WO2024071216A1 - Composé pyrazole et agent de lutte contre les organismes nuisibles le contenant en tant que principe actif - Google Patents

Composé pyrazole et agent de lutte contre les organismes nuisibles le contenant en tant que principe actif 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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Japanese (ja)
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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/fr

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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

La présente invention aborde le problème de la fourniture d'un nouveau composé pour lutter contre les organismes nuisibles. Un composé pyrazole amide selon l'invention est un nouveau composé qui peut lutter contre les organismes nuisibles. Le composé pyrazole amide selon l'invention comprend un composé représenté par la formule (1-1) ou la formule (1-2) et un sel de celui-ci.
PCT/JP2023/035193 2022-09-28 2023-09-27 Composé pyrazole et agent de lutte contre les organismes nuisibles le contenant en tant que principe actif WO2024071216A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10152476A (ja) * 1996-01-30 1998-06-09 Takeda Chem Ind Ltd １−アリールピラゾール誘導体、その製造法および用途
JP2014504267A (ja) * 2010-11-03 2014-02-20 ダウ アグロサイエンシィズ エルエルシー 殺有害生物剤組成物およびこれに関連した方法
WO2022066938A1 (fr) * 2020-09-24 2022-03-31 Forkhead Biotherapeutics, Inc. Agents pour le traitement de maladies par inhibition de foxo1
WO2022065235A1 (fr) * 2020-09-25 2022-03-31 日本曹達株式会社 Composé imidazo[1,2-a]pyridine et agent de lutte antiparasitaire
WO2022186133A1 (fr) * 2021-03-01 2022-09-09 日本農薬株式会社 Composé hétérocyclique fusionné ayant un groupe sulfonamide ou un sel de celui-ci, pesticide agricole/horticole et agent de lutte contre les parasites externe ou interne pour animaux contenant ledit composé ou sel de celui-ci, et procédé d'utilisation s'y rapportant
WO2023171783A1 (fr) * 2022-03-11 2023-09-14 三井化学アグロ株式会社 Composé pyrazole et agent de lutte contre des organismes nuisibles contenant ledit composé en tant que principe actif

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10152476A (ja) * 1996-01-30 1998-06-09 Takeda Chem Ind Ltd １−アリールピラゾール誘導体、その製造法および用途
JP2014504267A (ja) * 2010-11-03 2014-02-20 ダウ アグロサイエンシィズ エルエルシー 殺有害生物剤組成物およびこれに関連した方法
WO2022066938A1 (fr) * 2020-09-24 2022-03-31 Forkhead Biotherapeutics, Inc. Agents pour le traitement de maladies par inhibition de foxo1
WO2022065235A1 (fr) * 2020-09-25 2022-03-31 日本曹達株式会社 Composé imidazo[1,2-a]pyridine et agent de lutte antiparasitaire
WO2022186133A1 (fr) * 2021-03-01 2022-09-09 日本農薬株式会社 Composé hétérocyclique fusionné ayant un groupe sulfonamide ou un sel de celui-ci, pesticide agricole/horticole et agent de lutte contre les parasites externe ou interne pour animaux contenant ledit composé ou sel de celui-ci, et procédé d'utilisation s'y rapportant
WO2023171783A1 (fr) * 2022-03-11 2023-09-14 三井化学アグロ株式会社 Composé pyrazole et agent de lutte contre des organismes nuisibles contenant ledit composé en tant que principe actif

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