WO2013191189A1 - Composé hétérocyclique fusionné - Google Patents

Composé hétérocyclique fusionné Download PDF

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WO2013191189A1
WO2013191189A1 PCT/JP2013/066768 JP2013066768W WO2013191189A1 WO 2013191189 A1 WO2013191189 A1 WO 2013191189A1 JP 2013066768 W JP2013066768 W JP 2013066768W WO 2013191189 A1 WO2013191189 A1 WO 2013191189A1
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group
hydrogen atom
atom
formula
halogen atoms
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PCT/JP2013/066768
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English (en)
Japanese (ja)
Inventor
政樹 ▲高▼橋
貴將 田邊
舞衣 伊藤
千枝 清水
吉彦 野倉
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住友化学株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • A01N47/02—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 no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to certain condensed heterocyclic compounds and their use for pest control.
  • WO 88/02367 describes fused heterocyclic compounds that can be used in pharmaceuticals.
  • the present invention provides a compound having an excellent control effect against pests and a method for controlling pests using the compound.
  • the present invention is as follows. [1] Formula (1) [Where: A 1 represents —NR 6 —, an oxygen atom or a sulfur atom, R 1 may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, or one or more atoms or groups selected from group Y.
  • R 2 , R 3 , R 4 and R 5 are the same or different and are each a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, one or more atoms selected from group Z, or A phenyl group which may have a group, a 5- or 6-membered heterocyclic group which may have one or more atoms or groups selected from group Z, -OR 10 , -S (O) m R 10 , -NR 10 R 11, -CR 2 R 10, -C (O) R 10, represents a cyano group, a nitro group, a halogen atom, an -SF 5 or a hydrogen atom, R 6 may have a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from group X, and one or more atoms or groups selected from group Y.
  • C3-C6 alicyclic hydrocarbon group, -CO 2 R 10 represents -C (O) R 10 or a hydrogen atom
  • R 7 and R 8 do not simultaneously represent a hydrogen atom, and in —S (O) m R 10 , when m is 1 or 2, R 10 does not represent a hydrogen atom.
  • Group X C1-C6 alkoxy group optionally having one or more halogen atoms, C2-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms C2-C6 alkynyloxy group which may have one or more, C1-C6 alkylsulfanyl group which may have one or more halogen atoms, C1-C6 alkylsulfinyl group which may have one or more halogen atoms A C1-C6 alkylsulfonyl group which may have one or more halogen atoms, a C2-C6 alkylcarbonyl group which may have one or more halogen atoms, and one or more halogen atoms.
  • An optionally substituted C2-C6 alkoxycarbonyl group, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group The group consisting of fine-halogen atom.
  • Group Z C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms
  • R 7 and R 8 are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, —OR 10 , —S (O) m R 10 , halogen
  • R 9 is a hydrogen atom.
  • R 1 , R 4 and R 5 are the same or different and are a hydrogen atom or a halogen atom, and R 3 may have one or more halogen atoms, a C1-C6 chain hydrocarbon group,
  • [5] The compound according to [1] to [4], wherein A 1 is —NR 6 —.
  • a 1 is —NR 6 —, and R 6 may be a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, or may have one or more halogen atoms.
  • a 1 is an oxygen atom.
  • a 1 is a sulfur atom.
  • a pest control composition comprising the compound according to any one of [1] to [8] and an inert carrier.
  • a method for controlling pests which comprises applying an effective amount of the compound according to any one of [1] to [8] to a pest or a pest habitat.
  • the description of the Ca—Cb chain hydrocarbon group represents a linear or branched saturated or unsaturated hydrocarbon group having a to b carbon atoms.
  • the notation of the Ca—Cb alkyl group represents a linear or branched hydrocarbon group having a to b carbon atoms.
  • C1-C6 chain hydrocarbon group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, and a hexyl group.
  • a C1-C6 alkyl group such as, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl C2-C6 alkenyl groups such as 1-pentenyl group and 1-hexenyl group; and C2-C6 such as ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group and 1-hexynyl group An alkynyl group is mentioned.
  • the notation of the Ca-Cb alkenyl group refers to an unsaturated hydrocarbon group having one or more double bonds in the molecule, which is linear or branched having a carbon number of a to b.
  • Examples of the “C2-C6 alkenyl group” include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3 -A butenyl group, 1-pentenyl group, and 1-hexenyl group are mentioned.
  • the notation of the Ca-Cb alkynyl group represents an unsaturated hydrocarbon group having a linear or branched chain structure having a to b carbon atoms and having one or more triple bonds in the molecule.
  • Examples of the “C2-C6 alkynyl group” include ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group and 1-hexynyl group.
  • the notation of Ca—Cb alkoxy group represents a linear or branched alkyl-O— group having a to b carbon atoms.
  • Examples of the “C1-C6 alkoxy group” include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, neopentyloxy group and hexyl.
  • An oxy group is mentioned.
  • the notation of the Ca-Cb alkenyloxy group is an alkenyl-O- group which is linear or branched having 1 to 2 carbon atoms and has one or more double bonds in the molecule. Represents.
  • C2-C6 alkenyloxy group examples include a vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, 1-methylvinyloxy group, 2-methyl-1-propenyloxy group, 1-butenyloxy group, 2 -Butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group and 1-hexenyloxy group are mentioned.
  • the notation of a Ca-Cb alkynyloxy group is an alkynyl-O- group which is linear or branched having 1 to 2 carbon atoms and has one or more triple bonds in the molecule. To express.
  • C2-C6 alkynyloxy group examples include ethynyloxy group, propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group and 1-hexynyloxy group.
  • the notation of the Ca—Cb alkylsulfanyl group represents a linear or branched alkyl-S— group having a to b carbon atoms.
  • C1-C6 alkylsulfanyl group examples include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl group, and a hexylsulfanyl group.
  • the notation of the Ca—Cb alkylsulfinyl group represents a linear or branched alkyl-S (O) — group having a to b carbon atoms.
  • C1-C6 alkylsulfinyl group examples include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, and a hexylsulfinyl group.
  • the notation of the Ca—Cb alkylsulfonyl group is linear or branched alkyl-S (O) having a to b carbon atoms. 2 -Represents a group.
  • C1-C6 alkylsulfonyl group examples include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, and a hexylsulfonyl group.
  • the notation of Ca—Cb alkylcarbonyl group represents a linear or branched alkyl-C (O) — group having a to b carbon atoms.
  • Examples of the “C2-C6 alkylcarbonyl group” include an acetyl group, a propionyl group, a butyryl group, a pentanoyl group, and a hexanoyl group.
  • the notation of Ca—Cb alkoxycarbonyl group represents a linear or branched alkyl-O—C (O) — group having a to b carbon atoms.
  • Examples of the “C2-C6 alkoxycarbonyl group” include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, and a tert-butoxycarbonyl group.
  • the notation of the Ca—Cb alicyclic hydrocarbon group represents a cyclic non-aromatic hydrocarbon group having a to b carbon atoms.
  • Examples of the “C3-C6 alicyclic hydrocarbon group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a 2-cyclohexenyl group, and a 3-cyclohexenyl group.
  • the notation of Ca—Cb cycloalkyl group represents a cyclic alkyl group having a to b carbon atoms.
  • Examples of the “C3-C6 cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • the notation of Ca—Cb alkylamino group represents a linear or branched alkyl-NH— group having a to b carbon atoms.
  • Examples of the “C1-C6 alkylamino group” include a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, and a butylamino group.
  • the notation of the Ca-Cb dialkylamino group may be a linear or branched dialkylamino in which the number of carbon atoms of the alkyl group may be the same or different, and the total number of carbon atoms is a to b. Represents a group.
  • Examples of the “C2-C8 dialkylamino group” include a dimethylamino group, a diethylamino group, and a dipropylamino group.
  • the notation of the Ca-Cb alkoxyalkyl group may be the same or different from each other in the number of carbon atoms of the alkyl group, and a linear or branched alkyl group in which the total number of carbon atoms is a to b.
  • Examples of the “(C1-C6 alkoxy) C1-C6 alkyl group” include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, a 2- (methoxy) ethyl group, a 1- (ethoxy) ethyl group, 2 -(Ethoxy) ethyl group etc. are mentioned.
  • the expression “may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, those The atoms or groups selected from group X may be the same or different.
  • the expression “which may have one or more atoms or groups selected from group Y” means that when it has two or more atoms or groups selected from group Y, those The atoms or groups selected from group Y may be the same as or different from each other.
  • the expression “may have one or more atoms or groups selected from group Z” means that when it has two or more atoms or groups selected from group Z, those The atoms or groups selected from group Z may be the same or different from each other.
  • halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the notation of “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” is selected from group X in which a hydrogen atom bonded to a carbon atom is selected.
  • Examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.
  • C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y indicates that the hydrogen atom bonded to the carbon atom is selected from group Y
  • group Y represents a cyclic non-aromatic hydrocarbon group having 3 to 6 carbon atoms, optionally substituted by any atom or group having at least two atoms or groups selected from group Y
  • the atoms or groups selected from those groups Y may be the same or different.
  • C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and 1-cyclohexenyl.
  • C1-C6 chain hydrocarbon group optionally having one or more halogen atoms is a carbon atom in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • C1-C6 chain hydrocarbon group optionally having one or more halogen atoms examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, tert-butyl, pentyl, neopentyl, hexyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoro C1-C6 alkyl group optionally having one or more halogen atoms such as ethyl group, heptafluoropropyl group, heptafluoroisopropyl group; vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl Group, 2-methyl-1-propenyl group, 1-butenyl group,
  • phenyl group optionally having one or more atoms or groups selected from group Z is arbitrarily selected depending on the atom or group selected from group Z in which a hydrogen atom bonded to a carbon atom is selected.
  • a substituted phenyl group is represented, and at this time, when it has two or more atoms or groups selected from group Z, the atoms or groups selected from group Z may be the same as or different from each other.
  • phenyl group optionally having one or more atoms or groups selected from group Z examples include a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, 2, 3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3, 4,5,6-pentafluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2-trifluoromethylphenyl group,
  • the “heterocyclic group” represents a heterocyclic compound residue containing at least one nitrogen atom, oxygen atom and sulfur atom in addition to the carbon atom in the ring structure.
  • the 5-membered heterocyclic group means a 5-membered aromatic heterocyclic group or a 5-membered non-aromatic heterocyclic group
  • the 6-membered heterocyclic group means a 6-membered aromatic heterocyclic group. Or a 6-membered non-aromatic heterocyclic group is meant.
  • the “heterocyclic group” in the “5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” means nitrogen other than carbon atoms in the ring structure. Represents a heterocyclic compound residue containing at least one atom, oxygen atom and sulfur atom. At this time, when it has two or more atoms or groups selected from group Z, an atom selected from group Z Alternatively, the groups may be the same or different from each other.
  • the “5- or 6-membered heterocyclic group” means a 5- or 6-membered aromatic heterocyclic group or a 5- or 6-membered non-aromatic heterocyclic group.
  • Examples of the “5- or 6-membered heterocyclic group optionally having one or more atoms or groups selected from group Z” include pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidine It may have one or more atoms or groups selected from the group Z such as -1-yl group, tetrahydrofuran-2-yl group, piperidyl group, morpholinyl group, thiomorpholinyl group, etc.
  • Aromatic heterocyclic group and 2-pyrrolyl group, 2-furyl group, 3-furyl group, 5-pyrazolyl group, 4-pyrazolyl group, 1-pyrrolyl group, 1-methyl-2-pyrrolyl group, 2-methylsulfanyl -1-pyrrolyl group, 2-methylsulfinyl-1-pyrrolyl group, 2-methylsulfonyl-1-pyrrolyl group, 2-methylamino-1-pyrrolyl group, 2-dimethylamino-1-pyrrole Group, 5-bromo-2-furyl group, 5-nitro-2-furyl group, 5-cyano-2-furyl group, 5-methoxy-2-furyl group, 5-acetyl-2-furyl group, 5- Methoxycarbonyl-2-furyl group, 2-methyl-3-furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl-3-furyl group, 5-methyl-2-thienyl group, 3- Methyl-2-thieny
  • C1-C6 alkoxy group optionally having one or more halogen atoms in the compound of the present invention include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, Examples thereof include a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.
  • Examples of the “C2-C6 alkenyloxy group optionally having one or more halogen atoms” in the compound of the present invention include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2-butenyloxy group, Examples include 3-butenyloxy group, 2-pentenyloxy group, 2-hexenyloxy group, 3,3-difluoroallyloxy group, and 3,3-dichloroallyloxy group.
  • Examples of the “C2-C6 alkynyloxy group optionally having one or more halogen atoms” in the compound of the present invention include a propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, Examples include 2-hexynyloxy group and 4,4,4-trifluoro-2-butynyloxy group.
  • Examples of the “C1-C6 alkylsulfanyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, and pentyl. Examples thereof include a sulfanyl group, a hexylsulfanyl group, a trifluoromethylsulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, and a pentafluoroethylsulfanyl group.
  • Examples of the “C1-C6 alkylsulfinyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, and pentyl.
  • Examples thereof include a sulfinyl group, a hexylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, and a pentafluoroethylsulfinyl group.
  • Examples of the “C1-C6 alkylsulfonyl group optionally having one or more halogen atoms” in the compound of the present invention include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, and pentyl.
  • Examples include a sulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, and a pentafluoroethylsulfonyl group.
  • examples of the C2-C6 alkylcarbonyl group which may have one or more halogen atoms include acetyl group, propionyl group, butyryl group, pentanoyl group, hexanoyl group and trifluoroacetyl group. It is done.
  • Examples of the “C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms” in the compound of the present invention include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, Examples thereof include a tert-butoxycarbonyl group and a 2,2,2-trifluoroethoxycarbonyl group.
  • Examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” in the compound of the present invention include a cyclopropyl group, a 2,2-difluorocyclopropyl group, and a 2,2-dichlorocyclopropyl group. 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
  • Examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a methylamino group, an ethylamino group, a 2,2,2-trifluoroethylamino group, propyl An amino group, an isopropylamino group, and a butylamino group are mentioned.
  • Examples of the “C2-C8 dialkylamino group optionally having one or more halogen atoms” in the compound of the present invention include a dimethylamino group, a diethylamino group, and a bis (2,2,2-trifluoroethyl) amino group. And a dipropylamino group.
  • examples of the “(C1-C6 alkoxy) C1-C6 alkyl group optionally having one or more halogen atoms” include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, Examples include 2- (methoxy) ethyl group, 1- (ethoxy) ethyl group and 2- (ethoxy) ethyl group.
  • a “5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a halogen atom).
  • the group may have one or more atoms or groups selected from the group consisting of C1-C3 alkoxy groups which may have an atom.
  • C1-C6 haloalkyl group is represented by a linear or branched chain having 1 to 6 carbon atoms in which one or more hydrogen atoms bonded to carbon atoms are substituted with halogen atoms. In this case, when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
  • C1-C6 haloalkyl group examples include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, and trichloromethyl.
  • examples of the “C1-C6 perfluoroalkyl group” include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.
  • “(C1-C6 alkoxy) C1-C6 alkyl group” is a C1-C6 alkyl group substituted with a C1-C6 alkoxy group.
  • the carbon number is, for example, 2-6.
  • a “(C1-C6 alkoxy) C1-C6 alkyl group” having this carbon number can be represented as a “C2-C6 alkoxyalkyl group”. Examples of the compound of the present invention include the following compounds.
  • a 1a Is -NR 6a -Represents an oxygen atom or a sulfur atom
  • R 1a Is a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms or 1
  • a C2-C6 alkenyl group which may have one or more halogen atoms, a C2 which may have one or more halogen atoms.
  • R 2a , R 4a And R 5a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a Has a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms.
  • a C2-C6 alkynyl group, a 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and One or more atoms or substituents selected from the group consisting of C1-C3 alkoxy groups optionally having halogen atoms may be present), -OR 20a (Where R 20a Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 21a (Where R 21a Represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), A cyano group, a nitro group, a halogen atom or a hydrogen atom, R 6a Has a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms.
  • R 8a Represents a good C3-C6 alkynyl group
  • R 8a Is a C1-C6 alkyl group optionally having one or more halogen atoms
  • -OR 22a where R 22a Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • -S (O) m R 23a where R 23a Represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2.
  • R 1b Represents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group
  • R 6b Represents a methyl group or a propargyl group
  • R 2b , R 4b And R 5b Are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3b Is a C1-C6 alkyl group optionally having one or more halogen atoms
  • -OR 20b where R 20b Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 21b (Where R 21b Represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom, R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Represents a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Represents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF 5 Or a halogen atom, n represents 0, 1 or 2. ] The compound shown.
  • R 1b Represents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group
  • R 2b , R 4b And R 5b Are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3b Is a C1-C6 alkyl group optionally having one or more halogen atoms
  • -OR 20b where R 20b Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 21b (Where R 21b Represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom, R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Represents a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Represents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF 5 Or a halogen atom, n represents 0, 1 or 2. ] The compound shown.
  • R 1b Represents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group
  • R 2b , R 4b And R 5b Are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3b Is a C1-C6 alkyl group optionally having one or more halogen atoms
  • -OR 20b where R 20b Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 21b (Where R 21b Represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom, R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Represents a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Represents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF 5 Or a halogen atom, n represents 0, 1 or 2. ] The compound shown.
  • R 1b Represents an ethyl group, a cyclopropyl group or a cyclopropylmethyl group
  • R 60b Represents a hydrogen atom or a (C1-C6 alkoxy) C1-C6 alkyl group optionally having one or more halogen atoms
  • R 3b Is a C1-C6 alkyl group optionally having one or more halogen atoms
  • -OR 20b where R 20b Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 21b (Where R 21b Represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2. ), Represents a halogen atom or a hydrogen atom, R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Represents a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Represents a C1-C6 haloalkyl group, and m represents 0, 1 or 2. ), -SF 5 Or a halogen atom, n represents 0, 1 or 2. ] The compound shown.
  • a 1 -NR 6 A compound that is-.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, and R 6 Is a C1-C6 chain hydrocarbon group, (C1-C6 alkoxy) C1-C6 alkyl group, cyclopropyl group or hydrogen atom which may have one or more halogen atoms.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, and R 6 Is a C1-C6 chain hydrocarbon group, (C1-C6 alkoxy) C1-C6 alkyl group or cyclopropyl group optionally having one or more halogen atoms.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, and R 6 Is a C1-C6 alkyl group.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, and R 6 Is a methyl group, ethyl group, propyl group, isopropyl group, methoxymethyl group, ethoxymethyl group or cyclopropyl group.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, and R 6 Is a methyl group.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, and R 6 In which is a hydrogen atom.
  • a 1 -NR 6 -And R 6 C1-C6 chain hydrocarbon group which may have one or more halogen atoms, (C1-C6 alkoxy) C1-C6 alkyl group or cyclopropyl which may have one or more halogen atoms A compound that is a group.
  • a 1 -NR 6 -And R 6 Is a C1-C6 alkyl group.
  • a 1 -NR 6 -And R 6 Is a methyl group, ethyl group, propyl group, isopropyl group, methoxymethyl group, ethoxymethyl group, cyclopropyl group or hydrogen atom.
  • a 1 -NR 6 -And R 6 Is a methyl group, ethyl group, propyl group, isopropyl group, methoxymethyl group, ethoxymethyl group or cyclopropyl group.
  • a 1 -NR 6 -And R 6 Is a methyl group.
  • a 1 -NR 6 -And R 6 In which is a methyl group or a hydrogen atom.
  • a 1 -NR 6 -And R 6 In which is a hydrogen atom.
  • a 1 -NR 6 -And R 8 In which is a methoxymethyl group, an ethoxymethyl group or a hydrogen atom.
  • R 1 Is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from group X. In equation (1), R 1 Is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms. In equation (1), R 1 Is a C1-C6 chain hydrocarbon group optionally having one or more fluorine atoms. In equation (1), R 1 Is a C1-C6 chain hydrocarbon group. In equation (1), R 1 Is a C1-C6 alkyl group. In equation (1), R 1 Is a C1-C3 alkyl group.
  • R 1 Is a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from group Y.
  • R 1 Is a C3-C6 alicyclic hydrocarbon group.
  • R 1 In which is a cyclopropyl group, a cyclobutyl group or a cyclopentyl group.
  • R 1 Is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, cyclopropylmethyl, cyclopropyl, trifluoromethyl, 2,2,2-tri A compound that is a fluoroethyl group.
  • R 1 Is a methyl group, an ethyl group, a cyclopropyl group, a cyclopropylmethyl group or a propyl group.
  • R 1 In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 1 Is an ethyl group or a cyclopropylmethyl group.
  • R 1 Is a methyl group.
  • R 1 Is an ethyl group.
  • R 1 Is a propyl group.
  • R 1 In which is an isopropyl group.
  • R 1 Is a cyclopropyl group. In equation (1), R 1 Is a cyclopropylmethyl group. In equation (1), R 1 In which is a trifluoromethyl group. In equation (1), R 1 Is a 2,2,2-trifluoroethyl group.
  • R 2 , R 3 , R 4 And R 5 Are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, -OR 10 , -S (O) mR 10 , -C (O) R 10 , -CO 2 R 10 , -NR 10 R 11 , Formyl group, cyano group, nitro group, halogen atom or hydrogen atom, R 10 And R 11 Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
  • R 2 , R 3 , R 4 And R 5 In which is a hydrogen atom.
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom, and R 3 C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR 10 , -S (O) m R 10 , -C (O) R 10 , -CO 2 R 10 , -NR 10 R 11
  • R 10 And R 11 Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom, and R 3 C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR 10 A halogen atom or a hydrogen atom, R 10 Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more halogen atoms.
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom, and R 3 Is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom.
  • R 2 , R 4 And R 5 are the same or different and are a halogen atom or a hydrogen atom
  • R 3 Is a methyl group, ethyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, -OR 10 A halogen atom or a hydrogen atom, R 10 Is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a methyl group, ethyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, trifluoromethoxy group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a methyl group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is an ethyl group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a trifluoromethyl group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a pentafluoroethyl group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a heptafluoropropyl group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a trifluoromethoxy group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a fluorine atom.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a chlorine atom.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a bromine atom.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is an iodine atom.
  • R 2 , R 4 And R 5 are the same or different and are a halogen atom or a hydrogen atom
  • R 3 A phenyl group which may have one or more atoms or groups selected from group Z, a 5-membered heterocyclic group which may have one or more atoms or groups selected from group Z, group Z A compound which is a 6-membered heterocyclic group optionally having one or more atoms or groups selected.
  • R 2 , R 4 And R 5 are the same or different and are a halogen atom or a hydrogen atom
  • R 3 Is a phenyl group optionally having one or more halogen atoms or a C1-C3 alkyl group optionally having one or more halogen atoms, or one or more halogen atoms or one or more halogen atoms.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a 2-pyridyl group, 2-pyrimidinyl group, 3-chloro-2-pyridyl group or 3-chloro-5-trifluoromethyl-2-pyridyl group.
  • R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is 2-pyridyl group, 2-pyrimidinyl group, 3-chloro-2-pyridyl group, 3-chloro-5-trifluoromethyl-2-pyridyl group, methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl Group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, fluorine atom, chlorine atom or bromine atom.
  • R 1 Is an ethyl group and R 2 , R 3 , R 4 And R 5 In which is a hydrogen atom.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a methyl group.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a trifluoromethyl group.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a pentafluoroethyl group.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a heptafluoropropyl group.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 Is a 2-pyrimidinyl group.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a trifluoromethoxy group.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a chlorine atom.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is a bromine atom.
  • R 1 Is an ethyl group and R 2 , R 4 And R 5 Is a hydrogen atom and R 3 In which is an iodine atom.
  • R 7 And R 8 Are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, -OR 10 , -S (O) m R 10 , -NR 10 R 11 , -CO 2 R 10 , -C (O) R 10 , A cyano group, a nitro group, a halogen atom or a hydrogen atom, R 10 And R 11 Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
  • R 7 And R 8 Are the same or different and may have one or more halogen atoms, a C1-C6 chain hydrocarbon group, -OR 10 , -S (O) m R 10 A halogen atom or a hydrogen atom, R 10 Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more halogen atoms.
  • R 7 And R 8 Are the same or different and are a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more halogen atoms.
  • R 7 And R 8 are the same or different, trifluoromethyl group, difluoromethyl group, fluoromethyl group, pentafluoroethyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms, and R 7 In which is a hydrogen atom.
  • R 8 Is a C1-C3 alkoxy group having one or more fluorine atoms, and R 7 In which is a hydrogen atom.
  • R 8 Is a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1- having one or more fluorine atoms.
  • R 8 Is a halogen atom and R 7 In which is a hydrogen atom.
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkyl having one or more fluorine atoms A sulfanyl group, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R 7 In which is a hydrogen atom.
  • R 8 Is a trifluoromethyl group, pentafluoroethyl group, heptafluoroisopropyl group, trifluoromethoxy group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, bromine atom or iodine atom, R 7 In which is a hydrogen atom.
  • R 8 Is a bromine atom and R 7 In which is a hydrogen atom.
  • R 8 Is an iodine atom and R 7 In which is a hydrogen atom.
  • R 8 Is a trifluoromethyl group and R 7 In which is a hydrogen atom.
  • R 8 Is a pentafluoroethyl group and R 7 In which is a hydrogen atom.
  • R 8 Is a trifluoromethoxy group and R 7 In which is a hydrogen atom.
  • R 8 Is a trifluoromethylsulfanyl group and R 7 In which is a hydrogen atom.
  • R 8 Is a trifluoromethylsulfinyl group and R 7 In which is a hydrogen atom.
  • R 8 Is a trifluoromethylsulfonyl group, R 7 In which is a hydrogen atom.
  • R 8 Is a heptafluoroisopropyl group and R 7 In which is a hydrogen atom.
  • R 9 In which is a hydrogen atom.
  • a compound in which n is 0 in formula (1).
  • a compound in which n is 1 in the formula (1).
  • a compound in which n is 2 in the formula (1).
  • a compound in which m is 0 in formula (1).
  • a compound wherein m is 1.
  • a compound wherein m is 2.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom
  • R 6 Is a C1-C6 alkyl group
  • R 1 Is a C1-C3 alkyl group or cyclopropyl group optionally having one or more fluorine atoms
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom
  • R 3 C1-C3 alkyl group optionally having one or more fluorine atoms, 5- or 6-membered heterocyclic group
  • C1-C3 alkoxy group optionally having one or more fluorine atoms, a halogen atom or A hydrogen atom
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkyl having one or more fluorine atoms A sulfanyl group,
  • a 1 -NR 6 ⁇ R 6 Is a C1-C6 alkyl group
  • R 1 Is a C1-C3 alkyl group or cyclopropyl group optionally having one or more fluorine atoms
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom
  • R 3 Is a C1-C3 alkyl group which may have one or more fluorine atoms, a C1-C3 alkoxy group which may have one or more fluorine atoms, a 5- or 6-membered heterocyclic group, a halogen atom or A hydrogen atom
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkyl having one or more fluorine atoms A sulfanyl group, a C1-
  • a 1 -NR 6 ⁇ R 6 Is a methyl group, an ethyl group, a propyl group or an isopropyl group
  • R 1 Is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group
  • R 2 , R 4 And R 5 Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom
  • R 3 Is methyl, ethyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, trifluoromethoxy, 2-pyrimidinyl, fluorine, chlorine, bromine
  • R 8 Is a trifluor
  • a 1 Is a sulfur atom
  • R 1 Is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group
  • R 2 , R 4 And R 5 Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom
  • R 3 Is methyl, ethyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, trifluoromethoxy, 2-pyrimidinyl, fluorine, chlorine, bromine
  • R 8 Is a trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, hept
  • a 1 Is an oxygen atom
  • R 1 Is a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group
  • R 2 , R 4 And R 5 Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom
  • R 3 Is methyl, ethyl, propyl, isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, trifluoromethoxy, 2-pyrimidinyl, fluorine, chlorine, bromine
  • R 8 Is a trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, hepta
  • a 1 -NR 6 - An oxygen atom or a sulfur atom
  • R 6 Is a C1-C6 alkyl group
  • R 1 Is a C1-C3 alkyl group or cyclopropyl group optionally having one or more fluorine atoms
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom
  • R 3 C1-C3 alkyl group optionally having one or more fluorine atoms, 5- or 6-membered heterocyclic group
  • C1-C3 alkoxy group optionally having one or more fluorine atoms, a halogen atom or A hydrogen atom
  • a 1 -NR 6 - An oxygen atom or a sulfur atom
  • R 1 Is an ethyl group or a cyclopropyl group
  • R 2 , R 4 And R 5 Are the same or different and are a fluorine atom, a chlorine atom, or a hydrogen atom
  • R 3 Is a methyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, trifluoromethoxy group, 2-pyrimidinyl group, fluorine atom, chlorine atom, bromine atom or hydrogen atom
  • R 8 Is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylsulfanyl group or a trifluoromethylsulfonyl group
  • R 7 Is a hydrogen atom
  • R 9 Is a hydrogen atom
  • a compound wherein n is 2.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom
  • R 6 Is a C1-C6 alkyl group
  • R 1 Is a C1-C3 alkyl group optionally having one or more fluorine atoms
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom
  • R 3 Is a C1-C3 alkyl group which may have one or more fluorine atoms or a hydrogen atom
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms or a C1-C3 alkylsulfonyl group having one or more fluorine atoms
  • R 7 Is a hydrogen atom
  • R 9 Is a hydrogen atom
  • a compound wherein n is 2.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, R 6 Is a C1-C3 alkyl group, R 1 Is a C1-C3 alkyl group optionally having one or more fluorine atoms, R 2 Is a halogen atom or a hydrogen atom, R 3 Is a C1-C3 alkyl group which may have one or more fluorine atoms or a hydrogen atom, R 4 And R 5 Is a hydrogen atom, R 8 Is a C1-C3 alkyl group having one or more fluorine atoms or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R 7 Is a hydrogen atom, R 9 Is a hydrogen atom, A compound wherein n is 2.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom
  • R 1 Is an ethyl group
  • R 2 Is a chlorine atom or a hydrogen atom
  • R 3 Is a trifluoromethyl group or a hydrogen atom
  • R 4 And R 5 Is a hydrogen atom
  • R 8 Is a trifluoromethyl group, a pentafluoroethyl group or a trifluoromethylsulfonyl group
  • R 7 Is a hydrogen atom
  • R 9 Is a hydrogen atom
  • a compound wherein n is 2.
  • a 1 -NR 6 ⁇ R 6 Is a C1-C6 alkyl group
  • R 1 Is a C1-C3 alkyl group optionally having one or more fluorine atoms
  • R 2 , R 4 And R 5 Are the same or different and are a halogen atom or a hydrogen atom
  • R 3 Is a C1-C3 alkyl group having one or more fluorine atoms or a hydrogen atom
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms
  • R 7 Is a hydrogen atom
  • R 9 Is a hydrogen atom
  • a compound wherein n is 2.
  • a 1 -NR 6 ⁇ R 6 Is a C1-C3 alkyl group
  • R 1 Is a C1-C3 alkyl group optionally having one or more fluorine atoms
  • R 2 Is a halogen atom or a hydrogen atom
  • R 3 Is a C1-C3 alkyl group having one or more fluorine atoms or a hydrogen atom
  • R 4 And R 5 Is a hydrogen atom
  • R 8 Is a C1-C3 alkyl group having one or more fluorine atoms
  • R 7 Is a hydrogen atom
  • R 9 Is a hydrogen atom
  • a compound wherein n is 2.
  • a 1 -NR 6 - An oxygen atom or a sulfur atom, R 1 Is an ethyl group, R 2 Is a chlorine atom or a hydrogen atom, R 3 Is a trifluoromethyl group or a hydrogen atom, R 4 And R 5 Is a hydrogen atom, R 8 Is a trifluoromethyl group, R 7 Is a hydrogen atom, R 9 Is a hydrogen atom, A compound wherein n is 2.
  • a 1a -NR 6a A compound that is-.
  • R 1a C1-C6 alkyl group optionally having one or more atoms or groups selected from the group consisting of halogen atoms and cyclopropyl groups (wherein the cyclopropyl group is one or more halogen atoms or 1 And a compound which may have one or more C1-C3 alkyl groups).
  • R 1a Is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group has one or more halogen atoms or one or more C1-C3 alkyl groups).
  • R 1a Is a C2-C6 alkyl group, a C1-C6 haloalkyl group or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group has one or more halogen atoms or one or more C1-C3 alkyl groups).
  • R 1a Is a methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group or cyclopropylmethyl group.
  • R 1a In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 1a Is an ethyl group or a cyclopropylmethyl group.
  • R 1a Is a C1-C6 alkyl group.
  • R 1a In which is a C2-C6 alkyl group.
  • R 1a Is a C1-C3 alkyl group.
  • R 1a Is an ethyl group.
  • R 2a , R 4a And R 5a Are the same or different and are a halogen atom or a hydrogen atom.
  • R 2a , R 4a And R 5a Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2a , R 4a And R 5a Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4a And R 5a Is a hydrogen atom and R 2a In which is a chlorine atom.
  • R 2a , R 4a And R 5a Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2a , R 4a And R 5a Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4a And R 5a Is a hydrogen atom and R 2a In which is a chlorine atom.
  • R 2a , R 4a And R 5a In which is a hydrogen atom.
  • R 3a Has a C1-C6 alkyl group which may have one or more halogen atoms, a C2-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms.
  • pyridyl group (wherein the pyridyl group is a halogen atom, a C1-C3 alkyl group optionally having a halogen atom, and a C1-C3 optionally having a halogen atom)
  • a pyrimidinyl group (wherein the pyrimidinyl group may have a halogen atom or a halogen atom) It may have one or more atoms or substituents selected from the group consisting of a C3 alkyl group and a C1-C3 alkoxy group optionally having a halogen atom.
  • R 20a (Where R 20a Is a C1-C6 alkyl group optionally having one or more halogen atoms. ), -S (O) m R 21a (Where R 21a Is a C1-C6 alkyl group optionally having one or more halogen atoms, and m is 0, 1 or 2. ), A compound which is a halogen atom or a hydrogen atom.
  • R 3a C 1 -C 6 alkyl group optionally having one or more halogen atoms, —OR 20a (Where R 20a Represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 21a represents a C1-C6 alkyl group which may have one or more halogen atoms, and m represents 0, 1 or 2.
  • R 3a Is methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, pentafluoroethyl (-CF 2 CF 3 ), Heptafluoropropyl group (-CF 2 CF 2 CF 3 ), -CF (CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , A trifluoromethoxy group (-OCF 3 ), -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , 2-pyridyl group, 5-trifluoromethyl-2-pyridyl group, 2-pyrimidinyl group, a fluorine atom, a chlorine
  • R 3a are methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , 2-pyrimidinyl group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom.
  • R 3a Trifluoromethyl group, ethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -OCF 3 , 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
  • R 3a In which is a trifluoromethyl group or a hydrogen atom.
  • R 8a Is a C1-C6 haloalkyl group, -OR 22a (Where R 22a Is a C1-C6 haloalkyl group.
  • R 23a Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • -SF 5 Or a compound which is a halogen atom.
  • R 8a Is a C1-C6 haloalkyl group, -OR 22a (Where R 22a Is a C1-C6 haloalkyl group. ), -S (O) m R 23a (Where R 23a Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • R 8a Is a C1-C6 haloalkyl group, -OR 22a (Where R 22a Is a C1-C6 haloalkyl group. ), -S (O) m R 23a (Where R 23a Is a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
  • R 8a Is a C1-C6 haloalkyl group, -OR 22a (Where R 22a Is a C1-C6 haloalkyl group.
  • R 23a Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • R 8a Is a C1-C6 perfluoroalkyl group
  • -OR 22a Where R 22a Is a C1-C6 perfluoroalkyl group.
  • -S (O) m R 23a where R 23a Is a C1-C6 perfluoroalkyl group.
  • R 8a Is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • R 8a Is a trifluoromethyl group, -CF 2 CF 3 , -SCF 3 Or -S (O) 2 CF 3
  • a compound that is In formula (1-1) R 8a Is a trifluoromethyl group.
  • a 1a -NR 6a -And R 6a Has a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, or one or more halogen atoms.
  • a 1a -NR 6a -And R 6a Is a methyl group, ethyl group, propyl group, allyl group or propargyl group.
  • a 1a -NR 6a -And R 6a In which is a methyl group or a propargyl group.
  • R 1b In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 1b Is an ethyl group.
  • R 2b , R 4b And R 5b Are the same or different and are a halogen atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4b And R 5b Is a hydrogen atom and R 2b In which is a chlorine atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4b And R 5b Is a hydrogen atom and R 2b In which is a chlorine atom.
  • R 2b , R 4b And R 5b In which is a hydrogen atom.
  • R 3b Are methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -SCF 2 CF 3 , -S (O) 2 CF 3 , -S (O
  • R 3b Trifluoromethyl group, ethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -OCF 3 , 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
  • R 3b Trifluoromethyl group, ethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -OCF 3 , A 2-pyrimidinyl group, a fluorine atom, a bromine atom or a hydrogen atom.
  • R 3b In which is a trifluoromethyl group or a hydrogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF 5 Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group.
  • R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • -SF 5 A compound that is In formula (1-2), R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ) Or -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
  • R 8b Is a C1-C6 perfluoroalkyl group, -OR 22b (Where R 22b Is a C1-C6 perfluoroalkyl group. ) Or -S (O) m R 23b (Where R 23b Is a C1-C6 perfluoroalkyl group. ).
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -SCF 3 Or -S (O) 2 CF 3
  • R 1b In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 1b Is an ethyl group.
  • R 2b , R 4b And R 5b Are the same or different and are a halogen atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4b And R 5b Is a hydrogen atom and R 2b In which is a chlorine atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4b And R 5b Is a hydrogen atom and R 2b In which is a chlorine atom.
  • R 2b , R 4b And R 5b In which is a hydrogen atom.
  • R 3b Are methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -SCF 2 CF 3 , -S (O) 2 CF 3 , -S (O
  • R 3b Trifluoromethyl group, ethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -OCF 3 , 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
  • R 3b In which is a trifluoromethyl group, a chlorine atom or a hydrogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group.
  • R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • -SF 5 Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group.
  • R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • R 8b Is a C1-C6 perfluoroalkyl group
  • -OR 22b Where R 22b Is a C1-C6 perfluoroalkyl group.
  • -S (O) m R 23b where R 23b Is a C1-C6 perfluoroalkyl group.
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -SCF 3 Or -S (O) 2 CF 3 A compound that is In formula (1-3), R 8b Is a trifluoromethyl group, -CF 2 CF 3 Or -S (O) 2 CF 3 A compound that is In the formula (1-3), a compound wherein n is 2.
  • R 1b In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 1b Is an ethyl group.
  • R 2b , R 4b And R 5b Are the same or different and are a halogen atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4b And R 5b Is a hydrogen atom and R 2b In which is a chlorine atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom, a fluorine atom or a hydrogen atom.
  • R 2b , R 4b And R 5b Are the same or different and are a chlorine atom or a hydrogen atom.
  • R 4b And R 5b Is a hydrogen atom and R 2b In which is a chlorine atom.
  • R 2b , R 4b And R 5b In which is a hydrogen atom.
  • R 3b are methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, fluoromethyl, difluoromethyl, trifluoromethyl, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , A fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen
  • R 3b Trifluoromethyl group, ethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -OCF 3 , 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom.
  • R 3b Is a trifluoromethyl group.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group.
  • R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • -SF 5 Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group.
  • R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2.
  • R 8b Is a C1-C6 perfluoroalkyl group
  • -OR 22b Where R 22b Is a C1-C6 perfluoroalkyl group.
  • -S (O) m R 23b where R 23b Is a C1-C6 perfluoroalkyl group.
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -SCF 3 Or -S (O) 2 CF 3
  • R 1b In which is an ethyl group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 1b Is an ethyl group.
  • R 3b are methyl, fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, ethenyl, ethynyl, fluoromethyl, difluoromethyl, trifluoromethyl, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CF 2 CF 2 CF 2 CF 3 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , A fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. ), -SF 5 Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ), -S (O) m R 23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. Or a compound which is a halogen atom.
  • R 8b Is a C1-C6 haloalkyl group, -OR 22b (Where R 22b Is a C1-C6 haloalkyl group. ) Or -S (O) m R23b (Where R 23b Is a C1-C6 haloalkyl group and m is 0, 1 or 2. ).
  • R 8b Is a C1-C6 perfluoroalkyl group, -OR 22b (Where R 22b Is a C1-C6 perfluoroalkyl group. ) Or -S (O) m R 23b (Where R 23b Is a C1-C6 perfluoroalkyl group. ).
  • R 8b Is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S (O) CF 3 , -S (O) 2 CF 3 , -SCF 2 CF 3 , -S (O) CF 2 CF 3 , -S (O) 2 CF 2 CF 3 , SF 5 , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • R 60b Is a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group.
  • the compound of the present invention and the intermediate compound can be produced, for example, by the following (Production Method 1) to (Production Method 15).
  • This invention compound (1-n2) whose n is 2 in Formula (1) can be manufactured by oxidizing an intermediate compound (P1) with an oxidizing agent. [Wherein the symbols have the same meaning as in formula (1). ] The oxidation reaction is usually performed in the presence of a solvent.
  • the solvent examples include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
  • the oxidizing agent examples include m-chloroperbenzoic acid and hydrogen peroxide.
  • the reaction can be carried out in the presence of a catalyst as necessary.
  • the catalyst include sodium tungstate. In the reaction, when n is 0 in the intermediate compound (P1), the oxidant is usually 3 to 10 moles and the catalyst is usually 0.01 to 0. Used in a proportion of 5 moles.
  • the oxidizing agent is usually in a proportion of 2 to 10 mol and the catalyst is usually in a proportion of 0.01 to 0.5 mol with respect to 1 mol of the intermediate compound (P1). Used.
  • n is 2 in the intermediate compound (P1), the oxidizing agent is usually in a proportion of 1 to 10 mol and the catalyst is usually in a proportion of 0.01 to 0.5 mol with respect to 1 mol of the intermediate compound (P1). Used.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • the compound (1-n2) of the present invention can be isolated by performing post-treatment operations such as concentration.
  • the isolated present compound (1-n2) can be further purified by chromatography, recrystallization and the like.
  • the compound of the present invention in which n is 1 or 2 in formula (1) can be produced by oxidizing the compound of the present invention in which n is 0. [Wherein the symbols have the same meaning as in formula (1).
  • This invention compound (1-n1) whose n is 1 in Formula (1) can be manufactured by oxidizing this invention compound (1-n0) whose n is 0 with an oxidizing agent.
  • the oxidation reaction is usually performed in the presence of a solvent.
  • the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
  • the oxidizing agent include sodium periodate and m-chloroperbenzoic acid. In this reaction, an oxidizing agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the compound (1-n0) of the present invention.
  • the oxidizing agent is used in an amount of 1 to 1.2 mol per 1 mol of the compound (1-n0) of the present invention.
  • the reaction temperature is usually in the range of -20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried,
  • a reducing agent for example, sodium sulfite, sodium thiosulfate
  • a base for example, sodium bicarbonate
  • the isolated compound (1-n1) of the present invention can be further purified by chromatography, recrystallization and the like.
  • This invention compound (1-n2) whose n is 2 in Formula (1) can be manufactured by oxidizing this invention compound (1-n1) whose n is 1 with an oxidizing agent.
  • the oxidation reaction is usually performed in the presence of a solvent.
  • the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
  • the oxidizing agent include m-chloroperbenzoic acid and hydrogen peroxide.
  • the oxidizing agent is usually used at a ratio of 1 to 4 moles with respect to 1 mole of the compound (1-n1) of the present invention.
  • the oxidizing agent is used in a ratio of 1 to 2 moles relative to 1 mole of the compound (1-n1) of the present invention.
  • the reaction temperature is usually in the range of -20 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (1-n2) of the present invention can be isolated by performing post-treatment operations such as concentration.
  • the compound (1-n2) of the present invention can be further purified by chromatography, recrystallization and the like.
  • the compound (1-n2) of the present invention in which n is 2 in the formula (1) can be converted into a one-step reaction (one-pot) by oxidizing the compound (1-n0) of the present invention in which n is 0 with an oxidizing agent.
  • the oxidation reaction is usually performed in the presence of a solvent.
  • the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
  • the oxidizing agent include m-chloroperbenzoic acid and hydrogen peroxide.
  • the reaction can be carried out in the presence of a catalyst as necessary. Examples of the catalyst include sodium tungstate.
  • the oxidizing agent is usually used at a ratio of 2 to 5 moles, and the catalyst is usually used at a ratio of 0.01 to 0.5 moles.
  • the oxidizing agent is used in a ratio of 2 to 3 moles with respect to 1 mole of the compound (1-n0) of the present invention.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, and dried.
  • a reducing agent for example, sodium sulfite, sodium thiosulfate
  • a base for example, sodium bicarbonate
  • the compound (1-n0) of the present invention in which n is 0 in the formula (1) is produced by reacting the obtained intermediate compound (M6-N0) with the compound (M7) in the presence of a base.
  • V 2 represents a halogen atom, and the other symbols have the same meaning as in formula (1).
  • Intermediate compound (M6-N0) can be produced by oxidizing intermediate compound (M6).
  • the oxidation reaction is usually performed in the presence of a solvent.
  • the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
  • the oxidizing agent examples include m-chloroperbenzoic acid and hydrogen peroxide.
  • the reaction can be carried out in the presence of a catalyst as necessary.
  • the catalyst include sodium tungstate.
  • the reaction with respect to 1 mol of the intermediate compound (M6), the oxidizing agent is usually used in a proportion of 1 to 10 mol, and the catalyst is usually used in a proportion of 0.01 to 0.5 mol.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried,
  • a reducing agent for example, sodium sulfite, sodium thiosulfate
  • a base for example, sodium bicarbonate
  • the reaction is usually performed in the presence of a solvent.
  • a solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like.
  • Aprotic polar solvents water and mixtures thereof.
  • the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
  • the compound (M7) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M6-N0).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound (1-n0) of the present invention in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. it can.
  • the isolated compound of the present invention (1-n0) in which n is 0 can be further purified by chromatography, recrystallization and the like.
  • V 2 Is preferably a fluorine atom or a chlorine atom.
  • the intermediate compound (P1) is obtained by reacting the intermediate compound (M1) with the intermediate compound (M2) or the intermediate compound (M18) to produce the intermediate compound (M3). It can be produced by intramolecular condensation (cyclization) of (M3). [Wherein the symbols have the same meaning as in formula (1). ]
  • Intermediate compound (M3) can be produced by reacting intermediate compound (M1) and intermediate compound (M2) in the presence of a condensing agent. The reaction is usually performed in the presence of a solvent.
  • the solvent examples include 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as THF), ethers such as tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene.
  • ethers such as tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene.
  • Halogenated hydrocarbons such as toluene, benzene, xylene and the like, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, and N, N-dimethylformamide (hereinafter referred to as DMF).
  • NMP N-methylpyrrolidone
  • DMSO dimethyl sulfoxide
  • pyridine quinoline
  • DMSO dimethyl sulfoxide
  • the condensing agent include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as EDCI hydrochloride) and 1,3-dicyclohexylcarbodiimide.
  • EDCI hydrochloride 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • EDCI hydrochloride 1,3-dicyclohexylcarbodiimide
  • the catalyst examples include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).
  • HOBt 1-hydroxybenzotriazole
  • the intermediate compound (M1) is usually in a proportion of 0.5 to 2 mol
  • the condensing agent is usually in a proportion of 1 to 5 mol
  • the catalyst is usually in an amount of 0.8. It is used at a ratio of 01 to 1 mol.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (M3) can be isolated by collecting the resulting solid by filtration.
  • the isolated intermediate compound (M3) can be further purified by recrystallization, chromatography or the like.
  • the intermediate compound (M3) can be produced by reacting the intermediate compound (M1) with the intermediate compound (M18).
  • the reaction is usually performed in the presence of a solvent.
  • the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene.
  • Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
  • the reaction can be carried out by adding a base as necessary.
  • the base include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M1).
  • the reaction temperature is usually in the range of -20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (M3) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can.
  • the isolated intermediate compound (M3) can be further purified by chromatography, recrystallization and the like.
  • Intermediate compound (P1) can be produced by intramolecular condensation (cyclization) of intermediate compound (M3).
  • the reaction is usually performed in the presence of a solvent.
  • a solvent include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, toluene, and the like.
  • Aromatic hydrocarbons such as benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone and DMSO Examples thereof include polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
  • a condensing agent, an acid or a base can be used as necessary.
  • Examples of the condensing agent include EDCI hydrochloride, a mixture of triphenylphosphine and a base and carbon tetrachloride or carbon tetrabromide, and a mixture of azodiesters such as triphenylphosphine and diethyl azodicarboxylate.
  • Examples of the acid include sulfonic acids such as paratoluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
  • Examples of the base include pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU), and 1,5-diazabicyclo [4.3.
  • reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (P1) can be isolated by collecting the resulting solid by filtration.
  • the isolated intermediate compound (P1) can be further purified by recrystallization, chromatography or the like.
  • Intermediate compound (P1) can be produced in a one-step reaction (one pot) by reacting intermediate compound (M1) and intermediate compound (M2) in the presence of a condensing agent. The reaction is usually performed in the presence of a solvent.
  • the solvent examples include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, Aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone and DMSO Polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
  • ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether
  • halogenated hydrocarbons such as dichloromethane, chloroform
  • the condensing agent examples include carbodiimides such as EDCI hydrochloride and 1,3-dicyclohexylcarbodiimide.
  • the reaction can be carried out by adding a catalyst as necessary.
  • the catalyst include 1-hydroxybenzotriazole.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (P1) can be isolated by collecting the resulting solid by filtration.
  • the isolated intermediate compound (P1) can be further purified by recrystallization, chromatography or the like.
  • the intermediate compound (P1) can be produced in a one-step reaction (one pot) by reacting the intermediate compound (M1) with the intermediate compound (M18). The reaction is performed in the presence or absence of a solvent.
  • the solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane
  • aliphatic hydrocarbons such as hexane, heptane, and octane
  • aromatic hydrocarbons such as toluene and xylene.
  • Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures
  • the base examples include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M1).
  • the reaction temperature is usually in the range of 20 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (P1) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can.
  • the isolated intermediate compound (P1) can be further purified by chromatography, recrystallization and the like.
  • An intermediate compound (M14) is reacted with the intermediate compound (M2) or the intermediate compound (M18) to produce an intermediate compound (M14).
  • By reacting with 1 Intermediate compound (P1) in which is a sulfur atom (hereinafter referred to as intermediate compound (P20)) can be produced. [Wherein the symbols have the same meaning as in formula (1). ]
  • Intermediate compound (M14) can be produced by reacting intermediate compound (M9) with intermediate compound (M2).
  • the reaction is performed in the presence or absence of a solvent.
  • a solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene.
  • Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and nitrogen-containing aromatic compounds such as pyridine and quinoline And mixtures thereof.
  • the condensing agent include EDCI hydrochloride, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
  • the intermediate compound (M2) is usually used in a proportion of 1 to 3 mol and the condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the intermediate compound (M9).
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (M14) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can.
  • the isolated intermediate compound (M14) can be further purified by chromatography, recrystallization and the like.
  • the intermediate compound (M14) can be produced by reacting the intermediate compound (M9) with the intermediate compound (M18). The reaction is performed in the presence or absence of a solvent. A base can be added as necessary.
  • the solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatic hydrocarbons such as toluene and xylene.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane
  • aliphatic hydrocarbons such as hexane, heptane, and octane
  • aromatic hydrocarbons such as toluene and xylene.
  • Halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and nitrogen-
  • the base examples include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the intermediate compound (M9).
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (M14) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can.
  • the isolated intermediate compound (M14) can be further purified by chromatography, recrystallization and the like.
  • Intermediate compound (P20) can be produced by reacting intermediate compound (M14) with a sulfurizing agent. The reaction is performed in the presence or absence of a solvent.
  • the solvent examples include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, and diglyme, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene.
  • Aromatic hydrocarbons such as toluene, benzene and xylene, nitriles such as acetonitrile, nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine and quinoline, and mixtures thereof.
  • the sulfurizing agent examples include niline pentasulfide, Lawesson's reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide), and the like.
  • the sulfurizing agent is usually used in a ratio of 1 mol to 3 mol with respect to 1 mol of the intermediate compound (M14).
  • the reaction temperature is usually in the range of 0 ° C. to 200 ° C., and the reaction time is usually in the range of 1 to 24 hours.
  • reaction mixture After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (P20) can be isolated by collecting the resulting solid by filtration.
  • the isolated intermediate compound (P20) can be further purified by recrystallization, chromatography or the like.
  • Intermediate compound (P1) can be produced by reacting intermediate compound (M1) and intermediate compound (M4) in the presence of an oxidizing agent. [Wherein the symbols have the same meaning as in formula (1). ] The reaction is usually performed in the presence of a solvent.
  • solvent examples include alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether, THF and tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like.
  • Halogenated hydrocarbons aromatic hydrocarbons such as toluene, benzene, xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2-imidazolide
  • Non-protic polar solvents such as non-DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
  • the reaction can be carried out by adding an acid if necessary.
  • the acid include sulfonic acids such as paratoluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
  • the reaction can be carried out by adding sulfite as necessary.
  • the sulfites include sulfites such as sodium bisulfite and sodium disulfite.
  • the oxidizing agent include oxygen, copper (II) chloride, and DDQ.
  • the intermediate compound (M4) is usually in a proportion of 1 to 2 mol
  • the acid is usually in a proportion of 0.1 to 2 mol
  • the sulfite is usually in a proportion of 1 to 1 mol of the intermediate compound (M1).
  • the proportion of 5 moles and the oxidizing agent are usually used in a proportion of 1 to 5 moles.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • reaction mixture After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (P1) can be isolated by collecting the resulting solid by filtration.
  • the isolated intermediate compound (P1) can be further purified by recrystallization, chromatography or the like.
  • (Production method 7) Intermediate compound (P1-n0) can be produced by reacting intermediate compound (M6) with compound (M7) in the presence of a base. [Wherein V 2 Represents a halogen atom, and the other symbols have the same meaning as in formula (1). ] The reaction is usually performed in the presence of a solvent.
  • the solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like.
  • Aprotic polar solvents water and mixtures thereof.
  • the base examples include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
  • the compound (M7) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M6).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • an intermediate compound (P1-n0) in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. it can.
  • the isolated intermediate compound (P1-n0) in which n is 0 can be further purified by chromatography, recrystallization, and the like.
  • V 2 Is preferably a fluorine atom or a chlorine atom.
  • the intermediate compound (M20) is reacted with the intermediate compound (M19) or the intermediate compound (M39) to produce the intermediate compound (M20), and then the intramolecular mixture of the obtained intermediate compound (M20)
  • the intermediate compound (M6) can be produced by condensation (cyclization). [Wherein V 2 Represents a halogen atom, and the other symbols have the same meaning as in formula (1). ]
  • Intermediate compound (M20) can be produced according to the method of production method 4, using intermediate compound (M19) instead of intermediate compound (M2).
  • Intermediate compound (M20) can be produced according to the method of production method 4, using intermediate compound (M39) instead of intermediate compound (M18).
  • Intermediate compound (M6) can be produced according to the method of production method 4, using intermediate compound (M20) instead of intermediate compound (M3).
  • the intermediate compound (M6) can be produced in a one-step reaction (one pot) according to the production method 4 using the intermediate compound (M19) instead of the intermediate compound (M2).
  • the intermediate compound (M39) can be used in place of the intermediate compound (M2), and the intermediate compound (M6) can be produced in a one-step reaction (one pot) according to the production method 4.
  • V 2 Is preferably a fluorine atom or a chlorine atom.
  • Intermediate compound (M3) can be produced by reacting intermediate compound (M20) with compound (M7).
  • the intermediate compound (P1-n0) can be produced by intramolecular condensation (cyclization) of the obtained intermediate compound (M3).
  • V 2 represents a halogen atom, and the other symbols have the same meaning as in formula (1)
  • Intermediate compound (M3) in which n is 0 can be produced according to the method of production method 7, using intermediate compound (M20) instead of intermediate compound (M6).
  • Intermediate compound (P1-n0) can be produced according to the method of production method 4, using intermediate compound (M3) in which n is 0 instead of intermediate compound (M3).
  • the intermediate compound (M20) is used instead of the intermediate compound (M6), and the intermediate compound (P1-n0) in which n is 0 is reacted in a one-step reaction (one pot) according to the method of Production Method 7. It can also be manufactured.
  • V 2 Is preferably a fluorine atom or a chlorine atom.
  • R 6 ′ Is R in the formula (1) 6
  • L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and other symbols are represented by the formula (1) Represents the same meaning.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like.
  • the base examples include hydrides of alkali metals and alkaline earth metals such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine.
  • the compound (M10) is usually used in a proportion of 1 to 5 mol and the base is usually used in a proportion of 1 to 3 mol with respect to 1 mol of the intermediate compound (P2).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (P3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer.
  • the isolated intermediate compound (P3) can be further purified by chromatography, recrystallization and the like.
  • Intermediate compound (M30) can be nitrated, or intermediate compound (M33) can be reacted with compound (M28) to produce intermediate compound (M30).
  • intermediate compound (M30) By reducing the intermediate compound (M30) obtained here, A 1 -NR 6 An intermediate compound (M1) that is-can be produced. [Wherein the symbols have the same meaning as in formula (1). ]
  • Intermediate compound (M30) can be produced by reacting intermediate compound (M33) and compound (M28) in the presence of a base. The reaction is usually performed in the presence of a solvent.
  • the solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, NMP, DMSO, and the like.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • DMF dimethyl ether
  • NMP tert-butyl methyl ether
  • nitriles such as acetonitrile
  • DMSO dimethyl methyl ether
  • the reaction can be carried out by adding a base as necessary.
  • the base examples include alkali metal hydrides such as sodium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and pyridine, 4-dimethylaminopyridine. And nitrogen-containing aromatic compounds.
  • the compound (M28) is usually used in a proportion of 1 to 10 mol
  • the base is usually used in a proportion of 0 to 10 mol.
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
  • Intermediate compound (M30) can be produced by reacting intermediate compound (M29) with a nitrating agent.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
  • the nitrating agent include concentrated nitric acid.
  • the nitrating agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the intermediate compound (M29).
  • the reaction temperature is usually in the range of -10 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (M30) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. .
  • the isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
  • a 1 -NR 6 The intermediate compound (M1) which is-can be produced by reacting the intermediate compound (M30) with hydrogen in the presence of a hydrogenation catalyst.
  • the reaction is usually performed in a hydrogen atmosphere at 1 to 100 atmospheres, usually in the presence of a solvent.
  • a solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water, and mixtures thereof.
  • the hydrogenation catalyst include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
  • the reaction can be performed by adding an acid, a base or the like, if necessary.
  • the acid include acetic acid and hydrochloric acid
  • examples of the base include tertiary amines such as triethylamine, magnesium oxide and the like.
  • the reaction temperature is usually in the range of -20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction mixture is filtered, extracted with an organic solvent as necessary, and the organic layer is dried and concentrated to perform post-treatment operations such as A.
  • the intermediate compound (M30) is prepared by acetylating the intermediate compound (M29) to produce the intermediate compound (M29 ′), and then nitration of the obtained intermediate compound (M29 ′). It can also be produced by producing ') and hydrolyzing the obtained intermediate compound (M30'). [Wherein the symbols have the same meaning as in formula (1). ]
  • Intermediate compound (M29 ') can be produced by reacting intermediate compound (M29) with an acylating agent.
  • the reaction is usually performed in the presence of a solvent or using an acylating agent as a solvent.
  • the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene.
  • Nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, DMSO and mixtures thereof.
  • the acylating agent used in the reaction include acetic anhydride and paraacetoxynitrobenzene.
  • the reaction can be carried out by adding a base as necessary.
  • the base examples include tertiary amines such as triethylamine and N-ethyldiisopropylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the acetylating agent is usually used in a proportion of 1 mol or more and the base is usually used in a proportion of 0.1 to 10 mol with respect to 1 mol of the intermediate compound (M29).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the intermediate compound (M29 ') can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated intermediate compound (M29 ') can be further purified by chromatography, recrystallization and the like.
  • An intermediate compound (M30 ′) is produced by nitration of the intermediate compound (M29 ′) according to the production method 11 using the intermediate compound (M29 ′) instead of the intermediate compound (M29). be able to.
  • Intermediate compound (M30) can be produced by hydrolyzing intermediate compound (M30 ') in the presence of an acid or a base. When hydrolyzing with an acid, the reaction is usually carried out using an acid aqueous solution as a solvent.
  • the acid include mineral acids such as hydrochloric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and a mixture thereof.
  • the base examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and hydrazine.
  • the base is usually used at a ratio of 1 to 10 mol per 1 mol of the intermediate compound (M30 ′).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the intermediate solution (M30) is isolated by performing post-treatment operations such as acidification of the reaction solution, extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do.
  • the isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
  • Intermediate compound (M35) was produced by brominating the intermediate compound (M29), the resulting intermediate compound (M35) was aminated to produce A 1 -NR 6 An intermediate compound (M1) that is-can be produced. [Wherein the symbols have the same meaning as in formula (1). ]
  • Intermediate compound (M35) can be produced by reacting intermediate compound (M29) with a brominating agent. The reaction is usually performed in the presence of a solvent.
  • the solvent examples include water, acetic acid, ethers such as 1,4-dioxane, diethyl ether, and THF, esters such as ethyl acetate and butyl acetate, and halogens such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane. Hydrocarbons, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, DMSO and mixtures thereof.
  • the brominating agent include N-bromosuccinimide and bromine. The brominating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the intermediate compound (M29).
  • the reaction temperature is usually in the range of ⁇ 10 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (M35) can be isolated by collecting the resulting solid by filtration.
  • the isolated intermediate compound (M35) can be further purified by recrystallization, chromatography or the like.
  • a 1 -NR 7 The intermediate compound (M1) that is ⁇ can be produced by reacting the intermediate compound (M35) with an aminating agent in the presence of copper or a copper compound.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent include alcohols such as water, methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether and THF, esters such as ethyl acetate and butyl acetate, dichloromethane, chloroform, carbon tetrachloride, 1, Examples thereof include halogenated hydrocarbons such as 2-dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
  • Examples of the aminating agent include ammonia, aqueous ammonia and lithium amide.
  • Examples of the copper compound include copper iodide (I), copper oxide (I), copper oxide (II), acetylacetone copper (II), copper acetate (II), copper sulfate (II) and the like.
  • the reaction can be carried out by adding a ligand as necessary.
  • Examples of the ligand include acetylacetone, salen, and phenanthroline.
  • the reaction can be carried out by adding a base as necessary.
  • Examples of the base include pyridine, picoline, 2,6-lutidine, DBU, nitrogen-containing heterocyclic compounds such as 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N-ethyldiisopropylamine and the like.
  • Inorganic bases such as tertiary amines, tripotassium phosphate, potassium carbonate, cesium carbonate, sodium hydroxide and the like can be mentioned.
  • the aminating agent is usually used in a proportion of 1 to 5 mol, and copper or a copper compound is usually used in a proportion of 0.02 to 0.5 mol per 1 mol of the intermediate compound (M35).
  • the reaction temperature is usually in the range of 30 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture.
  • the intermediate compound (M1) which is-can be isolated.
  • Isolated A 1 -NR 7 The intermediate compound (M1) which is-can be further purified by recrystallization, chromatography or the like.
  • an intermediate compound (M34) is produced by reacting the intermediate compound (M33) with a sulfurizing agent, and then the obtained intermediate compound (M34) is reacted with a reducing agent.
  • a 1 Intermediate compound (M1) in which is a sulfur atom can be produced.
  • Intermediate compound (M34) can be produced by reacting intermediate compound (M33) with thiourea in the presence of a base. The reaction is usually performed in the presence of a solvent.
  • the solvent include alcohols such as methanol and ethanol, water, and a mixture thereof.
  • the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • thiourea is usually used in a proportion of 0.5 to 3 mol and a base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the intermediate compound (M33).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • an intermediate compound (M34) can be isolated by performing post-treatment operations such as addition of an acid to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. .
  • the isolated intermediate compound (M34) can also be purified by chromatography, recrystallization and the like.
  • the intermediate compound (M1) in which is a sulfur atom can be produced by reacting the intermediate compound (M34) with a reducing agent.
  • the reduction reaction can be performed, for example, in the presence of a reducing agent; an acid such as hydrochloric acid or acetic acid; and water.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, DMF, NMP, and DMSO.
  • aprotic polar solvents such as and mixtures thereof.
  • Examples of the reducing agent include metal powder such as iron powder and zinc powder, and tin dichloride.
  • metal powder or tin dichloride is usually used at a ratio of 3 to 10 mol with respect to 1 mol of the intermediate compound (M34).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • water is added to the reaction mixture, followed by extraction with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer.
  • the intermediate compound (M1) in which is a sulfur atom can be isolated. Isolated A 1
  • the intermediate compound (M1) in which is a sulfur atom can also be purified by chromatography, recrystallization and the like.
  • R 8 An intermediate compound (P7) in which is a C1-C6 perfluoroalkyl group is R 8 Can be produced by reacting the intermediate compound (P4) in which is a halogen atom with the compound (M11) or the compound (M11 ′) in the presence of copper or a copper compound.
  • Rf represents a C1-C6 perfluoroalkyl group, and other symbols have the same meanings as in formula (1).
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent include aromatic hydrocarbons such as toluene and xylene, aprotic polar solvents such as DMF, NMP, and DMSO, and mixtures thereof.
  • Examples of the copper compound include copper (I) iodide.
  • the compound (M11) is usually used in a proportion of 1 to 10 mol and the copper compound is usually used in a proportion of 0.5 to 10 mol with respect to 1 mol of the intermediate compound (P4). It is done.
  • the reaction temperature is usually in the range of 100 to 200 ° C.
  • the reaction time is usually in the range of 0.5 to 48 hours.
  • potassium fluoride may be added.
  • the compound (M11 ′) is usually in a proportion of 1 to 10 mol
  • copper or copper compound is usually in a proportion of 0.1 to 10 mol
  • potassium fluoride is usually in a proportion of 0.1 to 1 mol of the intermediate compound (P4). Used in a proportion of 5 moles.
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 48 hours.
  • the intermediate compound (P7) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer.
  • the isolated intermediate compound (P7) can be further purified by chromatography, recrystallization and the like.
  • V 1 As for, a bromine atom and an iodine atom are preferable.
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 ,
  • a 1 And n is a combination of the compounds described in [Table 1] to [Table 14].
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents an n-propyl group
  • iPr represents an isopropyl group
  • tBu represents a tert-butyl group.
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a pentafluoroethyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a heptafluoroisopropyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethoxy group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfanyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfinyl group and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 , And n are the combinations described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a trifluoromethylsulfonyl group, R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And compounds in which n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 , And n are the combinations described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 , And n are the combinations described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is a bromine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 Is an iodine atom and R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 , R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a fluorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a fluorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a fluorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a fluorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a chlorine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a chlorine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a chlorine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a chlorine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a bromine atom and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a bromine atom and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a bromine atom and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a bromine atom and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a methyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a methyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a methyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a methyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is an ethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is an ethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is an ethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is an ethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 2 Is a trifluoromethyl group and R 3 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 4 Is a trifluoromethyl group and R 2 , R 3 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 5 Is a trifluoromethyl group and R 2 , R 3 , R 4 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a pentafluoroethyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a heptafluoropropyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a trifluoromethoxy group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 3-chloro-2-pyridyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 Is a 2-pyrimidinyl group and R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • R 3 -SF 5 And R 2 , R 4 , R 5 , R 7 And R 9 Is a hydrogen atom and R 8 -SF 5 And R 1 , A 1 And n is a combination described in [Table 1] to [Table 14].
  • pests for which the compounds of the present invention are effective include harmful arthropods and nematodes such as harmful insects and harmful mites. Specific examples of such pests include the following.
  • Hemiptera small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper such as leafhoppers (Empoascaonukii) Cotton aphids (Aphis gossypii), peach aphids (Myus persicae), radish aphids (Brevicorine brassicae), aphis spiraecola, tulip beetle aphids ( Acrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat leaf aphids (Rhopalosiphum padi), citrus aphids (Toxoptera cit
  • Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorisa chinensis), bark beetle (Eysarcoris parvus), winged beetle (Halyomorpha mista)
  • Whitefly species such as svaporiarum, Tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), Alecananthus spiniferus (Aleurocanthus sphinferus), citri), Ruby Roe beetle (Ceroplastes rubens), Iceria scale insect (Icerya purchasi), Fujino scale insect (Pranococcus kraunhiae), Swan scale scale (Pseudococcus longis) is), scale insects such as Pseudauracapaspis pentagona, bed bugs, bed bugs such as bed bugs (Cimex electrarius), and whales.
  • Lepidopterous pests Chilo suppressalis, Sankaiga ( Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Pyralidae such as Shibatsutoga (Pediasia teterrellus), common cutworm ( Spodoptera litura, Spodoptera exigua, Ayuyoto (Pseudaletia separata), Miostra brassicae, Amantisipsilon , Tamanagin'uwaba (Plusia nigrisigna), Trichoplusia spp., Heliothis spp., Noctuidae such Helicoverpa spp such as white butterfly such as cabbage butterfly (Pieris rapae), Adokisofiesu
  • Sugas such as Plutella xylostella
  • cotton moths such as Pectinophora gossypiella potato (Phthromeaea perculella)
  • white-spotted tigers Hirokosukoga such as Koiga (Tineola bisselliella).
  • Diptera Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc.
  • Pterodoptera Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Red-bellied lion (Oxya yezoensis), Lobster (Oxya japonica), and crickets.
  • Lepidoptera Cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mud mines (Xenopsylla cheopeis) and the like.
  • Anoplura body louse (Pediculus humanus corporis), head lice (Pediculus humanus humanus), crab louse (Phthirus pubis), Ushijirami (Haematopinus eurysternus), Hitsujijirami (Dalmalinia ovis), Butajirami (Haematopinus suis), Inujirami (Linognathus setosus) and the like.
  • White-eye pests sheep lice (Dalmalinia ovis), cattle lice (Dalmalinia bovis), chicken lice (Menopon gallinae), dog lice (Trichodictes canis), cat lice, etc.
  • Hymenoptera Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Ants such as Argentine ants (Linepithema humile), wasps such as wasps, scallops, and wasps such as wasp (Athalia rosae) and Japanese bee (Athalia japonica).
  • Nematodes rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematode (Globodera rostochiensis), southern nematode crested pea (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus).
  • Cockroach pests German cockroach (Blatella germanica), Black cockroach (Periplaneta fuliginosa), Cockroach cockroach (Periplaneta americana), Periplaneta brunat (Brunetella brunet)
  • Termite pests Yamato termites (Reticulitermes pertus), termites (Coptothermes formosanus), American termites minor (Incitermites minor), Dikokite termites (Crypt) otermes domesticus), Taiwan termites (Odontotermes formosanus), Kou Shun termite (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Katan termites (Glyptotermes fuscus), Kodama termites (Glyptotermes kodamai), comb Moto termites ( Glypoptermes kushimensis, White termites (
  • Mite order pests Tick spider mites (Tetranychus urticae), Tick spider mites (Tetranychus kanzawai), citrus spider mite (Pananychus citri), mite spider mite (Panthonychus ulmi), prickly mite pistols, citrus urticae Tomato rust mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple rust ticles ndali) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (
  • Lip and leg class Geuji (Thereuonema hilgendorfi), Tobizukade (Scoopendra subspinepes), etc. Double leg class: Yakuyasu (Oxidus gracilis), Akadesde (Nedyopus tambanus), etc. Isopods: Armadillium vulgare, etc. Gastropoda: Limax marginatus, Limax flavus, etc.
  • the pest control agent of the present invention contains the compound of the present invention and an inert carrier.
  • the pest control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and a surfactant or other formulation adjuvant is added as necessary.
  • an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc.
  • a surfactant or other formulation adjuvant is added as necessary.
  • These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
  • the pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
  • solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur).
  • Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
  • liquid carriers examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons.
  • alcohols methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.
  • ketones acetone, methyl ethyl ketone, cyclohexanone, etc.
  • aromatic hydrocarbons examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.
  • ketones acetone, methyl ethyl ket
  • Acid amides N, N-dimethylformamide, N, N-dimethylacetamide, etc.
  • halogenated hydrocarbons diichloromethane, trichloroethane, carbon tetrachloride, etc.
  • sulfoxides dimethylsulfoxide, etc.
  • propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).
  • gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • formulation adjuvants include sticking agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • sticking agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (iso
  • the base material of the resin preparation examples include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added.
  • the resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string.
  • These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
  • the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid.
  • antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid
  • preservatives such as dehydroacetic acid.
  • Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.
  • the pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.).
  • the pest control method of the present invention is usually used in the form of the pest control agent of the present invention.
  • the application rate is 10,000 m. 2
  • the amount of the compound of the present invention is usually 1 to 10,000 g.
  • the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10000 ppm. Agents, powders, etc. are usually applied as they are. These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit cultivated soil.
  • the application amount is 1 m when treated on the surface. 2
  • the amount of the compound of the present invention per unit is usually 0.01 to 1000 mg.
  • the processing space is 1 m. 3
  • the amount of the present compound per unit is usually 0.01 to 500 mg.
  • the pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm.
  • the harmful arthropod control agent of the present invention is used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals.
  • systemic suppression for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression.
  • an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag.
  • the amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.
  • the pest control agent of the present invention can be used in farmland where the following “crop” is cultivated. Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
  • Vegetables Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American boofish, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
  • Fruit trees apples, pears, Japanese pears, quince, quince, etc., nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (citrus mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
  • Trees other than fruit trees tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
  • Lawn Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, blue whale, etc.
  • Crop includes genetically modified crops.
  • the pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are shown below.
  • Active ingredient of insecticide (1) Organophosphorus compounds Acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyphos, chlorfenvinphos, chlorpyriphos , Cyanophos (CYAP), diazinon, DCIP (dichroodiisopropyl ether), diclofenthion (ECP), dichlorvos (DDVP), dimethoate (dimeth) ate), dimethylvinphos, disulfoton, EPN, ethion, ethophos, etrimfos, fenthion (MPP), fenitrothion (m) , Formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion, TP nocrotophos, nared (BRP), oxydeprofos (ESP), parathion, fosarone, pho
  • Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, and bisultap.
  • Neonicotinoid compounds Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothidin and clothidin.
  • Phenylpyrazole compound Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
  • Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
  • Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
  • Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.
  • R 1000 Represents chlorine, bromine or iodine.
  • a compound represented by Active ingredient of acaricide Acequinosyl, amitraz, benzoximate, bifenaate, phenisobromolate, chinomethionate, BS chlorbenzylate, chlorbenzylate (Clofenetine), cyflumethofen (cyflumetofen), kelsen (dicofol: dicofol), etoxazole (etoxazole), fenbutatin oxide (fenbutatincarb), fenothiocarb (fenothiocarb), fenpyroximate x ), Fluacrylpyrim (fluproxyfen), hexythiazox, propargite (BPPS), polynactin complex (polynatide), pyridabene (pyridenephen) tetradifon, spirodi
  • Active ingredient of nematicide DCIP fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imicyafos.
  • Active ingredient of fungicide Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Dibuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole (triflumizole) raconazole, microbutanil, fenbuconazole, hexacon
  • Organic phosphorus herbicidal compound Amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glucosinate Vialaphos.
  • Carbamate herbicidal compounds Di-allate, tri-allate, EPTC, butyrate, bentiocarb, esprocarb, molinate, dimepiperate, swep (Chlorpropham), phenmedifam, phenisopham, pyributicalb, and ashlam.
  • Acid amide herbicidal compound Propanil, propyzamide, bromobutide, and etobenzanide.
  • Chloroacetanilide herbicidal compound Acetochlor, alachlor, butachlor, dimethenamide, dipachenol, metazachlor, metolachlor, retilachlor, retilachlor And petoxamide.
  • Diphenyl ether herbicidal compound Acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxynil, and acloniphen.
  • Cyclic imide herbicidal compound Oxadiazone, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, flurochlorac-pentyl, flumioxazine (flumifluaflufen) Ethyl (pyraflufen-ethyl), oxadialgyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfenazone, benzfendizone, benzfendizone Le (saflufenacil).
  • Trione oxime herbicidal compound Alloxydim-sodium, cetoxydim, butroxydim, clesodim, cloproxidim, cyclohexyloxym, teproloxydim ).
  • Seperex Piperonyl butoxide
  • sesamex sesamex
  • sulfoxide N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide
  • N-Decriimidazole N-decylimidazole
  • WARF-anti-resistant TBPT
  • the part in a formulation example represents a weight part.
  • Formulation Example 1 10 parts of any one of the compounds 1 to 28 of the present invention are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate And mix to obtain each emulsion.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of the compounds 1 to 28 of the present invention are added and mixed. Get a wettable powder.
  • Formulation Example 3 1 part of the synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed with 2 parts of any one of the compounds 1 to 28 of the present invention. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
  • Formulation Example 4 1 part of any one of the compounds 1 to 28 of the present invention is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of PAP and 93.7 parts of fubasami clay are added to this, and the mixture is thoroughly stirred and mixed.
  • Formulation Example 5 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of any one of the compounds 1 to 28 of the present invention, and 55 parts of water are mixed and wet pulverized. Each flowable agent is obtained by finely pulverizing with.
  • Formulation Example 6 0.1 part of any one of the compounds 1 to 28 of the present invention is dissolved in 5 parts of xylene and 5 parts of trichloroethane and mixed with 89.9 parts of deodorized kerosene to obtain each oil agent.
  • Formulation Example 7 10 mg of any one of the compounds 1 to 28 of the present invention is dissolved in 0.5 ml of acetone, and this solution is treated with 5 g of animal solid feed powder (solid feed powder CE-2 for breeding breeding, Nippon Claire Co., Ltd.). And mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.
  • Formulation Example 8 0.1 part of any one of the compounds 1 to 28 of the present invention, 49.9 parts of neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled and shaken. Finally, an oil aerosol is obtained by mounting the actuator.
  • Formulation Example 10 0.1 g of any one of the compounds 1 to 28 of the present invention is dissolved in 2 ml of propylene glycol and impregnated into a porous ceramic plate having a size of 4.0 ⁇ 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke. .
  • Formulation Example 11 Any 5 parts of the present compounds 1-28 and 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT WD301, manufactured by Sumitomo Chemical Co., Ltd.) are hermetically sealed.
  • a kneader (manufactured by Moriyama Seisakusho) is melt-kneaded, and the obtained kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
  • Formulation Example 12 5 parts of any of the compounds 1 to 28 of the present invention and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die.
  • a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm is obtained.
  • Formulation Example 13 100 mg of any of the present compounds 1-28, lactose 68.75 mg, corn starch 237.5 mg, microcrystalline cellulose 43.75 mg, polyvinylpyrrolidone 18.75 mg, sodium carboxymethyl starch 28.75 mg, and magnesium stearate 2. 5 mg is mixed and the resulting mixture is compressed to an appropriate size to obtain tablets.
  • Formulation Example 14 25 mg of any of the present compounds 1-28, lactose 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is filled into a hard shell gelatin capsule or hydroxypropylmethylcellulose capsule And a capsule is obtained.
  • Formulation Example 15 Any one of the present compounds 1-28, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, Veegum K (Vanderbilt Co.) 100 mg, flavor 35 mg, and coloring Distilled water is added to 500 mg of the preparation so that the final volume is 100 ml, and mixed to obtain a suspension for oral administration.
  • Formulation Example 16 Any 5 parts of the compounds 1 to 28 of the present invention are dissolved in 5 parts of polysorbate 85, 3 parts of benzyl alcohol and 30 parts of propylene glycol, and phosphoric acid is added so that the pH of this solution is 6.0 to 6.5.
  • Formulation Example 17 5 parts of aluminum distearate is dispersed by heating in 57 parts of fractionated coconut oil and 3 parts of polysorbate 85. 25 parts of saccharin is dispersed in an oily vehicle obtained by cooling this to room temperature. To this, 10 parts of any one of the compounds 1 to 28 of the present invention are added to obtain a paste preparation for oral administration.
  • Formulation Example 18 Any 5 parts of the compounds 1 to 28 of the present invention are mixed with 95 parts of limestone powder, and granules for oral administration are obtained using a wet granulation method.
  • Formulation Example 19 Any 5 parts of the present compounds 1 to 28 are dissolved in 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is mixed therewith to obtain a spot-on solution.
  • Formulation Example 20 Any 10 parts of the compounds 1 to 28 of the present invention are dissolved in 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed therewith to obtain a pour-on solution.
  • Formulation Example 21 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol are added to 0.5 parts of any of the present compounds 1 to 28, and sufficient until a uniform solution is obtained. After stirring and mixing, 19.5 parts of water is added and further stirred and mixed to obtain a shampoo agent of a uniform solution.
  • Formulation Example 22 0.15 parts of any of the compounds 1 to 28 of the present invention, 95 parts of animal feed, and 4.85 parts of a mixture comprising dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) are sufficiently stirred and mixed. Get a feed premix.
  • Formulation Example 23 7.2 g of any of the present compounds 1 to 28 and 92.8 g of Phosco S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C., poured into a suppository form, cooled and solidified, and suppository. Get. Next, the pest control effect of the compound of the present invention is shown by test examples.
  • Test example 1 Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. On the other hand, about 30 cotton aphids were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups and left for 1 day.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the characters in the formula have the following meanings.
  • Formulation Example 5 it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group. As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 1 to 3 of the present invention.
  • Test example 2 Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Formulation Example 5 it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group. As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 1 to 3 of the present invention.
  • Test example 3 The preparation of Compound 3 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the characters in the formula have the following meanings.
  • Formulation Example 5 it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group. As a result, a control value of 90% or more was shown in the treatment section using the test chemical solution of the present compound 3.
  • Test example 4 Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the characters in the formula have the following meanings.
  • Formulation Example 5 it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group. As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 1 to 3 of the present invention.
  • Test Example 5 Formulations 2 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Formulation Example 5 it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group. As a result, a control value of 90% or more was shown in the treatment section using the test chemical solutions of the compounds 2 to 3 of the present invention.
  • Test Example 6 Formulations 2 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Test Example 7 Formulations 1 to 3 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration would be 500 ppm to prepare a test spray solution.
  • apples were planted in plastic cups and grown until the seventh and eighth true leaves developed. The apple was sprayed with the test chemical at a rate of 20 mL / cup. After the chemical solution was dried, 60 first-instar larvae of apple cockerel were released, the bottom was hollowed out, and the plastic cup with filter paper was placed upside down. Seven days later, the number of surviving insects was counted, and the death rate was calculated from the following formula.
  • Test Example 9 Each formulation of the compound of the present invention obtained in Formulation Example 5 is diluted with water so that the active ingredient concentration is 500 ppm to prepare a test drug solution. A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as food. Two adult male German cockroaches (Blattala germanica) are released into the polyethylene cup and covered.
  • Test Example 10 The preparation of Compound 2 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. 0.7 ml of the test chemical solution was added to 100 ml of ion-exchanged water (active ingredient concentration 3.5 ppm). Twenty dead larvae of Culex pipiens parallels were released into the liquid, and the viability was investigated one day later to determine the mortality rate. As a result, the treatment with Compound 2 of the present invention showed a mortality rate of 91% or more.
  • the compound of the present invention has a control effect against pests and is useful as an active ingredient of a pest control agent.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
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  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Veterinary Medicine (AREA)
  • Agronomy & Crop Science (AREA)
  • Public Health (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un composé hétérocyclique fusionné représenté par la formule (1) qui a une excellente efficacité dans la lutte contre les nuisibles, et qui est utile en tant qu'ingrédient actif dans des agents de lutte contre les nuisibles. Dans la formule, A1 représente -NR6-, un atome d'oxygène ou un atome de soufre, R1 représente un groupe hydrocarboné à chaîne C1-C6, etc., R2, R3, R4, et R5 sont identiques ou différents et représentent un groupe hydrocarboné à chaîne C1-C6, etc., éventuellement possédant un ou plusieurs atome d'halogène, R6 représente un groupe hydrocarboné à chaîne C1-C6, etc., R7 et R8 sont identiques ou différents et représentent un groupe hydrocarboné à chaîne C1-C6, etc., et n représente 0, 1 ou 2.
PCT/JP2013/066768 2012-06-21 2013-06-12 Composé hétérocyclique fusionné WO2013191189A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014132971A1 (fr) * 2013-02-28 2014-09-04 住友化学株式会社 Composé hétérocyclique condensé et applications de lutte antiparasitaire correspondantes
WO2014132972A1 (fr) * 2013-02-28 2014-09-04 住友化学株式会社 Composé hétérocyclique à cycles condensés et ses applications dans la lutte contre les organismes nuisibles
WO2016002594A1 (fr) * 2014-07-04 2016-01-07 住友化学株式会社 Composition pesticide et son application
KR20170117079A (ko) 2015-02-12 2017-10-20 닛산 가가쿠 고교 가부시키 가이샤 축합 복소 고리 화합물 및 유해 생물 방제제
KR20180116303A (ko) 2016-03-10 2018-10-24 닛산 가가쿠 가부시키가이샤 축합 복소 고리 화합물 및 유해 생물 방제제

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GB1445824A (en) * 1973-02-03 1976-08-11 Thomae Gmbh Dr K Imidazo-4,5-b pyridines
JP2008308448A (ja) * 2007-06-15 2008-12-25 Sankyo Agro Kk （３−硫黄原子置換フェニル）へテロアリール誘導体
WO2012086848A1 (fr) * 2010-12-24 2012-06-28 Sumitomo Chemical Company, Limited Composé hétérocyclique fusionné et son utilisation pour la lutte contre les ravageurs

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
GB1445824A (en) * 1973-02-03 1976-08-11 Thomae Gmbh Dr K Imidazo-4,5-b pyridines
JP2008308448A (ja) * 2007-06-15 2008-12-25 Sankyo Agro Kk （３−硫黄原子置換フェニル）へテロアリール誘導体
WO2012086848A1 (fr) * 2010-12-24 2012-06-28 Sumitomo Chemical Company, Limited Composé hétérocyclique fusionné et son utilisation pour la lutte contre les ravageurs

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014132971A1 (fr) * 2013-02-28 2014-09-04 住友化学株式会社 Composé hétérocyclique condensé et applications de lutte antiparasitaire correspondantes
WO2014132972A1 (fr) * 2013-02-28 2014-09-04 住友化学株式会社 Composé hétérocyclique à cycles condensés et ses applications dans la lutte contre les organismes nuisibles
CN105164109A (zh) * 2013-02-28 2015-12-16 住友化学株式会社 稠合杂环化合物和其有害生物防除用途
US9573963B2 (en) 2013-02-28 2017-02-21 Sumitomo Chemical Company, Limited Fused heterocyclic compound and pest control applications thereof
WO2016002594A1 (fr) * 2014-07-04 2016-01-07 住友化学株式会社 Composition pesticide et son application
KR20170117079A (ko) 2015-02-12 2017-10-20 닛산 가가쿠 고교 가부시키 가이샤 축합 복소 고리 화합물 및 유해 생물 방제제
US10464950B2 (en) 2015-02-12 2019-11-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10882869B2 (en) 2015-02-12 2021-01-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
KR20180116303A (ko) 2016-03-10 2018-10-24 닛산 가가쿠 가부시키가이샤 축합 복소 고리 화합물 및 유해 생물 방제제
US10544163B2 (en) 2016-03-10 2020-01-28 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10640518B2 (en) 2016-03-10 2020-05-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10759815B2 (en) 2016-03-10 2020-09-01 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides

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