formula (1-1) or formula (1-2) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, a propargyl group, or a 2-butynyl group, and particularly preferably a propargyl group or a 2-butynyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（１－１）または式（１－２）のＲ５における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、または４，４，４－トリフルオロ－１－ブチニル基であり、特に好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2 to C6 haloalkynyl group" in R5 of formula (1-1) or formula (1-2) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（１－１）または式（１－２）のＲ５における「Ｒｘ４Ｓ（Ｏ）ｐ－」（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜０～５置換されてもよいフェニル基」に関しては、置換基Ｂを有する場合、フェニル基における水素原子が、独立した置換基Ｂによって１～５置換の間で任意に置換される。Ｒｘ４として、好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、または置換基Ｂで適宜０～５置換されてよいフェニル基であり、さらに好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基であり、特に好ましくは、Ｃ１～Ｃ６のハロアルキル基である。「Ｒｘ４Ｓ（Ｏ）ｐ－」として好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、イソプロピルスルファニル基、イソプロピルスルフィニル基、イソプロピルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルファニル基、シクロプロピルスルフィニル基、シクロプロピルスルホニル基、フェニルスルファニル基、フェニルスルフィニル基、またはフェニルスルホニル基であり、より好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、イソプロピルスルファニル基、イソプロピルスルフィニル基、イソプロピルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルファニル基、シクロプロピルスルフィニル基、またはシクロプロピルスルホニル基であり、さらに好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、イソプロピルスルファニル基、イソプロピルスルフィニル基、イソプロピルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、シクロプロピルスルファニル基、シクロプロピルスルフィニル基、またはシクロプロピルスルホニル基であり、特に好ましくは、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、イソプロピルスルファニル基、イソプロピルスルフィニル基、またはイソプロピルスルホニル基である。 Each term in "Rx4S(O)p-" in R5 of formula (1-1) or formula (1-2) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above. With regard to "a phenyl group which may be optionally substituted with 0 to 5 substituents B", when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B. Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group. Preferred examples of "Rx4S(O)p-" include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, an isopropylsulfanyl group, an isopropylsulfinyl group, an isopropylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1, 2,2,2-pentafluoroethylsulfonyl group, cyclopropylsulfanyl group, cyclopropylsulfinyl group, cyclopropylsulfonyl group, phenylsulfanyl group, phenylsulfinyl group, or phenylsulfonyl group, and more preferably methylsulfanyl group, methylsulfinyl group, methylsulfonyl group, ethylsulfanyl group, ethylsulfinyl group, ethylsulfonyl group, propylsulfanyl group, propylsulfinyl group, propylsulfonyl group, isopropylsulfanyl group, isopropylsulfinyl group, isopropylsulfonyl group, trifluoromethylsulfanyl group, and more preferably, a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a methylsulfonyl group, a methylsulfonyl group, a ethylsulfanyl group, a ethylsulfonyl group, a propylsulfanyl group, a propylsulfanyl group, a propylsulfin ... Sulfonyl group, isopropylsulfanyl group, isopropylsulfinyl group, isopropylsulfonyl group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyclopropylsulfanyl group, cyclopropylsulfinyl group, or cyclopropylsulfonyl group, and particularly preferably ethylsulfanyl group, ethylsulfinyl group, ethylsulfonyl group, propylsulfanyl group, propylsulfinyl group, propylsulfonyl group, isopropylsulfanyl group, isopropylsulfinyl group, or isopropylsulfonyl group.
　Ｈｅｔは、式（Ｈｅｔ）を表し；
Figure JPOXMLDOC01-appb-C000012
　式（Ｈｅｔ）中のＧは、Ｃ－Ｒ６または窒素原子を表す。 Het represents the formula (Het);
Figure JPOXMLDOC01-appb-C000012
G in the formula (Het) represents C-R6 or a nitrogen atom.
　式（Ｈｅｔ）中のＲ６は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表す。 R6 in formula (Het) represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group.
　中でもＲ６は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基が好ましく、
　特にＲ６は、水素原子、ハロゲン原子、または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基が好ましく、
　さらにＲ６は、水素原子が好ましい。 Among these, R6 is preferably a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A;
In particular, R6 is preferably a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent A;
Furthermore, R6 is preferably a hydrogen atom.
　式（Ｈｅｔ）のＲ６には、水素原子、およびシアノ基が含まれる。 R6 in formula (Het) includes a hydrogen atom and a cyano group.
　式（Ｈｅｔ）のＲ６における「ハロゲン原子」は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子であり、さらに好ましくは、フッ素原子、塩素原子、または臭素原子であり、特に好ましくは、塩素原子または臭素原子である。 The "halogen atom" in R6 of formula (Het) is defined as above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a chlorine atom or a bromine atom.
　式（Ｈｅｔ）のＲ６における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、または１，２，２－トリメチルプロピル基であり、より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、またはイソペンチル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、特に好ましくは、メチル基、またはエチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, or a 1,1-dimethylbutyl group. , 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, or 1,2,2-trimethylpropyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, or isopentyl group, even more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and particularly preferably methyl group or ethyl group. When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ６における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、ジブロモメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、または２，２，３，３，３－ペンタフルオロプロピル基であり、さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３，３－トリフルオロプロピル基、または２，２，３，３，３－ペンタフルオロプロピル基であり、特に好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基である。 The "C1-C6 haloalkyl group" in R6 of formula (Het) is the same as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a dibromomethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, or a 2,2,3,3,3-pentafluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, or a 2,2,3,3,3-pentafluoropropyl group, and particularly preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2,2-trifluoroethyl group.
　式（Ｈｅｔ）のＲ６における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａによって置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ６における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、またはアリル基であり、さらに好ましくは、ビニル基、またはアリル基であり、特に好ましくは、アリル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルケニル基における１つの水素原子が、置換基Ａによって置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) is the same as defined above, and is preferably a vinyl group, a 1-propenyl group, or an allyl group, more preferably a vinyl group or an allyl group, and particularly preferably an allyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkenyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ６における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、３，３－ジフルオロアリル基である。 The "C2-C6 haloalkenyl group" in R6 of formula (Het) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group.
　式（Ｈｅｔ）のＲ６における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、またはプロパルギル基であり、特に好ましくは、エチニル基、またはプロパルギル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａによって置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R6 of formula (Het) has the same definition as above, and is preferably an ethynyl group, a 1-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, and particularly preferably an ethynyl group or a propargyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ６における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、２－フルオロエチニル基、２－クロロエチニル基、２－ブロモエチニル基、２－ヨードエチニル基、３，３－ジフルオロ－１－プロピニル基、３－クロロ－３，３－ジフルオロ－１－プロピニル基、３－ブロモ－３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基であり、さらに好ましくは、２－フルオロエチニル基、２－クロロエチニル基、２－ブロモエチニル基、２－ヨードエチニル基、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基であり、特に好ましくは、２－フルオロエチニル基、２－クロロエチニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2-C6 haloalkynyl group" in R6 of formula (Het) is defined as above, and is preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group, more preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group, and particularly preferably a 2-fluoroethynyl group, a 2-chloroethynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（Ｈｅｔ）のＲ７は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表す。 R7 in formula (Het) represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group.
　中でもＲ７は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基が好ましく、
　特にＲ７は、水素原子、ハロゲン原子、または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基が好ましく、
　さらにＲ７は、水素原子が好ましい。 Among these, R7 is preferably a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A;
In particular, R7 is preferably a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent A;
Furthermore, R7 is preferably a hydrogen atom.
　式（Ｈｅｔ）のＲ７は、水素原子、およびシアノ基が含まれる。 R7 in formula (Het) includes a hydrogen atom and a cyano group.
　式（Ｈｅｔ）のＲ７におけるハロゲン原子は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子であり、さらに好ましくは、フッ素原子、塩素原子、または臭素原子であり、特に好ましくは、フッ素原子、または塩素原子である。 The halogen atom in R7 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom or a chlorine atom.
　式（Ｈｅｔ）のＲ７における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、または１，２，２－トリメチルプロピル基であり、より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、またはイソペンチル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、特に好ましくは、メチル基、またはエチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, or a 1,1-dimethylbutyl group. , 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, or 1,2,2-trimethylpropyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, or isopentyl group, even more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and particularly preferably methyl group or ethyl group. When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ７における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３－ジフルオロプロピル基、または３，３，３－トリフルオロプロピル基であり、さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基であり、特に好ましくは、ジフルオロメチル基、またはトリフルオロメチル基である。 The "C1-C6 haloalkyl group" in R7 of formula (Het) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-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 a 2,2,2-trifluoroethyl group, and particularly preferably a difluoromethyl group or a trifluoromethyl group.
　式（Ｈｅｔ）のＲ７における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ７における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、またはアリル基であり、特に好ましくは、ビニル基、またはアリル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルケニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkenyl group in the "C2-C6 alkenyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) is as defined above, and is preferably a vinyl group, a 1-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, and particularly preferably a vinyl group or an allyl group. When it has a substituent A, one hydrogen atom in the C2-C6 alkenyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ７における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、２，２－ジクロロビニル基、３－フルオロアリル基、３，３－ジフルオロアリル基、または３，３－ジクロロアリル基であり、さらに好ましくは、２－フルオロビニル基、または２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、特に好ましくは、２，２－ジフルオロビニル基、または３，３－ジフルオロアリル基である。 The "C2-C6 haloalkenyl group" in R7 of formula (Het) is defined as above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, more preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, and particularly preferably a 2,2-difluorovinyl group or a 3,3-difluoroallyl group.
　式（Ｈｅｔ）のＲ７における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、またはプロパルギル基であり、特に好ましくは、エチニル基である。置換基Ａ記載中の置換基を有する場合、Ｃ２～Ｃ６のアルキニル基における１つの水素原子が、置換基Ａに置換される。 The C2-C6 alkynyl group in the "C2-C6 alkynyl group which may be appropriately substituted with a substituent A" in R7 of formula (Het) has the same definition as above, and is preferably an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, or a propargyl group, and particularly preferably an ethynyl group. When the C2-C6 alkynyl group has a substituent described for the substituent A, one hydrogen atom in the C2-C6 alkynyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ７における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、または４，４，４－トリフルオロ－１－ブチニル基であり、特に好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The "C2-C6 haloalkynyl group" in R7 of formula (Het) is defined as above, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4,4,4-trifluoro-1-butynyl group, or a 4,4,4-trifluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1-butynyl group, and particularly preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.
　式（Ｈｅｔ）中のＲ８は、水素原子、水酸基、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表す。 R8 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1-C6 alkoxy group which may be optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom , a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2. )
　中でもＲ８は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のハロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは、前記と同義である。）が好ましく、
　特にＲ８は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のハロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは、前記と同義である。）が好ましく、
　さらにＲ８は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基が好ましい。 Among these, R8 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
In particular, R8 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
Furthermore, R8 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, or a C1-C6 haloalkyl group.
　式（Ｈｅｔ）のＲ８には、水素原子、水酸基、およびシアノ基が含まれる。 R8 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
　式（Ｈｅｔ）のＲ８におけるハロゲン原子は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子であり、さらに好ましくは、塩素原子、臭素原子、またはヨウ素原子である。 The halogen atom in R8 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a chlorine atom, a bromine atom, or an iodine atom.
　式（Ｈｅｔ）のＲ８における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、または１，２，２－トリメチルプロピル基であり、より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、またはイソペンチル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、特に好ましくは、メチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R8 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethyl butyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, or 1,2,2-trimethylpropyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, or isopentyl group, even more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and particularly preferably methyl group. When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ８における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、２－フルオロプロピル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、３，３，３－トリクロロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、１，１，１，３，３，３－ヘキサフルオロ－２－メチルプロピル基、１，１，１－トリフルオロ－２－メチルプロピル基、２－フルオロイソプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、１，２，２，３，３，４，４，４－オクタフルオロブチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、３，３，４，４，５，５，５－ヘプタフルオロペンチル基、２，３，３，４，４，５，５，５－オクタフルオロペンチル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基、ウンデカフルオロペンチル基、トリデカフルオロヘキシル基であり、
　より好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、２－フルオロプロピル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、３，３，３－トリクロロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、１，１，１，３，３，３－ヘキサフルオロ－２－メチルプロピル基、１，１，１－トリフルオロ－２－メチルプロピル基、２－フルオロイソプロピル基、ヘプタフルオロイソプロピル基であり、
　さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、２－フルオロイソプロピル基、ヘプタフルオロプロピル基であり、
　特に好ましくは、トリフルオロメチル基である。 The "C1-C6 haloalkyl group" in R8 of formula (Het) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 2-fluoropropyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3,3,3-trichloropropyl group, a 2,3 ,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,2,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 1,1,1,3,3,3-hexafluoro-2-methylpropyl group, 1,1,1-trifluoro-2-methylpropyl group, 2-fluoroisopropyl group, heptafluoroisopropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 2, 2,3,3,4,4,4-heptafluorobutyl group, 1,2,2,3,3,4,4,4-octafluorobutyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, 2,3,3,4,4,5,5,5-octafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, undecafluoropentyl group, tridecafluorohexyl group,
More preferably, a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, or a 2,2,2-trichloroethyl group. group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 2-fluoropropyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3,3,3-trichloropropyl group, a 2,3,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 1,1,1,3,3,3-hexafluoro-2-methylpropyl group, a 1,1,1-trifluoro-2-methylpropyl group, a 2-fluoroisopropyl group, and a heptafluoroisopropyl group,
More preferred are a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 2-fluoroisopropyl group, and a heptafluoropropyl group.
Particularly preferred is a trifluoromethyl group.
　式（Ｈｅｔ）のＲ８における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R8 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ８における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、またはイソブトキシ基であり、さらに好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、またはイソプロピルオキシ基であり、特に好ましくは、メトキシ基、またはエトキシ基である。置換基Ａ記載中の置換基を有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａ記載中の置換基によって任意に置換される。 The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be appropriately substituted with a substituent A" in R8 of formula (Het) is the same as defined above, and is 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 or an ethoxy group. When it has a substituent as described for the substituent A, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with a substituent as described for the substituent A.
　式（Ｈｅｔ）のＲ８における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、さらに好ましくは、トリフルオロメトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、特に好ましくは、トリフルオロメトキシ基、または１，１，２，２，２－ペンタフルオロエトキシ基である。 The "C1-C6 haloalkoxy group" in R8 of formula (Het) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a trifluoromethoxy group or a 1,1,2,2,2-pentafluoroethoxy group.
　式（Ｈｅｔ）のＲ８における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基であり、特に好ましくは、シクロプロピルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R8 of formula (Het) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ８における「Ｒｘ４Ｓ（Ｏ）ｐ－」（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜０～５置換されてもよいフェニル基」に関しては、置換基Ｂを有する場合、フェニル基における水素原子が、独立した置換基Ｂによって１～５置換の間で任意に置換される。Ｒｘ４として、好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、または置換基Ｂで適宜０～５置換されてよいフェニル基であり、さらに好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基であり、特に好ましくは、Ｃ１～Ｃ６のハロアルキル基である。「Ｒｘ４Ｓ（Ｏ）ｐ－」として好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルファニル基、シクロプロピルスルフィニル基、シクロプロピルスルホニル基、フェニルスルファニル基、フェニルスルフィニル基、またはフェニルスルホニル基であり、さらに好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、または１，１，２，２，２－ペンタフルオロエチルスルホニル基であり、特に好ましくは、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、またはトリフルオロメチルスルホニル基である。 Each term in "Rx4S(O)p-" in R8 of formula (Het) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above. With regard to "a phenyl group which may be optionally substituted with 0 to 5 substituents B", when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B. Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group. Preferred examples of "Rx4S(O)p-" include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfanyl group, a cyclopropylsulfinyl group, a cyclopropylsulfonyl group, a phenylsulfanyl group, It is preferably a phenylsulfinyl group or a phenylsulfonyl group, more preferably a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, or a 1,1,2,2,2-pentafluoroethylsulfonyl group, and particularly preferably a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group.
　式（Ｈｅｔ）のＲ９は、水素原子、水酸基、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表す。 R9 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1-C6 alkoxy group which may be optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom , a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2. )
　中でもＲ９は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のハロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）が好ましく、
　特にＲ９は、水素原子、ハロゲン原子、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のハロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）が好ましく、
　さらにＲ９は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のハロアルキル基が好ましい。 Among these, R9 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
In particular, R9 is preferably a hydrogen atom, a halogen atom, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
Furthermore, R9 is preferably a hydrogen atom, a halogen atom, or a C1-C6 haloalkyl group.
　式（Ｈｅｔ）のＲ９には、水素原子、水酸基、およびシアノ基が含まれる。 R9 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
　式（Ｈｅｔ）のＲ９におけるハロゲン原子は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子であり、より好ましくは、フッ素原子、塩素原子、または臭素原子であり、さらに好ましくは、フッ素原子、または塩素原子であり、特に好ましくは、塩素原子である。 The halogen atom in R9 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, even more preferably a fluorine atom or a chlorine atom, and particularly preferably a chlorine atom.
　式（Ｈｅｔ）のＲ９における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、ヘキシル基、４－メチルペンチル基、３－メチルペンチル基、２－メチルペンチル基、１－メチルペンチル基、３，３－ジメチルブチル基、２，２－ジメチルブチル基、１，１－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、または１，２，２－トリメチルプロピル基であり、より好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、またはイソペンチル基であり、さらに好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、特に好ましくは、メチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1 to C6 alkyl group in the "C1 to C6 alkyl group which may be appropriately substituted with a substituent A" in R9 of formula (Het) has the same definition as above, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a hexyl group, a 4-methylpentyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 1-methylpentyl group, a 3,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 1,1-dimethyl butyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, or 1,2,2-trimethylpropyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, or isopentyl group, even more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, and particularly preferably methyl group. When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ９における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、２－フルオロプロピル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、３，３，３－トリクロロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、１，１，１，３，３，３－ヘキサフルオロ－２－メチルプロピル基、１，１，１－トリフルオロ－２－メチルプロピル基、２－フルオロイソプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、１，２，２，３，３，４，４，４－オクタフルオロブチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、３，３，４，４，５，５，５－ヘプタフルオロペンチル基、２，３，３，４，４，５，５，５－オクタフルオロペンチル基、２，２，３，３，４，４，５，５，５－ノナフルオロペンチル基、ウンデカフルオロペンチル基、トリデカフルオロヘキシル基であり、
　より好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、２－フルオロプロピル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、３，３，３－トリクロロプロピル基、２，３，３，３－テトラフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，２，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、１，１，１，３，３，３－ヘキサフルオロ－２－メチルプロピル基、１，１，１－トリフルオロ－２－メチルプロピル基、２－フルオロイソプロピル基、ヘプタフルオロイソプロピル基であり、
　さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、モノブロモメチル基、ジブロモメチル基、モノヨードメチル基、ジヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、ジクロロフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、２－クロロ－１，１，２，２－テトラフルオロエチル基、２－フルオロイソプロピル基、ヘプタフルオロプロピル基であり、
　特に好ましくは、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、またはヘプタフルオロプロピル基である。 The "C1-C6 haloalkyl group" in R9 of formula (Het) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 2-fluoropropyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3,3,3-trichloropropyl group, a 2,3 ,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,2,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 1,1,1,3,3,3-hexafluoro-2-methylpropyl group, 1,1,1-trifluoro-2-methylpropyl group, 2-fluoroisopropyl group, heptafluoroisopropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 2, 2,3,3,4,4,4-heptafluorobutyl group, 1,2,2,3,3,4,4,4-octafluorobutyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, 2,3,3,4,4,5,5,5-octafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, undecafluoropentyl group, tridecafluorohexyl group,
More preferably, a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, or a 2,2,2-trichloroethyl group. group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 2-fluoropropyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3,3,3-trichloropropyl group, a 2,3,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,2,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 1,1,1,3,3,3-hexafluoro-2-methylpropyl group, a 1,1,1-trifluoro-2-methylpropyl group, a 2-fluoroisopropyl group, and a heptafluoroisopropyl group,
More preferred are a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, a monoiodomethyl group, a diiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a 2-fluoroisopropyl group, and a heptafluoropropyl group.
Particularly preferred is a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, or a heptafluoropropyl group.
　式（Ｈｅｔ）のＲ９における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R9 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ９における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、またはイソブトキシ基であり、さらに好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、またはイソプロピルオキシ基であり、特に好ましくは、メトキシ基、またはエトキシ基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａに置換される。 The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be appropriately substituted with a substituent A" in R9 of formula (Het) is the same as defined above, and is 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 or an ethoxy group. When it has a substituent A, the hydrogen atom in the C1-C6 alkoxy group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ９における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、さらに好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、特に好ましくは、ジフルオロメトキシ基、またはトリフルオロメトキシ基である。 The "C1-C6 haloalkoxy group" in R9 of formula (Het) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a difluoromethoxy group or a trifluoromethoxy group.
　式（Ｈｅｔ）のＲ９における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基であり、特に好ましくは、シクロプロピルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R9 of formula (Het) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ９における「Ｒｘ４Ｓ（Ｏ）ｐ－」（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜０～５置換されてもよいフェニル基」に関しては、置換基Ｂを有する場合、フェニル基における水素原子が、独立した置換基Ｂによって１～５置換の間で任意に置換される。Ｒｘ４として、好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、または置換基Ｂで適宜０～５置換されてよいフェニル基であり、さらに好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基であり、特に好ましくは、Ｃ１～Ｃ６のハロアルキル基である。「Ｒｘ４Ｓ（Ｏ）ｐ－」として好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルファニル基、シクロプロピルスルフィニル基、シクロプロピルスルホニル基、フェニルスルファニル基、フェニルスルフィニル基、またはフェニルスルホニル基であり、さらに好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、または１，１，２，２，２－ペンタフルオロエチルスルホニル基であり、特に好ましくは、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、またはトリフルオロメチルスルホニル基である。 Each term in "Rx4S(O)p-" in R9 of formula (Het) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above. With regard to "a phenyl group which may be optionally substituted with 0 to 5 substituents B", when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B. Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group. Preferred examples of "Rx4S(O)p-" include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfanyl group, a cyclopropylsulfinyl group, a cyclopropylsulfonyl group, a phenylsulfanyl group, It is preferably a phenylsulfinyl group or a phenylsulfonyl group, more preferably a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, or a 1,1,2,2,2-pentafluoroethylsulfonyl group, and particularly preferably a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group.
　式（Ｈｅｔ）のＲ１０は、水素原子、水酸基、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表す。 R10 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1-C6 alkoxy group which may be optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom , a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2. )
　中でもＲ１０は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）が好ましく、
　特にＲ１０は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のハロアルキル基が好ましく、
　さらにＲ１０は、水素原子が好ましい。 Among these, R10 is preferably a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or Rx4S(O)p- (wherein Rx4 and p are as defined above),
In particular, R10 is preferably a hydrogen atom, a halogen atom, or a C1-C6 haloalkyl group.
Furthermore, R10 is preferably a hydrogen atom.
　式（Ｈｅｔ）のＲ１０には、水素原子、水酸基、およびシアノ基が含まれる。 R10 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
　式（Ｈｅｔ）のＲ１０におけるハロゲン原子は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子であり、さらに好ましくは、フッ素原子、塩素原子、または臭素原子であり、特に好ましくは、フッ素原子、または塩素原子である。 The halogen atom in R10 of formula (Het) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, more preferably a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a fluorine atom or a chlorine atom.
　式（Ｈｅｔ）のＲ１０における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、さらに好ましくは、メチル基、エチル基、またはイソプロピル基であり、特に好ましくは、メチル基、またはエチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における１つの水素原子が、置換基Ａに置換される。 The C1-C6 alkyl group in the "C1-C6 alkyl group which may be appropriately substituted with a substituent A" in R10 of formula (Het) has the same definition as above, and is 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, or an isopropyl group, and particularly preferably a methyl group or an ethyl group. When it has a substituent A, one hydrogen atom in the C1-C6 alkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ１０における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，２，２，２－テトラフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、または１，１，２，２，３，３，３－ヘプタフルオロプロピル基であり、さらに好ましくは、ジフルオロメチル基、トリフルオロメチル基、１，２，２，２－テトラフルオロエチル基、１，１，２，２，２－ペンタフルオロエチル基、または１，１，２，２，３，３，３－ヘプタフルオロプロピル基であり、特に好ましくは、ジフルオロメチル基、トリフルオロメチル基、１，１，２，２，２－ペンタフルオロエチル基、または１，１，２，２，３，３，３－ヘプタフルオロプロピル基である。 The "C1-C6 haloalkyl group" in R10 of formula (Het) is the same as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group, and particularly preferably a difluoromethyl group, a trifluoromethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2,2,3,3,3-heptafluoropropyl group.
　式（Ｈｅｔ）のＲ１０における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基であり、特に好ましくは、シクロプロピル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkyl group in the "C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A" in R10 of formula (Het) is as defined above, and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkyl group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ１０における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、またはイソブトキシ基であり、さらに好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、またはイソプロピルオキシ基であり、特に好ましくは、メトキシ基、またはエトキシ基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａに置換される。 The C1-C6 alkoxy group in the "C1-C6 alkoxy group which may be appropriately substituted with a substituent A" in R10 of formula (Het) is as defined above, and is 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 or an ethoxy group. When it has a substituent A, the hydrogen atom in the C1-C6 alkoxy group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ１０における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、さらに好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、１，２，２，２－テトラフルオロエトキシ基、１，１，２，２，２－ペンタフルオロエトキシ基、またはヘプタフルオロプロピルオキシ基であり、特に好ましくは、ジフルオロメトキシ基、またはトリフルオロメトキシ基である。 The "C1-C6 haloalkoxy group" in R10 of formula (Het) is defined as above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a heptafluoropropyloxy group, and particularly preferably a difluoromethoxy group or a trifluoromethoxy group.
　式（Ｈｅｔ）のＲ１０における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基であり、特に好ましくは、シクロプロピルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における１つの水素原子が、置換基Ａに置換される。 The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A" in R10 of formula (Het) is as defined above, and is preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group. When it has a substituent A, one hydrogen atom in the C3-C8 cycloalkoxy group is substituted with the substituent A.
　式（Ｈｅｔ）のＲ１０における「Ｒｘ４Ｓ（Ｏ）ｐ－」（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜０～５置換されてもよいフェニル基」に関しては、置換基Ｂを有する場合、フェニル基における水素原子が、独立した置換基Ｂによって１～５置換の間で任意に置換される。Ｒｘ４として、好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、または置換基Ｂで適宜０～５置換されてよいフェニル基であり、さらに好ましくは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基であり、特に好ましくは、Ｃ１～Ｃ６のハロアルキル基である。「Ｒｘ４Ｓ（Ｏ）ｐ－」として好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、１，１，２，２，２－ペンタフルオロエチルスルホニル基、シクロプロピルスルファニル基、シクロプロピルスルフィニル基、シクロプロピルスルホニル基、フェニルスルファニル基、フェニルスルフィニル基、またはフェニルスルホニル基であり、さらに好ましくは、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基、１，１，２，２，２－ペンタフルオロエチルスルファニル基、１，１，２，２，２－ペンタフルオロエチルスルフィニル基、または１，１，２，２，２－ペンタフルオロエチルスルホニル基であり、特に好ましくは、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、またはトリフルオロメチルスルホニル基である。 Each term in "Rx4S(O)p-" in R10 of formula (Het) (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2) is as defined above. With regard to "a phenyl group which may be optionally substituted with 0 to 5 substituents B", when the phenyl group has a substituent B, the hydrogen atoms in the phenyl group are arbitrarily substituted with between 1 and 5 independent substituents B. Rx4 is preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, or a phenyl group which may be appropriately substituted with 0 to 5 substituents B, more preferably a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, and particularly preferably a C1-C6 haloalkyl group. Preferred examples of "Rx4S(O)p-" include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfanyl group, a cyclopropylsulfinyl group, a cyclopropylsulfonyl group, a phenylsulfanyl group, It is preferably a phenylsulfinyl group or a phenylsulfonyl group, more preferably a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfanyl group, a 1,1,2,2,2-pentafluoroethylsulfinyl group, or a 1,1,2,2,2-pentafluoroethylsulfonyl group, and particularly preferably a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group.
　「置換基Ａ」は、水酸基、シアノ基、ニトロ基、ハロゲン原子、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜０～５置換されてよいフェニル基、置換基Ｃで適宜０～４置換されてよい５～６員芳香族複素環基、および１～２個の酸素原子を含む３～６員環の基からなる群から選択される。 "Substituent A" is selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group optionally substituted with 0-5 substituents C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents C, and a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.
　中でも「置換基Ａ」は、シアノ基、ハロゲン原子、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜０～５置換されてよいフェニル基、置換基Ｃで適宜０～４置換されてよい５～６員芳香族複素環基、および１～２個の酸素原子を含む３～６員環の基からなる群から選択される。 Among them, "substituent A" is selected from the group consisting of a cyano group, a halogen atom, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a phenyl group optionally substituted with 0-5 substituents C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents C, and a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.
　特に「置換基Ａ」は、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、置換基Ｃで適宜０～５置換されてよいフェニル基、置換基Ｃで適宜０～４置換されてよい５～６員芳香族複素環基、および１～２個の酸素原子を含む３～６員環の基からなる群から選択される。 In particular, "substituent A" is selected from the group consisting of a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a phenyl group optionally substituted with 0-5 substituents C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents C, and a 3- to 6-membered ring group containing 1 or 2 oxygen atoms.
　「置換基Ａ」の好ましい具体例に関しては、水酸基；シアノ基；ニトロ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ３～Ｃ８シクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
　Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、２，２，３，３－テトラフルオロプロピルオキシ基、および２，２，３，３，３－ペンタフルオロプロピルオキシ基；
　Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基；
　置換基Ｃで適宜０～５置換されてよいフェニル基として、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、ジクロロフェニル基、ブロモフェニル基、ヨードフェニル基、トルイル基、エチルフェニル基、イソプロピルフェニル基、ジフルオロメチルフェニル基、トリフルオロメチルフェニル基、ペンタフルオロエチルフェニル基、シクロプロピルフェニル基、シクロブチルフェニル基、シクロペンチルフェニル基、メトキシフェニル基、エトキシフェニル基、イソプロピルオキシフェニル基、トリフルオロメトキシフェニル基、２，２－ジフルオロエトキシフェニル基、２，２，２－トリフルオロエトキシフェニル基、２，２，３，３，３－ペンタフルオロプロピルオキシフェニル基、メチルスルファニルフェニル基、メチルスルフィニルフェニル基、メチルスルホニルフェニル基、エチルスルファニルフェニル基、エチルスルフィニルフェニル基、エチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、トリフルオロメチルスルフィニルフェニル基、およびトリフルオロメチルスルホニルフェニル基；
　置換基Ｃで適宜０～４置換されてよい５～６員芳香族複素環基として、ピリジル基、ピリジン－Ｎ－オキシド基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－ヨードピリジル基、３－ヨードピリジル基、４－ヨードピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－シクロプロピルピリジル基、３－シクロプロピルピリジル基、４－シクロプロピルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリダジニル基、３－フルオロピリダジニル基、４－フルオロピリダジニル基、３－クロロピリダジニル基、４－クロロピリダジニル基、３－ブロモピリダジニル基、４－ブロモピリダジニル基、３－メチルピリダジニル基、４－メチルピリダジニル基、ピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－ブロモピリミジニル基、４－ブロモピリミジニル基、５－ブロモピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、５－メトキシピリミジニル基、ピラジニル基、２－フルオロピラジニル基、２－クロロピラジニル基、２－ブロモピラジニル基、２－メチルピラジニル基、２－トリフルオロメチルピラジニル基、２－メトキシピラジニル基、１，２，４－オキサジアゾリル基、（５－トリフルオロメチル）－１，２，４－オキサジアゾリル基、およびチアゾリル基；
　ならびに１～２個の酸素原子を含む３～６員環の基として、オキシラン－２－イル基、オキセタン－３－イル基、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、１，４－ジオキサン－２－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、４－ジヒドロフラン－２（３Ｈ）－オン基、３－テトラヒドロ－２Ｈ－ピラン－２－オン基、４－テトラヒドロ－２Ｈ－ピラン－２－オン基、および２－オキソテトラヒドロフラン－３－イル基が挙げられる。 Preferable specific examples of "substituent A" include a hydroxyl group, a cyano group, a nitro group,
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropyloxy group, and a 2,2,3,3,3-pentafluoropropyloxy group;
C3 to C8 cycloalkoxy groups include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
Examples of the phenyl group which may be optionally substituted with 0 to 5 substituents C include a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a dichlorophenyl group, a bromophenyl group, an iodophenyl group, a toluyl group, an ethylphenyl group, an isopropylphenyl group, a difluoromethylphenyl group, a trifluoromethylphenyl group, a pentafluoroethylphenyl group, a cyclopropylphenyl group, a cyclobutylphenyl group, a cyclopentylphenyl group, a methoxyphenyl group, an ethoxyphenyl group, an isopropyloxyphenyl group, a trifluoromethoxyphenyl group, a 2,2-difluoroethoxyphenyl group, a 2,2,2-trifluoroethoxyphenyl group, a 2,2,3,3,3-pentafluoropropyloxyphenyl group, a methylsulfanylphenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, an ethylsulfanylphenyl group, an ethylsulfanylphenyl group, an ethylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, and a trifluoromethylsulfonylphenyl group;
Examples of 5- to 6-membered aromatic heterocyclic groups which may be optionally substituted with 0 to 4 substituents C include a pyridyl group, a pyridine-N-oxide group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-iodopyridyl group, a 3-iodopyridyl group, a 4-iodopyridyl group, a 2-methylpyridyl group, a 3-methylpyridyl group, and a 4-methylpyridyl group. , 2-trifluoromethylpyridyl group, 3-trifluoromethylpyridyl group, 4-trifluoromethylpyridyl group, 2-cyclopropylpyridyl group, 3-cyclopropylpyridyl group, 4-cyclopropylpyridyl group, 2-methoxypyridyl group, 3-methoxypyridyl group, 4-methoxypyridyl group, pyridazinyl group, 3-fluoropyridazinyl group, 4-fluoropyridazinyl group, 3-chloropyridazinyl group, 4-chloropyridazinyl group, 3-bromopyridazinyl group, 4-bromopyridazinyl group group, 3-methylpyridazinyl group, 4-methylpyridazinyl group, pyrimidinyl group, 2-fluoropyrimidinyl group, 4-fluoropyrimidinyl group, 5-fluoropyrimidinyl group, 2-chloropyrimidinyl group, 4-chloropyrimidinyl group, 5-chloropyrimidinyl group, 2-bromopyrimidinyl group, 4-bromopyrimidinyl group, 5-bromopyrimidinyl group, 2-methylpyrimidinyl group, 4-methylpyrimidinyl group, 5-methylpyrimidinyl group, 2-trifluoromethylpyrimidinyl group, 4-trifluoromethylpyrimidinyl group, fluoromethylpyrimidinyl group, 5-trifluoromethylpyrimidinyl group, 2-methoxypyrimidinyl group, 4-methoxypyrimidinyl group, 5-methoxypyrimidinyl group, pyrazinyl group, 2-fluoropyrazinyl group, 2-chloropyrazinyl group, 2-bromopyrazinyl group, 2-methylpyrazinyl group, 2-trifluoromethylpyrazinyl group, 2-methoxypyrazinyl group, 1,2,4-oxadiazolyl group, (5-trifluoromethyl)-1,2,4-oxadiazolyl group, and thiazolyl group;
and 3- to 6-membered ring groups containing 1 to 2 oxygen atoms include oxiran-2-yl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-2-yl, tetrahydro-2H-pyran-3-yl, tetrahydro-2H-pyran-4-yl, 1,4-dioxan-2-yl, 3-dihydrofuran-2(3H)-one, 4-dihydrofuran-2(3H)-one, 3-tetrahydro-2H-pyran-2-one, 4-tetrahydro-2H-pyran-2-one, and 2-oxotetrahydrofuran-3-yl.
　「置換基Ａ」のさらに好ましい具体例に関しては、シアノ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子；
　Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
　Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、２，２，３，３－テトラフルオロプロピルオキシ基、および２，２，３，３，３－ペンタフルオロプロピルオキシ基；
　置換基Ｃで適宜０～５置換されてよいフェニル基として、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、ジクロロフェニル基、ブロモフェニル基、ヨードフェニル基、トルイル基、エチルフェニル基、イソプロピルフェニル基、ジフルオロメチルフェニル基、トリフルオロメチルフェニル基、シクロプロピルフェニル基、メトキシフェニル基、エトキシフェニル基、イソプロピルオキシフェニル基、トリフルオロメトキシフェニル基、２，２－ジフルオロエトキシフェニル基、２，２，２－トリフルオロエトキシフェニル基、２，２，３，３，３－ペンタフルオロプロピルオキシフェニル基、メチルスルファニルフェニル基、メチルスルフィニルフェニル基、メチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、トリフルオロメチルスルフィニルフェニル基、およびトリフルオロメチルスルホニルフェニル基；
　置換基Ｃで適宜０～４置換されてよい５～６員芳香族複素環基として、ピリジル基、ピリジン－Ｎ－オキシド基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－ヨードピリジル基、３－ヨードピリジル基、４－ヨードピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－シクロプロピルピリジル基、３－シクロプロピルピリジル基、４－シクロプロピルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリダジニル基、３－フルオロピリダジニル基、４－フルオロピリダジニル基、３－クロロピリダジニル基、４－クロロピリダジニル基、３－ブロモピリダジニル基、４－ブロモピリダジニル基、３－メチルピリダジニル基、４－メチルピリダジニル基、ピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－ブロモピリミジニル基、４－ブロモピリミジニル基、５－ブロモピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、５－メトキシピリミジニル基、ピラジニル基、２－フルオロピラジニル基、２－クロロピラジニル基、２－ブロモピラジニル基、２－メチルピラジニル基、２－トリフルオロメチルピラジニル基、２－メトキシピラジニル基、１，２，４－オキサジアゾリル基、（５－トリフルオロメチル）－１，２，４－オキサジアゾリル基、およびチアゾリル基；
　ならびに１～２個の酸素原子を含む３～６員環の基として、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、４－ジヒドロフラン－２（３Ｈ）－オン基、３－テトラヒドロ－２Ｈ－ピラン－２－オン基、４－テトラヒドロ－２Ｈ－ピラン－２－オン基、および２－オキソテトラヒドロフラン－３－イル基が挙げられる。 More preferred examples of "substituent A" include a cyano group;
Halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms;
C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropyloxy group, and a 2,2,3,3,3-pentafluoropropyloxy group;
Examples of the phenyl group which may be optionally substituted with 0 to 5 substituents C include a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a dichlorophenyl group, a bromophenyl group, an iodophenyl group, a toluyl group, an ethylphenyl group, an isopropylphenyl group, a difluoromethylphenyl group, a trifluoromethylphenyl group, a cyclopropylphenyl group, a methoxyphenyl group, an ethoxyphenyl group, an isopropyloxyphenyl group, a trifluoromethoxyphenyl group, a 2,2-difluoroethoxyphenyl group, a 2,2,2-trifluoroethoxyphenyl group, a 2,2,3,3,3-pentafluoropropyloxyphenyl group, a methylsulfanylphenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, and a trifluoromethylsulfonylphenyl group;
Examples of 5- to 6-membered aromatic heterocyclic groups which may be optionally substituted with 0 to 4 substituents C include a pyridyl group, a pyridine-N-oxide group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-iodopyridyl group, a 3-iodopyridyl group, a 4-iodopyridyl group, a 2-methylpyridyl group, a 3-methylpyridyl group, and a 4-methylpyridyl group. , 2-trifluoromethylpyridyl group, 3-trifluoromethylpyridyl group, 4-trifluoromethylpyridyl group, 2-cyclopropylpyridyl group, 3-cyclopropylpyridyl group, 4-cyclopropylpyridyl group, 2-methoxypyridyl group, 3-methoxypyridyl group, 4-methoxypyridyl group, pyridazinyl group, 3-fluoropyridazinyl group, 4-fluoropyridazinyl group, 3-chloropyridazinyl group, 4-chloropyridazinyl group, 3-bromopyridazinyl group, 4-bromopyridazinyl group group, 3-methylpyridazinyl group, 4-methylpyridazinyl group, pyrimidinyl group, 2-fluoropyrimidinyl group, 4-fluoropyrimidinyl group, 5-fluoropyrimidinyl group, 2-chloropyrimidinyl group, 4-chloropyrimidinyl group, 5-chloropyrimidinyl group, 2-bromopyrimidinyl group, 4-bromopyrimidinyl group, 5-bromopyrimidinyl group, 2-methylpyrimidinyl group, 4-methylpyrimidinyl group, 5-methylpyrimidinyl group, 2-trifluoromethylpyrimidinyl group, 4-trifluoromethylpyrimidinyl group, fluoromethylpyrimidinyl group, 5-trifluoromethylpyrimidinyl group, 2-methoxypyrimidinyl group, 4-methoxypyrimidinyl group, 5-methoxypyrimidinyl group, pyrazinyl group, 2-fluoropyrazinyl group, 2-chloropyrazinyl group, 2-bromopyrazinyl group, 2-methylpyrazinyl group, 2-trifluoromethylpyrazinyl group, 2-methoxypyrazinyl group, 1,2,4-oxadiazolyl group, (5-trifluoromethyl)-1,2,4-oxadiazolyl group, and thiazolyl group;
and 3- to 6-membered ring groups containing 1 to 2 oxygen atoms include tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydro-2H-pyran-2-yl, tetrahydro-2H-pyran-3-yl, tetrahydro-2H-pyran-4-yl, 3-dihydrofuran-2(3H)-one, 4-dihydrofuran-2(3H)-one, 3-tetrahydro-2H-pyran-2-one, 4-tetrahydro-2H-pyran-2-one, and 2-oxotetrahydrofuran-3-yl.
　「置換基Ａ」の特に好ましい具体例に関しては、シアノ基；
　Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、およびエトキシ基；
　置換基Ｃで適宜０～５置換されてよいフェニル基として、フェニル基、シアノフェニル基、フルオロフェニル基、クロロフェニル基、ジクロロフェニル基、トルイル基、トリフルオロメチルフェニル基、シクロプロピルフェニル基、メトキシフェニル基、トリフルオロメトキシフェニル基、メチルスルホニルフェニル基、トリフルオロメチルスルファニルフェニル基、およびトリフルオロメチルスルホニルフェニル基；
　置換基Ｃで適宜０～４置換されてよい５～６員芳香族複素環基として、ピリジル基、ピリジン－Ｎ－オキシド基、２－フルオロピリジル基、３－フルオロピリジル基、４－フルオロピリジル基、２－クロロピリジル基、３－クロロピリジル基、４－クロロピリジル基、２－ブロモピリジル基、３－ブロモピリジル基、４－ブロモピリジル基、２－メチルピリジル基、３－メチルピリジル基、４－メチルピリジル基、２－トリフルオロメチルピリジル基、３－トリフルオロメチルピリジル基、４－トリフルオロメチルピリジル基、２－シクロプロピルピリジル基、２－メトキシピリジル基、３－メトキシピリジル基、４－メトキシピリジル基、ピリダジニル基、３－フルオロピリダジニル基、４－フルオロピリダジニル基、３－クロロピリダジニル基、４－クロロピリダジニル基、３－メチルピリダジニル基、４－メチルピリダジニル基、ピリミジニル基、２－フルオロピリミジニル基、４－フルオロピリミジニル基、５－フルオロピリミジニル基、２－クロロピリミジニル基、４－クロロピリミジニル基、５－クロロピリミジニル基、２－メチルピリミジニル基、４－メチルピリミジニル基、５－メチルピリミジニル基、２－トリフルオロメチルピリミジニル基、４－トリフルオロメチルピリミジニル基、５－トリフルオロメチルピリミジニル基、２－メトキシピリミジニル基、４－メトキシピリミジニル基、５－メトキシピリミジニル基、ピラジニル基、２－フルオロピラジニル基、２－クロロピラジニル基、２－メチルピラジニル基、２－トリフルオロメチルピラジニル基、２－メトキシピラジニル基、１，２，４－オキサジアゾリル基、（５－トリフルオロメチル）－１，２，４－オキサジアゾリル基、およびチアゾリル基；
　ならびに１～２個の酸素原子を含む３～６員環の基として、テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－２－イル基、テトラヒドロ－２Ｈ－ピラン－３－イル基、テトラヒドロ－２Ｈ－ピラン－４－イル基、３－ジヒドロフラン－２（３Ｈ）－オン基、および２－オキソテトラヒドロフラン－３－イル基が挙げられる。 Particularly preferred examples of "substituent A" include a cyano group;
As a C3 to C8 cycloalkyl group, a cyclopropyl group;
C1 to C6 alkoxy groups include methoxy and ethoxy groups;
Examples of phenyl groups which may be optionally substituted with 0 to 5 substituents C include a phenyl group, a cyanophenyl group, a fluorophenyl group, a chlorophenyl group, a dichlorophenyl group, a toluyl group, a trifluoromethylphenyl group, a cyclopropylphenyl group, a methoxyphenyl group, a trifluoromethoxyphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, and a trifluoromethylsulfonylphenyl group;
Examples of the 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents C include a pyridyl group, a pyridine-N-oxide group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, a 4-fluoropyridyl group, a 2-chloropyridyl group, a 3-chloropyridyl group, a 4-chloropyridyl group, a 2-bromopyridyl group, a 3-bromopyridyl group, a 4-bromopyridyl group, a 2-methylpyridyl group, a 3-methylpyridyl group, a 4-methylpyridyl group, a 2-trifluoromethylpyridyl group, a 3-trifluoromethylpyridyl group, a 4-trifluoromethylpyridyl group, a 2-cyclopropylpyridyl group, a 2-methoxypyridyl group, a 3-methoxypyridyl group, a 4-methoxypyridyl group, a pyridazinyl group, a 3-fluoropyridazinyl group, a 4-fluoropyridazinyl group, a 3-chloropyridazinyl group, a 4-chloropyridazinyl group, a 3-methylpyridazinyl group, a 4-methylpyridyl group, pyridazinyl group, pyrimidinyl group, 2-fluoropyrimidinyl group, 4-fluoropyrimidinyl group, 5-fluoropyrimidinyl group, 2-chloropyrimidinyl group, 4-chloropyrimidinyl group, 5-chloropyrimidinyl group, 2-methylpyrimidinyl group, 4-methylpyrimidinyl group, 5-methylpyrimidinyl group, 2-trifluoromethylpyrimidinyl group, 4-trifluoromethylpyrimidinyl group, 5-trifluoromethylpyrimidinyl group, 2-methoxypyrimidinyl group, 4-methoxypyrimidinyl group, 5-methoxypyrimidinyl group, pyrazinyl group, 2-fluoropyrazinyl group, 2-chloropyrazinyl group, 2-methylpyrazinyl group, 2-trifluoromethylpyrazinyl group, 2-methoxypyrazinyl group, 1,2,4-oxadiazolyl group, (5-trifluoromethyl)-1,2,4-oxadiazolyl group, and thiazolyl group;
and 3- to 6-membered ring groups containing 1 to 2 oxygen atoms include a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a tetrahydro-2H-pyran-2-yl group, a tetrahydro-2H-pyran-3-yl group, a tetrahydro-2H-pyran-4-yl group, a 3-dihydrofuran-2(3H)-one group, and a 2-oxotetrahydrofuran-3-yl group.
　「置換基Ｂ」は、水酸基、シアノ基、ニトロ基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５は、水酸基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、Ｃ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、ｐは、０、１、または２の整数を表す。）からなる群から選択される。 "Substituent B" is selected from the group consisting of hydroxyl, cyano, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, and Rx5S(O)p- (wherein Rx5 represents hydroxyl, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, or C2-C6 haloalkynyl, and p represents an integer of 0, 1, or 2).
　中でも「置換基Ｂ」は、水酸基、シアノ基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５およびｐは、前記と同義である。）からなる群から選択される。 Among them, "substituent B" is selected from the group consisting of a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, and Rx5S(O)p- (wherein Rx5 and p are as defined above).
　特に「置換基Ｂ」は、シアノ基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５およびｐは、前記と同義である。）からなる群から選択される。 In particular, "substituent B" is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and Rx5S(O)p- (wherein Rx5 and p are as defined above).
　「置換基Ｂ」の好ましい具体例に関しては、水酸基；シアノ基；ニトロ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ１～Ｃ６のアルキル基として、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、およびヘキシル基；　Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、ジブロモメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，３，３，３－ペンタフルオロプロピル基、およびヘプタフルオロプロピル基；
　Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
　Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、２，２，３，３－テトラフルオロプロピルオキシ基、および２，２，３，３，３－ペンタフルオロプロピルオキシ基；
　Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基；
　ならびにＲｘ５Ｓ（Ｏ）ｐ－として、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基が挙げられる。 Preferable specific examples of "substituent B" include a hydroxyl group; a cyano group; a nitro group;
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C1-C6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, and hexyl; C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, dibromomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,2,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2,3,3,3-pentafluoropropyl, and heptafluoropropyl;
C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropyloxy group, and a 2,2,3,3,3-pentafluoropropyloxy group;
C3 to C8 cycloalkoxy groups include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
and Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and a trifluoromethylsulfonyl group.
　「置換基Ｂ」のさらに好ましい具体例に関しては、水酸基；シアノ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ１～Ｃ６のアルキル基として、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、およびｔ－ブチル基；
　Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、およびヘプタフルオロプロピル基；
　Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
　Ｃ１～Ｃ６のハロアルコキシ基として、トリフルオロメトキシ基、および２，２，２－トリフルオロエトキシ基；
　Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、およびシクロペンチルオキシ基；
　ならびにＲｘ５Ｓ（Ｏ）ｐ－として、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基が挙げられる。 More preferred examples of "substituent B" include a hydroxyl group; a cyano group;
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C1 to C6 alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group;
C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, and a heptafluoropropyl group;
As a C3 to C8 cycloalkyl group, a cyclopropyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1-C6 haloalkoxy groups include a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group;
C3 to C8 cycloalkoxy groups include a cyclopropyloxy group and a cyclopentyloxy group;
and Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and a trifluoromethylsulfonyl group.
　「置換基Ｂ」の特に好ましい具体例に関しては、シアノ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ１～Ｃ６のアルキル基として、メチル基、エチル基、プロピル基、およびイソプロピル基；
　Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、およびヘプタフルオロプロピル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、およびプロピルオキシ基；
　ならびにＲｘ５Ｓ（Ｏ）ｐ－として、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基が挙げられる。 Particularly preferred examples of "substituent B" include a cyano group;
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C1-C6 alkyl groups include a methyl group, an ethyl group, a propyl group, and an isopropyl group;
C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, and a propyloxy group;
and Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and a trifluoromethylsulfonyl group.
　「置換基Ｃ」は、シアノ基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５およびｐは前記と同義である。）からなる群から選択される。 "Substituent C" is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, and Rx5S(O)p- (wherein Rx5 and p are as defined above).
　中でも「置換基Ｃ」は、シアノ基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、およびＣ１～Ｃ６のハロアルコキシ基からなる群から選択される。 Among them, "substituent C" is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group.
　特に「置換基Ｃ」は、シアノ基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、およびＣ１～Ｃ６のアルコキシ基からなる群から選択される。 In particular, "substituent C" is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, and a C1-C6 alkoxy group.
　「置換基Ｃ」の好ましい具体例に関しては、シアノ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ１～Ｃ６のアルキル基として、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、およびヘキシル基；　Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、ジクロロメチル基、トリクロロメチル基、ジブロモメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、１，２，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，３，３，３－ペンタフルオロプロピル基、およびヘプタフルオロプロピル基；
　Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
　Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、２，２，３，３－テトラフルオロプロピルオキシ基、および２，２，３，３，３－ペンタフルオロプロピルオキシ基；
　Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基；
　ならびにＲｘ５Ｓ（Ｏ）ｐ－として、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、プロピルスルファニル基、プロピルスルフィニル基、プロピルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基が挙げられる。 Preferred specific examples of "substituent C" include a cyano group;
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C1-C6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, and hexyl; C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, dibromomethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,2,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2,3,3,3-pentafluoropropyl, and heptafluoropropyl;
C3 to C8 cycloalkyl groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropyloxy group, and a 2,2,3,3,3-pentafluoropropyloxy group;
C3 to C8 cycloalkoxy groups include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
and Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and a trifluoromethylsulfonyl group.
　「置換基Ｃ」のさらに好ましい具体例に関しては、シアノ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ１～Ｃ６のアルキル基として、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、およびｔ－ブチル基；
　Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、およびヘプタフルオロプロピル基；
　Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
　Ｃ１～Ｃ６のハロアルコキシ基として、トリフルオロメトキシ基、および２，２，２－トリフルオロエトキシ基；
　Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、およびシクロペンチルオキシ基；
　ならびにＲｘ５Ｓ（Ｏ）ｐ－として、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、エチルスルファニル基、エチルスルフィニル基、エチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基が挙げられる。 More preferred examples of "substituent C" include a cyano group;
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C1 to C6 alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group;
C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, and a heptafluoropropyl group;
As a C3 to C8 cycloalkyl group, a cyclopropyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1-C6 haloalkoxy groups include a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group;
C3 to C8 cycloalkoxy groups include a cyclopropyloxy group and a cyclopentyloxy group;
and Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and a trifluoromethylsulfonyl group.
　「置換基Ｃ」の特に好ましい具体例に関しては、シアノ基；
　ハロゲン原子として、フッ素原子、塩素原子、臭素原子、およびヨウ素原子；
　Ｃ１～Ｃ６のアルキル基として、メチル基、エチル基、プロピル基、およびイソプロピル基；
　Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、およびヘプタフルオロプロピル基；
　Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、およびプロピルオキシ基；
　ならびにＲｘ５Ｓ（Ｏ）ｐ－として、メチルスルファニル基、メチルスルフィニル基、メチルスルホニル基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、トリフルオロメチルスルホニル基が挙げられる。 Particularly preferred examples of "substituent C" include a cyano group;
Halogen atoms include fluorine, chlorine, bromine, and iodine atoms;
C1-C6 alkyl groups include a methyl group, an ethyl group, a propyl group, and an isopropyl group;
C1-C6 haloalkyl groups include a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group;
C1 to C6 alkoxy groups include a methoxy group, an ethoxy group, and a propyloxy group;
and Rx5S(O)p- includes a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, and a trifluoromethylsulfonyl group.
　式（１－１）、式（１－２）、式（１－３）、および式（１－４）で表される化合物は、１個以上の不斉原子を含むことがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 The compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain one or more asymmetric atoms. In this case, the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
　式（１－１）、式（１－２）、式（１－３）、および式（１－４）で表される化合物は、１個または２個の軸不斉を有することがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 The compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may have one or two axial chiralities. In this case, the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
　式（１－１）、式（１－２）、式（１－３）、および式（１－４）で表される化合物は、幾何異性体を含むことがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 The compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain geometric isomers. In this case, the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
　式（１－１）、式（１－２）、式（１－３）、および式（１－４）で表される化合物は、回転異性体を含むことがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 The compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain rotational isomers. In this case, the isomer ratio may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.
　式（１－１）、式（１－２）、式（１－３）、および式（１－４）で表される化合物は、塩を形成できることがある。塩酸、硫酸、酢酸、フマル酸、マレイン酸のような酸塩や、ナトリウム、カリウム、カルシウムのような金属塩等が例示されるが、これに限定しない。農園芸用有害節足動物防除剤として使用できる塩が好ましい。 The compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may be capable of forming salts. Examples include, but are not limited to, acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium. Salts that can be used as agricultural and horticultural pest control agents are preferred.
　以上説明したＲ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｈｅｔ、Ｇ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、置換基Ａ、置換基Ｂ、置換基Ｃ、Ｒｘ１、Ｒｘ２、Ｒｘ３、Ｒｘ４、Ｒｘ５、およびｐにおける好ましい範囲を任意に組み合わせて得られる全ての化合物の範囲も本発明の　式（１－１）、式（１－２）、その製造中間体化合物の式（１－３）、または式（１－４）の範囲として記載されているものとする。 The ranges of all compounds obtained by any combination of the preferred ranges for R1, R2, R3, R4, R5, Het, G, R6, R7, R8, R9, R10, substituent A, substituent B, substituent C, Rx1, Rx2, Rx3, Rx4, Rx5, and p described above are also described as the ranges of formula (1-1), formula (1-2), and their intermediate compounds (1-3) or (1-4) of the present invention.
　本発明の具体的な化合物は、表１に示す構造式Ｃ－１～Ｃ－１６８（ここで、波線で切断される結合位置は、表２中のＨｅｔが結合する位置を表す。）と、表２に示す構造式Ｐｙｒａ－１～Ｐｙｒａ－４８（ここで、表２中のＲ１、Ｒ２、Ｒ３、Ｒ４、Ｈｅｔ、およびｐは、前記と同義である。）と、表３に示すＲ１（ここで、Ｒ１は前記と同義である。）を表す置換基Ｒ１－１～Ｒ１－２０３、Ｒ１－５００～Ｒ１－１３１５（ここで、表３の構造式中、波線で切断される結合位置は、表２中のＲ１が結合する位置を表す。）、およびＲ２（ここで、Ｒ２は前記と同義である。）を表す置換基Ｒ２－１～Ｒ２－２０３、Ｒ２－５００～Ｒ２－１３１５（ここで、表３中、波線で切断される結合位置は、表２中のＲ２が結合する位置を表す。）と、表４に示すＲ３（ここで、Ｒ３は前記と同義である。）を表す置換基Ｒ３－１～Ｒ３－１０７６、表５に示すＲ４（ここで、Ｒ４は前記と同義である。）を表す置換基Ｒ４－１～Ｒ４－１１３３、の組み合わせによって表される。これらの化合物は例示のためのものであって、本発明はこれらに限定されるものではない。 Specific compounds of the present invention are those having structural formulas C-1 to C-168 shown in Table 1 (wherein the bond position cut by the wavy line represents the bond position of Het in Table 2), structural formulas Pyra-1 to Pyra-48 shown in Table 2 (wherein R1, R2, R3, R4, Het, and p in Table 2 are as defined above), and substituents R1-1 to R1-203, R1-500 to R1-1315 showing R1 (wherein R1 is as defined above) shown in Table 3 (wherein the bond position cut by the wavy line in the structural formulas in Table 3 represents the bond position of Het in Table 2). , which represents the position where R1 in Table 2 is bonded.) and R2 (where R2 has the same meaning as above), the substituents R2-1 to R2-203, R2-500 to R2-1315 (where the bond position cut by the wavy line in Table 3 represents the position where R2 in Table 2 is bonded) are combined with the substituents R3-1 to R3-1076 which represent R3 (where R3 has the same meaning as above) shown in Table 4, and the substituents R4-1 to R4-1133 which represent R4 (where R4 has the same meaning as above) shown in Table 5. These compounds are given for illustrative purposes only, and the present invention is not limited thereto.
Figure JPOXMLDOC01-appb-T000013
Figure JPOXMLDOC01-appb-T000013
Figure JPOXMLDOC01-appb-T000014
Figure JPOXMLDOC01-appb-T000014
Figure JPOXMLDOC01-appb-T000015
Figure JPOXMLDOC01-appb-T000015
Figure JPOXMLDOC01-appb-T000016
Figure JPOXMLDOC01-appb-T000016
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000020
Figure JPOXMLDOC01-appb-T000020
　以下、例えば、表３及び４中の「２－Ｆ－Ｐｈ」との記載は、２位にフッ素原子が結合しているフェニル基であることを意味し、「２－Ｎ≡Ｃ－Ｐｈ」との記載は、２位にシアノ基が結合しているフェニル基であることを意味し、２－Ｐｙは、ピリジン－２－イル基を表し、３－Ｐｙは、ピリジン－３－イル基を表し、４－Ｐｙは、ピリジン－４－イル基を表し、１－Ｐｙｒａは、１Ｈ－ピラゾール－１－イル基を表し、１－Ｔｒｉａは、１Ｈ－トリアゾール－１－イル基を表し、他の記載も同様である。 For example, in the following Tables 3 and 4, "2-F-Ph" means a phenyl group with a fluorine atom bonded to the 2-position, "2-N≡C-Ph" means a phenyl group with a cyano group bonded to the 2-position, 2-Py represents a pyridin-2-yl group, 3-Py represents a pyridin-3-yl group, 4-Py represents a pyridin-4-yl group, 1-Pyra represents a 1H-pyrazol-1-yl group, 1-Tria represents a 1H-triazol-1-yl group, and the other descriptions are similar.
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000060
　以下に、式（１－１）、および式（１－２）で表される化合物の製造方法を製造方法Ａ～製造方法ＡＰに例示する。本発明化合物の製造方法は、これらに限定されるものではない。 Below, examples of methods for producing the compounds represented by formula (1-1) and formula (1-2) are shown as Production Method A to Production Method AP. The production methods for the compounds of the present invention are not limited to these.
［製造方法Ａ］
Figure JPOXMLDOC01-appb-C000061
 [Production method A]
Figure JPOXMLDOC01-appb-C000061
　式中、Ｒｋは、Ｒ１またはＲ２であり、Ｒ１およびＲ２は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）、または１～２個の酸素原子を含む３～６員環の基を表し、Ｒａは、水素原子、または置換基Ａで適宜置換されてよいＣ１～Ｃ６のアルキル基を表す。 In the formula, Rk is R1 or R2, and R1 and R2 are a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, Rx1Rx2NC (═O)-(wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a C1 to C6 alkoxy group, a C1 to C6 alkoxy group, a C1 to C6 cyclo ... a phenyl group which may be substituted with 0 to 5 substituents, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or Rx1 and Rx2 together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group), Rx3C(=O)- (wherein Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, , C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with 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, phenyl group optionally substituted with 0-5 substituents B, or 5-6 membered aromatic heterocyclic group optionally substituted with 0-4 substituents B. ), Rx3OC(=O)- (where Rx3 is as defined above), Rx4S(O)p- (where Rx4 and p are as defined above), or a 3-6 membered ring group containing 1-2 oxygen atoms, and Ra is a hydrogen atom, or a C1-C6 alkyl group optionally substituted with substituent A.
　製造方法Ａは、本発明化合物の製造中間体を含む式（３－１）および式（３－２）で表される化合物を得る方法であって、式（２）で表される化合物とＲｋ－ＮＨＮＨ２を、溶媒中で反応させることを含む製造方法である。 Production method A is a method for obtaining compounds represented by formula (3-1) and formula (3-2) including production intermediates of the compound of the present invention, and comprises reacting a compound represented by formula (2) with Rk- NHNH2 in a solvent.
　式（３－１）で表される化合物および式（３－２）で表される化合物について、それらの比率はどちらか一方が単独、あるいは任意の割合の混合物であってよく、特に限定されることはない。 The compound represented by formula (3-1) and the compound represented by formula (3-2) may be either alone or in any mixture in any ratio, and there is no particular limitation on their ratio.
　本反応に使用するＲｋ－ＮＨＮＨ２は、市販品として入手または公知の方法で製造することができる。Ｒｋ－ＮＨＮＨ２は、塩酸、臭化水素酸のような酸性化合物との塩を形成したものでもよく、目的とする反応が進行する限りにおいて特に限定されることはない。 The Rk-NHNH 2 used in this reaction can be obtained as a commercial product or produced by a known method. Rk-NHNH 2 may be a salt formed with an acidic compound such as hydrochloric acid or hydrobromic acid, and is not particularly limited as long as the desired reaction proceeds.
　本反応に使用するＲｋ－ＮＨＮＨ２は、式（２）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上２０当量以下である。 The amount of Rk- NHNH2 used in this reaction may be 1 equivalent or more relative to the compound represented by formula (2), and is not particularly limited as long as the intended reaction proceeds, but is preferably 1 equivalent or more and 20 equivalents or less.
　本反応は、酸存在下で実施することが出来る。使用する酸として、塩酸、硫酸等の無機酸類や、酢酸、トリフルオロ酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸等の有機酸類が例示され、目的とする反応が進行する限りにおいて特に限定することはないが、好ましくは、酢酸、またはトリフルオロ酢酸である。また、Ｒｋ－ＮＨＮＨ２と酸性化合物との塩を使用する際には、酸の使用は必須ではない。 This reaction can be carried out in the presence of an acid. Examples of the acid to be used include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and p-toluenesulfonic acid. There is no particular limitation as long as the desired reaction proceeds, but acetic acid or trifluoroacetic acid is preferred. In addition, when using a salt of Rk- NHNH2 and an acidic compound, the use of an acid is not essential.
　本反応に使用する酸の量は、式（２）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上５０当量以下である。また、使用する酸が液体である場合には、溶媒として使用することも可能である。 The amount of acid used in this reaction may be at least 1 equivalent relative to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 50 equivalents. In addition, if the acid used is liquid, it can also be used as a solvent.
　本反応には溶媒を使用することができるが、必ずしも必須ではない。 A solvent can be used in this reaction, but is not essential.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、酢酸、メタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール、トリフルオロエタノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。溶媒として、好ましくは、酸性系溶媒、およびアルコール系溶媒が挙げられ、さらに好ましくは、エタノール、トリフルオロエタノールが挙げられる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples thereof include acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol, isopropanol, and trifluoroethanol, 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, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio. As the solvent, preferably, acidic solvents and alcohol solvents are used, and more preferably, ethanol and trifluoroethanol are used.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（２）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (2).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（３－１）、および式（３－２）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 　The reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－１）、および式（３－２）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained above can be subjected to solvent distillation under reduced pressure as long as the compounds do not decompose.
　溶媒留去後に得られた式（３－１）、および式（３－２）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。精製後、式（３－１）の化合物と式（３－２）の化合物を分離してもよく、目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. After purification, the compounds of formula (3-1) and formula (3-2) may be separated, which may be set appropriately depending on the desired purity.
［製造方法Ｂ］
Figure JPOXMLDOC01-appb-C000062
 [Manufacturing method B]
Figure JPOXMLDOC01-appb-C000062
　式中、Ｒｂは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し、Ｌｖは、メタンスルホニル基、トリフルオロメタンスルホニル基、ｐ‐トルエンスルホニル基、ハロゲン原子、または酸無水物等の脱離基を表し、Ｒ２およびＲａは、前記と同義である。 In the formula, Rb represents a C1-C6 alkyl group which may be substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be substituted with a substituent A, a C2-C6 alkenyl group which may be substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be substituted with a substituent A, a C2-C6 haloalkynyl group, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above), Rx3C(=O)- (wherein Rx3 is as defined above), or Rx3OC(=O)- (wherein Rx3 is as defined above), Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a halogen atom, or an acid anhydride, and R2 and Ra are as defined above.
　製造方法Ｂは、本発明化合物の製造中間体を含む式（３－３）で表される化合物を得る方法であって、式（３－２）で表される化合物とＲｂ－Ｌｖを、塩基の存在下、溶媒中で反応させることを含む製造方法である。 Production method B is a method for obtaining a compound represented by formula (3-3), which includes a production intermediate of the compound of the present invention, and includes reacting a compound represented by formula (3-2) with Rb-Lv in a solvent in the presence of a base.
　本反応に使用するＲｂ－Ｌｖは、市販品として入手または公知の方法で製造することができる。Ｒｂが、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）である化合物を使用する場合、Ｒｂ－Ｌｖは酸無水物を使用してもよい。 The Rb-Lv used in this reaction can be obtained commercially or produced by a known method. When using a compound in which Rb is Rx3C(=O)- (where Rx3 has the same meaning as above), Rb-Lv may be an acid anhydride.
　本反応に使用するＲｂ－Ｌｖの量は、式（３－２）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of Rb-Lv used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3-2), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、１，４－ジアザビシクロ［２．２．２］オクタン、ジメチルアミノピリジン等の有機塩基類、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される。 Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[2.2.2]octane, and dimethylaminopyridine; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
　本反応に使用する塩基の量は、式（３－２）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3-2), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－２）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-2).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸，塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（３－３）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-3) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－３）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-3) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－３）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-3) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｃ］
Figure JPOXMLDOC01-appb-C000063
 [Production Method C]
Figure JPOXMLDOC01-appb-C000063
　式中、Ｒｃはハロゲン原子を表し、ＨａｌＲはハロゲン化剤を表し、Ｒ２、ＲａおよびＲｂは前記と同義である。 In the formula, Rc represents a halogen atom, HalR represents a halogenating agent, and R2, Ra, and Rb are as defined above.
　製造方法Ｃは、Ｒｃがハロゲン原子を表す式（３－４）で表される化合物を得る製造方法であって、式（３－３）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 Production method C is a method for obtaining a compound represented by formula (3-4) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-3) with a halogenating agent (HalR) in a solvent.
　本反応に使用するハロゲン化剤としては、セレクトロフルオル（Ｎ－フルオロ－Ｎ’－トリエチレンジアミン　ビス（テトラフルオロボラート））、Ｎ－クロロスクシンイミド、Ｎ－ブロモスクシンイミド、Ｎ－ヨードスクシンイミド、１，３－ジクロロ－５，５－ジメチルヒダントイン、１，３－ジブロモ－５，５－ジメチルヒダントイン、１，３－ジヨード－５，５－ジメチルヒダントイン、塩素、臭素、ヨウ素等が挙げられる。 Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, chlorine, bromine, iodine, etc.
　本反応に使用するハロゲン化剤の量は、式（３－３）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。ただし、ヒダントインを含むハロゲン化剤の量は、０．５当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはなく、好ましくは、１当量以上５当量以下である。 The amount of halogenating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-3) as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less. However, the amount of halogenating agent containing hydantoin is not particularly limited as long as it is at least 0.5 equivalents as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 5 equivalents or less.
　本反応に使用するハロゲン化剤がヨウ素化剤である場合、塩酸、硫酸等の無機酸類や、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の有機酸のような酸を加えることができる。 When the halogenating agent used in this reaction is an iodinating agent, acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid can be added.
　本反応に使用するハロゲン化剤がヨウ素化剤である場合に使用する酸の量は、式（３－３）で表される化合物に対して０．０１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、０．１当量以上３当量以下である。 When the halogenating agent used in this reaction is an iodinating agent, the amount of acid used is not particularly limited as long as it is 0.01 equivalents or more relative to the compound represented by formula (3-3) and the desired reaction proceeds, but is preferably 0.1 equivalents or more and 3 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、硫酸、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 　The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; ether solvents such as diethyl ether, 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, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－３）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-3).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（３－４）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-4) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－４）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-4) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－４）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-4) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｄ］
Figure JPOXMLDOC01-appb-C000064
 [Manufacturing method D]
Figure JPOXMLDOC01-appb-C000064
　式中、Ｒ５aは、置換基Ａで適宜置換されてよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてよいＣ３～Ｃ８のシクロアルキル基を表し、Ｑは、酸素原子、または硫黄原子を表し、Ｒ２、Ｒａ、ＲｂおよびＲｃは、前記と同義である。 In the formula, R5a represents a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, Q represents an oxygen atom or a sulfur atom, and R2, Ra, Rb, and Rc are as defined above.
　製造方法Ｄは、式（３－５）で表される化合物の合成法であって、式（３－４）で表される化合物とＲ５a－ＱＨ（ここで、Ｒ５aは前記と同義である。）を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method D is a method for synthesizing a compound represented by formula (3-5), which comprises reacting a compound represented by formula (3-4) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
　式（３－４）で表される化合物中、Ｒｃとして好ましくは、塩素原子、臭素原子、またはヨウ素原子であり、さらに好ましくは、臭素原子、またはヨウ素原子であり、特に好ましくは、ヨウ素原子である。 In the compound represented by formula (3-4), Rc is preferably a chlorine atom, a bromine atom, or an iodine atom, more preferably a bromine atom or an iodine atom, and particularly preferably an iodine atom.
　本反応に使用するＲ５a－ＱＨ（ここで、Ｒ５a、およびＱは前記と同義である。）は、市販品として入手または公知の方法で製造できる。
　Ｒ５a－ＯＨとして好ましくは、メタノール、エタノール、プロパノール、イソプロパノール、２，２，２－トリフルオロエタノール、または２，２，３，３，３－ペンタフルオロプロパノールであり、さらに好ましくは、メタノール、エタノール、または２，２，２－トリフルオロエタノールである。
　Ｒ５a－ＳＨとして好ましくは、メチルメルカプタン、エチルメルカプタン、プロピルメルカプタン、イソプロピルメルカプタン、またはブチルメルカプタンであり、さらに好ましくは、メチルメルカプタン、エチルメルカプタン、またはイソプロピルメルカプタンであり、特に好ましくは、エチルメルカプタンである。 R5a-QH (wherein R5a and Q have the same meanings as defined above) used in this reaction is commercially available or can be prepared by a known method.
R5a-OH is preferably methanol, ethanol, propanol, isopropanol, 2,2,2-trifluoroethanol, or 2,2,3,3,3-pentafluoropropanol, and more preferably methanol, ethanol, or 2,2,2-trifluoroethanol.
R5a-SH is preferably methyl mercaptan, ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, or butyl mercaptan, more preferably methyl mercaptan, ethyl mercaptan, or isopropyl mercaptan, and particularly preferably ethyl mercaptan.
　本反応に使用するＲ５a－ＱＨの量は、式（３－４）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上２０当量以下である。 The amount of R5a-QH used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-4) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 20 equivalents.
　本反応は遷移金属類を用いたカップリング反応によって実施することが出来る、本反応に使用する遷移金属類は、配位子を有してよく、酢酸パラジウム、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウムジクロリド、トリス（ジベンジリデンアセトン）ジパラジウム、テトラキス（トリフェニルホスフィン）パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド等のパラジウム類等である。 This reaction can be carried out by a coupling reaction using transition metals. The transition metals used in this reaction may have a ligand, and include palladium compounds such as palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, and bis(triphenylphosphine)palladium dichloride.
　本反応に使用する遷移金属類の量は、式（３－４）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of transition metals used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (3-4), but is not particularly limited as long as the desired reaction proceeds.
　本反応を効率的に進行させるために、トリフェニルホスフィン、１，１’－ビス（ジフェニルホスフィノ）フェロセン、２－ジシクロヘキシルホスフィノ－２’４’６’－トリイソプロピルビフェニル、２－ジ－ｔ－ブチルホスフィノ－２’４’６’－トリイソプロピルビフェニル、４，５－ビス（ジフェニルホスフィノ）－９，９－ジメチルキサンテン等のホスフィン配位子を添加することができる。 To make this reaction proceed efficiently, phosphine ligands such as triphenylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, 2-di-t-butylphosphino-2'4'6'-triisopropylbiphenyl, and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene can be added.
　本反応に使用するホスフィン配位子の量は、式（３－４）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of phosphine ligand used in this reaction is 0.001 equivalents or more and 1 equivalent or less relative to the compound represented by formula (3-4), but is not particularly limited as long as the desired reaction proceeds.
　本反応に使用する塩基は、炭酸ナトリウム、炭酸カリウム、炭酸セシウムのような無機塩基類やトリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン等の有機塩基類等である。 The bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate, and organic bases such as triethylamine, tributylamine, and diisopropylethylamine.
　本反応に使用する塩基の量は、式（３－４）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上５０当量以下である。 The amount of base used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-4) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 50 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、メタノール、エタノール、ｔ－ブチルアルコール等で表されるアルコール溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include alcohol solvents such as methanol, ethanol, and t-butyl alcohol; ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－４）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-4).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、３０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 30°C and 180°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、濾過操作を行うことにより、不溶物を除去することも可能であるが必須ではない。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, it is possible to arbitrarily use an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary. In addition, these solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield. In addition, it is possible to remove insoluble matter by performing a filtration operation, but this is not essential.
　前記で得られた式（３－５）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-5) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－５）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-5) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－５）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-5) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｅ］
Figure JPOXMLDOC01-appb-C000065
 [Manufacturing method E]
Figure JPOXMLDOC01-appb-C000065
　式中、Ｒｄは、置換基Ａで適宜置換されてよいＣ１～Ｃ６のアルキル基を表し、Ｒ２、Ｒ５ａ、Ｑ、およびＲｂは、前記と同義である。 In the formula, Rd represents a C1-C6 alkyl group which may be appropriately substituted with a substituent A, and R2, R5a, Q, and Rb are as defined above.
　製造方法Ｅは、式（３－６）で表される化合物の合成方法であって、式（３－５）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 　Production method E is a method for synthesizing a compound represented by formula (3-6), which includes reacting a compound represented by formula (3-5) in a solvent under acidic or basic conditions.
　まず、酸性条件の反応について説明する。 First, let's explain the reaction under acidic conditions.
　本反応に使用する酸は、塩酸、臭化水素酸、リン酸等の無機酸類や、酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等の有機酸類が例示される。目的とする反応が進行する限り特に制限されることはない。 The acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, etc., or organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. There are no particular limitations as long as the desired reaction proceeds.
　本反応に使用する酸の量は、触媒量でもよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、式（３－５）で表される化合物に対して０．０１当量以上である。また、液体状の酸に関しては溶媒として使用することも可能である。 The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more relative to the compound represented by formula (3-5). In addition, liquid acids can also be used as a solvent.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、酢酸、メタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 　The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, 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, and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－５）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-5).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
　次に、塩基性条件の反応について説明する。 Next, we will explain the reaction under basic conditions.
　本反応に使用する塩基は、水酸化リチウム、水酸化ナトリウム、水酸化カリウム等の無機塩基類が例示されるが、目的とする反応が進行する限りにおいて特に限定されることはない。 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 desired reaction proceeds.
　本反応に使用する塩基は、式（３－５）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上３０当量以下である。 The amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-5), but is preferably 1 equivalent or more and 30 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and the like, alcohol solvents such as methanol, ethanol, isopropanol, and the like, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, and the like, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and the like. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－５）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-5).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
　反応の後処理は、酸性条件での反応と塩基性条件の反応は共通の方法で行える。反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　Reactions under acidic and basic conditions can be treated by the same method after the reaction. A separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using 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, or saline solution can be used as desired. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary. These solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
　前記で得られた式（３－６）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-6) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－６）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-6) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－６）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-6) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｆ］
Figure JPOXMLDOC01-appb-C000066
 [Manufacturing method F]
Figure JPOXMLDOC01-appb-C000066
　式中、ｒは、１または２の整数を表し、Ｏｘは酸化剤を表し、Ｒ２、Ｒ５ａ、ＲａおよびＲｂは、前記と同義である。 In the formula, r represents an integer of 1 or 2, Ox represents an oxidizing agent, and R2, R5a, Ra, and Rb are as defined above.
　製造方法Ｆは、式（３－７）で表される化合物を得る方法であって、式（３－６ａ）で表される化合物と酸化剤（Ｏｘ）とを、溶媒中で反応させることを含む製造方法である。 　Production method F is a method for obtaining a compound represented by formula (3-7), which includes reacting a compound represented by formula (3-6a) with an oxidizing agent (Ox) in a solvent.
　本反応に使用する酸化剤は、過酸化水素水、メタ－クロロ過安息香酸等の過酸化物類等が挙げられる。また、タングステン酸ナトリウムのような遷移金属類を添加することもできる。 The oxidizing agent used in this reaction includes peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid. Transition metals such as sodium tungstate can also be added.
　本反応に使用する酸化剤の量は、式（３－７）中、ｒが１の整数で表される化合物を製造する際は式（３－６ａ）で表される化合物に対して、通常、１．０当量以上１．２当量未満であり、式（３－７）中、ｒが２の整数で表される化合物を製造する際は、通常、２当量以上１０当量以下である。また、遷移金属類を添加する際には、遷移金属の添加量は、通常、０．００１当量以上１当量以下である。 The amount of oxidizing agent used in this reaction is usually 1.0 equivalent or more and less than 1.2 equivalents relative to the compound represented by formula (3-6a) when producing a compound represented by formula (3-7) where r is an integer of 1, and usually 2 equivalents or more and 10 equivalents or less when producing a compound represented by formula (3-7) where r is an integer of 2. In addition, when a transition metal is added, the amount of transition metal added is usually 0.001 equivalent or more and 1 equivalent or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、酢酸等の酸性系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、アセトニトリル等のニトリル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water solvents, acidic solvents such as acetic acid, benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, nitrile-based solvents such as acetonitrile, and halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－６ａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-6a).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１２０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 120°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（３－７）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-7) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－７）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-7) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－７）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-7) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｇ］
Figure JPOXMLDOC01-appb-C000067
 [Manufacturing method G]
Figure JPOXMLDOC01-appb-C000067
　式中、Ｒｄは、置換基Ａで適宜置換されてよいＣ１～Ｃ６のアルキル基を表し、Ｒ２、Ｒ５ａ、Ｒｂ、およびｒは、前記と同義である。 In the formula, Rd represents a C1-C6 alkyl group which may be appropriately substituted with a substituent A, and R2, R5a, Rb, and r are as defined above.
　製造方法Ｇは、式（３－８）で表される化合物の合成方法であって、式（３－７）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 　Production method G is a method for synthesizing a compound represented by formula (3-8), which includes reacting a compound represented by formula (3-7) in a solvent under acidic or basic conditions.
　まず、酸性条件の反応について説明する。 First, let's explain the reaction under acidic conditions.
　本反応に使用する酸は、塩酸、臭化水素酸、リン酸等の無機酸類や、酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等の有機酸類が例示される。目的とする反応が進行する限り特に制限されることはない。 The acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, etc., or organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. There are no particular limitations as long as the desired reaction proceeds.
　本反応に使用する酸の量は、触媒量でもよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、式（３－７）で表される化合物に対して０．０１当量以上である。また、液体状の酸に関しては溶媒として使用することも可能である。 The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more relative to the compound represented by formula (3-7). In addition, liquid acids can also be used as a solvent.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、酢酸、メタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 　The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, 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, and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－７）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-7).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
　次に、塩基性条件の反応について説明する。 Next, we will explain the reaction under basic conditions.
　本反応に使用する塩基は、水酸化リチウム、水酸化ナトリウム、水酸化カリウム等の無機塩基類が例示されるが、目的とする反応が進行する限りにおいて特に限定されることはない。 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 desired reaction proceeds.
　本反応に使用する塩基は、式（３－７）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上３０当量以下である。 The amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-7), but is preferably 1 equivalent or more and 30 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and the like, alcohol solvents such as methanol, ethanol, isopropanol, and the like, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, and the like, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and the like. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－７）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-7).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
　反応の後処理は、酸性条件での反応と塩基性条件の反応は共通の方法で行える。反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　Reactions under acidic and basic conditions can be treated by the same method after the reaction. A separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using 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, or saline solution can be used as desired. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary. These solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
　前記で得られた式（３－８）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-8) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－８）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-8) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－８）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-8) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｈ］
Figure JPOXMLDOC01-appb-C000068
 [Manufacturing method H]
Figure JPOXMLDOC01-appb-C000068
　式中、Ｒａ、Ｒ１、Ｒｂ、およびＬｖは、前記と同義である。 In the formula, Ra, R1, Rb, and Lv are as defined above.
　製造方法Ｈは、本発明化合物の製造中間体を含む式（３－９）で表される化合物を得る方法であって、式（３－１）で表される化合物とＲｂ－Ｌｖを、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method H is a method for obtaining a compound represented by formula (3-9), which includes a production intermediate of the compound of the present invention, and includes reacting a compound represented by formula (3-1) with Rb-Lv in a solvent in the presence of a base.
　製造方法Ｂにおける式（３－２）で表される化合物を式（３－１）で表される化合物に代えて使用することにより、製造方法Ｂに準じて製造方法Ｈを実施することができる。 By using the compound represented by formula (3-2) in place of the compound represented by formula (3-1) in manufacturing method B, manufacturing method H can be carried out in accordance with manufacturing method B.
［製造方法Ｉ］
Figure JPOXMLDOC01-appb-C000069
　式中、Ｒａ、Ｒ１、Ｒｂ、ＲｃおよびＨａｌＲは、前記と同義である。 [Production Method I]
Figure JPOXMLDOC01-appb-C000069
In the formula, Ra, R1, Rb, Rc and HalR are as defined above.
　製造方法Ｉは、Ｒｃがハロゲン原子を表す式（３－１０）で表される化合物を得る製造方法であって、式（３－９）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 Production method I is a method for obtaining a compound represented by formula (3-10) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-9) with a halogenating agent (HalR) in a solvent.
　製造方法Ｃにおける式（３－３）で表される化合物を式（３－９）で表される化合物に代えて使用することにより、製造方法Ｃに準じて製造方法Ｉを実施することができる。 By using the compound represented by formula (3-3) in place of the compound represented by formula (3-9) in production method C, production method I can be carried out in accordance with production method C.
［製造方法Ｊ］
Figure JPOXMLDOC01-appb-C000070
　式中、Ｒ１、Ｒ５ａ、Ｑ、Ｒａ、Ｒｂ、およびＲｃは、前記と同義である。 [Manufacturing method J]
Figure JPOXMLDOC01-appb-C000070
In the formula, R1, R5a, Q, Ra, Rb, and Rc are as defined above.
　製造方法Ｊは、式（３－１１）で表される化合物の合成法であって、式（３－１０）で表される化合物とＲ５ａ－ＱＨ（ここで、Ｒ５ａ、およびＱは前記と同義である。）を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method J is a method for synthesizing a compound represented by formula (3-11), which comprises reacting a compound represented by formula (3-10) with R5a-QH (wherein R5a and Q are as defined above) in a solvent in the presence of a base.
　製造方法Ｄにおける式（３－４）で表される化合物を式（３－１０）で表される化合物に代えて使用することにより、製造方法Ｄに準じて製造方法Ｊを実施することができる。 By replacing the compound represented by formula (3-4) in production method D with the compound represented by formula (3-10), production method J can be carried out in accordance with production method D.
［製造方法Ｋ］
Figure JPOXMLDOC01-appb-C000071
　式中、Ｒ１、Ｒ５ａ、Ｒｂ、Ｒｄは、前記と同義である。 [Manufacturing method K]
Figure JPOXMLDOC01-appb-C000071
In the formula, R1, R5a, Rb, and Rd are defined as above.
　製造方法Ｋは、式（３－１３）で表される化合物の合成方法であって、式（３－１２）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 　Production method K is a method for synthesizing a compound represented by formula (3-13), which includes reacting a compound represented by formula (3-12) in a solvent under acidic or basic conditions.
　製造方法Ｅにおける式（３－５）で表される化合物を式（３－１２）で表される化合物に代えて使用することにより、製造方法Ｅに準じて製造方法Ｋを実施することができる。 By replacing the compound represented by formula (3-5) in manufacturing method E with the compound represented by formula (3-12), manufacturing method K can be carried out in accordance with manufacturing method E.
［製造方法Ｌ］
Figure JPOXMLDOC01-appb-C000072
 [Production method L]
Figure JPOXMLDOC01-appb-C000072
　式中、Ｒ１、Ｒ５ａ、Ｒａ、Ｒｂ、ｒ、およびＯｘは、前記と同義である。 In the formula, R1, R5a, Ra, Rb, r, and Ox are as defined above.
　製造方法Ｌは、式（３－１４）で表される化合物を得る方法であって、式（３－６ｂ）で表される化合物と酸化剤（Ｏｘ）とを、溶媒中で反応させることを含む製造方法である。 　Production method L is a method for obtaining a compound represented by formula (3-14), which includes reacting a compound represented by formula (3-6b) with an oxidizing agent (Ox) in a solvent.
　製造方法Ｆにおける式（３－６ａ）で表される化合物を式（３－６ｂ）で表される化合物に代えて使用することにより、製造方法Ｆに準じて製造方法Ｌを実施することができる。 By using the compound represented by formula (3-6a) in place of the compound represented by formula (3-6b) in production method F, production method L can be carried out in accordance with production method F.
［製造方法Ｍ］
Figure JPOXMLDOC01-appb-C000073
 [Manufacturing method M]
Figure JPOXMLDOC01-appb-C000073
　式中、Ｒ１、Ｒ５ａ、Ｒｂ、Ｒｄ、およびｒは、前記と同義である。 In the formula, R1, R5a, Rb, Rd, and r are as defined above.
　製造方法Ｍは、式（３－１６）で表される化合物の合成方法であって、式（３－１５）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 　Production method M is a method for synthesizing a compound represented by formula (3-16), which includes reacting a compound represented by formula (3-15) in a solvent under acidic or basic conditions.
　製造方法Ｇにおける式（３－７）で表される化合物を式（３－１５）で表される化合物に代えて使用することにより、製造方法Ｇに準じて製造方法Ｍを実施することができる。 By using the compound represented by formula (3-15) instead of the compound represented by formula (3-7) in manufacturing method G, manufacturing method M can be carried out in accordance with manufacturing method G.
［製造方法Ｎ］
Figure JPOXMLDOC01-appb-C000074
 [Manufacturing method N]
Figure JPOXMLDOC01-appb-C000074
　式中、Ｒ６は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ２、Ｒｃ、Ｒｄ、およびＨａｌＲは、前記と同義である。 In the formula, R6 represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group, and R2, Rc, Rd, and HalR are as defined above.
　製造方法Ｎは、Ｒｃがハロゲン原子を表す式（３－１８）で表される化合物を得る製造方法であって、式（３－１７）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である Production method N is a method for obtaining a compound represented by formula (3-18) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-17) with a halogenating agent (HalR) in a solvent.
　製造方法Ｃにおける式（３－３）で表される化合物を式（３－１７）で表される化合物に代えて使用することにより、製造方法Ｃに準じて製造方法Ｎを実施することができる。 By replacing the compound represented by formula (3-3) in manufacturing method C with the compound represented by formula (3-17), manufacturing method N can be carried out in accordance with manufacturing method C.
［製造方法Ｏ］
Figure JPOXMLDOC01-appb-C000075
 [Manufacturing method O]
Figure JPOXMLDOC01-appb-C000075
　式中、Ｒｅはハロゲン原子を表し、ＨａｌＲはハロゲン化剤を表し、Ｒ２、Ｒ６、ＲｃおよびＲｄは前記と同義である。 In the formula, Re represents a halogen atom, HalR represents a halogenating agent, and R2, R6, Rc, and Rd are as defined above.
　製造方法Ｏは、Ｒｅがハロゲン原子を表す式（３－１９）で表される化合物を得る製造方法であって、式（３－１８）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 Production method O is a method for obtaining a compound represented by formula (3-19) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-18) with a halogenating agent (HalR) in a solvent.
　本反応に使用するハロゲン化剤としては、セレクトロフルオル（Ｎ－フルオロ－Ｎ’－トリエチレンジアミン　ビス（テトラフルオロボラート））、Ｎ－クロロスクシンイミド、Ｎ－ブロモスクシンイミド、Ｎ－ヨードスクシンイミド、１，３－ジクロロ－５，５－ジメチルヒダントイン、１，３－ジブロモ－５，５－ジメチルヒダントイン、１，３－ジヨード－５，５－ジメチルヒダントイン、臭素、ヨウ素、トリメチルフェニルアンモニウムトリブロミド、ベンジルトリメチルアンモニウムトリブロミド等が挙げられる。 Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine, trimethylphenylammonium tribromide, benzyltrimethylammonium tribromide, etc.
　本反応に使用するハロゲン化剤の量は、式（３－１８）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。ただし、ヒダントインを含むハロゲン化剤の量は、０．５当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはなく、好ましくは、１当量以上５当量以下である。 The amount of halogenating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-18) as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less. However, the amount of halogenating agent containing hydantoin is not particularly limited as long as it is at least 0.5 equivalents as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 5 equivalents or less.
　本反応に使用するハロゲン化剤がヨウ素化剤である場合、塩酸、硫酸等の無機酸類や、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の有機酸のような酸を加えることができる。 When the halogenating agent used in this reaction is an iodinating agent, acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid can be added.
　本反応に使用するハロゲン化剤がヨウ素化剤である場合に使用する酸の量は、式（３－１８）で表される化合物に対して０．０１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、０．１当量以上３当量以下である。 When the halogenating agent used in this reaction is an iodinating agent, the amount of acid used is not particularly limited as long as it is 0.01 equivalents or more relative to the compound represented by formula (3-18) and the desired reaction proceeds, but is preferably 0.1 equivalents or more and 3 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、硫酸、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 　The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; ether solvents such as diethyl ether, 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, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－１８）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-18).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（３－１９）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (3-19) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（３－１９）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (3-19) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（３－１９）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (3-19) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｐ］
Figure JPOXMLDOC01-appb-C000076
　式中、Ｒ２、Ｒ５ａ、Ｒ６、Ｒｃ、およびＲｄは、前記と同義である。 [Manufacturing method P]
Figure JPOXMLDOC01-appb-C000076
In the formula, R2, R5a, R6, Rc, and Rd are defined as above.
　製造方法Ｐは、式（３－２０）で表される化合物の合成法であって、式（３－１８）で表される化合物とＲ５ａ－ＱＨ（ここで、Ｒ５ａ、およびＱは前記と同義である。）を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method P is a method for synthesizing a compound represented by formula (3-20), which comprises reacting a compound represented by formula (3-18) with R5a-QH (wherein R5a and Q are as defined above) in a solvent in the presence of a base.
　製造方法Ｄにおける式（３－４）で表される化合物を式（３－１８）で表される化合物に代えて使用することにより、製造方法Ｄに準じて製造方法Ｐを実施することができる。 By replacing the compound represented by formula (3-4) in manufacturing method D with the compound represented by formula (3-18), manufacturing method P can be carried out in accordance with manufacturing method D.
［製造方法Ｑ］
Figure JPOXMLDOC01-appb-C000077
　式中、ＨａｌＲはハロゲン化剤を表し、Ｒ２、Ｒ５ａ、Ｑ、Ｒ６、ＲｄおよびＲｅは前記と同義である。 [Manufacturing method Q]
Figure JPOXMLDOC01-appb-C000077
In the formula, HalR represents a halogenating agent, and R2, R5a, Q, R6, Rd and Re are as defined above.
　製造方法Ｑは、Ｒｅがハロゲン原子を表す式（３－２１）で表される化合物を得る製造方法であって、式（３－２０）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 Production method Q is a method for obtaining a compound represented by formula (3-21) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-20) with a halogenating agent (HalR) in a solvent.
　製造方法Ｏにおける式（３－１８）で表される化合物を式（３－２０）で表される化合物に代えて使用することにより、製造方法Ｏに準じて製造方法Ｑを実施することができる。 By replacing the compound represented by formula (3-18) in manufacturing method O with the compound represented by formula (3-20), manufacturing method Q can be carried out in accordance with manufacturing method O.
［製造方法Ｒ］
Figure JPOXMLDOC01-appb-C000078
 [Manufacturing method R]
Figure JPOXMLDOC01-appb-C000078
　式中、Ｒ１、Ｒ６、Ｒｃ、Ｒｄ、およびＨａｌＲは、前記と同義である。 In the formula, R1, R6, Rc, Rd, and HalR are as defined above.
　製造方法Ｒは、Ｒｃがハロゲン原子を表す式（３－２３）で表される化合物を得る製造方法であって、式（３－２２）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 　Production method R is a production method for obtaining a compound represented by formula (3-23) in which Rc represents a halogen atom, and includes reacting a compound represented by formula (3-22) with a halogenating agent (HalR) in a solvent.
　製造方法Ｃにおける式（３－３）で表される化合物を式（３－２２）で表される化合物に代えて使用することにより、製造方法Ｃに準じて製造方法Ｒを実施することができる。 By using the compound represented by formula (3-22) instead of the compound represented by formula (3-3) in manufacturing method C, manufacturing method R can be carried out in accordance with manufacturing method C.
［製造方法Ｓ］
Figure JPOXMLDOC01-appb-C000079
 [Manufacturing method S]
Figure JPOXMLDOC01-appb-C000079
　式中、Ｒ１、Ｒ６、Ｒｃ、Ｒｄ、ＲｅおよびＨａｌＲは、前記と同義である。 In the formula, R1, R6, Rc, Rd, Re and HalR are as defined above.
　製造方法Ｓは、Ｒｅがハロゲン原子を表す式（３－２４）で表される化合物を得る製造方法であって、式（３－２３）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 Production method S is a method for obtaining a compound represented by formula (3-24) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-23) with a halogenating agent (HalR) in a solvent.
　製造方法Ｏにおける式（３－１８）で表される化合物を式（３－２３）で表される化合物に代えて使用することにより、製造方法Ｏに準じて製造方法Ｓを実施することができる。 By replacing the compound represented by formula (3-18) in manufacturing method O with the compound represented by formula (3-23), manufacturing method S can be carried out in accordance with manufacturing method O.
［製造方法Ｔ］
Figure JPOXMLDOC01-appb-C000080
　式中、Ｒ１、Ｒ５ａ、Ｑ、Ｒ６、Ｒｃ、およびＲｄは、前記と同義である。 [Manufacturing method T]
Figure JPOXMLDOC01-appb-C000080
In the formula, R1, R5a, Q, R6, Rc, and Rd are as defined above.
　製造方法Ｔは、式（３－２５）で表される化合物の合成法であって、式（３－２３）で表される化合物とＲ５ａ－ＱＨ（ここで、Ｒ５ａは前記と同義である。）を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method T is a method for synthesizing a compound represented by formula (3-25), which comprises reacting a compound represented by formula (3-23) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
　製造方法Ｄにおける式（３－４）で表される化合物を式（３－２３）で表される化合物に代えて使用することにより、製造方法Ｄに準じて製造方法Ｔを実施することができる。 By substituting the compound represented by formula (3-23) for the compound represented by formula (3-4) in production method D, production method T can be carried out in accordance with production method D.
［製造方法Ｕ］
Figure JPOXMLDOC01-appb-C000081
　式中、ＨａｌＲはハロゲン化剤を表し、Ｒ１、Ｒ５ａ、Ｑ、Ｒ６、Ｒｄ、およびＲｅは前記と同義である。 [Production method U]
Figure JPOXMLDOC01-appb-C000081
In the formula, HalR represents a halogenating agent, and R1, R5a, Q, R6, Rd, and Re are as defined above.
　製造方法Ｕは、Ｒｅがハロゲン原子を表す式（３－２６）で表される化合物を得る製造方法であって、式（３－２５）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 　Production method U is a method for obtaining a compound represented by formula (3-26) in which Re represents a halogen atom, and includes reacting a compound represented by formula (3-25) with a halogenating agent (HalR) in a solvent.
　製造方法Ｏにおける式（３－１８）で表される化合物を式（３－２５）で表される化合物に代えて使用することにより、製造方法Ｏに準じて製造方法Ｕを実施することができる。 By replacing the compound represented by formula (3-18) in manufacturing method O with the compound represented by formula (3-25), manufacturing method U can be carried out in accordance with manufacturing method O.
［製造方法Ｖ］
Figure JPOXMLDOC01-appb-C000082
 [Manufacturing Method V]
Figure JPOXMLDOC01-appb-C000082
　式中、Ｒ７は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ８は、水素原子、水酸基、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し、Ｒ９は、水素原子、水酸基、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し、Ｒ１０は、水素原子、水酸基、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し、Ｌｖ２は、スルホナート基、メシチルスルホナート基、２，４－ジニトロフェノキシ基、ジフェニルホスフィネート基等の脱離基を表す。 In the formula, R7 represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group; R8 represents a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group. , a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a substituted R9 represents a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkynyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group, a C1-C6 alkoxy group, a C1-C6 alkoxy group, a C1-C6 alkoxy group, a C3-C8 alkoxy group, a C1-C6 ... cycloalkoxy group or Rx4S(O)p- (wherein Rx4 and p are as defined above), R10 represents a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group which may be appropriately substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be appropriately substituted with a substituent A, a C1-C6 alkoxy group which may be appropriately substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group which may be appropriately substituted with a substituent A, or Rx4S(O)p- (wherein Rx4 and p are as defined above), and Lv2 represents a leaving group such as a sulfonate group, a mesitylsulfonate group, a 2,4-dinitrophenoxy group, or a diphenylphosphinate group.
　製造方法Ｖは、式（４－２）で表される化合物を得る製造方法であって、式（４－１）で表される化合物とアミノ化剤（ＮＨ２－Ｌｖ２）とを、溶媒中で反応させることを含む製造方法である。 Production method V is a production method for obtaining a compound represented by formula (4-2), which comprises reacting a compound represented by formula (4-1) with an aminating agent (NH 2 -Lv2) in a solvent.
　本反応に使用するアミノ化剤としては、ヒドロキシルアミン－Ｏ－スルホン酸、Ｏ－（ジフェニルホスフィニル）ヒドロキシルアミン、（Ｏ－（メシチルスルホニル）ヒドロキシルアミン）、Ｏ－（２，４－ジニトロフェニル）ヒドロキシルアミン等が挙げられる。 Aminating agents used in this reaction include hydroxylamine-O-sulfonic acid, O-(diphenylphosphinyl)hydroxylamine, (O-(mesitylsulfonyl)hydroxylamine), O-(2,4-dinitrophenyl)hydroxylamine, etc.
　本反応に使用するアミノ化剤の量は、式（４－１）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下であり、好ましくは、１当量以上５当量以下である。 The amount of the aminating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (4-1) and the desired reaction proceeds, but is preferably at least 1 equivalent and at most 10 equivalents, and more preferably at least 1 equivalent and at most 5 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、硫酸、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 　The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; ether solvents such as diethyl ether, 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, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（４－１）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (4-1).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（４－２）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (4-2) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（４－２）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (4-2) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（４－２）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (4-2) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｗ］
Figure JPOXMLDOC01-appb-C000083
 [Manufacturing method W]
Figure JPOXMLDOC01-appb-C000083
　式中、Ｒ５は、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し、Ｒ２、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｒｂ、Ｌｖ２は、前記と同義である。 In the formula, R5 is a cyano group, a halogen atom, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or Rx4S(O)p- (wherein Rx4 is a hydroxyl group, a halogen atom, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group which may be appropriately substituted with substituent A, C2-C6 alkenyl group which may be appropriately substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group which may be appropriately substituted with substituent A, C2-C6 haloalkynyl group, or phenyl group which may be appropriately substituted with 0-5 substituents B, and p represents an integer of 0, 1, or 2. ) and R2, R7, R8, R9, R10, Rb, and Lv2 are as defined above.
　製造方法Ｗは、式（１－ａ）で表される本発明化合物を得る製造方法であって、式（４－２）で表される化合物と式（３－２７）で表される化合物を、溶媒中で反応させることを含む製造方法である。 　Production method W is a production method for obtaining the compound of the present invention represented by formula (1-a), which includes reacting a compound represented by formula (4-2) with a compound represented by formula (3-27) in a solvent.
　本反応は、式（３－２７）で表されるピラゾールカルボン酸をカルボン酸ハロゲン化物へと変換した後に式（４－２）で表される化合物と塩基存在下で反応させることが出来る。また、式（３－２７）で表されるピラゾールカルボン酸と式（４－２）で表される化合物とを縮合剤を用いて、塩基存在下で反応させることが出来る。 In this reaction, the pyrazole carboxylic acid represented by formula (3-27) can be converted into an carboxylic acid halide and then reacted with a compound represented by formula (4-2) in the presence of a base. In addition, the pyrazole carboxylic acid represented by formula (3-27) can be reacted with a compound represented by formula (4-2) in the presence of a base using a condensing agent.
　まず、式（３－２７）で表される化合物をカルボン酸ハロゲン化物へと合成する反応について説明する。 First, we will explain the reaction for synthesizing the compound represented by formula (3-27) into an carboxylic acid halide.
カルボン酸ハロゲン化物を合成するハロゲン化剤としては、塩化チオニル、塩化オキサリル、塩化ホスホリル、塩化スルフリル、三塩化リン、五塩化リン、三臭化リン等が挙げられる。 Halogenating agents used to synthesize carboxylic acid halides include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide, etc.
　本反応に使用するハロゲン化剤の量は、式（３－２７）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of halogenating agent used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (3-27) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　カルボン酸ハロゲン化物を合成する場合、触媒としてＮ，Ｎ－ジメチルホルムアミドを共存させることが出来る。本反応に使用する触媒の量は、式（３－２７）で表される化合物に対して、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、０．０１当量以上１０当量以下である。 When synthesizing carboxylic acid halides, N,N-dimethylformamide can be used as a catalyst. The amount of catalyst used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (3-27), but is preferably 0.01 equivalents or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.; ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc.; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc.; urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc.; and halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－２７）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-27).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C, or below the boiling point of the solvent.
　前記で得られたカルボン酸ハロゲン化物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the carboxylic acid halide obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られたカルボン酸ハロゲン化物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the carboxylic acid halide obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られたカルボン酸ハロゲン化物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the carboxylic acid halide obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. The method can be set appropriately depending on the desired purity.
　次に、式（４－２）で表される化合物と前記で得られたカルボン酸ハロゲン化物との塩基存在下での反応について説明する。 Next, we will explain the reaction of the compound represented by formula (4-2) with the carboxylic acid halide obtained above in the presence of a base.
　本反応に使用する前記で得られたカルボン酸ハロゲン化物の量は、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、式（４－２）で表される化合物に対して、１当量以上１０当量以下である。
　次に、塩基存在下での反応について説明する。 The amount of the carboxylic acid halide obtained above to be used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less relative to the compound represented by formula (4-2).
Next, the reaction in the presence of a base will be described.
　本反応に使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、１，４－ジアザビシクロ［２．２．２］オクタン等の有機塩基類、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される Examples of bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
　本反応に使用する塩基は、式（３－２７）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上３０当量以下である。 The amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-27), but is preferably 1 equivalent or more and 30 equivalents or less.
　本反応には、活性化剤として触媒を用いることが出来る。触媒として、４－ジメチルアミノピリジン、４－ピロリジノピリジン等が挙げられる。 A catalyst can be used as an activator for this reaction. Examples of catalysts include 4-dimethylaminopyridine and 4-pyrrolidinopyridine.
本反応に使用する触媒の量は、式（４－２）で表される化合物に対して、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、０．０１当量以上１０当量以下である。 The amount of catalyst used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (4-2), but is preferably 0.01 equivalents or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、硫酸、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid; 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, and butyl acetate; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（４－２）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (4-2).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、濾過操作を行うことにより、不溶物を除去することも可能であるが必須ではない。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, it is possible to arbitrarily use an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary. In addition, these solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield. In addition, it is possible to remove insoluble matter by performing a filtration operation, but this is not essential.
　前記で得られた式（１－ａ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ａ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ａ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。 The reaction mixture containing the compound represented by formula (1-a) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.
　次に、式（３－２７）で表される化合物と式（４－２）で表される化合物とを、縮合剤を用いて、塩基存在下で反応させる方法について説明する。 Next, we will explain a method of reacting a compound represented by formula (3-27) with a compound represented by formula (4-2) in the presence of a base using a condensing agent.
　本反応に使用する式（３－２７）の量は、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、式（４－２）で表される化合物に対して、１当量以上１０当量以下である。 The amount of formula (3-27) used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent or more and 10 equivalents or less relative to the compound represented by formula (4-2).
　本反応に使用する縮合剤として、塩酸１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド、１－［３－（ジメチルアミノ）プロピル］－３－エチルカルボジイミド、Ｎ，Ｎ’－ジシクロヘキシルカルボジイミド、Ｎ，Ｎ’－ジイソプロピルカルボジイミド等のカルボジイミド系縮合剤、Ｎ，Ｎ’－カルボニルジイミダゾール、１，１’－カルボニルジ（１，２，４－トリアゾール）等のイミダゾール系脱水縮合剤、４－（４，６－ジメトキシ－１，３，５－トリアジン－２－イル）－４－メチルモルホリニウム＝クロリド等のトリアジン系縮合剤、１Ｈ－ベンゾトリアゾール－１－イルオキシトリス（ジメチルアミノ）ホスホニウムヘキサフルオロリン酸塩、１Ｈ－ベンゾトリアゾール－１－イルオキシトリピロリジノホスホニウムヘキサフルオロホスファート、１－［ビス（ジメチルアミノ）メチレン］－１Ｈ－１，２，３－トリアゾロ［４，５－ｂ］ピリジニウム３－オキシドヘキサフルオロホスファート等のホスホニウム系脱水縮合剤、｛｛［（１－シアノ－２－エトキシ－２－オキソエチリデン）アミノ］オキシ｝－４－モルホニノメチレン｝ジメチルアンモニウムヘキサフルオロリン酸塩、Ｏ－（ベンゾトリアゾール－１－イル）－Ｎ，Ｎ，Ｎ’，Ｎ’，－テトラメチルウロニウムヘキサフルオロリン酸塩、Ｏ－（７－アザベンゾトリアゾール－１－イル）－Ｎ，Ｎ，Ｎ’，Ｎ’，－テトラメチルウロニウムヘキサフルオロリン酸塩等のウロニウム系縮合剤、２－クロロ－１，３－ジメチルイミダゾリニウムヘキサフルオロリン酸塩、１－（クロロ－１－ピロリジニルメチレン）ピロリジニウムヘキサフルオロリン酸塩等のハロウロニウム系縮合剤、２－クロロ－１－メチルピリジニウムヨージド等が挙げられる。 Condensing agents used in this reaction include carbodiimide-based condensing agents such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, N,N'-dicyclohexylcarbodiimide, and N,N'-diisopropylcarbodiimide; imidazole-based dehydration condensing agents such as N,N'-carbonyldiimidazole and 1,1'-carbonyldi(1,2,4-triazole); triazine-based condensing agents such as 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, and 1-[bis(dimethylamino)methylene ]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and other phosphonium-based dehydration condensation agents, {{[(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy}-4-morpholinomethylene}dimethylammonium hexafluorophosphate, O-(benzotriazol-1-yl)-N,N,N',N',-tetramethyluronium hexafluorophosphate, salts, uronium-based condensing agents such as O-(7-azabenzotriazol-1-yl)-N,N,N',N',-tetramethyluronium hexafluorophosphate, haluronium-based condensing agents such as 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate and 1-(chloro-1-pyrrolidinylmethylene)pyrrolidinium hexafluorophosphate, and 2-chloro-1-methylpyridinium iodide.
　本反応に使用する縮合剤の量は、式（３－２７）で表される化合物に対して、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of condensing agent used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (3-27), but is preferably 1 equivalent or more and 10 equivalents or less.
　本反応は、縮合剤と共に添加剤を用いることが出来る。添加剤として、１－ヒドロキシベンゾトリアゾール、１－ヒドロキシ－７－アザベンゾトリアゾール、Ｎ－ヒドロキシスクシンイミド、炭酸Ｎ，Ｎ’―ジスクシンイミジル、ジメチルアミノピリジン等が挙げられる。 In this reaction, additives can be used together with the condensing agent. Examples of additives include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide, N,N'-disuccinimidyl carbonate, and dimethylaminopyridine.
本反応に使用する添加剤の量は、式（３－２７）で表される化合物に対して、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、０．１当量以上１０当量以下である。 The amount of additive used in this reaction is not particularly limited as long as the desired reaction proceeds with the compound represented by formula (3-27), but is preferably 0.1 equivalents or more and 10 equivalents or less.
　本反応に使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、１，４－ジアザビシクロ［２．２．２］オクタン等の有機塩基類、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される Examples of bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
　本反応に使用する塩基は、式（３－２７）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上３０当量以下である。 The amount of base used in this reaction is not particularly limited as long as the desired reaction proceeds in an amount of at least 1 equivalent relative to the compound represented by formula (3-27), but is preferably 1 equivalent or more and 30 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、ピリジン、２，６－ルチジン等の有機塩基系溶媒が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.; ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc.; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc.; urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc.; halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc.; and organic base solvents such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 2,6-lutidine, etc. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－２７）で表される化合物に対して１重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 1 to 200 times by weight relative to the compound represented by formula (3-27).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、濾過操作を行うことにより、不溶物を除去することも可能であるが必須ではない。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, it is possible to arbitrarily use an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary. In addition, these solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield. In addition, it is possible to remove insoluble matter by performing a filtration operation, but this is not essential.
　前記で得られた式（１－ａ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ａ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ａ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-a) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｘ］
Figure JPOXMLDOC01-appb-C000084
 [Manufacturing method X]
Figure JPOXMLDOC01-appb-C000084
　式中、Ｇは、Ｃ－Ｒ６または窒素原子を表し、Ｒ６は、水素原子、シアノ基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒｆは、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルコキシ基、Ｃ２～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し、Ｌｖ３は、ハロゲン原子、または酸無水物等の脱離基を表し、Ｒ２、Ｒ５、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＲｂは、前記と同義である。 In the formula, G represents C-R6 or a nitrogen atom, R6 represents a hydrogen atom, a cyano group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, or a C2-C6 haloalkynyl group, Rf represents a hydrogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkoxy group which may be optionally substituted with a substituent A, a C2-C6 haloalkoxy group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, A chloroalkoxy group, a C2-C6 alkenyl group which may be appropriately substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be appropriately substituted with a substituent A, a C2-C6 haloalkynyl group, Rx1Rx2NC(=O)-(wherein Rx1 and Rx2 are as defined above), Rx3C(=O)-(wherein Rx3 is as defined above), Rx3OC(=O)-(wherein Rx3 is as defined above), or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group [the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are 2 or more substituted substituents B, the substituents B may each represent independent substituents or may be the same to form a 3- to 6-membered ring). ], Lv3 represents a leaving group such as a halogen atom or an acid anhydride, and R2, R5, R7, R8, R9, R10, and Rb are the same as defined above.
　製造方法Ｘは、本発明化合物を含む式（１－ｂ）で表される化合物を得る方法であって、式（１－ａ）で表される化合物とＲｆ－Ｃ（＝Ｏ）－Ｌｖ３を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method X is a method for obtaining a compound represented by formula (1-b), which includes the compound of the present invention, and includes reacting a compound represented by formula (1-a) with Rf-C(=O)-Lv3 in a solvent in the presence of a base.
　本反応に使用するＲｆ－Ｃ（＝Ｏ）－Ｌｖ３は、市販品として入手または公知の方法で製造することができる。「Ｒｆ－Ｃ（＝Ｏ）－」が、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）である化合物を使用する場合、Ｒｆ－Ｃ（＝Ｏ）－Ｌｖ３は酸無水物を使用してもよい。 The Rf-C(=O)-Lv3 used in this reaction can be obtained commercially or produced by a known method. When using a compound in which "Rf-C(=O)-" is Rx3C(=O)- (where Rx3 has the same meaning as above) or Rx3OC(=O)- (where Rx3 has the same meaning as above), Rf-C(=O)-Lv3 may be an acid anhydride.
　本反応に使用するＲｆ－Ｃ（＝Ｏ）－Ｌｖ３の量は、式（１－ａ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of Rf-C(=O)-Lv3 used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-a), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、１，４－ジアザビシクロ［２．２．２］オクタン、ジメチルアミノピリジン等の有機塩基類、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される。 Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[2.2.2]octane, and dimethylaminopyridine; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
　本反応に使用する塩基の量は、式（１－ａ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-a), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-a).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸，塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
　前記で得られた式（１－ｂ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｂ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-b) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｂ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-b) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法Ｙ］
Figure JPOXMLDOC01-appb-C000085
 [Manufacturing method Y]
Figure JPOXMLDOC01-appb-C000085
　式中、Ｒ３は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し、Ｒ４は、水素原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し、Ｒ２、Ｒ５ａ、Ｇ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、ｒ、およびＯｘは、前記と同義である。 In the formula, R3 is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, Rx1Rx2NC(=O)- (where Rx1 and and Rx2 are as defined above.) Rx3C(=O)- (wherein Rx3 is as defined above), or Rx3OC(=O)- (wherein Rx3 is as defined above), R4 is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 aryl ... a C3 to C8 cycloalkoxy group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above), Rx3C(=O)- (wherein Rx3 is as defined above) .), Rx3OC(=O)- (wherein Rx3 has the same meaning as above), or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group [the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring, is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent, or may be the same to form a 3- to 6-membered ring.)], and R2, R5a, G, R6, R7, R8, R9, R10, r, and Ox have the same meaning as above.
　製造方法Ｙは、式（１－ｄ）で表される化合物を得る方法であって、式（１－ｃ）で表される化合物と酸化剤（Ｏｘ）とを、溶媒中で反応させることを含む製造方法である。 　Production method Y is a method for obtaining a compound represented by formula (1-d), and includes reacting a compound represented by formula (1-c) with an oxidizing agent (Ox) in a solvent.
　製造方法Ｆにおける式（３－６）で表される化合物を式（１－ｃ）で表される化合物に代えて使用することにより、製造方法Ｆに準じて製造方法Ｙを実施することができる。 By using the compound represented by formula (3-6) in place of the compound represented by formula (1-c) in production method F, production method Y can be carried out in accordance with production method F.
［製造方法Ｚ］
Figure JPOXMLDOC01-appb-C000086
 [Manufacturing method Z]
Figure JPOXMLDOC01-appb-C000086
　式中、Ｒ１、Ｒ５、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＲｂは、前記と同義である。 In the formula, R1, R5, R7, R8, R9, R10, and Rb are as defined above.
　製造方法Ｚは、式（１－ｅ）で表される本発明化合物を得る製造方法であって、式（４－２）で表される化合物と式（３－２８）で表される化合物を、溶媒中で反応させることを含む製造方法である。 　Production method Z is a production method for obtaining the compound of the present invention represented by formula (1-e), which includes reacting a compound represented by formula (4-2) with a compound represented by formula (3-28) in a solvent.
　本反応は、式（３－２８）で表されるピラゾールカルボン酸をカルボン酸ハロゲン化物へと変換した後に式（４－２）で表される化合物と塩基存在下で反応させることが出来る。また、式（３－２８）で表されるピラゾールカルボン酸と式（４－２）で表される化合物とを縮合剤を用いて、塩基存在下で反応させることが出来る。 In this reaction, the pyrazole carboxylic acid represented by formula (3-28) can be converted into an carboxylic acid halide and then reacted with a compound represented by formula (4-2) in the presence of a base. In addition, the pyrazole carboxylic acid represented by formula (3-28) can be reacted with a compound represented by formula (4-2) in the presence of a base using a condensing agent.
　製造方法Ｗにおける式（３－２７）で表される化合物を式（３－２８）で表される化合物に代えて使用することにより、製造方法Ｗに準じて製造方法Ｚを実施することができる。 By replacing the compound represented by formula (3-27) in manufacturing method W with the compound represented by formula (3-28), manufacturing method Z can be carried out in accordance with manufacturing method W.
［製造方法ＡＡ］
Figure JPOXMLDOC01-appb-C000087
 [Manufacturing method AA]
Figure JPOXMLDOC01-appb-C000087
　式中、Ｇ、Ｒ１、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｒｂ、Ｒｆ、およびＬｖ３は、前記と同義である。 In the formula, G, R1, R5, R6, R7, R8, R9, R10, Rb, Rf, and Lv3 are as defined above.
　製造方法ＡＡは、本発明化合物を含む式（１－ｆ）で表される化合物を得る方法であって、式（１－ｅ）で表される化合物とＲｆ－Ｃ（＝Ｏ）－Ｌｖ３を、溶媒中で反応させることを含む製造方法である。
　製造方法Ｘにおける式（１－ａ）で表される化合物を式（１－ｅ）で表される化合物に代えて使用することにより、製造方法Ｘに準じて製造方法ＡＡを実施することができる。 Production method AA is a method for obtaining a compound represented by formula (1-f), including the compound of the present invention, and includes reacting a compound represented by formula (1-e) with Rf-C(═O)-Lv3 in a solvent.
Production method AA can be carried out in accordance with production method X by using the compound represented by formula (1-a) in place of the compound represented by formula (1-e).
［製造方法ＡＢ］
Figure JPOXMLDOC01-appb-C000088
 [Manufacturing method AB]
Figure JPOXMLDOC01-appb-C000088
　式中、Ｇ、Ｒ１、Ｒ３、Ｒ４、Ｒ５a、Ｒ６、Ｒ８、Ｒ９、Ｒ１０、ｒ、およびＯｘは、前記と同義である。 In the formula, G, R1, R3, R4, R5a, R6, R8, R9, R10, r, and Ox are as defined above.
　製造方法ＡＢは、式（１－ｈ）で表される化合物を得る方法であって、式（１－ｇ）で表される化合物と酸化剤（Ｏｘ）とを、溶媒中で反応させることを含む製造方法である。 　Production method AB is a method for obtaining a compound represented by formula (1-h), and includes reacting a compound represented by formula (1-g) with an oxidizing agent (Ox) in a solvent.
　製造方法Ｆにおける式（３－６）で表される化合物を式（１－ｇ）で表される化合物に代えて使用することにより、製造方法Ｆに準じて製造方法ＡＢを実施することができる。 By using the compound represented by formula (3-6) in place of the compound represented by formula (1-g) in manufacturing method F, manufacturing method AB can be carried out in accordance with manufacturing method F.
［製造方法ＡＣ］
Figure JPOXMLDOC01-appb-C000089
 [Production method AC]
Figure JPOXMLDOC01-appb-C000089
　式中、Ｒ２ａは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）、または１～２個の酸素原子を含む３～６員環の基を表し、Ｇ、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＬｖは、前記と同義である。 In the formula, R2a is a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5 to 6 alkyl group which may be optionally substituted with 0 to 4 substituents B, Represents a 6-membered aromatic heterocyclic group, Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above), Rx3C(=O)- (wherein Rx3 is as defined above), Rx3OC(=O)- (wherein Rx3 is as defined above), Rx4S(O)p- (wherein Rx4 and p are as defined above), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, and G, R3, R4, R5, R6, R7, R8, R9, R10, and Lv are as defined above.
　製造方法ＡＣは、式（１－ｊ）で表される化合物を得る方法であって、式（１－ｉ）で表される化合物とＲ２ａ－Ｌｖとを、塩基存在下、溶媒中で反応させることを含む製造方法である。 　Production method AC is a method for obtaining a compound represented by formula (1-j), and includes reacting a compound represented by formula (1-i) with R2a-Lv in a solvent in the presence of a base.
　式（１－ｉ）で表される化合物は、式（１－ｋ）
Figure JPOXMLDOC01-appb-C000090
（式中、Ｇ、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９、およびＲ１０は前記と同義である。）で表される互変異性体を含む。 The compound represented by formula (1-i) is represented by formula (1-k)
Figure JPOXMLDOC01-appb-C000090
(In the formula, G, R3, R4, R5, R6, R7, R8, R9, and R10 are as defined above.)
　式（１－ｉ）で表される化合物は、式（１－ｋ）で表される化合物と同様に取り扱うことが可能であり、製造方法ＡＣを適用することができる。式（１－ｉ）で表される化合物と式（１－ｋ）で表される化合物との混合物でもよく、その異性体混合比は、単独でも任意の割合の混合物でもよい。 The compound represented by formula (1-i) can be handled in the same manner as the compound represented by formula (1-k), and manufacturing method AC can be applied to it. It may be a mixture of the compound represented by formula (1-i) and the compound represented by formula (1-k), and the isomer mixture ratio may be a single isomer or a mixture of any ratio.
　本反応に使用するＲ２ａ－Ｌｖは、市販品として入手または公知の方法で製造することができる。 The R2a-Lv used in this reaction can be obtained commercially or produced by known methods.
　本反応に使用するＲ２ａ－Ｌｖの量は、式（１－ｉ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of R2a-Lv used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-i), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、１，４－ジアザビシクロ［２．２．２］オクタン等の有機塩基類、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される。 Examples of bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
　本反応に使用する塩基の量は、式（１－ｉ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-i), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｉ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-i).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸，塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（１－ｊ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-j) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｊ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-j) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｊ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-j) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法ＡＤ］
Figure JPOXMLDOC01-appb-C000091
 [Manufacturing method AD]
Figure JPOXMLDOC01-appb-C000091
　式中、Ｒ１ａは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）、または１～２個の酸素原子を含む３～６員環の基を表し、Ｒ３、Ｒ４、Ｒ５、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＬｖは、前記と同義である。 In the formula, R1a is a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, or a C2 to C6 phenyl group which may be optionally substituted with 0 to 4 substituents B. Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above), Rx3C(=O)- (wherein Rx3 is as defined above), Rx3OC(=O)- (wherein Rx3 is as defined above), Rx4S(O)p- (wherein Rx4 and p are as defined above), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, and R3, R4, R5, R7, R8, R9, R10, and Lv are as defined above.
　製造方法ＡＤは、式（１－Ｌ）で表される化合物を得る方法であって、式（１－ｋ）で表される化合物とＲ１ａ－Ｌｖとを、塩基存在下、溶媒中で反応させることを含む製造方法である。 　Production method AD is a method for obtaining a compound represented by formula (1-L), which includes reacting a compound represented by formula (1-k) with R1a-Lv in a solvent in the presence of a base.
　製造方法ＡＣにおける式（１－ｉ）で表される化合物を式（１－ｋ）で表される化合物に、Ｒ２ａ－ＬｖをＲ１ａ－Ｌｖに代えて使用することにより、製造方法ＡＣに準じて製造方法ＡＤを実施することができる。 By substituting the compound represented by formula (1-i) in manufacturing method AC with the compound represented by formula (1-k) and substituting R2a-Lv for R1a-Lv, manufacturing method AD can be carried out in accordance with manufacturing method AC.
［製造方法ＡＥ］
Figure JPOXMLDOC01-appb-C000092
 [Manufacturing method AE]
Figure JPOXMLDOC01-appb-C000092
　式中、Ｒ２、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｒｃ、Ｒｄ、およびＲｅは、前記と同義である。 In the formula, R2, R6, R7, R8, R9, R10, Rc, Rd, and Re are as defined above.
　製造方法ＡＥは、式（１－ｍ）で表される化合物を得る方法であって、式（４－１）で表される化合物と式（３－１９）で表される化合物を、溶媒中で反応させることを含む製造方法である。 　Production method AE is a method for obtaining a compound represented by formula (1-m), which includes reacting a compound represented by formula (4-1) with a compound represented by formula (3-19) in a solvent.
　本反応は、塩基を使用することが出来る。使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、１，４－ジアザビシクロ［２．２．２］オクタン等の有機塩基類、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される。 A base can be used in this reaction. Examples of bases that can be used include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, and 1,4-diazabicyclo[2.2.2]octane; metal hydrides such as sodium hydride; organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, and hexyllithium; and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
　本反応に使用する塩基の量は、式（３－１９）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of base used in this reaction may be at least 1 equivalent relative to the compound represented by formula (3-19), and is not particularly limited as long as the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 10 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, etc., urea solvents such as 1,3-dimethyl-2-imidazolidinone, etc., halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３－１９）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (3-19).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸，塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation can be performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（１－ｍ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-m) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｍ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-m) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｍ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-m) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法ＡＦ］
Figure JPOXMLDOC01-appb-C000093
 [Manufacturing method AF]
Figure JPOXMLDOC01-appb-C000093
　式中、Ｒ２、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｑ、Ｒｃ、およびＲｄは、前記と同義である。 In the formula, R2, R5a, R6, R7, R8, R9, R10, Q, Rc, and Rd are as defined above.
　製造方法ＡＦは、式（１－ｎ）で表される化合物の合成法であって、式（１－ｍ）で表される化合物とＲ５ａ－ＱＨ（ここで、Ｒ５ａは前記と同義である。）を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method AF is a method for synthesizing a compound represented by formula (1-n), which includes reacting a compound represented by formula (1-m) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
　製造方法Ｐにおける式（３－１８）で表される化合物を式（１－ｍ）で表される化合物に代えて使用することにより、製造方法Ｐに準じて製造方法ＡＦを実施することができる。 By using the compound represented by formula (3-18) in place of the compound represented by formula (1-m) in manufacturing method P, manufacturing method AF can be carried out in accordance with manufacturing method P.
［製造方法ＡＧ］
Figure JPOXMLDOC01-appb-C000094
　式中、Ｒ２、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｑ、およびＲｄは、前記と同義である。 [Manufacturing method AG]
Figure JPOXMLDOC01-appb-C000094
In the formula, R2, R5a, R6, R7, R8, R9, R10, Q, and Rd are as defined above.
　製造方法ＡＧは、本発明化合物の製造中間体である式（１－ｏ）で表される化合物の合成方法であって、式（１－ｎ）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 　Production method AG is a method for synthesizing a compound represented by formula (1-o), which is a production intermediate for the compound of the present invention, and includes reacting a compound represented by formula (1-n) in a solvent under acidic or basic conditions.
　まず、酸性条件の反応について説明する。 First, let's explain the reaction under acidic conditions.
　本反応に使用する酸は、塩酸、臭化水素酸、リン酸等の無機酸類や、酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等の有機酸類が例示される。目的とする反応が進行する限り特に制限されることはない。 The acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, etc., or organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, etc. There are no particular limitations as long as the desired reaction proceeds.
　本反応に使用する酸の量は、触媒量でもよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、式（１－ｎ）で表される化合物に対して０．０１当量以上である。また、液体状の酸に関しては溶媒として使用することも可能である。 The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more relative to the compound represented by formula (1-n). In addition, liquid acids can also be used as a solvent.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、酢酸、メタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 　The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, acidic solvents such as acetic acid and methanesulfonic acid, ether solvents such as diethyl ether, 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, and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｎ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-n).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 180°C or below the boiling point of the solvent.
　次に、塩基性条件の反応について説明する。 Next, we will explain the reaction under basic conditions.
　本反応に使用する塩基は、水酸化リチウム、水酸化ナトリウム、水酸化カリウム等の無機塩基類が例示されるが、目的とする反応が進行する限りにおいて特に限定されることはない。 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 desired reaction proceeds.
　本反応に使用する塩基は、式（１－ｎ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上３０当量以下である。 The amount of base used in this reaction is not particularly limited as long as it is at least 1 equivalent relative to the compound represented by formula (1-n) and the desired reaction proceeds, but is preferably at least 1 equivalent and no more than 30 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include water, ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and the like, alcohol solvents such as methanol, ethanol, isopropanol, and the like, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, and the like, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and the like. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｎ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-n).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
　反応の後処理は、酸性条件での反応と塩基性条件の反応は共通の方法で行える。反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　Reactions under acidic and basic conditions can be treated by the same method after the reaction. A separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using 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, or saline solution can be used as desired. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene, an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate, an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether, a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary. These solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
　前記で得られた式（１－ｏ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-o) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｏ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-o) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｏ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-o) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法ＡＨ］
Figure JPOXMLDOC01-appb-C000095
　式中、Ｒ２、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＱは前記と同義である。 [Manufacturing method AH]
Figure JPOXMLDOC01-appb-C000095
In the formula, R2, R5a, R6, R7, R8, R9, R10, and Q are defined as above.
　製造方法ＡＨは、式（１－ｐ）で表される化合物を得る方法であって、式（１－ｏ）で表される化合物とアジド化合物とを、ｔ－ブタノール存在下、溶媒中で反応させることを含む製造方法である。 　Production method AH is a method for obtaining a compound represented by formula (1-p), which includes reacting a compound represented by formula (1-o) with an azide compound in a solvent in the presence of t-butanol.
　本反応に使用するアジド化合物はジフェニルリン酸アジド等が挙げられる。 Azide compounds used in this reaction include diphenylphosphoryl azide, etc.
　本反応に使用するアジド化合物の量は、式（１－ｏ）で表される化合物に対して、１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、通常、１当量以上１０当量以下である。 The amount of the azide compound used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-o), and is not particularly limited as long as the desired reaction proceeds, but is usually at least 1 equivalent and no more than 10 equivalents.
　本反応に使用するｔ－ブタノールの量は、式（１－ｏ）で表される化合物に対して、１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはない。ｔ－ブタノール自体を溶媒として使用することもできる。 The amount of t-butanol used in this reaction is not particularly limited as long as it is at least one equivalent relative to the compound represented by formula (1-o), and the desired reaction proceeds. t-butanol itself can also be used as the solvent.
　本反応に使用する溶媒は、ｔ－ブタノール等のアルコール系溶媒、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 Solvents used in this reaction include alcohol solvents such as t-butanol, ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｏ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-o).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の、水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of separations, and they can be performed according to the desired purity and yield.
　前記で得られた式（１－ｐ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-p) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｐ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-p) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｐ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-p) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法ＡＩ］
Figure JPOXMLDOC01-appb-C000096
　式中、Ｇ、Ｑ、Ｒ２、Ｒ５a、Ｒ６、Ｒ７、Ｒ８、Ｒ９、およびＲ１０は前記と同義である。 [Manufacturing Method AI]
Figure JPOXMLDOC01-appb-C000096
In the formula, G, Q, R2, R5a, R6, R7, R8, R9, and R10 are defined as above.
　製造方法ＡＩは、式（１－ｒ）で表される化合物を得る方法であって、式（１－ｑ）で表される化合物と酸とを溶媒中で反応させることを含む製造方法である。 　Production method AI is a method for obtaining a compound represented by formula (1-r), and includes reacting a compound represented by formula (1-q) with an acid in a solvent.
　本反応に使用する酸は、塩酸、臭化水素酸等の無機酸類や、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等の有機酸類が例示される。目的とする反応が進行する限り特に制限されることはない。 The acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid or hydrobromic acid, or organic acids such as methanesulfonic acid, p-toluenesulfonic acid, or trifluoroacetic acid. There are no particular limitations as long as the desired reaction proceeds.
　本反応に使用する酸の量としては、式（１－ｑ）で表される化合物に対して触媒量あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、通常は、１当量以上であり、溶媒として使用することもできる。 The amount of acid used in this reaction is not particularly limited as long as it is a catalytic amount relative to the compound represented by formula (1-q) and the desired reaction proceeds, but is usually at least one equivalent, and can also be used as a solvent.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、塩酸、トリフルオロ酢酸等の酸溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acid solvents such as hydrochloric acid and trifluoroacetic acid, ether solvents such as diethyl ether, 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, and butyl acetate, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｑ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-q).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の、水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, as necessary. These solvents can be used alone or in a mixture of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（１－ｒ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-r) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｒ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-r) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｒ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-r) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
　式（１－ｒ）で表される化合物は、本発明化合物である式（１－２）で表される化合物を得るための有用な中間体となりうる。 The compound represented by formula (1-r) can be a useful intermediate for obtaining the compound represented by formula (1-2), which is the compound of the present invention.
　式（１－ｒ）で表される製造中間体の具体例は、表６に示す構造式Ｅ－１～Ｅ－２４（ここで、表６中のＲ２、およびＨｅｔは、前記と同義である。）を表す。これらの化合物は、例示のためのものであって、これらに限定されるものではない。 Specific examples of the intermediates represented by formula (1-r) are represented by the structural formulas E-1 to E-24 shown in Table 6 (where R2 and Het in Table 6 have the same meanings as above). These compounds are given for illustrative purposes only and are not intended to be limiting.
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000097
［製造方法ＡＪ］
Figure JPOXMLDOC01-appb-C000098
　式中、Ｇ、Ｒ２、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｑ、ＲｆおよびＬｖ３は前記と同義である。 [Manufacturing method AJ]
Figure JPOXMLDOC01-appb-C000098
In the formula, G, R2, R5a, R6, R7, R8, R9, R10, Q, Rf and Lv3 are defined as above.
　製造方法ＡＪは、式（１－ｓ）で表される化合物を得る方法であって、式（１－ｒ）で表される化合物と、Ｒｆ－Ｃ（＝Ｏ）－Ｌｖ３で表される化合物を、溶媒中で反応させることを含む製造方法である。 　Production method AJ is a method for obtaining a compound represented by formula (1-s), which includes reacting a compound represented by formula (1-r) with a compound represented by Rf-C(=O)-Lv3 in a solvent.
　製造方法Ｘにおける式（１－ａ）で表される化合物を式（１－ｒ）で表される化合物に代えて使用することにより、製造方法Ｘに準じて製造方法ＡＪを実施することができる。 By using the compound represented by formula (1-a) in place of the compound represented by formula (1-r) in manufacturing method X, manufacturing method AJ can be carried out in accordance with manufacturing method X.
［製造方法ＡＫ］
Figure JPOXMLDOC01-appb-C000099
 [Manufacturing method AK]
Figure JPOXMLDOC01-appb-C000099
　式中、Ｒ１、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｒｃ、Ｒｄ、およびＲｅは、前記と同義である。 In the formula, R1, R6, R7, R8, R9, R10, Rc, Rd, and Re are as defined above.
　製造方法ＡＫは、式（１－ｔ）で表される化合物を得る方法であって、式（４－１）で表される化合物と式（３－２４）で表される化合物を、溶媒中で反応させることを含む製造方法である。 　Production method AK is a method for obtaining a compound represented by formula (1-t), and includes reacting a compound represented by formula (4-1) with a compound represented by formula (3-24) in a solvent.
　製造方法ＡＥにおける式（３－１９）で表される化合物を式（３－２４）で表される化合物に代えて使用することにより、製造方法ＡＥに準じて製造方法ＡＫを実施することができる。 By replacing the compound represented by formula (3-19) in manufacturing method AE with the compound represented by formula (3-24), manufacturing method AK can be carried out in accordance with manufacturing method AE.
［製造方法ＡＬ］
Figure JPOXMLDOC01-appb-C000100
 [Manufacturing method AL]
Figure JPOXMLDOC01-appb-C000100
　式中、Ｒ１、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｑ、Ｒｃ、およびＲｄは、前記と同義である。 In the formula, R1, R5a, R6, R7, R8, R9, R10, Q, Rc, and Rd are as defined above.
　製造方法ＡＬは、式（１－ｕ）で表される化合物の合成法であって、式（１－ｔ）で表される化合物とＲ５ａ－ＱＨ（ここで、Ｒ５ａは前記と同義である。）を、塩基の存在下、溶媒中で反応させることを含む製造方法である。 　Production method AL is a method for synthesizing a compound represented by formula (1-u), which includes reacting a compound represented by formula (1-t) with R5a-QH (wherein R5a has the same meaning as above) in a solvent in the presence of a base.
　製造方法ＡＦにおける式（１－ｍ）で表される化合物を式（１－ｔ）で表される化合物に代えて使用することにより、製造方法ＡＦに準じて製造方法ＡＬを実施することができる。 By using the compound represented by formula (1-m) in place of the compound represented by formula (1-t) in manufacturing method AF, manufacturing method AL can be carried out in accordance with manufacturing method AF.
［製造方法ＡＭ］
Figure JPOXMLDOC01-appb-C000101
　式中、Ｒ１、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｑ、およびＲｄは、前記と同義である。 [Manufacturing method AM]
Figure JPOXMLDOC01-appb-C000101
In the formula, R1, R5a, R6, R7, R8, R9, R10, Q, and Rd are as defined above.
　製造方法ＡＭは、式（１－ｖ）で表される化合物の合成方法であって、式（１－ｕ）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 　Production method AM is a method for synthesizing a compound represented by formula (1-v), which includes reacting a compound represented by formula (1-u) in a solvent under acidic or basic conditions.
　製造方法ＡＧにおける式（１－ｎ）で表される化合物を式（１－ｕ）で表される化合物に代えて使用することにより、製造方法ＡＧに準じて製造方法ＡＭを実施することができる。 By using the compound represented by formula (1-n) in place of the compound represented by formula (1-u) in manufacturing method AG, manufacturing method AM can be carried out in accordance with manufacturing method AG.
［製造方法ＡＮ］
Figure JPOXMLDOC01-appb-C000102
　式中、Ｒ１、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＱは前記と同義である。 [Manufacturing method AN]
Figure JPOXMLDOC01-appb-C000102
In the formula, R1, R5a, R6, R7, R8, R9, R10, and Q are defined as above.
　製造方法ＡＮは、式（１－ｗ）で表される化合物を得る方法であって、式（１－ｖ）で表される化合物とアジド化合物とを、ｔ－ブタノール存在下、溶媒中で反応させることを含む製造方法である。 　Production method AN is a method for obtaining a compound represented by formula (1-w), which includes reacting a compound represented by formula (1-v) with an azide compound in a solvent in the presence of t-butanol.
　本反応に使用するアジド化合物は、ジフェニルリン酸アジド等が挙げられる。 Azide compounds used in this reaction include diphenylphosphoryl azide, etc.
　本反応に使用するアジド化合物の量は、式（１－ｖ）で表される化合物に対して、１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、通常、１当量以上１０当量以下である。 The amount of the azide compound used in this reaction may be at least 1 equivalent relative to the compound represented by formula (1-v), and is not particularly limited as long as the desired reaction proceeds, but is usually at least 1 equivalent and no more than 10 equivalents.
　本反応に使用するｔ－ブタノールの量は、式（１－ｖ）で表される化合物に対して、１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはない。ターシャリブタノール自体を溶媒として使用することもできる。 The amount of t-butanol used in this reaction is not particularly limited as long as it is at least one equivalent relative to the compound represented by formula (1-v), and the desired reaction proceeds. Tertiary butanol itself can also be used as a solvent.
　本反応に使用する溶媒は、ｔ－ブタノール等のアルコール系溶媒、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 Solvents used in this reaction include alcohol solvents such as t-butanol, ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in combination of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｖ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-v).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between 0°C and 150°C or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の、水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, or chloroform; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in any ratio of two or more. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（１－ｗ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-w) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｗ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-w) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｗ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-w) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
［製造方法ＡＯ］
Figure JPOXMLDOC01-appb-C000103
　式中、Ｒ１、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、およびＱは前記と同義である。 [Manufacturing method AO]
Figure JPOXMLDOC01-appb-C000103
In the formula, R1, R5a, R6, R7, R8, R9, R10, and Q are defined as above.
　製造方法ＡＯは、式（１－ｙ）で表される化合物を得る方法であって、式（１－ｘ）で表される化合物と酸とを溶媒中で反応させることを含む製造方法である。 　Production method AO is a method for obtaining a compound represented by formula (1-y), which includes reacting a compound represented by formula (1-x) with an acid in a solvent.
　本反応に使用する酸は、塩酸、臭化水素酸等の無機酸類や、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等の有機酸類が例示される。目的とする反応が進行する限り特に制限されることはない。 The acid used in this reaction can be, for example, inorganic acids such as hydrochloric acid or hydrobromic acid, or organic acids such as methanesulfonic acid, p-toluenesulfonic acid, or trifluoroacetic acid. There are no particular limitations as long as the desired reaction proceeds.
　本反応に使用する酸の量としては、式（１－ｘ）で表される化合物に対して触媒量あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、通常は、１当量以上であり、溶媒として使用することもできる。 The amount of acid used in this reaction is not particularly limited as long as it is a catalytic amount relative to the compound represented by formula (1-x) and the desired reaction proceeds, but is usually at least one equivalent, and can also be used as a solvent.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、塩酸、トリフルオロ酢酸等の酸溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but examples include acid solvents such as hydrochloric acid and trifluoroacetic acid, ether solvents such as diethyl ether, 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, and butyl acetate, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｘ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight relative to the compound represented by formula (1-x).
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１８０℃以下または溶媒の沸点以下である。 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C, or below the boiling point of the solvent.
　反応の後処理としては、反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の、水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 　As a post-treatment of the reaction, it is possible to perform a separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved; an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved; an aqueous solution in which a salt containing a sulfur atom, such as sodium thiosulfate or sodium sulfite, is dissolved; or a saline solution. During the separation operation, it is possible to add a solvent that is not compatible with water, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl-t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane, if necessary. These solvents can be used alone or in any combination of two or more types in any ratio. There is no particular limit to the number of times separation is performed, and it can be performed according to the desired purity and yield.
　前記で得られた式（１－ｙ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 The reaction mixture containing the compound represented by formula (1-y) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
　前記で得られた式（１－ｙ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by formula (1-y) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
　溶媒留去後に得られた式（１－ｙ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 The reaction mixture containing the compound represented by formula (1-y) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc. The method may be appropriately set depending on the desired purity.
　式（１－ｙ）で表される化合物は、本発明化合物である式（１－１）で表される化合物を得るための有用な中間体となりうる。 The compound represented by formula (1-y) can be a useful intermediate for obtaining the compound represented by formula (1-1), which is the compound of the present invention.
　式（１－ｙ）で表される製造中間体の具体例は、表７に示す構造式Ｄ－１～Ｄ－２４（ここで、表７中のＲ１、およびＨｅｔは、前記と同義である。）を表す。これらの化合物は、例示のためのものであって、これらに限定されるものではない。 Specific examples of the manufacturing intermediate represented by formula (1-y) are represented by structural formulas D-1 to D-24 shown in Table 7 (where R1 and Het in Table 7 have the same meanings as above). These compounds are given for illustrative purposes only and are not intended to be limiting.
Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000104
［製造方法ＡＰ］
Figure JPOXMLDOC01-appb-C000105
　式中、Ｇ、Ｒ１、Ｒ５ａ、Ｒ６、Ｒ７、Ｒ８、Ｒ９、Ｒ１０、Ｑ、ＲｆおよびＬｖ３は前記と同義であるは前記と同義である。 [Manufacturing Method AP]
Figure JPOXMLDOC01-appb-C000105
In the formula, G, R1, R5a, R6, R7, R8, R9, R10, Q, Rf and Lv3 are as defined above.
　製造方法ＡＰは、式（１－ｚ）で表される化合物を得る方法であって、式（１－ｙ）で表される化合物と、Ｒｆ－Ｃ（＝Ｏ）－Ｌｖ３で表される化合物を、溶媒中で反応させることを含む製造方法である。 　Production method AP is a method for obtaining a compound represented by formula (1-z), which includes reacting a compound represented by formula (1-y) with a compound represented by Rf-C(=O)-Lv3 in a solvent.
　製造方法ＡＡにおける式（１－ｅ）で表される化合物を式（１－ｙ）で表される化合物に代えて使用することにより、製造方法ＡＡに準じて製造方法ＡＰを実施することができる。 By using the compound represented by formula (1-e) in place of the compound represented by formula (1-y) in manufacturing method AA, manufacturing method AP can be carried out in accordance with manufacturing method AA.
　以上に示した、製造方法Ａ～製造方法ＡＰを任意に組み合わせて、式（１－１）、および式（１－２）で表される化合物を製造することができる。もしくは、公知の方法と製造方法Ａ～製造方法ＡＰを任意に組み合わせても、式（１－１）、および式（１－２）で表される化合物を製造することができる。 The compounds represented by formula (1-1) and formula (1-2) can be produced by arbitrarily combining the above-mentioned Production Method A to Production Method AP. Alternatively, the compounds represented by formula (1-1) and formula (1-2) can be produced by arbitrarily combining known methods with Production Method A to Production Method AP.
　本発明化合物は、植物又は動物（例えば、ヒト、ならびに家畜及び愛玩動物などのヒト以外の哺乳動物及び鳥類）、特に植物に対して有害な生物を防除できるために、農薬として使用することができる。具体的には、殺虫剤、殺菌剤、除草剤、植物成長調整剤等が挙げられる。好ましくは、殺虫剤である。 The compound of the present invention can be used as an agricultural chemical because it can control organisms harmful to plants or animals (e.g., humans, and non-human mammals such as livestock and pets, and birds), especially plants. Specific examples include insecticides, fungicides, herbicides, and plant growth regulators. Preferably, it is an insecticide.
　本発明化合物を含有する組成物の施用方法としては、植物体もしくは種子と接触させる方法、または、栽培土壌に含有させて、植物の根もしくは地下茎に接触させる方法が挙げられる。具体例として、組成物の植物個体への茎葉散布処理、注入処理、苗箱処理、セルトレー処理、植物種子への吹き付け処理、植物種子への塗沫処理、植物種子への浸漬処理、植物種子への粉衣処理、土壌表面への散布処理、土壌表面への散布処理後の土壌混和、土壌中への注入処理、土壌中での注入処理後の土壌混和、土壌潅注処理、土壌潅注処理後の土壌混和等が挙げられる。通常、当業者が利用するようないかなる施用方法を用いても十分な効力を発揮する。 Methods for applying the composition containing the compound of the present invention include contacting the composition with a plant body or seed, or including the composition in cultivation soil and contacting the roots or rhizomes of the plant. Specific examples include foliage spraying of the composition onto individual plants, injection, seedling box treatment, cell tray treatment, spraying onto plant seeds, smearing onto plant seeds, soaking into plant seeds, dressing onto plant seeds, spraying onto the soil surface, soil incorporation after spraying onto the soil surface, injection into soil, soil incorporation after injection into soil, soil drenching, soil incorporation after soil drenching, etc. Generally, any application method used by those skilled in the art will be sufficiently effective.
　本発明でいう「植物」とは、光合成をして運動せずに生活するものをいう。具体例として、稲、小麦、大麦、トウモロコシ、コーヒー、バナナ、ブドウ、リンゴ、ナシ、モモ、オウトウ、カキ、カンキツ、大豆、インゲン、ワタ、イチゴ、ジャガイモ、キャベツ、レタス、トマト、キュウリ、ナス、スイカ、テンサイ、ホウレンソウ、サヤエンドウ、カボチャ、サトウキビ、タバコ、ピーマン、サツマイモ、サトイモ、コンニャク、綿、ヒマワリ、バラ、チューリップ、キク、芝等およびそれらのＦ１品種等が挙げられる。また、遺伝子等を人工的に操作することにより生み出され、元来自然界に存在するものではない遺伝子組み換え作物も含み、例えば、除草剤耐性を付与した大豆、トウモロコシ、綿等、寒冷地適応したイネ、タバコ等、殺虫物質生産能を付与したトウモロコシ、綿等の農園芸作物等が挙げられる。さらに、マツ、トネリコ、イチョウ、カエデ、カシ、ポプラ、ケヤキ等の樹木等が挙げられる。また、本発明でいう「植物体」とは、前記の植物個体を構成する全ての部位を総称するものであり、例えば、茎、葉、根、種子、花、果実等が挙げられる。 In the present invention, "plants" refers to things that live without moving and use photosynthesis. Specific examples include rice, wheat, barley, corn, coffee, bananas, grapes, apples, pears, peaches, cherries, persimmons, citrus, soybeans, beans, cotton, strawberries, potatoes, cabbage, lettuce, tomatoes, cucumbers, eggplants, watermelons, sugar beets, spinach, snow peas, pumpkins, sugarcane, tobacco, peppers, sweet potatoes, taro, konjac, cotton, sunflowers, roses, tulips, chrysanthemums, grass, and F1 varieties thereof. Also included are genetically modified crops that are produced by artificially manipulating genes and do not originally exist in nature, such as soybeans, corn, cotton, etc. that have been given herbicide resistance, rice, tobacco, etc. that have been adapted to cold regions, and agricultural and horticultural crops such as corn and cotton that have been given the ability to produce insecticides. Further examples include trees such as pine, ash, ginkgo, maple, oak, poplar, and zelkova. In addition, the term "plant body" as used in the present invention collectively refers to all parts that constitute the above-mentioned plant individual, including, for example, stems, leaves, roots, seeds, flowers, and fruits.
　本発明でいう「種子」とは、幼植物が発芽するための栄養分を蓄え、農業上繁殖に用いられるものをいう。具体例として、トウモロコシ、大豆、綿、稲、テンサイ、小麦、大麦、ヒマワリ、トマト、キュウリ、ナス、ホウレンソウ、サヤエンドウ、カボチャ、サトウキビ、タバコ、ピーマン、セイヨウアブラナ等の種子、それらのＦ１品種等の種子、サトイモ、ジャガイモ、サツマイモ、コンニャク等の種芋、食用ゆり、チューリップ等の球根、ラッキョウ等の種球、および遺伝子組み換え作物の種子ならびに塊茎等が挙げられる。 In the present invention, "seeds" refers to those that store nutrients for young plants to germinate and are used for agricultural propagation. Specific examples include seeds of corn, soybeans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, snow peas, pumpkin, sugar cane, tobacco, bell pepper, rapeseed, etc., seeds of F1 varieties of these, seed potatoes such as taro, potato, sweet potato, and konjac, bulbs such as edible lilies and tulips, seed bulbs such as scallions, and seeds and tubers of genetically modified crops.
　本発明化合物は、有害生物防除剤の有効成分として優れた効果を有するものであり、畑地、水田、茶園、果樹園、牧草地、芝生、森林、庭園、街路樹等を加害する各種農業場面において防除対象となる有害生物、特に有害節足動物に対して使用することができる。
　本発明化合物は、植物種子に適用することにより、播種後の植物に発生する農業害虫等の有害生物による被害を予防することが出来る。
　本発明化合物は、倉庫に貯蔵された穀物等を加害する貯穀害虫に対して防除効果を示す。
　本発明化合物は、建築物、家具、貯蔵木材等の木材を加害する木材食害虫等の昆虫類に対して防除効果を示す。
　本発明化合物は、家屋等の人間の生活環境で悪影響を与える衛生害虫に対して駆除効果を有する。
　本発明化合物は、哺乳動物及び鳥類の外部または内部寄生虫に対して駆除効果を有する。
　本発明化合物は、上記と同様の場面で発生、加害するダニ類、甲殻類、軟体動物、線虫類の何れの有害生物も防除できる。 The compound of the present invention has excellent effects as an active ingredient of a pest control agent, and can be used against pests, particularly harmful arthropods, that are the subject of control in various agricultural settings, such as farm fields, paddy fields, tea plantations, orchards, pastures, lawns, forests, gardens, and roadside trees.
By applying the compound of the present invention to plant seeds, damage caused by harmful organisms such as agricultural pests that appear on plants after sowing can be prevented.
The compound of the present invention exhibits a controlling effect against stored grain pests which damage grains and the like stored in warehouses.
The compound of the present invention has a controlling effect against insects such as wood-eating pests which damage wood in buildings, furniture, stored wood and the like.
The compound of the present invention has an exterminating effect against sanitary pests which adversely affect human living environments such as houses.
The compounds of the present invention have an antiparasitic effect against external and internal parasites of mammals and birds.
The compound of the present invention can control any of the pests such as mites, crustaceans, mollusks and nematodes which appear and cause damage in the same situations as those mentioned above.
　本発明化合物は、昆虫類、ダニ類、甲殻類、クモ類、およびムカデ類などの節足動物、軟体動物、ならびに線虫類等の有害生物に対して有効である。以下に、害虫名の具体例を示すがこれに限定しない。
チャトゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ　ｃａｍｅｌｌｉａｅ）、ミカントゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ　ｓｐｉｎｉｆｅｒｕｓ）、ブドウコナジラミ（Ａｌｅｕｒｏｌｏｂｕｓ　ｔａｏｎａｂａｅ）、Ａｍｒａｓｃａ　ｂｉｇｕｔｔｕｌａｂｉｇｕｔｔｕｌａ、アカマルカイガラムシ（Ａｏｎｉｄｉｅｌｌａ　ａｕｒａｎｔｉｉ）、マメクロアブラムシ（Ａｐｈｉｓ　ｆａｂａｅ）、ダイズアブラムシ（Ａｐｈｉｓｇｌｙｃｉｎｅｓ）、ワタアブラムシ（Ａｐｈｉｓ　ｇｏｓｓｙｐｉｉ）、ヨーロッパリンゴアブラムシ（Ａｐｈｉｓ　ｐｏｍｉ）、ユキヤナギアブラムシ（Ａｐｈｉｓ　ｓｐｉｒａｅｃｏｌａ）、フタテンヒメヨコバイ（Ａｒｂｏｒｉｄｉａ　ａｐｉｃａｌｉｓ）、ジャガイモヒゲナガアブラムシ（Ａｕｌａｃｏｒｔｈｕｍ　ｓｏｌａｎｉ）、ミドリナガヨコバイ（Ｂａｌｃｌｕｔｈａ　ｓａｌｔｕｅｌｌａ）、シルバーリーフコナジラミ（Ｂｅｍｉｓｉａ　ａｒｇｅｎｔｉｆｏｌｉｉ）、タバココナジラミ（Ｂｅｍｉｓｉａ　ｔａｂａｃｉ）、アメリカコバネナガカメムシ（Ｂｌｉｓｓｕｓ　ｌｅｕｃｏｐｔｅｒｕｓ）、
ムギワラギクオマルアブラムシ（Ｂｒａｃｈｙｃａｕｄｕｓ　ｈｅｌｉｃｈｒｙｓｉ）、ダイコンアブラムシ（Ｂｒｅｖｉｃｏｒｙｎｅ　ｂｒａｓｓｉｃａｅ）、チュウゴクナシキジラミ（Ｃａｃｏｐｓｙｌｌａ　ｃｈｉｎｅｎｓｉｓ）、ピアプシラ（Ｃａｃｏｐｓｙｌｌａ　ｐｙｒｉｃｏｌａ）、ナシキジラミ（Ｃａｃｏｐｓｙｌｌａ　ｐｙｒｉｓｕｇａ）、カンシャコバネナガカメムシ（Ｃａｖｅｌｅｒｉｕｓ　ｓａｃｃｈａｒｉｖｏｒｕｓ）、カンシャワタアブラムシ（Ｃｅｒａｔｏｖａｃｕｎａ　ｌａｎｉｇｅｒａ）、ツノロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｃｅｒｉｆｅｒｕｓ）、ルビーロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｒｕｂｅｎｓ）、ネッタイトコジラミ（Ｃｉｍｅｘ　ｈｅｍｉｐｔｅｒｕｓ）、トコジラミ（Ｃｉｍｅｘ　ｌｅｃｔｕｌａｒｉｕｓ）、ホソハリカメムシ（Ｃｌｅｔｕｓ　ｐｕｎｃｔｉｇｅｒ）、シロオオヨコバイ（Ｃｏｆａｎａ　ｓｐｅｃｔｒａ）、ナシマルカイガラムシ（Ｃｏｍｓｔｏｃｋａｓｐｉｓ　ｐｅｒｎｉｃｉｏｓａ）、コーンリーフホッパー（Ｄａｌｂｕｌｕｓ　ｍａｉｄｉｓ）、ミカンコナジラミ（Ｄｉａｌｅｕｒｏｄｅｓ　ｃｉｔｒｉ）、ミカンキジラミ（Ｄｉａｐｈｏｒｉｎａ　ｃｉｔｒｉ）、Ｄｉｃｈｅｌｏｐｓ　ｍｅｌａｃａｎｔｈｕｓ　、ブチヒゲカメムシ（Ｄｏｌｙｃｏｒｉｓ　ｂａｃｃａｒｕｍ）、オオワラジカイガラムシ（Ｄｒｏｓｉｃｈａ　ｃｏｒｐｕｌｅｎｔａ）、ｒｏｓｙ　ａｐｐｌｅ　ａｐｈｉｄ（Ｄｙｓａｐｈｉｓ　ｐｌａｎｔａｇｉｎｅａ）、アカホシカメムシ（Ｄｙｓｄｅｒｃｕｓ　ｃｉｎｇｕｌａｔｕｓ）、ポテトリーフホッパー（Ｅｍｐｏａｓｃａ　ｆａｂａｅ）、カキノヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｎｉｐｐｏｎｉｃａ）、チャノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｏｎｕｋｉｉ）、マメノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｓａｋａｉｉ）、フタテンオオヨコバイ（Ｅｐｉａｃａｎｔｈｕｓ　ｓｔｒａｍｉｎｅｕｓ）、リンゴワタムシ（Ｅｒｉｏｓｏｍａ　ｌａｎｉｇｅｒｕｍ）、ナガメ（Ｅｕｒｙｄｅｍａ　ｒｕｇｏｓｕｍ）、ブラウンスティンクバグ（Ｅｕｓｃｈｉｓｔｕｓ　ｈｅｒｏｓ）、トゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ａｅｎｅｕｓ）、オオトゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ｌｅｗｉｓｉ）、シラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ｖｅｎｔｒａｌｉｓ）、
ティースケール（Ｆｉｏｒｉｎｉａ　ｔｈｅａｅ）、ツヤアオカメムシ（Ｇｌａｕｃｉａｓ　ｓｕｂｐｕｎｃｔａｔｕｓ）、クロトビカスミカメ（Ｈａｌｔｉｃｕｓ　ｉｎｓｕｌａｒｉｓ）、クサギカメムシ（Ｈａｌｙｏｍｏｒｐｈａ　ｈａｌｙｓ）、モモコフキアブラムシ（Ｈｙａｌｏｐｔｅｒｕｓ　ｐｒｕｎｉ）、イセリアカイガラムシ（Ｉｃｅｒｙａ　ｐｕｒｃｈａｓｉ）、キタウンカ（Ｊａｖｅｓｅｌｌａ　ｐｅｌｌｕｃｉｄａ）、ヒメトビウンカ（Ｌａｏｄｅｌｐｈａｘ　ｓｔｒｉａｔｅｌｌａ）、ホソクモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ　ａｃｕｔａ）、クモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ　ｃｈｉｎｅｎｓｉｓ）、アシビロヘリカメムシ（Ｌｅｐｔｏｇｌｏｓｓｕｓ　ａｕｓｔｒａｌｉｓ）、ニセダイコンアブラムシ（Ｌｉｐａｐｈｉｓ　ｅｒｙｓｉｍｉ）、サビイロカスミカメ（Ｌｙｇｕｓ　ｌｉｎｅｏｌａｒｉｓ）、ターニッシュドプラントバグ（Ｌｙｇｕｓ　ｌｉｎｅｏｌａｒｉｓ）、チューリップヒゲナガアブラムシ（Ｍａｃｒｏｓｉｐｈｕｍ　ｅｕｐｈｏｒｂｉａｅ）、ヒメフタテンヨコバイ（Ｍａｃｒｏｓｔｅｌｅｓ　ｓｔｒｉｉｆｒｏｎｓ）、Ｍａｈａｎａｒｖａ　ｆｉｍｂｒｉｏｌａｔａ、Ｍａｈａｎａｒｖａ　ｐｏｓｔｉｃａｔａ、ヒエノアブラムシ（Ｍｅｌａｎａｐｈｉｓ　ｓａｃｃｈａｒｉ）、モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）、レタスヒゲナガアブラムシ（Ｎａｓｏｎｏｖｉａ　ｒｉｂｉｓｎｉｇｒｉ）、ツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｃｉｎｃｔｉｎｃｅｐｓ）、クロスジツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｎｉｇｒｏｐｉｃｔｕｓ）、タイワンツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｖｉｒｅｓｃｅｎｓ）、アオクサカメムシ（Ｎｅｚａｒａ　ａｎｔｅｎｎａｔａ）、
ミナミアオカメムシ（Ｎｅｚａｒａ　ｖｉｒｉｄｕｌａ）、トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）、Ｏｅｂａｌｕｓ　ｐｕｇｎａｘ、トウモロコシウンカ（Ｐｅｒｅｇｒｉｎｕｓ　ｍａｉｄｉｓ）、クロフツノウンカ（Ｐｅｒｋｉｎｓｉｅｌｌａ　ｓａｃｃｈａｒｉｃｉｄａ）、ナスコナカイガラムシ（Ｐｈｅｎａｃｏｃｃｕｓ　ｓｏｌａｎｉ）、クロテンコナカイガラムシ（Ｐｈｅｎａｃｏｃｃｕｓ　ｓｏｌｅｎｏｐｓｉｓ）、ピーカンフィロキセラ（Ｐｈｙｌｌｏｘｅｒａ　ｄｅｖａｓｔａｔｒｉｘ）、ピーカンリーフフィロキセラ　（Ｐｈｙｌｌｏｘｅｒａ　ｎｏｔａｂｉｌｉｓ）、サウザンピーカンリーフフィロキセラ（Ｐｈｙｌｌｏｘｅｒａ　ｒｕｓｓｅｌａｅ）、レッドバンデッドスティンクバグ（Ｐｉｅｚｏｄｏｒｕｓ　ｇｕｉｌｄｉｎｉｉ）、イチモンジカメムシ（Ｐｉｅｚｏｄｏｒｕｓ　ｈｙｂｎｅｒｉ）、ミカンコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ　ｃｉｔｒｉ）、フジコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ　ｋｕｒａｕｎｈｉａｅ）、チャバネアオカメムシ（Ｐｌａｕｔｉａ　ｃｒｏｓｓｏｔａ）、ミカンマルカイガラムシ（Ｐｓｅｕｄａｏｎｉｄｉａ　ｄｕｐｌｅｘ）、チャノマルカイガラムシ（Ｐｓｅｕｄａｏｎｉｄｉａ　ｐａｅｏｎｉａｅ）、クワシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ　ｐｅｎｔａｇｏｎａ）、ウメシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ　ｐｒｕｎｉｃｏｌａ）、ガハニコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ　ｃａｌｃｅｏｌａｒｉａｅ）、クワコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ　ｃｏｍｓｔｏｃｋｉ）、ナガオコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ　ｌｏｎｇｉｓｐｉｎｕｓ）、コットンフリーホッパー（Ｐｓｕｅｄａｔｏｍｏｓｃｅｌｉｓ　ｓｅｒｉａｔｕｓ）、ナシキジラミ（Ｐｓｙｌｌａ　ｐｙｒｉｓｕｇａ）、ミカンワタカイガラムシ（Ｐｕｌｖｉｎａｒｉａ　ａｕｒａｎｔｉｉ）、Ｑｕｅｓａｄａ　ｇｉｇａｓ、イナズマヨコバイ（Ｒｅｃｉｌｉａ　ｄｏｒｓａｌｉｓ）、トウモロコシアブラムシ（Ｒｈｏｐａｌｏｓｉｐｈｕｍ　ｍａｉｄｉｓ）、ムギクビレアブラムシ（Ｒｈｏｐａｌｏｓｉｐｈｕｍ　ｐａｄｉ）、アカヒメヘリカメムシ（Ｒｈｏｐａｌｕｓ　ｍｓｃｕｌａｔｕｓ）、ホソヘリカメムシ（Ｒｉｐｔｏｒｔｕｓ　ｃｌａｖａｔｕｓ）、Ｓｃａｐｔｏｃｏｒｉｓ　ｃａｓｔａｎｅａ、イネクロカメムシ（Ｓｃｏｔｉｎｏｐｈｏｒａ　ｌｕｒｉｄａ）、イングリッシュグレインエイフィッド（Ｓｉｔｏｂｉｏｎ　ａｖｅｎａｅ）
　セジロウンカ（Ｓｏｇａｔｅｌｌａ　ｆｕｒｃｉｆｅｒａ）、ナガムギカスミカメ（Ｓｔｅｎｏｄｅｍａ　ｓｉｂｉｒｉｃｕｍ）、アカスジカスミカメ（Ｓｔｅｎｏｔｕｓ　ｒｕｂｒｏｖｉｔｔａｔｕｓ）、ナシグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ　ｎａｓｈｉ）、ツツジグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ　ｐｙｒｉｏｉｄｅｓ）、Ｔａｇｏｓｏｄｅｓ　ｏｒｉｚｉｃｏｌｕｓ、コバネヒョウタンナガカメムシ（Ｔｏｇｏ　ｈｅｍｉｐｔｅｒｕｓ）、コミカンアブラムシ（Ｔｏｘｏｐｔｅｒａ　ａｕｒａｎｔｉｉ）、ミカンクロアブラムシ（Ｔｏｘｏｐｔｅｒａ　ｃｉｔｒｉｃｉｄａ）、オンシツコナジラミ（Ｔｒｉａｌｅｕｒｏｄｅｓ　ｖａｐｏｒａｒｉｏｒｕｍ）、Ｔｒｉａｔｏｍａ　ｄｉｍｉｄｉａｔａ、ブラジルサシガメ（Ｔｒｉａｔｏｍａ　ｉｎｆｅｓｔａｎｓ）、オオサシガメ（Ｔｒｉａｔｏｍａ　ｒｕｂｒｏｆａｓｃｉａｔａ）、イネホソミドリカスミカメ（Ｔｒｉｇｏｎｏｔｙｌｕｓ　ｃａｅｌｅｓｔｉａｌｉｕｍ）、ミカントガリキジラミ（Ｔｒｉｏｚａ　ｅｒｙｔｒｅａｅ）、ニセヤノネカイガラムシ（Ｕｎａｓｐｉｓ　ｃｉｔｒｉ）
マサキナガカイガラムシ（Ｕｎａｓｐｉｓ　ｅｕｏｎｙｍｉ）、ヤノネカイガラムシ（Ｕｎａｓｐｉｓ　ｙａｎｏｎｅｎｓｉｓ）、ブドウネアブラムシ（Ｄａｋｔｕｌｏｓｐｈａｉｒａ　Ｖｉｔｉｆｏｌｉａｅ）等のカメムシ目（Ｈｅｍｉｐｔｅｒａ）害虫；
ネギコガ（Ａｃｒｏｌｅｐｉｏｐｓｉｓ　ｓａｐｐｏｒｅｎｓｉｓ）、ヤマノイモコガ（Ａｃｒｏｌｅｐｉｏｐｓｉｓ　ｓｕｚｕｋｉｅｌｌａ）、チャノコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｈｏｎｍａｉ）、リンゴコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｏｒａｎａ　ｆａｃｉａｔａ）、アケビコノハ（Ａｄｒｉｓ　ｔｙｒａｎｎｕｓ）、ナカジロシタバ（Ａｅｄｉａ　ｌｅｕｃｏｍｅｌａｓ）、タマナヤガ（Ａｇｒｏｔｉｓ　ｉｐｓｉｌｏｎ）、カブラヤガ（Ａｇｒｏｔｉｓ　ｓｅｇｅｔｕｍ）、コットンリーフワーム（Ａｌａｂａｍａ　ａｒｇｉｌｌａｃｅａ）、モモキバガ（Ａｎａｒｓｉａ　ｌｉｎｅａｔｅｌｌａ）、ベルベットビーンキャタピラー（Ａｎｔｉｃａｒｓｉａ　ｇｅｍｍａｔａｌｉｓ）、リンゴモンハマキ（Ａｒｃｈｉｐｓ　ｂｒｅｖｉｐｌｉｃａｎｕｓ）、ミダレカクモンハマキ（Ａｒｃｈｉｐｓ　ｆｕｓｃｏｃｕｐｒｅａｎｕｓ）、リンゴヒメシンクイ（Ａｒｇｙｒｅｓｔｈｉａ　ｃｏｎｊｕｇｅｌｌａ）、ヨモギエダシャク（Ａｓｃｏｔｉｓ　ｓｅｌｅｎａｒｉａ）、タマナギンウワバ（Ａｕｔｏｇｒａｐｈａ　ｎｉｇｒｉｓｉｇｎａ）、ナシチビガ（Ｂｕｃｃｕｌａｔｒｉｘ　ｐｙｒｉｖｏｒｅｌｌａ）、チャノホソガ（Ｃａｌｏｐｔｉｌｉａ　ｔｈｅｉｖｏｒａ）、リンゴハマキホソガ（Ｃａｌｏｐｔｉｌｉａ　ｚａｃｈｒｙｓａ）、モモシンクイガ（Ｃａｒｐｏｓｉｎａ　ｎｉｐｏｎｅｎｓｉｓ）、モモシンクイガ（Ｃａｒｐｏｓｉｎａ　ｓａｓａｋｉｉ）、ダークヘディドステムボーラー（Ｃｈｉｌｏ　ｐｏｌｙｃｈｒｙｓｕｓ）、ニカメイガ（Ｃｈｉｌｏ　ｓｕｐｐｒｅｓｓａｌｉｓ）、チャハマキ（Ｃｈｏｒｉｓｔｏｎｅｕｒａ　ｍａｇｎａｎｉｍａ）、コブノメイガ（Ｃｎａｐｈａｌｏｃｒｏｃｉｓ　ｍｅｄｉｎａｌｉｓ）、モモノゴマダラノメイガ（Ｃｏｎｏｇｅｔｈｅｓ　ｐｕｎｃｔｉｆｅｒａｌｉｓ）、ミツモンキンウワバ（Ｃｔｅｎｏｐｌｕｓｉａ　ａｇｎａｔａ）、コドリングモス（Ｃｙｄｉａ　ｐｏｍｏｎｅｌｌａ）、ワタヘリクロノメイガ（Ｄｉａｐｈａｎｉａ　ｉｎｄｉｃａ）、シュガーケーンボーラー（Ｄｉａｔｒａｅａ　ｓａｃｃｈａｒａｌｉｓ）、モロコシマダラメイガ（Ｅｌａｓｍｏｐａｌｐｕｓ　ｌｉｇｎｏｓｅｌｌｕｓ）、グレープベリーモス（Ｅｎｄｏｐｉｚａ　ｖｉｔｅａｎａ）、チャマダラメイガ（Ｅｐｈｅｓｔｉａ　ｅｌｕｔｅｌｌａ）、シロイチモジマダラメイガ（Ｅｔｉｅｌｌａ　ｚｉｎｃｋｅｎｅｌｌａ）、チャドクガ（Ｅｕｐｒｏｃｔｉｓ　ｐｓｅｕｄｏｃｏｎｓｐｅｒｓａ）、クワノメイガ（Ｇｌｙｐｈｏｄｅｓ　ｐｙｌｏａｌｉｓ）、スモモヒメシンクイ（Ｇｒａｐｈｏｌｉｔａ　ｄｉｍｏｒｐｈａ）、リンゴコシンクイガ（Ｇｒａｐｈｏｌｉｔａ　ｉｎｏｐｉｎａｔａ）、ナシヒメシンクイ（Ｇｒａｐｈｏｌｉｔａ　ｍｏｌｅｓｔａ）、イモキバガ（Ｈｅｌｃｙｓｔｏｇｒａｍｍａ　ｔｒｉａｎｎｕｌｅｌｌａ）、オオタバコガ（Ｈｅｌｉｃｏｖｅｒｐａ　ａｒｍｉｇｅｒａ）、タバコガ（Ｈｅｌｉｃｏｖｅｒｐａ　ａｓｓｕｌｔａ）、コットンボールワーム（Ｈｅｌｉｃｏｖｅｒｐａ　ｚｅａ）、タバコバッドワーム（Ｈｅｌｉｏｔｈｉｓ　ｖｉｒｅｓｃｅｎｓ）、ハイマダラノメイガ（Ｈｅｌｌｕｌａ　ｕｎｄａｌｉｓ）、チャハマキ（Ｈｏｍｏｎａ　ｍａｇｎａｎｉｍａ）、アメリカシロヒトリ（Ｈｙｐｈａｎｔｒｉａ　ｃｕｎｅａ）、マメシンクイガ（Ｌｅｇｕｍｉｎｉｖｏｒａ　ｇｌｙｃｉｎｉｖｏｒｅｌｌａ）、クワゴマダラヒトリ（Ｌｅｍｙｒａ　ｉｍｐａｒｉｌｉｓ）、エッグプラントフルーツボーラー（Ｌｅｕｃｉｎｏｄｅｓ　ｏｒｂｏｎａｌｉｓ）、コーヒーリーフマイナー（Ｌｅｕｃｏｐｔｅｒａ　ｃｏｆｆｅｅｌｌａ）、ヨーロピアングレープバインモス（Ｌｏｂｅｓｉａ　ｂｏｔｒａｎａ）、マイマイガ（Ｌｙｍａｎｔｒｉａ　ｄｉｓｐａｒ）、モモハモグリガ（Ｌｙｏｎｅｔｉａ　ｃｌｅｒｋｅｌｌａ）、ギンモンハモグリガ（Ｌｙｏｎｅｔｉａ　ｐｒｕｎｉｆｏｌｉｅｌｌａ　ｍａｌｉｎｅｌｌａ）、ヨトウガ（Ｍａｍｅｓｔｒａ　ｂｒａｓｓｉｃａｅ）、トマトホーンワーム（Ｍａｎｄｕｃａ　ｑｕｉｎｑｕｅｍａｃｕｌａｔａ）、タバコホーンワーム（Ｍａｎｄｕｃａ　ｓｅｘｔａ）、マメヒメサヤムシガ（Ｍａｔｓｕｍｕｒａｅｓｅｓ　ｐｈａｓｅｏｌｉ）、アワヨトウ（Ｍｙｔｈｉｍｎａ　ｓｅｐａｒａｔａ）、フタオビコヤガ（Ｎａｒａｎｇａ　ａｅｎｅｓｃｅｎｓ）、ライスケースワーム（Ｎｙｍｐｈｕｌａ　ｄｅｐｕｎｃｔａｌｉｓ）、クワヒメハマキ（Ｏｌｅｔｈｒｅｕｔｅｓ　ｍｏｒｉ）、ヒメシロモンドクガ（Ｏｒｇｙｉａ　ｔｈｙｅｌｌｉｎａ）、アワノメイガ（Ｏｓｔｒｉｎｉａ　ｆｕｒｎａｃａｌｉｓ）、ヨーロピアンコーンボーラー（Ｏｓｔｒｉｎｉａ　ｎｕｂｉｌａｌｉｓ）、アズキノメイガ（Ｏｓｔｒｉｎｉａ　ｓｃａｐｕｌａｌｉｓ）、トビハマキ（Ｐａｎｄｅｍｉｓ　ｈｅｐａｒａｎａ）、アゲハチョウ（Ｐａｐｉｌｉｏ　ｘｕｔｈｕｓ）、シバツトガ（Ｐａｒａｐｅｄｉａｓｉａ　ｔｅｔｅｒｒｅｌｌａ）、イチモンジセセリ（Ｐａｒｎａｒａ　ｇｕｔｔａｔａ）、ワタアカミムシ（Ｐｅｃｔｉｎｏｐｈｏｒａ　ｇｏｓｓｙｐｉｅｌｌａ）、ジャガイモガ（Ｐｈｔｈｏｒｉｍａｅａ　ｏｐｅｒｃｕｌｅｌｌａ）、ミカンハモグリガ（Ｐｈｙｌｌｏｃｎｉｓｔｉｓ　ｃｉｔｒｅｌｌａ）、キンモンホソガ（Ｐｈｙｌｌｏｎｏｒｙｃｔｅｒ　ｒｉｎｇｏｎｉｅｌｌａ）、オオモンシロチョウ（Ｐｉｅｒｉｓ　ｂｒａｓｓｉｃａｅ）、モンシロチョウ（Ｐｉｅｒｉｓ　ｒａｐａｅ）、ノシメマダラメイガ（Ｐｌｏｄｉａ　ｉｎｔｅｒｐｕｎｃｔｅｌｌａ）、イネキンウワバ（Ｐｌｕｓｉａ　ｆｅｓｔｕｃａｅ）、コナガ（Ｐｌｕｔｅｌｌａ　ｘｙｌｏｓｔｅｌｌａ）、ソイビーンルーパー（Ｐｓｅｕｄｏｐｌｕｓｉａ　ｉｎｃｌｕｄｅｎｓ）、イッテンオオメイガ（Ｓｃｉｒｐｏｐｈａｇａ　ｉｎｃｅｒｔｕｌａｓ）、ホワイトステムボーラー（Ｓｃｉｒｐｏｐｈａｇａ　ｉｎｎｏｔａｔａ）、イネヨトウ（Ｓｅｓａｍｉａ　ｉｎｆｅｒｅｎｓ）、スジキリヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｄｅｐｒａｖａｔａ）、サザンアーミーワーム（Ｓｐｏｄｏｐｔｅｒａ　ｅｒｉｄａｎｉａ）、シロイチモジヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｅｘｉｇｕａ）、フォールアーミーワーム（Ｓｐｏｄｏｐｔｅｒａ　ｆｒｕｇｉｐｅｒｄａ）、コットンリーフワーム（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｔｏｒａｌｉｓ）、ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｕｒａ）、シロナヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｍａｕｒｉｔｉａ）、ナシホソガ（Ｓｐｕｌｅｒｒｉｎａ　ａｓｔａｕｒｏｔａ）、カキノヘタムシガ（Ｓｔａｔｈｍｏｐｏｄａ　ｍａｓｉｎｉｓｓａ）、ヒメコスカシバ（Ｓｙｎａｎｔｈｅｄｏｎ　ｔｅｎｕｉｓ）、イガ（Ｔｉｎｅａ　ｔｒａｎｓｌｕｃｅｎｓ）、イラクサギンウワバ（Ｔｒｉｃｈｏｐｌｕｓｉａ　ｎｉ）、Ｔｕｔａ　ａｂｓｏｌｕｔａ、等のチョウ目（Ｌｅｐｉｄｏｐｔｅｒａ）害虫；
トビイロムナボソコメツキ（Ａｇｒｉｏｔｅｓ　ｆｕｓｃｉｃｏｌｌｉｓ）、ガイマイゴミムシダマシ（Ａｌｐｈｉｔｏｂｉｕｓ　ｄｉａｐｅｒｉｎｕｓ）、ドウガネブイブイ（Ａｎｏｍａｌａ　ｃｕｐｒｅａ）、ヒメコガネ（Ａｎｏｍａｌａ　ｒｕｆｏｃｕｐｒｅａ）、ゴマダラカミキリ（Ａｎｏｐｌｏｐｈｏｒａ　ｍａｌａｓｉａｃａ）、ワタミゾウムシ（Ａｎｔｈｏｎｏｍｕｓ　ｇｒａｎｄｉｓ）、ヒメマルカツオブシムシ（Ａｎｔｈｒｅｎｕｓ　ｖｅｒｂａｓｃｉ）、クビアカツヤカミキリ（Ａｒｏｍｉａ　ｂｕｎｇｉｉ）、ウリハムシ（Ａｕｌａｃｏｐｈｏｒａ　ｆｅｍｏｒａｌｉｓ）、アズキゾウムシ（Ｃａｌｌｏｓｏｂｒｕｃｈｕｓ　ｃｈｉｎｅｎｓｉｓ）、ビーンリーフビートル（Ｃｅｒｏｔｏｍａ　ｔｒｉｆｕｒｃａｔａ）、テンサイトビハムシ（Ｃｈａｅｔｏｃｎｅｍａ　ｃｏｎｃｉｎｎａ）、サツマイモヒサゴトビハムシ（Ｃｈａｅｔｏｃｎｅｍａ　ｃｏｎｆｉｎｉｓ）、コーンフリービートル（Ｃｈａｅｔｏｃｎｅｍａ　ｐｕｌｉｃａｒｉａ）、アカチビヒラタムシ（Ｃｒｙｐｔｏｌｅｓｔｅｓ　ｆｅｒｒｕｇｉｎｅｕｓ）、アリモドキゾウムシ（Ｃｙｌａｓ　ｆｏｒｍｉｃａｒｉｕｓ）、ハラジロカツオブシムシ（Ｄｅｒｍｅｓｔｅｓ　ｍａｃｕｌａｔｅｓ）、バンデッドキューカンバービートル（Ｄｉａｂｒｏｔｉｃａ　ｂａｌｔｅａｔａ）、ノーザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｂａｒｂｅｒｉ）、キューカビットビートル（Ｄｉａｂｒｏｔｉｃａ　ｓｐｅｃｉｏｓａ）、サザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｕｎｄｅｃｉｍｐｕｎｃｔａｔａ）、ウエスタンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｖｉｒｇｉｆｅｒａ）、メキシカンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｖｉｒｇｉｆｅｒａ　ｚｅａｅ）、
イネトゲハムシ（Ｄｉｃｌａｄｉｓｐａ　ａｒｍｉｇｅｒａ）、Ｄｉｌｏｂｏｄｅｒｕｓ　ａｂｄｅｒｕｓ、イネゾウムシ（Ｅｃｈｉｎｏｃｎｅｍｕｓ　ｓｑｕａｍｅｕｓ）、メキシカンビートビートル（Ｅｐｉｌａｃｈｎａ　ｖａｒｉｖｅｓｔｉｓ）、インゲンテントウ（Ｅｐｉｌａｃｈｎａ　ｖａｒｉｖｅｓｔｉｓ）、ニジュウヤホシテントウ（Ｅｐｉｌａｃｈｎａ　ｖｉｇｉｎｔｉｏｃｔｏｐｕｎｃｔａｔａ）、タバコノミハムシ（Ｅｐｉｔｒｉｘ　ｈｉｒｔｉｐｅｎｎｉｓ）、ヒメヒラタケシキスイ（Ｅｐｕｒａｅａ　ｄｏｍｉｎａ）、イモゾウムシ（Ｅｕｓｃｅｐｅｓ　ｐｏｓｔｆａｓｃｉａｔｕｓ）、コアオハナムグリ（Ｇａｍｅｔｉｓ　ｊｕｃｕｎｄａ）、ナガチャコガネ（Ｈｅｐｔｏｐｈｙｌｌａ　ｐｉｃｅａ）、アルファルファタコゾウムシ（Ｈｙｐｅｒａ　ｐｏｓｔｉｃａ）、コーヒーベリーボーラー（Ｈｙｐｏｔｈｅｎｅｍｕｓ　ｈａｍｐｅｉ）、タバコシバンムシ（Ｌａｓｉｏｄｅｒｍａ　ｓｅｒｒｉｃｏｒｎｅ）、コロラドハムシ（Ｌｅｐｔｉｎｏｔａｒｓａ　ｄｅｃｅｍｌｉｎｅａｔａ）、イネミズゾウムシ（Ｌｉｓｓｏｒｈｏｐｔｒｕｓ　ｏｒｙｚｏｐｈｉｌｕｓ）、ヒラタキクイムシ（Ｌｙｃｔｕｓｂｒｕｎｎｅｕｓ）、
マルクビクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｆｏｒｔｎｕｍｉ）、クシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｌｅｇａｔｕｓ）、オキナワカンシャクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｏｋｉｎａｗｅｎｓｉｓ）、カンシャクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｔａｍｓｕｙｅｎｓｉｓ）、Ｍｉｇｄｏｌｕｓ　ｆｒｙａｎｕｓ、マツノマダラカミキリ（Ｍｏｎｏｃｈａｍｕｓ　ａｌｔｅｒｎａｔｕｓ）、ノコギリヒラタムシ（Ｏｒｙｚａｅｐｈｉｌｕｓ　ｓｕｒｉｎａｍｅｎｓｉｓ）、キンケクチブトゾウムシ（Ｏｔｉｏｒｈｙｎｃｈｕｓ　ｓｕｌｃａｔｕｓ）、クビアカクビホソハムシ（Ｏｕｌｅｍａ　ｍｅｌａｎｏｐｕｓ）、イネドロオイムシ（Ｏｕｌｅｍａ　ｏｒｙｚａｅ）、アオバアリガタハネカクシ（Ｐａｅｄｅｒｕｓ　ｆｕｓｃｉｐｅｓ）、ジューン・ビートル（Ｐｈｙｌｌｏｐｈａｇａ　ｃｒｉｎｉｔａ）、キャベッジフリービートル（Ｐｈｙｌｌｏｔｒｅｔａ　ｃｒｕｃｉｆｅｒａｅ）、ウエスタンブラックフリービートル（Ｐｈｙｌｌｏｔｒｅｔａ　ｐｕｓｉｌｌａ）、キスジノミハムシ（Ｐｈｙｌｌｏｔｒｅｔａ　ｓｔｒｉｏｌａｔａ）、マメコガネ（Ｐｏｐｉｌｌｉａ　ｊａｐｏｎｉｃａ）、キボシカミキリ（Ｐｓａｃｏｔｈｅａ　ｈｉｌａｒｉｓ）、ナスナガスネトビハムシ（Ｐｓｙｌｌｉｏｄｅｓ　ａｎｇｕｓｔｉｃｏｌｌｉｓ）、キャベッジステムフリービートル（Ｐｓｙｌｌｉｏｄｅｓ　ｃｈｒｙｓｏｃｅｐｈａｌａ）、ホップフリービートル（Ｐｓｙｌｌｉｏｄｅｓ　ｐｕｎｃｔｕｌａｔａ）、ナガシンクイムシ（Ｒｈｉｚｏｐｅｒｔｈａ　ｄｏｍｉｎｉｃａ）、モモチョッキリゾウムシ（Ｒｈｙｎｃｈｉｔｅｓ　ｈｅｒｏｓ）、グラナリーウィービル（Ｓｉｔｏｐｈｉｌｕｓ　ｇｒａｎａｒｉｕｓ）、ココクゾウムシ（Ｓｉｔｏｐｈｉｌｕｓ　ｏｒｙｚａｅ）、コクゾウムシ（Ｓｉｔｏｐｈｉｌｕｓ　ｚｅａｍａｉｓ）、サザンコーンビルバグ（Ｓｐｈｅｎｏｐｈｏｒｕｓ　ｃａｌｌｏｓｕｓ）、シュガーケーンウィービル（Ｓｐｈｅｎｏｐｈｏｒｕｓ　ｌｅｖｉｓ）、シバオサゾウムシ（Ｓｐｈｅｎｏｐｈｏｒｕｓ　ｖｅｎａｔｕｓ　ｖｅｓｔｉｔｕｓ）、ジンサンシバンムシ（Ｓｔｅｇｏｂｉｕｍ　ｐａｎｉｃｅｕｍ）、ソイビーンストークウィービル（Ｓｔｅｒｎｅｃｈｕｓ　ｓｕｂｓｉｇｎａｔｕｓ）、チャイロコメノゴミムシダマシ（Ｔｅｎｅｂｒｉｏ　ｍｏｌｉｔｏｒ）、マツノキクイムシ（Ｔｏｍｉｃｕｓ　ｐｉｎｉｐｅｒｄａ）、コクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ　ｃａｓｔａｎｅｕｍ）、ヒラタコクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ　ｃｏｎｆｕｓｕｍ）、ヒメアカカツオブシムシ（Ｔｒｏｇｏｄｅｒｍａ　ｇｒａｎａｒｉｕｍ）、ブドウトラカミキリ（Ｘｙｌｏｔｒｅｃｈｕｓ　ｐｙｒｒｈｏｄｅｒｕｓ）等のコウチュウ目（Ｃｏｌｅｏｐｔｅｒａ）害虫；
ヒラズハナアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｉｎｔｏｎｓａ）、ミカンキイロアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｏｃｃｉｄｅｎｔａｌｉｓ）、イネクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓ　ａｃｕｌｅａｔｕｓ）、クロトンアザミウマ（Ｈｅｌｉｏｔｈｒｉｐｓ　ｈａｅｍｏｒｒｈｏｉｄａｌｉｓ）、カキクダアザミウマ（Ｐｏｎｔｉｃｕｌｏｔｈｒｉｐｓ　ｄｉｏｓｐｙｒｏｓｉ）、チャノキイロアザミウマ（Ｓｃｉｒｔｏｔｈｒｉｐｓ　ｄｏｒｓａｌｉｓ）、キイロハナアザミウマ（Ｔｈｒｉｐｓ　ｆｌａｖｕｓ）、ミナミキイロアザミウマ（Ｔｈｒｉｐｓ　ｐａｌｍｉ）、ネギアザミウマ（Ｔｈｒｉｐｓ　ｔａｂａｃｉ）等のアザミウマ目（Ｔｈｙｓａｎｏｐｔｅｒａ）害虫；
ネッタイシマカ（Ａｅｄｅｓ　ａｅｇｙｐｔｉ）、ヒトスジシマカ（Ａｅｄｅｓ　ａｌｂｏｐｉｃｕｔｕｓ）、イネハモグリバエ（Ａｇｒｏｍｙｚａ　ｏｒｙｚａｅ）、Ａｎｏｐｈｅｌｅｓ　ａｌｂｉｍａｎｕｓ、Ａｎｏｐｈｅｌｅｓ　ａｒａｂｉｅｎｓｉｓ、Ａｎｏｐｈｅｌｅｓ　ｃｏｌｕｚｚｉｉ、Ａｎｏｐｈｅｌｅｓ　ｄａｒｌｉｎｇｉ、Ａｎｏｐｈｅｌｅｓ　ｆａｒａｕｔｉ、Ａｎｏｐｈｅｌｅｓ　ｆｕｎｅｓｔｕｓ、ガンビエハマダラカ（Ａｎｏｐｈｅｌｅｓ　ｇａｍｂｉａｅ）、Ａｎｏｐｈｅｌｅｓ　ｍｉｎｉｍｕｓ、シナハマダラカ（Ａｎｏｐｈｅｌｅｓ　ｓｉｎｅｓｉｓ）、ステフェンスハマダラカ（Ａｎｏｐｈｅｌｅｓ　ｓｔｅｐｈｅｎｓｉ）、Ａｎｏｐｈｅｌｅｓ　ｓｕｎｄａｉｃｕｓ、ダイズサヤタマバエ（Ａｓｐｈｏｎｄｙｌｉａ　ｙｕｓｈｉｍａｉ）、ウリミバエ（Ｂａｃｔｒｏｃｅｒａ　ｃｕｃｕｒｂｉｔａｅ）、ミカンコミバエ（Ｂａｃｔｒｏｃｅｒａ　ｄｏｒｓａｌｉｓ）、ナスミバエ（Ｂａｃｔｒｏｃｅｒａ　ｌａｔｉｆｒｏｎｓ）、オリーブミバエ（Ｂａｃｔｒｏｃｅｒａ　ｏｌｅａｅ）、クインスランドミバエ（Ｂａｃｔｒｏｃｅｒａ　ｔｒｙｏｎｉ）、チビクロバネキノコバエ（Ｂｒａｄｙｓｉａ　ｄｉｆｆｏｒｍｉｓ）、チチュウカイミバエ（Ｃｅｒａｔｉｔｉｓ　ｃａｐｉｔａｔａ）、オオユスリカ（Ｃｈｉｒｏｎｏｍｕｓ　ｐｌｕｍｏｓｕｓ）、セスジユスリカ（Ｃｈｉｒｏｎｏｍｕｓ　ｙｏｓｈｉｍａｔｓｕｉ）、イネキモグリバエ（Ｃｈｌｏｒｏｐｓ　ｏｒｙｚａｅ）、ナモグリバエ（Ｃｈｒｏｍａｔｏｍｙｉａ　ｈｏｒｔｉｃｏｌａ）、オオチョウバエ（Ｃｌｏｇｍｉａ　ａｌｂｉｐｕｎｃｔａｔａ）、チカイエカ（Ｃｕｌｅｘ　ｐｉｐｉｅｎｓ　ｆ．　ｍｏｌｅｓｔｕｓ）、アカイエカ（Ｃｕｌｅｘ　ｐｉｐｉｅｎｓ　ｐａｌｌｅｎｓ）、トビイロイエカ（Ｃｕｌｅｘ　ｐｉｐｉｅｎｓ　ｐｉｐｉｅｎｓ）、ネッタイイエカ（Ｃｕｌｅｘ　ｑｕｉｎｑｕｅｆａｓｃｉａｔｕｓ）、ニセシロハシイエカ（Ｃｕｌｅｘ　ｖｉｓｈｎｕｉ）、タマネギバエ（Ｄｅｌｉａ　ａｎｔｉｑｕｅ）、タネバエ（Ｄｅｌｉａ　ｐｌａｔｕｒａ）、キイロショウジョウバエ（Ｄｒｏｓｏｐｈｉｌａ　ｍｅｌａｎｏｇａｓｔｅｒ）、オウトウショウジョウバエ（Ｄｒｏｓｏｐｈｉｌａ　ｓｕｚｕｋｉｉ）、Ｇｌｏｓｓｉｎａ　ｍｏｒｓｉｔａｎｓ、ツェツェバエ（Ｇｌｏｓｓｉｎａ　ｐａｌｐａｌｉｓ，　）、ノサシバエ（Ｈａｅｍａｔｏｂｉａ　ｉｒｒｉｔａｎｓ）、
イネヒメハモグリバエ（Ｈｙｄｒｅｌｌｉａ　ｇｒｉｓｅｏｌａ）、トウヨウイネクキミギワバエ（Ｈｙｄｒｅｌｌｉａ　ｐｈｉｌｉｐｐｉｎａ）、イネクキミギワバエ（Ｈｙｄｒｅｌｌｉａ　ｓａｓａｋｉｉ）、ウシバエ（Ｈｙｐｏｄｅｒｍａ　ｂｏｖｉｓ）、スジウシバエ（Ｈｙｐｏｄｅｒｍａ　ｌｉｎｅａｔｕｍ）、トクナガヌカカ（Ｌｅｐｔｏｃｏｎｏｐｓ　ｎｉｐｐｏｎｅｎｓｉｓ）、ナスハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｂｒｙｏｎｉａｅ）、ネギハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｃｈｉｎｅｎｓｉｓ）、トマトハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｓａｔｉｖａｅ）、マメハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｔｒｉｆｏｌｉｉ）、ヘシアンフライ（Ｍａｙｅｔｉｏｌａ　ｄｅｓｔｒｕｃｔｏｒ）、ヒツジシラミバエ（Ｍｅｌｏｐｈａｇｕｓ　ｏｖｉｎｕｓ）、イエバエ（Ｍｕｓｃａ　ｄｏｍｅｓｔｉｃａ）、オオイエバエ（Ｍｕｓｃｉｎａ　ｓｔａｂｕｌａｎｓ）、ヒツジバエ（Ｏｅｓｔｒｕｓ　ｏｖｉｓ）、テンサイモグリハナバエ（Ｐｅｇｏｍｙａ　ｃｕｎｉｃｕｌａｒｉａ）、キアシオオブユ（Ｐｒｏｓｉｍｕｌｉｕｍ　ｙｅｚｏｅｎｓｉｓ）、アップルマゴット（Ｒｈａｇｏｌｅｔｉｓ　ｐｏｍｏｎｅｌｌａ）、Ｓｉｍｕｌｉｕｍ　ｄａｍｎｏｓｕｍ、アシマダラブユ（Ｓｉｍｕｌｉｕｍ　ｊａｐｏｎｉｃｕｍ）、ムギアカタマバエ（Ｓｉｔｏｄｉｐｌｏｓｉｓ　ｍｏｓｅｌｌａｎａ）、サシバエ（Ｓｔｏｍｏｘｙｓ　ｃａｌｃｉｔｒａｎｓ）、ウシアブ（Ｔａｂａｎｕｓ　ｔｒｉｇｏｎｕｓ）、オオチョウバエ（Ｔｅｌｍａｔｏｓｃｏｐｕｓ　ａｌｂｉｐｕｎｃｔａｔｕｓ）、シュガービートルートマゴット（Ｔｅｔａｎｏｐｓ　ｍｙｏｐａｅｆｏｒｍｉｓ）、キリウジガガンボ（Ｔｉｐｕｌａ　ａｉｎｏ）、コモンクレーンフライ（Ｔｉｐｕｌａ　ｏｌｅｒａｃｅａ）、ヨーロピアンクレーンフライ（Ｔｉｐｕｌａ　ｐａｌｕｄｏｓａ）等のハエ目（Ｄｉｐｔｅｒａ）害虫；
クリハバチ（Ａｐｅｔｈｙｍｕｓ　ｋｕｒｉ）、チュウレンジハバチ（Ａｒｇｅ　ｐａｇａｎａ）、ニホンカブラバチ（Ａｔｈａｌｉａ　ｊａｐｏｎｉｃａ）、カブラハバチ（Ａｔｈａｌｉａ　ｒｏｓａｅ）、ブラウンリーフカッティングアント（Ａｔｔａ　ｃａｐｉｇｕａｒａ）、クロオオアリ（Ｃａｍｐｏｎｏｔｕｓ　ｊａｐｏｎｉｃｕｓ）、ムネアカオオアリ（Ｃａｍｐｏｎｏｔｕｓ　ｏｂｓｃｕｒｉｐｅｓ）、クリタマバチ（Ｄｒｙｏｃｏｓｍｕｓ　ｋｕｒｉｐｈｉｌｕｓ）、グンタイアリ（Ｅｃｉｔｏｎ　ｂｕｒｃｈｅｌｌｉ）、Ｅｃｉｔｏｎ　ｓｃｈｍｉｔｔｉ、アルゼンチンアリ（Ｌｉｎｅｐｉｔｈｅｍａ　ｈｕｍｉｌｅ）、ファラオアント（Ｍｏｎｏｍｏｒｉｕｍ　ｐｈａｒａｏｎｉｓ）、ブルドックアント類（Ｍｙｒｍｅｃｉａ　ｓｐｐ．）、マツノキハバチ（Ｎｅｏｄｉｐｒｉｏｎ　ｓｅｒｔｉｆｅｒ）、セグロアシナガバチ（Ｐｏｌｉｓｔｅｓ　ｊｏｋａｈａｍａｅ）、アカカミアリ（Ｓｏｌｅｎｏｐｓｉｓ　ｇｅｍｉｎａｔａ）、ヒアリ（Ｓｏｌｅｎｏｐｓｉｓ　ｉｎｖｉｃｔａ）、ファイヤーアント類（Ｓｏｌｅｎｏｐｓｉｓ　ｓｐｐ．）、モミノオオキバチ（Ｕｒｏｃｅｒｕｓ　ｇｉｇａｓ）、コガタスズメバチ（Ｖｅｓｐａ　ａｎａｌｉｓ）、オオスズメバチ（Ｖｅｓｐａ　ｍａｎｄａｒｉｎａ）、ケブカスズメバチ（Ｖｅｓｐａ　ｓｉｍｉｌｌｉｍａ）、ツマアカスズメバチ（Ｖｅｓｐａ　ｖｅｌｕｔｉｎａ）等のハチ目（Ｈｙｍｅｎｏｐｔｅｒａ）害虫；
ヨーロッパイエコオロギ（Ａｃｈｅｔａ　ｄｏｍｅｓｔｉｃａ）、ケラ（Ｇｒｙｌｌｏｔａｌｐａ　ｏｒｉｅｎｔａｌｉｓ）、トノサマバッタ（Ｌｏｃｕｓｔａ　ｍｉｇｒａｔｏｒｉａ）、ツーストライプドグラスホッパー（Ｍｅｌａｎｏｐｌｕｓ　ｂｉｖｉｔｔａｔｕｓ）、ディファレンシャルグラスホッパー（Ｍｅｌａｎｏｐｌｕｓ　ｄｉｆｆｅｒｅｎｔｉａｌｉｓ）、レッドレッグドグラスホッパー（Ｍｅｌａｎｏｐｌｕｓ　ｆｅｍｕｒｒｕｂｒｕｍ）、マイグレトリーグラスホッパー　（Ｍｅｌａｎｏｐｌｕｓ　ｓａｎｇｕｉｎｉｐｅｓ）、ハネナガイナゴ（Ｏｘｙａ　ｊａｐｏｎｉｃａ）、コバネイナゴ（Ｏｘｙａ　ｙｅｚｏｅｎｓｉｓ）、サバクワタリバッタ（Ｓｃｈｉｓｔｏｃｅｒｃａ　ｇｒｅｇａｒｉａ）、エンマコオロギ（Ｔｅｌｅｏｇｒｙｌｌｕｓ　ｅｍｍａ）等のバッタ目（Ｏｒｔｈｏｐｔｅｒａ）害虫；
　キボシマルトビムシ（Ｂｏｕｒｌｅｔｉｅｌｌａ　ｈｏｒｔｅｎｓｉｓ）、トゲナシシロトビムシ（Ｏｎｙｃｈｉｕｒｕｓ　ｆｏｌｓｏｍｉ）、シベリアシロトビムシ（Ｏｎｙｃｈｉｕｒｕｓ　ｓｉｂｉｒｉｃｕｓ）等のトビムシ目（Ｃｏｌｌｅｍｂｏｌａ）害虫；
トウヨウゴキブリ（Ｂｌａｔｔａ　ｏｒｉｅｎｔａｌｉｓ）、チャバネゴキブリ（Ｂｌａｔｔｅｌｌａ　ｇｅｒｍａｎｉｃａ）、イエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、コウシュウイエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ　ｇｕａｎｇｚｈｏｕｅｎｓｉｓ）、Ｃｏｒｎｉｔｅｒｍｅｓ　ｃｕｍｕｌａｎｓ、タイワンシロアリ（Ｏｄｏｎｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、ワモンゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　Ａｍｅｒｉｃａｎａ）、コワモンゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ａｕｓｔｒａｌａｓｉａｅ）、トビイロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｂｒｕｎｎｅａ）、クロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｆｕｌｉｇｉｎｏｓａ）、ヤマトゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｊａｐｏｎｉｃａ）、アマミシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ａｍａｍｉａｎｕｓ）、カンモンシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｋａｎｍｏｎｅｎｓｉｓ）、ミヤタケシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｍｉｙａｔａｋｅｉ）、ヤマトシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｓｐｅｒａｔｕｓ）等のゴキブリ目（Ｂｌａｔｔｏｄｅａ）害虫；
イヌノミ（Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ　ｃａｎｉｓ）、ネコノミ（Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ　ｆｅｌｉｓ）、ニワトリノミ（Ｅｃｈｉｄｎｏｐｈａｇａ　ｇａｌｌｉｎａｃｅａ）、ヒトノミ（Ｐｕｌｅｘ　ｉｒｒｉｔａｎｓ）、スナノミ（Ｔｕｎｇａ　ｐｅｎｅｔｒａｎｓ）、ケオプスネズミノミ（Ｘｅｎｏｐｓｙｌｌａ　ｃｈｅｏｐｉｓ）等のノミ目（Ｓｉｈｏｎａｐｔｅｒａ）害虫；
ウシハジラミ（Ｂｏｖｉｃｏｌａ　ｂｏｖｉｓ）、ヒツジジラミ（Ｂｏｖｉｃｏｌａ　ｏｖｉｓ）、Ｄａｍａｌｉｎｉａ　ｆｏｒｆｉｃｕｌａ、ネコハジラミ（Ｆｅｌｉｃｏｌａ　ｓｕｂｒｏｓｔｒａｔｕｓ）、ウシジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｅｕｒｙｓｔｅｒｎｕｓ）、ブタジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｓｕｉｓ）、ヒツジ体幹寄生ホソジラミ（Ｌｉｎｏｇｎａｔｈｕｓ　ｏｖｉｌｌｕｓ）、ウシホソジラミ（Ｌｉｎｏｇｎａｔｈｕｓ　ｖｉｔｕｌｉ）、ヒラタチャタテ（Ｌｉｐｏｓｃｅｌｉｓ　ｂｏｓｔｒｙｃｈｏｐｈｉｌａ）、ウスグロチャタテ（Ｌｉｐｏｓｃｅｌｉｓ　ｃｏｒｒｏｄｅｎｓ）、カツブシチャタテ（Ｌｉｐｏｓｃｅｌｉｓ　ｅｎｔｏｍｏｐｈｉｌａ）、ソウメンチャタテ（Ｌｉｐｏｓｃｅｌｉｓ　ｐｅａｒｍａｎｉ）、ニワトリオオハジラミ（Ｍｅｎａｃａｎｔｈｕｓ　ｓｔｒａｍｉｎｅｕｓ）、ニワトリハジラミ（Ｍｅｎｏｐｏｎ　ｇａｌｌｉｎａｅ）、ケブカウシジラミ（Ｓｏｌｅｎｏｐｏｔｅｓ　ｃａｐｉｌｌａｔｕｓ）、イヌハジラミ（Ｔｒｉｃｈｏｄｅｃｔｅｓ　ｃａｎｉｓ）等のカジリムシ目（Ｐｓｏｃｏｄｅａ）害虫；
チャノナガサビダニ（Ａｃａｐｈｙｌｌａ　ｔｈｅａｖａｇｒａｎｓ）、カキサビダニ（Ａｃｅｒｉａ　ｄｉｏｓｐｙｒｉ）、Ａｃｅｒｉａ　ｔｏｓｉｃｈｅｌｌａ、チューリップサビダニ（Ａｃｅｒｉａ　ｔｕｌｉｐａｅ）、トマトサビダニ（Ａｃｕｌｏｐｓ　ｌｙｃｏｐｅｒｓｉｃｉ）、ミカンサビダニ（Ａｃｕｌｏｐｓ　ｐｅｌｅｋａｓｓｉ）、リンゴサビダニ（Ａｃｕｌｕｓ　ｓｃｈｌｅｃｈｔｅｎｄａｌｉ）、ローン・スターマダニ（Ａｍｂｌｙｏｍｍａ　ａｍｅｒｉｃａｎｕｍ）、メキシコ湾岸マダニ（Ａｍｂｌｙｏｍｍａ　ｍａｃｕｌａｔｕｍ）、オオマダニ（Ａｍｂｌｙｏｍｍａ　ｓｐｐ．）、ナガヒメダニ（Ａｒｇａｓ　ｐｅｒｓｉｃｕｓ）、オウシマダニ（Ｂｏｏｐｈｉｌｕｓ　ｍｉｃｒｏｐｌｕｓ）、ミナミヒメハダニ（Ｂｒｅｖｉｐａｌｐｕｓ　ｐｈｏｅｎｉｃｉｓ）、ネコツメダニ（Ｃｈｅｙｌｅｔｉｅｌｌａ　ｂｌａｋｅｉ）、イヌツメダニ（Ｃｈｅｙｌｅｔｉｅｌｌａ　ｙａｓｇｕｒｉ）、イヌニキビダニ（Ｄｅｍｏｄｅｘ　ｃａｎｉｓ）、ネコニキビダニ（Ｄｅｍｏｄｅｘ　ｃａｔｉ）、ロッキー山脈森林マダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ａｎｄｅｒｓｏｎｉ）、西海岸マダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｏｃｃｉｄｅｎｔａｌｉｓ）、アミメカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｒｅｃｔｉｃｕｌａｔｕｓ）、アミメマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｓｐｐ．）、タイワンカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｔａｉｗａｎｅｎｓｉｓ）、アメリカンドッグティック（Ｄｅｒｍａｃｅｎｔｏｒ　ｖａｒｉａｂｉｌｉｓ）、ワクモ（Ｄｅｒｍａｎｙｓｓｕｓ　ｇａｌｌｉｎａｅ）、コナヒョウヒダニ（Ｄｅｒｍａｔｏｐｈａｇｏｉｄｅｓ　ｆａｒｉｎａｅ）、ヤケヒョウヒダニ（Ｄｅｒｍａｔｏｐｈａｇｏｉｄｅｓ　ｐｔｅｒｏｎｙｓｓｉｎｕｓ）、ニセナシサビダニ（Ｅｒｉｏｐｈｙｅｓ　ｃｈｉｂａｅｎｓｉｓ）、ツリガネチマダニ（Ｈａｅｍａｏｐｈｙｓａｌｉｓ　ｃａｍｐａｎｕｌａｔａ）、キチマダニ（Ｈａｅｍａｏｐｈｙｓａｌｉｓ　ｆｌａｖａ）、ヤマトチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｊａｐｏｎｉｃａ）、フタトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｌｏｎｇｉｃｏｒｎｉｓ）、オオトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｍｅｇａｓｐｉｎｏｓａ）、Ｉｘｏｄｅｓ　ｈｏｌｏｃｙｃｌｕｓ、タネガタマダニ（Ｉｘｏｄｅｓ　ｎｉｐｐｏｎｅｎｓｉｓ）、マトマダニ（Ｉｘｏｄｅｓ　ｏｖａｔｕｓ）、西部クロアシダニ（Ｉｘｏｄｅｓ　ｐａｃｉｆｃｕｓ）、西部クロアシマダニ（Ｉｘｏｄｅｓ　ｐａｃｉｆｉｃｕｓ）、シュルツェマダニ（Ｉｘｏｄｅｓ　ｐｅｒｓｕｌｃａｔｕｓ）、ヒツジダニ（Ｉｘｏｄｅｓ　ｒｉｃｉｎｕｓ）、クロアシダニ（Ｉｘｏｄｅｓ　ｓｃａｐｕｌａｒｉｓ）、
ニワトリヒゼンダニ（Ｋｎｅｍｉｄｏｃｏｐｔｅｓ　ｓｐｐ．）、ウサギズツキダニ（Ｌｉｓｔｒｏｐｈｏｒｕｓ　ｇｉｂｂｕｓ）、ネコショウセンコウヒゼンダニ（Ｎｏｔｏｅｄｒｅｓ　ｃａｔｉ）、ネズミショウセンコウヒゼンダニ（Ｎｏｔｏｅｄｒｅｓ　ｍｕｒｉｓ）、イネハダニ（Ｏｌｉｇｏｎｙｃｈｕｓ　ｓｈｉｎｋａｊｉｉ）、イエダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ　ｂａｃｏｔｉ）、トリサシダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ　ｓｙｌｖｉａｒｕｍ）、ミミヒゼンダニ（Ｏｔｏｄｅｃｔｅｓ　ｃｙｎｏｔｉｓ）、ミカンハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｃｉｔｒｉ）、クワオオハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｍｏｒｉ）、リンゴハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｕｌｍｉ）、ハクサイダニ（Ｐｅｎｔｈａｌｅｕｓ　ｅｒｙｔｈｒｏｃｅｐｈａｌｕｓ）、ムギダニ（Ｐｅｎｔｈａｌｅｕｓ　ｍａｊｏｒ）、リュウキュウミカンサビダニ（Ｐｈｙｌｌｏｃｏｐｔｒｕｔａ　ｃｉｔｒｉ）、シトラスラストマイト（Ｐｈｙｌｌｏｃｏｐｔｒｕｔａ　ｏｌｅｉｖｏｒａ）、シクラメンホコリダニ（Ｐｈｙｔｏｎｅｍｕｓ　ｐａｌｌｉｄｕｓ）、チャノホコリダニ（Ｐｏｌｙｐｈａｇｏｔａｒｓｏｎｅｍｕｓ　ｌａｔｕｓ）、ウマキュウセンヒゼンダニ（Ｐｓｏｒｏｐｔｅｓ　ｅｑｕｉ）、ヒツジキュウセンダニ（Ｐｓｏｒｏｐｔｅｓ　ｏｖｉｓ）、キャトルチック（Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ａｎｎｕｌａｔｕｓ）、
Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ａｐｐｅｎｄｉｃｕｌａｔｕｓ、Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ｄｅｃｏｌｏｒａｔｕｓ、クリイロコイタマダニ（Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ｓａｎｇｕｉｎｅｕｓ）、ロビンネダニ（Ｒｈｉｚｏｇｌｙｐｈｕｓ　ｒｏｂｉｎｉ）、センコウヒゼンダニ（Ｓａｒｃｏｐｔｅｓ　ｓｃａｂｉｅｉ）、スジブトホコリダニ（Ｔａｒｓｏｎｅｍｕｓ　ｂｉｌｏｂａｔｕｓ）、ミツユビナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｅｖａｎｓｉ）、カンザワハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｋａｎｚａｗａｉ）、ナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｕｒｔｉｃａｅ）、ケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｐｕｔｒｅｓｃｅｎｔｉａｅ）、ホウレンソウケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｓｉｍｉｌｉｓ）、ミツバチヘギイタダニ（Ｖａｒｒｏａ　ｊａｃｏｂｓｏｎｉ）等のダニ目（Ａｃａｒｉ）害虫；
ヤマトシミ（Ｃｔｅｎｏｌｅｐｉｓｍａ　ｖｉｌｌｏｓａ）、セイヨウシミ（Ｌｅｐｉｓｍａ　ｓａｃｃｈａｒｉｎａ）等のシミ目（Ｔｈｙｓａｎｕｒａ）害虫；
セアカゴケグモ（Ｌａｔｒｏｄｅｃｔｕｓ　ｈａｓｓｅｌｔｉｉ）等のクモ目（Ａｒａｎｅａｅ）害虫；
オカダンゴムシ（Ａｒｍａｄｉｌｌｉｄｉｕｍ　ｖｕｌｇａｒｅ）等の甲殻類害虫、アフリカマイマイ（Ａｃｈａｔｉｎａ　ｆｕｌｉｃａ）、ウスカワマイマイ（Ａｃｕｓｔａ　ｄｅｓｐｅｃｔａ　ｓｉｅｂｏｌｄｉａｎａ）、ミスジマイマイ（Ｅｕｈａｄｒａ　ｐｅｌｉｏｍｐｈａｌａ）、チャコウラナメクジ（Ｌｉｍａｘ　Ｖａｌｅｎｔｉａｎａ）、ナメクジ（Ｍｅｇｈｉｍａｔｉｕｍ　ｂｉｌｉｎｅａｔｕｍ）、スクミリンゴガイ（Ｐｏｍａｃｅａ　ｃａｎａｌｉｃｕｌａｔａ）等の腹足類害虫；
イネシンガレセンチュウ（Ａｐｈｅｌｅｎｃｈｏｉｄｅｓ　ｂｅｓｓｅｙｉ）、マツノザイセンチュウ（Ｂｕｒｓａｐｈｅｌｅｎｃｈｕｓ　ｘｙｌｏｐｈｉｌｕｓ）、ナミクキセンチュウ（Ｄｉｔｙｌｅｎｃｈｕｓ　ｄｉｐｓａｃｉ）、ジャガイモシストセンチュウ（Ｇｌｏｂｏｄｅｒａ　ｒｏｓｔｏｃｈｉｅｎｓｉｓ）、ダイズシストセンチュウ（Ｈｅｔｅｒｏｄｅｒａ　ｇｌｙｃｉｎｅｓ）、ｇｕａｖａ　ｒｏｏｔ－ｋｎｏｔ　ｎｅｍａｔｏｄｅｓ　（Ｍｅｌｏｉｄｏｇｙｎｅ　ｅｎｔｅｒｏｌｏｂｉｉ）、キタネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｈａｐｌａ）、サツマイモネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｉｎｃｏｇｎｉｔａ）、ジャワネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｊａｖａｎｉｃａ）、ミナミネグサレセンチュウ（Ｐｒａｔｈｙｌｅｎｃｈｕｓ　ｃｏｆｆｅａｅ）、キタネグサレセンチュウ（Ｐｒａｔｈｙｌｅｎｃｈｕｓ　ｐｅｎｅｔｒａｎｓ）、クルミネグサレセンチュウ（Ｐｒａｔｈｙｌｅｎｃｈｕｓ　ｖｕｌｎｕｓ）、Ｐｒａｔｙｌｅｎｃｈｕｓ　ｂｒａｃｈｙｕｒｕｓ、ミナミネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｃｏｆｆｅａｅ）、ムギネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｎｅｇｌｅｃｔｕｓ）、Ｒａｄｏｐｈｏｌｕｓ　ｓｉｍｉｌｉｓ、Ｒｏｔｙｌｅｎｃｈｕｌｕｓ　ｒｅｎｉｆｏｒｍｉｓ、ミカンネセンチュウ（Ｔｙｌｅｎｃｈｕｌｕｓ　ｓｅｍｉｐｅｎｅｔｒａｎｓ）、ブドウオオハリセン（Ｘｉｐｈｉｎｅｍａ　ｉｎｄｅｘ）等の線虫類（Ｎｅｍａｔｏｄａ）害虫等が挙げられるが、本発明はこれに限定されるものではない。 The compound of the present invention is effective against pests such as insects, mites, crustaceans, spiders, centipedes and other arthropods, mollusks, nematodes, etc. Specific examples of pests are shown below, but are not limited to these.
Tea spine whitefly (Aleurocanthus camelliae), citrus spine whitefly (Aleurocanthus spiniferus), grape whitefly (Aleurolobus taonabae), Amrasca biguttula biguttula, red scale insect (Aonidiella aurantii), bean black aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), snow willow aphid (Aphis spiraecola), Arboridia apicalis, Aulacorthum solani, Balculutha saltuella, Bemisia argentifolii, Bemisia tabaci, Blissus leucopterus,
Brachycaudus helichrysi, Brevicoryne brassicae, Cacopsylla chinensis, Cacopsylla pyricola, Cacopsylla pyrisuga, Cavelerius saccharivorus, Ceratovacuna lanigera, Ceroplastes ceriferus, Ceroplastes rubens, Cimex umbellata, hemipterus), bedbugs (Cimex lectularius), narrow-horned stink bugs (Cletus punctiger), white leafhoppers (Cofana spectra), pear scale insects (Comstockaspis perniciosa), corn leaf hoppers (Dalbulus maidis), citrus whiteflies (Dialeurodes citri), citrus psyllids (Diaphorina citri), Dichelops melacanthus, spotted stink bugs (Dolycoris baccarum), giant strawberry scale insects (Drosicha corpulenta), rosy apple aphid (Dysaphis plantaginea), red spotted stink bug (Dysdercus cingulatus), potato leafhopper (Empoasca fabae), persimmon leafhopper (Empoasca nipponica), tea green leafhopper (Empoasca onukii), bean green leafhopper (Empoasca sakaii), two-striped leafhopper (Epiacanthus stramineus), apple aphid (Eriosoma lanigerum), long-horned bug (Eurydema rugosum), brown stink bug (Euschistus heros), Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis,
Fiorinia theae, Glaucias subpunctatus, Halticus insularis, Halyomorpha halys, Hyalopterus puruni, Icerya purchasi, Javanese mosquito, Laodelphax striatella, Leptocorisa acuta, Leptocorisa nigricans chinensis), Leptoglossus australis, Lipaphis erysimi, Lygus linearis, Tarnished plant bug, Macrosiphum euphorbiae, Macrosteles strifrons, Mahanarva fimbriolata, Mahanarva posticata, Melanaphis sacchari, Myzus persicae persicae), lettuce long-horned aphid (Nasonovia ribisnigri), green rice leafhopper (Nephotettix cinctinceps), black-striped green rice leafhopper (Nephotettix nigropictus), Taiwanese green rice leafhopper (Nephotettix virescens), green grass bug (Nezara antennata),
Southern green stink bug (Nezara viridula), brown planthopper (Nilaparvata lugens), Oebalus pugnax, corn planthopper (Peregrinus maidis), black horned planthopper (Perkinsiella saccharicida), eggplant mealybug (Phenacoccus solani), sable mealybug (Phenacoccus solenopsis), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera russelae), red banded stink bug (Piezodorus guildinii), striped stink bug (Piezodorus hybneri), citrus mealybug (Planococcus citri), wisteria mealybug (Planococcus kuraunhiae), brown winged green bug (Plautia crossota), citrus scale (Pseudaonidia duplex), tea scale (Pseudaonidia paeoniae), mulberry scale (Pseudaulacaspis pentagona), plum scale (Pseudaulacaspis prunicola), moth mealybug (Pseudococcus calceolariae), mulberry mealybug (Pseudococcus comstocki), long-legged mealybug (Pseudococcus longispinus), cotton freehopper (Psuedatomoscelis seriatus), pear psylla (Psylla pyrisuga), citrus cotton scale (Pulvinaria aurantii), Quesada gigas, lightning leafhopper (Recillia dorsalis), corn aphid (Rhopalosiphum maidis), wheat neck aphid (Rhopalosiphum padi), red-spotted stink bug (Rhopalus msculatus), narrow-spotted stink bug (Riptortus clavatus), Scaptocoris castanea, rice black stink bug (Scotinophora lurida), English grain aphid (Sitobion avenae)
Sogatella furcifera, Stenodema sibiricum, Stenotus rubrovittatus, Stephanitis nashi, Stephanitis pyrioides, Tagosodes orizicolus, Togo hemipterus, Toxoptera aurantii, Toxoptera citricida, Trialeurodes aphid vaporariorum), Triatoma dimidiata, Triatoma infestans, Triatoma rubrofasciata, Trigonotylus caelestialium, Trioza erytreae, Unaspis citri
Hemiptera pests such as Unaspis euonymi, Unaspis yanonensis, and Daktulosphaira Vitifoliae;
Onion moth (Acrolepiopsis sapporensis), Japanese potato moth (Acrolepiopsis suzukiella), smaller tea tortrix (Adoxophyes honmai), smaller apple tortrix (Adoxophyes orana faciata), Akebia leaf moth (Adris tyrannus), white-streaked grass moth (Aedia leucomelas), black-spotted grass moth (Agrotis ipsilon), turnip cutworm moth (Agrotis segtum), cotton leafworm (Alabama argillacea), peach leaf moth (Anarsia lineatella), velvet bean caterpillar (Anticarsia gemmatalis, Archips brevipicanus, Archips fuscocupreanus, Argyrestia conjugella, Ascotis selenaria, Autographa nigrisigna, Bucculatrix pyrivorella, Caloptilia theivora, Caloptilia zachrysa, Carposina niponensis, Carposina sasakii), dark headed stem borer (Chilo polychrysus), rice stem borer (Chilo suppressalis), tea tortrix moth (Choristoneura magnanima), rice leaf borer (Cnaphalocrocis medinalis), peach spotted moth (Conogethes punctiferalis), three-leaved goldfly (Ctenoplusia agnata), codling moth (Cydia pomonella), cotton-cutting moth (Diaphania indica), sugar cane borer (Diatraea saccharalis), corn spotted moth (Elasmopalpus lignosellus, grapeberry moss (Endopiza viteana), brown spot moth (Ephestia elutella), white striped moth (Etiella zincella), brown tussock moth (Euproctis pseudoconspersa), mulberry moth (Glyphodes pyloalis), plum fruit moth (Grapholita dimorpha), apple fruit moth (Grapholita inopinata), pear fruit moth (Grapholita molesta), potato leaf moth (Helcystogramma triannulella), cotton bollworm (Helicoverpa armigera), tobacco moth (Helicoverpa assulta), cotton ball worm (Helicoverpa zea), tobacco budworm (Heliothis virescens), gray spotted moth (Hellula undalis), tea tortrix moth (Homona magnanima), American fall webworm (Hyphantria cunea), bean fruit moth (Legumivora glycinivorella), mulberry leaf moth (Lemyra imparilis), eggplant fruit borer (Leucinodes orbonalis), coffee leaf miner (Leucoptera coffeeella), European grapevine moth (Lobesia botrana), gypsy moth (Lymantria dispar), peach leafminer moth (Lyonetia clerkella), silver leafminer moth (Lyonetia prunifoliella marinella), armyworm moth (Mamestra brassicae), tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta), bean leafworm moth (Matsumuraeses phaseoli), armyworm moth (Mythimna separata), two-banded leafminer moth (Naranga aenscens), rice case worm (Nymphula depunctalis, Olethreutes mori, Orgyia thyellina, Ostrinia furnacalis, Ostrinia nubilalis, Ostrinia scapularis, Pandemis heparana, Papilio xuthus, Parapedia teterrella, Parnara guttata, Pectinophora gossypiella, potato tuber moth (Phthorimaea operaculella), citrus leafminer moth (Phyllocnistis citrellella), golden moth moth (Phyllonorycter ringoniella), large cabbage white butterfly (Pieris brassicae), cabbage white butterfly (Pieris rapae), Indian meal moth (Plodia interpunctella), rice yellow looper moth (Plusia festucae), diamondback moth (Plutella xylostella), soybean looper (Pseudoplusia includens), one-leaf moth moth (Scirpophaga incertulas), white stem borer (Scirpophaga innotata), rice armyworm (Sesamia inferens), striped cutworm (Spodoptera depravata), southern armyworm (Spodoptera eridania), beet armyworm (Spodoptera exigua), fall armyworm (Spodoptera frugiperda), cotton leafworm (Spodoptera littoralis), common cutworm (Spodoptera litura), white cutworm (Spodoptera mauritia), pear leaf moth (Spulerrina Lepidoptera pests such as Stathmopoda masinissa, Synanthedon tenuis, Tinea translucens, Trichoplusia ni, Tuta absoluta, etc.;
Agriotes fuscicollis, Alphitobius diaperinus, Anomala cuprea, Anomala rufocuprea, Anoplophora malasiaca, Anthonomus grandis, Anthrenneus verbasci, Aromia bungii, Aulacophora femoralis, Calosobruchus chinensis), Bean Leaf Beetle (Cerotoma trifurcata), Tensite Beetle (Chaetocnema concinna), Sweet Potato Leaf Beetle (Chaetocnema confinis), Corn Free Beetle (Chaetocnema pulicaria), Red Short Flathead Beetle (Cryptolestes ferrugineus), Sweet Potato Weevil (Cylas formicarius), White-streaked Cutworm Beetle (Dermestes maculates), Banded Cucumber Beetle (Diabrotica balteata), Northern Corn Rootworm (Diabrotica barberi), Cucumber Bit Beetle (Diabrotica speciosa), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Mexican corn rootworm (Diabrotica virgifera zeae),
Rice spur beetle (Dicladispa armigera), Diloboderus abderus, rice weevil (Echinocnemus squameus), Mexican beet beetle (Epilachna varivestis), common ladybird (Epilachna varivestis), 24-spotted ladybird (Epilachna vigintioctopunctata), tobacco flea beetle (Epitrix hirtipennis), small flat-headed bamboo beetle (Epuraea domina), potato weevil (Euscepes postfasciatus), green flower beetle (Gametis jucunda), Heptophylla picea, Hypera postica, Hypothenemus hampei, Lasioderma serricorne, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lyctus brunneus,
Melanotus fortnumi, Melanotus legatus, Melanotus okinawaensis, Melanotus tamsyuensis, Migdolus fryanus, Monochamus alternatus, Oryzaephilus surinamensis, Otiorhynchus sulcatus, Oulema melanopus, Oulema sulcat ... oryzae), Paederus fuscipes, June beetle, Phyllophaga crinita, Cabbage free beetle, Phyllotereta cruciferae, Western black free beetle, Phyllotereta pusilla, Striped flea beetle, Popillia japonica, Japanese beetle, Psacothea hilaris, Eggplant longhorn beetle, Psylliodes angusticollis, Cabbage stem free beetle, chrysocephala), hop free beetle (Psylliodes punctulata), long boston beetle (Rhizopertha dominica), peach vest weevil (Rhynchites heros), granary weevil (Sitophilus granarius), rice weevil (Sitophilus oryzae), maize weevil (Sitophilus zeamais), southern cornbill bug (Sphenophorus callosus), sugar cane weevil (Sphenophorus levis), grass striped weevil (Sphenophorus venatus) Coleoptera pests such as Stegobium paniceum, Sterneczus subsignatus, Tenebrio molitor, Tomicus piniperda, Tribolium castaneum, Tribolium confusum, Trogoderma granarium, and Xylotrechus pyrrhoderus;
Frankliniella intonsa, Frankliniella occidentalis, Haplothrips aculeatus, Heliothrips haemorrhoidalis, Ponticulothrips diospyrosi, Scirtothrips dorsalis, Thrips flavus, Thrips palmi, Thrips onion thrips Thysanoptera pests such as A. tabaci;
Aedes aegypti, Aedes albopicutus, Agromyza oryzae, Anopheles albimanus, Anopheles arabiensis, Anopheles coluzzii, Anopheles darlingi, Anopheles farautii, Anopheles funestus, Anopheles gambiae, Anopheles minimus, Anopheles sinesis, Anopheles stephensi, Anopheles sundaicus, soybean pod gall fly (Asphondylia yushimai), melon fly (Bactrocera cucurbitae), oriental fruit fly (Bactrocera dorsalis), eggplant fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), Queensland fruit fly (Bactrocera tryoni), small black fungus fly (Bradisia difformis), Mediterranean fruit fly (Ceratitis capitata), giant midge (Chironomus plumosus), midge (Chironomus yoshimatsui), rice root miner (Chlorops oryzae), rice root miner (Chromatomyia horticola), Asian bush fly (Clogmia albipunctata), Culex pipiens f. molestus, Culex pipiens pallens, Culex pipiens pipiens, Culex quinquefasciatus, Culex vishnui, onion fly (Delia antique), seed fly (Delia platura), Drosophila melanogaster, Drosophila suzukii, Glossina morsitans, Glossina palpalis, Haematobia irritans,
Rice leafminer (Hydrellia griseola), Oriental rice leafminer (Hydrellia philippina), Rice leafminer (Hydrellia sasakii), Bovine fly (Hypoderma bovis), Striped bovine fly (Hypoderma lineatum), Tokunaga midge (Leptoconops nipponensis), Eggplant leafminer (Liriomyza bryoniae), Onion leafminer (Liriomyza chinensis), Tomato leafminer (Liriomyza sativae), Bean leafminer (Liriomyza trifolii), Hessian fly (Mayetiola destructor), Sheep lice fly (Melophagus ovinus), House fly (Musca domestica), Giant house fly (Muscina stabulans), Sheep fly (Oestrus ovis), Sugar beet root fly (Pegomia cunicularia), Yellow-legged fly (Prosimulium yezoensis), Apple maggot (Rhagoletis pomonella), Simulium damnosum, Reed spotted fly (Simulium japonicum), Wheat burrowing fly (Sitodiplosis Diptera pests such as Stomoxys calcitrans, Tabanus trigonus, Telantoscopus albipunctatus, Tetanops myopaeformis, Tipula aino, Tipula oleracea, and Tipula paludosa;
Apethymus kuri, Arge pagana, Athalia japonica, Athalia rosae, Atta capigua, Camponotus japonicus, Camponotus obscuripes, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti, Linepithema humile, Monomorium pharaonis), bulldog ants (Myrmecia spp.), pine sawfly (Neodiprion sertifer), Japanese paper wasp (Polistes jokahamae), fire ant (Solenopsis geminata), Japanese fire ant (Solenopsis invicta), fire ant (Solenopsis spp.), fir wasp (Urocerus gigas), small hornet (Vespa analis), giant hornet (Vespa mandarina), hairy hornet (Vespa simillima), red hornet (Vespa Hymenoptera pests such as A. velutina;
European house cricket (Acheta domestica), mole cricket (Gryllotalpa orientalis), migratory grasshopper (Locusta migratoria), two-striped grasshopper (Melanoplus bivittatus), differential grasshopper (Melanoplus differentialis), red-legged grasshopper (Melanoplus femurrubrum), migratory grasshopper (Melanoplus sanguinipes), long-winged grasshopper (Oxya japonica), common grasshopper (Oxya yezoensis), desert grasshopper (Schistocerca Orthoptera pests such as Teleogryllus emma, Teleogryllus gregaria, and Teleogryllus emma;
Collembola pests such as Bourletiella hortensis, Onychiurus folsomi, and Onychiurus sibiricus;
Oriental cockroach (Blattata orientalis), German cockroach (Blattella germanica), Formosan termite (Coptermes formosanus), Formosan termite (Coptermes guangzhouensis), Cornitermes cumulans, Taiwanese termite (Odontotermes formosanus), American cockroach (Periplaneta americana), American cockroach (Periplaneta australiae), Brown cockroach (Periplaneta brunnea), Smoky brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta Blattodea pests such as Reticulitermes amamianus, Reticulitermes kanmonensis, Reticulitermes miyatakei, and Reticulitermes speratus;
Sihonaptera pests such as dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), chicken fleas (Echidnophaga gallinacea), human fleas (Pulex irritans), sand fleas (Tunga penetrans), and rat fleas (Xenopsylla cheopis);
Bovicola bovis, sheep louse, Damalinia forficula, cat louse, Felicola subrostratus, cat louse, Haematopinus eurysternus, pig louse, Linognathus ovillus, cow louse, Linognathus vituli, Liposcelis bostrychophila, Liposcelis corrodens, Liposcelis Psocodea pests such as Liposcelis permani, Menacanthus stramineus, Menopon gallinae, Solenopotes capillatus, and Trichodectes canis;
Acapylla theavagrans, Aceria diospyri, Aceria tosichella, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Amblyomma americanum, Amblyomma maculatum, Amblyomma spp., Argas persicus, Boophilus microplus, Brevipalpus phoenis, Cheyletiella blakei, Cheyletiella yasguri, Demodex canis, Demodex cati, Demodex andersoni, Dermacenter occidentalis, Dermacenter recticulatus, Dermacenter spp., Dermacenter taiwanensis, Dermacenter variabilis, Dermanyssus gallinae, Dermatophagoides farinae, Dermatophagoides pteronyssinus, Eriophyes chibaensis, Haemaphysalis campanulata, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis longicornis, Haemaphysalis large spine megaspinosa), Ixodes holocyclus, Ixodes nipponensis, Ixodes ovatus, Ixodes pacificus, Ixodes pacificus, Ixodes persulcatus, Ixodes ricinus, Ixodes scapularis,
Chicken scabies mites (Knemidocoptes spp.), rabbit mites (Listrophorus gibbus), cat mites (Notoedres cati), mouse mites (Notoedres muris), rice red mites (Oligonychus shinkajii), house mites (Ornithonyssus bacoti), bird mites (Ornithonyssus sylviarum), ear mites (Otodectes cynotis), citrus red mites (Panonychus citri), mulberry giant mites (Panonychus mori), apple red mites (Panonychus ulmi), Chinese cabbage mite (Penthaleus erythrocephalus), wheat mite (Penthaleus major), Ryukyu citrus rust mite (Phyllocoptruta citri), citrus rust mite (Phyllocoptruta oleivora), cyclamen dust mite (Phytonemus pallidus), tea dust mite (Polyphagotarsonemus latus), horse scaly mite (Psoroptes equi), sheep scaly mite (Psoroptes ovis), cattle tick (Rhipicephalus annulatus),
Rhipicephalus appendiculatus, Rhipicephalus decoratus, Rhipicephalus sanguineus, Rhizoglyphus robini, Sarcoptes scabiei, Tarsonemus bilobatus, Tetranychus evanus, Tetranychus kanzawai, Tetranychus urticae, Tyrophagus nigricans, pests of the order Acari such as Tyrophagus putrescentiae, Tyrophagus similis, and Varroa jacobsoni;
Thysanura pests such as Ctenolepisma villosa and Lepisma saccharina;
Araneae pests such as redback spider (Latrodectus hasseltii);
Crustacean pests such as Armadillidium vulgare, gastropod pests such as Achatina fulica, Acusta despecta sieboldiana, Euhadra peliomphala, Limax valentana, Meghimatium bilineatum, and Pomacea canaliculata;
Aphelenchoides besseyi, Bursaphelenchus xylophilus, Ditylenchus dipsaci, Globodera rostochiensis, Heterodera glycines, Meloidogyne enterolobii, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne nematode ... javanica), Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus neglectus, Radopholus similis, Rotylenchus reniformis, Tylenchus semipenetrans, Xiphinema index), but the present invention is not limited thereto.
　前記有害動物は、好ましくは有害節足動物であり、より好ましくはカメムシ目害虫またはチョウ目害虫である。 The pest animal is preferably an arthropod pest, more preferably a Hemiptera pest or a Lepidoptera pest.
　本発明化合物は、水田作物、畑作物、果樹、野菜、その他の作物及び花卉等に被害を与える前記有害生物に対して顕著な防除効果を有するものであって、有害生物の発生が予測される時期に合わせて、有害生物の発生前または発生が確認された時点で、水田作物、畑作物、果樹、野菜、その他の作物、花卉等の水田水、茎葉または土壌に処理することにより本発明の有害生物防除剤としての効果が得られるものである。
　本発明化合物は、収穫物の保存中に発生する貯穀害虫等に対して顕著な防除効果を有するものである。すなわち、本発明化合物を有効成分とする有害生物防除剤を収穫物、あるいは収穫物の保存場所に、吹き付け、塗沫、塗布、浸漬、粉衣、薫蒸・薫煙または加圧注入等の収穫後（ｐｏｓｔ　ｈａｒｖｅｓｔ）処理を行えばよい。 The compound of the present invention has a remarkable control effect against the above-mentioned pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc., and the effect as the pest control agent of the present invention can be obtained by treating the paddy field water, stems, leaves, or soil of paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc. before the emergence of the pests or at the time when their emergence is confirmed, in accordance with the time when the emergence of the pests is predicted.
The compound of the present invention has a remarkable control effect against stored grain pests that occur during the storage of harvested crops, etc. That is, a pest control agent containing the compound of the present invention as an active ingredient may be applied to the harvested crops or the storage location of the harvested crops by post-harvest treatment such as spraying, smearing, coating, immersion, powder coating, fumigation, smoking, or pressurized injection.
　本発明化合物は、植物種子に適用することにより、播種後の植物に発生する農業害虫等の有害生物による被害を予防することが出来る。すなわち、本発明化合物を有効成分とする有害生物防除剤をそのまま、または水等で適宜希釈し、若しくは懸濁させた形で害虫防除に有効な量を、植物種子に対し吹き付け、塗沫、浸漬または粉衣などの処理をすることにより、本発明化合物を植物種子に接触させればよい。 The compound of the present invention, when applied to plant seeds, can prevent damage caused by pests such as agricultural pests that occur in plants after sowing. That is, the compound of the present invention can be brought into contact with the plant seeds by applying an effective amount for pest control of a pest control agent containing the compound of the present invention as an active ingredient directly or after appropriate dilution or suspension in water or the like to the plant seeds through treatment such as spraying, smearing, immersion or dusting.
　本発明化合物は、シロアリ、ヒラタキクイムシ、ナガシンクイムシ、シバンムシ、カミキリムシ等の木材食害虫に対して顕著な防除効果を有するものであり、土壌あるいは建築物等の木材に処理することにより、前記木材食害虫を防除することができる。
　本発明化合物は種々の有害生物に対して防除効果を示し、有用作物を保護する効果と共に、低薬量で殺虫剤または殺ダニ剤として優れた防除効果を示すため、環境への負荷低減に大きく貢献する効果がある。さらに、本発明化合物は、他の農園芸用殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、除草剤、植物成長調節剤、生物農薬等と混合使用することによっても優れた防除効果を奏するものである。 The compound of the present invention has a remarkable control effect against wood-eating pests such as termites, powderpost beetles, long-horn beetles, lacertilia beetles and long-horn beetles, and can control the above wood-eating pests by treating the soil or wood of buildings, etc.
The compound of the present invention shows a control effect against various pests, and has an effect of protecting useful crops, and also shows an excellent control effect as an insecticide or acaricide at a low dose, so that it has an effect of greatly contributing to reducing the burden on the environment. Furthermore, the compound of the present invention also shows an excellent control effect when used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides, etc.
　本発明化合物は、本化合物単体で使用してもよいが、好ましくは、固体担体、液体担体、気体担体、界面活性剤、固着剤、分散剤、安定剤等と混合し、粉剤、水和剤、顆粒水和剤、水溶剤、顆粒水溶剤、粒剤、乳剤、液剤、マイクロエマルション剤、水性懸濁製剤、水性乳濁製剤、サスポエマルション製剤等の組成物として使用することができる。効果が発揮される限りにおいて、それらの組成物に限定されることはない。 The compound of the present invention may be used alone, but is preferably mixed with a solid carrier, liquid carrier, gas carrier, surfactant, adhesive, dispersant, stabilizer, etc., and can be used as a composition such as a dust, hydrated powder, hydrated granule, water-soluble powder, water-soluble granule, granule, emulsion, liquid, microemulsion, aqueous suspension preparation, aqueous emulsion preparation, suspoemulsion preparation, etc. As long as the effect is exhibited, there is no limitation to these compositions.
　以下に具体的な製剤化例を示すが、これらに限定されるものではない。 Specific examples of formulations are shown below, but are not limited to these.
　本発明化合物は、本化合物単体で使用してもよいが、好ましくは、適当な固体担体または液体担体と混合し、更に所望により界面活性剤、浸透剤、展着剤、増粘剤、凍結防止剤、結合剤、固結防止剤、崩壊剤、消泡剤、防腐剤及び分解防止剤等を添加して、液剤（ｓｏｌｕｂｌｅ　ｃｏｎｃｅｎｔｒａｔｅ）、乳剤（ｅｍｕｌｓｉｆｉａｂｌｅ　ｃｏｎｃｅｎｔｒａｔｅ）、水和剤（ｗｅｔｔａｂｌｅ　ｐｏｗｄｅｒ）、水溶剤（ｗａｔｅｒ　ｓｏｌｕｂｌｅ　ｐｏｗｄｅｒ）、顆粒水和剤（ｗａｔｅｒ　ｄｉｓｐｅｒｓｉｂｌｅ　ｇｒａｎｕｌｅ）、顆粒水溶剤（ｗａｔｅｒ　ｓｏｌｕｂｌｅ　ｇｒａｎｕｌｅ）、懸濁剤（ｓｕｓｐｅｎｓｉｏｎ　ｃｏｎｃｅｎｔｒａｔｅ）、乳濁剤（ｃｏｎｃｅｎｔｒａｔｅｄ　ｅｍｕｌｓｉｏｎ）、サスポエマルジョン（ｓｕｓｐｏｅｍｕｌｓｉｏｎ）、マイクロエマルジョン（ｍｉｃｒｏｅｍｕｌｓｉｏｎ）、粉剤（ｄｕｓｔａｂｌｅ　ｐｏｗｄｅｒ）、粒剤（ｇｒａｎｕｌｅ）錠剤（ｔａｂｌｅｔ）及び乳化性ゲル剤（ｅｍｕｌｓｉｆｉａｂｌｅ　ｇｅｌ）等の任意の剤型の製剤組成物にて実用に供することができる。また、省力化及び安全性向上の観点から、上記任意の剤型の製剤を、水溶性カプセル及び水溶性フィルムの袋等の水溶性包装体に封入して供することもできる。効果が発揮される限りにおいて、それらの組成物に限定されることはない。 The compound of the present invention may be used alone, but is preferably mixed with a suitable solid or liquid carrier, and further, if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anti-caking agents, disintegrants, antifoaming agents, preservatives, anti-decomposition agents, etc. may be added to produce a liquid concentrate, an emulsifiable concentrate, a wettable powder, a water soluble powder, a water dispersible granule, etc. The composition can be used in any dosage form, such as water-soluble granules, water-soluble granules, suspension concentrates, concentrated emulsions, suspoemulsions, microemulsions, dustable powders, granules, tablets, and emulsifiable gels. From the viewpoint of labor saving and safety improvement, the above-mentioned formulations can be provided in water-soluble packaging such as water-soluble capsules and water-soluble film bags. As long as the effect is exhibited, the composition is not limited to these compositions.
　本発明で使用できる不活性担体としては固体または液体のいずれであっても良く、固体の不活性担体になりうる材料としては、例えば、ダイズ粉、穀物粉、木粉、樹皮粉、鋸粉、タバコ茎粉、クルミ殻粉、ふすま、繊維素粉末、植物エキス抽出後の残渣、粉砕合成樹脂などの合成重合体、粘土類（例えばカオリン、ベントナイト、酸性白土など）、タルク類（例えばタルク、ピロフィライドなど）、シリカ類（例えば珪藻土、珪砂、雲母、ホワイトカーボン〔含水微粉珪素、含水珪酸ともいわれる合成高分散珪酸で、製品により珪酸カルシウムを主成分として含むものもある。〕）、活性炭、イオウ粉末、軽石、焼成珪藻土、レンガ粉砕物、フライアッシュ、砂、炭酸カルシウム、リン酸カルシウムなどの無機鉱物性粉末、硫安、燐安、硝安、尿素、塩安などの化学肥料、堆肥などを挙げることができ、これらは単独、または二種類以上の混合物の形で使用される。 The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid inert carrier include soybean flour, grain flour, wood flour, bark powder, sawdust, tobacco stem powder, walnut shell powder, bran, cellulose powder, residues after plant extract extraction, synthetic polymers such as crushed synthetic resins, clays (e.g., kaolin, bentonite, acid clay, etc.), talcs (e.g., talc, pyrophyllide, etc.), silicas (e.g., diatomaceous earth, silica sand, mica, white carbon [a synthetic highly dispersed silicic acid also known as hydrous fine powder silicon or hydrous silicic acid, some products contain calcium silicate as the main component.]), activated carbon, sulfur powder, pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride, and compost, which can be used alone or in the form of a mixture of two or more types.
　液体の不活性担体になりうる材料としては、それ自体溶媒能を有するものの他、溶媒能を有さずとも補助剤の助けにより有効成分化合物を分散させうることとなるものから選択され、例えば代表例として次に上げる担体を例示できるが、これらは単独、または２種類以上の混合物の形で使用され、例えば水、アルコール類（例えば、メタノール、エタノール、イソプロパノール、ブタノール、エチレングリコールなど）、ケトン類（例えばアセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノンなど）、エーテル類（例えばジエチルエーテル、ジオキサン、セロソルブ、ジイソプロピルエーテル、テトラヒドロフランなど）、脂肪族炭化水素類（例えばケロシン、鉱油など）、芳香族炭化水素類（例えばベンゼン、トルエン、キシレン、ソルベントナフサ、アルキルナフタレンなど）、ハロゲン化炭化水素類（例えばジクロロメタン、クロロホルム、四塩化炭素、クロロベンゼンなど）、エステル類（例えば酢酸エチル、酢酸ブチル、プロピオン酸エチル、フタル酸ジイソブチル、フタル酸ジブチル、フタル酸ジオクチルなど）、アミド類（例えばジメチルホルムアミド、ジエチルホルムアミド、ジメチルアセトアミドなど）、ニトリル類（例えばアセトニトリルなど）等を挙げることができる。これら固体および液体担体は、単独で用いても２種類以上を併用してもよい。 Materials that can be liquid inert carriers are selected from those that have solvent properties themselves, as well as those that can disperse active ingredient compounds with the aid of an auxiliary even if they do not have solvent properties. For example, the following carriers can be exemplified as representative examples. These are used alone or in the form of a mixture of two or more types. For example, water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (e.g., diethyl ether, dioxane, cellosolve, diisobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), and the like. isopropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g., kerosene, mineral oil, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene, solvent naphtha, alkylnaphthalenes, etc.), halogenated hydrocarbons (e.g., dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, etc.), esters (e.g., ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (e.g., dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (e.g., acetonitrile, etc.), etc. These solid and liquid carriers may be used alone or in combination of two or more types.
　界面活性剤としては、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキル（モノまたはジ）フェニルエーテル、ポリオキシエチレン（モノ、ジまたはトリ）スチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシエチレン脂肪酸（モノまたはジ）エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ヒマシ油エチレンオキサイド付加物、アセチレングリコール、アセチレンアルコール、アセチレングリコールのエチレンオキサイド付加物、アセチレンアルコールのエチレンオキサイド付加物及びアルキルグリコシド等のノニオン性界面活性剤、アルキル硫酸エステル塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、ポリオキシエチレンアルキルエーテル硫酸またはリン酸エステル塩、ポリオキシエチレン（モノまたはジ）アルキルフェニルエーテル硫酸またはリン酸エステル塩、ポリオキシエチレン（モノ、ジまたはトリ）スチリルフェニルエーテル硫酸または燐酸エステル塩、ポリカルボン酸塩（例えば、ポリアクリル酸塩、ポリマレイン酸塩及びマレイン酸とオレフィンとの共重合物等）及びポリスチレンスルホン酸塩等のアニオン性界面活性剤、アルキルアミン塩及びアルキル４級アンモニウム塩等のカチオン性界面活性剤、アミノ酸型及びベタイン型等の両性界面活性剤、シリコーン系界面活性剤ならびにフッ素系界面活性剤が挙げられる。 Surfactants include, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono or di)phenyl ethers, polyoxyethylene (mono, di or tri)styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono or di) esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol, and nonionic surfactants such as alkyl glycosides, alkyl sulfate ester salts, alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, and the like. anionic surfactants such as phosphates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfates or phosphate ester salts, polyoxyethylene (mono- or di-) alkylphenyl ether sulfates or phosphate ester salts, polyoxyethylene (mono-, di-, or tri-) styrylphenyl ether sulfates or phosphate ester salts, polycarboxylates (e.g., polyacrylates, polymaleates, and copolymers of maleic acid and olefins, etc.) and polystyrenesulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid types and betaine types; silicone-based surfactants and fluorine-based surfactants.
　これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤１００重量部に対し、通常０．０５～２０重量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても２種類以上を併用してもよい。 The content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. These surfactants may be used alone or in combination of two or more types.
　本発明化合物を含有する組成物の施用量および施用濃度は、種々の因子、例えば目的、対象害虫、作物の生育状況、害虫の発生傾向、天候、環境条件、剤型、施用方法、施用場所、施用時期などにより変動するが、一般的に、有効成分量として、０．０００１～５０００ｐｐｍが適当であり、好ましくは、０．０１～１０００ｐｐｍの濃度で使用するのが好ましい。また、１０ａあたりの施用量は、一般に有効成分で１～３００ｇの濃度で使用するのが好ましい。また、種子処理の場合の使用量は、有効成分量として種子１ｋｇ当たり０．０００１～１０００ｇであり、好ましくは、０．００１～１００ｇである。本発明化合物を含有する組成物を植物個体への茎葉散布処理、土壌表面への散布処理、土壌中への注入処理または土壌潅注処理として使用する場合は、適当な担体に適当な濃度で希釈した後、処理を行ってもよい。本発明化合物を含有する組成物を植物種子に接触させる場合は、適当な濃度に希釈した後、植物種子に浸漬、粉衣、吹き付けまたは塗沫処理して用いてもよい。浸漬、粉衣、吹き付けまたは塗沫処理する場合の組成物使用量は、通常、有効成分量として、乾燥植物種子重量の０．０５～５０％程度であり、好ましくは、０．１～３０％が適当であるが、組成物の形態や処理対象となる植物種子の種類により適宜設定すればよく、これら範囲に限定されるものではない。 The application amount and application concentration of the composition containing the compound of the present invention vary depending on various factors, such as the purpose, the target pest, the growth condition of the crop, the tendency of the pest to occur, weather, environmental conditions, the formulation type, the application method, the application location, and the application time, but generally, an amount of 0.0001 to 5000 ppm as the active ingredient is appropriate, and it is preferable to use it at a concentration of 0.01 to 1000 ppm. Furthermore, it is generally preferable to use it at a concentration of 1 to 300 g of active ingredient per 10 a. Furthermore, the amount used in the case of seed treatment is 0.0001 to 1000 g as the active ingredient per 1 kg of seeds, and preferably 0.001 to 100 g. When the composition containing the compound of the present invention is used as a foliage spray treatment for plant individuals, a spray treatment for the soil surface, a soil injection treatment, or a soil drenching treatment, it may be diluted with an appropriate carrier at an appropriate concentration before treatment. When the composition containing the compound of the present invention is brought into contact with plant seeds, it may be diluted to an appropriate concentration and then used by immersing, coating, spraying or smearing the plant seeds. The amount of the composition used when immersing, coating, spraying or smearing is usually about 0.05 to 50% of the weight of the dry plant seeds as the amount of active ingredient, preferably 0.1 to 30%, but this may be set appropriately depending on the form of the composition and the type of plant seeds to be treated, and is not limited to these ranges.
　式（１－１）、または式（１－２）で表される本発明化合物の有効成分量は、０．１～９０重量％、好ましくは１～９０重量％、さらに好ましくは１～５０重量％、特に好ましくは３～５０重量％である。
　本発明化合物の式（１－１）、または式（１－２）で表される化合物の有効成分量は、通常粉剤では０．１～２０重量％、乳剤では５～５０重量％、水和剤では３～９０重量％、粒剤では０．１～２０重量％及びフロアブル製剤では５～９０重量％、顆粒水和剤では３～９０重量％である。一方それぞれの剤型における担体の量は、通常粉剤では６０～９９．９重量％、乳剤では４０～９５重量％、水和剤では１０～９０重量％、粒剤では８０～９９．９重量％、及びフロアブル製剤では１０～９５重量％、顆粒水和剤では１０～９０重量％である。また、補助剤の量は、通常粉剤では０．１～２０重量％、乳剤では１～２０重量％、水和剤では０．１～２０重量％、粒剤では０．１～２０重量％及びフロアブル製剤では０．１～２０重量％、顆粒水和剤では０．１～２０重量％である。 The amount of the active ingredient of the compound of the present invention represented by formula (1-1) or formula (1-2) is 0.1 to 90% by weight, preferably 1 to 90% by weight, more preferably 1 to 50% by weight, and particularly preferably 3 to 50% by weight.
The amount of the active ingredient of the compound of the present invention represented by formula (1-1) or formula (1-2) is usually 0.1-20% by weight for dusts, 5-50% by weight for emulsifiable concentrates, 3-90% by weight for wettable powders, 0.1-20% by weight for granules, 5-90% by weight for flowable formulations, and 3-90% by weight for water dispersible granules. On the other hand, the amount of the carrier in each formulation is usually 60-99.9% by weight for dusts, 40-95% by weight for emulsifiable concentrates, 10-90% by weight for wettable powders, 80-99.9% by weight for granules, 10-95% by weight for flowable formulations, and 10-90% by weight for water dispersible granules. The amount of adjuvant is usually 0.1 to 20% by weight for dusts, 1 to 20% by weight for emulsifiable concentrates, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, 0.1 to 20% by weight for flowable preparations, and 0.1 to 20% by weight for wettable powders.
　本発明化合物を含有する組成物は、必要に応じて他の農薬、例えば、殺菌剤、殺虫剤、殺ダニ剤、殺線虫剤、除草剤、生物農薬および植物成長調節剤等の農薬、核酸を有効成分とする病害防除剤（国際公開第２０１４／０６２７７５号）、土壌改良剤または肥効物質と混合して使用することができる。式（１－１）、または式（１－２）で表される本発明化合物と他の農薬を混合して使用する方法としては、式（１－１）、または式（１－２）で表される本発明化合物と他の農薬とを一つの剤型に製剤化して使用する方法、それぞれが別々の剤型に製剤化された両者を使用前に混合して使用する方法、それぞれが別々の剤型に製剤化された両者を同時に使用する方法、または、それぞれが別々の剤型に製剤化された両者について、いずれか一方を使用した後に他方を使用する方法が挙げられる。 The composition containing the compound of the present invention may be used in a mixture with other pesticides, such as fungicides, insecticides, acaricides, nematicides, herbicides, biological pesticides, and plant growth regulators, disease control agents having nucleic acids as active ingredients (WO 2014/062775), soil conditioners, or fertilizers, as necessary. Methods for using the compound of the present invention represented by formula (1-1) or formula (1-2) and other pesticides in a mixture include a method of formulating the compound of the present invention represented by formula (1-1) or formula (1-2) and other pesticides in one formulation, a method of mixing the two before use, a method of using both simultaneously, each formulated in a different formulation, or a method of using one of the two formulated in a different formulation and then using the other.
　殺虫剤に含まれる成分は以下の群ｂで示されるとおりであり、これらの塩、異性体およびＮ－オキシド体を含む。ただし、公知の殺虫剤はこれらに限定されるものではない。 The components contained in the insecticides are as shown in group b below, and include their salts, isomers and N-oxides. However, known insecticides are not limited to these.
群ｂ：
＜ｂ－１：カーバメート系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤＞
　ｂ－１：カーバメート系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤として、［ｂ－１．１］ホスホカルブ（ｐｈｏｓｐｈｏｃａｒｂ）、［ｂ－１．２］アラニカルブ（ａｌａｎｙｃａｒｂ）、［ｂ－１．３］ブトカルボキシム（ｂｕｔｏｃａｒｂｏｘｉｍ）、［ｂ－１．４］ブトキシカルボキシム（ｂｕｔｏｘｙｃａｒｂｏｘｉｍ）、［ｂ－１．５］チオジカルブ（ｔｈｉｏｄｉｃａｒｂ）、［ｂ－１．６］チオファノックス（ｔｈｉｏｆａｎｏｘ）、［ｂ－１．７］アルジカルブ（ａｌｄｉｃａｒｂ）、［ｂ－１．８］ベンダイオカルブ（ｂｅｎｄｉｏｃａｒｂ）、［ｂ－１．９］ベンフラカルブ（ｂｅｎｆｕｒａｃａｒｂ）、［ｂ－１．１０］カルバリル（ｃａｒｂａｒｙｌ）、［ｂ－１．１１］カルボフラン（ｃａｒｂｏｆｕｒａｎ）、［ｂ－１．１２］カルボスルファン（ｃａｒｂｏｓｕｌｆａｎ）、［ｂ－１．１３］エチオフェンカルブ（ｅｔｈｉｏｆｅｎｃａｒｂ）、［ｂ－１．１４］フェノブカルブ（ｆｅｎｏｂｕｃａｒｂ）、［ｂ－１．１５］ホルメタネート（ｆｏｒｍｅｔａｎａｔｅ）、［ｂ－１．１６］フラチオカルブ（ｆｕｒａｔｈｉｏｃａｒｂ）、［ｂ－１．１７］イソプロカルブ（ｉｓｏｐｒｏｃａｒｂ）、［ｂ－１．１８］メチオカルブ（ｍｅｔｈｉｏｃａｒｂ）、［ｂ－１．１９］メソミル（ｍｅｔｈｏｍｙｌ）、［ｂ－１．２０］オキサミル（ｏｘａｍｙｌ）、［ｂ－１．２１］ピリミカーブ（ｐｉｒｉｍｉｃａｒｂ）、［ｂ－１．２２］プロポキスル（ｐｒｏｐｏｘｕｒ）、［ｂ－１．２３］トリメタカルブ（ｔｒｉｍｅｔｈａｃａｒｂ）、［ｂ－１．２４］ＸＭＣ（３，５－ｘｙｌｙｌ　ｍｅｔｈｙｌｃａｒｂａｍａｔｅ）、［ｂ－１．２５］アリキシカルブ（ａｌｌｙｘｙｃａｒｂ）、［ｂ－１．２６］アルドキシカルブ（ａｌｄｏｘｙｃａｒｂ）、［ｂ－１．２７］ブフェンカルブ（ｂｕｆｅｎｃａｒｂ）、［ｂ－１．２８］ブタカルブ（ｂｕｔａｃａｒｂ）、［ｂ－１．２９］カーバノレート（ｃａｒｂａｎｏｌａｔｅ）、［ｂ－１．３０］メトルカルブ（ｍｅｔｏｌｃａｒｂ）、［ｂ－１．３１］キシルイルカルブ（ｘｙｌｙｌｃａｒｂ）、［ｂ－１．３２］フェノチオカルブ（ｆｅｎｏｔｈｉｏｃａｒｂ）等が挙げられる。 Group b:
<b-1: Carbamate Acetylcholinesterase (AChE) Inhibitor>
b-1: Carbamate acetylcholinesterase (AChE) inhibitors, such as [b-1.1] phosphocarb, [b-1.2] alanycarb, [b-1.3] butocarboxim, [b-1.4] butoxycarboxim, and [b-1.5] thiodicarb. carb), [b-1.6] thiofanox, [b-1.7] aldicarb, [b-1.8] bendiocarb, [b-1.9] benfuracarb, [b-1.10] carbaryl, [b-1.11] carbofuran, [b-1.12 ] carbosulfan, [b-1.13] ethiofencarb, [b-1.14] fenobucarb, [b-1.15] formetanate, [b-1.16] furathiocarb, [b-1.17] isoprocarb, [b -1.18] Methiocarb, [b-1.19] Methomyl, [b-1.20] Oxamyl, [b-1.21] Pirimicarb, [b-1.22] Propoxur, [b-1.23] Trimethacarb, [b-1.24] XMC (3,5-xylyl) methylcarbamate), [b-1.25] allixycarb, [b-1.26] aldoxycarb, [b-1.27] bufencarb, [b-1.28] butacarb, [b-1.29] carbanolate, [b-1.30] metolcarb, [b-1.31] xylylcarb, [b-1.32] fenothiocarb, and the like.
＜ｂ－２：有機リン系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤＞
　ｂ－２：有機リン系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤として、
［ｂ－２．１］アセフェート（ａｃｅｐｈａｔｅ）、［ｂ－２．２］アザメチホス（ａｚａｍｅｔｈｉｐｈｏｓ）、［ｂ－２．３］アジンホス－メチル（ａｚｉｎｐｈｏｓ－ｍｅｔｈｙｌ）、［ｂ－２．４］アジンホス－エチル（ａｚｉｎｐｈｏｓ－ｅｔｈｙｌ）、［ｂ－２．５］エセフォン（ｅｔｈｅｐｈｏｎ）、［ｂ－２．６］カズサホス（ｃａｄｕｓａｆｏｓ）、［ｂ－２．７］クロルエトキシホス（ｃｈｌｏｒｅｔｈｏｘｙｆｏｓ）、［ｂ－２．８］クロルフェンビンホス（ｃｈｌｏｒｆｅｎｖｉｎｐｈｏｓ）、［ｂ－２．９］クロルメホス（ｃｈｌｏｒｍｅｐｈｏｓ）、［ｂ－２．１０］クロルピリホス（ｃｈｌｏｒｐｙｒｉｆｏｓ）、［ｂ－２．１１］クロルピリホス－メチル（ｃｈｌｏｒｐｙｒｉｆｏｓ－ｍｅｔｈｙｌ）、［ｂ－２．１２］クマホス（ｃｏｕｍａｐｈｏｓ）、［ｂ－２．１３］シアノホス（ｃｙａｎｏｐｈｏｓ）、［ｂ－２．１４］デメトン－Ｓ－メチル（ｄｅｍｅｔｏｎ－Ｓ－ｍｅｔｈｙｌ）、［ｂ－２．１５］ダイアジノン（ｄｉａｚｉｎｏｎ）、［ｂ－２．１６］ジクロフェンチオン（ｄｉｃｈｌｏｆｅｎｔｈｉｏｎ）、［ｂ－２．１７］ジクロルボス（ｄｉｃｈｌｏｒｖｏｓ）、［ｂ－２．１８］ジクロトホス（ｄｉｃｒｏｔｏｐｈｏｓ）、［ｂ－２．１９］ジメトエート（ｄｉｍｅｔｈｏａｔｅ）、［ｂ－２．２０］ジメチルビンホス（ｄｉｍｅｔｈｙｌｖｉｎｐｈｏｓ）、［ｂ－２．２１］ジスルホトン（ｄｉｓｕｌｆｏｔｏｎ）、［ｂ－２．２２］Ｏ－エチル　Ｏ－４－ニトロフェニル　フェニルホスホノチオアート（Ｏ－ｅｔｈｙｌ　Ｏ－４－ｎｉｔｒｏｐｈｅｎｙｌ　ｐｈｅｎｙｌｐｈｏｓｐｈｏｎｏｔｈｉｏａｔｅ）、［ｂ－２．２３］エチオン（ｅｔｈｉｏｎ）、［ｂ－２．２４］エトプロホス（ｅｔｈｏｐｒｏｐｈｏｓ）、［ｂ－２．２５］ファムフール（ｆａｍｐｈｕｒ）、［ｂ－２．２６］フェナミホス（ｆｅｎａｍｉｐｈｏｓ）、［ｂ－２．２７］フェニトロチオン（ｆｅｎｉｔｒｏｔｈｉｏｎ）、［ｂ－２．２８］フェンチオン（ｆｅｎｔｈｉｏｎ）、［ｂ－２．２９］ホスチアゼート（ｆｏｓｔｈｉａｚａｔｅ）、［ｂ－２．３０］ヘプテノホス（ｈｅｐｔｅｎｏｐｈｏｓ）、［ｂ－２．３１］イソフェンホス－メチル（ｉｓｏｆｅｎｐｈｏｓ－ｍｅｔｈｙｌ）、
［ｂ－２．３２］イソカルボホス（Ｉｓｏｃａｒｂｏｐｈｏｓ）、［ｂ－２．３３］イソキサチオン（ｉｓｏｘａｔｈｉｏｎ）、［ｂ－２．３４］マラチオン（ｍａｌａｔｈｉｏｎ）、［ｂ－２．３５］メカルバム（ｍｅｃａｒｂａｍ）、［ｂ－２．３６］メタミドホス（ｍｅｔｈａｍｉｄｏｐｈｏｓ）、［ｂ－２．３７］メチダチオン（ｍｅｔｈｉｄａｔｈｉｏｎ）、［ｂ－２．３８］メビンホス（ｍｅｖｉｎｐｈｏｓ）、［ｂ－２．３９］モノクロトホス（ｍｏｎｏｃｒｏｔｏｐｈｏｓ）、［ｂ－２．４０］ナレッド（ｎａｌｅｄ）、［ｂ－２．４１］オメトエート（ｏｍｅｔｈｏａｔｅ）、［ｂ－２．４２］オキシデメトン－メチル（ｏｘｙｄｅｍｅｔｏｎ－ｍｅｔｈｙｌ）、［ｂ－２．４３］パラチオン（ｐａｒａｔｈｉｏｎｓ）、［ｂ－２．４４］パラチオン－メチル（ｐａｒａｔｈｉｏｎ－ｍｅｔｈｙｌ）、［ｂ－２．４５］フェントエート（ｐｈｅｎｔｈｏａｔｅ）、［ｂ－２．４６］ホレート（ｐｈｏｒａｔｅ）、［ｂ－２．４７］ホサロン（ｐｈｏｓａｌｏｎｅ）、［ｂ－２．４８］ホスメット（ｐｈｏｓｍｅｔ）、［ｂ－２．４９］ホスファミドン（ｐｈｏｓｐｈａｍｉｄｏｎ）、［ｂ－２．５０］ホキシム（ｐｈｏｘｉｍ）、［ｂ－２．５１］ピリミホス－メチル（ｐｉｒｉｍｉｐｈｏｓ－ｍｅｔｈｙｌ）、［ｂ－２．５２］プロフェノホス（ｐｒｏｆｅｎｏｆｏｓ）、［ｂ－２．５３］プロペタンホス（ｐｒｏｐｅｔａｍｐｈｏｓ）、［ｂ－２．５４］プロチオホス（ｐｒｏｔｈｉｏｆｏｓ）、［ｂ－２．５５］ピラクロホス（ｐｙｒａｃｌｏｆｏｓ）、［ｂ－２．５６］ピリダフェンチオン（ｐｙｒｉｄａｐｈｅｎｔｈｉｏｎ）、［ｂ－２．５７］キナルホス（ｑｕｉｎａｌｐｈｏｓ）、［ｂ－２．５８］スルホテップ（ｓｕｌｆｏｔｅｐ）、［ｂ－２．５９］テブピリムホス（ｔｅｂｕｐｉｒｉｍｆｏｓ）、［ｂ－２．６０］テメホス（ｔｅｍｅｐｈｏｓ）、［ｂ－２．６１］テルブホス（ｔｅｒｂｕｆｏｓ）、［ｂ－２．６２］チオメトン（ｔｈｉｏｍｅｔｏｎ）、［ｂ－２．６３］トリアゾホス（ｔｒｉａｚｏｐｈｏｓ）、［ｂ－２．６４］トリクロルホン（ｔｒｉｃｈｌｏｒｆｏｎ）、［ｂ－２．６５］バミドチオン（ｖａｍｉｄｏｔｈｉｏｎ）、［ｂ－２．６６］クロルチオン（ｃｈｌｏｒｏｔｈｉｏｎ）、［ｂ－２．６７］ブロムフェンビンホス（ｂｒｏｍｆｅｎｖｉｎｆｏｓ）、
［ｂ－２．６８］ブロモホス（ｂｒｏｍｏｐｈｏｓ）、［ｂ－２．６９］ブロモホス－エチル（ｂｒｏｍｏｐｈｏｓ－ｅｔｈｙｌ）、［ｂ－２．７０］ブタチオホス（ｂｕｔａｔｈｉｏｆｏｓ）、［ｂ－２．７１］カルボフェノチオン（ｃａｒｂｏｐｈｅｎｏｔｈｉｏｎ）、［ｂ－２．７２］クロルホキシム（ｃｈｌｏｒｐｈｏｘｉｍ）、［ｂ－２．７３］スルプロホス（ｓｕｌｐｒｏｆｏｓ）、［ｂ－２．７４］ジアミダホス（ｄｉａｍｉｄａｆｏｓ）、［ｂ－２．７５］テトラクロルビンホス（ｔｅｔｒａｃｈｌｏｒｖｉｎｐｈｏｓ）、［ｂ－２．７６］プロパホス（ｐｒｏｐａｐｈｏｓ）、［ｂ－２．７７］メスルフェンホス（ｍｅｓｕｌｆｅｎｆｏｓ）、［ｂ－２．７８］ジオキサベンゾホス（ｄｉｏｘａｂｅｎｚｏｆｏｓ）、［ｂ－２．７９］エトリムホス（ｅｔｒｉｍｆｏｓ）、［ｂ－２．８０］オキシデプロホス（ｏｘｙｄｅｐｒｏｆｏｓ）、［ｂ－２．８１］ホルモチオン（ｆｏｒｍｏｔｈｉｏｎ）、［ｂ－２．８２］フェンスルホチオン（ｆｅｎｓｕｌｆｏｔｈｉｏｎ）、［ｂ－２．８３］イサゾホス（ｉｓａｚｏｆｏｓ）、［ｂ－２．８４］イミシアホス（ｉｍｉｃｙａｆｏｓ）、［ｂ－２．８５］イサミドホス（ｉｓａｍｉｄｏｆｏｓ）、［ｂ－２．８６］チオナジン（ｔｈｉｏｎａｚｉｎ）、［ｂ－２．８７］ホスチエタン（ｆｏｓｔｈｉｅｔａｎ）等が挙げられる。 <b-2: Organophosphorus acetylcholinesterase (AChE) inhibitors>
b-2: As an organophosphorus acetylcholinesterase (AChE) inhibitor,
[b-2.1] acephate, [b-2.2] azamethiphos, [b-2.3] azinphos-methyl, [b-2.4] azinphos-ethyl, [b-2.5] ethephon, [b-2.6] cadusafos usafos), [b-2.7] chlorethoxyphos, [b-2.8] chlorfenvinphos, [b-2.9] chlormephos, [b-2.10] chlorpyrifos, [b-2.11] chlorpyrifos-methyl pyrifos-methyl, [b-2.12] coumaphos, [b-2.13] cyanophos, [b-2.14] demeton-S-methyl, [b-2.15] diazinon, [b-2.16] diclofenthion n), [b-2.17] dichlorvos, [b-2.18] dicrotophos, [b-2.19] dimethoate, [b-2.20] dimethylvinphos, [b-2.21] disulfoton, [b-2.22] O-ethyl O-4-nitrophenyl phenylphosphonothioate phenylphosphonothioate), [b-2.23] ethion, [b-2.24] ethoprophos, [b-2.25] famphur, [b-2.26] fenamiphos, [b-2.27] fenitrothion, [b-2.28] fenthion, [b-2.29] fosthiazate, [b-2.30] heptenophos, [b-2.31] isofenphos-methyl,
[b-2.32] Isocarbophos, [b-2.33] Isoxathion, [b-2.34] Malathion, [b-2.35] Mecarbam, [b-2.36] Methamidophos, [b-2.37] Methidathion, [b-2.38] Mevinphos, [b-2.39] Monocrotophos, [b-2.40] Naled, [b-2.41] Omethoate, [b-2.42] oxydemeton-methyl, [b-2.43] parathion, [b-2.44] parathion-methyl, [b-2.45] phenthoate, [b-2.46] phorate, [b-2.47] phosalone, [b-2.48] phosmet, [b-2.49] phosphamidon, [b-2 .50] phoxim, [b-2.51] pirimiphos-methyl, [b-2.52] profenofos, [b-2.53] propetamphos, [b-2.54] prothiofos, [b-2.55] pyraclofos, [b-2.56] pyridaphenthion, [b-2.57] quinalphos, [b-2.58] sulfotep ), [b-2.59] tebupirimfos, [b-2.60] temephos, [b-2.61] terbufos, [b-2.62] thiometon, [b-2.63] triazophos, [b-2.64] trichlorfon, [b-2.65] vamidothion, [b-2.66] chlorthion, [b-2.67] bromfenvinfos,
[b-2.68] bromophos, [b-2.69] bromophos-ethyl, [b-2.70] butathiophos, [b-2.71] carbophenothion, [b-2.72] chlorphoxim, [b-2.73] sulprofos, [b-2.74] diamidaphos, [b-2.75] tetrachlorvinphos, [b-2.76] propaphos, [b-2.77] mesulfenphos enfos), [b-2.78] dioxabenzophos (dioxabenzofos), [b-2.79] etrimfos (etrimfos), [b-2.80] oxydeprofos (oxydeprofos), [b-2.81] formothion (formothion), [b-2.82] fensulfothion (fensulfothion), [b-2.83] isazofos (isazofos), [b-2.84] imicyafos (imichyafos), [b-2.85] isamidofos (isamidofos), [b-2.86] thionazine (thionazin), [b-2.87] fostietan (fosthietan), and the like.
＜ｂ－３：環状ジエン有機塩素系ＧＡＢＡ作動性塩化物イオンチャネルブロッカー＞
　ｂ－３：環状ジエン有機塩素系ＧＡＢＡ作動性塩化物イオンチャネルブロッカーとして、［ｂ－３．１］クロルデン（ｃｈｌｏｒｄａｎｅ）、［ｂ－３．２］エンドスルファン（ｅｎｄｏｓｕｌｆａｎ）、［ｂ－３．３］リンデン（ｌｉｎｄａｎｅ）、［ｂ－３．４］ジエノクロル（ｄｉｅｎｏｃｈｌｏｒ）等が挙げられる。 <b-3: Cyclic diene organochlorine GABAergic chloride ion channel blocker>
b-3: Cyclic diene organochlorine GABA-activated chloride ion channel blockers include [b-3.1] chlordane, [b-3.2] endosulfan, [b-3.3] lindane, and [b-3.4] dienochlor.
＜ｂ－４：フェニルピラゾール系ＧＡＢＡ作動性塩化物イオンチャネルブロッカー＞
　ｂ－４：フェニルピラゾール系ＧＡＢＡ作動性塩化物イオンチャネルブロッカーとして、［ｂ－４．１］エチプロール（ｅｔｈｉｐｒｏｌｅ）、［ｂ－４．２］フィプロニル（ｆｉｐｒｏｎｉｌ）、［ｂ－４．３］アセトプロール（ａｃｅｔｏｐｒｏｌｅ）等が挙げられる。 <b-4: Phenylpyrazole GABA-gated chloride ion channel blockers>
b-4: Phenylpyrazole GABA-activated chloride ion channel blockers include, for example, [b-4.1] ethiprole, [b-4.2] fipronil, and [b-4.3] acetoprole.
＜ｂ－５：ナトリウムチャネルモジュレーター＞
　ｂ－５：ナトリウムチャネルモジュレーターとして、［ｂ－５．１］アクリナトリン（ａｃｒｉｎａｔｈｒｉｎ）、［ｂ－５．２］アレスリン（ａｌｌｅｔｈｒｉｎ）、［ｂ－５．３］ビフェントリン（ｂｉｆｅｎｔｈｒｉｎ）、［ｂ－５．４］ビオアレスリン（ｂｉｏａｌｌｅｔｈｒｉｎ）、［ｂ－５．５］ビオアレスリン　Ｓ－シクロペンテニル　アイソマー（ｂｉｏａｌｌｅｔｈｒｉｎ　Ｓ－ｃｙｃｌｏｐｅｎｔｅｎｙｌ　ｉｓｏｍｅｒ）、［ｂ－５．６］ビオレスメトリン（ｂｉｏｒｅｓｍｅｔｈｒｉｎ）、［ｂ－５．７］シクロプロトリン（ｃｙｃｌｏｐｒｏｔｈｒｉｎ）、［ｂ－５．８］シフルトリン（ｃｙｆｌｕｔｈｒｉｎ）、［ｂ－５．９］ベータ－シフルトリン（ｂｅｔａ－ｃｙｆｌｕｔｈｒｉｎ）、［ｂ－５．１０］シハロトリン（ｃｙｈａｌｏｔｈｒｉｎ）、［ｂ－５．１１］ガンマ－シハロトリン（ｇａｍｍａ－ｃｙｈａｌｏｔｈｒｉｎ）、［ｂ－５．１２］ラムダ－シハロトリン（ｌａｍｂｄａ－ｃｙｈａｌｏｔｈｒｉｎ）、［ｂ－５．１３］シペルメトリン（ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．１４］アルファ－シペルメトリン（ａｌｐｈａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．１５］ベータ－シペルメトリン（ｂｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．１６］セタ－シペルメトリン（ｔｈｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．１７］ゼダ－シペルメトリン（ｚｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．１８］シフェノトリン（ｃｙｐｈｅｎｏｔｈｒｉｎ［（１Ｒ）－ｔｒａｎｓ－ｉｓｏｍｅｒ］）、［ｂ－５．１９］デルタメトリン（ｄｅｌｔａｍｅｔｈｒｉｎ）、［ｂ－５．２０］エンペントリン（ｅｍｐｅｎｔｈｒｉｎ［（ＥＺ）－（１Ｒ）－ｉｓｏｍｅｒ］）、［ｂ－５．２１］エスフェンバレレート（ｅｓｆｅｎｖａｌｅｒａｔｅ）、［ｂ－５．２２］エトフェンプロックス（ｅｔｈｏｆｅｎｐｒｏｘ）、［ｂ－５．２３］フェンプロパトリン（ｆｅｎｐｒｏｐａｔｈｒｉｎ）、［ｂ－５．２４］フェンバレレート（ｆｅｎｖａｌｅｒａｔｅ）、［ｂ－５．２５］フルシトリネート（ｆｌｕｃｙｔｈｒｉｎａｔｅ）、［ｂ－５．２６］フルメトリン（ｆｌｕｍｅｔｈｒｉｎ）、［ｂ－５．２７］タウ－フルバリネート（ｔａｕ－ｆｌｕｖａｌｉｎａｔｅ）、［ｂ－５．２８］ハルフェンプロックス（ｈａｌｆｅｎｐｒｏｘ）、［ｂ－５．２９］イミプロトリン（ｉｍｉｐｒｏｔｈｒｉｎ）、［ｂ－５．３０］メトトリン（ｍｅｔｈｏｔｈｒｉｎ）、［ｂ－５．３１］メトフルトリン（ｍｅｔｏｆｌｕｔｈｒｉｎ）、［ｂ－５．３２］イプシロン－メトフルトリン（ｅｐｓｉｌｏｎ－ｍｅｔｏｆｌｕｔｈｒｉｎ）、［ｂ－５．３３］モンフルオロトリン（ｍｏｍｆｌｕｏｒｏｔｈｒｉｎ）、
［ｂ－５．３４］イプシロン－モンフルオロトリン（ｅｐｓｉｌｏｎ－ｍｏｍｆｌｕｏｒｏｔｈｒｉｎ）、［ｂ－５．３５］ペルメトリン（ｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．３６］フェノトリン（ｐｈｅｎｏｔｈｒｉｎ［（１Ｒ）－ｔｒａｎｓ－ｉｓｏｍｅｒ］）、［ｂ－５．３７］プラレトリン（ｐｒａｌｌｅｔｈｒｉｎ）、［ｂ－５．３８］ピレトリン（Ｐｙｒｅｔｈｒｉｎ）、［ｂ－５．３９］レスメトリン（ｒｅｓｍｅｔｈｒｉｎ）、［ｂ－５．４０］カデトリン（ｋａｄｅｔｈｒｉｎ）、［ｂ－５．４１］シラフルオフェン（ｓｉｌａｆｌｕｏｆｅｎ）、［ｂ－５．４２］テフルトリン（ｔｅｆｌｕｔｈｒｉｎ）、［ｂ－５．４３］テトラメトリン（ｔｅｔｒａｍｅｔｈｒｉｎ）、［ｂ－５．４４］テトラメトリン（ｔｅｔｒａｍｅｔｈｒｉｎ［（１Ｒ）－ｉｓｏｍｅｒ］）、［ｂ－５．４５］トラロメトリン（ｔｒａｌｏｍｅｔｈｒｉｎ）、［ｂ－５．４６］トランスフルトリン（ｔｒａｎｓｆｌｕｔｈｒｉｎ）、［ｂ－５．４７］ＺＸＩ８９０１（３－（４－ｂｒｏｍｏｐｈｅｎｏｘｙ）ｐｈｅｎｙｌ］－ｃｙａｎｏｍｅｔｈｙｌ　４－（ｄｉｆｌｕｏｒｏｍｅｔｈｏｘｙ）－α－（１－ｍｅｔｈｙｌｅｔｈｙｌ）ｂｅｎｚｅｎｅａｃｅｔａｔｅ）、［ｂ－５．４８］バイオペルメトリン（ｂｉｏｐｅｒｍｅｔｈｒｉｎ）、［ｂ－５．４９］フラメトリン（ｆｕｒａｍｅｔｈｒｉｎ）、［ｂ－５．５０］プロフルトリン（ｐｒｏｆｌｕｔｈｒｉｎ）、［ｂ－５．５１］フルブロシトリネート（ｆｌｕｂｒｏｃｙｔｈｒｉｎａｔｅ）、［ｂ－５．５２］ジメフルトリン（ｄｉｍｅｆｌｕｔｈｒｉｎ）、［ｂ－５．５３］フェノトリン（ｐｈｅｎｏｔｈｒｉｎ）、［ｂ－５．５４］フルバリネート（ｆｌｕｖａｌｉｎａｔｅ）、［ｂ－５．５５］ＤＤＴ（ｄｉｃｈｌｏｒｏ－ｄｉｐｈｅｎｙｌ－ｔｒｉｃｈｌｏｒｏｅｔｈａｎｅ）、［ｂ－５．５６］メトキシクロル（ｍｅｔｈｏｘｙｃｈｌｏｒ）等が挙げられる。 <b-5: sodium channel modulator>
b-5: sodium channel modulators, including [b-5.1] acrinathrin, [b-5.2] allethrin, [b-5.3] bifenthrin, [b-5.4] bioallethrin, and [b-5.5] bioallethrin S-cyclopentenyl isomer. isomer), [b-5.6] bioresmethrin, [b-5.7] cycloprothrin, [b-5.8] cyfluthrin, [b-5.9] beta-cyfluthrin, [b-5.10] cyhalothrin, [b-5.11] gamma-cyhalothrin, [b-5.12] lambda-cyhalothrin, [b-5. 13] cypermethrin, [b-5.14] alpha-cypermethrin, [b-5.15] beta-cypermethrin, [b-5.16] theta-cypermethrin, [b-5.17] zeta-cypermethrin, [b-5.18] cyphenothrin [(1R)-trans-isomer], [b-5.19] delta Methrin (deltamethrin), [b-5.20] empenthrin ((EZ)-(1R)-isomer]), [b-5.21] esfenvalerate (esfenvalerate), [b-5.22] etofenprox (ethofenprox), [b-5.23] fenpropathrin (fenpropathrin), [b-5.24] fenvalerate (fenvalerate), [b-5.25] flucythrinate (flucythrinate), [b-5.26] flumethrin ( flumethrin), [b-5.27] tau-fluvalinate, [b-5.28] halfenprox, [b-5.29] imiprothrin, [b-5.30] methothrin, [b-5.31] metofluthrin, [b-5.32] epsilon-metofluthrin, [b-5.33] momfluorothrin,
[b-5.34] epsilon-momfluorothrin, [b-5.35] permethrin, [b-5.36] phenothrin [(1R)-trans-isomer], [b-5.37] prallethrin, [b-5.38] pyrethrin, [b-5.39] resmethrin, [b-5.40] kadethrin, [b-5.41] sira Fluofen, [b-5.42] tefluthrin, [b-5.43] tetramethrin, [b-5.44] tetramethrin [(1R)-isomer], [b-5.45] tralomethrin, [b-5.46] transfluthrin, [b-5.47] ZXI8901 (3-(4-bromophenoxy)phenyl]-cyanomethyl 4-(difluoromethoxy)-α-(1-methylethyl)benzeneacetate), [b-5.48] biopermethrin, [b-5.49] furamethrin, [b-5.50] profluthrin, [b-5.51] flubrocythrinate ate), [b-5.52] dimefluthrin, [b-5.53] fenothrin, [b-5.54] fluvalinate, [b-5.55] DDT (dichloro-diphenyl-trichloroethane), [b-5.56] methoxychlor, and the like.
＜ｂ－６：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）競合的モジュレーター＞
　ｂ－６：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）競合的モジュレーターとして、［ｂ－６．１］アセタミプリド（ａｃｅｔａｍｉｐｒｉｄ）、［ｂ－６．２］クロチアニジン（ｃｌｏｔｈｉａｎｉｄｉｎ）、［ｂ－６．３］ジノテフラン（ｄｉｎｏｔｅｆｕｒａｎ）、［ｂ－６．４］イミダクロプリド（ｉｍｉｄａｃｌｏｐｒｉｄ）、［ｂ－６．５］ニテンピラム（ｎｉｔｅｎｐｙｒａｍ）、［ｂ－６．６］チアクロプリド（ｔｈｉａｃｌｏｐｒｉｄ）、［ｂ－６．７］チアメトキサム（ｔｈｉａｍｅｔｈｏｘａｍ）、［ｂ－６．８］ニコチン（ｎｉｃｏｔｉｎｅ）、［ｂ－６．９］硫酸ニコチン（ｎｉｃｏｔｉｎｅ　ｓｕｌｆａｔｅ）、［ｂ－６．１０］スルホキサフロル（ｓｕｌｆｏｘａｆｌｏｒ）、［ｂ－６．１１］フルピラジフロン（ｆｌｕｐｙｒａｄｉｆｕｒｏｎｅ）、［ｂ－６．１２］トリフルメゾピリム（ｔｒｉｆｌｕｍｅｚｏｐｙｒｉｍ）等が挙げられる。 <b-6: Nicotinic acetylcholine receptor (nAChR) competitive modulator>
b-6: Nicotinic acetylcholine receptor (nAChR) competitive modulators, including: [b-6.1] acetamiprid, [b-6.2] clothianidin, [b-6.3] dinotefuran, [b-6.4] imidacloprid, [b-6.5] nitenpyram, [b-6.6] thiacloprid, [b-6.7] thiamethoxam, [b-6.8] nicotine, [b-6.9] nicotine sulfate sulfate), [b-6.10] sulfoxaflor, [b-6.11] flupyradifurone, [b-6.12] triflumezopyrim, and the like.
＜ｂ－７：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）アロステリックモジュレーター－部位Ｉ＞
　ｂ－７：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）アロステリックモジュレーター－部位Ｉとして、［ｂ－７．１］スピノサド（ｓｐｉｎｏｓａｄ）、［ｂ－７．２］スピネトラム（ｓｐｉｎｅｔｏｒａｍ）等が挙げられる。 <b-7: Nicotinic acetylcholine receptor (nAChR) allosteric modulator - site I>
b-7: Nicotinic acetylcholine receptor (nAChR) allosteric modulators - site I include [b-7.1] spinosad, [b-7.2] spinetoram, and the like.
＜ｂ－８：グルタミン酸作動性塩素イオンチャネル（ＧｌｕＣｌ）　アロステリックモジュレーター＞
　ｂ－８：グルタミン酸作動性塩素イオンチャネル（ＧｌｕＣｌ）　アロステリックモジュレーターとして、［ｂ－８．１］アバメクチン（ａｂａｍｅｃｔｉｎ）、［ｂ－８．２］エマメクチン安息香酸塩（ｅｍａｍｅｃｔｉｎ　ｂｅｎｚｏａｔｅ）、［ｂ－８．３］レピメクチン（ｌｅｐｉｍｅｃｔｉｎ）、［ｂ－８．４］ミルベメクチン（ｍｉｌｂｅｍｅｃｔｉｎ）等が挙げられる。 <b-8: Glutamate-gated chloride channel (GluCl) allosteric modulator>
b-8: Glutamate-gated chloride ion channel (GluCl) Allosteric modulators include [b-8.1] abamectin, [b-8.2] emamectin benzoate, [b-8.3] lepimectin, [b-8.4] milbemectin, and the like.
＜ｂ－９：幼若ホルモン類似剤＞
　ｂ－９：幼若ホルモン類似剤として、［ｂ－９．１］ヒドロプレン（ｈｙｄｒｏｐｒｅｎｅ）、［ｂ－９．２］キノプレン（ｋｉｎｏｐｒｅｎｅ）、［ｂ－９．３］メトプレン（ｍｅｔｈｏｐｒｅｎｅ）、［ｂ－９．４］フェノキシカルブ（ｆｅｎｏｘｙｃａｒｂ）、［ｂ－９．５］ピリプロキシフェン（ｐｙｒｉｐｒｏｘｙｆｅｎ）等が挙げられる。 <B-9: Juvenile hormone analogues>
b-9: Juvenile hormone analogues include, for example, [b-9.1] hydroprene, [b-9.2] kinoprene, [b-9.3] methoprene, [b-9.4] fenoxycarb, and [b-9.5] pyriproxyfen.
＜ｂ－１０：その他の非特異的(マルチサイト)阻害剤＞
　ｂ－１０：その他の非特異的(マルチサイト)阻害剤として、［ｂ－１０．１］臭化メチル（ｍｅｔｈｙｌ　ｂｒｏｍｉｄｅ）、［ｂ－１０．２］クロルピクリン（ｃｈｌｏｒｏｐｉｃｒｉｎ）、［ｂ－１０．３］クリオライト（ｃｒｙｏｌｉｔｅ）、［ｂ－１０．４］フッ化スルフリル（ｓｕｌｆｕｒｙｌ　ｆｌｕｏｒｉｄｅ）、［ｂ－１０．５］ホウ砂（ｂｏｒａｘ）、［ｂ－１０．６］ホウ酸（ｂｏｒｉｃ　ａｃｉｄ）、［ｂ－１０．７］オクタホウ酸ニナトリウム塩（ｄｉｓｏｄｉｕｍ　ｏｃｔａｂｏｒａｔｅ）、［ｂ－１０．８］メタホウ酸ナトリウム塩（ｓｏｄｉｕｍ　ｍｅｔａｂｏｒａｔｅ）、［ｂ－１０．９］吐酒石、［ｂ－１０．１０］ダゾメット（ｄａｚｏｍｅｔ）、［ｂ－１０．１１］メタム（ｍｅｔａｍ）、［ｂ－１０．１２］カーバムナトリウム塩（ｍｅｔｈａｍ　ｓｏｄｉｕｍ）等が挙げられる。 <b-10: Other non-specific (multi-site) inhibitors>
b-10: Other non-specific (multi-site) inhibitors include: [b-10.1] methyl bromide, [b-10.2] chloropicrin, [b-10.3] cryolite, [b-10.4] sulfuryl fluoride, [b-10.5] borax, [b-10.6] boric acid, [b-10.7] disodium octaborate, [b-10.8] sodium metaborate [b-10.10] dazomet, [b-10.11] metam, [b-10.12] carbam sodium salt, and the like.
＜ｂ－１１：弦音器官ＴＲＰＶチャネルモジュレーター＞
　ｂ－１１：弦音器官ＴＲＰＶチャネルモジュレーターとして、［ｂ－１１．１］ピメトロジン（ｐｙｍｅｔｒｏｚｉｎｅ）、［ｂ－１１．２］ピリフルキナゾン（ｐｙｒｉｆｌｕｑｕｉｎａｚｏｎ）、［ｂ－１１．３］アフィドピロペン（Ａｆｉｄｏｐｙｒｏｐｅｎ）等が挙げられる。 <b-11: Chordotonal organ TRPV channel modulator>
b-11: Chordotonal organ TRPV channel modulators include, for example, [b-11.1] pymetrozine, [b-11.2] pyrifluquinazon, [b-11.3] afidopyropene, and the like.
＜ｂ－１２：ＣＨＳ１に作用するダニ類成長阻害剤＞
　ｂ－１２：ＣＨＳ１に作用するダニ類成長阻害剤として、［ｂ－１２．１］クロフェンテジン（ｃｌｏｆｅｎｔｅｚｉｎｅ）、［ｂ－１２．２］ジフロビダジン（ｄｉｆｌｏｖｉｄａｚｉｎ）、［ｂ－１２．３］ヘキシチアゾクス（ｈｅｘｙｔｈｉａｚｏｘ）、［ｂ－１２．４］エトキサゾール（ｅｔｏｘａｚｏｌｅ）等が挙げられる。 <b-12: Mite growth inhibitor acting on CHS1>
b-12: Examples of mite growth inhibitors acting on CHS1 include [b-12.1] clofentezine, [b-12.2] diflovidazin, [b-12.3] hexythiazox, and [b-12.4] etoxazole.
＜ｂ－１３：微生物由来昆虫中腸膜破壊剤＞
　ｂ－１３：微生物由来昆虫中腸膜破壊剤として、［ｂ－１３．１］バチルス　チューリンゲンシス（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ）、［ｂ－１３．２］Ｂ．ｔ．イスラエンシス（Ｂ．ｔ．　ｓｕｂｓｐ．　Ｉｓｒａｅｌｅｎｓｉｓ）、［ｂ－１３．３］Ｂ．ｔ．アイザワイ（Ｂ．ｔ．　ｓｕｂｓｐ．　Ａｉｚａｗａｉ）、［ｂ－１３．４］Ｂ．ｔ．クルスタキー（Ｂ．ｔ．　ｓｕｂｓｐ．　ｋｕｒｓｔａｋｉ）、［ｂ－１３．５］Ｂ．ｔ．テネブリオニス（Ｂ．ｔ．　ｓｕｂｓｐ．　ｔｅｎｅｂｒｉｏｎｉｓ）、［ｂ－１３．６］Ｂｔ作物に含まれるたんぱく質：Ｃｒｙ１Ａｂ，　Ｃｒｙ１Ａｃ，　Ｃｒｙ１Ｆａ，　Ｃｒｙ１Ａ．１０５，　Ｃｒｙ２Ａｂ，　Ｖｉｐ３Ａ，ｍＣｒｙ３Ａ，　Ｃｒｙ３Ａｂ，　Ｃｒｙ　３Ｂｂ，　Ｃｒｙ３４Ａｂ１／Ｃｒｙ３５Ａｂ１（Ｂ．ｔ．　ｃｒｏｐ　ｐｒｏｔｅｉｎｓ：Ｃｒｙ１Ａｂ，　Ｃｒｙ１Ａｃ，　Ｃｒｙ１Ｆａ，　Ｃｒｙ１Ａ．１０５，　Ｃｒｙ２Ａｂ，　Ｖｉｐ３Ａ，ｍＣｒｙ３Ａ，　Ｃｒｙ３Ａｂ，　Ｃｒｙ　３Ｂｂ，　Ｃｒｙ３４Ａｂ１／Ｃｒｙ３５Ａｂ１）、［ｂ－１３．７］バチルス　スファエリクス（Ｂａｃｉｌｌｕｓ　ｓｐｈａｅｒｉｃｕｓ）等が挙げられる。 <b-13: Microorganism-derived insect midgut membrane disrupting agent>
b-13: As microbial insect midgut membrane disrupting agents, [b-13.1] Bacillus thuringiensis, [b-13.2] B. t. israensis, [b-13.3] B. t. aizawai, [b-13.4] B. t. kurstaki, [b-13.5] B. t. tenebrionis, [b-13.6] Proteins contained in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A. 105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry 3Bb, Cry34Ab1/Cry35Ab1 (B.t. crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry 3Bb, Cry34Ab1/Cry35Ab1), [b-13.7] Bacillus sphaericus, and the like.
＜ｂ－１４：ミトコンドリアＡＴＰ合成酵素阻害剤＞
　ｂ－１４：ミトコンドリアＡＴＰ合成酵素阻害剤として、［ｂ－１４．１］ジアフェンチウロン（ｄｉａｆｅｎｔｈｉｕｒｏｎ）、［ｂ－１４．２］アゾシクロチン（ａｚｏｃｙｃｌｏｔｉｎ）、［ｂ－１４．３］シヘキサチン（ｃｙｈｅｘａｔｉｎ）、［ｂ－１４．４］フェンブタチンオキシド（ｆｅｎｂｕｔａｔｉｎ　ｏｘｉｄｅ）、［ｂ－１４．５］プロパルギット（ｐｒｏｐａｒｇｉｔｅ）、［ｂ－１４．６］テトラジホン（ｔｅｔｒａｄｉｆｏｎ）等が挙げられる。 <b-14: Mitochondrial ATP synthase inhibitor>
b-14: Mitochondrial ATP synthase inhibitors include, for example, [b-14.1] diafenthiuron, [b-14.2] azocyclotin, [b-14.3] cyhexatin, [b-14.4] fenbutatin oxide, [b-14.5] propargite, and [b-14.6] tetradifon.
＜ｂ－１５：プロトン勾配を撹乱する酸化的リン酸化脱共役剤＞
　ｂ－１５：プロトン勾配を撹乱する酸化的リン酸化脱共役剤として、
［ｂ－１５．１］クロルフェナピル（ｃｈｌｏｒｆｅｎａｐｙｌ）、［ｂ－１５．２］ＤＮＯＣ（ｄｉｎｉｔｒｏ－ｏｒｔｈｏ－ｃｒｅｓｏｌ）、［ｂ－１５．３］ビナパクリル（ｂｉｎａｐａｃｒｙｌ）、［ｂ－１５．４］スルフルラミド（ｓｕｌｆｌｕｒａｍｉｄ）、 <b-15: Oxidative phosphorylation uncouplers that disrupt the proton gradient>
b-15: as an oxidative phosphorylation uncoupler that disrupts the proton gradient;
[b-15.1] chlorfenapyr, [b-15.2] DNOC (dinitro-ortho-cresol), [b-15.3] binapacryl, [b-15.4] sulfuramide,
＜ｂ－１６：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）チャネルブロッカー＞
　ｂ－１６：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）チャネルブロッカーとして、［ｂ－１６．１］ベンスルタップ（ｂｅｎｓｕｌｔａｐ）、［ｂ－１６．２］カルタップ塩酸塩（ｃａｒｔａｐ　ｈｙｄｒｏｃｈｌｏｒｉｄｅ）、［ｂ－１６．３］チオシクラム（ｔｈｉｏｃｙｃｌａｍ）、［ｂ－１６．４］チオスルタップ（ｔｈｉｏｓｕｌｔａｐ）、［ｂ－１６．５］チオスルタップナトリウム塩（Ｔｈｉｏｓｕｌｔａｐ－ｓｏｄｉｕｍ）、［ｂ－１６．６］モノスルタップ（ｍｏｎｏｓｕｌｔａｐ）等が挙げられる。 <b-16: Nicotinic acetylcholine receptor (nAChR) channel blocker>
b-16: Nicotinic acetylcholine receptor (nAChR) channel blockers include, for example, [b-16.1] bensultap, [b-16.2] cartap hydrochloride, [b-16.3] thiocyclam, [b-16.4] thiosultap, [b-16.5] thiosultap sodium salt, and [b-16.6] monosultap.
＜ｂ－１７：ＣＨＳ１に作用するキチン生合成阻害剤＞
　ｂ－１７：ＣＨＳ１に作用するキチン生合成阻害剤として、［ｂ－１７．１］ビストリフルロン（ｂｉｓｔｒｉｆｌｕｒｏｎ）、［ｂ－１７．２］クロルフルアズロン（ｃｈｌｏｒｆｌｕａｚｕｒｏｎ）、［ｂ－１７．３］ジフルベンズロン（ｄｉｆｌｕｂｅｎｚｕｒｏｎ）、［ｂ－１７．４］フルシクロクスロン（ｆｌｕｃｙｃｌｏｘｕｒｏｎ）、［ｂ－１７．５］フルフェノクスロン（ｆｌｕｆｅｎｏｘｕｒｏｎ）、［ｂ－１７．６］ヘキサフルムロン（ｈｅｘａｆｌｕｍｕｒｏｎ）、［ｂ－１７．７］ルフェヌロン（ｌｕｆｅｎｕｒｏｎ）、［ｂ－１７．８］ノバルロン（ｎｏｖａｌｕｒｏｎ）、［ｂ－１７．９］ノビフルムロン（ｎｏｖｉｆｌｕｍｕｒｏｎ）、［ｂ－１７．１０］テフルベンズロン（ｔｅｆｌｕｂｅｎｚｕｒｏｎ）、［ｂ－１７．１１］トリフルムロン（ｔｒｉｆｌｕｍｕｒｏｎ）等が挙げられる。 <b-17: Chitin biosynthesis inhibitor acting on CHS1>
b-17: Chitin biosynthesis inhibitors acting on CHS1 include: [b-17.1] bistrifluron, [b-17.2] chlorfluazuron, [b-17.3] diflubenzuron, [b-17.4] flucycloxuron, and [b-17.5] flufenoxuron. on), [b-17.6] hexaflumuron, [b-17.7] lufenuron, [b-17.8] novaluron, [b-17.9] noviflumuron, [b-17.10] teflubenzuron, [b-17.11] triflumuron, and the like.
＜ｂ－１８：キチン生合成阻害剤タイプ１＞
　ｂ－１８：キチン生合成阻害剤タイプ１として、［ｂ－１８．１］ブプロフェジン（ｂｕｐｒｏｆｅｚｉｎ）等が挙げられる。 <b-18: Chitin biosynthesis inhibitor type 1>
b-18: Chitin biosynthesis inhibitor type 1 includes [b-18.1] buprofezin, etc.
＜ｂ－１９：ハエ目昆虫脱皮阻害剤＞
　ｂ－１９：ハエ目昆虫脱皮阻害剤として、［ｂ－１９．１］シロマジン（ｃｙｒｏｍａｚｉｎｅ）等が挙げられる。 <b-19: Diptera insect molting inhibitor>
b-19: Diptera molting inhibitors include [b-19.1] cyromazine, and the like.
＜ｂ－２０：脱皮ホルモン（エクダイソン）受容体アゴニスト＞
　ｂ－２０：脱皮ホルモン（エクダイソン）受容体アゴニストとして、［ｂ－２０．１］クロマフェノジド（ｃｈｒｏｍａｆｅｎｏｚｉｄｅ）、［ｂ－２０．２］ハロフェノジド（ｈａｌｏｆｅｎｏｚｉｄｅ）、［ｂ－２０．３］メトキシフェノジド（ｍｅｔｈｏｘｙｆｅｎｏｚｉｄｅ）、［ｂ－２０．４］テブフェノジド（ｔｅｂｕｆｅｎｏｚｉｄｅ）等が挙げられる。 <b-20: ecdysone receptor agonist>
b-20: Molting hormone (ecdysone) receptor agonists include, for example, [b-20.1] chromafenozide, [b-20.2] halofenozide, [b-20.3] methoxyfenozide, and [b-20.4] tebufenozide.
＜ｂ－２１：オクトパミン受容体アゴニスト＞
　ｂ－２１：オクトパミン受容体アゴニストとして、［ｂ－２１．１］アミトラズ（ａｍｉｔｒａｚ）等が挙げられる。 <b-21: Octopamine receptor agonist>
b-21: Octopamine receptor agonists include [b-21.1] amitraz, and the like.
＜ｂ－２２：ミトコンドリア電子伝達系複合体III阻害剤＞
　ｂ－２２：ミトコンドリア電子伝達系複合体III阻害剤として、［ｂ－２２．１］ヒドラメチルノン（ｈｙｄｒａｍｅｔｈｙｌｎｏｎ）、［ｂ－２２．２］アセキノシル（ａｃｅｑｕｉｎｏｃｙｌ）、［ｂ－２２．３］フルアクリピリム（ｆｌｕａｃｒｙｐｙｒｉｍ）、［ｂ－２２．４］ビフェナゼート（ｂｉｆｅｎａｚａｔｅ）等が挙げられる。 <b-22: mitochondrial electron transport complex III inhibitor>
b-22: Mitochondrial electron transport complex III inhibitors include, for example, [b-22.1] hydramethylnon, [b-22.2] acequinocyl, [b-22.3] fluacrypyrim, and [b-22.4] bifenazate.
＜ｂ－２３：ミトコンドリア電子伝達系複合体Ｉ阻害剤（ＭＥＴＩ）＞
　ｂ－２３：ミトコンドリア電子伝達系複合体Ｉ阻害剤（ＭＥＴＩ）として、［ｂ－２３．１］フェナザキン（ｆｅｎａｚａｑｕｉｎ）、［ｂ－２３．２］フェンピロキシメート（ｆｅｎｐｙｒｏｘｉｍａｔｅ）、［ｂ－２３．３］ピリダベン（ｐｙｒｉｄａｂｅｎ）、［ｂ－２３．４］ピリミジフェン（ｐｙｌｉｍｉｄｉｆｅｎ）、［ｂ－２３．５］テブフェンピラド（ｔｅｂｕｆｅｎｐｙｒａｄ）、［ｂ－２３．６］トルフェンピラド（ｔｏｌｆｅｎｐｙｒａｄ）、［ｂ－２３．７］ロテノン（ｒｏｔｅｎｏｎｅ）等が挙げられる。 <b-23: Mitochondrial electron transport complex I inhibitor (METI)>
b-23: Mitochondrial electron transport complex I inhibitors (METI) include, for example, [b-23.1] fenazaquin, [b-23.2] fenpyroximate, [b-23.3] pyridaben, [b-23.4] pyrimidifen, [b-23.5] tebufenpyrad, [b-23.6] tolfenpyrad, and [b-23.7] rotenone.
＜ｂ－２４：電位依存性ナトリウムチャネルブロッカー＞
　ｂ－２４：電位依存性ナトリウムチャネルブロッカーとして、［ｂ－２４．１］インドキサカルブ（ｉｎｄｏｘａｃａｒｂ）、［ｂ－２４．２］メタフルミゾン（ｍｅｔａｆｌｕｍｉｚｏｎｅ）等が挙げられる。 <b-24: Voltage-dependent sodium channel blocker>
b-24: Voltage-dependent sodium channel blockers include, for example, [b-24.1] indoxacarb, [b-24.2] metaflumizone, and the like.
＜ｂ－２５：アセチルＣｏＡカルボキシラーゼ阻害剤＞
　ｂ－２５：アセチルＣｏＡカルボキシラーゼ阻害剤として、［ｂ－２５．１］スピロジクロフェン（ｓｐｉｒｏｄｉｃｌｏｆｅｎ）、［ｂ－２５．２］スピロメシフェン（ｓｐｉｒｏｍｅｓｉｆｅｎ）、［ｂ－２５．３］スピロピジオン（ｓｐｉｒｏｐｉｄｉｏｎ）、［ｂ－２５．４］スピロテトラマト（ｓｐｉｒｏｔｅｔｒａｍａｔ）等が挙げられる。 <b-25: Acetyl CoA carboxylase inhibitor>
b-25: Acetyl CoA carboxylase inhibitors include, for example, [b-25.1] spirodiclofen, [b-25.2] spiromesifen, [b-25.3] spiropidion, and [b-25.4] spirotetramat.
＜ｂ－２６：ミトコンドリア電子伝達系複合体IV阻害剤＞
　ｂ－２６：ミトコンドリア電子伝達系複合体IV阻害剤として、［ｂ－２６．１］リン化アルミニウム（ａｌｕｍｉｎｕｍ　ｐｈｏｓｐｈｉｄｅ）、［ｂ－２６．２］リン化カルシウム（ｃａｌｃｉｕｍ　ｐｈｏｓｐｈｉｄｅ）、［ｂ－２６．３］リン化水素（ｐｈｏｓｐｈｉｎｅ）、［ｂ－２６．４］リン化亜鉛（ｚｉｎｃ　ｐｈｏｓｐｈｉｄｅ）、［ｂ－２６．５］シアン化カルシウム（ｃａｌｃｉｕｍ　ｃｙａｎｉｄｅ）、［ｂ－２６．６］シアン化カリウム（ｐｏｔａｓｓｉｕｍ　ｃｙａｎｉｄｅ）、［ｂ－２６．７］シアン化ナトリウム（ｓｏｄｉｕｍ　ｃｙａｎｉｄｅ）等が挙げられる。 <b-26: mitochondrial electron transport chain complex IV inhibitor>
b-26: Mitochondrial electron transport complex IV inhibitors include, for example, [b-26.1] aluminum phosphide, [b-26.2] calcium phosphide, [b-26.3] hydrogen phosphide, [b-26.4] zinc phosphide, [b-26.5] calcium cyanide, [b-26.6] potassium cyanide, and [b-26.7] sodium cyanide.
＜ｂ－２７：ミトコンドリア電子伝達系複合体II阻害剤＞
　ｂ－２７：ミトコンドリア電子伝達系複合体II阻害剤として、［ｂ－２７．１］シエノピラフェン（ｃｙｅｎｏｐｙｒａｆｅｎ）、［ｂ－２７．２］シフルメトフェン（ｃｙｆｌｕｍｅｔｏｆｅｎ）、［ｂ－２７．３］ピフルブミド（ｐｙｆｌｕｂｕｍｉｄｅ）等が挙げられる。 <b-27: mitochondrial electron transport complex II inhibitor>
b-27: Mitochondrial electron transport complex II inhibitors include [b-27.1] cyenopyrafen, [b-27.2] cyflumetofen, [b-27.3] pyflubumid, and the like.
＜ｂ－２８：リアノジン受容体モジュレーター＞
　ｂ－２８：リアノジン受容体モジュレーターとして、［ｂ－２８．１］クロラントラニリプロール（ｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、［ｂ－２８．２］シアントラニリプロール（ｃｙａｎｔｒａｎｉｌｉｐｒｏｌｅ）、［ｂ－２８．３］フルベンジアミド（ｆｌｕｂｅｎｄｉａｍｉｄｅ）、［ｂ－２８．４］シクラニリプロール（ｃｙｃｌａｎｉｌｉｐｒｏｌｅ）、［ｂ－２８．５］テトラニリプロール （ｔｅｔｒａｎｉｌｉｐｒｏｌｅ）等が挙げられる。 <b-28: Ryanodine receptor modulator>
b-28: Ryanodine receptor modulators include, for example, [b-28.1] chlorantraniliprole, [b-28.2] cyantraniliprole, [b-28.3] flubendiamide, [b-28.4] cyclaniliprole, and [b-28.5] tetraniliprole.
＜ｂ－２９：弦音器官モジュレーター標的部位未特定＞
　ｂ－２９：弦音器官モジュレーター標的部位未特定殺虫剤として、［ｂ－２９．１］フロニカミド（ｆｌｏｎｉｃａｍｉｄ）等が挙げられる。 <b-29: Chordotonal organ modulator target site unidentified>
b-29: Chordotonal organ modulators. Target site unspecified insecticides include [b-29.1] flonicamid, and the like.
＜ｂ－３０：ＧＡＢＡ作動性塩化物イオンチャネルアロステリックモジュレーター＞
　ｂ－３０：ＧＡＢＡ作動性塩化物イオンチャネルアロステリックモジュレーターとして、［ｂ－３０．１］ブロフラニリド（ｂｒｏｆｌａｎｉｌｉｄｅ）、［ｂ－３０．２］フルキサメタミド（ｆｌｕｘａｍｅｔａｍｉｄｅ）等が挙げられる。 <b-30: GABA-gated chloride ion channel allosteric modulator>
b-30: GABA-gated chloride ion channel allosteric modulators include, for example, [b-30.1] broflanilide, [b-30.2] fluxametamide, and the like.
＜ｂ－３１：バキュロウィルス＞
　ｂ－３１：バキュロウィルスとして、［ｂ－３１．１］コドリンガ　Ｃｙｄｉａ　ｐｏｍｏｎｅｌｌａ　ＧＶ（Ｃｙｄｉａ　ｐｏｍｏｎｅｌｌａ　ＧＶ）、［ｂ－３１．２］コドリンガモドキ　Ｔｈａｕｍａｔｏｔｉｂｉａ　ｌｅｕｃｏｔｒｅｔａ　ＧＶ（Ｔｈａｕｍａｔｏｔｉｂｉａ　ｌｅｕｃｏｔｒｅｔａ　ＧＶ）、［ｂ－３１．３］ビロードマメケムシＡｎｔｉｃａｒｓｉａ　ｇｅｍｍａｔａｌｉｓ　ＭＮＰＶ（Ａｎｔｉｃａｒｓｉａ　ｇｅｍｍａｔａｌｉｓ　ＭＮＰＶ）、［ｂ－３１．４］オオタバコガ　Ｈｅｌｉｃｏｖｅｒｐａ　ａｒｍｉｇｅｒａ　ＮＰＶ（Ｈｅｌｉｃｏｖｅｒｐａ　ａｒｍｉｇｅｒａ　ＮＰＶ）等が挙げられる。 <b-31: Baculovirus>
b-31: Examples of baculoviruses include [b-31.1] Cydia pomonella GV (Cydia pomonella GV), [b-31.2] Thaumatotibia leucotreta GV (Thaumatotibia leucotreta GV), [b-31.3] Anticarsia gemmatalis MNPV (Anticarsia gemmatalis MNPV), [b-31.4] Helicoverpa armigera NPV (Helicoverpa armigera NPV), and the like.
＜ｂ－３２：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）アロステリックモジュレーター部位ＩＩ＞
　ｂ－３２：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）アロステリックモジュレーター部位ＩＩとして、［ｂ－３２．１］ＧＳ－オメガ／カッパＨＸＴＸ－Ｈｖ１ａペプチド（ＧＳ－ｏｍｅｇａ／ｋａｐｐａ　ＨＸＴＸ－Ｈｖ１ａ　ｐｅｐｔｉｄｅ）等が挙げられる。 <b-32: Nicotinic acetylcholine receptor (nAChR) allosteric modulator site II>
b-32: Nicotinic acetylcholine receptor (nAChR) allosteric modulator site II includes [b-32.1] GS-omega/kappa HXTX-Hv1a peptide and the like.
＜ｂ－３３：その他の殺虫剤＞
　ｂ－３３：その他の殺虫剤として、［ｂ－３３．１］アザジラクチン（ａｚａｄｉｒａｃｈｔｉｎ）、［ｂ－３３．２］ベンゾキシメート（ｂｅｎｚｏｘｉｍａｔｅ）、［ｂ－３３．３］フェニソブロモレート（ｐｈｅｎｉｓｏｂｒｏｍｏｌａｔｅ）、［ｂ－３３．４］キノメチオナート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ）、［ｂ－３３．５］ジコホル（ｄｉｃｏｆｏｌ）、［ｂ－３３．６］石灰硫黄合剤（ＣａＳｘ）、［ｂ－３３．７］マンゼブ（ｍａｎｚｅｂ）、［ｂ－３３．８］ピリダリル（ｐｙｒｉｄａｌｙｌ）、［ｂ－３３．９］硫黄（ｓｕｌｆｕｒ）、［ｂ－３３．１０］ブロモプロピレート（ｂｒｏｍｏｐｒｏｐｙｌａｔｅ）、［ｂ－３３．１１］バークホルデリア属菌ボルバキア・ピピエンティス（Ｚａｐ）（Ｂｕｒｋｈｏｌｄｅｒｉａ　ｓｐｐ，Ｗｏｌｂａｃｈｉａ　ｐｉｐｉｅｎｔｉｓ　（Ｚａｐ））、［ｂ－３３．１２］アリタソウ抽出物（Ｃｈｅｎｏｐｏｄｉｕｍ　ａｍｂｒｏｓｉｏｉｄｅｓ　ｎｅａｒ　ａｍｂｒｏｓｉｏｉｄｅｓ　ｅｘｔｒａｃｔ）、［ｂ－３３．１３］グリセリンまたはプロパンジオールを持った脂肪酸モノエステル（Ｆａｔｔｙ　ａｃｉｄ　ｍｏｎｏｅｓｔｅｒｓ　ｗｉｔｈ　ｇｌｙｃｅｒｏｌ　ｏｒ　ｐｒｏｐａｎｅｄｉｏｌ）、［ｂ－３３．１４］ニームオイル（Ｎｅｅｍ　ｏｉｌ）、［ｂ－３３．１５］ボーベリア・バシアーナ株（Ｂｅａｕｖｅｒｉａ　ｂａｓｓｉａｎａ　ｓｔｒａｉｎｓ）、［ｂ－３３．１６］メタリジウム・アニソプリア株Ｆ５２（Ｍｅｔａｒｈｉｚｉｕｍ　ａｎｉｓｏｐｌｉａｅ　ｓｔｒａｉｎ　Ｆ５２）、［ｂ－３３．１７］ペシロマイセス・フモソロセウス・アポプカ株９７（Ｐａｅｃｉｌｏｍｙｃｅｓ　ｆｕｍｏｓｏｒｏｓｅｕｓ　Ａｐｏｐｋａ　ｓｔｒａｉｎ　９７）、［ｂ－３３．１８］珪藻土（ｄｉａｔｏｍｉｔｅ）、［ｂ－３３．１９］トリアザメート（ｔｒｉａｚａｍａｔｅ）、［ｂ－３３．２０］ジシクラニル（ｄｉｃｙｃｌａｎｉｌ）、［ｂ－３３．２１］ジノブトン（ｄｉｎｏｂｕｔｏｎ）、［ｂ－３３．２２］ジノカップ（ｄｉｎｏｃａｐ）、
［ｂ－３３．２３］シアン化水素（ｈｙｄｒｏｇｅｎ　ｃｙａｎｉｄｅ）、［ｂ－３３．２４］ヨウ化メチル（ｍｅｔｈｙｌ　ｉｏｄｉｄｅ）、［ｂ－３３．２５］カランジン（ｋａｒａｎｊｉｎ）、［ｂ－３３．２６］塩化水銀（ｍｅｒｃｕｒｙ　ｃｈｌｏｒｉｄｅ）、［ｂ－３３．２７］メチルイソチオシアネート（ｍｅｔｈｙｌ　ｉｓｏｔｈｉｏｃｙａｎａｔｅ）、［ｂ－３３．２８］ペンタクロロフェノール（ｐｅｎｔａｃｈｌｏｒｏｐｈｅｎｏｌ）、［ｂ－３３．２９］ホスフィン（ｐｈｏｓｐｈｉｎｅ）、［ｂ－３３．３０］ピペロニル　ブトキシド（ｐｉｐｅｒｏｎｙｌ　ｂｕｔｏｘｉｄｅ）、［ｂ－３３．３１］ポリナクチン複合体（ｐｏｌｙｎａｃｔｉｎｓ）、［ｂ－３３．３２］サバディラ（ｓａｂａｄｉｌｌａ）、［ｂ－３３．３３］スルコフロン塩（ｓｕｌｃｏｆｕｒｏｎ－ｓｏｄｉｕｍ）、［ｂ－３３．３４］トリブホス（ｔｒｉｂｕｆｏｓ）、［ｂ－３３．３５］アルドリン（ａｌｄｒｉｎ）、［ｂ－３３．３６］アミジチオオン（ａｍｉｄｉｔｈｉｏｎ）、［ｂ－３３．３７］アミドチオエート（ａｍｉｄｏｔｈｉｏａｔｅ）、［ｂ－３３．３８］アミノカルブ（ａｍｉｎｏｃａｒｂ）、［ｂ－３３．３９］アミトン（ａｍｉｔｏｎ）、［ｂ－３３．４０］アラマイト（ａｒａｍｉｔｅ）、［ｂ－３３．４１］アチダチオン（ａｔｈｉｄａｔｈｉｏｎ）、［ｂ－３３．４２］アゾトエート（ａｚｏｔｈｏａｔｅ）、［ｂ－３３．４３］ポリスルフィドバリウム（ｂａｒｉｕｍ　ｐｏｌｙｓｕｌｐｈｉｄｅ）、［ｂ－３３．４４］ベンクロチアズ（ｂｅｎｃｌｏｔｈｉａｚ）、［ｂ－３３．４５］５－（１，３－ベンゾジオキソール－５－イル）－３－ヘキシルシクロヘキサ－２－エノン（５－（１，３－ｂｅｎｚｏｄｉｏｘｏｌｅ－５－ｙｌ）－３－ｈｅｘｙｌｃｙｃｌｏｈｅｘａ－２－ｅｎｏｎｅ）、［ｂ－３３．４６］１，１－ビス（４－クロロフェニル）－２－エトキシエタノール（１，１－ｂｉｓ（４－ｃｈｌｏｒｏｐｈｅｎｙｌ）－２－ｅｔｈｏｘｙｅｔｈａｎｏｌ）、［ｂ－３３．４７］ブトネート（ｂｕｔｏｎａｔｅ）、［ｂ－３３．４８］ブトピロノキシル（ｂｕｔｏｐｙｒｏｎｏｘｙｌ）、［ｂ－３３．４９］２－（２－ブトキシエトキシ）エチル　チオシアナート（２－（２－ｂｕｔｏｘｙｅｔｈｏｘｙ）ｅｔｈｙｌ　ｔｈｉｏｃｙａｎａｔｅ）、［ｂ－３３．５０］カンフェクロル（ｃａｍｐｈｅｃｈｌｏｒ）、［ｂ－３３．５１］クロルベンシド（ｃｈｌｏｒｂｅｎｓｉｄｅ）、［ｂ－３３．５２］クロルデコン（ｃｈｌｏｒｄｅｃｏｎｅ）、［ｂ－３３．５３］クロルジメホルム（ｃｈｌｏｒｄｉｍｅｆｏｒｍ）、［ｂ－３３．５４］クロルフェネトール（ｃｈｌｏｒｆｅｎｅｔｈｏｌ）、［ｂ－３３．５５］クロルフェンソン（ｃｈｌｏｒｆｅｎｓｏｎ）、［ｂ－３３．５６］フルアズロン（ｆｌｕａｚｕｒｏｎ）、［ｂ－３３．５７］メタアルデヒド（ｍｅｔａｌｄｅｈｙｄｅ）、［ｂ－３３．５８］ビアラホス（ｂｉａｌａｐｈｏｓ）、［ｂ－３３．５９］塩酸レバミゾール（ｌｅｖａｍｉｓｏｌ）、［ｂ－３３．６０］アミドフルメト（ａｍｉｄｏｆｌｕｍｅｔ）、［ｂ－３３．６１］ピラフルプロール（ｐｙｒａｆｌｕｐｒｏｌｅ）、［ｂ－３３．６２］ピリプロール（ｐｙｒｉｐｒｏｌｅ）、［ｂ－３３．６３］トラロピリル（ｔｒａｌｏｐｙｒｉｌ）、［ｂ－３３．６４］フルピラゾフォス（ｆｌｕｐｙｒａｚｏｆｏｓ）、
［ｂ－３３．６５］ジオフェノラン（ｄｉｏｆｅｎｏｌａｎ）、［ｂ－３３．６６］クロルベンジレート（ｃｈｌｏｒｏｂｅｎｚｉｌａｔｅ）、［ｂ－３３．６７］フルフェンジン（ｆｌｕｆｅｎｚｉｎｅ）、［ｂ－３３．６８］ベンゾメート（ｂｅｎｚｏｍａｔｅ）、［ｂ－３３．６９］フルフェネリム（ｆｌｕｆｅｎｅｒｉｍ）、［ｂ－３３．７０］アルベンダゾール（ａｌｂｅｎｄａｚｏｌｅ）、［ｂ－３３．７１］オキシベンダゾール（ｏｘｉｂｅｎｄａｚｏｌｅ）、［ｂ－３３．７２］フェンベンダゾール（ｆｅｎｂｅｎｄａｚｏｌｅ）、［ｂ－３３．７３］メタム・ナトリウム（ｍｅｔａｍ－ｓｏｄｉｕｍ）、［ｂ－３３．７４］１，３－ジクロロプロペン（１，３－ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、［ｂ－３３．７５］エチレンジブロマイド（ｅｔｈｙｌｅｎｅ　ｄｉｂｒｏｍｉｄｅ）、［ｂ－３３．７６］アクリロニトリル（ａｃｒｙｌｏｎｉｔｒｉｌｅ）、［ｂ－３３．７７］ビス（２－クロロエチル）エーテル（ｂｉｓ（２－ｃｈｌｏｒｏｅｔｈｙｌ）ｅｔｈｅｒ）、［ｂ－３３．７８］１－ブロモ－２－クロロエタン（１－ｂｒｏｍｏ－２－ｃｈｌｏｒｏｅｔｈａｎｅ）、［ｂ－３３．７９］３－ブロモ－１－クロロプロパ－１－エン（３－ｂｒｏｍｏ－１－ｃｈｌｏｒｏｐｒｏｐ－１－ｅｎｅ）、［ｂ－３３．８０］ブロモシクレン（ｂｒｏｍｏｃｙｃｌｅｎ）、［ｂ－３３．８１］二硫化炭素（ｃａｒｂｏｎ　ｄｉｓｕｌｆｉｄｅ）、［ｂ－３３．８２］四塩化炭素（ｔｅｔｒａｃｈｌｏｒｏｍｅｔｈａｎｅ）、［ｂ－３３．８３］ネマデクチン（ｎｅｍａｄｅｃｔｉｎ）、［ｂ－３３．８４］シミアゾール（ｃｙｍｉａｚｏｌｅ）、［ｂ－３３．８５］サイトカイニン（ｃｙｔｏｋｉｎｉｎ）、［ｂ－３３．８６］２－（オクチルチオ）エタノール（２－（ｏｃｔｙｌｔｈｉｏ）ｅｔｈａｎｏｌ）、［ｂ－３３．８７］オレイン酸カリウム（ｐｏｔａｓｓｉｕｍ　ｏｌｅａｔｅ）、［ｂ－３３．８８］オレイン酸ナトリウム（ｓｏｄｉｕｍ　ｏｌｅａｔｅ）、［ｂ－３３．８９］マシン油（ｍａｃｈｉｎｅ　ｏｉｌ）、［ｂ－３３．９０］タール油（ｔａｒ　ｏｉｌ）、［ｂ－３３．９１］アナバシン（ａｎａｂａｓｉｎｅ）、［ｂ－３３．９２］酒石酸モランテル（ｍｏｒａｎｔｅｌ　ｔａｒｔｒａｔｅ）、［ｂ－３３．９３］除虫菊（Ｐｙｒｅｔｈｒｕｍ）、［ｂ－３３．９４］ナタネ油（ｒａｐｅ　ｓｅｅｄ　ｏｉｌ）、［ｂ－３３．９５］ダイズレチシン（ｓｏｙｂｅａｎ　ｌｅｃｉｔｈｉｎ）、［ｂ－３３．９６］デンプン（ｓｔａｒｃｈ）、［ｂ－３３．９７］ヒドロキシプロピルデンプン（ｈｙｄｒｏｘｙｐｒｏｐｙｌｓｔａｒｃｈ）、
［ｂ－３３．９８］脂肪酸グリセリド（ｄｅｃａｎｏｙｌｏｃｔａｎｏｙｌｇｌｙｃｅｒｏｌ）、［ｂ－３３．９９］ケイソウ土（ｄｉａｔｏｍｉｔｅ）、［ｂ－３３．１００］ＴＰＩＣ（ｔｒｉｐｒｏｐｙｌ　ｉｓｏｃｙａｎｕｒａｔｅ）、［ｂ－３３．１０１］Ｄ－Ｄ（１，３－Ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、［ｂ－３３．１０２］ペルオキソカルボナート（ｐｅｒｏｘｏｃａｒｂｏｎａｔｅ）、［ｂ－３３．１０３］ＭＢ－５９９（ｖｅｒｂｕｔｉｎ）、［ｂ－３３．１０４］ビス（２，３，３，３－テトラクロロプロピル）エーテル（ｂｉｓ（２，３，３，３－ｔｅｔｒａｃｈｌｏｒｏｐｒｏｐｙｌ）　ｅｔｈｅｒ）、［ｂ－３３．１０５］ＤＣＩＰ（ｂｉｓ（２－ｃｈｌｏｒｏ－１－ｍｅｔｈｙｌｅｔｈｙｌ）ｅｔｈｅｒ）、［ｂ－３３．１０６］ＥＮＴ－８１８４（Ｎ－（２－Ｅｔｈｙｌｈｅｘｙｌ）ｂｉｃｙｃｌｏｈｅｐｔ－５－ｅｎｅ－２，３－ｄｉｃａｒｂｏｘｉｍｉｄｅ）、［ｂ－３３．１０７］Ｂａｙｅｒ　２２４０８（Ｏ，Ｏ－ｄｉｅｔｈｙｌ　Ｏ－ｎａｐｈｔｈａｌｉｍｉｄｏ　ｐｈｏｓｐｈｏｒｏｔｈｉｏａｔｅ）、［ｂ－３３．１０８］Ｂａｙｅｒ　３２３９４（ｔｒｉｓ（１－ｄｏｄｅｃｙｌ－３－ｍｅｔｈｙｌ－２－ｐｈｅｎｙｌｂｅｎｚｉｍｉｄａｚｏｌｉｕｍ）ｈｅｘａｃｙａｎｏｆｅｒｒａｔｅ）、［ｂ－３３．１０９］フロメトキン（ｆｌｏｍｅｔｏｑｕｉｎ）、［ｂ－３３．１１０］ジクロロメゾチアズ（ｄｉｃｌｏｒｏｍｅｚｏｔｉａｚ）、［ｂ－３３．１１１］フルアザインドリジン（ｆｌｕａｚａｉｎｄｏｌｉｚｉｎｅ）、［ｂ－３３．１１２］シハロジアミド（ｃｙｈａｌｏｄｉａｍｉｄｅ）、［ｂ－３３．１１３］チオキサザフェン（ｔｉｏｘａｚａｆｅｎ）、［ｂ－３３．１１４］フルヘキサフォン（ｆｌｕｈｅｘａｆｏｎ）、［ｂ－３３．１１５］フルララネル（ｆｌｕｒａｌａｎｅｒ）、［ｂ－３３．１１６］テトラクロラントラニリプロール（ｔｅｔｒａｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、［ｂ－３３．１１７］サロラネル（ｓａｒｏｌａｎｅｒ）、［ｂ－３３．１１８］ロチラネル（ｌｏｔｉｌａｎｅｒ）、［ｂ－３３．１１９］チゴラネル（ｔｉｇｏｌａｎｅｒ）、［ｂ－３３．１２０］シクロキサプリド（ｃｙｃｌｏｘａｐｒｉｄ）、［ｂ－３３．１２１］フルエンスルホン（ｆｌｕｅｎｓｕｌｆｏｎｅ）、［ｂ－３３．１２２］ベンズピリモキサン（ｂｅｎｚｐｙｒｉｍｏｘａｎ）、［ｂ－３３．１２３］アシノナピル（ａｃｙｎｏｎａｐｙｒ）、［ｂ－３３．１２４］フルピリミン（ｆｌｕｐｙｒｉｍｉｎ）、［ｂ－３３．１２５］チクロピラゾフロール（ｔｙｃｌｏｐｙｒａｚｏｆｌｏｒ）、［ｂ－３３．１２６］オキサゾスルフィル（ｏｘａｚｏｓｕｌｆｙｌ）、［ｂ－３３．１２７］イソシクロセラム（ｉｓｏｃｙｃｌｏｓｅｒａｍ）、［ｂ－３３．１２８］ジンプロピリダズ（ｄｉｍｐｒｏｐｙｒｉｄａｚ）、［ｂ－３３．１２９］シプロフラニリド（ｃｙｐｒｏｆｌａｎｉｌｉｄｅ）、［ｂ－３３．１３０］ニコフルプロール（ｎｉｃｏｆｌｕｐｒｏｌｅ）、［ｂ－３３．１３１］シクロブトリフルラム（ｃｙｃｌｏｂｕｔｒｉｆｌｕｒａｍ）、［ｂ－３３．１３２］シクロキシリジン（ｃｙｃｌｏｘｙｌｉｄｉｎ）、［ｂ－３３．１３３］パイコンジン（ｐａｉｃｈｏｎｇｄｉｎｇ）、［ｂ－３３．１３４］グアジピル（ｇｕａｄｉｐｙｒ）、［ｂ－３３．１３５］シエトピラフェン（ｃｙｅｔｐｙｒａｆｅｎ）、［ｂ－３３．１３６］フルペンチオフェノックス（ｆｌｕｐｅｎｔｉｏｆｅｎｏｘ）、［ｂ－３３．１３７］ピリミノストロビン（ｐｙｒｉｍｉｎｏｓｔｒｏｂｉｎ）、［ｂ－３３．１３８］クロロプラレトリン（ｃｈｌｏｒｏｐｒａｌｌｅｔｈｒｉｎ）、［ｂ－３３．１３９］カッパービフェントリン（ｋａｐｐａ－ｂｉｆｅｎｔｈｒｉｎ）、［ｂ－３３．１４０］カッパーテフルトリン（ｋａｐｐａ－ｔｅｆｌｕｔｈｒｉｎ）、［ｂ－３３．１４１］ヘプタフルトリン（ｈｅｐｔａｆｌｕｔｈｒｉｎ）、 <b-33: Other insecticides>
b-33: Other insecticides include, [b-33.1] azadirachtin, [b-33.2] benzoximate, [b-33.3] phenisobromolate, [b-33.4] chinomethionate, [b-33.5] dicofol, [ b-33.6] lime sulfur (CaSx), [b-33.7] manzeb, [b-33.8] pyridalyl, [b-33.9] sulfur, [b-33.10] bromopropylate, [b-33.11] Burkholderia spp. Wolbachia pipientis (Zap) spp, Wolbachia pipientis (Zap)), [b-33.12] Chenopodium ambrosioides near ambrosioides extract, [b-33.13] Fatty acid monoesters with glycerol or propanediol, [b-33.14] Neem oil, [b-33.15] Beauveria bassiana strains, [b-33.16] Metarhizium anisopliae strain F52 strain F52), [b-33.17] Paecilomyces fumosoroseus Apopka strain 97, [b-33.18] diatomite, [b-33.19] triazamate, [b-33.20] dicyclanil, [b-33.21] dinobuton, [b-33.22] dinocap,
[b-33.23] Hydrogen cyanide, [b-33.24] Methyl iodide, [b-33.25] Karanjin, [b-33.26] Mercury chloride, [b-33.27] Methyl isothiocyanate, [b-33.28] Pentachlorophenol, [b-33.29] Phosphine, [b-33.30] Piperonyl butoxide butoxide), [b-33.31] polynactins, [b-33.32] sabadilla, [b-33.33] sulcofuron-sodium, [b-33.34] tribufos, [b-33.35] aldrin, [b-33.36] amidithione, [b- 33.37] amidothioate, [b-33.38] aminocarb, [b-33.39] amiton, [b-33.40] aramite, [b-33.41] athidathion, [b-33.42] azothoate, [b-33.43] barium polysulfide polysulphide), [b-33.44] benclothiaz, [b-33.45] 5-(1,3-benzodioxole-5-yl)-3-hexylcyclohexa-2-enone, [b-33.46 ]1,1-bis(4-chlorophenyl)-2-ethoxyethanol, [b-33.47]butonate, [b-33.48]butopyronoxyl, [b-33.49]2-(2-butoxyethoxy)ethyl thiocyanate thiocyanate), [b-33.50] camphechlor, [b-33.51] chlorbeneside, [b-33.52] chlordecone, [b-33.53] chlordimeform, [b-33.54] chlorphenetole, [b-33.55] chlorfenson, [b-33.56] fluazuron, [b- 33.57] metaldehyde, [b-33.58] bialaphos, [b-33.59] levamisole hydrochloride, [b-33.60] amidoflumet, [b-33.61] pyrafluprole, [b-33.62] pyriprole, [b-33.63] tralopyril, [b-33.64] flupyrazofos,
[b-33.65] diofenolan, [b-33.66] chlorobenzilate, [b-33.67] flufenzine, [b-33.68] benzomate, [b-33.69] flufenerim, [b-33.70] albendazole zole), [b-33.71] oxibendazole, [b-33.72] fenbendazole, [b-33.73] metam-sodium, [b-33.74] 1,3-dichloropropene, [b-33.75] ethylene dibromide dibromide), [b-33.76] acrylonitrile, [b-33.77] bis(2-chloroethyl)ether, [b-33.78] 1-bromo-2-chloroethane, [b-33.79] 3-bromo-1-chloroprop-1-ene, [b-33.80] bromocyclene, [b-33.81] carbon disulfide disulfide), [b-33.82] carbon tetrachloride (tetrachloromethane), [b-33.83] nemadectin (nemadectin), [b-33.84] cymiazole (cymiazole), [b-33.85] cytokinin (cytokinin), [b-33.86] 2-(octylthio)ethanol (2-(octylthio)ethanol), [b-33.87] potassium oleate (potassium oleate), [b-33.88] sodium oleate (sodium oleate), [b-33.89] machine oil (machine oil), [b-33.90] tar oil (tar oil), [b-33.91] anabasine, [b-33.92] morantel tartrate, [b-33.93] pyrethrum, [b-33.94] rapeseed oil, [b-33.95] soybean lecithin, [b-33.96] starch, [b-33.97] hydroxypropyl starch,
[b-33.98] Fatty acid glyceride (decanoyl octanoylglycerol), [b-33.99] Diatomite (diatomite), [b-33.100] TPIC (tripropyl isocyanurate), [b-33.101] D-D (1,3-dichloropropene), [b-33.102] Peroxocarbonate (peroxocarbonate), [b-33.103] MB-599 (verbutin), [b-33.104] Bis (2,3,3,3-tetrachloropropyl) ether (bis (2,3,3,3-tetrachloropropyl) ether), [b-33.105] DCIP (bis (2-chloro-1-methylethyl) ether), [b-33.106] ENT-8184 (N- (2-ethylhexyl) bicyclohept-5-ene-2,3-dicarboximide), [b-33.107] Bayer 22408 (O, O-diethyl O-naphthalimido phosphorothioate), [b-33.108] Bayer 32394 (tris(1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexacyanoferrate), [b-33.109] flometoquin, [b-33.110] dichloromezotiaz, [b-33.111] ] fluazaindolizine, [b-33.112] cyhalodiamide, [b-33.113] thioxazafen, [b-33.114] fluhexafon, [b-33.115] fluralaner ner), [b-33.116] tetrachlorantraniliprole, [b-33.117] sarolaner, [b-33.118] lotilaner, [b-33.119] tigolaner, [b-33.120] cycloxapride, [b-33.121] fluensulfone, [b-33.122] benzpyrimoxan, [b-33.123] acinonapyr, [b-33.124] flupirimine, [ b-33.125] tyclopyrazoflor, [b-33.126] oxazosulfyl, [b-33.127] isocycloseram, [b-33.128] dipropylidaz, [b-33.129] ciproflanilide, [b-33.130] nicoflurane, [b-33.131] cyclobutrifluram, [b-33.132] cycloxylidine, [b-33.133] paichondine ichongding), [b-33.134] guadipyr, [b-33.135] cyetpyrafen, [b-33.136] flupentiophenox, [b-33.137] pyriminostrobin, [b-33.138] chloroprallethrin, [b-33.139] kappa-bifenthrin, [b-33.140] kappa-tefluthrin, [b-33.141] heptafluthrin,
［ｂ－３３．１４２］式（ｓ１）
Figure JPOXMLDOC01-appb-C000106
で表される化合物（国際公開第２０２０／０１８３６２参照）、 [b-33.142] Formula (s1)
Figure JPOXMLDOC01-appb-C000106
A compound represented by the formula (see International Publication No. 2020/018362),
［ｂ－３３．１４３］式（ｓ２）
Figure JPOXMLDOC01-appb-C000107
で表される化合物（国際公開第２００６／０８９６３３参照）、 [b-33.143] Formula (s2)
Figure JPOXMLDOC01-appb-C000107
(see International Publication No. WO 2006/089633),
［ｂ－３３．１４４］式（ｓ３）
Figure JPOXMLDOC01-appb-C000108
で表される化合物（国際公開第２０１８／０１１１１１号参照）、 [b-33.144] Formula (s3)
Figure JPOXMLDOC01-appb-C000108
A compound represented by the formula (see International Publication No. 2018/011111),
［ｂ－３３．１４５］式（ｓ４）
Figure JPOXMLDOC01-appb-C000109
で表される化合物（国際公開第２０１２／１２６７６６号参照）、 [b-33.145] Formula (s4)
Figure JPOXMLDOC01-appb-C000109
A compound represented by the formula (see International Publication No. WO 2012/126766),
［ｂ－３３．１４６］式（ｓ５）
Figure JPOXMLDOC01-appb-C000110
で表される化合物（国際公開第２０１９／２１５０７６号参照）、 [b-33.146] Formula (s5)
Figure JPOXMLDOC01-appb-C000110
A compound represented by the formula (see International Publication No. 2019/215076),
［ｂ－３３．１４７］式（ｓ６）
Figure JPOXMLDOC01-appb-C000111
で表される化合物（国際公開第２０１６／１８０８０２号参照）、 [b-33.147] Formula (s6)
Figure JPOXMLDOC01-appb-C000111
A compound represented by the formula (see International Publication No. WO 2016/180802),
［ｂ－３３．１４８］式（ｓ７）
Figure JPOXMLDOC01-appb-C000112
で表される化合物（国際公開第２０１４／０５３４５０号参照）、 [b-33.148] Formula (s7)
Figure JPOXMLDOC01-appb-C000112
A compound represented by the formula (see International Publication No. WO 2014/053450),
［ｂ－３３．１４９］式（ｓ８）
Figure JPOXMLDOC01-appb-C000113
で表される化合物（国際公開第２０１３／０９２３５０号参照）、 [b-33.149] Formula (s8)
Figure JPOXMLDOC01-appb-C000113
A compound represented by the formula (see International Publication No. WO 2013/092350),
［ｂ－３３．１５０］式（ｓ９）
Figure JPOXMLDOC01-appb-C000114
で表される化合物（国際公開第２０１２／０２７５２１号参照）、 [b-33.150] Formula (s9)
Figure JPOXMLDOC01-appb-C000114
A compound represented by the formula (see International Publication No. WO 2012/027521),
［ｂ－３３．１５１］式（ｓ１０）
Figure JPOXMLDOC01-appb-C000115
で表される化合物（国際公開第２０１７／０６５２２８号参照）、 [b-33.151] Formula (s10)
Figure JPOXMLDOC01-appb-C000115
A compound represented by the formula (see International Publication No. WO 2017/065228),
［ｂ－３３．１５２］式（ｓ１１）
Figure JPOXMLDOC01-appb-C000116
で表される化合物（国際公開第２０１５／１３３６０３号参照）、 [b-33.152] Formula (s11)
Figure JPOXMLDOC01-appb-C000116
A compound represented by the formula (see International Publication No. WO 2015/133603),
［ｂ－３３．１５３］式（ｓ１２）
Figure JPOXMLDOC01-appb-C000117
で表される化合物（国際公開第２０１０／０９０３４４号参照）、 [b-33.153] Formula (s12)
Figure JPOXMLDOC01-appb-C000117
A compound represented by the formula (see International Publication No. WO 2010/090344),
［ｂ－３３．１５４］式（ｓ１３）
Figure JPOXMLDOC01-appb-C000118
で表される化合物（国際公開第２０１５／０２５８２６号参照）、 [b-33.154] Formula (s13)
Figure JPOXMLDOC01-appb-C000118
A compound represented by the formula (see International Publication No. WO 2015/025826 ),
［ｂ－３３．１５５］式（ｓ１４）
Figure JPOXMLDOC01-appb-C000119
で表される化合物（国際公開第２０１６／１４４３５１参照）等が挙げられる。 [b-33.155] Formula (s14)
Figure JPOXMLDOC01-appb-C000119
and the like (see International Publication No. 2016/144351).
　殺菌剤に含まれる成分は以下の群ｃで示されるとおりであり、これらの塩、異性体およびＮ－オキシド体を含む。ただし、公知の殺菌剤はこれらに限定されるものではない。 The components contained in the fungicide are as shown in group c below, and include their salts, isomers and N-oxides. However, known fungicides are not limited to these.
群ｃ：
＜ｃ－１：フェニルアミド系殺菌剤＞
　ｃ－１：フェニルアミド系殺菌剤として、［ｃ－１．１］ベナラキシル（ｂｅｎａｌａｘｙｌ）、［ｃ－１．２］ベナラキシルＭまたはキララキシル（ｂｅｎａｌａｘｙｌ－Ｍまたはｋｉｒａｌａｘｙｌ）、［ｃ－１．３］フララキシル（ｆｕｒａｌａｘｙｌ）、［ｃ－１．４］メタラキシル（ｍｅｔａｌａｘｙｌ）、［ｃ－１．５］メタラキシルＭまたはメフェノキサム（ｍｅｔａｌａｘｙｌ－Ｍまたはｍｅｆｅｎｏｘａｍ）、［ｃ－１．６］オキサジキシル（ｏｘａｄｉｘｙｌ）、［ｃ－１．７］オフラセ（ｏｆｕｒａｃｅ）等が挙げられる。 Group c:
<c-1: Phenylamide fungicide>
c-1: Phenylamide fungicides include, for example, [c-1.1] benalaxyl, [c-1.2] benalaxyl M or kiraraxyl, [c-1.3] furalaxyl, [c-1.4] metalaxyl, [c-1.5] metalaxyl M or mefenoxam, [c-1.6] oxadixyl, and [c-1.7] ofurace.
＜ｃ－２：ヒドロキシ（２－アミノー）ピリミジン系殺菌剤＞
　ｃ－２：ヒドロキシ（２－アミノー）ピリミジン系殺菌剤として、［ｃ－２．１］ブピリメート（ｂｕｐｉｒｉｍａｔｅ）、［ｃ－２．２］ジメチリモール（ｄｉｍｅｔｈｉｒｉｍｏｌ）、［ｃ－２．３］エチリモール（ｅｔｈｉｒｉｍｏｌ）等が挙げられる。 <c-2: Hydroxy(2-amino)pyrimidine fungicide>
c-2: Hydroxy(2-amino)pyrimidine fungicides include [c-2.1] bupirimate, [c-2.2] dimethylimol, and [c-2.3] ethirimol.
＜ｃ－３：芳香族ヘテロ環系殺菌剤＞
　ｃ－３：芳香族ヘテロ環系殺菌剤として、［ｃ－３．１］ヒメキサゾール（ｈｙｍｅｘａｚｏｌｅ）、［ｃ－３．２］オキソリニック酸（ｏｘｏｌｉｎｉｃ　ａｃｉｄ）等が挙げられる。 <c-3: Aromatic heterocyclic fungicides>
c-3: Aromatic heterocyclic fungicides include, for example, [c-3.1] hymexazole and [c-3.2] oxolinic acid.
＜ｃ－４：カルボン酸系殺菌剤＞
ｃ－４：カルボン酸系殺菌剤として、［ｃ－４．１］オクチリノン（ｏｃｔｈｉｌｉｎｏｎｅ）等が挙げられる。 <c-4: Carboxylic acid fungicide>
c-4: Carboxylic acid fungicides include [c-4.1]octhilinone, etc.
＜ｃ－５：β―チューブリン重合阻害剤＞
　ｃ－５：β―チューブリン重合阻害剤として、［ｃ－５．１］ベノミル（ｂｅｎｏｍｙｌ）、［ｃ－５．２］カルベンダジム（ｃａｒｂｅｎｄａｚｉｍ）、［ｃ－５．３］フベリダゾール（ｆｕｂｅｒｉｄａｚｏｌｅ）、［ｃ－５．４］チアベンダゾール（ｔｈｉａｂｅｎｄａｚｏｌｅ）、［ｃ－５．５］チオファネート（ｔｈｉｏｐｈａｎａｔｅ）、［ｃ－５．６］チオファネートメチル（ｔｈｉｏｐｈａｎａｔｅ-ｍｅｔｈｙｌ）、［ｃ－５．７］ジエトフェンカルブ（ｄｉｅｔｈｏｆｅｎｃａｒｂ）、［ｃ－５．８］ゾキサミド（ｚｏｘａｍｉｄｅ）、［ｃ－５．９］エタボキサム（ｅｔｈａｂｏｘａｍ）等が挙げられる。 <c-5: β-tubulin polymerization inhibitor>
c-5: β-tubulin polymerization inhibitors include, for example, [c-5.1] benomyl, [c-5.2] carbendazim, [c-5.3] fuberidazole, [c-5.4] thiabendazole, [c-5.5] thiophanate, [c-5.6] thiophanate-methyl, [c-5.7] diethofencarb, [c-5.8] zoxamide, and [c-5.9] ethaboxam.
＜ｃ－６：細胞分裂阻害剤＞
　ｃ－６：細胞分裂阻害剤として、［ｃ－６．１］ペンシクロン（ｐｅｎｃｙｃｕｒｏｎ）等が挙げられる。 <C-6: Cell division inhibitor>
c-6: Cell division inhibitors include, for example, [c-6.1] pencycuron, etc.
＜ｃ－７：スペクトリン様タンパク質の非局在化＞
ｃ－７：スペクトリン様タンパク質の非局在化に係る殺菌剤として、［ｃ－７．１］フルオピコリド（ｆｌｕｏｐｉｃｏｌｉｄｅ）、［ｃ－７．２］フルオピモミド（ｆｌｕｏｐｉｍｏｍｉｄｅ）等が挙げられる。 <c-7: Delocalization of Spectrin-like Protein>
c-7: Examples of fungicides involved in the delocalization of spectrin-like proteins include [c-7.1] fluopicolide, [c-7.2] fluopimomide, and the like.
＜ｃ－８：アクチン/ミオシン/フィンブリン機能＞
　ｃ－８：アクチン/ミオシン/フィンブリン機能に係る殺菌剤として、［ｃ－８．１］フェナマクリル（Ｐｈｅｎａｍａｃｒｉｌ）、［ｃ－８．２］メトラフェノン（ｍｅｔｒａｆｅｎｏｎｅ）、［ｃ－８．３］ピリオフェノン（ｐｙｒｉｏｆｅｎｏｎｅ）等が挙げられる。 <c-8: Actin/myosin/fimbrin functions>
c-8: Bactericides relating to actin/myosin/fimbrin function include [c-8.1] phenamacril, [c-8.2] metrafenone, and [c-8.3] pyriofenone.
＜ｃ－９：複合体Ｉ：ＮＡＤＨ酸化還元酵素阻害剤＞
　ｃ－９：複合体Ｉ：ＮＡＤＨ酸化還元酵素阻害剤として、［ｃ－９．１］ジフルメトリム（ｄｉｆｌｕｍｅｔｏｒｉｍ　）、［ｃ－９．２］トルフェンピラド（ｔｏｌｆｅｎｐｙｒａｄ）、［ｃ－９．３］フェナザキン（ｆｅｎａｚａｑｕｉｎ）等が挙げられる。 <c-9: Complex I: NADH oxidoreductase inhibitor>
c-9: Complex I: NADH oxidoreductase inhibitors include [c-9.1] diflumetrim, [c-9.2] tolfenpyrad, [c-9.3] fenazaquin, and the like.
＜ｃ－１０：ＳＤＨＩ剤（コハク酸脱水素酵素阻害剤）＞
　ｃ－１０：ＳＤＨＩ剤（コハク酸脱水素酵素阻害剤）として、［ｃ－１０．１］ベノダニル（ｂｅｎｏｄａｎｉｌ）、［ｃ－１０．２］ベンゾビンジフルピル（ｂｅｎｚｏｖｉｎｄｉｆｌｕｐｙｒ）、［ｃ－１０．３］ビキサフェン（ｂｉｘａｆｅｎ）、［ｃ－１０．４］ボスカリド（ｂｏｓｃａｌｉｄ）、［ｃ－１０．５］カルボキシン（ｃａｒｂｏｘｉｎ）、［ｃ－１０．６］フェンフラム（ｆｅｎｆｕｒａｍ）、［ｃ－１０．７］フルオピラム（ｆｌｕｏｐｙｒａｍ）、［ｃ－１０．８］フルトラニル（ｆｌｕｔｏｌａｎｉｌ）、［ｃ－１０．９］フルキサピロキサド（ｆｌｕｘａｐｙｒｏｘａｄ）、［ｃ－１０．１０］フラメトピル（ｆｕｒａｍｅｔｐｙｒ）、［ｃ－１０．１１］イソフェタミド（ｉｓｏｆｅｔａｍｉｄ）、［ｃ－１０．１２］イソピラザム（ｉｓｏｐｙｒａｚａｍ）、［ｃ－１０．１３］メプロニル（ｍｅｐｒｏｎｉｌ）、［ｃ－１０．１４］オキシカルボキシン（ｏｘｙｃａｒｂｏｘｉｎ）、［ｃ－１０．１５］ペンチオピラド（ｐｅｎｔｈｉｏｐｙｒａｄ）、［ｃ－１０．１６］ペンフルフェン（ｐｅｎｆｌｕｆｅｎ）、［ｃ－１０．１７］ピジフルメトフェン（ｐｙｄｉｆｌｕｍｅｔｏｆｅｎ）、［ｃ－１０．１８］セダキサン（ｓｅｄａｘａｎｅ）、［ｃ－１０．１９］チフルザミド（ｔｈｉｆｌｕｚａｍｉｄｅ）、［ｃ－１０．２０］ピラジフルミド（ｐｙｒａｚｉｆｌｕｍｉｄ）、［ｃ－１０．２１］イソフルシプラム（ｉｓｏｆｌｕｃｙｐｒａｍ）、［ｃ－１０．２２］フルインダピル（ｆｌｕｉｎｄａｐｙｒ）、［ｃ－１０．２３］インピルフルキサム（ｉｎｐｙｒｆｌｕｘａｍ）等が挙げられる。 <c-10: SDHI agents (succinate dehydrogenase inhibitors)>
c-10: SDHI agents (succinate dehydrogenase inhibitors): [c-10.1] benodanil, [c-10.2] benzovindiflupyr, [c-10.3] bixafen, [c-10.4] boscalid, [c-10.5] carboxin, [c-10.6] phenoxyethanol, fenfuram, [c-10.7] fluopyram, [c-10.8] flutolanil, [c-10.9] fluxapyroxad, [c-10.10] furametpyr, [c-10.11] isofetamide, [c-10.12] isopyrazam sopyrazam, [c-10.13] mepronil, [c-10.14] oxycarboxin, [c-10.15] penthiopyrad, [c-10.16] penflufen, [c-10.17] pydiflumetofen, [c-10.18] sedaki Examples of such anti-inflammatory drugs include sedaxane, [c-10.19] thifluzamide, [c-10.20] pyraziflumid, [c-10.21] isoflucipram, [c-10.22] fluindapyr, and [c-10.23] inpyrfluxam.
＜ｃ－１１：ＱｏＩ剤（キノン外部阻害剤）＞
　ｃ－１１：ＱｏＩ剤（キノン外部阻害剤）として、［ｃ－１１．１］アゾキシストロビン（ａｚｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．２］クモキシストロビン（ｃｏｕｍｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．３］ジモキシストロビン（ｄｉｍｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．４］エノキサストロビン（ｅｎｏｘａｓｔｒｏｂｉｎ）、［ｃ－１１．５］ファモキサドン（ｆａｍｏｘａｄｏｎｅ）、［ｃ－１１．６］フェンアミドン（ｆｅｎａｍｉｄｏｎｅ）、［ｃ－１１．７］フェナミンストロビン（ｆｅｎａｍｉｎｓｔｒｏｂｉｎ）、［ｃ－１１．８］フルフェノキシストロビン（ｆｌｕｆｅｎｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．９］フルオキサストロビン（ｆｌｕｏｘａｓｔｒｏｂｉｎ）、［ｃ－１１．１０］クレソキシムメチル（ｋｒｅｓｏｘｉｍ－ｍｅｔｈｙｌ）、［ｃ－１１．１１］マンデストロビン（ｍａｎｄｅｓｔｒｏｂｉｎ）、［ｃ－１１．１２］メトミノストロビン（ｍｅｔｏｍｉｎｏｓｔｒｏｂｉｎ）、［ｃ－１１．１３］オリサストロビン（ｏｒｙｓａｓｔｒｏｂｉｎ）、［ｃ－１１．１４］ピコキシストロビン（ｐｉｃｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．１５］ピラクロストロビン（ｐｙｒａｃｌｏｓｔｒｏｂｉｎ）、［ｃ－１１．１６］ピラメトストロビン（ｐｙｒａｍｅｔｏｓｔｒｏｂｉｎ）、［ｃ－１１．１７］ピラオキシストロビン（ｐｙｒａｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．１８］ピリベンカルブ（ｐｙｒｉｂｅｎｃａｒｂ）、［ｃ－１１．１９］トリクロピリカルブ（ｔｒｉｃｌｏｐｙｒｉｃａｒｂ）、［ｃ－１１．２０］トリフロキシストロビン（ｔｒｉｆｌｏｘｙｓｔｒｏｂｉｎ）、［ｃ－１１．２１］メチルテトラプロール（ｍｅｔｙｌｔｅｔｒａｐｒｏｌe）等が挙げられる。 <c-11: QoI agent (quinone external inhibitor)>
c-11: QoI agents (quinone external inhibitors) include, [c-11.1] azoxystrobin, [c-11.2] coumoxystrobin, [c-11.3] dimoxystrobin, [c-11.4] enoxastrobin, [c-11.5] famoxadone, [c- 11.6] fenamidone, [c-11.7] phenaminestrobin, [c-11.8] flufenoxystrobin, [c-11.9] fluoxastrobin, [c-11.10] kresoxim-methyl, [c-11.11] mandestrobin (mandestrobin), [c-11.12] metominostrobin, [c-11.13] orysastrobin, [c-11.14] picoxystrobin, [c-11.15] pyraclostrobin, [c-11.16] pyrametostrobin n), [c-11.17] pyraoxystrobin, [c-11.18] pyribencarb, [c-11.19] triclopyricarb, [c-11.20] trifloxystrobin, [c-11.21] methyltetraprole, and the like.
＜ｃ－１２：ＱｉＩ剤（キノン内部阻害剤）＞
　ｃ－１２：ＱｉＩ剤（キノン内部阻害剤）として、［ｃ－１２．１］アミスルブロム（ａｍｉｓｕｌｂｒｏｍ）、［ｃ－１２．２］シアゾファミド（ｃｙａｚｏｆａｍｉｄ）、［ｃ－１２．３］フェンピコキサミド（ｆｅｎｐｉｃｏｘａｍｉｄ）等が挙げられる。 <c-12: QiI agent (quinone internal inhibitor)>
c-12: QiI agents (quinone internal inhibitors) include, for example, [c-12.1] amisulbrom, [c-12.2] cyazofamid, and [c-12.3] fenpicoxamid.
＜ｃ－１３：酸化的リン酸化脱共役阻害剤＞
　ｃ－１３：酸化的リン酸化脱共役阻害剤として、［ｃ－１３．１］ビナパクリル（ｂｉｎａｐａｃｒｙｌ）、［ｃ－１３．２］メプチルジノカップ（ｍｅｐｔｙｌｄｉｎｏｃａｐ）、［ｃ－１３．３］ジノカップ（ｄｉｎｏｃａｐ）、［ｃ－１３．４］フルアジナム（ｆｌｕａｚｉｎａｍ）、［ｃ－１３．５］フェリムゾン（ｆｅｒｉｍｚｏｎｅ）等が挙げられる。 <c-13: Oxidative phosphorylation uncoupling inhibitor>
c-13: oxidative phosphorylation uncoupling inhibitors include, for example, [c-13.1] binapacryl, [c-13.2] meptyldinocap, [c-13.3] dinocap, [c-13.4] fluazinam, and [c-13.5] ferimzone.
＜ｃ－１４：ＡＴＰ合成酵素阻害剤＞
　ｃ－１４：ＡＴＰ合成酵素阻害剤として、［ｃ－１４．１］酢酸トリフェニルスズ（ｆｅｎｔｉｎ　ａｃｅｔａｔｅ）、［ｃ－１４．２］塩化トリフェニルスズ（ｆｅｎｔｉｎ　ｃｈｌｏｒｉｄｅ）、［ｃ－１４．３］水酸化トリフェニルスズ（ｆｅｎｔｉｎ　ｈｙｄｒｏｘｉｄｅ）等が挙げられる。 <c-14: ATP synthase inhibitor>
c-14: ATP synthase inhibitors include, for example, [c-14.1] triphenyltin acetate (fentin acetate), [c-14.2] triphenyltin chloride (fentin chloride), [c-14.3] triphenyltin hydroxide (fentin hydroxide), and the like.
＜ｃ－１５：ＡＴＰ輸送＞
　ｃ－１５：ＡＴＰ輸送に係る殺菌剤として、［ｃ－１５．１］シルチオファム（ｓｉｌｔｈｉｏｆａｍ）等が挙げられる。 <c-15: ATP transport>
c-15: Examples of fungicides related to ATP transport include [c-15.1]silthiofam.
＜ｃ－１６：ＱｏＳＩ剤（キノン外部スチグマテリン結合サブサイト阻害剤）＞
　ｃ－１６：ＱｏＳＩ剤（キノン外部スチグマテリン結合サブサイト阻害剤）として、［ｃ－１６．１］アメトクトラジン（ａｍｅｔｏｃｔｒａｄｉｎ）等が挙げられる。 <c-16: QoSI agent (quinone external stigmatellin binding subsite inhibitor)>
c-16: QoSI agents (quinone external stigmatellin binding subsite inhibitors) include [c-16.1] ametoctradin, etc.
＜ｃ－１７：メチオニン生合成阻害剤＞
　ｃ－１７：メチオニン生合成阻害剤として、［ｃ－１７．１］シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）、［ｃ－１７．２］メパニピリム（ｍｅｐａｎｉｐｙｒｉｍ）、［ｃ－１７．３］ピリメタニル（ｐｙｒｉｍｅｔｈａｎｉｌ）等が挙げられる。 <c-17: methionine biosynthesis inhibitor>
c-17: Methionine biosynthesis inhibitors include [c-17.1] cyprodinil, [c-17.2] mepanipyrim, [c-17.3] pyrimethanil, and the like.
＜ｃ－１８：タンパク質生合成阻害剤＞
　ｃ－１８：タンパク質生合成阻害剤として、［ｃ－１８．１］ブラストサイジンＳ（ｂｌａｓｔｉｃｉｄｉｎ－Ｓ）、［ｃ－１８．２］カスガマイシン（ｋａｓｕｇａｍｙｃｉｎ）、［ｃ－１８．３］ストレプトマイシン（ｓｔｒｅｐｔｏｍｙｃｉｎ）、［ｃ－１８．４］オキシテトラサイクリン（ｏｘｙｔｅｔｒａｃｙｃｌｉｎｅ）等が挙げられる。 <c-18: Protein biosynthesis inhibitor>
c-18: Protein biosynthesis inhibitors include, for example, [c-18.1] blasticidin S, [c-18.2] kasugamycin, [c-18.3] streptomycin, and [c-18.4] oxytetracycline.
＜ｃ－１９：シグナル伝達阻害剤＞
　ｃ－１９：シグナル伝達阻害剤として、［ｃ－１９．１］キノキシフェン（ｑｕｉｎｏｘｙｆｅｎ）、［ｃ－１９．２］プロキナジド（ｐｒｏｑｕｉｎａｚｉｄ）、［ｃ－１９．３］フェンピクロニル（ｆｅｎｐｉｃｌｏｎｉｌ）、［ｃ－１９．４］フルジオキソニル（ｆｌｕｄｉｏｘｏｎｉｌ）、［ｃ－１９．５］クロゾリネート（ｃｈｌｏｚｏｌｉｎａｔｅ）、［ｃ－１９．６］ジメタクロン（ｄｉｍｅｔｈａｃｈｌｏｎｅ）、［ｃ－１９．７］イプロジオン（ｉｐｒｏｄｉｏｎｅ）、［ｃ－１９．８］プロシミドン（ｐｒｏｃｙｍｉｄｏｎｅ）、［ｃ－１９．９］ビンクロゾリン（ｖｉｎｃｌｏｚｏｌｉｎ）等が挙げられる。 <C-19: Signal Transduction Inhibitor>
c-19: Signal transduction inhibitors include, for example, [c-19.1] quinoxyfen, [c-19.2] proquinazid, [c-19.3] fenpiclonil, [c-19.4] fludioxonil, [c-19.5] chlorzolinate, [c-19.6] dimethachlon, [c-19.7] iprodione, [c-19.8] procymidone, and [c-19.9] vinclozolin.
＜ｃ－２０：脂質および細胞膜生合成阻害剤＞
　ｃ－２０：脂質および細胞膜生合成阻害剤として、
［ｃ－２０．１］エジフェンホス（ｅｄｉｆｅｎｐｈｏｓ）、［ｃ－２０．２］イプロベンホス（ｉｐｒｏｂｅｎｆｏｓ）、［ｃ－２０．３］イソプロチオラン（ｉｓｏｐｒｏｔｈｉｏｌａｎｅ）、［ｃ－２０．４］ピラゾホス（ｐｙｒａｚｏｐｈｏｓ）、［ｃ－２０．５］ビフェニル（ｂｉｐｈｅｎｙｌ）、［ｃ－２０．６］クロロネブ（ｃｈｌｏｒｏｎｅｂ）、［ｃ－２０．７］ジクロラン（ｄｉｃｌｏｒａｎ）、［ｃ－２０．８］キントゼン（ｑｕｉｎｔｏｚｅｎｅ）、［ｃ－２０．９］テクナゼン（ｔｅｃｎａｚｅｎｅ）、［ｃ－２０．１０］トルクロホスメチル（ｔｏｌｃｌｏｆｏｓ－ｍｅｔｈｙｌ）、［ｃ－２０．１１］エトリジアゾール（ｅｃｈｌｏｍｅｚｏｌ　ｏｒ　ｅｔｒｉｄｉａｚｏｌｅ）、［ｃ－２０．１２］ヨードカルブ（ｉｏｄｏｃａｒｂ）、［ｃ－２０．１３］プロパモカルブ（ｐｒｏｐａｍｏｃａｒｂ）、［ｃ－２０．１４］プロチオカルブ（ｐｒｏｔｈｉｏｃａｒｂ）等が挙げられる。 <C-20: Lipid and cell membrane biosynthesis inhibitor>
c-20: As an inhibitor of lipid and cell membrane biosynthesis,
[c-20.1] edifenphos, [c-20.2] iprobenfos, [c-20.3] isoprothiolane, [c-20.4] pyrazophos, [c-20.5] biphenyl, [c-20.6] chloroneb, [c-20.7] dicloran, [c-20.8] quintozene, [c-20.9] tecnazene, [c-20.10] tolclofos-methyl, [c-20.11] etridiazole [c-20.12] iodocarb, [c-20.13] propamocarb, and [c-20.14] prothiocarb.
＜ｃ－２１：細胞膜の攪乱剤＞
　ｃ－２１：細胞膜の攪乱剤に係る殺菌剤として、［ｃ－２１．１］ゴセイカユプテ(ティーツリー)の抽出物（ｅｘｔｒａｃｔ　ｆｒｏｍ　Ｍｅｌａｌｅｕｃａ　ａｌｔｅｒｎｉｆｏｌｉａ）、［ｃ－２１．２］植物油類（混合物）オイゲノール、ゲラニオール、チモール（ｐｌａｎｔ　ｏｉｌｓ　（ｍｉｘｔｕｒｅｓ）：　ｅｕｇｅｎｏｌ，　ｇｅｒａｎｉｏｌ，　ｔｈｙｍｏｌ　）等が挙げられる。 <c-21: Cell membrane disruptors>
C-21: Fungicides related to cell membrane disruptors include, for example, [C-21.1] extract from Melaleuca alternifolia, [C-21.2] plant oils (mixtures): eugenol, geraniol, thymol, and the like.
＜ｃ－２２：エルゴステロール結合剤＞
　ｃ－２２：エルゴステロール結合に係る殺菌剤として、［ｃ－２２．１］ナタマイシン（ｎａｔａｍｙｃｉｎ）等が挙げられる。 <c-22: Ergosterol binder>
c-22: Examples of fungicides related to ergosterol binding include [c-22.1] natamycin.
＜ｃ－２３：オキシステロール結合タンパク質阻害剤＞
　ｃ－２３：オキシステロール結合タンパク質阻害剤として、［ｃ－２３．１］オキサチアピプロリン（ｏｘａｔｈｉａｐｉｐｒｏｌｉｎ）、［ｃ－２３．２］フルオキサピプロリン（ｆｌｕｏｘａｐｉｐｒｏｌｉｎ）等が挙げられる。 <C-23: Oxysterol Binding Protein Inhibitor>
c-23: Oxysterol binding protein inhibitors include [c-23.1] oxathiapiproline, [c-23.2] fluoxapiproline, and the like.
＜ｃ－２４：ＤＭＩ剤（脱メチル化阻害剤）＞
　ｃ－２４：ＤＭＩ剤（脱メチル化阻害剤）として、［ｃ－２４．１］アザコナゾール（ａｚａｃｏｎａｚｏｌｅ）、［ｃ－２４．２］ビテルタノール（ｂｉｔｅｒｔａｎｏｌ）、［ｃ－２４．３］ブロムコナゾール（ｂｒｏｍｕｃｏｎａｚｏｌｅ）、［ｃ－２４．４］シプロコナゾール（ｃｙｐｒｏｃｏｎａｚｏｌｅ）、［ｃ－２４．５］ジフェノコナゾール（ｄｉｆｅｎｏｃｏｎａｚｏｌｅ）、［ｃ－２４．６］ジニコナゾール（ｄｉｎｉｃｏｎａｚｏｌｅ）、［ｃ－２４．７］ジニコナゾールＭ（ｄｉｎｉｃｏｎａｚｏｌｅ－Ｍ）、［ｃ－２４．８］エポキシコナゾール（ｅｐｏｘｉｃｏｎａｚｏｌｅ）、［ｃ－２４．９］エタコナゾール（ｅｔａｃｏｎａｚｏｌｅ）、［ｃ－２４．１０］フェナリモル（ｆｅｎａｒｉｍｏｌ）、［ｃ－２４．１１］フェンブコナゾール（ｆｅｎｂｕｃｏｎａｚｏｌｅ）、［ｃ－２４．１２］フルキンコナゾール（ｆｌｕｑｕｉｎｃｏｎａｚｏｌｅ）、［ｃ－２４．１３］キンコナゾール（ｑｕｉｎｃｏｎａｚｏｌｅ）、［ｃ－２４．１４］フルシラゾール（ｆｌｕｓｉｌａｚｏｌｅ）、［ｃ－２４．１５］フルトリアホール（ｆｌｕｔｒｉａｆｏｌ）、［ｃ－２４．１６］ヘキサコナゾール（ｈｅｘａｃｏｎａｚｏｌｅ）、［ｃ－２４．１７］イマザリル（ｉｍａｚａｌｉｌ）、［ｃ－２４．１８］イミベンコナゾール（ｉｍｉｂｅｎｃｏｎａｚｏｌｅ）、［ｃ－２４．１９］イプコナゾール（ｉｐｃｏｎａｚｏｌｅ）、［ｃ－２４．２０］メトコナゾール（ｍｅｔｃｏｎａｚｏｌｅ）、［ｃ－２４．２１］ミクロブタニル（ｍｙｃｌｏｂｕｔａｎｉｌ）、［ｃ－２４．２２］ヌアリモール（ｎｕａｒｉｍｏｌ）、［ｃ－２４．２３］オキスポコナゾール（ｏｘｐｏｃｏｎａｚｏｌｅ）、［ｃ－２４．２４］オキスポコナゾールフマル酸塩（ｏｘｐｏｃｏｎａｚｏｌｅ　ｆｕｍａｒａｔｅ）、［ｃ－２４．２５］ペフラゾエート（ｐｅｆｕｒａｚｏａｔｅ）、［ｃ－２４．２６］ペンコナゾール（ｐｅｎｃｏｎａｚｏｌｅ）、［ｃ－２４．２７］プロクロラズ（ｐｒｏｃｈｌｏｒａｚ）、［ｃ－２４．２８］プロピコナゾール（ｐｒｏｐｉｃｏｎａｚｏｌｅ）、［ｃ－２４．２９］プロチオコナゾール（ｐｒｏｔｈｉｏｃｏｎａｚｏｌｅ）、［ｃ－２４．３０］ピリフェノックス（ｐｙｒｉｆｅｎｏｘ）、［ｃ－２４．３１］ピリソキサゾール（ｐｙｒｉｓｏｘａｚｏｌｅ）、［ｃ－２４．３２］シメコナゾール（ｓｉｍｅｃｏｎａｚｏｌｅ）、［ｃ－２４．３３］テブコナゾール（ｔｅｂｕｃｏｎａｚｏｌｅ）、［ｃ－２４．３４］テトラコナゾール（ｔｅｔｒａｃｏｎａｚｏｌｅ）、［ｃ－２４．３５］トリアジメホン（ｔｒｉａｄｉｍｅｆｏｎ）、［ｃ－２４．３６］トリアジメノール（ｔｒｉａｄｉｍｅｎｏｌ）、［ｃ－２４．３７］トリフルミゾール（ｔｒｉｆｌｕｍｉｚｏｌｅ）、［ｃ－２４．３８］トリホリン（ｔｒｉｆｏｒｉｎｅ）、［ｃ－２４．３９］トリチコナゾール（ｔｒｉｔｉｃｏｎａｚｏｌｅ）、［ｃ－２４．４０］メフェントリフルコナゾール（ｍｅｆｅｎｔｒｉｆｌｕｃｏｎａｚｏｌｅ）、［ｃ－２４．４１］イプフェントリフルコナゾール（ｉｐｆｅｎｔｒｉｆｌｕｃｏｎａｚｏｌｅ）等が挙げられる。 <c-24: DMI agents (demethylation inhibitors)>
c-24: DMI agents (demethylation inhibitors): [c-24.1] azaconazole, [c-24.2] bitertanol, [c-24.3] bromuconazole, [c-24.4] cyproconazole, [c-24.5] difenoconazole, [c-24.6] diniconazole [c-24.7] diniconazole M, [c-24.8] epoxyconazole, [c-24.9] etaconazole, [c-24.10] fenarimol, [c-24.11] fenbuconazole, [c-24.12] fluquinconazole [c-24.13] quinconazole, [c-24.14] flusilazole, [c-24.15] flutriafol, [c-24.16] hexaconazole, [c-24.17] imazalil, [c-24.18] imibenconazole azol, [c-24.19] ipconazole, [c-24.20] metconazole, [c-24.21] myclobutanil, [c-24.22] nuarimol, [c-24.23] oxpoconazole, [c-24.24] oxpoconazole fumarate fumarate), [c-24.25] pefurazoate, [c-24.26] penconazole, [c-24.27] prochloraz, [c-24.28] propiconazole, [c-24.29] prothioconazole, [c-24.30] pyrifenox, [c-24.31] pyrisoxazole, [c-24.32] simeconazole, [c-24.33] tebuconazole ole), [c-24.34] tetraconazole, [c-24.35] triadimefon, [c-24.36] triadimenol, [c-24.37] triflumizole, [c-24.38] triforine, [c-24.39] triticonazole, [c-24.40] mefentrifluconazole, [c-24.41] ipfentrifluconazole, and the like.
＜ｃ－２５：アミン系殺菌剤＞
　ｃ－２５：アミン系殺菌剤として、［ｃ－２５．１］アルジモルフ（ａｌｄｉｍｏｒｐｈ）、［ｃ－２５．２］ドデモルフ（ｄｏｄｅｍｏｒｐｈ）、［ｃ－２５．３］フェンプロピモルフ（ｆｅｎｐｒｏｐｉｍｏｒｐｈ）、［ｃ－２５．４］トリデモルフ（ｔｒｉｄｅｍｏｒｐｈ）、［ｃ－２５．５］フェンプロピジン（ｆｅｎｐｒｏｐｉｄｉｎ）、［ｃ－２５．６］ピペラリン（ｐｉｐｅｒａｌｉｎ）、［ｃ－２５．７］スピロキサミン（ｓｐｉｒｏｘａｍｉｎｅ）等が挙げられる。 <c-25: Amine-based disinfectants>
c-25: Amine fungicides include, for example, [c-25.1] aldimorph, [c-25.2] dodemorph, [c-25.3] fenpropimorph, [c-25.4] tridemorph, [c-25.5] fenpropidin, [c-25.6] piperalin, and [c-25.7] spiroxamine.
＜ｃ－２６：ステロール生合成のＣ４位脱メチル化における３－ケト還元酵素阻害剤＞
　ｃ－２６：ステロール生合成のＣ４位脱メチル化における３－ケト還元酵素阻害剤として、［ｃ－２６．１］フェンヘキサミド（ｆｅｎｈｅｘａｍｉｄ）、［ｃ－２６．２］フェンピラザミン（ｆｅｎｐｙｒａｚａｍｉｎｅ）等が挙げられる。 <c-26: 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis>
c-26: 3-keto reductase inhibitors in the C4 demethylation of sterol biosynthesis include [c-26.1] fenhexamid, [c-26.2] fenpyrazamine, and the like.
＜ｃ－２７：ステロール生合成のスクアレンエポキシダーゼ阻害剤＞
　ｃ－２７：ステロール生合成のスクアレンエポキシダーゼ阻害剤として、［ｃ－２７．１］ピリブチカルブ（ｐｙｒｉｂｕｔｉｃａｒｂ）、［ｃ－２７．２］ナフチフィン（ｎａｆｔｉｆｉｎｅ）、［ｃ－２７．３］テルビナフィン（ｔｅｒｂｉｎａｆｉｎｅ）等が挙げられる。 <c-27: Squalene epoxidase inhibitor in sterol biosynthesis>
c-27: Squalene epoxidase inhibitors of sterol biosynthesis include [c-27.1] pyributicarb, [c-27.2] naftifine, [c-27.3] terbinafine, and the like.
＜ｃ－２８：細胞壁生合成阻害剤＞
　ｃ－２８：細胞壁生合成阻害剤として、［ｃ－２８．１］ポリオキシン類（ｐｏｌｙｏｘｉｎｓ）、［ｃ－２８．２］ジメトモルフ（ｄｉｍｅｔｈｏｍｏｒｐｈ）、［ｃ－２８．３］フルモルフ（ｆｌｕｍｏｒｐｈ）、［ｃ－２８．４］ピリモルフ（ｐｙｒｉｍｏｒｐｈ）、［ｃ－２８．５］ベンチアバリカルブ（ｂｅｎｔｈｉａｖａｌｉｃａｒｂ）、［ｃ－２８．６］ベンチアバリカルブイソプロピル（ｂｅｎｔｈｉｖａｌｉｃａｒｂ－ｉｓｏｐｒｏｐｙｌ）、［ｃ－２８．７］イプロバリカルブ（ｉｐｒｏｖａｌｉｃａｒｂ）、［ｃ－２８．８］マンジプロパミド（ｍａｎｄｉｐｒｏｐａｍｉｄ）、［ｃ－２８．９］バリフェナレート（ｖａｌｉｆｅｎａｌａｔｅ）等が挙げられる。 <c-28: Cell wall biosynthesis inhibitor>
c-28: Cell wall biosynthesis inhibitors include, for example, [c-28.1] polyoxins, [c-28.2] dimethomorph, [c-28.3] flumorph, [c-28.4] pyrimorph, [c-28.5] benthiavalicarb, [c-28.6] benthiavalicarb-isopropyl, [c-28.7] iprovalicarb, [c-28.8] mandipropamid, and [c-28.9] valifenalate.
＜ｃ－２９：メラニン生合成阻害剤＞
　ｃ－２９：メラニン生合成阻害剤として、［ｃ－２９．１］フサライド（ｐｈｔｈａｌｉｄｅ　ｏｒ　ｆｔｈａｌｉｄｅ）、［ｃ－２９．２］ピロキロン（ｐｙｒｏｑｕｉｌｏｎｅ）、［ｃ－２９．３］トリシクラゾール（ｔｒｉｃｙｃｌａｚｏｌｅ）、［ｃ－２９．４］カルプロパミド（ｃａｒｐｒｏｐａｍｉｄ）、［ｃ－２９．５］ジクロシメット（ｄｉｃｌｏｃｙｍｅｔ）、［ｃ－２９．６］フェノキサニル（ｆｅｎｏｘａｎｉｌ）、［ｃ－２９．７］トルプロカルブ（ｔｏｌｐｒｏｃａｒｂ）等が挙げられる。 <c-29: Melanin biosynthesis inhibitor>
c-29: Melanin biosynthesis inhibitors include, for example, [c-29.1] phthalide or phthalide, [c-29.2] pyroquilone, [c-29.3] tricyclazole, [c-29.4] carpropamid, [c-29.5] diclocymet, [c-29.6] fenoxanil, and [c-29.7] tolprocarb.
＜ｃ－３０：宿主植物抵抗性誘導剤＞
　ｃ－３０：宿主植物抵抗性誘導剤として、［ｃ－３０．１］アシベンゾラルＳメチル（ａｃｉｂｅｎｚｏｌａｒ－Ｓ－ｍｅｔｈｙｌ）、［ｃ－３０．２］プロベナゾール（ｐｒｏｂｅｎａｚｏｌｅ）、［ｃ－３０．３］チアジニル（ｔｉａｄｉｎｉｌ）、［ｃ－３０．４］イソチアニル（ｉｓｏｔｉａｎｉｌ）、［ｃ－３０．５］ラミナリン（ｌａｍｉｎａｒｉｎ）、［ｃ－３０．６］オオイタドリ抽出液（ｅｘｔｒａｃｔ　ｆｒｏｍ　Ｒｅｙｎｏｕｔｒｉａ　ｓａｃｈａｌｉｎｅｎｓｉｓ　（ｇｉａｎｔ　ｋｎｏｔｗｅｅｄ）　）、［ｃ－３０．７］バチルス・マイコイデス分離株Ｊ（Ｂａｃｉｌｌｕｓ　ｍｙｃｏｉｄｅｓ　ｉｓｏｌａｔｅ　Ｊ　）、［ｃ－３０．８］サッカロミセス・セレビシアＬＡＳ１１７株の細胞壁（ｃｅｌｌ　ｗａｌｌｓ　ｏｆ　Ｓａｃｃｈａｒｏｍｙｃｅｓ　ｃｅｒｅｖｉｓｉａｅ　ｓｔｒａｉｎ　ＬＡＳ１１７ ）、［ｃ－３０．９］ホセチル（ｆｏｓｅｔｙｌ）、［ｃ－３０．１０］亜リン酸（ｐｈｏｓｐｈｏｒｏｕｓ　ａｃｉｄ）、［ｃ－３０．１１］亜リン酸のナトリウム塩（ｓｏｄｉｕｍ　ｐｈｏｓｐｈｉｔｅ）、［ｃ－３０．１２］亜リン酸のアンモニウム塩（ａｍｍｏｎｉｕｍ　ｐｈｏｓｐｈｉｔｅ）、［ｃ－３０．１３］亜リン酸のカリウム塩（ｐｏｔａｓｓｉｕｍ　ｐｈｏｓｐｈｉｔｅ）等が挙げられる。 <C-30: Host plant resistance inducer>
c-30: Host plant resistance inducers: [c-30.1] acibenzolar-S-methyl, [c-30.2] probenazole, [c-30.3] tiadinil, [c-30.4] isotianil, [c-30.5] laminarin, [c-30.6] extract from Reynoutria sachalinensis (giant knotweed), [c-30.7] Bacillus mycoides isolate J ), [c-30.8] cell walls of Saccharomyces cerevisiae strain LAS117, [c-30.9] fosetyl, [c-30.10] phosphorous acid, [c-30.11] sodium phosphorous acid, [c-30.12] ammonium phosphorous acid, [c-30.13] potassium phosphorous acid, and the like.
＜ｃ－３１：ジチオカーバメート系殺菌剤＞
　ｃ－３１：ジチオカーバメート系殺菌剤として、［ｃ－３１．１］マンコゼブ（ｍａｎｃｏｚｅｂ）、［ｃ－３１．２］マンゼブ（ｍａｎｚｅｂ）、［ｃ－３１．３］マンネブ（ｍａｎｅｂ）、［ｃ－３１．４］メチラム（ｍｅｔｉｒａｍ）、［ｃ－３１．５］プロピネブ（ｐｒｏｐｉｎｅｂ）、［ｃ－３１．６］チウラム（ｔｈｉｒａｍ）、［ｃ－３１．７］チアゾール亜鉛（ｚｉｎｃ　ｔｈｉａｚｏｌｅ　）、［ｃ－３１．８］ジネブ（ｚｉｎｅｂ）、［ｃ－３１．９］ジラム（ｚｉｒａｍ）、［ｃ－３１．１０］フェルバム（ｆｅｒｂａｍ）等が挙げられる。 <C-31: Dithiocarbamate fungicide>
c-31: Dithiocarbamate fungicides include, for example, [c-31.1] mancozeb, [c-31.2] manzeb, [c-31.3] maneb, [c-31.4] metiram, [c-31.5] propineb, [c-31.6] thiuram, [c-31.7] zinc thiazole, [c-31.8] zineb, [c-31.9] ziram, and [c-31.10] ferbam.
＜ｃ－３２：フタルイミド系殺菌剤＞
　ｃ－３２：フタルイミド系殺菌剤として、［ｃ－３２．１］キャプタン（ｃａｐｔａｎ）、［ｃ－３２．２］キャプタホール（ｃａｐｔａｆｏｌ）、［ｃ－３２．３］ホルペット（ｆｏｌｐｅｔ）、［ｃ－３２．４］フルオロホルペット（ｆｌｕｏｒｏｆｏｌｐｅｔ）等が挙げられる。 <C-32: Phthalimide fungicide>
c-32: Phthalimide fungicides include, for example, [c-32.1] captan, [c-32.2] captafol, [c-32.3] folpet, and [c-32.4] fluorofolpet.
＜ｃ－３３：グアニジン系殺菌剤＞
　ｃ－３３：グアニジン系殺菌剤として、［ｃ－３３．１］グアザチン（ｇｕａｚａｔｉｎｅ）、［ｃ－３３．２］イミノクタジン（ｉｍｉｎｏｃｔａｄｉｎｅ）、［ｃ－３３．３］イミノクタジンアルベシル酸塩（ｉｍｉｎｏｃｔａｄｉｎｅ　ａｌｂｅｓｉｌａｔｅ）、［ｃ－３３．４］イミノクタジン三酢酸塩（ｉｍｉｎｏｃｔａｄｉｎｅ　ｔｒｉａｃｅｔａｔｅ）等が挙げられる。 <C-33: Guanidine-based fungicide>
c-33: Guanidine fungicides include, for example, [c-33.1] guazatine, [c-33.2] iminoctadine, [c-33.3] iminoctadine albesilate, and [c-33.4] iminoctadine triacetate.
＜ｃ－３４：多作用点接触活性型殺菌剤＞
　ｃ－３４：多作用点接触活性型殺菌剤として、［ｃ－３４．１］クロロタロニル（ｃｈｌｏｒｏｔｈａｌｏｎｉｌ）、［ｃ－３４．２］ジクロフルアニド（ｄｉｃｈｌｏｆｌｕａｎｉｄ）、［ｃ－３４．３］トリルフルアニド（ｔｏｌｙｌｆｌｕａｎｉｄ）、［ｃ－３４．４］塩基性塩化銅（ｃｏｐｐｅｒ　ｏｘｙｃｈｌｏｒｉｄｅ）、［ｃ－３４．５］水酸化第二銅（ｃｏｐｐｅｒ　ＩＩ　ｈｙｄｒｏｘｉｄｅ）、［ｃ－３４．６］塩基性硫酸銅（ｃｏｐｐｅｒ　ｈｙｄｒｏｘｉｄｅ　ｓｕｌｆａｔｅ）、［ｃ－３４．７］有機銅化合物（ｏｒｇａｎｏｃｏｐｐｅｒ　ｃｏｍｐｏｕｎｄ）、［ｃ－３４．８］ドデシルベンゼンスルホン酸ビスエチレンジアミン銅錯塩［ＩＩ］dｏｄｅｃｙｌｂｅｎｚｅｎｅｓｕｌｐｈｏｎｉｃ　ａｃｉｄ　ｂｉｓｅｔｈｙｌｅｎｅｄｉａｍｉｎｅ　ｃｏｐｐｅｒ　［ＩＩ］　ｓａｌｔ）、［ｃ－３４．９］硫黄（ｓｕｌｐｈｕｒ）、［ｃ－３４．１０］フルオルイミド（ｆｌｕｏｒｏｉｍｉｄｅ）、［ｃ－３４．１１］アニラジン（ａｎｉｌａｚｉｎｅ）、［ｃ－３４．１２］ジチアノン（ｄｉｔｈｉａｎｏｎ）、［ｃ－３４．１３］キノメチオナート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ　ｏｒ　ｑｕｉｎｏｍｅｔｈｉｏｎａｔｅ）、［ｃ－３４．１４］メタスルホカルブ（ｍｅｔｈａｓｕｌｆｏｃａｒｂ）等が挙げられる。 <C-34: Multi-site contact-activated fungicide>
c-34: As a multi-site contact-activated fungicide, [c-34.1] chlorothalonil, [c-34.2] dichlofluanid, [c-34.3] tolylfluanid, [c-34.4] basic copper chloride, [c-34.5] copper II hydroxide, [c-34.6] basic copper sulfate, [c-34.7] organocuprolide compound), [c-34.8] dodecylbenzenesulphonic acid bisethylenediamine copper complex salt [II] dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt), [c-34.9] sulfur, [c-34.10] fluoroimide, [c-34.11] anilazine, [c-34.12] dithianon, [c-34.13] chinomethionate or quinomethionate, [c-34.14] methasulfocarb, and the like.
＜ｃ－３５：複数の作用機構を有する生物農薬＞
　ｃ－３５：複数の作用機構を有する生物農薬として、［ｃ－３５．１］ハウチワマメ苗木の子葉からの抽出物（ＢＬＡＤ）、［ｃ－３５．２］Ｓｗｉｎｇｌｅａ　ｇｌｕｔｉｎｏｓａからの抽出物（ｅｘｔｒａｃｔ　ｆｒｏｍ　Ｓｗｉｎｇｌｅａ　ｇｌｕｔｉｎｏｓａ）、［ｃ－３５．３］トリコデルマ・アトロビリデＩ－１２３７株（Ｔｒｉｃｈｏｄｅｒｍａ　ａｔｒｏｖｉｒｉｄｅ　ｓｔｒａｉｎ　Ｉ－１２３７）、［ｃ－３５．４］トリコデルマ・アトロビリデＬＵ１３２株（Ｔｒｉｃｈｏｄｅｒｍａ　ａｔｒｏｖｉｒｉｄｅ　ｓｔｒａｉｎ　ＬＵ１３２）、［ｃ－３５．５］トリコデルマ・アトロビリデＳＣ１株（Ｔｒｉｃｈｏｄｅｒｍａ　ａｔｒｏｖｉｒｉｄｅ　ｓｔｒａｉｎ　ＳＣ１）、［ｃ－３５．６］トリコデルマ・アスペレルムＴ３４株（Ｔｒｉｃｈｏｄｅｒｍａ　ａｓｐｅｒｅｌｌｕｍ　ｓｔｒａｉｎ　Ｔ３４）、［ｃ－３５．７］グリオクラディウム・カテナラタムＪ１４４６株（Ｇｌｉｏｃｌａｄｉｕｍ　ｃａｔｅｎｕｌａｔｕｍ　ｓｔｒａｉｎ　Ｊ１４４６）、［ｃ－３５．８］クロノスタキス・ロゼアＣＲ－７株（Ｃｌｏｎｏｓｔａｃｈｙｓ　ｒｏｓｅａ　ｓｔｒａｉｎ　ＣＲ－７）、［ｃ－３５．９］バチルス・アミロリクエファシエンス　ＱＳＴ７１３株（Ｂａｃｉｌｌｕｓ　ａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ　ｓｔｒａｉｎ　ＱＳＴ７１３）、［ｃ－３５．１０］バチルス・アミロリクエファシエンス　ＦＺＢ２４株（Ｂａｃｉｌｌｕｓ　ａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ　ｓｔｒａｉｎ　ＦＺＢ２４）、［ｃ－３５．１１］バチルス・アミロリクエファシエンス　ＭＢＩ６００株（Ｂａｃｉｌｌｕｓ　ａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ　ｓｔｒａｉｎ　ＭＢＩ６００）、［ｃ－３５．１２］バチルス・アミロリクエファシエンス　Ｄ７４７株（Ｂａｃｉｌｌｕｓ　ａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ　ｓｔｒａｉｎ　Ｄ７４７）、［ｃ－３５．１３］バチルス・アミロリクエファシエンス　Ｆ７２７株（Ｂａｃｉｌｌｕｓ　ａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ　ｓｔｒａｉｎ　Ｆ７２７）、［ｃ－３５．１４］バチルス・ズブチリス ＡＦＳ０３２３２１株（Ｂａｃｉｌｌｕｓ　ｓｕｂｔｉｌｉｓ　ｓｔｒａｉｎ　ＡＦＳ０３２３２１）、［ｃ－３５．１５］シュードモナス・クロロファフィス　ＡＦＳ００９株（Ｐｓｅｕｄｏｍｏｎａｓ　ｃｈｌｏｒｏｒａｐｈｉｓ　ｓｔｒａｉｎ　ＡＦＳ００９）、［ｃ－３５．１６］ストレプトミセス・グリセオビリデス　Ｋ６１株（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｇｒｉｓｅｏｖｉｒｉｄｅｓ　ｓｔｒａｉｎ　Ｋ６１）、［ｃ－３５．１７］ストレプトミセス・リディクス　ＷＹＥＣ１０８株（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｌｙｄｉｃｕｓ　ｓｔｒａｉｎ　ＷＹＥＣ１０８）等が挙げられる。 <C-35: Biological pesticides with multiple modes of action>
c-35: As a biological control agent having multiple modes of action, [c-35.1] extract from cotyledons of lupin seedlings (BLAD), [c-35.2] extract from Swinglea glutinosa, [c-35.3] Trichoderma atroviride strain I-1237, [c-35.4] Trichoderma atroviride strain LU132, [c-35.5] Trichoderma atroviride strain SC1 strain SC1), [c-35.6] Trichoderma asperellum strain T34, [c-35.7] Gliocladium catenulatum strain J1446, [c-35.8] Clonostachys rosea strain CR-7, [c-35.9] Bacillus amyloliquefaciens strain QST713, [c-35.10] Bacillus amyloliquefaciens FZB24 strain (Bacillus amyloliquefaciens strain FZB24), [c-35.11] Bacillus amyloliquefaciens MBI600 strain (Bacillus amyloliquefaciens strain MBI600), [c-35.12] Bacillus amyloliquefaciens D747 strain (Bacillus amyloliquefaciens strain D747), [c-35.13] Bacillus amyloliquefaciens F727 strain (Bacillus amyloliquefaciens strain F727), [c-35.14] Bacillus subtilis strain AFS032321, [c-35.15] Pseudomonas chlororaphis strain AFS009, [c-35.16] Streptomyces griseovirides strain K61, [c-35.17] Streptomyces lydicus strain WYEC108, and the like.
＜ｃ－３６：その他の殺菌剤＞
　ｃ－３６：その他の殺菌剤として、［ｃ－３６．１］テクロフタラム（ｔｅｃｌｏｆｔａｌａｍ）、［ｃ－３６．２］トリアゾキシド（ｔｒｉａｚｏｘｉｄｅ）、［ｃ－３６．３］フルスルファミド（ｆｌｕｓｕｌｆａｍｉｄｅ）、［ｃ－３６．４］ジクロメジン（ｄｉｃｌｏｍｅｚｉｎｅ）、［ｃ－３６．５］シフルフェナミド（ｃｙｆｌｕｆｅｎａｍｉｄ）、［ｃ－３６．６］ドジン（ｄｏｄｉｎｅ）、［ｃ－３６．７］フルチアニル（ｆｌｕｔｉａｎｉｌ）、［ｃ－３６．８］テブフロキン（ｔｅｂｕｆｌｏｑｕｉｎ）、［ｃ－３６．９］バリダマイシン類（ｖａｌｉｄａｍｙｃｉｎｓ）、［ｃ－３６．１０］シモキサニル（ｃｙｍｏｘａｎｉｌ）、［ｃ－３６．１１］ピカルブトラゾクス（ｐｉｃａｒｂｕｔｒａｚｏｘ）、［ｃ－３６．１２］キノフメリン（ｑｕｉｎｏｆｕｍｅｌｉｎ）、［ｃ－３６．１３］アミノピリフェン（ａｍｉｎｏｐｙｒｉｆｅｎ）、［ｃ－３６．１４］ピリダクロメチル（ｐｙｒｉｄａｃｈｌｏｍｅｔｙｌ）、［ｃ－３６．１５］イプフルフェノキン（ｉｐｆｌｕｆｅｎｏｑｕｉｎ）、［ｃ－３６．１６］フロリルピコキサミド（ｆｌｏｒｙｌｐｉｃｏｘａｍｉｄ）、［ｃ－３６．１７］ジクロベンチアゾクス（ｄｉｃｈｌｏｂｅｎｔｉａｚｏｘ）、［ｃ－３６．１８］ピラプロポイン（ｐｙｒａｐｒｏｐｏｙｎｅ）、［ｃ－３６．１９］ジピメチトロン（ｄｉｐｙｍｅｔｉｔｒｏｎｅ）、［ｃ－３６．２０］Ｄ－タガトース（Ｄ－ｔａｇａｔｏｓｅ）、［ｃ－３６．２１］マシン油、有機油、無機塩類、天然物起源（ｍｉｎｅｒａｌ　ｏｉｌｓ，　ｏｒｇａｎｉｃ　ｏｉｌｓ，　ｉｎｏｒｇａｎｉｃ　ｓａｌｔｓ，　ｍａｔｅｒｉａｌ　ｏｆ　ｂｉｏｌｏｇｉｃａｌ　ｏｒｉｇｉｎ）、［ｃ－３６．２２］クロロインコナジド（Ｃｈｌｏｒｏｉｎｃｏｎａｚｉｄｅ）、［ｃ－３６．２３］フルベネテラム（Ｆｌｕｂｅｎｅｔｅｒａｍ）、 <C-36: Other fungicides>
c-36: Other fungicides include, [c-36.1] tecloftalam, [c-36.2] triazoxide, [c-36.3] flusulfamide, [c-36.4] diclomezine, [c-36.5] cyflufenamid, [c -36.6] dodine, [c-36.7] flutianil, [c-36.8] tebufloquin, [c-36.9] validamycins, [c-36.10] cymoxanil, [c-36.11] picarbutrazox, [c -36.12] Quinofumelin, [c-36.13] Aminopyrifen, [c-36.14] Pyridaclomethyl, [c-36.15] Ipflufenoquin, [c-36.16] Florylpicoxamid , [c-36.17] dichlobentiazox, [c-36.18] pyrapropoyne, [c-36.19] dipimethitrone, [c-36.20] D-tagatose, [c-36.21] machine oil, organic oil, inorganic salts, material of biological origin, [c-36.22] chloroinconazide, [c-36.23] fulveneteram,
［ｃ－３６．２４］式（ｓ１６）
Figure JPOXMLDOC01-appb-C000120
で表される化合物（国際公開第９８／０４６６０７号参照）、 [c-36.24] Formula (s16)
Figure JPOXMLDOC01-appb-C000120
(see International Publication No. WO 98/046607),
［ｃ－３６．２５］式（ｓ１７）
Figure JPOXMLDOC01-appb-C000121
で表される化合物（ｇｏｕｇｅｒｏｔｉｎ）、 [c-36.25] Formula (s17)
Figure JPOXMLDOC01-appb-C000121
A compound represented by the formula (gougerotin),
［ｃ－３６．２６］式（ｓ１８）
Figure JPOXMLDOC01-appb-C000122
で表される化合物（ｎｉｎｇｎａｎｍｙｃｉｎ）、 [c-36.26] Formula (s18)
Figure JPOXMLDOC01-appb-C000122
A compound represented by the formula (ningnanmycin):
［ｃ－３６．２７］式（ｓ１９）
Figure JPOXMLDOC01-appb-C000123
で表される化合物（国際公開第２０１１／０８５０８４号参照）、 [c-36.27] Formula (s19)
Figure JPOXMLDOC01-appb-C000123
A compound represented by the formula (see International Publication No. WO 2011/085084),
［ｃ－３６．２８］式（ｓ２０）
Figure JPOXMLDOC01-appb-C000124
で表される化合物（国際公開第２０１１／１３７００２号参照）、 [c-36.28] Formula (s20)
Figure JPOXMLDOC01-appb-C000124
A compound represented by the formula (see International Publication No. WO 2011/137002),
［ｃ－３６．２９］式（ｓ２１）
Figure JPOXMLDOC01-appb-C000125
で表される化合物（国際公開第２００８／１１０３１３号参照）、 [c-36.29] Formula (s21)
Figure JPOXMLDOC01-appb-C000125
A compound represented by the formula (see International Publication No. WO 2008/110313),
［ｃ－３６．３０］式（ｓ２２）
Figure JPOXMLDOC01-appb-C000126
で表される化合物（国際公開第２００９／１５６０９８号参照）、 [c-36.30] Formula (s22)
Figure JPOXMLDOC01-appb-C000126
A compound represented by the formula (see International Publication No. WO 2009/156098),
［ｃ－３６．３１］式（ｓ２３）
Figure JPOXMLDOC01-appb-C000127
で表される化合物（国際公開第２０１６／１８７２０１号参照）、 [c-36.31] Formula (s23)
Figure JPOXMLDOC01-appb-C000127
A compound represented by the formula (see International Publication No. WO 2016/187201),
［ｃ－３６．３２］式（ｓ２４）
Figure JPOXMLDOC01-appb-C000128
で表される化合物（国際公開第２０１３／０９２２２４号参照）、 [c-36.32] Formula (s24)
Figure JPOXMLDOC01-appb-C000128
A compound represented by the formula (see International Publication No. WO 2013/092224),
［ｃ－３６．３３］式（ｓ２５）
Figure JPOXMLDOC01-appb-C000129
で表される化合物（国際公開第２０１５／１８５４８５号参照）、 [c-36.33] Formula (s25)
Figure JPOXMLDOC01-appb-C000129
A compound represented by the formula (see International Publication No. WO 2015/185485),
［ｃ－３６．３４］式（ｓ２６）
Figure JPOXMLDOC01-appb-C000130
で表される化合物（国際公開第２０１７／０９３３４８号参照）、 [c-36.34] Formula (s26)
Figure JPOXMLDOC01-appb-C000130
A compound represented by the formula (see International Publication No. 2017/093348),
［ｃ－３６．３５］式（ｓ２７）
Figure JPOXMLDOC01-appb-C000131
で表される化合物（国際公開第２０１２／０３１０６１号参照）、 [c-36.35] Formula (s27)
Figure JPOXMLDOC01-appb-C000131
A compound represented by the formula (see International Publication No. WO 2012/031061),
［ｃ－３６．３６］式（ｓ２８）
Figure JPOXMLDOC01-appb-C000132
［式中、Ａ1、Ａ2、Ａ３およびＡ4は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ5は、水素原子、アセチル基、またはベンゾイル基を表す。］で表される化合物（国際公開第２００６／０３１６３１号、国際公開第２０１０／０６９８８２号参照）、 [c-36.36] Formula (s28)
Figure JPOXMLDOC01-appb-C000132
[wherein A1, A2, A3 and A4 each independently represent a hydrogen atom or a halogen atom, and A5 represents a hydrogen atom, an acetyl group or a benzoyl group] (see WO 2006/031631 and WO 2010/069882),
［ｃ－３６．３７］式（ｓ２９）
Figure JPOXMLDOC01-appb-C000133
［式中、Ａ６は、Ｃ１～Ｃ６のハロアルキル基を表し、Ａ７およびＡ８は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第２０１４／０４３３７６号参照）、 [c-36.37] Formula (s29)
Figure JPOXMLDOC01-appb-C000133
[wherein A6 represents a C1-C6 haloalkyl group, and A7 and A8 each independently represent a hydrogen atom or a halogen atom] (see International Publication No. WO 2014/043376),
［ｃ－３６．３８］式（ｓ３０）
Figure JPOXMLDOC01-appb-C000134
［式中、Ａ９は、ハロゲン原子を表す。］で表される化合物（国際公開第２０１６／１５６２９０号参照）、 [c-36.38] Formula (s30)
Figure JPOXMLDOC01-appb-C000134
[In the formula, A9 represents a halogen atom.] (see International Publication No. 2016/156290),
［ｃ－３６．３９］式（ｓ３１）
Figure JPOXMLDOC01-appb-C000135
［式中、Ａ１０は、ハロゲン原子を表す。］で表される化合物（国際公開第２０１７／０２９１７９号参照）、 [c-36.39] Formula (s31)
Figure JPOXMLDOC01-appb-C000135
[In the formula, A10 represents a halogen atom.] (see International Publication No. 2017/029179),
［ｃ－３６．４０］式（ｓ３２）
Figure JPOXMLDOC01-appb-C000136
［式中、Ａ１１は、水素原子、またはハロゲン原子を表し、Ａ１２は、Ｃ１～Ｃ６のアルキル基を表す。］で表される化合物（国際公開第２０１１／０７０７７１号参照）、 [c-36.40] Formula (s32)
Figure JPOXMLDOC01-appb-C000136
[wherein A11 represents a hydrogen atom or a halogen atom, and A12 represents a C1-C6 alkyl group] (see International Publication No. WO 2011/070771),
［ｃ－３６．４１］式（ｓ３３）
Figure JPOXMLDOC01-appb-C000137
［式中、Ａ１３およびＡ１４は、ハロゲン原子を表す。］で表される化合物（国際公開第２０１１／０７０７７１号参照）、 [c-36.41] Formula (s33)
Figure JPOXMLDOC01-appb-C000137
[wherein A13 and A14 represent halogen atoms] (see International Publication No. WO 2011/070771),
［ｃ－３６．４２］式（ｓ３４）
Figure JPOXMLDOC01-appb-C000138
［式中、Ａ１５は、水素原子、またはハロゲン原子を表し、Ａ１６は、メチル基、エチル基、またはプロピル基を表す。］で表される化合物（国際公開第２０１４／０９５６７５号参照） [c-36.42] Formula (s34)
Figure JPOXMLDOC01-appb-C000138
[In the formula, A15 represents a hydrogen atom or a halogen atom, and A16 represents a methyl group, an ethyl group, or a propyl group.] (see International Publication No. WO 2014/095675)
［ｃ－３６．４３］式（ｓ３５）
Figure JPOXMLDOC01-appb-C000139
［式中、Ａ１７は、水素原子またはハロゲン原子を表し、Ｖ１およびＶ２は、それぞれ独立していて酸素原子または硫黄原子を表す。］で表される化合物（国際公開第２０１２／０２５４５０号参照） [c-36.43] Formula (s35)
Figure JPOXMLDOC01-appb-C000139
[wherein A17 represents a hydrogen atom or a halogen atom, and V1 and V2 each independently represent an oxygen atom or a sulfur atom] (see International Publication No. WO 2012/025450).
［ｃ－３６．４４］式（ｓ３６）
Figure JPOXMLDOC01-appb-C000140
［式中、Ａ１８は、水素原子またはフッ素原子を表す。］で表される化合物（国際公開第２０１６／０２４３５０号参照） [c-36.44] Formula (s36)
Figure JPOXMLDOC01-appb-C000140
[In the formula, A18 represents a hydrogen atom or a fluorine atom.] (see International Publication No. WO 2016/024350)
［ｃ－３６．４５］式（ｓ３７）
Figure JPOXMLDOC01-appb-C000141
［式中、Ａ１９は、Ｃ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第２０１８／１６９０３８号参照）、 [c-36.45] Formula (s37)
Figure JPOXMLDOC01-appb-C000141
[In the formula, A19 represents a C1 to C6 alkoxy group.] (see International Publication No. 2018/169038),
［ｃ－３６．４６］式（ｓ３８）
Figure JPOXMLDOC01-appb-C000142
［式中、Ａ２０は、メチル基またはメトキシ基を表し、Ａ２１は、メチル基、またはジフルオロメチル基を表す。］で表される化合物（国際公開第２０１７／０１６９１５号参照） [c-36.46] Formula (s38)
Figure JPOXMLDOC01-appb-C000142
[In the formula, A20 represents a methyl group or a methoxy group, and A21 represents a methyl group or a difluoromethyl group.] (see International Publication No. 2017/016915)
［ｃ－３６．４７］式（ｓ３９）
Figure JPOXMLDOC01-appb-C000143
［式中、Ａ２２は、水素原子またはハロゲン原子を表し、Ａ２３は、エチル基またはプロピル基を表す。］で表される化合物（国際公開第２０１８／１９７６９２号参照） [c-36.47] Formula (s39)
Figure JPOXMLDOC01-appb-C000143
[In the formula, A22 represents a hydrogen atom or a halogen atom, and A23 represents an ethyl group or a propyl group.] (see International Publication No. WO 2018/197692)
［ｃ－３６．４８］式（ｓ４０）
Figure JPOXMLDOC01-appb-C000144
［式中、Ａ２４は、水素原子またはハロゲン原子を表し、Ａ２５は、メチル基、フッ素原子または塩素原子を表す。］で表される化合物（国際公開第２０１６／１５６０８５号参照）、 [c-36.48] Formula (s40)
Figure JPOXMLDOC01-appb-C000144
[wherein A24 represents a hydrogen atom or a halogen atom, and A25 represents a methyl group, a fluorine atom, or a chlorine atom] (see International Publication No. WO 2016/156085),
［ｃ－３６．４９］式（ｓ４１）
Figure JPOXMLDOC01-appb-C000145
［式中、Ａ２６は、メチル基、フッ素原子または塩素原子を表す。］で表される化合物（国際公開第２０１７／０２５５１０号参照）、 [c-36.49] Formula (s41)
Figure JPOXMLDOC01-appb-C000145
[In the formula, A26 represents a methyl group, a fluorine atom, or a chlorine atom.] (see International Publication No. WO 2017/025510),
［ｃ－３６．５０］式（ｓ４２）
Figure JPOXMLDOC01-appb-C000146
［式中、Ａ２７は、水素原子またはメチル基を表す。］で表される化合物（国際公開第２０１７／１５３３８０号参照）、 [c-36.50] Formula (s42)
Figure JPOXMLDOC01-appb-C000146
[In the formula, A27 represents a hydrogen atom or a methyl group.] (see International Publication No. 2017/153380),
［ｃ－３６．５１］式（ｓ４３）
Figure JPOXMLDOC01-appb-C000147
［式中、Ａ２８は、水素原子またはメチル基を表し、Ａ２９は、イソプロピル基またはトリフルオロメチル基を表す。］で表される化合物（国際公開第２０１８／１７２１３３号参照）、 [c-36.51] Formula (s43)
Figure JPOXMLDOC01-appb-C000147
[In the formula, A28 represents a hydrogen atom or a methyl group, and A29 represents an isopropyl group or a trifluoromethyl group.] (see International Publication No. 2018/172133),
［ｃ－３６．５２］式（ｓ４４）
Figure JPOXMLDOC01-appb-C000148
［式中、Ａ３０は、水素原子またはメトキシ基を表し、Ａ３１は、エチル基またはシクロプロピル基を表す。］で表される化合物（国際公開第２０１７／０５５４６９号参照）等が挙げられる。 [c-36.52] Formula (s44)
Figure JPOXMLDOC01-appb-C000148
[In the formula, A30 represents a hydrogen atom or a methoxy group, and A31 represents an ethyl group or a cyclopropyl group.] (see WO 2017/055469).
　本発明化合物と他の殺虫剤、殺菌剤との混合物における、本発明化合物と他の殺虫剤、殺菌剤の混合割合は、特に限定されないが、例えば、本発明化合物：他の殺虫剤、殺菌剤が、０．０１：１００～１００：０．０１、０．１：１００～１００：０．１、１：１００～１００：１、１：１０～１０：１、または１：１（何れも重量換算）である。さらに、これらの上限値と下限値の任意の組み合わせの範囲も混合割合として含まれる。他の殺虫剤、殺菌剤が２種以上ある場合は、上記の混合割合は、本発明の化合物に対する、他の殺虫剤、殺菌剤の合計値の割合を指すものとする。 The mixing ratio of the compound of the present invention to the other insecticide or fungicide in a mixture of the compound of the present invention and the other insecticide or fungicide is not particularly limited, but may be, for example, the compound of the present invention:other insecticide or fungicide ratio of 0.01:100-100:0.01, 0.1:100-100:0.1, 1:100-100:1, 1:10-10:1, or 1:1 (all by weight). Furthermore, any combination of these upper and lower limit values is also included as the mixing ratio. When there are two or more kinds of other insecticides or fungicides, the above mixing ratio refers to the ratio of the total value of the other insecticides or fungicides to the compound of the present invention.
　本発明化合物は、双翅目害虫（アカイエカ、チカイエカ、ユスリカ、イエバエ、チョウバエ、ウシアブ等）、網翅目害虫（チャバネゴキブリ、クロゴキブリ、ワモンゴキブリ等）等の衛生害虫に対して顕著な駆除効果を有するものである。
　さらに本発明化合物は、直接の危害を与える節足動物類あるいは病気の媒介者である節足動物類等の駆虫剤として、それらの害生物が潜在しうる周囲の環境に対して、油剤や、乳剤、水和剤等の散布・注入・灌注・塗布、粉剤等の散布、薫蒸剤、蚊取線香・自己燃焼型燻煙剤、化学反応型煙霧剤等の加熱煙霧剤、フォッギング等の燻煙剤、ＵＬＶ剤等の処理、顆粒、錠剤及び毒餌の設置、またはフローティング粉剤、粒剤等の水路、井戸、貯水池、貯水槽及びその他の流水もしくは停留水中への滴下等の方法で利用することもできる。さらに、農業、森林害虫でもあるドクガ類等に対しては、前記した方法と同様に防除することが可能であり、またはハエ類等に対しては家畜の飼料中に混入して糞に混じるようにする方法、カ類等に対しては電気蚊取器等で空中へ揮散させる方法等も有効である。
　なお、これらの使用形態である製剤は、他の活性化合物、例えば殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、忌避剤または共力剤との混合剤として存在することもでき、これらの製剤は、本発明の化合物を合計量で、例えば、０．０００１重量％～９５重量％含有することが適当である。
　本発明化合物は、ネコノミ、イヌノミ、フタトゲチマダニ、糸状虫科（Ｆｉｌａｒｉｉｄａｅ）線虫類等の、家畜及び愛玩動物等の人間以外の哺乳動物及び鳥類の外部または内部寄生虫を駆除することができる。 The compound of the present invention has a remarkable extermination effect against sanitary pests such as Diptera (Culex pipiens, Culex pipiens, midges, house flies, moth flies, horse flies, etc.) and Dictyoptera (Berber's cockroach, Smoky-brown cockroach, American cockroach, etc.).
Furthermore, the compound of the present invention can be used as an anthelmintic agent for arthropods that directly harm or arthropods that are vectors of diseases, in the surrounding environment where such harmful organisms may be latent, by spraying, injecting, irrigating, or applying oil solutions, emulsions, wettable powders, etc., spraying powders, etc., treating with heated aerosols such as fumigants, mosquito coils, self-burning type fumigants, chemical reaction type aerosols, fumigants such as fogging, ULV agents, etc., setting granules, tablets, and poison bait, or dropping floating powders, granules, etc. into waterways, wells, reservoirs, water tanks, and other running or standing water. Furthermore, for agricultural and forest pests such as tussock moths, it is possible to control them in the same manner as described above, or for flies, etc., a method of mixing the compound in livestock feed so that it mixes with feces, and for mosquitoes, a method of volatilizing the compound into the air using an electric mosquito repellent, etc. are also effective.
These formulations for use may also be present as mixtures with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, and these formulations suitably contain the compound of the present invention in a total amount of, for example, 0.0001% by weight to 95% by weight.
The compounds of the present invention can control external or internal parasites of mammals and birds other than humans, such as livestock and pets, including cat fleas, dog fleas, Haemaphysalis longicornis, and nematodes of the family Filariidae.
　外部・内部寄生虫の駆除は、経口投与、非経口的投与または経皮投与により達成される。経口投与としては、本発明化合物を少量、食事または飼料等に混入したり、適切な経口摂取可能な調合薬剤組成物等の経口投与剤、例えば、薬剤上許容しうる担体や、コーティング物質を含む錠剤、丸剤（丸薬）、カプセル剤、除放性大粒丸薬、ペースト剤、ゲル剤、薬用飲料、薬用飼料、薬用飲料水、動物飼料、薬用追餌、その他胃腸管内に保留されるようにした除放性デバイス等の経口投与剤として調製し、これらを家畜、ペットに経口的に投与したりすればよい。
　薬用飲料水として経口的に投与する場合、薬用飲料水は、普通ベントナイトのような懸濁剤あるいは湿潤剤またはその他の賦形剤と共に適当な非毒性の溶剤または水での溶解、懸濁液または分散液として調製すればよい。また、一般に薬用飲料水は、さらに消泡剤を含有する。薬用飲料水には、一般に本発明化合物を０．０１重量％～１．０重量％、好ましくは、０．０１重量％～０．１重量％を含有することができる。 The extermination of external and internal parasites can be achieved by oral administration, parenteral administration or transdermal administration. For oral administration, a small amount of the compound of the present invention can be mixed into food or feed, or can be prepared into oral administration agents such as suitable orally ingestible compounded pharmaceutical compositions, for example, tablets, pills, capsules, sustained release large pills, pastes, gels, medicated drinks, medicated feed, medicated drinking water, animal feed, medicated follow-up feed, and other sustained release devices that are retained in the gastrointestinal tract, which can be orally administered to livestock and pets.
When the compound is orally administered as medicinal drinking water, the medicinal drinking water may be prepared as a solution, suspension or dispersion in a suitable non-toxic solvent or water together with a suspending agent such as bentonite or a wetting agent or other excipients. In addition, medicinal drinking water generally further contains an antifoaming agent. The medicinal drinking water may generally contain the compound of the present invention in an amount of 0.01% by weight to 1.0% by weight, preferably 0.01% by weight to 0.1% by weight.
　乾燥した個体の単位使用形態で経口的に投与することが望ましい場合は、通常所定量の有効成分を含有するカプセル、丸薬または錠剤を用いる。これらの使用形態は、活性成分を適当に細粉砕した希釈剤、充填剤、崩壊剤及び／または結合剤、例えばデンプン、乳糖、タルク、ステアリン酸マグネシウム、植物性ゴム等と均質に混和することによって製造される。このような乾燥した固体の単位使用処方は、治療される宿主動物の種類、感染の程度及び寄生虫の種類及び宿主の体重によって駆虫剤の質量及び含量を広く変化させることができる。
　動物飼料によって投与する場合は、それを飼料に均質に分散させるか、トップドレッシングとして使用されるかペレットの形態として使用できる。普通望ましい抗寄生虫効果を達成するためには、最終飼料中に本発明化合物を、例えば、０．０００１重量％～０．０５重量％、好ましくは、０．０００５重量％～０．０１重量％を含有させることもできる。 When oral administration in dry solid unit dose form is desired, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These dose forms are prepared by intimately mixing the active ingredient with a suitable finely divided diluent, filler, disintegrant and/or binder, such as starch, lactose, talc, magnesium stearate, vegetable gums, etc. Such dry solid unit dose formulations can vary widely in mass and content of anthelmintic agent depending on the type of host animal to be treated, the degree of infection and the type of parasite and the weight of the host.
When administered via animal feed, it can be dispersed homogeneously in the feed, used as a top dressing or in the form of pellets. In order to achieve the normally desired antiparasitic effect, the compound of the invention can be present in the final feed in an amount of, for example, 0.0001% to 0.05% by weight, preferably 0.0005% to 0.01% by weight.
　経皮投与としては、スプレー、粉末、グリース、クリーム、軟膏、乳剤、ローション、スポットオン、ポアオン、シャンプー等の経皮投与剤として経皮投与または局所投与すればよい。経皮投与や局所投与の方法として、局部的または全身的に節足動物を防除するように動物に取り付けたデバイス（例えば首輪、メダリオンやイヤータッグ等）を利用することもできる。
　この様な経皮投与や局所投与の効果を達成するためには、一般に本発明の化合物で０．０００１重量％～０．１重量％、好ましくは、０．００１重量％～０．０１重量％を投与させればよい。なお、液体担体賦形剤に溶解あるいは分散させたものは、前胃内、筋肉内、気管内または皮下注射によって非経口的に動物に投与できる。非経口投与のために、活性化合物は好適には落花生油、綿実油のような適当な植物油と混合する。このような処方は、一般に本発明化合物を０．０５重量％～５０重量％、好ましくは、０．１重量％～５．０重量％を含有させることができる。また、ジメチルスルホキシドや、炭化水素溶剤のような適当な担体と混合することによって局所的に投与しうる。この製剤はスプレーまたは直接的注加によって動物の外部表面に直接適用される。 Transdermal administration may be by topical or percutaneous administration in the form of a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc. Transdermal or topical administration may also be accomplished by the use of a device (e.g., a collar, medallion, ear tag, etc.) attached to the animal for local or systemic arthropod control.
In order to achieve such effects of percutaneous or topical administration, the compound of the present invention may generally be administered at 0.0001% to 0.1% by weight, preferably 0.001% to 0.01% by weight. The compound dissolved or dispersed in a liquid carrier excipient may be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compound is preferably mixed with a suitable vegetable oil such as peanut oil or cottonseed oil. Such a formulation may generally contain the compound of the present invention at 0.05% to 50% by weight, preferably 0.1% to 5.0% by weight. The compound may also be administered topically by mixing with a suitable carrier such as dimethylsulfoxide or a hydrocarbon solvent. The formulation may be applied directly to the external surface of an animal by spraying or direct pouring.
　以下に、合成例、参考例、および試験例を挙げて、本発明を更に詳細に示すが、本発明はこれらに限定されるものではない。 The present invention will be described in more detail below with reference to synthesis examples, reference examples, and test examples, but the present invention is not limited to these.
［参考例１］
　３－エチル－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000149
　ナトリウムエトキシド（２０％エタノール溶液）　３８．７ｍｌに、２－ブタノン　８．９０ｍｌ、シュウ酸ジエチル　１３．５ｍｌ、およびエタノール　１００ｍｌの混合溶液を室温下にて加えた。次いで、この溶液を７０℃に昇温し、１時間３０分間撹拌した。得られた溶液に、ヒドラジン塩酸塩　７．５４ｇを加えて、加熱還流下、２．５時間攪拌した。室温まで冷却した後に、反応混合物に水と飽和炭酸水素ナトリウム水溶液を加えた。得られた反応混合物に酢酸エチルを加えて有機層を抽出した。有機層と水層を分液した後に、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が、９．３２ｇの橙色油状物として得られた。 [Reference Example 1]
Synthesis of ethyl 3-ethyl-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000149
A mixed solution of 8.90 ml of 2-butanone, 13.5 ml of diethyl oxalate, and 100 ml of ethanol was added to 38.7 ml of sodium ethoxide (20% ethanol solution) at room temperature. The solution was then heated to 70° C. and stirred for 1 hour and 30 minutes. 7.54 g of hydrazine hydrochloride was added to the resulting solution, and the mixture was stirred for 2.5 hours under heating and reflux. After cooling to room temperature, water and a saturated aqueous solution of sodium bicarbonate were added to the reaction mixture. Ethyl acetate was added to the resulting reaction mixture to extract the organic layer. After separating the organic layer and the aqueous layer, the resulting organic layer was washed with saturated saline and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 9.32 g of an orange oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．６３　（１Ｈ，　ｓ），　４．３８　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　２．７２　（２Ｈ，　ｑ，　Ｊ　＝　７．６　Ｈｚ），　１．３９　（３Ｈ，　ｔ，　Ｊ　＝　７．１　Ｈｚ），　１．２８　（３Ｈ，　ｔ，　Ｊ　＝　７．６　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 6.63 (1H, s), 4.38 (2H, q, J = 7.1 Hz), 2.72 (2H, q, J = 7.6 Hz), 1.39 (3H, t, J = 7.1 Hz), 1.28 (3H, t, J = 7.6 Hz).
［参考例２］
　３－エチル－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000150
　３－エチル－１Ｈ－ピラゾール－５－カルボン酸エチル　９．３２ｇとジメチル硫酸　６．３１ｍｌを含むジメチルホルムアミド溶液　４５．０ｍｌを７０℃まで昇温して２時間攪拌した。室温まで冷却した後に、この反応混合物に水と酢酸エチルを加えて有機層を抽出した。有機層と水層を分液後、得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が、６．９２ｇの黄色油状物として得られた。 [Reference Example 2]
Synthesis of ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000150
45.0 ml of a dimethylformamide solution containing 9.32 g of ethyl 3-ethyl-1H-pyrazole-5-carboxylate and 6.31 ml of dimethyl sulfate was heated to 70° C. and stirred for 2 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to extract the organic layer. After separating the organic layer from the aqueous layer, the obtained organic layer was washed with saturated saline and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 6.92 g of a yellow oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．６４　（１Ｈ，　ｓ），　４．３３　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．１２　（３Ｈ，　ｓ），　２．６４　（２Ｈ，　ｑ，　Ｊ　＝　７．６　Ｈｚ），　１．３７　（３Ｈ，　ｔ，　Ｊ　＝　７．１　Ｈｚ），　１．２４　（３Ｈ，　ｔ，　Ｊ　＝　７．６　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 6.64 (1H, s), 4.33 (2H, q, J = 7.1 Hz), 4.12 (3H, s), 2.64 (2H, q, J = 7.6 Hz), 1.37 (3H, t, J = 7.1 Hz), 1.24 (3H, t, J = 7.6 Hz).
［参考例３］
　４－ブロモ－３－エチル－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000151
　０℃に冷却した３－エチル－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチル　７．６４ｇを含むジクロロメタン溶液　７６．０ｍｌに、臭素　４．３０ｍｌを加えた。この溶液を室温まで昇温し、２５分間攪拌した。この反応混合物に１％チオ硫酸ナトリウム水溶液とジクロロメタンを加えて、有機層を抽出した。有機層と水層を分液後、得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１０．７ｇの無色油状物として得られた。 [Reference Example 3]
Synthesis of ethyl 4-bromo-3-ethyl-1-methyl-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000151
Bromine (4.30 ml) was added to a dichloromethane solution (76.0 ml) containing ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylate (7.64 g) cooled to 0°C. The solution was warmed to room temperature and stirred for 25 minutes. A 1% aqueous sodium thiosulfate solution and dichloromethane were added to the reaction mixture to extract the organic layer. The organic layer and the aqueous layer were separated, and the resulting organic layer was 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 a colorless oil (10.7 g).
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　４．４０　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．１１　（３Ｈ，　ｓ），　２．６５　（２Ｈ，　ｑ，　Ｊ　＝　７．５　Ｈｚ），　１．４２　（３Ｈ，　ｔ，　Ｊ　＝　７．０　Ｈｚ），　１．２４　（３Ｈ，　ｔ，　Ｊ　＝　７．６　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 4.40 (2H, q, J = 7.1 Hz), 4.11 (3H, s), 2.65 (2H, q, J = 7.5 Hz), 1.42 (3H, t, J = 7.0 Hz), 1.24 (3H, t, J = 7.6 Hz).
［参考例４］
　４－ブロモ－３－（１－ブロモエチル）－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000152
　４－ブロモ－３－エチル－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチル　７．０４ｇ、Ｎ－ブロモスクシンイミド　５．２８ｇとアゾビスイソブチロニトリル　２２１ｍｇ含むクロロベンゼン　７０ｍｌを加熱還流下にて１時間１０分間攪拌した。この反応混合物を室温まで冷却した後に、水とジクロロメタンを加えて有機層を抽出した。有機層と水層を分液後、得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物が１０．９ｇの黄褐色油状物として得られた。これ以上精製することなく、次の反応に使用した。 [Reference Example 4]
Synthesis of ethyl 4-bromo-3-(1-bromoethyl)-1-methyl-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000152
70 ml of chlorobenzene containing 7.04 g of ethyl 4-bromo-3-ethyl-1-methyl-1H-pyrazole-5-carboxylate, 5.28 g of N-bromosuccinimide, and 221 mg of azobisisobutyronitrile was stirred under reflux for 1 hour and 10 minutes. After cooling the reaction mixture to room temperature, water and dichloromethane were added to extract the organic layer. After separating the organic layer from the aqueous layer, the obtained organic layer was dried over sodium sulfate. After distilling off the solvent under reduced pressure, 10.9 g of the title compound was obtained as a yellow-brown oil. This was used in the next reaction without further purification.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　５．２４　（１Ｈ，　ｑ，　Ｊ　＝　７．０　Ｈｚ），　４．４１　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．１６　（３Ｈ，　ｓ），　２．１１　（３Ｈ，　ｄ，　Ｊ　＝　７．０　Ｈｚ），　１．４２　（３Ｈ，　ｔ，　Ｊ　＝　７．１　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 5.24 (1H, q, J = 7.0 Hz), 4.41 (2H, q, J = 7.1 Hz), 4.16 (3H, s), 2.11 (3H, d, J = 7.0 Hz), 1.42 (3H, t, J = 7.1 Hz).
［参考例５］
　３－アセチル－４－ブロモ－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000153
　参考例４で得られた４－ブロモ－３－（１－ブロモエチル）－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチル　１０．９ｇとＮ－メチルモルホリン－Ｎ－オキシド　９．４９ｇを含むアセトニトリル　９０ｍｌを１００℃にて２．５時間攪拌した。この反応混合物を室温まで冷却した後に、１％チオ硫酸ナトリウム水溶液と酢酸エチルを加えて有機層を抽出した。有機層と水層を分液後、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４．４２ｇの淡黄色固体として得られた。 [Reference Example 5]
Synthesis of ethyl 3-acetyl-4-bromo-1-methyl-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000153
10.9 g of ethyl 4-bromo-3-(1-bromoethyl)-1-methyl-1H-pyrazole-5-carboxylate obtained in Reference Example 4 and 9.49 g of N-methylmorpholine-N-oxide were contained in 90 ml of acetonitrile and stirred at 100° C. for 2.5 hours. After cooling the reaction mixture to room temperature, a 1% aqueous sodium thiosulfate solution and ethyl acetate were added to extract the organic layer. After separating the organic layer from the aqueous layer, the obtained organic layer was washed with saturated saline and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography. 4.42 g of the title compound was obtained as a pale yellow solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　４．４３　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　４．２２　（３Ｈ，　ｓ），　２．６０　（３Ｈ，　ｓ），　１．４４　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 4.43 (2H, q, J = 7.2 Hz), 4.22 (3H, s), 2.60 (3H, s), 1.44 (3H, t, J = 7.2 Hz).
［参考例６］
　４－ブロモ－３－（２－ブロモアセチル）－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000154
　３－アセチル－４－ブロモ－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチル　３．２１ｇとトリメチルフェニルアンモニウムトリブロミド　４．８２ｇを含むテトラヒドロフラン　３２．０ｍｌを５０℃にて２０分間攪拌した。この反応混合物を室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて洗浄した後に、有機層を抽出した。有機層と水層を分液後、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４．４１ｇの白色固体として得られた。 [Reference Example 6]
Synthesis of ethyl 4-bromo-3-(2-bromoacetyl)-1-methyl-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000154
32.0 ml of tetrahydrofuran containing 3.21 g of ethyl 3-acetyl-4-bromo-1-methyl-1H-pyrazole-5-carboxylate and 4.82 g of trimethylphenylammonium tribromide was stirred at 50° C. for 20 minutes. After cooling the reaction mixture to room temperature, water and ethyl acetate were added to the reaction mixture for washing, and the organic layer was extracted. After separating the organic layer from the aqueous layer, the obtained organic layer was washed with saturated saline and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography. 4.41 g of the title compound was obtained as a white solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　４．５５　（１Ｈ，　ｓ），　４．４４　（１Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．２４　（１Ｈ，　ｓ），　１．４４　（２Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 4.55 (1H, s), 4.44 (1H, q, J = 7.1 Hz), 4.24 (1H, s), 1.44 (2H, t, J = 7.2 Hz).
［参考例７］
　４－ブロモ－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000155
　参考例６で得られた４－ブロモ－３－（２－ブロモアセチル）－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチル　３．７３ｇと２－アミノ－４－（トリフルオロメチル）ピリジン　１．２１ｇを含むクロロベンゼン　１２．０ｍｌを加熱還流下で４時間攪拌した。この反応混合物を室温まで冷却した後に、飽和炭酸水素ナトリウム水溶液とジクロロメタンを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をジイソプロピルエーテルにて洗浄し、表題の化合物が２．２４ｇの黄色固体として得られた。 [Reference Example 7]
Synthesis of ethyl 4-bromo-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000155
3.73 g of ethyl 4-bromo-3-(2-bromoacetyl)-1-methyl-1H-pyrazole-5-carboxylate obtained in Reference Example 6 and 1.21 g of 2-amino-4-(trifluoromethyl)pyridine were stirred in 12.0 ml of chlorobenzene under heating and reflux for 4 hours. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium bicarbonate and dichloromethane were added and the mixture was separated. The organic layer obtained was dried over sodium sulfate. After distilling off the solvent under reduced pressure, the residue obtained was washed with diisopropyl ether to obtain 2.24 g of the title compound as a yellow solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．４４　（１Ｈ，　ｓ），　８．２７　（１Ｈ，　ｄ，　Ｊ　＝　７．２　Ｈｚ），　７．９８　（３Ｈ，　ｓ），　７．００　（１Ｈ，　ｄｄ，　Ｊ　＝　７．２，　１．７　Ｈｚ），　４．４６　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　４．３０　（３Ｈ，　ｓ），　１．４７　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 8.44 (1H, s), 8.27 (1H, d, J = 7.2 Hz), 7.98 (3H, s), 7.00 (1H, dd, J = 7.2, 1.7 Hz), 4.46 (2H, q, J = 7.2 Hz), 4.30 (3H, s), 1.47 (3H, t, J = 7.2 Hz).
［参考例８］
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000156
　４－ブロモ－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチル　２．３３ｇ、エタンチオール　２．１１ｍｌ、トリス(ジベンジリデンアセトン)ジパラジウム　１．０４ｇ、４，５－ビス（ジフェニルホスフィノ）－９，９－ジメチルキサンテン　１．３２ｇとジイソプロピルエチルアミン　４．９１ｍｌを含む１，４－ジオキサン　２３．０ｍｌを１１０℃にて６時間攪拌した。室温まで冷却した後に、この反応混合物に飽和塩化アンモニウムと酢酸エチルを加えた。得られた残渣をセライトにてろ過した後に、酢酸エチルでセライト残渣を洗浄した。有機層と水層を分液後、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が２．２１ｇの黄色固体として得られた。 [Reference Example 8]
Synthesis of ethyl 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000156
2.33 g of ethyl 4-bromo-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate, 2.11 ml of ethanethiol, 1.04 g of tris(dibenzylideneacetone)dipalladium, 1.32 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and 23.0 ml of 1,4-dioxane containing 4.91 ml of diisopropylethylamine were stirred at 110° C. for 6 hours. After cooling to room temperature, saturated ammonium chloride and ethyl acetate were added to the reaction mixture. The resulting residue was filtered through Celite, and the Celite residue was washed with ethyl acetate. After separation of the organic layer and the aqueous layer, the resulting organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 2.21 g of the title compound was obtained as a yellow solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．７１　（１Ｈ，　ｓ），　８．２７　（１Ｈ，　ｄ，　Ｊ　＝　７．０　Ｈｚ），　７．９６　（１Ｈ，　ｄ，　Ｊ　＝　０．９　Ｈｚ），　６．９８　（１Ｈ，　ｄｄ，　Ｊ　＝　７．０，　１．５　Ｈｚ），　４．４７　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．２６　（３Ｈ，　ｓ），　２．８２　（２Ｈ，　ｑ，　Ｊ　＝　７．３　Ｈｚ），　１．４７　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ），　１．１７　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 8.71 (1H, s), 8.27 (1H, d, J = 7.0 Hz), 7.96 (1H, d, J = 0.9 Hz), 6.98 (1H, dd, J = 7.0, 1.5 Hz), 4.47 (2H, q, J = 7.1 Hz), 4.26 (3H, s), 2.82 (2H, q, J = 7.3 Hz), 1.47 (3H, t, J = 7.2 Hz), 1.17 (3H, t, J = 7.3 Hz).
［参考例９］
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸の合成
Figure JPOXMLDOC01-appb-C000157
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチル　２．１２ｇと水酸化ナトリウム　４２４ｍｇを含むエタノール　２０．０ｍｌ、テトラヒドロフラン　１０．０ｍｌ、および水　２０．０ｍｌの混合溶液を室温下で３時間攪拌した。この反応混合物に、水とジクロロメタンを加えて分液した。得られた水層を１Ｎ塩酸水にて酸性にした後に、ジクロロメタンを加えて抽出した。有機層と水層を分液した後に、得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去し、表題の化合物が１．５７ｇの白色固体として得られた。 [Reference Example 9]
Synthesis of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylic acid
Figure JPOXMLDOC01-appb-C000157
A mixed solution of 2.12 g of ethyl 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate and 424 mg of sodium hydroxide in 20.0 ml of ethanol, 10.0 ml of tetrahydrofuran, and 20.0 ml of water was stirred at room temperature for 3 hours. Water and dichloromethane were added to this reaction mixture for separation. The resulting aqueous layer was acidified with 1N aqueous hydrochloric acid, and then extracted with dichloromethane. The organic layer and the aqueous layer were separated, and the resulting organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.57 g of the title compound as a white solid.
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　８．８８　（１Ｈ，　ｄ，　Ｊ　＝　７．１　Ｈｚ），　８．８２　（１Ｈ，　ｓ），　８．０６　（１Ｈ，　ｄ，　Ｊ　＝　０．７　Ｈｚ），　７．２５　（１Ｈ，　ｄｄ，　Ｊ　＝　７．２，　１．６　Ｈｚ），　４．１１　（３Ｈ，　ｓ），　２．８０　（２Ｈ，　ｑ，　Ｊ　＝　７．４　Ｈｚ），　１．０６　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1H -NMR (DMSO- D6 ) δ: 8.88 (1H, d, J = 7.1 Hz), 8.82 (1H, s), 8.06 (1H, d, J = 0.7 Hz), 7.25 (1H, dd, J = 7.2, 1.6 Hz), 4.11 (3H, s), 2.80 (2H, q, J = 7.4 Hz), 1.06 (3H, t, J = 7.3 Hz).
［合成例１］
　ｔ－ブチル（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）カルバメートの合成（化合物番号：８）
Figure JPOXMLDOC01-appb-C000158
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸　１．５７ｇ、トリエチルアミン　１．１９ｍｌとジフェニルリン酸アジド　１．８２ｍｌを含むｔ－ブチルアルコール　３０．０ｍｌの溶液を８０℃に昇温して、さらに３．５時間攪拌した。この反応混合物を室温まで冷却した後に、水と酢酸エチルを加えて抽出した。有機層と水層を分液した後に、得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去し、表題の化合物が０．９２ｇの白色固体として得られた。 [Synthesis Example 1]
Synthesis of t-butyl (4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (Compound No. 8)
Figure JPOXMLDOC01-appb-C000158
A solution of 30.0 ml of t-butyl alcohol containing 1.57 g of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylic acid, 1.19 ml of triethylamine, and 1.82 ml of diphenylphosphoryl azide was heated to 80° C. and stirred for an additional 3.5 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added for extraction. The organic layer and the aqueous layer were separated, and the obtained organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.92 g of the title compound as a white solid.
［合成例２］
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミンの合成（化合物番号：Ｉ－２）
Figure JPOXMLDOC01-appb-C000159
　ｔ－ブチル（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）カルバメート　９２０ｍｇ、トリフルオロ酢酸　１０．０ｍｌを含むジクロロメタン溶液　１０．０ｍｌを室温で２時間攪拌した。この反応混合物に飽和炭酸水素ナトリウム水溶液とジクロロメタンを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が５８３ｍｇの白色固体として得られた。 [Synthesis Example 2]
Synthesis of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-amine (Compound Number: I-2)
Figure JPOXMLDOC01-appb-C000159
A dichloromethane solution (10.0 ml) containing 920 mg of t-butyl (4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)carbamate and 10.0 ml of trifluoroacetic acid was stirred at room temperature for 2 hours. A saturated aqueous solution of sodium hydrogen carbonate and dichloromethane were added to this reaction mixture and the layers were separated. The resulting organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 583 mg of the title compound was obtained as a white solid.
［合成例３］
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）プロピオンアミドの合成（化合物番号：２７）
Figure JPOXMLDOC01-appb-C000160
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミン　６５．０ｍｇ、プロピオニルクロリド　４９．８μｌ、トリエチルアミン８０．１μｌを含むジクロロメタン１．００ｍｌを室温で２．５時間攪拌した。この溶液に、プロピオニルクロリド　４９．８μｌ、トリエチルアミン８０．１μｌを加えて、室温でさらに３０分間攪拌した。この反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が３１．４ｍｇの黄色固体として得られた。 [Synthesis Example 3]
Synthesis of N-(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)propionamide (Compound No. 27)
Figure JPOXMLDOC01-appb-C000160
1.00 ml of dichloromethane containing 65.0 mg of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-amine, 49.8 μl of propionyl chloride, and 80.1 μl of triethylamine was stirred at room temperature for 2.5 hours. 49.8 μl of propionyl chloride and 80.1 μl of triethylamine were added to this solution, and the mixture was stirred at room temperature for an additional 30 minutes. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to this reaction mixture, and the layers were separated. The organic layer obtained was washed with saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 31.4 mg of the title compound was obtained as a yellow solid.
［合成例４］
　Ｎ－（４－（エチルスルホニル）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）プロピオンアミドの合成（化合物番号：２９）
Figure JPOXMLDOC01-appb-C000161
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）プロピオンアミド　２０．０ｍｇ、３－クロロ過安息香酸（ｃａ．７０％純度）　３０．０ｍｇを含むジクロロメタン溶液　１ｍｌを室温で１．５時間攪拌した。この反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を、飽和炭酸水素ナトリウム水溶液にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１１．１ｍｇの黄色固体として得られた。 [Synthesis Example 4]
Synthesis of N-(4-(ethylsulfonyl)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)propionamide (Compound No. 29)
Figure JPOXMLDOC01-appb-C000161
1 ml of a dichloromethane solution containing 20.0 mg of N-(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)propionamide and 30.0 mg of 3-chloroperbenzoic acid (ca. 70% purity) was stirred at room temperature for 1.5 hours. Aqueous sodium thiosulfate solution and ethyl acetate were added to this reaction mixture and the layers were separated. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 11.1 mg of the title compound was obtained as a yellow solid.
［参考例１０］
　４－ブロモ－１－メチル－３－（７－（ペンタフルオロエチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000162
　参考例６で得られた４－ブロモ－３－（２－ブロモアセチル）－１－メチル－１Ｈ－ピラゾール－５－カルボン酸エチル　５．３６ｇと２－アミノ－４－（ペンタフルオロエチル）ピリジン　２．７９ｇを含むクロロベンゼン　３０．０ｍｌを加熱還流下で４時間攪拌した。この反応混合物を室温まで冷却した後に、飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４．９３ｇの褐色固体として得られた。 [Reference Example 10]
Synthesis of ethyl 4-bromo-1-methyl-3-(7-(pentafluoroethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000162
5.36 g of ethyl 4-bromo-3-(2-bromoacetyl)-1-methyl-1H-pyrazole-5-carboxylate obtained in Reference Example 6 and 2.79 g of 2-amino-4-(pentafluoroethyl)pyridine were stirred in 30.0 ml of chlorobenzene under heating and reflux for 4 hours. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added and the mixture was separated. The organic layer obtained was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 4.93 g of the title compound was obtained as a brown solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．４５　（１Ｈ，　ｓ），　８．２８　（１Ｈ，　ｄ，　Ｊ　＝　７．０　Ｈｚ），　７．９９　（１Ｈ，　ｓ），　６．９８　（１Ｈ，　ｄ，　Ｊ　＝　７．０　Ｈｚ），　４．４６　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．３０　（３Ｈ，　ｓ），　１．４７　（３Ｈ，　ｔ，　Ｊ　＝　７．０　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 8.45 (1H, s), 8.28 (1H, d, J = 7.0 Hz), 7.99 (1H, s), 6.98 (1H, d, J = 7.0 Hz), 4.46 (2H, q, J = 7.1 Hz), 4.30 (3H, s), 1.47 (3H, t, J = 7.0 Hz).
［参考例１１］
　４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロエチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000163
　４－ブロモ－１－メチル－３－（７－（ペンタフルオロエチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチル　２．００ｇ、エタンチオール　１．５８ｍｌ、トリス(ジベンジリデンアセトン)ジパラジウム　７８４ｍｇ、４，５－ビス（ジフェニルホスフィノ）－９，９－ジメチルキサンテン　９９１ｍｇとジイソプロピルエチルアミン　３．６９ｍｌを含む１，４－ジオキサン　１５．０ｍｌを１２０℃にて４時間攪拌した。室温まで冷却した後に、この反応混合物に飽和塩化アンモニウムと酢酸エチルを加えた。得られた残渣をセライトにてろ過した後に、酢酸エチルでセライト残渣を洗浄した。有機層と水層を分液後、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１．９４ｇの黄色固体として得られた。 [Reference Example 11]
Synthesis of ethyl 4-(ethylthio)-1-methyl-3-(7-(pentafluoroethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate
Figure JPOXMLDOC01-appb-C000163
2.00 g of ethyl 4-bromo-1-methyl-3-(7-(pentafluoroethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate, 1.58 ml of ethanethiol, 784 mg of tris(dibenzylideneacetone)dipalladium, 991 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and 15.0 ml of 1,4-dioxane containing 3.69 ml of diisopropylethylamine were stirred at 120° C. for 4 hours. After cooling to room temperature, saturated ammonium chloride and ethyl acetate were added to the reaction mixture. The resulting residue was filtered through Celite, and the Celite residue was washed with ethyl acetate. After separation of the organic layer and the aqueous layer, the resulting organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 1.94 g of the title compound was obtained as a yellow solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．７２　（１Ｈ，　ｓ），　８．２８　（１Ｈ，　ｄｄ，　Ｊ　＝　７．２，　１．１　Ｈｚ），　７．９７　（１Ｈ，　ｓ），　６．９７　（１Ｈ，　ｄｄ，　Ｊ　＝　７．２，　１．１　Ｈｚ），　４．４７　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　４．２６　（３Ｈ，　ｓ），　２．８３　（２Ｈ，　ｑ，　Ｊ　＝　７．３　Ｈｚ），　１．４７　（３Ｈ，　ｔ，　Ｊ　＝　７．０　Ｈｚ），　１．１７　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 8.72 (1H, s), 8.28 (1H, dd, J = 7.2, 1.1 Hz), 7.97 (1H, s), 6.97 (1H, dd, J = 7.2, 1.1 Hz), 4.47 (2H, q, J = 7.1 Hz), 4.26 (3H, s), 2.83 (2H, q, J = 7.3 Hz), 1.47 (3H, t, J = 7.0 Hz), 1.17 (3H, t, J = 7.3 Hz).
［参考例１２］
　４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸の合成
Figure JPOXMLDOC01-appb-C000164
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸エチル　１．６３ｇと水酸化ナトリウム　２６０ｍｇを含むエタノール　１２．０ｍｌ、テトラヒドロフラン　６．００ｍｌ、および水　１２．０ｍｌの混合溶液を室温下で３時間攪拌した。この反応混合物に、水と酢酸エチルを加えて分液した。得られた水層を１Ｍ塩酸水にて酸性にした後に、酢酸エチルを加えて抽出した。有機層と水層を分液した後に、得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去し、表題の化合物が１．５０ｇの白色固体として得られた。 [Reference Example 12]
Synthesis of 4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylic acid
Figure JPOXMLDOC01-appb-C000164
A mixed solution of 1.63 g of ethyl 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylate and 260 mg of sodium hydroxide in 12.0 ml of ethanol, 6.00 ml of tetrahydrofuran, and 12.0 ml of water was stirred at room temperature for 3 hours. Water and ethyl acetate were added to this reaction mixture for separation. The resulting aqueous layer was acidified with 1M aqueous hydrochloric acid, and then extracted with ethyl acetate. The organic layer and the aqueous layer were separated, and the resulting organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.50 g of the title compound as a white solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．４８　（１Ｈ，　ｓ），　８．３４　（１Ｈ，　ｄ，　Ｊ　＝　７．３　Ｈｚ），　８．１２　（１Ｈ，　ｓ），　７．０６　（１Ｈ，　ｄ，　Ｊ　＝　７．３　Ｈｚ），　４．３６　（３Ｈ，　ｓ），　２．９４　（２Ｈ，　ｑ，　Ｊ　＝　７．３　Ｈｚ），　１．２４　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 8.48 (1H, s), 8.34 (1H, d, J = 7.3 Hz), 8.12 (1H, s), 7.06 (1H, d, J = 7.3 Hz), 4.36 (3H, s), 2.94 (2H, q, J = 7.3 Hz), 1.24 (3H, t, J = 7.3 Hz).
［合成例５］
　ｔ－ブチル（４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）カルバメートの合成（化合物番号：４０）
Figure JPOXMLDOC01-appb-C000165
　４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボン酸　１．５０ｇ、トリエチルアミン　１．００ｍｌとジフェニルリン酸アジド　１．５４ｍｌを含むｔ－ブチルアルコール　３０．０ｍｌの溶液を８０℃に昇温して、さらに３時間攪拌した。この反応混合物を室温まで冷却した後に、水と酢酸エチルを加えて抽出した。有機層と水層を分液した後に、得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１．０９ｇの白色固体として得られた。 [Synthesis Example 5]
Synthesis of t-butyl (4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (Compound No. 40)
Figure JPOXMLDOC01-appb-C000165
A solution of 30.0 ml of t-butyl alcohol containing 1.50 g of 4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazole-5-carboxylic acid, 1.00 ml of triethylamine, and 1.54 ml of diphenylphosphoryl azide was heated to 80° C. and further stirred for 3 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added for extraction. After separating the organic layer from the aqueous layer, the obtained organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 1.09 g of the title compound was obtained as a white solid.
［合成例６］
　４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミンの合成（化合物番号：Ｉ－４）
Figure JPOXMLDOC01-appb-C000166
　ｔ－ブチル（４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）カルバメート　１．０９ｇ、トリフルオロ酢酸　１０．０ｍｌを含むジクロロメタン溶液　１０．０ｍｌを室温で１時間攪拌した。この反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去し、表題の化合物が７９２ｍｇの白色固体として得られた。 [Synthesis Example 6]
Synthesis of 4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-amine (Compound Number: I-4)
Figure JPOXMLDOC01-appb-C000166
A dichloromethane solution (10.0 ml) containing 1.09 g of t-butyl (4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)carbamate and 10.0 ml of trifluoroacetic acid was stirred at room temperature for 1 hour. A saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added to this reaction mixture, and the layers were separated. The obtained organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (792 mg) as a white solid.
［合成例７］
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－２，２，２－トリフルオロアセトアミドの合成
Figure JPOXMLDOC01-appb-C000167
　４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミン　６５．２ｍｇ、無水トリフルオロ酢酸　６６．６μｌ、トリエチルアミン９２．６μｌを含むジクロロメタン２．００ｍｌを室温で２．５時間攪拌した。この反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が７３．１ｍｇの黄色油状物として得られた。 [Synthesis Example 7]
Synthesis of N-(4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)-2,2,2-trifluoroacetamide
Figure JPOXMLDOC01-appb-C000167
2.00 ml of dichloromethane containing 65.2 mg of 4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-amine, 66.6 μl of anhydrous trifluoroacetic acid, and 92.6 μl of triethylamine was stirred at room temperature for 2.5 hours. A saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added to this reaction mixture, and the layers were separated. The resulting organic layer was washed with 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. 73.1 mg of the title compound was obtained as a yellow oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．５０　（１Ｈ，　ｓ），　８．２８－８．２７　（２Ｈ，　ｍ），　７．９８　（１Ｈ，　ｓ），　６．９９－６．９８　（１Ｈ，　ｍ），　３．９０　（３Ｈ，　ｓ），　２．６４　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　１．１２　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 8.50 (1H, s), 8.28-8.27 (2H, m), 7.98 (1H, s), 6.99-6.98 (1H, m), 3.90 (3H, s), 2.64 (2H, q, J = 7.2 Hz), 1.12 (3H, t, J = 7.2 Hz).
［合成例８］
　Ｎ－（４－（エチルスルホニル）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－２，２，２－トリフルオロアセトアミドの合成（化合物番号：４１）
Figure JPOXMLDOC01-appb-C000168
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－２，２，２－トリフルオロアセトアミド　７３．１ｍｇ、３－クロロ過安息香酸（ｃａ．７０％純度）　１４１．０ｍｇを含むジクロロメタン溶液　１．５ｍｌを室温で１．５時間攪拌した。この反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を、飽和炭酸水素ナトリウム水溶液にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１５．１ｍｇの白色固体として得られた。 [Synthesis Example 8]
Synthesis of N-(4-(ethylsulfonyl)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)-2,2,2-trifluoroacetamide (Compound No. 41)
Figure JPOXMLDOC01-appb-C000168
A dichloromethane solution (1.5 ml) containing 73.1 mg of N-(4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-yl)-2,2,2-trifluoroacetamide and 141.0 mg of 3-chloroperbenzoic acid (ca. 70% purity) was stirred at room temperature for 1.5 hours. Aqueous sodium thiosulfate solution and ethyl acetate were added to this reaction mixture for liquid separation. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 15.1 mg of the title compound was obtained as a white solid.
［合成例９］
　Ｎ－（４－（エチルスルホニル）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミンの合成（化合物番号：Ｉ－５）
Figure JPOXMLDOC01-appb-C000169
　４－（エチルチオ）－１－メチル－３－（７－（ペンタフルオロメチル）イミダゾ［１，２－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミン　８３．２ｍｇ、３－クロロ過安息香酸（ｃａ．７０％純度）　１２７．０ｍｇを含むジクロロメタン溶液　３．００ｍｌを室温で３０分間攪拌した。この反応混合物にチオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を、飽和炭酸水素ナトリウム水溶液にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４４．０ｍｇの白色固体として得られた。 [Synthesis Example 9]
Synthesis of N-(4-(ethylsulfonyl)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-amine (Compound No.: I-5)
Figure JPOXMLDOC01-appb-C000169
3.00 ml of a dichloromethane solution containing 83.2 mg of 4-(ethylthio)-1-methyl-3-(7-(pentafluoromethyl)imidazo[1,2-a]pyridin-2-yl)-1H-pyrazol-5-amine and 127.0 mg of 3-chloroperbenzoic acid (ca. 70% purity) was stirred at room temperature for 30 minutes. Aqueous sodium thiosulfate solution and ethyl acetate were added to this reaction mixture for separation. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography. 44.0 mg of the title compound was obtained as a white solid.
［参考例１３］
　５－アミノ－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル
Figure JPOXMLDOC01-appb-C000170
　シュウ酸ジエチル　１５．０ｇを含むアセトニトリル溶液　６０．０ｍｌに対して、０℃下、ｔ－ブトキシカリウム　１１．６ｇを加えた。この反応混合物を室温まで昇温した後に、３０分間攪拌した。得られた反応混合物をろ過した後に、残渣をアセトニトリルにて洗浄し、１－シアノ－３－エトキシ－３－オキソプロ－１－ペン－２－ノエート　１０．６ｇの白色固体として得た。この固体にメチルヒドラジン　３．７２ｍｌ、トリフルオロ酢酸　１３．６ｍｌ、エタノール　１００ｍｌを加えて８０℃で２．５時間攪拌した。この反応混合物を室温まで冷却した後に、飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が６．９８ｇの褐色油状物として得られた。 [Reference Example 13]
5-amino-1-methyl-1H-pyrazole-3-carboxylate ethyl
Figure JPOXMLDOC01-appb-C000170
To 60.0 ml of an acetonitrile solution containing 15.0 g of diethyl oxalate, 11.6 g of potassium t-butoxide was added at 0° C. The reaction mixture was warmed to room temperature and then stirred for 30 minutes. The resulting reaction mixture was filtered, and the residue was washed with acetonitrile to obtain 10.6 g of 1-cyano-3-ethoxy-3-oxoprop-1-pen-2-noate as a white solid. To this solid, 3.72 ml of methylhydrazine, 13.6 ml of trifluoroacetic acid, and 100 ml of ethanol were added and stirred at 80° C. for 2.5 hours. The reaction mixture was cooled to room temperature, and then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to separate the layers. The resulting organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound was obtained as 6.98 g of a brown oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．０９　（１Ｈ，　ｓ），　４．３７　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　３．７５　（３Ｈ，　ｓ），　１．３８　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 6.09 (1H, s), 4.37 (2H, q, J = 7.2 Hz), 3.75 (3H, s), 1.38 (3H, t, J = 7.2 Hz).
［参考例１４］
　５－（ビス（ｔ－ブトキシカルボニル）アミノ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル
Figure JPOXMLDOC01-appb-C000171
　５－アミノ－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル　６．９８ｇ、二炭酸ジ－ｔ－ブチル　２３．４ｍｌ、ジメチルアミノピリジン　１．０１ｇを含むテトラヒドロフラン溶液　７０．０ｍｌを室温下で１５分間攪拌した。この反応混合物に、酢酸エチルと塩化アンモニウム水溶液を加えて分液した。得られた有機層を食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、表題の化合物が２１．０ｇの褐色油状物として得られた。これ以上精製することなく、次の反応に使用した。 [Reference Example 14]
5-(bis(t-butoxycarbonyl)amino)-1-methyl-1H-pyrazole-3-carboxylate ethyl
Figure JPOXMLDOC01-appb-C000171
A tetrahydrofuran solution (70.0 ml) containing 6.98 g of ethyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate, 23.4 ml of di-t-butyl dicarbonate, and 1.01 g of dimethylaminopyridine was stirred at room temperature for 15 minutes. Ethyl acetate and an aqueous solution of ammonium chloride were added to the reaction mixture, and the layers were separated. The resulting organic layer was washed with brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the title compound was obtained as a brown oil (21.0 g). The product was used in the next reaction without further purification.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．６６　（１Ｈ，　ｓ），　４．４３－４．３８　（２Ｈ，　ｍ），　３．７５　（３Ｈ，　ｓ），　１．４２－１．４０　（２１Ｈ，　ｍ）． 1H -NMR ( CDCl3 ) δ: 6.66 (1H, s), 4.43-4.38 (2H, m), 3.75 (3H, s), 1.42-1.40 (21H, m).
［参考例１５］
　５－（（ｔ－ブトキシカルボニル）アミノ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル
Figure JPOXMLDOC01-appb-C000172
　５－（ビス（ｔ－ブトキシカルボニル）アミノ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル　２１．０ｇ、臭化リチウム　５．３８ｇを含むアセトニトリル溶液　１５０ｍｌを加熱還流下で４０分間攪拌した。この反応混合物を室温まで冷却した後に、飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。攪拌した。この反応混合物に、酢酸エチルと塩化アンモニウム水溶液を加えて分液した。得られた有機層を食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が７．３４ｇの褐色油状物として得られた。 [Reference Example 15]
5-((t-butoxycarbonyl)amino)-1-methyl-1H-pyrazole-3-carboxylate ethyl
Figure JPOXMLDOC01-appb-C000172
150 ml of an acetonitrile solution containing 21.0 g of ethyl 5-(bis(t-butoxycarbonyl)amino)-1-methyl-1H-pyrazole-3-carboxylate and 5.38 g of lithium bromide was stirred for 40 minutes under heating and reflux. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added and the mixture was separated. The mixture was stirred. Ethyl acetate and an aqueous solution of ammonium chloride were added to the reaction mixture and the mixture was separated. The organic layer obtained was washed with saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. 7.34 g of the title compound was obtained as a brown oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．６９　（１Ｈ，　ｓ），　６．１８　（１Ｈ，　ｂｒ　ｓ），　４．３９　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　３．８３　（３Ｈ，　ｓ），　１．５１　（９Ｈ，　ｓ），　１．３８　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 6.69 (1H, s), 6.18 (1H, br s), 4.39 (2H, q, J = 7.2 Hz), 3.83 (3H, s), 1.51 (9H, s), 1.38 (3H, t, J = 7.2 Hz).
［参考例１６］
　５－（（ｔ－ブトキシカルボニル）アミノ）－４－ヨード－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000173
　５－（（ｔ－ブトキシカルボニル）アミノ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル　７．３４ｇ、Ｎ－ヨードスクシンイミド　９．２０ｇを含むジメチルホルムアミド　３７．０ｍｌを５０℃で１．５時間攪拌した。室温まで冷却した後に、反応混合物に、１％チオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が９．８４ｇの褐色油状物として得られた。 [Reference Example 16]
Synthesis of ethyl 5-((t-butoxycarbonyl)amino)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate
Figure JPOXMLDOC01-appb-C000173
7.34 g of ethyl 5-((t-butoxycarbonyl)amino)-1-methyl-1H-pyrazole-3-carboxylate and 9.20 g of N-iodosuccinimide in 37.0 ml of dimethylformamide were stirred at 50° C. for 1.5 hours. After cooling to room temperature, a 1% aqueous sodium thiosulfate solution and ethyl acetate were added to the reaction mixture for liquid separation. The resulting organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 9.84 g of the title compound was obtained as a brown oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　５．９７　（１Ｈ，　ｂｒ　ｓ），　４．４３　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　３．９２　（３Ｈ，　ｓ），　１．５０　（９Ｈ，　ｓ），　１．４２　（３Ｈ，　ｔ，　Ｊ　＝　７．１　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 5.97 (1H, br s), 4.43 (2H, q, J = 7.1 Hz), 3.92 (3H, s), 1.50 (9H, s), 1.42 (3H, t, J = 7.1 Hz).
［参考例１７］
　５－（（ｔ－ブトキシカルボニル）アミノ）－４－（エチルチオ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000174
　５－（（ｔ－ブトキシカルボニル）アミノ）－４－ヨード－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル　９．８４ｇ、エタンチオール　５．５２ｍｌ、トリス(ジベンジリデンアセトン)ジパラジウム　１．１４ｇ、４，５－ビス（ジフェニルホスフィノ）－９，９－ジメチルキサンテン　１．４４ｇとジイソプロピルエチルアミン　１２．９ｍｌを含む１，４－ジオキサン　９８．０ｍｌを１１０℃にて１．５時間攪拌した。室温まで冷却した後に、反応混合物に飽和塩化アンモニウムと酢酸エチルを加えた。得られた残渣をセライトにてろ過した後に、酢酸エチルでセライト残渣を洗浄した。有機層と水層を分液後、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が７．３８ｇの橙色油状物として得られた。 [Reference Example 17]
Synthesis of ethyl 5-((t-butoxycarbonyl)amino)-4-(ethylthio)-1-methyl-1H-pyrazole-3-carboxylate
Figure JPOXMLDOC01-appb-C000174
98.0 ml of 1,4-dioxane containing 9.84 g of ethyl 5-((t-butoxycarbonyl)amino)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate, 5.52 ml of ethanethiol, 1.14 g of tris(dibenzylideneacetone)dipalladium, 1.44 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and 12.9 ml of diisopropylethylamine was stirred at 110° C. for 1.5 hours. After cooling to room temperature, saturated ammonium chloride and ethyl acetate were added to the reaction mixture. The resulting residue was filtered through Celite, and the Celite residue was washed with ethyl acetate. The organic layer and the aqueous layer were separated, and the resulting organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 7.38 g of the title compound was obtained as an orange oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．３０　（１Ｈ，　ｂｒ　ｓ），　４．４３　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　３．８８　（３Ｈ，　ｓ），　２．７７　（２Ｈ，　ｑ，　Ｊ　＝　７．３　Ｈｚ），　１．５０　（９Ｈ，　ｓ），　１．４２　（３Ｈ，　ｔ，　Ｊ　＝　７．１　Ｈｚ），　１．１４　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 6.30 (1H, br s), 4.43 (2H, q, J = 7.1 Hz), 3.88 (3H, s), 2.77 (2H, q, J = 7.3 Hz), 1.50 (9H, s), 1.42 (3H, t, J = 7.1 Hz), 1.14 (3H, t, J = 7.3 Hz).
［参考例１８］
　５－（（ｔ－ブトキシカルボニル）アミノ）－４－（エチルチオ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸の合成
Figure JPOXMLDOC01-appb-C000175
　５－（（ｔ－ブトキシカルボニル）アミノ）－４－（エチルチオ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸エチル　７．３８ｇと水酸化ナトリウム　１．７９ｇを含むエタノール　３０．０ｍｌ、テトラヒドロフラン　３０．０ｍｌと水　３０．０ｇの混合溶媒を５０℃で３０分間攪拌した。反応混合物に１Ｎ塩酸水とジクロロメタンを加えて、有機層を分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去し、表題の化合物が６．６７ｇの褐色固体として得られた。 [Reference Example 18]
Synthesis of 5-((t-butoxycarbonyl)amino)-4-(ethylthio)-1-methyl-1H-pyrazole-3-carboxylic acid
Figure JPOXMLDOC01-appb-C000175
A mixed solvent of 30.0 ml of ethanol, 30.0 ml of tetrahydrofuran, and 30.0 g of water containing 7.38 g of ethyl 5-((t-butoxycarbonyl)amino)-4-(ethylthio)-1-methyl-1H-pyrazole-3-carboxylate and 1.79 g of sodium hydroxide was stirred at 50° C. for 30 minutes. 1N aqueous hydrochloric acid and dichloromethane were added to the reaction mixture, and the organic layer was separated. The obtained organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 6.67 g of the title compound as a brown solid.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　６．４０　（１Ｈ，　ｓ），　３．８９　（３Ｈ，　ｓ），　２．７７　（２Ｈ，　ｑ，　Ｊ　＝　７．３　Ｈｚ），　１．５１　（９Ｈ，　ｓ），　１．１６　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1H -NMR ( CDCl3 ) δ: 6.40 (1H, s), 3.89 (3H, s), 2.77 (2H, q, J = 7.3 Hz), 1.51 (9H, s), 1.16 (3H, t, J = 7.3 Hz).
［参考例１９］
　１，２－ジアミノ－４－（トリフルオロメチル）ピリジン－１－イウム　２，４，６－トリメチルベンゼンスルホネートの合成
Figure JPOXMLDOC01-appb-C000176
　Ｏ－（メシチルスルホニル）ヒドロキシルアミン　１．３７ｇを含むジクロロメタン溶液　１０．０ｍｌに、４－（トリフルオロメチル）ピリジン－２－アミン　１．０３ｇを含むジクロロメタン溶液　１０．０ｍｌを０℃下にて滴下して加えた。反応混合物を室温まで昇温した後に、２．５時間攪拌した。得られた反応混合物をろ過した後に、残渣をジクロロメタンにて洗浄した。表題の化合物が２．２９ｇの白色固体として得られた。 [Reference Example 19]
Synthesis of 1,2-diamino-4-(trifluoromethyl)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate
Figure JPOXMLDOC01-appb-C000176
To 10.0 ml of a dichloromethane solution containing 1.37 g of O-(mesitylsulfonyl)hydroxylamine, 10.0 ml of a dichloromethane solution containing 1.03 g of 4-(trifluoromethyl)pyridin-2-amine was added dropwise at 0° C. The reaction mixture was warmed to room temperature and then stirred for 2.5 hours. The resulting reaction mixture was filtered, and the residue was washed with dichloromethane. 2.29 g of the title compound was obtained as a white solid.
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　８．８２　（２Ｈ，　ｂｒ　ｓ），　８．２８　（１Ｈ，　ｄ，　Ｊ　＝　７．０　Ｈｚ），　７．４１　（１Ｈ，　ｓ），　７．１５　（１Ｈ，　ｄｄ，　Ｊ　＝　７．２，　２．３　Ｈｚ），　６．９９　（２Ｈ，　ｓ），　６．７５　（２Ｈ，　ｓ），　２．４９　（６Ｈ，　ｓ），　２．１７　（３Ｈ，　ｓ）． 1H -NMR (DMSO- D6 ) δ: 8.82 (2H, br s), 8.28 (1H, d, J = 7.0 Hz), 7.41 (1H, s), 7.15 (1H, dd, J = 7.2, 2.3 Hz), 6.99 (2H, s), 6.75 (2H, s), 2.49 (6H, s), 2.17 (3H, s).
［合成例１０］
　ｔ－ブチル　（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）カルバメートの合成（化合物番号：１）
Figure JPOXMLDOC01-appb-C000177
　５－（（ｔ－ブトキシカルボニル）アミノ）－４－（エチルチオ）－１－メチル－１Ｈ－ピラゾール－３－カルボン酸　６．４３ｇと１－［ビス（ジメチルアミノ）メチレン］－１Ｈ－１，２，３－トリアゾロ［４，５－ｂ］ピリジニウム３－オキシドヘキサフルオロホスファート　７９７ｍｇ、トリエチルアミン　２．７０ｇを含むジメチルホルムアミド　６５．０ｍｌを室温下で１時間攪拌した。減圧下で溶媒を留去し、得られた溶液に、ピリジン　６５．０ｍｌ、１，２－ジアミノ－４－（トリフルオロメチル）ピリジン－１－イウム　２，４，６－トリメチルベンゼンスルホネート　６．００ｇを加えた。反応混合物を８０℃まで昇温した後に、さらに６時間攪拌した。室温まで冷却した後に、１Ｎ塩酸水と酢酸エチルを加えて分液した。得られた有機層を飽和炭酸水素ナトリウム水溶液と飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒を留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が、２．８８ｇの白色固体として得られた。 [Synthesis Example 10]
Synthesis of t-butyl (4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (Compound No. 1)
Figure JPOXMLDOC01-appb-C000177
6.43 g of 5-((t-butoxycarbonyl)amino)-4-(ethylthio)-1-methyl-1H-pyrazole-3-carboxylic acid, 797 mg of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and 65.0 ml of dimethylformamide containing 2.70 g of triethylamine were stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and 65.0 ml of pyridine and 6.00 g of 1,2-diamino-4-(trifluoromethyl)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate were added to the resulting solution. The reaction mixture was heated to 80° C. and then stirred for another 6 hours. After cooling to room temperature, 1N aqueous hydrochloric acid and ethyl acetate were added and the mixture was separated. The resulting organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, and dried over sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (2.88 g) as a white solid.
［合成例１１］
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミンの合成（化合物番号：Ｉ－１）
Figure JPOXMLDOC01-appb-C000178
　ｔ－ブチル　（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）カルバメート　１．３０ｇ、トリフルオロ酢酸　１３．０ｍｌを含むジクロロメタン溶液１２．６ｍｌを室温下で１時間攪拌した。この反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去し、得られた残渣をジイソプロピルエーテルにて洗浄した。表題の化合物が９３１ｍｇの白色固体として得られた。 [Synthesis Example 11]
Synthesis of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-amine (Compound Number: I-1)
Figure JPOXMLDOC01-appb-C000178
A dichloromethane solution (12.6 ml) containing 1.30 g of t-butyl (4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)carbamate and 13.0 ml of trifluoroacetic acid was stirred at room temperature for 1 hour. A saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added to this reaction mixture, and the layers were separated. The organic layer obtained was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was washed with diisopropyl ether. 931 mg of the title compound was obtained as a white solid.
［参考例２０］
　（Ｅ）－２－（ヒドロキシイミノ）酢酸エチルの合成
Figure JPOXMLDOC01-appb-C000179
　グリオキシル酸エチル（ポリマー型、４７％トルエン溶液）　４．２３ｇ、ヒドロキシルアミン塩酸　１．７７ｇ、ピリジン　２．０６ｍｌを含むエタノール溶液　２０ｍｌを６０℃にて３時間撹拌した。この反応混合物を室温に冷却した後、減圧下で溶媒留去した。得られた残渣に水と酢酸エチルを加えて分液した。得られた有機相を食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が１．４９ｇの無色オイルとして得られた。 [Reference Example 20]
Synthesis of ethyl (E)-2-(hydroxyimino)acetate
Figure JPOXMLDOC01-appb-C000179
20 ml of an ethanol solution containing 4.23 g of ethyl glyoxylate (polymer type, 47% toluene solution), 1.77 g of hydroxylamine hydrochloride, and 2.06 ml of pyridine was stirred at 60° C. for 3 hours. After cooling the reaction mixture to room temperature, the solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the resulting residue and the mixture was separated. The resulting organic phase was washed with saline and dried over magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography. 1.49 g of the title compound was obtained as a colorless oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．９０　（１Ｈ，　ｓ），　７．５７　（１Ｈ，　ｓ），　４．３３　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　１．３６　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H-NMR (CDCl3) δ: 8.90 (1H, s), 7.57 (1H, s), 4.33 (2H, q, J = 7.2 Hz), 1.36 (3H, t, J = 7.2 Hz).
［参考例２１］
　５，５－ジメチル－４，５－ジヒドロイソキサゾール－３－カルボン酸エチルの合成
Figure JPOXMLDOC01-appb-C000180
　（Ｅ）－２－（ヒドロキシイミノ）酢酸エチル　１．４９ｇ、Ｎ－クロロスクシンイミド　１．６９ｇを含むジメチルホルムアミド溶液１５．０ｍｌを４０℃にて１時間撹拌した。この反応混合物を６０℃に昇温した後、１時間２０分撹拌した。この反応混合物を室温に冷却した後、水と酢酸エチルを加えて分液した。得られた有機相を水と食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣に、０℃下でイソブテン（１５％テトラヒドロフラン溶液）２８．６ｍｌ、トリエチルアミン１．７７ｍｌを加えた。この反応混合物を室温に昇温して１９時間撹拌した。この反応混合物に水と酢酸エチルを加えて分液した。得られた有機相を食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が１．４７ｇの無色オイルとして得られた。 [Reference Example 21]
Synthesis of ethyl 5,5-dimethyl-4,5-dihydroisoxazole-3-carboxylate
Figure JPOXMLDOC01-appb-C000180
15.0 ml of a dimethylformamide solution containing 1.49 g of ethyl (E)-2-(hydroxyimino)acetate and 1.69 g of N-chlorosuccinimide was stirred at 40° C. for 1 hour. The reaction mixture was heated to 60° C. and then stirred for 1 hour and 20 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to separate the mixture. The organic phase was washed with water and saline, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and 28.6 ml of isobutene (15% tetrahydrofuran solution) and 1.77 ml of triethylamine were added to the residue at 0° C. The reaction mixture was heated to room temperature and stirred for 19 hours. Water and ethyl acetate were added to the reaction mixture and separated the mixture. The organic phase was washed with saline, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound was obtained as 1.47 g of a colorless oil.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　４．３４　（２Ｈ，　ｑ，　Ｊ　＝　７．２　Ｈｚ），　２．９７　（２Ｈ，　ｓ），　１．４６　（６Ｈ，　ｓ），　１．３７　（３Ｈ，　ｔ，　Ｊ　＝　７．２　Ｈｚ）． 1H-NMR (CDCl3) δ: 4.34 (2H, q, J = 7.2 Hz), 2.97 (2H, s), 1.46 (6H, s), 1.37 (3H, t, J = 7.2 Hz).
［参考例２２］
　５，５－ジメチル－４，５－ジヒドロイソキサゾール－３－カルボン酸の合成
Figure JPOXMLDOC01-appb-C000181
　５，５－ジメチル－４，５－ジヒドロイソキサゾール－３－カルボン酸エチル　１．４７ｇ、水酸化リチウム１水和物　４３１ｍｇを含むメタノール　２２．０ｍｌ、水　７．３０ｍｌの混合溶液を室温で５時間３０分撹拌した。この反応混合物に１Ｎ塩酸水とジクロロメタンを加えて分液した。得られた有機相を硫酸マグネシウムで乾燥した。減圧下で溶媒留去することで表題の化合物が７９６ｍｇの白色固体として得られた。これ以上精製することなく、次の反応に使用した。 [Reference Example 22]
Synthesis of 5,5-dimethyl-4,5-dihydroisoxazole-3-carboxylic acid
Figure JPOXMLDOC01-appb-C000181
A mixed solution of 1.47 g of ethyl 5,5-dimethyl-4,5-dihydroisoxazole-3-carboxylate, 431 mg of lithium hydroxide monohydrate, 22.0 ml of methanol, and 7.30 ml of water was stirred at room temperature for 5 hours and 30 minutes. 1N aqueous hydrochloric acid and dichloromethane were added to this reaction mixture and the layers were separated. The obtained organic phase was dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a white solid (796 mg). This was used in the next reaction without further purification.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　２．９８　（２Ｈ，　ｓ），　１．４９　（６Ｈ，　ｓ）． 1H-NMR (CDCl3) δ: 2.98 (2H, s), 1.49 (6H, s).
［合成例１２］
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－５，５－ジメチル－４，５－ジヒドロイキサゾール－３－カルボキサミドの合成（化合物番号：２４９）
Figure JPOXMLDOC01-appb-C000182
　５，５－ジメチル－４，５－ジヒドロイキサゾール－３－カルボン酸　２０４ｍｇ、ジメチルホルムアミド１滴を含むジクロロメタン溶液２．００ｍｌに室温下にて塩化オキザリル　１２８μｌを加えて１時間４０分撹拌した。減圧下で溶媒留去して得られた残渣にテトラヒドロフラン　１．４０ｍｌを加えた。得られたテトラヒドロフラン溶液５３０μｌを、４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５，ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミン　６０．０ｍｇ、ピリジン　４２．４μｌを含むテトラヒドロフラン溶液６００μｌに室温下で加えて２０分撹拌した。この反応混合物に水と酢酸エチルを加えて分液した。得られた有機相を飽和炭酸水素ナトリウム水溶液と食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が７６．０ｍｇの白色固体として得られた。 [Synthesis Example 12]
Synthesis of N-(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-5,5-dimethyl-4,5-dihydroixazole-3-carboxamide (Compound Number: 249)
Figure JPOXMLDOC01-appb-C000182
128 μl of oxalyl chloride was added to 2.00 ml of a dichloromethane solution containing 204 mg of 5,5-dimethyl-4,5-dihydroixazole-3-carboxylic acid and one drop of dimethylformamide at room temperature, and the mixture was stirred for 1 hour and 40 minutes. The solvent was distilled off under reduced pressure, and 1.40 ml of tetrahydrofuran was added to the residue. 530 μl of the resulting tetrahydrofuran solution was added to 600 μl of a tetrahydrofuran solution containing 60.0 mg of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5,a]pyridin-2-yl)-1H-pyrazol-5-amine and 42.4 μl of pyridine at room temperature, and the mixture was stirred for 20 minutes. Water and ethyl acetate were added to this reaction mixture, and the mixture was separated. The resulting organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and saline, and dried over magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography. The title compound was obtained as 76.0 mg of a white solid.
［合成例１３］
　Ｎ－（４－（エチルスルホニル）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－５，５－ジメチル－４，５－ジヒドロイキサゾール－３－カルボキサミドの合成（化合物番号：２５０）
Figure JPOXMLDOC01-appb-C000183
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－５，５－ジメチル－４，５－ジヒドロイキサゾール－３－カルボキサミド　６５．２ｍｇを含むジクロロメタン溶液１．３０ｍｌに０℃下で３－クロロ過安息香酸（ｃａ．７０％）　７２．２ｍｇを加えて３０分撹拌した。この反応混合物に５％チオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機相を食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が６１．４ｍｇの白色固体として得られた。 [Synthesis Example 13]
Synthesis of N-(4-(ethylsulfonyl)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-5,5-dimethyl-4,5-dihydroixazole-3-carboxamide (Compound No. 250)
Figure JPOXMLDOC01-appb-C000183
To 1.30 ml of a dichloromethane solution containing 65.2 mg of N-(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-5,5-dimethyl-4,5-dihydroixazole-3-carboxamide, 72.2 mg of 3-chloroperbenzoic acid (ca. 70%) was added at 0° C. and stirred for 30 minutes. To this reaction mixture, a 5% aqueous solution of sodium thiosulfate and ethyl acetate were added and the mixture was separated. The resulting organic phase was washed with saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography. 61.4 mg of the title compound was obtained as a white solid.
［合成例１４］
Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－２，２，３，３，３－ペンタフルオロプロパンアミドの合成（化合物番号：１５）
Figure JPOXMLDOC01-appb-C000184
　４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミン　８６．９ｍｇ、トリエチルアミン　１０７μｌを含むジクロロメタン溶液１．００ｍｌに室温下で無水ペンタフルオロプロピオン酸　１４９μｌを加えて１時間撹拌した。この反応混合物に飽和炭酸水素ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を硫酸ナトリウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が４５．８ｍｇの白色固体として得られた。 [Synthesis Example 14]
Synthesis of N-(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-2,2,3,3,3-pentafluoropropanamide (Compound No. 15)
Figure JPOXMLDOC01-appb-C000184
To 1.00 ml of a dichloromethane solution containing 86.9 mg of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-amine and 107 μl of triethylamine, 149 μl of anhydrous pentafluoropropionic acid was added at room temperature and stirred for 1 hour. A saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added to this reaction mixture, and the mixture was separated. The resulting organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 45.8 mg of the title compound was obtained as a white solid.
［合成例１５］
　Ｎ－（４－（エチルスルホニル）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－２，２，３，３，３－ペンタフルオロプロパンアミドの合成（化合物番号：１７）
Figure JPOXMLDOC01-appb-C000185
　Ｎ－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－２，２，３，３，３－ペンタフルオロプロパンアミド　３１．９ｍｇを含むジクロロメタン溶液に０℃下で３－クロロ過安息香酸（ｃａ．７０％純度）　３８．７ｍｇを加えた。この反応混合物を室温に昇温して２時間２０分撹拌した。この反応混合物に５％チオ硫酸ナトリウム水溶液、飽和炭酸水素ナトリウム水溶液、酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が２１．６ｍｇの白色固体として得られた。 [Synthesis Example 15]
Synthesis of N-(4-(ethylsulfonyl)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-2,2,3,3,3-pentafluoropropanamide (Compound No. 17)
Figure JPOXMLDOC01-appb-C000185
To a dichloromethane solution containing 31.9 mg of N-(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-2,2,3,3,3-pentafluoropropanamide, 38.7 mg of 3-chloroperbenzoic acid (ca. 70% purity) was added at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 hours and 20 minutes. A 5% aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium hydrogen carbonate, and ethyl acetate were added to the reaction mixture, and the mixture was separated. The organic layer obtained was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography. 21.6 mg of the title compound was obtained as a white solid.
［合成例１６］
　Ｎ１－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－Ｎ２，Ｎ２－ジメチルオキサラミドの合成（化合物番号：２４１）
Figure JPOXMLDOC01-appb-C000186
　Ｎ，Ｎ－ジメチルオキサミン酸　１０３ｍｇ、ジメチルホルムアミド　１滴を含むジクロロメタン溶液１．００ｍｌに、室温下で塩化オキザリル６０．１μｌを加えて２時間撹拌した。この反応溶液を、４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－アミン　６０．０ｍｇ、ピリジン　１４１μｌを含むテトラヒドロフラン溶液１．００ｍｌに０℃下で加えて１５分撹拌した。この反応混合物に水と酢酸エチルを加えて分液した。得られた有機層を飽和炭酸水素ナトリウム水溶液と食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が６３．１ｍｇの白色固体として得られた。 [Synthesis Example 16]
Synthesis of N 1 -(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-N 2 ,N 2 -dimethyloxalamide (Compound No. 241)
Figure JPOXMLDOC01-appb-C000186
To 1.00 ml of a dichloromethane solution containing 103 mg of N,N-dimethyloxamic acid and one drop of dimethylformamide, 60.1 μl of oxalyl chloride was added at room temperature and stirred for 2 hours. This reaction solution was added to 1.00 ml of a tetrahydrofuran solution containing 60.0 mg of 4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-amine and 141 μl of pyridine at 0° C., and stirred for 15 minutes. Water and ethyl acetate were added to this reaction mixture, and the mixture was separated. The organic layer obtained was washed with a saturated aqueous solution of sodium bicarbonate and saline, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. 63.1 mg of the title compound was obtained as a white solid.
［合成例１７］
　Ｎ１－（４－（エチルスルホニル）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－Ｎ２，Ｎ２－ジメチルオキサラミドの合成（化合物番号：２４３）
Figure JPOXMLDOC01-appb-C000187
　Ｎ１－（４－（エチルチオ）－１－メチル－３－（７－（トリフルオロメチル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジン－２－イル）－１Ｈ－ピラゾール－５－イル）－Ｎ２，Ｎ２－ジメチルオキサラミド　５１．９ｍｇを含むジクロロメタン溶液１．００ｍｌに０℃下で３－クロロ過安息香酸（ｃａ．７０％純度）　６０．９ｍｇを加えて３０分撹拌した。この反応混合物に５％チオ硫酸ナトリウム水溶液と酢酸エチルを加えて分液した。得られた有機層を食塩水で洗浄し、硫酸マグネシウムで乾燥した。減圧下で溶媒留去して得られた残渣をシリカゲルカラムクロマトグラフィーで精製した。表題の化合物が４１．９ｍｇの白色固体として得られた。 [Synthesis Example 17]
Synthesis of N 1 -(4-(ethylsulfonyl)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-N 2 ,N 2 -dimethyloxalamide (Compound No. 243)
Figure JPOXMLDOC01-appb-C000187
To 1.00 ml of a dichloromethane solution containing 51.9 mg of N 1 -(4-(ethylthio)-1-methyl-3-(7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-1H-pyrazol-5-yl)-N 2 ,N 2 -dimethyloxalamide, 60.9 mg of 3-chloroperbenzoic acid (ca. 70% purity) was added at 0° C. and stirred for 30 minutes. To this reaction mixture, a 5% aqueous sodium thiosulfate solution and ethyl acetate were added for separation. The resulting organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography. 41.9 mg of the title compound was obtained as a white solid.
　表８に、前記した実施例に準じて合成した本発明化合物を示すが、本発明はこれらに限定されるものではない。 Table 8 shows compounds of the present invention synthesized according to the above examples, but the present invention is not limited to these.
　表８中、Ｐｈはフェニル基を表し、２－Ｐｙは、ピリジン－２－イル基を表し、３－Ｐｙは、ピリジン－３－イル基を表し、４－Ｐｙは、ピリジン－４－イル基を表し、１－Ｐｙｒａは、１Ｈ－ピラゾール－１－イル基を表し、１－Ｔｒｉａは、１Ｈ－トリアゾール－１－イル基を表す。 In Table 8, Ph represents a phenyl group, 2-Py represents a pyridin-2-yl group, 3-Py represents a pyridin-3-yl group, 4-Py represents a pyridin-4-yl group, 1-Pyra represents a 1H-pyrazol-1-yl group, and 1-Tria represents a 1H-triazol-1-yl group.
　表８中、構造Ａは以下を示す。
Figure JPOXMLDOC01-appb-C000188
 In Table 8, Structure A shows the following:
Figure JPOXMLDOC01-appb-C000188
　表８中、構造Ｂは以下を示す。
Figure JPOXMLDOC01-appb-C000189
 In Table 8, Structure B shows the following:
Figure JPOXMLDOC01-appb-C000189
Figure JPOXMLDOC01-appb-T000190
Figure JPOXMLDOC01-appb-T000190
Figure JPOXMLDOC01-appb-T000191
Figure JPOXMLDOC01-appb-T000191
Figure JPOXMLDOC01-appb-T000192
Figure JPOXMLDOC01-appb-T000192
Figure JPOXMLDOC01-appb-T000193
Figure JPOXMLDOC01-appb-T000193
Figure JPOXMLDOC01-appb-T000194
Figure JPOXMLDOC01-appb-T000194
Figure JPOXMLDOC01-appb-T000195
Figure JPOXMLDOC01-appb-T000195
　次に、表８に記載の化合物に関して、表９にそれらの１Ｈ－ＮＭＲデータを示す。 Next, for the compounds described in Table 8, 1 H-NMR data thereof is shown in Table 9.
Figure JPOXMLDOC01-appb-T000196
Figure JPOXMLDOC01-appb-T000196
Figure JPOXMLDOC01-appb-T000197
Figure JPOXMLDOC01-appb-T000197
Figure JPOXMLDOC01-appb-T000198
Figure JPOXMLDOC01-appb-T000198
Figure JPOXMLDOC01-appb-T000199
Figure JPOXMLDOC01-appb-T000199
Figure JPOXMLDOC01-appb-T000200
Figure JPOXMLDOC01-appb-T000200
Figure JPOXMLDOC01-appb-T000201
Figure JPOXMLDOC01-appb-T000201
Figure JPOXMLDOC01-appb-T000202
Figure JPOXMLDOC01-appb-T000202
Figure JPOXMLDOC01-appb-T000203
Figure JPOXMLDOC01-appb-T000203
Figure JPOXMLDOC01-appb-T000204
Figure JPOXMLDOC01-appb-T000204
Figure JPOXMLDOC01-appb-T000205
Figure JPOXMLDOC01-appb-T000205
Figure JPOXMLDOC01-appb-T000206
Figure JPOXMLDOC01-appb-T000206
Figure JPOXMLDOC01-appb-T000207
Figure JPOXMLDOC01-appb-T000207
Figure JPOXMLDOC01-appb-T000208
Figure JPOXMLDOC01-appb-T000208
Figure JPOXMLDOC01-appb-T000209
Figure JPOXMLDOC01-appb-T000209
　表１０に、前記した実施例に準じて合成した本発明化合物の合成中間体を示すが、これらに限定されるものではない。 Table 10 shows synthetic intermediates of the compounds of the present invention synthesized in accordance with the above-mentioned examples, but is not limited to these.
　表１０中、構造Ｃは以下を示す。
Figure JPOXMLDOC01-appb-C000210
 In Table 10, Structure C shows the following:
Figure JPOXMLDOC01-appb-C000210
　表１０中、構造Ｄは以下を示す。
Figure JPOXMLDOC01-appb-C000211
 In Table 10, Structure D represents the following:
Figure JPOXMLDOC01-appb-C000211
Figure JPOXMLDOC01-appb-T000212
Figure JPOXMLDOC01-appb-T000212
　次に、表１０に記載の合成中間体化合物に関して、表１１にそれらの１Ｈ－ＮＭＲデータを示す。 Next, with regard to the synthetic intermediate compounds shown in Table 10, the 1 H-NMR data thereof are shown in Table 11.
Figure JPOXMLDOC01-appb-T000213
Figure JPOXMLDOC01-appb-T000213
　次に、本発明化合物を有効成分として含有する製剤例を示すが、本発明はこれに限定されるものではない。なお、製剤例中、「部」とあるのは「重量部」を示す。 Next, examples of formulations containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited to these. In the formulation examples, "parts" refers to "parts by weight."
[製剤例１]
　式（１－１）、または式（１－２）で表される本発明化合物１０部、ポリオキシエチレンアリールフェニルエーテルサルフェートアンモニウム塩３０部、ＮＢＰ（１－ブチル－２－ピロリドン）１６０部、以上を均一に混合して乳剤を得た。 [Formulation Example 1]
10 parts of the compound of the present invention represented by formula (1-1) or (1-2), 30 parts of polyoxyethylene arylphenyl ether sulfate ammonium salt, and 160 parts of NBP (1-butyl-2-pyrrolidone) were mixed uniformly to obtain an emulsion.
[製剤例２]
　式（１－１）、または式（１－２）で表される本発明化合物１０部、ラウリル硫酸ナトリウム２部、ジアルキルスルフォサクシネート２部、β‐ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩１部、珪藻土８５部以上を均一に撹拌混合して水和剤を得た。 [Formulation Example 2]
A wettable powder was obtained by uniformly mixing 10 parts of the compound of the present invention represented by formula (1-1) or formula (1-2), 2 parts of sodium lauryl sulfate, 2 parts of dialkylsulfosuccinate, 1 part of β-naphthalenesulfonic acid formalin condensate sodium salt, and 85 parts or more of diatomaceous earth with stirring.
[製剤例３]
　式（１－１）、または式（１－２）で表される本発明化合物０．３部、ホワイトカーボン０．３部を均一に混合し、クレー９９．２部、ドリレスＡ（三共アグロ製）０．２部を加えて、均一に粉砕混合し、粉剤を得た。 [Formulation Example 3]
0.3 parts of the compound of the present invention represented by formula (1-1) or formula (1-2) and 0.3 parts of white carbon were uniformly mixed, and 99.2 parts of clay and 0.2 parts of Drilles A (manufactured by Sankyo Agro) were added thereto, and the mixture was uniformly ground and mixed to obtain a dust.
[製剤例４]
　式（１－１）、または式（１－２）で表される本発明化合物３部、ポリオキシエチレン・ポリオキシプロピレン縮合物１．５部、カルボキシメチルセルロース３部、クレー６４．８部、タルク２７．７部、以上を均一に粉砕混合後、水を加えて混練し、造粒乾燥して粒剤を得た。 [Formulation Example 4]
3 parts of the compound of the present invention represented by formula (1-1) or formula (1-2), 1.5 parts of polyoxyethylene-polyoxypropylene condensate, 3 parts of carboxymethylcellulose, 64.8 parts of clay, and 27.7 parts of talc were uniformly ground and mixed, and then water was added thereto, followed by kneading, granulation, and drying to obtain granules.
[製剤例５]
　式（１－１）、または式（１－２）で表される本発明化合物１０部、β‐ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩３部、トリスチリルフェノール１部、プロピレングリコール５部、シリコン系消泡剤０．５部、水３３．５部を十分撹拌混合した後、キサンタンガム０．３部、水４６．７部を混合したものと再び撹拌混合してフロアブル剤を得た。 [Formulation Example 5]
10 parts of the compound of the present invention represented by formula (1-1) or formula (1-2), 3 parts of β-naphthalenesulfonic acid formalin condensate sodium salt, 1 part of tristyrylphenol, 5 parts of propylene glycol, 0.5 parts of a silicone-based antifoaming agent, and 33.5 parts of water were thoroughly mixed with stirring, and then again mixed with a mixture of 0.3 parts of xanthan gum and 46.7 parts of water with stirring to obtain a flowable preparation.
[製剤例６]
　式（１－１）、または式（１－２）で表される本発明化合物２０部、ナフタレンスルホン酸ホルムアルデヒド縮合物金属塩６部、ジアルキルスルホコハク酸金属塩１部、炭酸カルシウム７３部、以上を均一に粉砕混合後、水を加えて混練し、造粒乾燥して顆粒水和剤を得た。 [Formulation Example 6]
20 parts of the compound of the present invention represented by formula (1-1) or formula (1-2), 6 parts of a naphthalenesulfonic acid formaldehyde condensate metal salt, 1 part of a dialkylsulfosuccinic acid metal salt, and 73 parts of calcium carbonate were uniformly ground and mixed, and then water was added and the mixture was kneaded, granulated, and dried to obtain a water dispersible granule.
　上記で得られた製剤の使用に際しては、上記製剤を水で１～１００００倍に希釈して、または希釈せずに直接散布する。 When using the formulation obtained above, it is diluted 1 to 10,000 times with water, or sprayed directly without dilution.
　次に、本発明化合物の有害生物防除剤としての有用性について、以下の試験例において具体的に説明するが、本発明はこれらのみに限定されるものではない。 Next, the usefulness of the compound of the present invention as a pest control agent will be specifically explained in the following test examples, but the present invention is not limited to these.
［試験例１］
　トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）に対する殺虫試験
　試験化合物を所定濃度に調製したアセトン溶液２．５ｍｌをイネ（Ｏｒｙｚａ　ｓａｔｉｖａ）幼苗に散布し、保水したガラス管に移した。風乾後、若齢幼虫を１０頭放飼しスポンジ栓で蓋をした。２５℃恒温室にて静置し、６日後に生死虫数を調査した。 [Test Example 1]
Insecticidal test against brown planthopper (Nilaparvata lugens) 2.5 ml of acetone solution containing a test compound at a given concentration was sprayed on rice (Oryza sativa) seedlings and transferred to a water-preserved glass tube. After air drying, 10 young larvae were released and the tube was capped with a sponge plug. The tube was left to stand in a thermostatic chamber at 25°C, and the number of live and dead insects was counted after 6 days.
　上記試験の結果、１００ｐｐｍの濃度で化合物番号１、２、３、４、５、６、７、９、１０、１１、１２、１３、１４、１５、１６、１７、１８、１９、２０、２１、２３、２４、２５、２６、２７、２８、２９、３０、３１、３２、３３、３４、３５、３６、３７、３９、４０、４１、４２、４３、４４、４５、４６、４７、４８、４９、５０、５１、５２、５３、５４、５５、５６、５８、５９、６０、６１、６２、６３、６４、６５、６６、６７、６８、６９、７０、７１、７２、７３、７４、７５、７６、７７、７８、７９、８０、８１、８２、８３、８４、８５、８６、８７、８８、８９、９０、９１、９２、９３、９４、９５、９６、９７、９８、１００、１０１、１０２、１０３、１０４、１０５、１０６、１０７、１０８、１０９、１１０、１１１、１１２、１１３、１１４、１１５、１１６、１１７、１１８、１１９、１２０、１２４、１２５、１２６、１２７、１３２、１３３、１３４、１３５、１３６、１３７、１３８、１３９、１４０、１４１、１４２、１４３、１４４、１４６、１４７、１４８、１４９、１５０、１５２、１５３、１５４、１５５、１５６、１５７、１５８、１５９、１６０、１６１、１６２、１６３、１６４、１６５、１６６、１６７、１６８、１６９、１７０、１７１、１７２、１７３、１７４、１７５、１７６、１７７、１７８、１７９、１８０、１８１、１８２、１８３、１８４、１８５、１８７、１８８、１８９、１９０、１９１、１９２、１９３、１９５、１９６、１９７、１９８、１９９、２００、２０１、２０２、２０３、２０４、２０５、２０６、２０７、２０８、２０９、２１０、２１１、２１２、２１３、２１４、２１５、２１６、２１７、２１８、２１９、２２０、２２１、２２２、２２３、２２４、２２５、２２６、２２７、２２８、２２９、２３０、２３１、２３２、２３３、２３４、２３５、２３６、２３７、２３８、２３９、２４０、２４１、２４２、２４３、２４４、２４５、２４６、２４７、２４８、２４９、２５０、２５１、２５２、２５３、２５４、２５５、２５６、２５７、２５８、２５９、２６０、２６１が５０％以上の死虫率を示した。 As a result of the above test, at a concentration of 100 ppm, compound numbers 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75 , 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 124, 125, 126, 127, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 146, 147, 148, 149, 150, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 187, 188, 189, 190, 191, 192, 193, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 2 08, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, and 261 showed a mortality rate of over 50%.
［試験例２］
　トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）に対する殺虫試験
試験化合物を所定濃度に調整した２％アセトン水溶液１２．５ｍｌを容器に入れ、スポンジとプラスチック製の筒で固定したイネ（Ｏｒｙｚａ　ｓａｔｉｖａ）幼苗の根部を浸漬した。そこに若齢幼虫を１０頭放飼しプラスチック製の蓋した。２５℃の恒温室にて静置し、６日後に生死虫数を調査した。 [Test Example 2]
Insecticidal test against brown planthopper (Nilaparvata lugens) 12.5 ml of 2% acetone aqueous solution containing a test compound adjusted to a predetermined concentration was placed in a container, and the roots of rice (Oryza sativa) seedlings fixed with a sponge and a plastic tube were immersed in the solution. Ten young larvae were released into the container and covered with a plastic lid. The container was left in a thermostatic chamber at 25°C, and the number of live and dead insects was counted after 6 days.
　上記試験の結果、１００ｐｐｍの濃度で、化合物番号４、５、６、７、１１、１３、１４、１７、１８、１９、２４、２５、２６、２７、２９、３０、３５、３７、３９、４２、５４、５５、５８、６２、６４、６５、７３、７５、７７、８０、８４、９４、９５、９７、９８、１００、１０４、１０６、１２５、１３３、１３６、１３７、１３９、１４０、１４１、１４３、１４８、１５１、１５２、１５６、１５７、１５８、１５９、１６７、１７２、１７５、１７７、１７９、１８０、１８１、１８２、１８３、１８４、１８５、１８８、１８９、１９０、１９１、１９２、１９３、１９４、１９８、１９９、２０１、２０５、２０９、２１４、２１６、２２０、２２６、２２７、２３７、２３９、２４０、２４２、２４３、２４６、２４７、２４８、２５０、２５４、２５７、２５９、２６０、２６１が５０％以上の死虫率を示した。 The results of the above test showed that at a concentration of 100 ppm, compounds No. 4, 5, 6, 7, 11, 13, 14, 17, 18, 19, 24, 25, 26, 27, 29, 30, 35, 37, 39, 42, 54, 55, 58, 62, 64, 65, 73, 75, 77, 80, 84, 94, 95, 97, 98, 100, 104, 106, 125, 133, 136, 137, 139, 140, 141, 143, 148, 151, 152, 156, 157, 158, 159, 167, 172, 175, 177, 179, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 192, 193, 194, 198, 199, 201, 205, 209, 214, 216, 220, 226, 227, 237, 239, 240, 242, 243, 246, 247, 248, 250, 254, 257, 259, 260, and 261 showed a mortality rate of more than 50%.
［試験例３］
　モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）に対する殺虫試験
　試験化合物を所定濃度に調製した２０％アセトン水溶液２．５ｍｌを、根元を保水し若齢幼虫を２５頭寄生させたダイコン（Ｒａｐｈａｎｕｓ　ｓａｔｉｖｕｓ）葉に散布した。風乾後、２５℃恒温室にて静置し、５日後に生死虫数を調査した。 [Test Example 3]
Insecticidal test against green peach aphid (Myzus persicae) 2.5 ml of 20% acetone aqueous solution containing a test compound at a given concentration was sprayed on a radish (Raphanus sativus) leaf with 25 young larvae infested at the base and kept moist. After air drying, the leaf was left in a thermostatic chamber at 25°C, and the number of dead and alive insects was counted after 5 days.
　上記試験の結果、１００ｐｐｍの濃度で化合物番号５、６、７、９、１１、１２、１４、１７、１８、２２、２３、２４、２６、２９、３０、３５、３７、４１、４２、４５、４８、４９、５０、５１、５２、５３、５５、５８、６０、６２、６４、６５、６８、７１、７３、７５、７７、７８、８０、８２、８３、８４、８６、８８、９１、９５、９７、９８、９９、１００、１０３、１０４、１０６、１０８、１０９、１１１、１１３、１１５、１１７、１２１、１２２、１２５、１２６、１２８、１３２、１３６、１３７、１３８、１３９、１４０、１４１、１４３、１４８、１５２、１５５、１５６、１５７、１５８、１６０、１６２、１６３、１６４、１６６、１６７、１６８、１６９、１７０、１７１、１７２、１７３、１７４、１７５、１７６、１７７、１７９、１８０、１８１、１８２、１８３、１８４、１８５、１８７、１８８、１８９、１９０、１９１、１９２、１９３、１９５、１９６、１９７、１９８、１９９、２００、２０１、２０２、２０３、２０４、２０５、２０６、２０７、２０８、２０９、２１０、２１１、２１２、２１３、２１４、２１５、２１６、２１７、２１８、２１９、２２０、２２１、２２２、２２３、２２４、２２５、２２６、２２７、２２９、２３０、２３２、２３４、２３５、２３７、２４０、２４３、２４４、２４５、２４６、２４８、２５４、２５５、２５７、２５８が５０％以上の死虫率を示した。 The results of the above test showed that at a concentration of 100 ppm, compounds No. 5, 6, 7, 9, 11, 12, 14, 17, 18, 22, 23, 24, 26, 29, 30, 35, 37, 41, 42, 45, 48, 49, 50, 51, 52, 53, 55, 58, 60, 62, 64, 65, 68, 71, 73, 75, 77, 78, 80, 82, 83, 84, 86, 88, 91, 95, 97, 98, 99, 100, 103, 104, 106, 108, 109, 111, 113, 115, 117, 121, 122, 125, 126, 128, 132, 136, 137, 138, 139, 140, 141, 143, 148, 152, 155, 156, 157, 158, 160, 162, 163, 164, 166, 167 , 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 183, 184, 185, 187, 188, 189, 190, 191, 192, 193, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 2 09, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 229, 230, 232, 234, 235, 237, 240, 243, 244, 245, 246, 248, 254, 255, 257, and 258 showed a mortality rate of over 50%.
［試験例４］
　モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）に対する殺虫試験
　試験化合物を所定濃度に調整した２％アセトン水溶液１２．５ｍｌを容器に入れ、スポンジで固定し、若齢幼虫を２５頭寄生させたダイコン（Ｒａｐｈａｎｕｓ　ｓａｔｉｖｕｓ）幼苗の根部を浸漬した。２５℃の恒温室にて静置し、５日後に生死虫数を調査した。 [Test Example 4]
Insecticidal test against green peach aphid (Myzus persicae) 12.5 ml of 2% aqueous acetone solution containing a test compound adjusted to a given concentration was placed in a container, and the roots of a radish (Raphanus sativus) seedling, which had been fixed with a sponge and infested with 25 young larvae, were immersed in the solution. The solution was left to stand in a thermostatic chamber at 25°C, and the number of live and dead insects was counted after 5 days.
　上記試験の結果、１００ｐｐｍの濃度で化合物番号９、１１、１２、１４、１８、２６、３７が５０％以上の死虫率を示した。 The results of the above test showed that compounds 9, 11, 12, 14, 18, 26, and 37 showed a mortality rate of 50% or more at a concentration of 100 ppm.
［試験例５］
　ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｔａ　ｌｉｔｕｒａ）に対する殺虫試験
試験化合物を所定濃度に調製した薬液にキャベツ（Ｂｒａｓｓｉｃａｅ　ｏｌｅｒａｃｅａ）葉片を３０秒間浸漬し風乾後、ろ紙を敷いた７ｃｍのポリエチレンカップに入れハスモンヨトウ２齢幼虫５頭を放虫した。２５℃恒温室にて静置し、６日後に生死虫数を調査した。 [Test Example 5]
Insecticidal test against Spodoptera litura: Cabbage (Brassicae oleracea) leaf pieces were immersed in a liquid containing a test compound at a prescribed concentration for 30 seconds, air-dried, and then placed in a 7 cm polyethylene cup lined with filter paper, into which five second-instar larvae of Spodoptera litura were released. The mixture was left to stand in a thermostatic chamber at 25°C, and the number of dead and alive insects was counted after 6 days.
　上記試験の結果、１０００ｐｐｍの濃度で化合物番号１１、１２、３２、３５、４１、４２、４５、４８、４９、５１、５２、５３、６５、６９、７１、８０、８４、８９、９１、９５、９８、１００、１０２、１０３、１０８、１１１、１１２、１１６、１１７、１２０、１２２、１２３、１２５、１３２、１４０、１４１、１４２、１４６、１４９、１５１、１５６、１５９、１６０、１７４、１７５、１８０、１８２、１８４、１８７、１９３、１９７、１９８、２０１、２１４、２１９、２２７、２３５、２４４、２５０、２５４、２５９が５０％以上の死虫率を示した。 As a result of the above test, at a concentration of 1000 ppm, compound numbers 11, 12, 32, 35, 41, 42, 45, 48, 49, 51, 52, 53, 65, 69, 71, 80, 84, 89, 91, 95, 98, 100, 102, 103, 108, 111, 112, 116, 117, 120, 122, and 123 , 125, 132, 140, 141, 142, 146, 149, 151, 156, 159, 160, 174, 175, 180, 182, 184, 187, 193, 197, 198, 201, 214, 219, 227, 235, 244, 250, 254, and 259 showed mortality rates of over 50%.
［試験例６］
　セジロウンカ（Ｓｏｇａｔｅｌｌａ　ｆｕｒｃｉｆｅｒａ）に対する殺虫試験
　試験化合物を所定濃度に調製したアセトン溶液２．５ｍｌをイネ（Ｏｒｙｚａ　ｓａｔｉｖａ）幼苗に散布し、保水したガラス管に移した。風乾後、若齢幼虫を１０頭放飼しスポンジ栓で蓋をした。２５℃恒温室にて静置し、６日後に生死虫数を調査した。 [Test Example 6]
Insecticidal test against white-backed planthopper (Sogatella furcifera) 2.5 ml of acetone solution containing a test compound at a given concentration was sprayed on rice (Oryza sativa) seedlings and transferred to a water-preserved glass tube. After air drying, 10 young larvae were released and the tube was capped with a sponge plug. The tube was left to stand in a thermostatic chamber at 25°C, and the number of live and dead insects was counted after 6 days.
　上記試験の結果、１００ｐｐｍで化合物番号５、６、７、１１、１５、１６、１７、１８、１９、２０、２１、２２、２４、２５、２６、２７、２８、２９、３０、３１、３５、３６、３７、３８、３９、４１、４２、４３、４４、４５、４６、４７、４８、４９、５０、５１、５２、５３、５４、５５、５７、５８、５９、６０、６１、６２、６３、６４、６５、６８、６９、７０、７１、７２、７３、７４、７５、７６、７７、７８、７９、８０、８１、８２、８３、８４、８５、８６、８７、８９、９０、９１、９２、９３、９４、９５、９６、９７、９８、９９、１００、１０１、１０３、１０４、１０５、１０６、１０７、１０８、１０９、１１１、１１２、１１３、１１４、１１５、１１６、１１７、１１８、１２４、１２５、１２６、１２９、１３０、１３１、１３３、１３４、１３５、１３６、１３７、１３８、１３９、１４０、１４１、１４２、１４３、１４４、１４５、１４７、１４８、１４９、１５０、１５１、１５２、１５５、１５６、１５７、１５８、１５９、１６０、１６１、１６２、１６３、１６４、１６６、１６７、１６８、１６９、１７０、１７１、１７２、１７３、１７４、１７５、１７６、１７７、１７９、１８０、１８１、１８２、１８３、１８４、１８５、１８６、１８７、１８８、１８９、１９０、１９１、１９２、１９３、１９５、１９６、１９７、２００、２０１、２０２、２０３、２０４、２０５、２０６、２０７、２０８、２０９、２１０、２１１、２１２、２１３、２１４、２１５、２１６、２１７、２１８、２１９、２２０、２２１、２２２、２２３、２２４、２２５、２２６、２２７、２２８、２２９、２３０、２３１、２３２、２３３、２３４、２３５、２３６、２３８、２３９、２４０、２４１、２４２、２４３、２４４、２４５、２４６、２４７、２４８、２４９、２５０、２５３、２５４、２５５、２５６、２５７、２５８、２５９、２６０、２６１が５０％以上の死虫率を示した。 As a result of the above test, at 100 ppm, compound numbers 5, 6, 7, 11, 15, 16, 17, 18, 19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 30, 31, 35, 36, 37, 38, 39, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 8 2, 83, 84, 85, 86, 87, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 103, 104, 105, 106, 107, 108, 109, 111, 112, 113, 114, 115, 116, 117, 118, 124, 125, 126, 129, 130, 131, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 147, 148, 149, 150, 151, 152, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 195, 196, 197, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 2 10, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 253, 254, 255, 256, 257, 258, 259, 260, and 261 showed a mortality rate of more than 50%.
　本発明のピラゾール化合物は新規な化合物であり、有害生物、特に有害節足動物を防除することができるため、農薬、例えば、農園芸用有害生物防除剤、特に農園芸用殺虫剤としての利用価値がある。 The pyrazole compound of the present invention is a novel compound that can control pests, particularly harmful arthropods, and is therefore useful as an agricultural chemical, for example, an agricultural and horticultural pest control agent, particularly an agricultural and horticultural insecticide.
　本明細書に記載された全ての文献、特許出願、および技術規格は、個々の文献、特許出願、および技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書に参照により取り込まれる。 All publications, patent applications, and technical standards described in this specification are incorporated by reference into this specification to the same extent as if each individual publication, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims (8)

  1. 式（１－１）または、式（１－２）
    Figure JPOXMLDOC01-appb-C000001
    ［式中、Ｒ１は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｃ２～Ｃ６のハロアルキニル基、
    　置換基Ｂで適宜０～５置換されてもよいフェニル基、
    　置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
    　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）、
    　または１～２個の酸素原子を含む３～６員環の基を表し；  
    Ｒ２は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｃ２～Ｃ６のハロアルキニル基、
    　置換基Ｂで適宜０～５置換されてもよいフェニル基、
    　置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）、
    　または１～２個の酸素原子を含む３～６員環の基を表し；  
    Ｒ３は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｃ２～Ｃ６のハロアルキニル基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
    Ｒ４は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｃ２～Ｃ６のハロアルキニル基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
    Ｒ５は、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｃ２～Ｃ６のハロアルキニル基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｈｅｔは、式（Ｈｅｔ）を表し；
    Figure JPOXMLDOC01-appb-C000002
    Ｇは、Ｃ－Ｒ６または窒素原子を表し；
    Ｒ６は、
    　水素原子、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、     
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　またはＣ２～Ｃ６のハロアルキニル基を表し；
    Ｒ７は、
    　水素原子、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　Ｃ２～Ｃ６のハロアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　またはＣ２～Ｃ６のハロアルキニル基を表し；
    Ｒ８は、
    　水素原子、
    　水酸基、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｒ９は、
    　水素原子、
    　水酸基、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｒ１０は、
    　水素原子、
    　水酸基、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    置換基Ａは、
    　水酸基、
    　シアノ基、
    　ニトロ基、
    　ハロゲン原子、
    　Ｃ３～Ｃ８のシクロアルキル基、
    　Ｃ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　Ｃ３～Ｃ８のシクロアルコキシ基、
    　置換基Ｃで適宜０～５置換されてもよいフェニル基、
    　置換基Ｃで適宜０～４置換されてもよい５～６員芳香族複素環基、
    　および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
    置換基Ｂは、
    　水酸基、
    　シアノ基、
    　ニトロ基、
    　ハロゲン原子、
    　Ｃ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　Ｃ３～Ｃ８のシクロアルキル基、
    　Ｃ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　Ｃ３～Ｃ８のシクロアルコキシ基、
    　およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５は、水酸基、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、Ｃ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、ｐは前記と同義である。）からなる群から選択される少なくとも１種であり；
    置換基Ｃは、
    　シアノ基、
    　ハロゲン原子、
    　Ｃ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　Ｃ３～Ｃ８のシクロアルキル基、
    　Ｃ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　Ｃ３～Ｃ８のシクロアルコキシ基、
    　およびＲｘ５Ｓ（Ｏ）ｐ－（ここで、Ｒｘ５およびｐは前記と同義である。）からなる群から独立して選択される少なくとも１種である。］で表される化合物またはその塩。     Formula (1-1) or Formula (1-2)
    Figure JPOXMLDOC01-appb-C000001
    [In the formula, R1 is
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkynyl group,
    a phenyl group optionally substituted with 0 to 5 substituents B;
    a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
    Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
    Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
    Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2.),
    or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
    R2 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkynyl group,
    a phenyl group optionally substituted with 0 to 5 substituents B;
    a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
    Rx3C(=O)- (wherein Rx3 has the same meaning as above),
    Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
    Rx4S(O)p- (wherein Rx4 and p are as defined above),
    or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
    R3 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkynyl group,
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above.)
    Rx3C(=O)- (wherein Rx3 has the same meaning as above),
    Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
    R4 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkynyl group,
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
    Rx3C(=O)- (wherein Rx3 has the same meaning as above),
    Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
    or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
    R5 is,
    Cyano group,
    Halogen atoms,
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkynyl group,
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    Het represents the formula (Het);
    Figure JPOXMLDOC01-appb-C000002
    G represents C-R6 or a nitrogen atom;
    R6 is,
    Hydrogen atoms,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    or a C2-C6 haloalkynyl group;
    R7 is,
    Hydrogen atoms,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2 to C6 haloalkenyl group,
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    or a C2-C6 haloalkynyl group;
    R8 is,
    Hydrogen atoms,
    Hydroxyl group,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    R9 is,
    Hydrogen atoms,
    Hydroxyl group,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    R10 is,
    Hydrogen atoms,
    Hydroxyl group,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    The substituent A is
    Hydroxyl group,
    Cyano group,
    Nitro group,
    Halogen atoms,
    a C3 to C8 cycloalkyl group,
    C1 to C6 alkoxy group,
    C1 to C6 haloalkoxy group,
    a C3 to C8 cycloalkoxy group,
    a phenyl group optionally substituted with 0 to 5 substituents C;
    a 5- or 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents C;
    and at least one selected from the group consisting of 3- to 6-membered ring groups containing 1 to 2 oxygen atoms;
    The substituent B is
    Hydroxyl group,
    Cyano group,
    Nitro group,
    Halogen atoms,
    C1 to C6 alkyl group,
    C1 to C6 haloalkyl groups,
    a C3 to C8 cycloalkyl group,
    C1 to C6 alkoxy group,
    C1 to C6 haloalkoxy group,
    a C3 to C8 cycloalkoxy group,
    and Rx5S(O)p- (wherein Rx5 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, or a C2-C6 haloalkynyl group, and p is as defined above);
    The substituent C is
    Cyano group,
    Halogen atoms,
    C1 to C6 alkyl group,
    C1 to C6 haloalkyl groups,
    a C3 to C8 cycloalkyl group,
    C1 to C6 alkoxy group,
    C1 to C6 haloalkoxy group,
    a C3 to C8 cycloalkoxy group,
    and Rx5S(O)p- (wherein Rx5 and p are as defined above).
  2. Ｒ１は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　またはＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）を表し；
    Ｒ２は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　またはＲｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）を表し；
    Ｒ３は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
    　またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
    Ｒ４は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
    Ｒ５は、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し；
    Ｇは、Ｃ－Ｒ６または窒素原子を表し；
    Ｒ６は、
    　水素原子、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
    Ｒ７は、
    　水素原子、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
    Ｒ８は、
    　水素原子、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、     
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｒ９は、
    　水素原子、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｒ１０は、
    　水素原子、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表す請求項１に記載の化合物またはその塩。     R1 is
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    or Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... a C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a phenyl group which may be optionally substituted with 0 to 5 substituents B, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, an azepanyl group, or an azocanyl group;
    R2 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    Or Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above);
    R3 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
    Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
    Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
    R4 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C2-C6 alkenyl group optionally substituted by a substituent A;
    a C2-C6 alkynyl group optionally substituted by a substituent A;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
    Rx3C(=O)- (wherein Rx3 has the same meaning as above),
    Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
    or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
    R5 is,
    Cyano group,
    Halogen atoms,
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    a C3-C8 cycloalkoxy group optionally substituted by a substituent A;
    or Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2);
    G represents C-R6 or a nitrogen atom;
    R6 is,
    Hydrogen atoms,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
    R7 is,
    Hydrogen atoms,
    Cyano group,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
    R8 is,
    Hydrogen atoms,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    R9 is,
    Hydrogen atoms,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkoxy group,
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    R10 is,
    Hydrogen atoms,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    or Rx4S(O)p- (wherein Rx4 and p are as defined above), or a salt thereof.
  3. Ｒ１は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
    Ｒ２は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　または置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基を表し；
    Ｒ３は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
    　またはＲｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
    Ｒ４は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は前記と同義である。）、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）、
    　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
    Ｒ５は、
    　シアノ基、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し；
    Ｇは、Ｃ－Ｒ６または窒素原子を表し；
    Ｒ６は、
    　水素原子、
    　ハロゲン原子、
    　または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
    Ｒ７は、
    　水素原子、
    　ハロゲン原子、
    　または置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
    Ｒ８は、
    　水素原子、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｒ９は、
    　水素原子、
    　ハロゲン原子、
    　Ｃ１～Ｃ６のハロアルキル基、
    　Ｃ１～Ｃ６のハロアルコキシ基、
    　またはＲｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４およびｐは前記と同義である。）を表し；
    Ｒ１０は、
    　水素原子、
    　ハロゲン原子、
    　またはＣ１～Ｃ６のハロアルキル基を表す請求項２に記載の化合物またはその塩。     R1 is
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
    R2 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    or a C3-C8 cycloalkyl group optionally substituted with a substituent A;
    R3 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
    Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
    Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
    R4 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are as defined above).
    Rx3C(=O)- (wherein Rx3 has the same meaning as above),
    Rx3OC(=O)- (wherein Rx3 has the same meaning as above),
    or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (however, when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
    R5 is,
    Cyano group,
    Halogen atoms,
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    or Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2);
    G represents C-R6 or a nitrogen atom;
    R6 is,
    Hydrogen atoms,
    Halogen atoms,
    or a C1-C6 alkyl group optionally substituted with a substituent A;
    R7 is,
    Hydrogen atoms,
    Halogen atoms,
    or a C1-C6 alkyl group optionally substituted with a substituent A;
    R8 is,
    Hydrogen atoms,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    C1 to C6 haloalkoxy group,
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    R9 is,
    Hydrogen atoms,
    Halogen atoms,
    C1 to C6 haloalkyl groups,
    C1 to C6 haloalkoxy group,
    or Rx4S(O)p- (wherein Rx4 and p are as defined above);
    R10 is,
    Hydrogen atoms,
    Halogen atoms,
    or a salt thereof.
  4. Ｒ１は、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
    Ｒ２は、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基を表し；
    Ｒ３は、
    　水素原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｒｘ３Ｃ（＝Ｏ）－（ここで、Ｒｘ３は、水素原子、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｂで適宜０～５置換されてもよいフェニル基、または置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表す。）、
    　または、Ｒｘ３ＯＣ（＝Ｏ）－（ここで、Ｒｘ３は前記と同義である。）を表し；
    Ｒ４は、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　Ｃ１～Ｃ６のハロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　Ｒｘ１Ｒｘ２ＮＣ（＝Ｏ）－（ここで、Ｒｘ１およびＲｘ２は、それぞれ独立していて、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、置換基Ｂで適宜０～５置換されてもよいフェニル基、置換基Ｂで適宜０～４置換されてもよい５～６員芳香族複素環基を表すか、あるいはＲｘ１およびＲｘ２は、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ピペラジニル基、モルホリニル基、チオモルホリニル基、ジオキソチオモルホリニル基、チアゾリジニル基、アゼパニル基、またはアゾカニル基を形成するものを表す。）、
    　または、５～６員の部分的不飽和ヘテロ環基、もしくは８～１０員の部分的不飽和ヘテロ環基〔該５～６員の部分的不飽和ヘテロ環、または該８～１０員の部分的不飽和ヘテロ環は、置換基Ｂが適宜０～６置換する（ただし、２置換以上の置換基Ｂがある場合、置換基Ｂはそれぞれ独立した置換基を表すか、同一となって３～６員環を形成してもよい。）。〕を表し；
    Ｒ５は、
    　Ｒｘ４Ｓ（Ｏ）ｐ－（ここで、Ｒｘ４は、水酸基、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、または置換基Ｂで適宜０～５置換されてもよいフェニル基を表し、ｐは、０、１、または２の整数を表す。）を表し；
    Ｇは、Ｃ－Ｒ６または窒素原子を表し；
    Ｒ６は、
    　水素原子を表し；
    Ｒ７は、
    　水素原子を表し；
    Ｒ８は、
    　水素原子、
    　ハロゲン原子、
    　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　またはＣ１～Ｃ６のハロアルキル基を表し；
    Ｒ９は、
    　水素原子、
    　ハロゲン原子、
    　またはＣ１～Ｃ６のハロアルキル基を表し；
    Ｒ１０は、
    　水素原子を表す請求項３に記載の化合物またはその塩。     R1 is
    represents a C1-C6 alkyl group optionally substituted with a substituent A;
    R2 is,
    represents a C1-C6 alkyl group optionally substituted with a substituent A;
    R3 is,
    Hydrogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    Rx3C(=O)- (wherein Rx3 represents a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2-C6 alkenyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group which may be optionally substituted with a substituent A, a C2-C6 haloalkynyl group, a phenyl group which may be optionally substituted with 0-5 substituents B, or a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0-4 substituents B.),
    Or Rx3OC(=O)- (wherein Rx3 has the same meaning as defined above);
    R4 is,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    C1 to C6 haloalkyl groups,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A;
    a C1-C6 alkoxy group optionally substituted with a substituent A;
    Rx1Rx2NC(=O)- (wherein Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, a C1 to C6 alkoxy ... C6 haloalkoxy group, C3-C8 cycloalkoxy group, phenyl group optionally substituted with 0-5 substituents B, 5- to 6-membered aromatic heterocyclic group optionally substituted with 0-4 substituents B, or Rx1 and Rx2, together with the nitrogen atom to which they are bonded, form an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group.
    or a 5- to 6-membered partially unsaturated heterocyclic group, or an 8- to 10-membered partially unsaturated heterocyclic group (the 5- to 6-membered partially unsaturated heterocyclic ring, or the 8- to 10-membered partially unsaturated heterocyclic ring is appropriately substituted with 0 to 6 substituents B (provided that when there are two or more substituents B, the substituents B may each represent an independent substituent or may be the same to form a 3- to 6-membered ring);
    R5 is,
    Rx4S(O)p- (wherein Rx4 represents a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2);
    G represents C-R6 or a nitrogen atom;
    R6 is,
    represents a hydrogen atom;
    R7 is,
    represents a hydrogen atom;
    R8 is,
    Hydrogen atoms,
    Halogen atoms,
    A C1-C6 alkyl group optionally substituted with a substituent A;
    or a C1-C6 haloalkyl group;
    R9 is,
    Hydrogen atoms,
    Halogen atoms,
    or a C1-C6 haloalkyl group;
    R10 is,
    A compound according to claim 3, or a salt thereof, wherein R represents a hydrogen atom.
  5. 　請求項１に記載の化合物またはその塩を有効成分として含有する有害生物防除剤。 A pest control agent containing the compound or salt thereof according to claim 1 as an active ingredient.
  6. 　請求項１に記載の化合物またはその塩を有効成分として含有する有害節足動物防除剤。 A harmful arthropod control agent containing the compound or salt thereof according to claim 1 as an active ingredient.
  7. 　請求項５に記載の有害生物防除剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、有害生物を防除する方法。 A method for controlling pests, comprising applying the pest control agent according to claim 5 to a plant, a seed of the plant, or the soil in which the plant is grown.
  8. 　請求項６に記載の有害節足動物防除剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、有害節足動物を防除する方法。 A method for controlling harmful arthropods, comprising applying the harmful arthropod control agent according to claim 6 to a plant, a plant seed, or the soil in which a plant is grown.
PCT/JP2023/035193 2022-09-28 2023-09-27 Pyrazole compound and pest control agent containing same as active ingredient WO2024071216A1 (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10152476A (en) * 1996-01-30 1998-06-09 Takeda Chem Ind Ltd 1-arylpyrazole derivative, its production and use
JP2014504267A (en) * 2010-11-03 2014-02-20 ダウ アグロサイエンシィズ エルエルシー Pesticide compositions and methods related thereto
WO2022066938A1 (en) * 2020-09-24 2022-03-31 Forkhead Biotherapeutics, Inc. Agents for the treatment of diseases by inhibition of foxo1
WO2022065235A1 (en) * 2020-09-25 2022-03-31 日本曹達株式会社 Imidazo[1,2-a]pyridine compound and pest control agent
WO2022186133A1 (en) * 2021-03-01 2022-09-09 日本農薬株式会社 Fused heterocycle compound having sulfonamide group or salt thereof, agricultural/horticultural pesticide and external or internal parasite controlling agent for animals containing said compound or salt thereof, and method of use therefor
WO2023171783A1 (en) * 2022-03-11 2023-09-14 三井化学アグロ株式会社 Pyrazole compound, and noxious organism control agent containing same as active ingredient

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10152476A (en) * 1996-01-30 1998-06-09 Takeda Chem Ind Ltd 1-arylpyrazole derivative, its production and use
JP2014504267A (en) * 2010-11-03 2014-02-20 ダウ アグロサイエンシィズ エルエルシー Pesticide compositions and methods related thereto
WO2022066938A1 (en) * 2020-09-24 2022-03-31 Forkhead Biotherapeutics, Inc. Agents for the treatment of diseases by inhibition of foxo1
WO2022065235A1 (en) * 2020-09-25 2022-03-31 日本曹達株式会社 Imidazo[1,2-a]pyridine compound and pest control agent
WO2022186133A1 (en) * 2021-03-01 2022-09-09 日本農薬株式会社 Fused heterocycle compound having sulfonamide group or salt thereof, agricultural/horticultural pesticide and external or internal parasite controlling agent for animals containing said compound or salt thereof, and method of use therefor
WO2023171783A1 (en) * 2022-03-11 2023-09-14 三井化学アグロ株式会社 Pyrazole compound, and noxious organism control agent containing same as active ingredient

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