WO2012050141A1 - Heteroaromatic ring compound and use thereof for pest control - Google Patents

Heteroaromatic ring compound and use thereof for pest control Download PDF

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Publication number
WO2012050141A1
WO2012050141A1 PCT/JP2011/073451 JP2011073451W WO2012050141A1 WO 2012050141 A1 WO2012050141 A1 WO 2012050141A1 JP 2011073451 W JP2011073451 W JP 2011073451W WO 2012050141 A1 WO2012050141 A1 WO 2012050141A1
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group
atom
formula
heteroaromatic ring
compound
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PCT/JP2011/073451
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French (fr)
Japanese (ja)
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舞衣 伊藤
池上　宏
吉彦 野倉
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住友化学株式会社
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Publication of WO2012050141A1 publication Critical patent/WO2012050141A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to a heteroaromatic ring compound and its use for pest control.
  • a compound having a pest control activity has been found and developed as an active ingredient of a pest control agent.
  • Non-Patent Document 1 describes a compound having a thiophene ring and a pyridine ring in the molecule.
  • An object of the present invention is to provide a novel compound having a controlling activity against pests.
  • Het represents a 5- or 6-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (wherein A and Q are the 5- or 6-membered members, respectively)
  • a and Q are the 5- or 6-membered members, respectively
  • the atom bonded to the carbon atom or nitrogen atom constituting the heteroaromatic ring, and the atom bonded to A and the atom bonded to Q are not adjacent to each other on the 5- or 6-membered heteroaromatic ring.
  • the 6-membered heteroaromatic ring has 3 or 4 atoms selected from the group consisting of —CE 1 ⁇ , —N ⁇ , —O—, —S— and —NE 2 — together with atoms to which A and Q are bonded.
  • E 1 represents a C1-C2 alkyl group which may have one or more halogen atoms, a hydrogen atom or a halogen atom
  • E 2 has one or more halogen atoms.
  • J is the following formula J1 or J2:
  • R 1 and R 2 are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms
  • R 3 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom
  • R 4 and R 5 are the same or different and represent a C1-C3 alkyl group
  • R 6 represents a hydrogen atom or a C1-C6 chain hydrocarbon group.
  • Represents a group represented by L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms
  • A represents a single bond, —O—, or —S (O) x — when A is bonded to the carbon atom constituting the 5- or 6-membered heteroaromatic ring represented by Het (here, X represents 0, 1 or 2.), when A is bonded to the nitrogen atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, it represents a single bond;
  • Q is bonded to a carbon atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, the following formula Q1, Q2, Q3 or Q4:
  • R x and R y are the same or different and each may have one or more atoms or groups selected from ⁇ Group ⁇ >, C1-C6 chain hydrocarbon group, cyano group, halogen atom, hydrogen atom Or a cyclopropyl group, y represents 0, 1 or 2;
  • R z is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, —C (O) —T 1 , —S (O) 2 —.
  • T 2 represents a hydrogen atom or a cyclopropyl group
  • T 1 has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms.
  • T 2 represents a C1-C6 alkyl group which may have one or more halogen atoms.
  • G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or the following formulas G1, G2, G3 or G4:
  • R a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T 1 which may have one or more atoms or groups selected from ⁇ Group ⁇ >
  • R b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, —C (O) —T 1 , —S (O) 2 —.
  • T 2 represents a C3-C9 trialkylsilyl group or a cyclopropyl group
  • R c represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from ⁇ Group ⁇ >, —C (O) —T 1 or a cyclopropyl group
  • z represents 0, 1 or 2
  • R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, —C (O) —T 1 , —S (O) 2 —.
  • T 2 or a cyclopropyl group R e represents a C1-C6 chain hydrocarbon group, a hydrogen atom or a cyclopropyl group which may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • T 1 and T 2 are as defined above, but when G is a group represented by the formula G2, G3 or G4, T 1 may have one or more halogen atoms.
  • ⁇ D represents —N ⁇ or —CH ⁇ , m represents 0 or 1;
  • [Claim 10] The heteroaromatic ring compound according to [Claim 9], wherein Y 1 is -S-, Y 2 and Y 3 are the same or different, and -CE 1 .
  • Het is a 5- or 6-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom (wherein A and Q are each 5 or An atom to which A is bonded and an atom to which Q is bonded are not adjacent to each other on the 5- or 6-membered heteroaromatic ring, bonded to a carbon atom or a nitrogen atom constituting the 6-membered heteroaromatic ring.
  • the 5- or 6-membered heteroaromatic ring is composed of 3 or 4 atoms or groups selected from the group consisting of —CE 1 ⁇ , —N ⁇ and —S— together with atoms to which A and Q are bonded.
  • J is the formula J1 or J2 (R 1 and R 2 are the same or different and are a C1-C3 alkyl group, R 3 is a C1-C6 chain hydrocarbon group, and R 4 and R 5 are The same or different, a C1-C3 alkyl group, and R 6 is a C1-C6 chain hydrocarbon group).
  • L is a single bond or a C1-C3 alkylene group
  • A is a single bond
  • Q is a group represented by the formula Q1 (R x and R y are hydrogen atoms)
  • G is a hydrogen atom, a halogen atom, or a formula G1, G2, G3 or G4 ⁇ R a is a C1-C6 chain hydrocarbon group
  • R b is a C1-C6 chain hydrocarbon group
  • R c is a C1-C6 chain hydrocarbon group
  • z is 0, 1 or 2
  • R d is a C1-C6 chain hydrocarbon group
  • R e is a C1-C6 chain hydrocarbon group. It is a hydrogen group.
  • Het is a 5-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom (wherein A and Q are each a 5-membered heteroaromatic ring). An atom bonded to carbon atom or nitrogen atom constituting an aromatic ring, and an atom bonded to A and an atom bonded to Q are not adjacent to each other on the 5-membered heteroaromatic ring.
  • Is composed of three atoms or groups selected from the group consisting of —CE 1 ⁇ , —N ⁇ and —S— together with atoms to which A and Q are bonded, and E 1 has one or more halogen atoms.
  • J is a group represented by the formula J1 (wherein R 1 and R 2 are the same or different and are a C1-C3 alkyl group and R 3 is a C1-C6 chain hydrocarbon group); L is a single bond or a C1-C3 alkylene group, A is a single bond, Q is a group represented by the formula Q1 (R x and R y are hydrogen atoms), G is a hydrogen atom, a halogen atom, or a formula G2 or G3 ⁇ R b is a C1-C6 chain hydrocarbon group, R c is a C1-C6 chain hydrocarbon group, and z is 0 is there.
  • a pest control agent comprising the heteroaromatic ring compound according to any one of [Item 1] to [Item 18] and an inert carrier.
  • a method for controlling pests comprising a step of applying an effective amount of the heteroaromatic ring compound according to any one of items [1] to [18] to a pest or a habitat of the pest.
  • the compound of the present invention is useful for controlling pests.
  • halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” represented by E 1 include a methyl group, an ethyl group, a trifluoromethyl group, and a difluoromethyl group.
  • examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” represented by E 2 include a methyl group, an ethyl group, and 2,2,2-trifluoroethyl. Group, and a 2,2-difluoroethyl group.
  • examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • examples of the “C1-C3 alkyl group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a trifluoromethyl group.
  • Examples of the “C1-C6 alkyl group optionally having one or more halogen atoms” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a sec-butyl group. , Tert-butyl group, pentyl group, hexyl group and trifluoromethyl group.
  • examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 2 , C1-C6 alkyl groups such as 2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group and hexyl group; Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group C2-C6 alkenyl group such as ethynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butyn
  • Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, sec 1 such as -butyl group, tert-butyl group, pentyl group, 2,2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group hexyl group and trifluoromethyl group
  • a C1-C6 alkyl group optionally having one or more halogen atoms
  • examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from ⁇ group ⁇ >” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • ⁇ Group ⁇ > such as butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl and cyclopropylmethyl
  • a C1-C6 alkyl group optionally having one or more atoms or groups
  • a C2-C6 alkenyl group optionally having one or more atoms or groups selected from ⁇ Group ⁇ > such as 2-propenyl group
  • ⁇ Group ⁇ > such as propargyl group and 2-butynyl group
  • Examples include C2-C6 alkynyl group which may have one or more atoms or groups.
  • examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from ⁇ group ⁇ >” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • a C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group, tert-butyl group; C1- having one or more atoms or groups selected from ⁇ Group ⁇ > such as trifluoromethyl group, cyanomethyl group, cyclopropylmethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group and methylthiomethyl group
  • ⁇ Group ⁇ > such as vinyl group, isopropenyl group, 1-propenyl group, 2-methyl-1-propenyl group, 2,2-dichlorovinyl group and 2,2-difluorovinyl group Or a C2-C6 alkenyl group which may have a group; and ⁇ Group ⁇ > such as an ethynyl group, a 1-propynyl group, a 2-chloroethynyl group, a 2-fluoro
  • examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from ⁇ group ⁇ >” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • a C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group and tert-butyl group; Difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,1-trifluoro-2-propyl group, cyanomethyl group 1-cyanoethyl group, cyclopropylmethyl group, 1- (cyclopropyl) ethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, methylthiomethyl group, methylsulfinylmethyl group, methyl Sulfonylmethyl group, 2- (methylthio) ethyl group, 2- (methylsulfinyl) ethyl group, 2- (methylsulfonyl) ethyl group, 2- (
  • C1-C6 alkyl group having one or more atoms or groups selected from ⁇ group gamma>;
  • a C3-C6 alkenyl group optionally having one or more atoms or groups selected from ⁇ Group ⁇ > such as a 2-propenyl group, a 2-butenyl group and a 3-methyl-2-butenyl group; and a propargyl group
  • a C2-C6 alkynyl group which may have one or more atoms or groups selected from ⁇ Group ⁇ > such as 2-butynyl group and 3-butynyl group.
  • Examples of the “C1-C3 alkylene group optionally having one or more halogen atoms” in the compounds of the present invention include —CH 2 —, —CHCl—, —CHF—, —CF 2 —, —CH 2 CH 2 -and -CH 2 CH 2 CH 2 -are mentioned.
  • C3-C9 trialkylsilyl group means a trialkylsilyl group having 3 to 9 carbon atoms in the alkyl portion, and each alkyl group may be the same or different. Examples thereof include a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, and a triisopropylsilyl group.
  • Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group.
  • examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” include, for example, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutyl
  • An amino group, a sec-butylamino group, a tert-butylamino group and a 2,2,2-trifluoroethylamino group can be mentioned.
  • the “C2-C12 dialkylamino group optionally having one or more halogen atoms” has one or more halogen atoms having 2 to 12 carbon atoms in the alkyl part.
  • Each alkyl group may be the same or different, for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N— Dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methylamino group and N-methyl- N- (2,2,2-trifluoroethyl) amino group may be mentioned.
  • Examples of the “C1-C4 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group. Group, tert-butoxy group and 2,2,2-trifluoroethoxy group.
  • examples of the “C1-C4 alkylthio group optionally having one or more halogen atoms” include, for example, methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec- Examples thereof include a butylthio group, a tert-butylthio group and a 2,2,2-trifluoroethylthio group.
  • Examples of the “C1-C4 alkylsulfinyl group optionally having one or more halogen atoms” in the compounds of the present invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutyl group. Examples thereof include a sulfinyl group, a sec-butylsulfinyl group, a tert-butylsulfinyl group, and a 2,2,2-trifluoroethylsulfinyl group.
  • examples of the “C1-C4 alkylsulfonyl group optionally having one or more halogen atoms” include, for example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutyl Examples include a sulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, and a 2,2,2-trifluoroethylsulfonyl group.
  • examples of the “C1-C4 alkylamino group optionally having one or more halogen atoms” include, for example, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutyl
  • An amino group, a sec-butylamino group, a tert-butylamino group and a 2,2,2-trifluoroethylamino group can be mentioned.
  • the “C2-C8 dialkylamino group optionally having one or more halogen atoms” has one or more halogen atoms having 2 to 8 carbon atoms in the alkyl part.
  • Each alkyl group may be the same or different, for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N— Dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methylamino group and N-methyl- N- (2,2,2-trifluoroethyl) amino group may be mentioned.
  • phenyl group (the phenyl group may have one or more groups selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group”) means a methyl group, a methoxy group, Represents a phenyl group which may be substituted with one or more substituents independently selected from the group consisting of a group, a chlorine atom and a nitro group, such as a phenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl Groups, 4-nitrophenyl group, 2-nitrophenyl group, 4-chlorophenyl group, 2-chlorophenyl group, 2,6-dichlorophenyl group and 4-methylphenyl group.
  • Het represents a 5- or 6-membered heteroaromatic ring containing one or more (particularly 1 to 4) heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • a and Q are bonded to the carbon atom or nitrogen atom constituting the 5- or 6-membered heteroaromatic ring, respectively, and the atom to which A is bonded to the atom to which Q is bonded They are not adjacent to each other on the aromatic ring.
  • the 5- or 6-membered heteroaromatic ring represented by Het is selected from the group consisting of —CE 1 ⁇ , —N ⁇ , —O—, —S— and —NE 2 — together with the atoms to which A and Q are bonded.
  • E 1 represents a C1-C2 alkyl group which may have one or more halogen atoms, a hydrogen atom or a halogen atom
  • E 2 represents one or more atoms or groups.
  • a C1-C2 alkyl group which may have a halogen atom is represented.
  • each E 1 group may be the same or different.
  • examples of the 6-membered heteroaromatic ring represented by Het include rings represented by the formulas H1 and H2.
  • the “•” mark on the left side of the structural formula represents the position where it is combined with A
  • the “•” mark on the right side of the structural formula represents the position where it is combined with Q.
  • examples of the 5-membered heteroaromatic ring represented by Het include rings represented by the formulas H3, H4 and H5.
  • [Aspect 6] is “in the formula (1), Q is a group represented by the formulas Q1, Q2, Q3, or Q4, G is a hydrogen atom, a halogen atom, a formula G1, G2, G3, or A heteroaromatic ring compound according to any one of [Aspect 1], [Aspect A] to [Aspect Z] and [Aspect AA] to [Aspect AI], which is a group represented by G4.
  • [Aspect 52] is “in the formula (1), Q is a group represented by the formula Q2, Q3 or Q4, and G is a hydrogen atom, a halogen atom, a group represented by the formula G1, G2, G3 or G4. And [Aspect 1], [Aspect A] to [Aspect Y], and [Aspect AH] to [Aspect AI].
  • examples of the compound of the present invention include the following heteroaromatic ring compounds.
  • L is a single bond or —CH 2 —
  • A is a single bond or —O—
  • J is a group represented by the formula J1 (when J is a group represented by the formula J1, R 1 and R 2 are both methyl groups, and R 3 is a hydrogen atom, a methyl group, or an ethyl group.)
  • a group represented by formula J2 when J is a group represented by formula J2, 4 , R 5 and R 6 are all methyl groups.
  • [Claim 1] [Aspect A] to [Aspect Z]
  • L is a single bond
  • A is a single bond
  • J is a group represented by the formula J1 (when J is a group represented by
  • JLA is a tert-butyl group, [Item 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI], and [Aspect 1] to [Aspect 1] A compound according to any of aspects 143];
  • Q is a group represented by the formula Q1, and R x and R y may be the same or different and may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • Q is a group represented by formula Q2
  • Q is a group of formula Q3
  • Q is a group represented by formula Q4
  • R z is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • Q is a group represented by the formula Q1, and R x and R y are the same or different and are a methyl group or a hydrogen atom, Q is a group represented by formula Q2, or Q is a group represented by formula Q3 and y is 0, or [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect], wherein Q is a group represented by formula Q4 and R z is a methyl group or a hydrogen atom 6] to [Aspect 28];
  • Q is a group represented by the formula Q1, and R x and R y may be the same or different and may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • Q is a group represented by Formula Q2, or Q is a group represented by formula Q3 and y is 0, or [Claim 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [Aspect] wherein Q is a group represented by formula Q4 and R z is a methyl group or a hydrogen atom 2] and the compound according to any one of [Aspect 52] to [Aspect 74];
  • Q is a group represented by the formula Q3, and y is 0 [Item 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [ Aspect 4] and a compound according to any one of [Aspect 98] to [Aspect 120];
  • Q is a group represented by Formula Q2, or Q is a group represented by formula Q3 and y is 0, or [Claim 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [Aspect] wherein Q is
  • G is a group represented by the formula G2, and R b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from ⁇ Group ⁇ >, G is a group represented by the formula G3, and R c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, or , G is a group represented by the formula G4, R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, and R e Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from ⁇ Group ⁇ > [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
  • G is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl group,
  • a C1-C6 chain hydrocarbon which is a group, or G is a group represented by the formula G3, and R c may have one or more atoms or groups selected from ⁇ Group ⁇ > [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AH] and [Aspect 1] to [Aspect 5] which are groups;
  • G is methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, or 2,2,
  • G is a group represented by the formula G1, and R a may
  • Group or G is a group represented by the formula G4, R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, and R e Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from ⁇ Group ⁇ > [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
  • G is methyl group, ethyl group, propyl group, isopropyl group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N.
  • G is a group represented by the formula G1, and R a may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • G is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group or a 2,2,2-trifluoroethoxy group [Claim 1], [Aspect A] to [Aspect Z], [ Compound according to any one of Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5];
  • G is a group represented by the formula G3, and R c may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • G is a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group or a 2,2,2-trifluoroethylthio group [Claim 1], [Aspect A] to [Aspect Z], The compound according to any one of [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5];
  • G is a group represented by Formula G4, and R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >.
  • R e is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from ⁇ Group ⁇ > [Claim 1], [Aspect A ] To [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5];
  • G is N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propyl.
  • examples of the compound of the present invention include the following heteroaromatic ring compounds.
  • G z represents a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C6 alkoxy group (methoxy group, ethoxy group, 2,2, etc.) optionally having one or more halogen atoms.
  • G z represents a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C6 alkoxy group (methoxy group, ethoxy group, 2,2, etc.) optionally having one or more halogen atoms.
  • the heteroaromatic ring compound according to [Claim 1] represented by: The heteroaromatic ring compound according to [Item 1], wherein D is —CH ⁇ and m is 0 in Formula (1y); Formula (1z)
  • G z represents a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C6 alkoxy group (methoxy group, ethoxy group, 2,2, etc.) optionally having one or more halogen atoms.
  • the heteroaromatic ring compound according to [Claim 1] represented by: The heteroaromatic ring compound according to [Item 1], wherein in formula (1z), D is —CH ⁇ and m is 0.
  • the compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 10).
  • (Production method 1) Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q1 can be produced, for example, according to the following scheme.
  • Het1 represents a ring represented by the formula H1, H2, H3 or H4, and R y1 represents ⁇ group ⁇ > Represents a C1-C6 chain hydrocarbon group or a cyclopropyl group which may have one or more atoms or groups selected from: Lg 1 represents a bromine atom or an iodine atom, and Lg 2 represents chlorine It represents a leaving group such as an atom, bromine atom, iodine atom, methanesulfonyloxy group, paratoluenesulfonyloxy group, or trifluoromethanesulfonyloxy group.
  • Compound (3) can be produced by reacting a Grignard reactant produced by reacting compound (5a) with metallic magnesium with an amide compound represented by formula (2).
  • the reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as diethyl ether and tetrahydrofuran.
  • Metallic magnesium is usually used at a ratio of 1 mole per 1 mole of compound (5a), but can be changed as appropriate. Further, if necessary, a catalytic amount of an activator can be added to activate the magnesium metal. Examples of the activator include iodine and 1,2-dibromoethane.
  • the reaction temperature in the reaction between the compound (5a) and metallic magnesium is usually in the range of the boiling point of the solvent used from room temperature, and the reaction time is usually in the range of 1 hour from the instant.
  • Compound (2) is usually used at a ratio of 1 mol per 1 mol of compound (5a), but can be appropriately changed.
  • the reaction temperature in the reaction between the produced Grignard reactant and the compound (2) is usually in the range of ⁇ 78 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
  • Examples of the reduction method include a reduction reaction using sodium borohydride.
  • Sodium borohydride is usually used at a ratio of 0.25 mol to 1 mol with respect to 1 mol of the compound (3), but can be appropriately changed.
  • the reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include alcohols such as methanol, ethanol, isopropyl alcohol and the like.
  • the reaction temperature in the reaction is usually in the range of 0 ° C. to the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 24 hours from the instant.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent examples include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Is mentioned.
  • alkyl lithium compound used in the reaction examples include butyl lithium.
  • the alkyllithium compound is usually used in a proportion of 1 mol with respect to 1 mol of the compound (5a), but can be appropriately changed.
  • the reaction temperature in the reaction between the compound (5a) and the alkyl lithium compound is usually in the range of ⁇ 78 ° C. to ⁇ 50 ° C., and the reaction time is usually in the range of 1 hour from the instant.
  • Compound (6) is usually used at a ratio of 1 mol per 1 mol of compound (5a), but can be appropriately changed.
  • the reaction temperature in the reaction between the reaction intermediate and compound (6) is usually in the range of ⁇ 78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (7) After completion of the reaction, the compound (7) can be isolated by pouring water or an aqueous ammonium chloride solution into the reaction mixture, extracting with an organic solvent, and performing a normal post-treatment operation.
  • ⁇ (4) ⁇ (7) After lithiation of compound (4), compound (7) can be produced by reacting the resulting reaction intermediate with the carbonyl compound represented by formula (16).
  • lithium compound used for lithiation examples include alkyllithium compounds such as butyllithium, sec-butyllithium and tert-butyllithium, and lithium dialkylamide compounds such as lithium diisopropylamide and lithium tetramethylpiperidide.
  • lithiation of a compound in which G is —NHC (O) t-Bu is performed by butyllithium in the presence of N, N, N ′, N′-tetramethylethylenediamine (TMEDA).
  • TEDA tetramethylethylenediamine
  • the reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane.
  • ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane.
  • Butyllithium and TMEDA are usually used in a ratio of 1 mol per 1 mol of compound (4), but can be appropriately changed.
  • the reaction temperature in the reaction between compound (4) and butyl lithium is usually in the range of ⁇ 78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction temperature in the reaction between the reaction intermediate and compound (16) is usually in the range of ⁇ 78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (1a) of the present invention can be produced by dehydroxylating the compound (7).
  • Examples of the dehydroxylation method include a catalytic hydrogen reduction reaction.
  • the catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.
  • the solvent used in the reaction examples include acetic acid. If necessary, a mineral acid such as sulfuric acid can be added. In this case, the molar ratio is usually 0.01 mol to 10 mol with respect to 1 mol of the compound (7).
  • Examples of the catalyst used in the reaction include palladium on carbon.
  • the hydrogen pressure is usually 1 to 5 atm.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • the compound (1a) of the present invention can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.
  • ⁇ (1a) ⁇ (1b) Further, the compound (1b) of the present invention is reacted with a base such as lithium diisopropylamide (hereinafter referred to as LDA) and then reacted with a compound represented by R y1 -Lg 2. ) Can also be manufactured.
  • LDA lithium diisopropylamide
  • R y1 -Lg 2 a compound represented by R y1 -Lg 2.
  • a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q2 can be produced, for example, according to the following scheme.
  • Lg 3 represents a halogen atom.
  • the compound (1c) of the present invention can be produced by reacting the compound (8) with the compound (9) in the presence of a base and, if necessary, a copper compound.
  • Lg 3 is preferably a chlorine atom or a fluorine atom.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • the base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (8).
  • Compound (9) is usually used at a ratio of 1 mol per 1 mol of compound (8), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • Lg 3 is preferably a bromine atom or an iodine atom.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • the base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (8).
  • the copper compound examples include copper powder, copper oxide (I), copper chloride (I), copper bromide (I), copper iodide (I) and the like.
  • the copper compound is usually used in a proportion of 0.01 mol to 10 mol with respect to 1 mol of the compound (8).
  • Compound (9) is usually used at a ratio of 1 mol per 1 mol of compound (8), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 50 ° C. to 200 ° C. or the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
  • the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations. (Production method 3)
  • a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q3 can be produced, for example, according to the following scheme.
  • Lg 3 represents a halogen atom
  • y1 is 1 or 2.
  • the compound (1d) of the present invention is obtained by reacting the compound (10) and the compound (9) in the presence of a base and, if necessary, a copper compound, or the compound (5b) and the compound (11). Can be produced in the presence of a base and, if necessary, a copper compound.
  • Lg 3 is preferably a chlorine atom or a fluorine atom.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • the base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
  • the compound (9) or the compound (5b) is usually used at a ratio of 1 mol per 1 mol of the compound (10) or the compound (11), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • Lg 3 is preferably a bromine atom or an iodine atom.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • the base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
  • the copper compound examples include copper powder, copper oxide (I), copper chloride (I), copper bromide (I), copper iodide (I) and the like.
  • the copper compound is usually used in a proportion of 0.01 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
  • the compound (9) or the compound (5b) is usually used in an amount of 1 mol per 1 mol of the compound (10) or the compound (11), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 50 ° C. to 200 ° C. or the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention (1d) can be isolated by carrying out ordinary post-treatment operations.
  • the compound (1e) of the present invention is produced by reacting the compound (1d) of the present invention with an oxidizing agent such as hydrogen peroxide, metachloroperbenzoic acid (hereinafter referred to as mCPBA), sodium periodate or the like. You can also.
  • mCPBA metachloroperbenzoic acid
  • Lg 3 represents a halogen atom
  • Lg 4 is a halogen atom or a trifluoromethanesulfonyloxy group
  • the compound (1f) of the present invention is obtained by reacting the compound (12) with the compound (9) in the presence of a base and, if necessary, a palladium catalyst, or the compound (5c) and the compound (13). Can be produced in the presence of a base and, if necessary, a palladium catalyst.
  • Lg 3 and Lg 4 are preferably a chlorine atom or a fluorine atom.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • Examples of the base used in the reaction include organic bases such as pyridine, triethylamine and diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like.
  • the base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (12) or compound (13).
  • the compound (9) or the compound (5c) is usually used at a ratio of 1 mol per 1 mol of the compound (12) or the compound (13), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • Lg 3 and Lg 4 are preferably a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. .
  • Examples of the base used in the reaction include sodium tert-butoxide, cesium carbonate and the like.
  • the base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (12) or compound (13).
  • Examples of the palladium catalyst used in the reaction are ⁇ 1,1′-bis (diphenylphosphino) ferrocene ⁇ dichloropalladium and tris (dibenzylideneacetone) dipalladium (hereinafter referred to as Pd 2 (dba) 3 . ) And 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene (hereinafter referred to as xanthophos), and the like.
  • the palladium catalyst is usually used in a proportion of 0.01 to 0.2 mol with respect to 1 mol of the compound (12) or compound (13).
  • the compound (9) or the compound (5c) is usually used at a ratio of 1 mol per 1 mol of the compound (12) or the compound (13), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 20 ° C to 100 ° C.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention (1f) can be isolated by carrying out ordinary post-treatment operations.
  • Production method 5 Among the compounds of the present invention, a compound in which D is —N ⁇ , Het is a ring represented by the formula H1, H2, H3 or H4, and Q is a group represented by the formula Q2, Q3 or Q4 is, for example, It can be produced according to the following scheme.
  • Compound (15) can be produced by reacting compound (14) with dihalopyrimidine compound (16) in the presence of a base.
  • Two Lg 3 in the compound (16) may be different from each other, but a compound in which the two Lg 3 are both chlorine atoms is preferable.
  • the reaction can be carried out according to the above Production Method 2 (1), Production Method 3 (1) or Production Method 4 (1).
  • the compound (1g) of the present invention can be produced by dehalogenating the compound (15).
  • Examples of the dehalogenation method include a catalytic hydrogen reduction reaction.
  • the catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.
  • Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, esters such as ethyl acetate, carboxylic acids such as acetic acid, and water.
  • the molar ratio is usually 0.01 mol to 10 mol with respect to 1 mol of compound (15).
  • Examples of the base used in the reaction include magnesium oxide, sodium hydroxide, sodium acetate, and triethylamine.
  • Examples of the acid include sulfuric acid and hydrochloric acid.
  • Examples of the catalyst used in the reaction include palladium on carbon.
  • the hydrogen pressure is usually 1 to 5 atm.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention (1 g) can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.
  • (Production method 6) Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H5 can be produced, for example, according to the following scheme.
  • solvent used in the reaction examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • the base is generally used in the proportion of 1 mol to 10 mol with respect to 1 mol of the compound (17).
  • Compound (18) is usually used in a ratio of 1 mol per 1 mol of compound (17), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
  • the reaction time in the reaction is usually in the range of 0.1 to 24 hours.
  • R b1 has one or more atoms or groups selected from ⁇ Group ⁇ >.
  • R b2 represents a protecting group for an OH group (for example, a methyl group, a methoxymethyl group, a benzyl group, etc.)
  • Lg 2 represents a chlorine atom, a bromine atom
  • a leaving group such as an iodine atom, a methanesulfonyloxy group, a paratoluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group is represented.
  • the compound (1j ′) of the present invention can be produced by reacting the compound (1i) of the present invention with R b1 OH in the presence of a base.
  • reaction is usually performed in the presence of a solvent, but R b1 OH may be used in an amount of a solvent.
  • solvent used in the reaction examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • N, N-dimethylformamide examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • R b1 OH is usually used in a proportion of 1 to 10 mol and a base is usually used in a proportion of 1 to 10 mol per mol of the compound (1i) of the present invention.
  • the reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention (1j ′) can be isolated by carrying out ordinary post-treatment operations.
  • ⁇ (1l) ⁇ (1k) The compound (1k) of the present invention can be produced by deprotecting the compound (1l).
  • Examples of the protecting group R b2 include a methyl group, a methoxymethyl group, and a benzyl group, which can be deprotected by methods known to those skilled in the art.
  • ⁇ (1k) ⁇ (1j) The compound (1j) of the present invention can be produced by reacting the compound (1k) of the present invention with R b Lg 2 in the presence of a base.
  • solvent used in the reaction examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • N, N-dimethylformamide examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide.
  • Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like.
  • the base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (1k) of the present invention.
  • R b Lg 2 is used usually in a proportion of 1 mole, but may be appropriately changed.
  • the reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually from 0.1 to 24 hours.
  • the compound (1j) of the present invention can be isolated by carrying out an ordinary post-treatment operation after the completion of the reaction.
  • this invention compound (1j) includes this invention compound (1j ').
  • (Production method 8) Among the compounds of the present invention, a part of the compounds in which G is a group represented by the formula G3 can be produced, for example, according to the following scheme.
  • R c1 may have one or more atoms or groups selected from ⁇ Group ⁇ >. Represents a C1-C6 chain hydrocarbon group.
  • the compound (1m) of the present invention can be produced by reacting the compound (1i) of the present invention with R c1 SH in the presence of a base.
  • solvent used in the reaction examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • N, N-dimethylformamide examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
  • R 1 C1 SH is usually used in a proportion of 1 to 10 mol and a base is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (1i) of the present invention.
  • the reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually from 0.1 to 24 hours.
  • the compound of the present invention (1m) can be isolated by carrying out ordinary post-treatment operations.
  • the compound (1m) of the present invention is further subjected to an oxidation reaction known to those skilled in the art to convert -SR c1 in the compound (1m) of the present invention to —S (O) z1 R c1 (in this case) , Z1 represents 1 or 2).
  • an oxidation reaction known to those skilled in the art to convert -SR c1 in the compound (1m) of the present invention to —S (O) z1 R c1 (in this case) , Z1 represents 1 or 2).
  • G4 is a group represented by the formula G4
  • Lg 2 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a para A leaving group such as a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group is represented.
  • ⁇ (1n) ⁇ (1o) The compound (1o) of the present invention can be produced by reacting the compound (1n) of the present invention with R d Lg 2 in the presence of a base.
  • solvent used in the reaction examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • N, N-dimethylformamide examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide.
  • Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like.
  • the base is generally used in a proportion of 1 mol to 2 mol with respect to 1 mol of the compound (1n) of the present invention.
  • R d Lg 2 is used usually in a proportion of 1 mole may be suitably changed.
  • the reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention (1o) can be isolated by carrying out ordinary post-treatment operations.
  • the compound (1o), by reacting R e Lg 2 is prepared by an analogous procedure to the above, it can be produced the present invention compound (1p).
  • R d or R e is a primary or secondary alkyl group
  • the present compound (1n) or the present compound (1o) and an aldehyde or ketone compound are reduced instead of the above method.
  • the present compound (1o) or the present compound (1p) can also be produced by reacting in the presence of an agent.
  • Examples of the reducing agent used in the reaction include sodium triacetoxyborohydride.
  • Sodium triacetoxyborohydride is used in a ratio of 1 to 5 mol per 1 mol of the compound (1n) or the compound (1o) of the present invention.
  • solvent used in the reaction examples include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane and chloroform, and the like. A mixture is mentioned. Moreover, it reacts by adding carboxylic acids, such as an acetic acid, as needed.
  • the aldehyde or ketone compound is usually used at a ratio of 1 mole per 1 mole of the compound (1n) or the compound (1o) of the present invention, but can be appropriately changed.
  • the reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention (1o) or the compound of the present invention (1p) can be isolated by carrying out ordinary post-treatment operations.
  • a compound in which m is 1 can be produced, for example, according to the following scheme.
  • the compound (1r) of the present invention can be produced by reacting the compound (1q) of the present invention with an oxidizing agent.
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, water, and mixtures thereof.
  • oxidizing agent used in the reaction examples include peroxides of carboxylic acids such as 3-chloroperbenzoic acid, hydrogen peroxide water, and the like.
  • the oxidizing agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the compound (1q) of the present invention.
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (1r) of the present invention can be isolated by carrying out ordinary post-treatment operations.
  • the compounds of the present invention there are also compounds capable of forming acid addition salts such as hydrochloride, nitrate, sulfate, hydrobromide, phosphate, carbonate, acetate, lactate, citrate, etc. To do.
  • acid addition salts such as hydrochloride, nitrate, sulfate, hydrobromide, phosphate, carbonate, acetate, lactate, citrate, etc.
  • the production of these acid addition salts can also follow conventional methods, and the present invention also includes these acid addition salts.
  • pests for which the compounds of the present invention are effective include harmful arthropods such as harmful insects and harmful mites, linear animals and molluscs. 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 (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypi), peach aphids (Myzus persicae), radish aphids (Brevicorine brassicae), aphid spiraecola, tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum pasid), citrus aphids (
  • Lepidoptera rice stem borer (Chilo suppressalis), Sankameiga (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), Common moths such as Shibatatsuga (Pediasia teterrellus), Lotus moth (Spodoptera litura), Spodoptera exigua, Ayuyotoga (Pseudaletia separata), Yotoga Mestra brassicae, Agrotis ipsilon, Tamanagine waba (Plusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc.
  • Leafhoppers such as Archipes fuscocuppreanus, Cydonia pomonella, etc.
  • Spiders such as leaf moths, Limantria, Euprocutis, etc., Suga such as Plutella xylostella, Pterinophora gossypiella, Phythromea operphylla such as Phythoreaea operculella Hitrigues such as ia cunea, and Hirokosukoga such as iga (Tinea translucens), Koiga (Tineola bisselliella) and the like.
  • Suga such as Plutella xylostella
  • Pterinophora gossypiella Phythromea operphylla
  • Phythoreaea operculella Hitrigues such as ia cunea
  • Hirokosukoga such as iga (Tinea translucens), Koiga (Tineola bisselliella) and the like.
  • Thrips of the order Thrips thrips Thrips of the order Thrips thrips, Sriptotrips dorsalis, Sriptorips dorsalis
  • 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. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc.
  • Moguribae (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, fleas such as Megaselia spiracularis, Clogmial etc. Flies such, blackfly acids, Abu such as gadfly (Tabanus trigonus), and stable flies and the like.
  • Coleoptera pests Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Maizeweville (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Azuki weevil (Callosobrchuchus Kunststoffsis), Rice weevil (Echinocnemus squatius) Weevil (Anthonomus grandis), Weevil weevil (Sphenophorus venatus) and other weevil, Tenebrio molitor, Aureum oleume olium (Olymoidum) Leaf beetles such as Phyllotreta striola, Colorado potato beetle
  • Shimushi Shibamushi (Lasiderma serricorne), etc .
  • Japanese beetles longicorn beetles such as Anophorora malasiaca, click beetles (Agriotes spp.), And long-horned beetle (Paederus fuscipes).
  • Pterodoptera Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, Oroja japonica, etc.
  • Insect pests cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mouse fleas (Xenopsilla cheopes) and the like.
  • Lice insect pests Japanese lice (Pediculus humnus corporis), pheasants (Phythrus pubis), cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ostois aus pis)
  • Hymenoptera Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Such as ants, hornets, hornets, bees (Athalia rosae), Japanese bees (Athalia japonica), and the like.
  • Cockroach eye pests German cockroaches (Blatella germanica), Black cockroaches (Periplaneta fuliginosa), Cockroach cockroach (Periplaneta americana), Japanese cockroach (Peripraneta bruna)
  • Termite pests Yamato termites (Reticulitermes supertus), Japanese termites (Coptothermes formosanus), American white termites (Incitermes minors), Cyptotermes domesticus, Glypoptermes satsumensis, Gyptotermes nakajimai, Caterpillars (Glyptotermes fuscus), Termites (Glypoptermes kodamai), Shimotoshiroari (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R.
  • flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis ), Termites termites (Pericapritermes nitobei), termites termites (Sinocapriters mushae), Reticulitermes fl ipes, Reticulitermes hesperus, Reticulitermes virginicus, Reticulitermes tibialis, Heterotermes aureus, Zootermopsis nevadensis or the like.
  • 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), Chanosabi mites (Calacarus carinatus), Chanogasabi mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple scab mites Achulus schizus endali) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yama
  • Lip limb class Geji (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes), etc.
  • Double-legged class Oxidus gracilis, Nadeyopus tambanus, etc.
  • Isopods Armadillium vulgare, etc.
  • Gastropods Limax marginatus, Limax flavus, etc.
  • 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 nectar (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus) and the like.
  • 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, liquid carrier, gaseous carrier, etc., and if necessary, a surfactant and other formulation adjuvants are added.
  • an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, etc.
  • a surfactant and other formulation adjuvants are added.
  • they are formulated into emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smoke agents, poison baits, resin formulations and the like.
  • 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). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine fertilizers such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.) and granular materials.
  • 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 examples 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 negative ions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate.
  • nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether and polyethylene glycol fatty acid ester
  • negative ions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate.
  • An ionic surfactant is mentioned.
  • adjuvants for preparation include fixing 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).
  • fixing 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 (is
  • the pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention directly to pests and / or to habitats of pests (plants, soil, households, animal bodies, etc.). .
  • the compound of the present invention is usually used in the form of the pest control agent of the present invention.
  • the application amount is 1 to 10,000 g in the amount of the present compound per 10,000 m 2 .
  • the pest control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually applied after diluting with water so that the concentration of the compound of the present invention is 0.01 to 10,000 ppm. Granules, powders and the like are usually applied as they are.
  • 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 the soil of cultivated land. You may process to soil.
  • it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
  • the amount applied is the amount of the compound of the present invention per 1 m 2 of treatment area when treated on the surface, usually 0.01. In the case of treatment in a space, the amount of the compound of the present invention per 1 m 3 of the treatment space is usually 0.01 to 500 mg.
  • the pest control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the compound of the present invention is 0.1 to 1000 ppm, and applied. Apply oils, aerosols, smoke, poison baits, etc. as they are.
  • 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.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, American scallop, 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, eel, 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.
  • active ingredients of such insecticides, acaricides, nematicides, fungicides, herbicides and synergists are shown below.
  • Phenylpyrazole compounds Acetoprole, Ethiprole, Fipronil, Vaniliprole, Pyriprole, and Pyrafluprole.
  • Bt toxin insecticide Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.
  • Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
  • Machine oil Machine oil
  • nicotine sulfate Nicotine-sulfate
  • nicotine Nicotine
  • abamectin Abamectin
  • emamectin benzoate Emamectin-benzoate
  • milbemectin Milbemectin
  • Pyriproxyfen Phenoxycarb
  • Chlorphenapyr DNOC
  • Diafenthiuron Pymetrozine, Pymetrozine, Pymetrozine Tolfenpyrad, Flurimfen, Flufenerim, Spirotetramat, Spiromesifen, Sulfoxaflor, Chloranthrolitrol orantraniliprole, cyantraniliprole
  • R 100 represents a chlorine atom, a bromine atom or a trifluoromethyl group
  • R 200 represents a chlorine atom, a bromine atom or a methyl group
  • R 300 represents a chlorine atom, a bromine atom or a cyano group.
  • R 1000 represents a chlorine atom, a bromine atom or an iodine atom.
  • Methoxadiazone sulfuramide, arsenous acid, benclothiaz, lime nitrogen (Calcium flude) (Calcium flude) ammonium, Metam-sodium, Potassium oleate, Sulfur, and Tralopyril.
  • Active ingredients of acaricides Acequinocyl, Amitraz, Benzoximate, Bifenaate, Bromopropyl, BSPC, Chromethionate, Chromethionate ), Clofentezine, cyflumetofen, dicofol, etoxazole, fenazaquin, fenbutatin oxide, fenothiophen Pyroximate, Fluacrylpyrim, Hexythiaxox, propargite (di), di (R), pyridene (P), piridaben (Pyriben) Diclofen, Spirodiclofen, Amidoflumet, and Cyenopyrafen.
  • Active ingredients of fungicides Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Difenaconol, Dinicoconol D, Iniconazole E (Fenarimol) Fenbuconazole, Flucilazole, Fluquinconazole, Flutriafol, Hexaconazole, Imazaril (Imazalil) Imibenconazole, Ipconazole, Iconazole, Metconazole, Microbutanil, Nuarimol, Oxpoconazole, Puroazo Propiconazole, Prothioconazole, Pyrifenox, Simeconazole, Tebuconazole, Tetraconazole, Triazimone fon), triadimenol (Triadimenol), triflumizole (Triflumizole), trifolin (Trifolin), triticonazole (Triticonazole), aldimorph (Dodimorph), dodemorph (M
  • Carbamate herbicidal compound Di-allate, Tri-alate, EPTC, Butyrate, Benchiocarb, Esprocarb, Molinate, Dimepiperate, Dimepiperate (Swep), Chlorprofham, Phenmedifam, Phenisopham, Pyributicalb, and Asuram.
  • Acid amide herbicidal compound Propanil, Propyzamide, Bromobutide, and Etobenzanide.
  • Chloroacetanilide herbicidal compounds Acetochlor, Alaclor, Butachlor, Dimethenamide, Propaclor, Metazachlor, Metolachlor, Metolachlor Pretilachor), tenylchlor (Theny1ch1or), and petoxamide (Pethoxamide).
  • Diphenyl ether herbicidal compound acifluorfen (Acifluorfen-sodium), bifenox (Oxyfluorfen), lactofen (Lactofen), fomesafen (Chlophenoxy), clomethoxypheny (Chlophenoxy)
  • Cyclic imide herbicidal compounds Oxadiazone, Cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumilacrac-pentyl Oxazine (Flumioxazin), Pyraflufen-ethyl, Oxadiargyl (Oxadialy), Pentoxazone, Fluthiacet-methyl, Butafenzene (Butafenzil) azone), and saflufenacil.
  • Trione oxime herbicidal compounds Alloxydim-sodium, cetoxydim, Butroxidim, Crethodim, Cloproxidim, Cyclodimoxime (Tralkoxydim), and Profoxydim.
  • Sulphonylurea herbicidal compound Chlorsulfuron, Sulfomethuron-methyl, Metsulfuron-methyl, Chlorimuron-ethyl, Tribenuron methyl Tribenuron-methyl), trisulfuron (Triasulfuron), bensulfuron-methyl (Bensulfuron-methy1), thifensulfuron-methyl (Pyrazsulfuron-methyl), pyrysulfururon-methyl- (1) Nicosulfuron (Nico sulfuron, amidosulfuron, minosulfuron, imosulfuron, rimsulfuron, halosulfuronmethyl (Halsulfuron-sulfuron) , Trifluor
  • active ingredients that can be used in combination or in combination, particularly preferred examples include active ingredients of insecticides such as cartap hydrochloride, fipronil, methoxyphenozide, tebufenozide, clothianidin, spinosad, spinetoram, chlorantraniliprole, cyantraniliprole
  • active ingredients of fungicides such as diclocimet, fusaride, tricyclazole, pyroxylone, azoxystrobin, metminostrobin, orisatrobin, flutolanil, furamethpyr, tifluzamide, probenazole, thiazinyl, isothianyl, validamycin, kasugamycin, and ferrimzone.
  • N-dimethylformamide was added 0.30 g of 3- (2,2-dimethylpropyl) -1H-1,2,4-triazole at 0 ° C., and at room temperature. Stir for 5 minutes.
  • 0.35 g of 4-chloromethylpyridine hydrochloride was added at 0 ° C., and the mixture was stirred at 50 ° C. for 10 minutes. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • Me is a methyl group (CH 3 —)
  • Et is an ethyl group (CH 3 CH 2 —)
  • Pr is a propyl group (CH 3 CH 2 CH 2 —)
  • i-Pr is an isopropyl group ((CH 3 )).
  • 2 CH—) and t-Bu represent a tert-butyl group ((CH 3 ) 3 C—)
  • sec-Bu represents a sec-butyl group (CH 3 CH 2 CH (CH 3 ) —).
  • the JLA group, (E 1 ) n , Q, D, G and m represent the combinations described in the following [Table 7] to [Table 10].
  • JLA group, (E 1 ) n , Q, D, G and m represent the combinations described in the following [Table 11] to [Table 12].
  • the JL group, E 1 , Q, D, G and m in the formula represent the combinations described in the following [Table 17] to [Table 18].
  • the JLA group, (E 1 ) n , R x , R y , D, G and m represent the combinations described in the following [Table 19] to [Table 22].
  • JLA group, E 1 , R x , R y , D, G and m represent the combinations described in the following [Table 23] to [Table 24].
  • a part represents a weight part.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of a synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth were mixed, and the above-mentioned compounds 1-1 to 1-68, compounds 2-1 to 2-34, 20 parts of any one of compounds 3-1 to 3-68, compounds 4-1 to 4-34, compounds 5-1 to 5-102 and compounds 6-1 to 6-34 are added and mixed to Get wettable powder.
  • Formulation Example 3 Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 1 part of any one of 1 to 6-34 is mixed with 1 part of synthetic hydrous silicon fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay. 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 5 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), the above-mentioned compounds 1-1 to 1-68, compounds 2-1 to 2-34, compounds 3-1 to 3 -68, compound 4-1 to 4-34, compound 5-1 to 5-102, compound 6-1 to 6-34 10 parts of any one and water 55 parts are mixed, and wet pulverization method is used. Each preparation is obtained by fine grinding.
  • Formulation Example 7 Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 10 mg of any one of 1 to 6-34 is dissolved in 0.5 ml of acetone, and this solution is treated with 5 g of animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd.). Mix evenly. Then, acetone is evaporated to dryness to obtain each poisonous bait.
  • animal solid feed powder termed breeding solid feed powder CE-2, Nippon Claire Co., Ltd.
  • Formulation Example 8 Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- Put 1 part of 1 to 6-34 0.1 part and 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) into an aerosol can, attach an aerosol valve, then fill with 25 parts of dimethyl ether and 25 parts of LPG and shake. And an oil aerosol is obtained by mounting the actuator.
  • Neothiozole Cho Kasei Co., Ltd.
  • Formulation Example 10 Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- Add 5 parts of any one of 1 to 6-34 and 5 parts of ferrimzone into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon hydroxide fine powder and the remainder of diatomaceous earth, Mix well and obtain 100 parts of wettable powder.
  • Formulation Examples 11-25 instead of 5 parts of ferrimzone, the same operation as in Preparation Example 10 was carried out except that each compound and the amount used described in [Table 26] were applied to obtain 100 parts of each wettable powder.
  • Test example 1 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 500 ppm to prepare a test drug solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Test example 2 The formulation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 500 ppm to prepare a test spray solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Test example 3 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 200 ppm to prepare a test drug solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Test example 4 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 200 ppm to prepare a test spray solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • the compound of the present invention is useful for controlling pests.

Abstract

The present invention provides a novel compound that has control activity against pests. The present invention relates to: a heteroaromatic ring compound that is represented by formula (1); a method for producing the heteroaromatic ring compound; and a pest control agent that contains the heteroaromatic ring compound. (In the formula, Het represents a five-membered or six-membered heteroaromatic ring that contains one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom; J represents a tert-butyl group or the like; L represents a single bond, a C1-C3 alkylene group or the like; A represents a single bond or the like; Q represents a methylene group or the like; G represents a hydrogen atom, a halogen atom or the like; D represents -N= or -CH=; and m represents 0 or 1.)

Description

ヘテロ芳香環化合物およびその有害生物防除用途Heteroaromatic compounds and their use for pest control
　本発明はヘテロ芳香環化合物およびその有害生物防除用途に関する。 The present invention relates to a heteroaromatic ring compound and its use for pest control.
　有害生物に対して防除活性を有する化合物が有害生物防除剤の有効成分として見出され、開発されている。 A compound having a pest control activity has been found and developed as an active ingredient of a pest control agent.
　非特許文献１には、分子内にチオフェン環とピリジン環とを有する化合物が記載されている。 Non-Patent Document 1 describes a compound having a thiophene ring and a pyridine ring in the molecule.
　本発明は、有害生物に対して防除活性を有する新規な化合物を提供することを課題とする。 An object of the present invention is to provide a novel compound having a controlling activity against pests.
　本発明者等は、有害生物に対して防除活性を有する化合物を見出すべく検討した結果、下記式（１）で示される化合物が有害生物に対して防除効力を有することを見出し、更に検討を重ねた結果本発明を完成するに至った。 As a result of studies to find a compound having control activity against pests, the present inventors have found that the compound represented by the following formula (1) has a control effect on pests, and further studies have been made. As a result, the present invention has been completed.
　即ち、本発明は以下のものである。
［項１］　式（１） That is, the present invention is as follows.
[Term 1] Formula (1)
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
〔式中、
　Ｈｅｔは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる１個以上のヘテロ原子を含む５または６員へテロ芳香環を表し（ここで、ＡおよびＱはそれぞれ、該５または６員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５または６員へテロ芳香環上で互いに隣接することはない。該５または６員へテロ芳香環は、Ａ及びＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝、－Ｏ－、－Ｓ－および－ＮＥ２－からなる群より選ばれる３もしくは４個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子を表し、Ｅ２は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基を表す。）、
　Ｊは、下式Ｊ１またはＪ２： [Where,
Het represents a 5- or 6-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (wherein A and Q are the 5- or 6-membered members, respectively) The atom bonded to the carbon atom or nitrogen atom constituting the heteroaromatic ring, and the atom bonded to A and the atom bonded to Q are not adjacent to each other on the 5- or 6-membered heteroaromatic ring. The 6-membered heteroaromatic ring has 3 or 4 atoms selected from the group consisting of —CE 1 ═, —N═, —O—, —S— and —NE 2 — together with atoms to which A and Q are bonded. Or E 1 represents a C1-C2 alkyl group which may have one or more halogen atoms, a hydrogen atom or a halogen atom, and E 2 has one or more halogen atoms. Represents a C1-C2 alkyl group ),
J is the following formula J1 or J2:
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
（式中、
　Ｒ1およびＲ2は、同一または相異なり、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ３アルキル基を表し、
　Ｒ3は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６鎖式炭化水素基、ハロゲン原子または水素原子を表し、
　Ｒ4およびＲ5は、同一または相異なり、Ｃ１－Ｃ３アルキル基を表し、
　Ｒ6は、水素原子またはＣ１－Ｃ６鎖式炭化水素基を表す。）で示される基を表し、
　Ｌは、単結合または１個以上のハロゲン原子を有していてもよいＣ１－Ｃ３アルキレン基を表し、
　Ａは、ＡがＨｅｔで表される該５または６員へテロ芳香環を構成する炭素原子に結合する場合には、単結合、－Ｏ－、または－Ｓ（Ｏ）x－を表し（ここで、ｘは、０、１または２を表す。）、ＡがＨｅｔで表される該５または６員へテロ芳香環を構成する窒素原子に結合する場合には、単結合を表し、
　Ｑは、ＱがＨｅｔで表される該５または６員へテロ芳香環を構成する炭素原子に結合する場合には、下式Ｑ１、Ｑ２、Ｑ３またはＱ４： (Where
R 1 and R 2 are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R 3 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
R 4 and R 5 are the same or different and represent a C1-C3 alkyl group,
R 6 represents a hydrogen atom or a C1-C6 chain hydrocarbon group. ) Represents a group represented by
L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms,
A represents a single bond, —O—, or —S (O) x — when A is bonded to the carbon atom constituting the 5- or 6-membered heteroaromatic ring represented by Het (here, X represents 0, 1 or 2.), when A is bonded to the nitrogen atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, it represents a single bond;
When Q is bonded to a carbon atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, the following formula Q1, Q2, Q3 or Q4:
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
（式中、
　ＲxおよびＲyは、同一または相異なり、＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、シアノ基、ハロゲン原子、水素原子またはシクロプロピル基を表し、
　ｙは０、１または２を表し、
　Ｒzは、＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1、－Ｓ（Ｏ）2－Ｔ2、水素原子またはシクロプロピル基を表し、
　Ｔ1は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ１２ジアルキルアミノ基、水酸基、アミノ基、水素原子またはシクロプロピル基を表し、
　Ｔ2は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基を表す。）
で示される基を表し、
　ＱがＨｅｔで表される該５または６員へテロ芳香環を構成する窒素原子に結合する場合には、Ｑは式Ｑ１で示される基を表し、
　Ｇは、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、メルカプト基もしくはアミノ基を表すか、または、下式Ｇ１、Ｇ２、Ｇ３もしくはＧ４： (Where
R x and R y are the same or different and each may have one or more atoms or groups selected from <Group α>, C1-C6 chain hydrocarbon group, cyano group, halogen atom, hydrogen atom Or a cyclopropyl group,
y represents 0, 1 or 2;
R z is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group α>, —C (O) —T 1 , —S (O) 2 —. T 2 represents a hydrogen atom or a cyclopropyl group,
T 1 has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, a hydroxyl group, an amino group, a hydrogen atom or a cyclopropyl group,
T 2 represents a C1-C6 alkyl group which may have one or more halogen atoms. )
Represents a group represented by
When Q is bonded to a nitrogen atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, Q represents a group represented by the formula Q1;
G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or the following formulas G1, G2, G3 or G4:
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
｛式中、
　Ｒaは、＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、シクロプロピル基または－Ｃ（Ｏ）－Ｔ1を表し、
　Ｒbは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1、－Ｓ（Ｏ）2－Ｔ2、Ｃ３－Ｃ９トリアルキルシリル基またはシクロプロピル基を表し、
　Ｒcは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1またはシクロプロピル基を表し、
　ｚは０、１または２を表し、
　Ｒdは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1、－Ｓ（Ｏ）2－Ｔ2またはシクロプロピル基を表し、
　Ｒeは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、水素原子またはシクロプロピル基を表す。
（ここで、Ｔ1およびＴ2は前述と同義であるが、Ｇが式Ｇ２、Ｇ３またはＧ４で示される基の場合には、Ｔ1は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ１２ジアルキルアミノ基、アミノ基、水素原子またはシクロプロピル基を表す。）｝で示される基を表し、
　Ｄは－Ｎ＝または－ＣＨ＝を表し、
　ｍは０または１を表す。
＜群α＞：ハロゲン原子、シアノ基およびシクロプロピル基からなる群、
＜群β＞：１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルチオ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルホニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ８ジアルキルアミノ基、ハロゲン原子、シアノ基、Ｃ３－Ｃ９トリアルキルシリル基およびシクロプロピル基からなる群、
＜群γ＞：１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルチオ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルホニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ８ジアルキルアミノ基、フェニル基（該フェニル基は、メチル基、メトキシ基、塩素原子およびニトロ基からなる群より選ばれる１個以上の基を有していてもよい。）、ハロゲン原子、シアノ基、Ｃ３－Ｃ９トリアルキルシリル基およびシクロプロピル基からなる群。〕
で示されるヘテロ芳香環化合物。（以下、本発明化合物と記す。）。
［項２］　Ｈｅｔが下式Ｈ１またはＨ２： {Where,
R a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T 1 which may have one or more atoms or groups selected from <Group β>
R b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, —C (O) —T 1 , —S (O) 2 —. T 2 represents a C3-C9 trialkylsilyl group or a cyclopropyl group,
R c represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group γ>, —C (O) —T 1 or a cyclopropyl group;
z represents 0, 1 or 2;
R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, —C (O) —T 1 , —S (O) 2 —. Represents T 2 or a cyclopropyl group,
R e represents a C1-C6 chain hydrocarbon group, a hydrogen atom or a cyclopropyl group which may have one or more atoms or groups selected from <Group γ>.
(Here, T 1 and T 2 are as defined above, but when G is a group represented by the formula G2, G3 or G4, T 1 may have one or more halogen atoms. A good C1-C6 alkyl group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, one or more Represents a C2-C12 dialkylamino group optionally having a halogen atom, an amino group, a hydrogen atom or a cyclopropyl group.)}
D represents —N═ or —CH═,
m represents 0 or 1;
<Group α>: Group consisting of halogen atom, cyano group and cyclopropyl group,
<Group β>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms A group consisting of an amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, a C3-C9 trialkylsilyl group, and a cyclopropyl group;
<Group γ>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms An amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a phenyl group (the phenyl group is one selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group) And a group consisting of a halogen atom, a cyano group, a C3-C9 trialkylsilyl group and a cyclopropyl group. ]
The heteroaromatic ring compound shown by these. (Hereinafter referred to as the present compound).
[Item 2] Het is represented by the following formula H1 or H2:
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
（式中、
　Ｘ１、Ｘ２、Ｘ３およびＸ４は、同一または相異なり、－ＣＥ１＝または－Ｎ＝を表す。 (Where
X 1 , X 2 , X 3 and X 4 are the same or different and represent —CE 1 ═ or —N═.
　但し、Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの少なくとも１つは－Ｎ＝を表す。）
で示される基である［項１］に記載のヘテロ芳香環化合物。
［項３］　Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの１つが－Ｎ＝であり、それ以外が、同一または相異なり、－ＣＥ１＝である［項２］に記載のヘテロ芳香環化合物。
［項４］　Ｈｅｔが式Ｈ１で示される基である［項３］に記載のヘテロ芳香環化合物。
［項５］　Ｈｅｔが下式Ｈ３、Ｈ４またはＨ５： Provided that at least one of X 1, X 2, X 3 and X 4 represent -N =. )
The heteroaromatic ring compound according to [Item 1], which is a group represented by:
[Claim 3] The heteroaromatic compound according to [Claim 2], wherein one of X 1 , X 2 , X 3 and X 4 is —N═, and the others are the same or different and —CE 1 ═. Ring compound.
[Claim 4] The heteroaromatic ring compound according to [Claim 3], wherein Het is a group represented by the formula H1.
[Item 5] Het is represented by the following formula H3, H4 or H5:
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
（式中、
　Ｙ１、Ｙ２およびＹ３のうちの１つは、－Ｏ－、－Ｓ－または－ＮＥ２－を表し、残りの２つは、同一または相異なり、－ＣＥ１＝または－Ｎ＝を表し、
　Ｚ１、Ｚ２およびＺ３は、同一または相異なり、－ＣＥ１＝または－Ｎ＝を表す。）
で示される基である［項１］に記載のヘテロ芳香環化合物。
［項６］　Ｈｅｔが式Ｈ３で示される基である［項５］に記載のヘテロ芳香環化合物。
［項７］　Ｙ１、Ｙ２およびＹ３のうちの１つが－Ｓ－である［項６］に記載のヘテロ芳香環化合物。
［項８］　Ｙ１、Ｙ２およびＹ３のうちの１つが－Ｓ－であり、それ以外が、同一または相異なり、－ＣＥ１＝である［項７］に記載のヘテロ芳香環化合物。
［項９］　Ｙ１が－Ｓ－である［項７］に記載のヘテロ芳香環化合物。
［項１０］　Ｙ１が－Ｓ－であり、Ｙ２およびＹ３が、同一または相異なり、－ＣＥ１＝である［項９］に記載のヘテロ芳香環化合物。
［項１１］　Ｈｅｔが式Ｈ４で示される基である［項５］に記載のヘテロ芳香環化合物。
［項１２］　Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、かつ、Ｚ３が－ＣＥ１＝または－Ｎ＝であるか、あるいは、Ｚ１が－ＣＥ１＝であり、Ｚ２が－Ｎ＝であり、かつ、Ｚ３が－ＣＥ１＝である［項１１］に記載のヘテロ芳香環化合物。
［項１３］　Ｚ１が－Ｎ＝であり、Ｚ２およびＺ３が同一または相異なり－ＣＥ１＝であるか、あるいは、Ｚ２が－Ｎ＝であり、Ｚ１およびＺ３が同一または相異なり－ＣＥ１＝である［項１２］に記載のヘテロ芳香環化合物。
［項１４］　Ｈｅｔが式Ｈ５で示される基である［項５］に記載のヘテロ芳香環化合物。
［項１５］　Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、かつ、Ｚ３が－ＣＥ１＝または－Ｎ＝であるか、あるいは、Ｚ１が－ＣＥ１＝であり、Ｚ２が－Ｎ＝であり、かつ、Ｚ３が－ＣＥ１＝である［項１４］に記載のヘテロ芳香環化合物。
［項１６］　Ｚ１が－Ｎ＝であり、Ｚ２およびＺ３が同一または相異なり－ＣＥ１＝であるか、あるいは、Ｚ２が－Ｎ＝であり、Ｚ１およびＺ３が同一または相異なり－ＣＥ１＝である［項１５］に記載のヘテロ芳香環化合物。
［項１７］　Ｈｅｔが、窒素原子、および硫黄原子からなる群より選ばれる１個以上のヘテロ原子を含む５または６員へテロ芳香環であり（ここで、ＡおよびＱはそれぞれ、該５または６員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５または６員へテロ芳香環上で互いに隣接することはない。該５または６員へテロ芳香環は、Ａ及びＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝および－Ｓ－からなる群より選ばれる３もしくは４個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子である。）、
　Ｊが、式Ｊ１またはＪ２（Ｒ1およびＲ2が、同一または相異なり、Ｃ１－Ｃ３アルキル基であり、Ｒ3が、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒ4およびＲ5が、同一または相異なり、Ｃ１－Ｃ３アルキル基であり、Ｒ6が、Ｃ１－Ｃ６鎖式炭化水素基である。）で示される基であり、
　Ｌが、単結合またはＣ１－Ｃ３アルキレン基であり、
　Ａが単結合であり、
　Ｑが式Ｑ１（ＲxおよびＲyが、水素原子である。）で示される基であり、
　Ｇが、水素原子、ハロゲン原子、または、式Ｇ１、Ｇ２、Ｇ３もしくはＧ４｛Ｒaは、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒbは、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒcは、Ｃ１－Ｃ６鎖式炭化水素基であり、ｚが０、１または２であり、Ｒdが、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒeが、Ｃ１－Ｃ６鎖式炭化水素基である。｝で示される基であり、
　Ｄが－ＣＨ＝であり、
　ｍが０である［項１］記載のヘテロ芳香環化合物。
［項１８］　Ｈｅｔが、窒素原子、および硫黄原子からなる群より選ばれる１個以上のヘテロ原子を含む５員へテロ芳香環であり（ここで、ＡおよびＱはそれぞれ、該５員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５員へテロ芳香環上で互いに隣接することはない。該５員へテロ芳香環は、Ａ及びＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝および－Ｓ－からなる群より選ばれる３個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子である。）、
　Ｊが、式Ｊ１（Ｒ1およびＲ2が、同一または相異なり、Ｃ１－Ｃ３アルキル基であり、Ｒ3が、Ｃ１－Ｃ６鎖式炭化水素基である。）で示される基であり、
　Ｌが、単結合またはＣ１－Ｃ３アルキレン基であり、
　Ａが単結合であり、
　Ｑが式Ｑ１（ＲxおよびＲyが、水素原子である。）で示される基であり、
　Ｇが、水素原子、ハロゲン原子、または、式Ｇ２もしくはＧ３｛Ｒbは、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒcは、Ｃ１－Ｃ６鎖式炭化水素基であり、ｚが０である。｝で示される基であり、
　Ｄが－ＣＨ＝であり、
　ｍが０である［項１］記載のヘテロ芳香環化合物。
［項１９］　［項１］～［項１８］のいずれか一項に記載のヘテロ芳香環化合物と不活性担体とを含有する有害生物防除剤。
［項２０］　有害生物を防除するための［項１］～［項１８］のいずれか一項に記載のヘテロ芳香環化合物の使用。
［項２１］　［項１］～［項１８］のいずれか一項に記載のヘテロ芳香環化合物の有効量を有害生物又は有害生物の生息場所に施用する工程を含む有害生物の防除方法。 (Where
One of Y 1 , Y 2 and Y 3 represents —O—, —S— or —NE 2 —, and the other two are the same or different and represent —CE 1 ═ or —N═. Represent,
Z 1 , Z 2 and Z 3 are the same or different and represent —CE 1 ═ or —N═. )
The heteroaromatic ring compound according to [Item 1], which is a group represented by:
[Item 6] The heteroaromatic ring compound according to [Item 5], wherein Het is a group represented by the formula H3.
[Claim 7] The heteroaromatic ring compound according to [Claim 6], wherein one of Y 1 , Y 2 and Y 3 is —S—.
[Claim 8] The heteroaromatic ring compound according to [Claim 7], wherein one of Y 1 , Y 2 and Y 3 is —S—, and the others are the same or different and —CE 1 ═.
[Item 9] The heteroaromatic ring compound according to [Item 7], wherein Y 1 is —S—.
[Claim 10] The heteroaromatic ring compound according to [Claim 9], wherein Y 1 is -S-, Y 2 and Y 3 are the same or different, and -CE 1 =.
[Item 11] The heteroaromatic ring compound according to [Item 5], wherein Het is a group represented by the formula H4.
[Term 12] Z 1 is -N =, Z 2 is -CE 1 = and Z 3 is -CE 1 = or -N =, or Z 1 is -CE 1 = The heteroaromatic ring compound according to [11], wherein Z 2 is —N═, and Z 3 is —CE 1 ═.
[Item 13] Z 1 is -N = and Z 2 and Z 3 are the same or different -CE 1 =, or Z 2 is -N = and Z 1 and Z 3 are the same or The heteroaromatic ring compound according to Item 12, wherein -CE 1 = is different.
[Item 14] The heteroaromatic ring compound according to [Item 5], wherein Het is a group represented by the formula H5.
[Item 15] Z 1 is -N =, Z 2 is -CE 1 =, and Z 3 is -CE 1 = or -N =, or Z 1 is -CE 1 = The heteroaromatic ring compound according to Item 14, wherein Z 2 is —N═ and Z 3 is —CE 1 ═.
[Item 16] Z 1 is —N═ and Z 2 and Z 3 are the same or different —CE 1 ═, or Z 2 is —N = and Z 1 and Z 3 are the same or The heteroaromatic ring compound according to Item 15, wherein -CE 1 = is different.
[Item 17] Het is a 5- or 6-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom (wherein A and Q are each 5 or An atom to which A is bonded and an atom to which Q is bonded are not adjacent to each other on the 5- or 6-membered heteroaromatic ring, bonded to a carbon atom or a nitrogen atom constituting the 6-membered heteroaromatic ring. The 5- or 6-membered heteroaromatic ring is composed of 3 or 4 atoms or groups selected from the group consisting of —CE 1 ═, —N═ and —S— together with atoms to which A and Q are bonded. 1 is a C1-C2 alkyl group optionally having one or more halogen atoms, a hydrogen atom or a halogen atom).
J is the formula J1 or J2 (R 1 and R 2 are the same or different and are a C1-C3 alkyl group, R 3 is a C1-C6 chain hydrocarbon group, and R 4 and R 5 are The same or different, a C1-C3 alkyl group, and R 6 is a C1-C6 chain hydrocarbon group).
L is a single bond or a C1-C3 alkylene group,
A is a single bond,
Q is a group represented by the formula Q1 (R x and R y are hydrogen atoms),
G is a hydrogen atom, a halogen atom, or a formula G1, G2, G3 or G4 {R a is a C1-C6 chain hydrocarbon group, R b is a C1-C6 chain hydrocarbon group; R c is a C1-C6 chain hydrocarbon group, z is 0, 1 or 2, R d is a C1-C6 chain hydrocarbon group, and R e is a C1-C6 chain hydrocarbon group. It is a hydrogen group. }, And
D is -CH =
The heteroaromatic ring compound according to [Item 1], wherein m is 0.
[Item 18] Het is a 5-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom (wherein A and Q are each a 5-membered heteroaromatic ring). An atom bonded to carbon atom or nitrogen atom constituting an aromatic ring, and an atom bonded to A and an atom bonded to Q are not adjacent to each other on the 5-membered heteroaromatic ring. Is composed of three atoms or groups selected from the group consisting of —CE 1 ═, —N═ and —S— together with atoms to which A and Q are bonded, and E 1 has one or more halogen atoms. An optionally substituted C1-C2 alkyl group, a hydrogen atom or a halogen atom).
J is a group represented by the formula J1 (wherein R 1 and R 2 are the same or different and are a C1-C3 alkyl group and R 3 is a C1-C6 chain hydrocarbon group);
L is a single bond or a C1-C3 alkylene group,
A is a single bond,
Q is a group represented by the formula Q1 (R x and R y are hydrogen atoms),
G is a hydrogen atom, a halogen atom, or a formula G2 or G3 {R b is a C1-C6 chain hydrocarbon group, R c is a C1-C6 chain hydrocarbon group, and z is 0 is there. }, And
D is -CH =
The heteroaromatic ring compound according to [Item 1], wherein m is 0.
[Item 19] A pest control agent comprising the heteroaromatic ring compound according to any one of [Item 1] to [Item 18] and an inert carrier.
[Item 20] Use of the heteroaromatic ring compound according to any one of [Item 1] to [Item 18] for controlling pests.
[Item 21] A method for controlling pests comprising a step of applying an effective amount of the heteroaromatic ring compound according to any one of items [1] to [18] to a pest or a habitat of the pest.
　本発明化合物は、有害生物の防除に有用である。 The compound of the present invention is useful for controlling pests.
　本明細書において用いられる用語について、以下に例を挙げて説明する。 The terms used in this specification will be described below with examples.
　本発明化合物において「ハロゲン原子」とはフッ素原子、塩素原子、臭素原子およびヨウ素原子を意味する。 In the compound of the present invention, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
　本発明化合物において、Ｅ１で表される「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基」としては、例えばメチル基、エチル基、トリフルオロメチル基、およびジフルオロメチル基等が挙げられる。 In the compound of the present invention, examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” represented by E 1 include a methyl group, an ethyl group, a trifluoromethyl group, and a difluoromethyl group. Etc.
　本発明化合物において、Ｅ２で表される「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基」としては、例えばメチル基、エチル基、２，２，２－トリフルオロエチル基、および２，２－ジフルオロエチル基等が挙げられる。 In the compounds of the present invention, examples of the “C1-C2 alkyl group optionally having one or more halogen atoms” represented by E 2 include a methyl group, an ethyl group, and 2,2,2-trifluoroethyl. Group, and a 2,2-difluoroethyl group.
　本発明化合物において「Ｃ１－Ｃ３アルキル基」としては、メチル基、エチル基、プロピル基およびイソプロピル基が挙げられる。 In the compound of the present invention, examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ３アルキル基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基およびトリフルオロメチル基が挙げられる。 In the compound of the present invention, examples of the “C1-C3 alkyl group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a trifluoromethyl group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ペンチル基、ヘキシル基およびトリフルオロメチル基が挙げられる。 Examples of the “C1-C6 alkyl group optionally having one or more halogen atoms” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a sec-butyl group. , Tert-butyl group, pentyl group, hexyl group and trifluoromethyl group.
　本発明化合物において「Ｃ１－Ｃ６鎖式炭化水素基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ペンチル基、２，２－ジメチルプロピル基、３－メチルブチル基、２，３－ジメチルブチル基、３，３－ジメチルブチル基およびヘキシル基等のＣ１－Ｃ６アルキル基；
ビニル基、１－プロペニル基、２－プロペニル基、イソプロペニル基、２－メチル－１－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－ペンテニル基および１－ヘキセニル基等のＣ２－Ｃ６アルケニル基；並びに
エチニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、３，３－ジメチル－１－ブチニル基、１－ペンチニル基および１－ヘキシニル基等のＣ２－Ｃ６アルキニル基が挙げられる。 In the compounds of the present invention, examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 2 , C1-C6 alkyl groups such as 2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group and hexyl group;
Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group C2-C6 alkenyl group such as ethynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3,3-dimethyl-1-butynyl group, 1-pentynyl group and 1-hexynyl group And C2-C6 alkynyl groups such as
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６鎖式炭化水素基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、ペンチル基、２，２－ジメチルプロピル基、３－メチルブチル基、２，３－ジメチルブチル基、３，３－ジメチルブチル基ヘキシル基およびトリフルオロメチル基等の１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基；
ビニル基、１－プロペニル基、２－プロペニル基、イソプロペニル基、２－メチル－１－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－ペンテニル基および１－ヘキセニル基等のＣ２－Ｃ６アルケニル基および２，２－ジフルオロビニル基等の１個以上のハロゲン原子を有していてもよいＣ２－Ｃ６アルケニル基；並びに
エチニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、３，３－ジメチル－１－ブチニル基、１－ペンチニル基、１－ヘキシニル基および２－クロロエチニル基等の１個以上のハロゲン原子を有していてもよいＣ２－Ｃ６アルキニル基が挙げられる。 Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, sec 1 such as -butyl group, tert-butyl group, pentyl group, 2,2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group hexyl group and trifluoromethyl group A C1-C6 alkyl group optionally having one or more halogen atoms;
Vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group and 1-hexenyl group A C2-C6 alkenyl group optionally having one or more halogen atoms such as a C2-C6 alkenyl group such as 2,2-difluorovinyl group, etc .; and an ethynyl group, a propargyl group, a 1-butynyl group, 2- C2 which may have one or more halogen atoms such as butynyl group, 3-butynyl group, 3,3-dimethyl-1-butynyl group, 1-pentynyl group, 1-hexynyl group and 2-chloroethynyl group -C6 alkynyl group can be mentioned.
　本発明化合物において「＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、トリフルオロメチル基、２，２，２－トリフルオロエチル基、シアノメチル基およびシクロプロピルメチル基等の＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６アルキル基；
２－プロペニル基等の＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ２－Ｃ６アルケニル基；並びに
プロパルギル基および２－ブチニル基等の＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ２－Ｃ６アルキニル基が挙げられる。 In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <group α>” include a methyl group, an ethyl group, a propyl group, and an isopropyl group. 1 selected from <Group α> such as butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl and cyclopropylmethyl A C1-C6 alkyl group optionally having one or more atoms or groups;
A C2-C6 alkenyl group optionally having one or more atoms or groups selected from <Group α> such as 2-propenyl group; and selected from <Group α> such as propargyl group and 2-butynyl group Examples include C2-C6 alkynyl group which may have one or more atoms or groups.
　本発明化合物において「＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基等のＣ１－Ｃ６アルキル基；
トリフルオロメチル基、シアノメチル基、シクロプロピルメチル基、メトキシメチル基、エトキシメチル基、１－メトキシエチル基およびメチルチオメチル基等の＜群β＞より選ばれる１個以上の原子もしくは基を有するＣ１－Ｃ６アルキル基；
ビニル基、イソプロペニル基、１－プロペニル基、２－メチル－１－プロペニル基、２，２－ジクロロビニル基および２，２－ジフルオロビニル基等の＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ２－Ｃ６アルケニル基；並びに
エチニル基、１－プロピニル基、２－クロロエチニル基、２－フルオロエチニル基および２－（トリメチルシリル）エチニル基等の＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ２－Ｃ６アルキニル基が挙げられる。 In the compounds of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <group β>” include a methyl group, an ethyl group, a propyl group, and an isopropyl group. A C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group, tert-butyl group;
C1- having one or more atoms or groups selected from <Group β> such as trifluoromethyl group, cyanomethyl group, cyclopropylmethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group and methylthiomethyl group A C6 alkyl group;
One or more atoms selected from <Group β> such as vinyl group, isopropenyl group, 1-propenyl group, 2-methyl-1-propenyl group, 2,2-dichlorovinyl group and 2,2-difluorovinyl group Or a C2-C6 alkenyl group which may have a group; and <Group β> such as an ethynyl group, a 1-propynyl group, a 2-chloroethynyl group, a 2-fluoroethynyl group and a 2- (trimethylsilyl) ethynyl group And C2-C6 alkynyl group which may have one or more selected atoms or groups.
　本発明化合物において「＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基およびｔｅｒｔ－ブチル基等のＣ１－Ｃ６アルキル基；
ジフルオロメチル基、トリフルオロメチル基、２－フルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，１－トリフルオロ－２－プロピル基、シアノメチル基、１－シアノエチル基、シクロプロピルメチル基、１－（シクロプロピル）エチル基、メトキシメチル基、エトキシメチル基、１－メトキシエチル基、２－メトキシエチル基、メチルチオメチル基、メチルスルフィニルメチル基、メチルスルホニルメチル基、２－（メチルチオ）エチル基、２－（メチルスルフィニル）エチル基、２－（メチルスルホニル）エチル基、２－（メチルアミノ）エチル基、２－（ジメチルアミノ）エチル基、ベンジル基、４－メトキシベンジル基、３，４－ジメトキシベンジル基および４－ニトロベンジル基等の＜群γ＞より選ばれる１個以上の原子もしくは基を有するＣ１－Ｃ６アルキル基；
２－プロペニル基、２－ブテニル基および３－メチル－２－ブテニル基等の＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ３－Ｃ６アルケニル基；並びに
プロパルギル基、２－ブチニル基および３－ブチニル基等の＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ２－Ｃ６アルキニル基が挙げられる。 In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <group γ>” include a methyl group, an ethyl group, a propyl group, and an isopropyl group. A C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group and tert-butyl group;
Difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,1-trifluoro-2-propyl group, cyanomethyl group 1-cyanoethyl group, cyclopropylmethyl group, 1- (cyclopropyl) ethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, methylthiomethyl group, methylsulfinylmethyl group, methyl Sulfonylmethyl group, 2- (methylthio) ethyl group, 2- (methylsulfinyl) ethyl group, 2- (methylsulfonyl) ethyl group, 2- (methylamino) ethyl group, 2- (dimethylamino) ethyl group, benzyl group 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-nitrobenzyl group, etc. C1-C6 alkyl group having one or more atoms or groups selected from <group gamma>;
A C3-C6 alkenyl group optionally having one or more atoms or groups selected from <Group γ> such as a 2-propenyl group, a 2-butenyl group and a 3-methyl-2-butenyl group; and a propargyl group And a C2-C6 alkynyl group which may have one or more atoms or groups selected from <Group γ> such as 2-butynyl group and 3-butynyl group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ３アルキレン基」としては、例えば－ＣＨ2－、－ＣＨＣｌ－、－ＣＨＦ－、－ＣＦ2－、－ＣＨ2ＣＨ2－および－ＣＨ2ＣＨ2ＣＨ2－が挙げられる。 Examples of the “C1-C3 alkylene group optionally having one or more halogen atoms” in the compounds of the present invention include —CH 2 —, —CHCl—, —CHF—, —CF 2 —, —CH 2 CH 2 -and -CH 2 CH 2 CH 2 -are mentioned.
　本発明化合物において「Ｃ３－Ｃ９トリアルキルシリル基」は、アルキル部分の炭素の総数が３～９のトリアルキルシリル基を意味し、各アルキル基は同一または異なっていてもよく、例えばトリメチルシリル基、ｔｅｒｔ－ブチルジメチルシリル基、トリエチルシリル基、イソプロピルジメチルシリル基、トリイソプロピルシリル基が挙げられる。 In the compound of the present invention, “C3-C9 trialkylsilyl group” means a trialkylsilyl group having 3 to 9 carbon atoms in the alkyl portion, and each alkyl group may be the same or different. Examples thereof include a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, and a triisopropylsilyl group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基」としては、例えばメトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、ｓｅｃ－ブトキシ基、ｔｅｒｔ－ブトキシ基、２，２，２－トリクロロエトキシ基および２，２，２－トリフルオロエトキシが挙げられる。 Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group. Group, tert-butoxy group, 2,2,2-trichloroethoxy group and 2,2,2-trifluoroethoxy group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキルアミノ基」としては、例えばメチルアミノ基、エチルアミノ基、プロピルアミノ基、イソプロピルアミノ基、ブチルアミノ基、イソブチルアミノ基、ｓｅｃ－ブチルアミノ基、ｔｅｒｔ－ブチルアミノ基および２，２，２－トリフルオロエチルアミノ基が挙げられる。 In the compounds of the present invention, examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” include, for example, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutyl An amino group, a sec-butylamino group, a tert-butylamino group and a 2,2,2-trifluoroethylamino group can be mentioned.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ２－Ｃ１２ジアルキルアミノ基」は、アルキル部分の炭素の総数が２～１２である１個以上のハロゲン原子を有していてもよいジアルキルアミノ基を意味し、各アルキル基は同一または異なっていてもよく、例えばＮ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ，Ｎ－ジブチルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－ｔｅｒｔ－ブチル－Ｎ－メチルアミノ基およびＮ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基が挙げられる。 In the compound of the present invention, the “C2-C12 dialkylamino group optionally having one or more halogen atoms” has one or more halogen atoms having 2 to 12 carbon atoms in the alkyl part. Each alkyl group may be the same or different, for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N— Dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methylamino group and N-methyl- N- (2,2,2-trifluoroethyl) amino group may be mentioned.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルコキシ基」としては、例えばメトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、ｓｅｃ－ブトキシ基、ｔｅｒｔ－ブトキシ基および２，２，２－トリフルオロエトキシ基が挙げられる。 Examples of the “C1-C4 alkoxy group optionally having one or more halogen atoms” in the compounds of the present invention include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a sec-butoxy group. Group, tert-butoxy group and 2,2,2-trifluoroethoxy group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルチオ基」としては、例えばメチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、ブチルチオ基、イソブチルチオ基、ｓｅｃ－ブチルチオ基、ｔｅｒｔ－ブチルチオ基および２，２，２－トリフルオロエチルチオ基が挙げられる。 In the compound of the present invention, examples of the “C1-C4 alkylthio group optionally having one or more halogen atoms” include, for example, methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec- Examples thereof include a butylthio group, a tert-butylthio group and a 2,2,2-trifluoroethylthio group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルフィニル基」としては、例えばメチルスルフィニル基、エチルスルフィニル基、プロピルスルフィニル基、イソプロピルスルフィニル基、ブチルスルフィニル基、イソブチルスルフィニル基、ｓｅｃ－ブチルスルフィニル基、ｔｅｒｔ－ブチルスルフィニル基および２，２，２－トリフルオロエチルスルフィニル基が挙げられる。 Examples of the “C1-C4 alkylsulfinyl group optionally having one or more halogen atoms” in the compounds of the present invention include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutyl group. Examples thereof include a sulfinyl group, a sec-butylsulfinyl group, a tert-butylsulfinyl group, and a 2,2,2-trifluoroethylsulfinyl group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルホニル基」としては、例えばメチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、イソプロピルスルホニル基、ブチルスルホニル基、イソブチルスルホニル基、ｓｅｃ－ブチルスルホニル基、ｔｅｒｔ－ブチルスルホニル基および２，２，２－トリフルオロエチルスルホニル基が挙げられる。 In the compound of the present invention, examples of the “C1-C4 alkylsulfonyl group optionally having one or more halogen atoms” include, for example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutyl Examples include a sulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, and a 2,2,2-trifluoroethylsulfonyl group.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルアミノ基」としては、例えばメチルアミノ基、エチルアミノ基、プロピルアミノ基、イソプロピルアミノ基、ブチルアミノ基、イソブチルアミノ基、ｓｅｃ－ブチルアミノ基、ｔｅｒｔ－ブチルアミノ基および２，２，２－トリフルオロエチルアミノ基が挙げられる。 In the compounds of the present invention, examples of the “C1-C4 alkylamino group optionally having one or more halogen atoms” include, for example, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutyl An amino group, a sec-butylamino group, a tert-butylamino group and a 2,2,2-trifluoroethylamino group can be mentioned.
　本発明化合物において「１個以上のハロゲン原子を有していてもよいＣ２－Ｃ８ジアルキルアミノ基」は、アルキル部分の炭素の総数が２～８である１個以上のハロゲン原子を有していてもよいジアルキルアミノ基を意味し、各アルキル基は同一または異なっていてもよく、例えばＮ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ，Ｎ－ジブチルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－ｔｅｒｔ－ブチル－Ｎ－メチルアミノ基およびＮ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基が挙げられる。 In the compound of the present invention, the “C2-C8 dialkylamino group optionally having one or more halogen atoms” has one or more halogen atoms having 2 to 8 carbon atoms in the alkyl part. Each alkyl group may be the same or different, for example, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N— Dibutylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-tert-butyl-N-methylamino group and N-methyl- N- (2,2,2-trifluoroethyl) amino group may be mentioned.
　本発明化合物において「フェニル基（該フェニル基は、メチル基、メトキシ基、塩素原子およびニトロ基からなる群より選ばれる１個以上の基を有してもよい。）」は、メチル基、メトキシ基、塩素原子およびニトロ基からなる群から独立して選択される１以上の置換基で置換されていてもよいフェニル基を表し、例えばフェニル基、４－メトキシフェニル基、３，４－ジメトキシフェニル基、４－ニトロフェニル基、２－ニトロフェニル基、４－クロロフェニル基、２－クロロフェニル基、２，６－ジクロロフェニル基および４－メチルフェニル基が挙げられる。 In the compound of the present invention, “phenyl group (the phenyl group may have one or more groups selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group”) means a methyl group, a methoxy group, Represents a phenyl group which may be substituted with one or more substituents independently selected from the group consisting of a group, a chlorine atom and a nitro group, such as a phenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl Groups, 4-nitrophenyl group, 2-nitrophenyl group, 4-chlorophenyl group, 2-chlorophenyl group, 2,6-dichlorophenyl group and 4-methylphenyl group.
　本発明化合物において、Ｈｅｔは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる１個以上（特に１～４個）のヘテロ原子を含む５または６員へテロ芳香環を表す。ここで、ＡおよびＱはそれぞれ、該５または６員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５または６員へテロ芳香環上で互いに隣接することはない。 In the compounds of the present invention, Het represents a 5- or 6-membered heteroaromatic ring containing one or more (particularly 1 to 4) heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. Here, A and Q are bonded to the carbon atom or nitrogen atom constituting the 5- or 6-membered heteroaromatic ring, respectively, and the atom to which A is bonded to the atom to which Q is bonded They are not adjacent to each other on the aromatic ring.
　具体的には、下図で示すように、Ｈｅｔが該６員へテロ芳香環の場合には、ＡおよびＱが１，３位または１，４位の関係にあって１，２位の関係にはなく、また、Ｈｅｔが該５員へテロ芳香環の場合にＡおよびＱが１，３位の関係にあって１，２位の関係にはないことを意味する。 Specifically, as shown in the figure below, when Het is the 6-membered heteroaromatic ring, A and Q are in the 1,3-position or 1,4-position, and in the 1,2-position. It also means that when Het is the 5-membered heteroaromatic ring, A and Q are in the 1,3-position and not in the 1,2-position.
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
（式中、ＡおよびＱはは前記と同じ意味を表す。）
　Ｈｅｔで表される５または６員へテロ芳香環は、ＡおよびＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝、－Ｏ－、－Ｓ－および－ＮＥ２－からなる群より選ばれる３もしくは４個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子を表し、Ｅ２は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基を表す。）、
　本発明化合物において、Ｈｅｔで表される前記５または６員へテロ芳香環が－ＣＥ１＝を２個以上含む場合に、各Ｅ１基は同一でも相異なっていてもよい。 (In the formula, A and Q have the same meaning as described above.)
The 5- or 6-membered heteroaromatic ring represented by Het is selected from the group consisting of —CE 1 ═, —N═, —O—, —S— and —NE 2 — together with the atoms to which A and Q are bonded. E 1 represents a C1-C2 alkyl group which may have one or more halogen atoms, a hydrogen atom or a halogen atom, and E 2 represents one or more atoms or groups. A C1-C2 alkyl group which may have a halogen atom is represented. ),
In the compound of the present invention, when the 5- or 6-membered heteroaromatic ring represented by Het contains two or more —CE 1 ═, each E 1 group may be the same or different.
　本発明化合物において、Ｈｅｔで表される前記６員へテロ芳香環としては、式Ｈ１およびＨ２で示される環が挙げられる。以下、構造式の左側の「・」印がＡと結合する位置を表し、構造式の右側の「・」印がＱと結合する位置を表す。 In the compound of the present invention, examples of the 6-membered heteroaromatic ring represented by Het include rings represented by the formulas H1 and H2. In the following, the “•” mark on the left side of the structural formula represents the position where it is combined with A, and the “•” mark on the right side of the structural formula represents the position where it is combined with Q.
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
（式中、Ｘ１、Ｘ２、Ｘ３およびＸ４は前記と同じ意味を表す。）
　本発明化合物における６員へテロ芳香環の具体例を以下に示す。 (Wherein X 1 , X 2 , X 3 and X 4 represent the same meaning as described above.)
Specific examples of the 6-membered heteroaromatic ring in the compound of the present invention are shown below.
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
（式中、Ｅ１は前記と同じ意味を表す。）
　本発明化合物において、Ｈｅｔで表される５員へテロ芳香環としては、式Ｈ３、Ｈ４およびＨ５で示される環が挙げられる。 (Wherein E 1 represents the same meaning as described above.)
In the compound of the present invention, examples of the 5-membered heteroaromatic ring represented by Het include rings represented by the formulas H3, H4 and H5.
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
（式中、Ｙ１、Ｙ２、Ｙ３、Ｚ１、Ｚ２およびＺ３は前記と同じ意味を表す。）
　式Ｈ３における環の内側の“○”の表記は、５員へテロ芳香環を構成する２つの二重結合と２つの一重結合の配置として、下記に示す３つの配置を全て含んでいることを示している。 (Wherein Y 1 , Y 2 , Y 3 , Z 1 , Z 2 and Z 3 represent the same meaning as described above.)
The notation “◯” inside the ring in Formula H3 indicates that the arrangement of two double bonds and two single bonds constituting a 5-membered heteroaromatic ring includes all three arrangements shown below. Show.
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
（式中、Ｙ１、Ｙ２及びＹ３は前記と同じ意味を表す。 (Wherein Y 1 , Y 2 and Y 3 represent the same meaning as described above.
　本発明化合物において、式Ｈ３で表される５員へテロ芳香環の具体例を以下に示す。 Specific examples of the 5-membered heteroaromatic ring represented by the formula H3 in the compound of the present invention are shown below.
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
（式中、Ｅ１及びＥ２は前記と同じ意味を表す。）
　本発明化合物において、式Ｈ４で表される５員へテロ芳香環の具体例を以下に示す。 (In the formula, E 1 and E 2 represent the same meaning as described above.)
Specific examples of the 5-membered heteroaromatic ring represented by the formula H4 in the compound of the present invention are shown below.
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
（式中、Ｅ１は前記と同じ意味を表す。）
　本発明化合物において、式Ｈ５で表される５員へテロ芳香環の具体例を以下に示す。 (Wherein E 1 represents the same meaning as described above.)
Specific examples of the 5-membered heteroaromatic ring represented by the formula H5 in the compound of the present invention are shown below.
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
（式中、Ｅ１は前記と同じ意味を表す。）
　本発明化合物としては、例えば以下のヘテロ芳香環化合物が挙げられる。
［態様Ａ］
　式（１）において、Ｈｅｔが式Ｈ１またはＨ２で表される６員へテロ芳香環である化合物。
［態様Ｂ］
　式（１）において、Ｈｅｔが式Ｈ１またはＨ２で示される環であり、Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの１つまたは２つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様Ｃ］
　式（１）において、Ｈｅｔが式Ｈ１またはＨ２で示される環であり、Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの１つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様Ｄ］
　式（１）において、Ｈｅｔが式Ｈ１で示される環であり、Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの１つまたは２つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様Ｅ］
　式（１）において、Ｈｅｔが式Ｈ１で示される環であり、Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの１つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様Ｆ］
　式（１）において、Ｈｅｔが式Ｈ１で示される環であり、Ｘ１またはＸ２のいずれか一方が－Ｎ＝であり、他方が－ＣＥ１＝または－Ｎ＝であり、Ｘ３およびＸ４が－ＣＥ１＝である化合物。
［態様Ｇ］
　式（１）において、Ｈｅｔが式Ｈ１で示される環であり、Ｘ１が－Ｎ＝であり、Ｘ２、Ｘ３およびＸ４が－ＣＥ１＝である化合物。
［態様Ｈ］
　式（１）において、Ｈｅｔが式Ｈ１で示される環であり、Ｘ２が－Ｎ＝であり、Ｘ１、Ｘ３およびＸ４が－ＣＥ１＝である化合物。
［態様Ｉ］
　式（１）において、Ｈｅｔが式Ｈ３、Ｈ４またはＨ５で表される５員へテロ芳香環である化合物。
［態様Ｊ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環である化合物。
［態様Ｋ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１、Ｙ２およびＹ３のうちの１つが－Ｏ－または－Ｓ－である化合物。
［態様Ｌ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１、Ｙ２およびＹ３のうちの１つが－Ｓ－である化合物。
［態様Ｍ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１が－Ｏ－、－Ｓ－または－ＮＥ２－である化合物。
［態様Ｎ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１が－Ｏ－または－Ｓ－である化合物。
［態様Ｏ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１が－Ｓ－である化合物。
［態様Ｐ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１が－Ｓ－であり、Ｙ２およびＹ３のいずれか一方が－ＣＥ１＝であり、他方がＣＥ１＝または－Ｎ＝である化合物。
［態様Ｑ］
　式（１）において、Ｈｅｔが式Ｈ３で示される環であり、Ｙ１が－Ｓ－であり、Ｙ２およびＹ３が－ＣＥ１＝である化合物。
［態様Ｒ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環である化合物。
［態様Ｓ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ１、Ｚ２およびＺ３のうちの１つまたは２つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様Ｔ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ１、Ｚ２およびＺ３のうちの１つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様Ｕ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、かつ、Ｚ３が－ＣＥ１＝または－Ｎ＝であるか、あるいは、Ｚ１が－ＣＥ１＝であり、Ｚ２が－Ｎ＝であり、かつ、Ｚ３が－ＣＥ１＝である化合物。
［態様Ｖ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、Ｚ３が－ＣＥ１＝または－Ｎ＝である化合物。
［態様Ｗ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ１およびＺ２のいずれか一方が－Ｎ＝であり、他方が－ＣＥ１＝であり、Ｚ３が－ＣＥ１＝である化合物。
［態様Ｘ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ１が－Ｎ＝であり、Ｚ２およびＺ３がＣＥ１＝である化合物。
［態様Ｙ］
　式（１）において、Ｈｅｔが式Ｈ４で示される環であり、Ｚ２が－Ｎ＝であり、Ｚ１およびＺ３がＣＥ１＝である化合物。
［態様Ｚ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環である化合物。
［態様ＡＡ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ１、Ｚ２およびＺ３のうちの１つまたは２つが－Ｎ＝であり、それ以外が－ＣＥ１＝であ化合物。
［態様ＡＢ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ１、Ｚ２およびＺ３のうちの１つが－Ｎ＝であり、それ以外が－ＣＥ１＝である化合物。
［態様ＡＣ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、かつ、Ｚ３が－ＣＥ１＝または－Ｎ＝であるか、あるいは、Ｚ１が－ＣＥ１＝であり、Ｚ２が－Ｎ＝であり、かつ、Ｚ３が－ＣＥ１＝である化合物。
［態様ＡＤ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、Ｚ３が－ＣＥ１＝または－Ｎ＝である化合物。
［態様ＡＥ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ１およびＺ２のいずれか一方が－Ｎ＝であり、他方が－ＣＥ１＝であり、Ｚ３が－ＣＥ１＝である化合物。
［態様ＡＦ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ１が－Ｎ＝であり、Ｚ２およびＺ３がＣＥ１＝である化合物。
［態様ＡＧ］
　式（１）において、Ｈｅｔが式Ｈ５で示される環であり、Ｚ２が－Ｎ＝であり、Ｚ１およびＺ３がＣＥ１＝である化合物。
［態様ＡＨ］
　下式で示される［項１］記載のヘテロ芳香環化合物。 (Wherein E 1 represents the same meaning as described above.)
As this invention compound, the following hetero aromatic ring compounds are mentioned, for example.
[Aspect A]
In the formula (1), compounds wherein Het is a 6-membered heteroaromatic ring represented by formula H1 or H2.
[Aspect B]
In the formula (1), Het is a ring represented by the formula H1 or H2, one or two of X 1 , X 2 , X 3 and X 4 are —N═, and the others are —CE 1 A compound where =.
[Aspect C]
In the formula (1), Het is a ring represented by the formula H1 or H2, one of X 1 , X 2 , X 3 and X 4 is —N═, and the other is —CE 1 ═ Compound.
[Aspect D]
In the formula (1), Het is a ring represented by the formula H1, one or two of X 1 , X 2 , X 3 and X 4 are —N═, and the others are —CE 1 = A compound.
[Aspect E]
In the formula (1), compounds wherein Het is a ring represented by the formula H1, one of X 1 , X 2 , X 3 and X 4 is —N═ and the other is —CE 1 =.
[Aspect F]
In the formula (1), Het is a ring represented by the formula H1, and either X 1 or X 2 is —N═, the other is —CE 1 ═ or —N═, and X 3 and X 2 A compound wherein 4 is -CE 1 =.
[Aspect G]
In the formula (1), compounds wherein Het is a ring represented by the formula H1, X 1 is —N═, and X 2 , X 3 and X 4 are —CE 1 =.
[Aspect H]
In the formula (1), compounds wherein Het is a ring represented by the formula H1, X 2 is —N═, and X 1 , X 3 and X 4 are —CE 1 =.
[Aspect I]
In the formula (1), compounds wherein Het is a 5-membered heteroaromatic ring represented by the formula H3, H4 or H5.
[Aspect J]
In the formula (1), compounds wherein Het is a ring represented by the formula H3.
[Aspect K]
In the formula (1), compounds wherein Het is a ring represented by the formula H3 and one of Y 1 , Y 2 and Y 3 is —O— or —S—.
[Aspect L]
In the formula (1), compounds wherein Het is a ring represented by the formula H3 and one of Y 1 , Y 2 and Y 3 is —S—.
[Aspect M]
In the formula (1), compounds wherein Het is a ring represented by the formula H3 and Y 1 is —O—, —S— or —NE 2 —.
[Aspect N]
In the formula (1), compounds wherein Het is a ring represented by the formula H3 and Y 1 is —O— or —S—.
[Aspect O]
In the formula (1), compounds wherein Het is a ring represented by the formula H3 and Y 1 is —S—.
[Aspect P]
In the formula (1), Het is a ring represented by the formula H3, Y 1 is -S-, one of Y 2 and Y 3 is -CE 1 =, and the other is CE 1 = or- A compound where N =.
[Aspect Q]
In the formula (1), compounds wherein Het is a ring represented by the formula H3, Y 1 is —S—, and Y 2 and Y 3 are —CE 1 ═.
[Aspect R]
In the formula (1), compounds wherein Het is a ring represented by the formula H4.
[Aspect S]
In the formula (1), compounds wherein Het is a ring represented by the formula H4, one or two of Z 1 , Z 2 and Z 3 are —N═, and the others are —CE 1 ═.
[Aspect T]
In the formula (1), compounds wherein Het is a ring represented by the formula H4, one of Z 1 , Z 2 and Z 3 is —N═, and the other is —CE 1 =.
[Aspect U]
In the formula (1), Het is a ring represented by the formula H4, Z 1 is -N =, Z 2 is -CE 1 =, and Z 3 is -CE 1 = or -N = Or a compound wherein Z 1 is —CE 1 ═, Z 2 is —N═ and Z 3 is —CE 1 ═.
[Aspect V]
In the formula (1), compounds wherein Het is the ring represented by the formula H4, Z 1 is —N═, Z 2 is —CE 1 = and Z 3 is —CE 1 ═ or —N═ .
[Aspect W]
In the formula (1), Het is a ring represented by the formula H4, one of Z 1 and Z 2 is —N═, the other is —CE 1 =, and Z 3 is —CE 1 = A compound.
[Aspect X]
In the formula (1), compounds wherein Het is a ring represented by the formula H4, Z 1 is —N═, and Z 2 and Z 3 are CE 1 =.
[Aspect Y]
In the formula (1), compounds wherein Het is a ring represented by the formula H4, Z 2 is —N═ and Z 1 and Z 3 are CE 1 =.
[Aspect Z]
In the formula (1), compounds wherein Het is a ring represented by the formula H5.
[Aspect AA]
In the formula (1), compounds wherein Het is a ring represented by the formula H5, one or two of Z 1 , Z 2 and Z 3 is —N═, and the others are —CE 1 ═.
[Aspect AB]
In the formula (1), compounds wherein Het is a ring represented by the formula H5, one of Z 1 , Z 2 and Z 3 is —N═, and the other is —CE 1 =.
[Aspect AC]
In the formula (1), Het is a ring represented by the formula H5, Z 1 is -N =, Z 2 is -CE 1 =, and Z 3 is -CE 1 = or -N = Or a compound wherein Z 1 is —CE 1 ═, Z 2 is —N═ and Z 3 is —CE 1 ═.
[Aspect AD]
In the formula (1), compounds wherein Het is the ring represented by the formula H5, Z 1 is -N =, Z 2 is -CE 1 = and Z 3 is -CE 1 = or -N = .
[Aspect AE]
In Formula (1), Het is a ring represented by Formula H5, one of Z 1 and Z 2 is —N═, the other is —CE 1 =, and Z 3 is —CE 1 = A compound.
[Aspect AF]
In the formula (1), compounds wherein Het is a ring represented by the formula H5, Z 1 is —N═, and Z 2 and Z 3 are CE 1 =.
[Aspect AG]
In the formula (1), compounds wherein Het is a ring represented by the formula H5, Z 2 is —N═ and Z 1 and Z 3 are CE 1 =.
[Aspect AH]
The heteroaromatic ring compound according to [Item 1] represented by the following formula:
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
（式中、各記号は前記と同じ意味を表す。）
［態様ＡＩ］
　下式で示される［項１］記載のヘテロ芳香環化合物。 (In the formula, each symbol represents the same meaning as described above.)
[Aspect AI]
The heteroaromatic ring compound according to [Item 1] represented by the following formula:
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000024
（式中、各記号は前記と同じ意味を表す。）
　また、本発明化合物としては、例えば以下のヘテロ芳香環化合物も挙げられる。
［態様１］
　式（１）において、Ｑが式Ｑ１で示される基である［項１］、［態様Ａ］～［態様Ｚ］および［態様ＡＡ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。
［態様２］
　式（１）において、Ｑが式Ｑ２、Ｑ３またはＱ４で示される基である［項１］、［態様Ａ］～［態様Ｙ］および［態様ＡＨ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。
［態様３］
　式（１）において、Ｑが式Ｑ２で示される基である［項１］、［態様Ａ］～［態様Ｙ］および［態様ＡＨ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。
［態様４］
　式（１）において、Ｑが式Ｑ３で示される基である［項１］、［態様Ａ］～［態様Ｙ］および［態様ＡＨ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。
［態様５］
　式（１）において、Ｑが式Ｑ４で示される基である［項１］、［態様Ａ］～［態様Ｙ］および［態様ＡＨ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。
［態様６］～［態様１４３］
　式（１）において、ＱとＧとが〔表１〕～〔表６〕の組み合わせである［項１］、［態様Ａ］～［態様Ｙ］および［態様ＡＨ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物；あるいは、式（１）において、ＱとＧとが〔表１〕または〔表２〕の組み合わせである［態様Ｚ］および［態様ＡＡ］～［態様ＡＧ］のいずれかに記載のヘテロ芳香環化合物。 (In the formula, each symbol represents the same meaning as described above.)
Moreover, as this invention compound, the following hetero aromatic ring compounds are also mentioned, for example.
[Aspect 1]
The heteroaromatic ring compound according to any one of [Item 1], [Aspect A] to [Aspect Z], and [Aspect AA] to [Aspect AI], wherein Q is a group represented by Formula Q1 in Formula (1) .
[Aspect 2]
In Formula (1), Q is a group represented by Formula Q2, Q3 or Q4 [Claim 1], [Aspect A] to [Aspect Y] and [Aspect AH] to [Aspect AI] Heteroaromatic compounds.
[Aspect 3]
The heteroaromatic ring compound according to any one of [Item 1], [Aspect A] to [Aspect Y] and [Aspect AH] to [Aspect AI], wherein Q is a group represented by Formula Q2 in Formula (1) .
[Aspect 4]
The heteroaromatic ring compound according to any one of [Item 1], [Aspect A] to [Aspect Y], and [Aspect AH] to [Aspect AI], wherein Q is a group represented by Formula Q3 in Formula (1) .
[Aspect 5]
The heteroaromatic ring compound according to any one of [Item 1], [Aspect A] to [Aspect Y], and [Aspect AH] to [Aspect AI], wherein Q is a group represented by Formula Q4 in Formula (1) .
[Aspect 6] to [Aspect 143]
In Formula (1), any one of [Claim 1], [Aspect A] to [Aspect Y], and [Aspect AH] to [Aspect AI], wherein Q and G are combinations of [Table 1] to [Table 6] Or a heteroaromatic ring compound according to any one of [Aspect Z] and [Aspect AA] to [Aspect AG], wherein in Formula (1), Q and G are a combination of [Table 1] or [Table 2] The heteroaromatic ring compound according to any one of the above.
　なお、例えば、［態様６］は、「式（１）において、Ｑが式Ｑ１、Ｑ２、Ｑ３またはＱ４で示される基であり、Ｇが水素原子、ハロゲン原子、式Ｇ１、Ｇ２、Ｇ３、またはＧ４で示される基である［項１］、［態様Ａ］～［態様Ｚ］および［態様ＡＡ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。」を表し、また、例えば、［態様５２］は、「式（１）において、Ｑが式Ｑ２、Ｑ３またはＱ４で示される基であり、Ｇが水素原子、ハロゲン原子、式Ｇ１、Ｇ２、Ｇ３、またはＧ４で示される基である［項１］、［態様Ａ］～［態様Ｙ］および［態様ＡＨ］～［態様ＡＩ］のいずれかに記載のヘテロ芳香環化合物。」を表す。 For example, [Aspect 6] is “in the formula (1), Q is a group represented by the formulas Q1, Q2, Q3, or Q4, G is a hydrogen atom, a halogen atom, a formula G1, G2, G3, or A heteroaromatic ring compound according to any one of [Aspect 1], [Aspect A] to [Aspect Z] and [Aspect AA] to [Aspect AI], which is a group represented by G4. [Aspect 52] is “in the formula (1), Q is a group represented by the formula Q2, Q3 or Q4, and G is a hydrogen atom, a halogen atom, a group represented by the formula G1, G2, G3 or G4. And [Aspect 1], [Aspect A] to [Aspect Y], and [Aspect AH] to [Aspect AI].
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
　また、本発明化合物として、例えば、以下のヘテロ芳香環化合物も挙げられる。 In addition, examples of the compound of the present invention include the following heteroaromatic ring compounds.
　式（１）において、Ｄが－ＣＨ＝である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｄが－Ｎ＝である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｌが単結合または－ＣＨ2－であり、Ａが単結合または－Ｏ－であり、Ｊが式Ｊ１またはＪ２で示される基である、［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｌが単結合または－ＣＨ2－であり、Ａが単結合または－Ｏ－であり、Ｊが式Ｊ１で示される基（Ｊが式Ｊ１で示される基の場合に、Ｒ1およびＲ2はいずれもメチル基であり、Ｒ3は水素原子、メチル基、またはエチル基である。）または式Ｊ２で示される基（Ｊが式Ｊ２で示される基の場合に、Ｒ4、Ｒ5およびＲ6はいずれもメチル基である。）である、［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｌが単結合であり、Ａが単結合であり、Ｊが式Ｊ１で示される基（Ｊが式Ｊ１で示される基の場合に、Ｒ1およびＲ2はいずれもメチル基であり、Ｒ3は水素原子、メチル基、またはエチル基である。）または式Ｊ２で示される基（Ｊが式Ｊ２で示される基の場合に、Ｒ4、Ｒ5およびＲ6はいずれもメチル基である。）である、［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｊ－Ｌ－Ａがｔｅｒｔ－ブチル基である、［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ１で示される基であり、かつ、ＲxおよびＲyが同一または相異なり＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子であるか、
Ｑが式Ｑ２で示される基であるか、
Ｑが式Ｑ３で示される基であるか、あるいは、
Ｑが式Ｑ４で示される基であり、かつ、Ｒzが＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様６］～［態様２８］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ１で示される基であり、かつ、ＲxおよびＲyが同一または相異なりメチル基または水素原子であるか、
Ｑが式Ｑ２で示される基であるか、
Ｑが式Ｑ３で示される基であり、かつ、ｙが０であるか、あるいは、
Ｑが式Ｑ４で示される基であり、かつ、Ｒzがメチル基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様６］～［態様２８］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ１で示される基であり、かつ、ＲxおよびＲyが同一または相異なり＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］、［態様１］および［態様２９］～［態様５１］のいずれかに記載のヘテロ環化合物；
　式（１）において、Ｑが式Ｑ１で示される基であり、かつ、ＲxおよびＲyが同一または相異なりメチル基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］、［態様１］および［態様２９］～［態様５１］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ２で示される基であるか、
Ｑが式Ｑ３で示される基であるか、あるいは、
Ｑが式Ｑ４で示される基であり、かつ、Ｒzが＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｙ］、［態様ＡＨ］～［態様ＡＩ］、［態様２］および［態様５２］～［態様７４］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ２で示される基であるか、
Ｑが式Ｑ３で示される基であり、かつ、ｙが０であるか、あるいは、
Ｑが式Ｑ４で示される基であり、かつ、Ｒzがメチル基または水素原子である［項１］、［態様Ａ］～［態様Ｙ］、［態様ＡＨ］～［態様ＡＩ］、［態様２］および［態様５２］～［態様７４］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ３で示される基であり、かつ、ｙが０である［項１］、［態様Ａ］～［態様Ｙ］、［態様ＡＨ］～［態様ＡＩ］、［態様４］および［態様９８］～［態様１２０］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ４で示される基であり、かつ、Ｒzが＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｙ］、［態様ＡＨ］～［態様ＡＩ］、［態様５］および［態様１２１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｑが式Ｑ４で示される基であり、かつ、Ｒzがメチル基または水素原子である［項１］、［態様Ａ］～［態様Ｙ］、［態様ＡＨ］～［態様ＡＩ］、［態様５］および［態様１２１］～［態様１４３］のいずれかに記載の化合物；
　式（１）において、Ｇが水素原子またはハロゲン原子であるか、
Ｇが式Ｇ１で示される基であり、かつ、Ｒaが＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、
Ｇが式Ｇ２で示される基であり、かつ、Ｒbが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、
Ｇが式Ｇ３で示される基であり、かつ、Ｒcが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、あるいは、
Ｇが式Ｇ４で示される基であり、Ｒdが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であり、かつ、Ｒeが、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇがハロゲン原子であるか、
Ｇが式Ｇ１で示される基であり、かつ、Ｒaが＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、
Ｇが式Ｇ２で示される基であり、かつ、Ｒbが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、
Ｇが式Ｇ３で示される基であり、かつ、Ｒcが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、あるいは、
Ｇが式Ｇ４で示される基であり、Ｒdが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であり、かつ、Ｒeが、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ１で示される基であり、かつ、Ｒaが＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、
Ｇが式Ｇ２で示される基であり、かつ、Ｒbが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、
Ｇが式Ｇ３で示される基であり、かつ、Ｒcが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、あるいは、
Ｇが式Ｇ４で示される基であり、Ｒdが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であり、かつ、Ｒeが、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、水素原子、フッ素原子、塩素原子、臭素原子、メチル基、エチル基、プロピル基、イソプロピル基、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、２，２，２－トリフルオロエトキシ基、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、２，２，２－トリフルオロエチルチオ基、Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基、Ｎ－メチルアミノ基、Ｎ－エチルアミノ基、Ｎ－プロピルアミノ基、Ｎ－イソプロピルアミノ基またはＮ－（２，２，２－トリフルオロエチル）アミノ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、フッ素原子、塩素原子、臭素原子、メチル基、エチル基、プロピル基、イソプロピル基、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、２，２，２－トリフルオロエトキシ基、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、２，２，２－トリフルオロエチルチオ基、Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基、Ｎ－メチルアミノ基、Ｎ－エチルアミノ基、Ｎ－プロピルアミノ基、Ｎ－イソプロピルアミノ基またはＮ－（２，２，２－トリフルオロエチル）アミノ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、メチル基、エチル基、プロピル基、イソプロピル基、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、２，２，２－トリフルオロエトキシ基、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、２，２，２－トリフルオロエチルチオ基、Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基、Ｎ－メチルアミノ基、Ｎ－エチルアミノ基、Ｎ－プロピルアミノ基、Ｎ－イソプロピルアミノ基またはＮ－（２，２，２－トリフルオロエチル）アミノ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ２で示される基であり、かつ、Ｒbが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、あるいは
Ｇが式Ｇ３で示される基であり、かつ、Ｒcが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＨ］および［態様１］～［態様５］のいずれかに記載のヘテロ環化合物；
　式（１）において、Ｇが、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、２，２，２－トリフルオロエトキシ基、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基または２，２，２－トリフルオロエチルチオ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ１で示される基であり、かつ、Ｒaが＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であるか、あるいは、
Ｇが式Ｇ４で示される基であり、Ｒdが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であり、かつ、Ｒeが、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、メチル基、エチル基、プロピル基、イソプロピル基、Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基、Ｎ－メチルアミノ基、Ｎ－エチルアミノ基、Ｎ－プロピルアミノ基、Ｎ－イソプロピルアミノ基またはＮ－（２，２，２－トリフルオロエチル）アミノ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ１で示される基であり、かつ、Ｒaが＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、メチル基、エチル基、プロピル基またはイソプロピル基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ２で示される基であり、かつ、Ｒbが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基または２，２，２－トリフルオロエトキシ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ３で示される基であり、かつ、Ｒcが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基または２，２，２－トリフルオロエチルチオ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが式Ｇ４で示される基であり、Ｒdが＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基であり、かつ、Ｒeが、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基または水素原子である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物；
　式（１）において、Ｇが、Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－プロピルアミノ基、Ｎ－イソプロピル－Ｎ－メチルアミノ基、Ｎ－メチル－Ｎ－（２，２，２－トリフルオロエチル）アミノ基、Ｎ－メチルアミノ基、Ｎ－エチルアミノ基、Ｎ－プロピルアミノ基、Ｎ－イソプロピルアミノ基またはＮ－（２，２，２－トリフルオロエチル）アミノ基である［項１］、［態様Ａ］～［態様Ｚ］、［態様ＡＡ］～［態様ＡＩ］および［態様１］～［態様５］のいずれかに記載の化合物。 In Formula (1), any one of [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 143] in which D is —CH═ A compound according to
In Formula (1), any one of [Item 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI], and [Aspect 1] to [Aspect 143] in which D is —N═ A compound according to
In the formula (1), L is a single bond or —CH 2 —, A is a single bond or —O—, and J is a group represented by the formula J1 or J2. ] To [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 143];
In the formula (1), L is a single bond or —CH 2 —, A is a single bond or —O—, and J is a group represented by the formula J1 (when J is a group represented by the formula J1, R 1 and R 2 are both methyl groups, and R 3 is a hydrogen atom, a methyl group, or an ethyl group.) Or a group represented by formula J2 (when J is a group represented by formula J2, 4 , R 5 and R 6 are all methyl groups.) [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 1] A compound according to any of aspects 143];
In the formula (1), L is a single bond, A is a single bond, and J is a group represented by the formula J1 (when J is a group represented by the formula J1, R 1 and R 2 are both methyl R 3 is a hydrogen atom, a methyl group, or an ethyl group) or a group represented by the formula J2 (when J is a group represented by the formula J2, any of R 4 , R 5, and R 6 is Is also a methyl group), according to any one of [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 143]. Compound;
In Formula (1), JLA is a tert-butyl group, [Item 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI], and [Aspect 1] to [Aspect 1] A compound according to any of aspects 143];
In the formula (1), Q is a group represented by the formula Q1, and R x and R y may be the same or different and may have one or more atoms or groups selected from <Group α>. A C1-C6 chain hydrocarbon group or a hydrogen atom,
Q is a group represented by formula Q2, or
Q is a group of formula Q3, or
Q is a group represented by formula Q4, and R z is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group α>. [Item 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 6] to [Aspect 28];
In the formula (1), Q is a group represented by the formula Q1, and R x and R y are the same or different and are a methyl group or a hydrogen atom,
Q is a group represented by formula Q2, or
Q is a group represented by formula Q3 and y is 0, or
[Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect], wherein Q is a group represented by formula Q4 and R z is a methyl group or a hydrogen atom 6] to [Aspect 28];
In the formula (1), Q is a group represented by the formula Q1, and R x and R y may be the same or different and may have one or more atoms or groups selected from <Group α>. [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI], [Aspect 1] and [Aspect 29] to [Aspect] which are a C1-C6 chain hydrocarbon group or a hydrogen atom 51];
In the formula (1), Q is a group represented by the formula Q1, and R x and R y are the same or different and are a methyl group or a hydrogen atom [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI], [Aspect 1] and [Aspect 29] to [Aspect 51];
In Formula (1), Q is a group represented by Formula Q2, or
Q is a group of formula Q3, or
Q is a group represented by formula Q4, and R z is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group α>. [Claim 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [Aspect 2] and [Aspect 52] to [Aspect 74];
In Formula (1), Q is a group represented by Formula Q2, or
Q is a group represented by formula Q3 and y is 0, or
[Claim 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [Aspect] wherein Q is a group represented by formula Q4 and R z is a methyl group or a hydrogen atom 2] and the compound according to any one of [Aspect 52] to [Aspect 74];
In the formula (1), Q is a group represented by the formula Q3, and y is 0 [Item 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [ Aspect 4] and a compound according to any one of [Aspect 98] to [Aspect 120];
In the formula (1), Q is a group represented by the formula Q4, and R z may have one or more atoms or groups selected from <Group α>. [Claim 1], [Aspect A] to [Aspect Y], [Aspect AH] to [Aspect AI], [Aspect 5] and [Aspect 121] to [Aspect 143], which are a group or a hydrogen atom A compound of
In the formula (1), Q is a group represented by the formula Q4, and R z is a methyl group or a hydrogen atom [Claim 1], [Aspect A] to [Aspect Y], [Aspect AH] to [ Aspect AI], [Aspect 5] and a compound according to any one of [Aspect 121] to [Aspect 143];
In the formula (1), G is a hydrogen atom or a halogen atom,
G is a group represented by the formula G1, and R a is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group β>,
G is a group represented by the formula G2, and R b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group γ>,
G is a group represented by the formula G3, and R c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, or ,
G is a group represented by the formula G4, R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, and R e Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from <Group γ> [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
In Formula (1), G is a halogen atom,
G is a group represented by the formula G1, and R a is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group β>,
G is a group represented by the formula G2, and R b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group γ>,
G is a group represented by the formula G3, and R c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, or ,
G is a group represented by the formula G4, R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, and R e Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from <Group γ> [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
In the formula (1), G is a group represented by the formula G1, and R a may have one or more atoms or groups selected from <Group β>. Or
G is a group represented by the formula G2, and R b is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group γ>,
G is a group represented by the formula G3, and R c is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, or ,
G is a group represented by the formula G4, R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, and R e Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from <Group γ> [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
In the formula (1), G is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2, 2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N -Dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-tri Fluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-tri Ruoroechiru) an amino group [claim 1], [embodiment A] - [aspect Z], compounds according to any one of embodiments AA] - [aspect AI] and [Embodiment 1] to [Embodiment 5];
In the formula (1), G is fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-tri Fluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl Amino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) Amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroe Le) is an amino group [claim 1], [embodiment A] - [aspect Z], compounds according to any one of embodiments AA] - [aspect AI] and [Embodiment 1] to [Embodiment 5];
In the formula (1), G is methyl group, ethyl group, propyl group, isopropyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group , Propylthio group, isopropylthio group, 2,2,2-trifluoroethylthio group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N- Methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroethyl) amino group [Claim 1], [ Like A] - [aspect Z], compounds according to any one of embodiments AA] - [aspect AI] and [Embodiment 1] to [Embodiment 5];
In the formula (1), G is a group represented by the formula G2, and R b may have one or more atoms or groups selected from <Group γ>. A C1-C6 chain hydrocarbon which is a group, or G is a group represented by the formula G3, and R c may have one or more atoms or groups selected from <Group γ> [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AH] and [Aspect 1] to [Aspect 5] which are groups;
In the formula (1), G is methoxy group, ethoxy group, propoxy group, isopropoxy group, 2,2,2-trifluoroethoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, or 2,2, The compound according to any one of [Item 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5], which is a 2-trifluoroethylthio group ;
In the formula (1), G is a group represented by the formula G1, and R a may have one or more atoms or groups selected from <Group β>. Group or
G is a group represented by the formula G4, R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, and R e Is a C1-C6 chain hydrocarbon group or hydrogen atom optionally having one or more atoms or groups selected from <Group γ> [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
In the formula (1), G is methyl group, ethyl group, propyl group, isopropyl group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N. -Methylamino group, N-methyl-N-propylamino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group , N-ethylamino group, N-propylamino group, N-isopropylamino group or N- (2,2,2-trifluoroethyl) amino group [Claim 1], [Aspect A] to [Aspect Z] [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5]
In the formula (1), G is a group represented by the formula G1, and R a may have one or more atoms or groups selected from <Group β>. [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5], which are groups;
[Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] wherein G is a methyl group, an ethyl group, a propyl group or an isopropyl group in the formula (1) ] To [Aspect 5];
In the formula (1), G is a group represented by the formula G2, and R b may have one or more atoms or groups selected from <Group γ>. [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5], which are groups;
In the formula (1), G is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group or a 2,2,2-trifluoroethoxy group [Claim 1], [Aspect A] to [Aspect Z], [ Compound according to any one of Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5];
In the formula (1), G is a group represented by the formula G3, and R c may have one or more atoms or groups selected from <Group γ>. [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5], which are groups;
In the formula (1), G is a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group or a 2,2,2-trifluoroethylthio group [Claim 1], [Aspect A] to [Aspect Z], The compound according to any one of [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5];
In Formula (1), G is a group represented by Formula G4, and R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>. And R e is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more atoms or groups selected from <Group γ> [Claim 1], [Aspect A ] To [Aspect Z], [Aspect AA] to [Aspect AI] and [Aspect 1] to [Aspect 5];
In the formula (1), G is N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N-ethyl-N-methylamino group, N-methyl-N-propyl. Amino group, N-isopropyl-N-methylamino group, N-methyl-N- (2,2,2-trifluoroethyl) amino group, N-methylamino group, N-ethylamino group, N-propylamino group , N-isopropylamino group or N- (2,2,2-trifluoroethyl) amino group [Claim 1], [Aspect A] to [Aspect Z], [Aspect AA] to [Aspect AI] and [ The compound according to any one of [Aspect 1] to [Aspect 5].
　また、本発明化合物として、例えば、以下のヘテロ芳香環化合物も挙げられる。 In addition, examples of the compound of the present invention include the following heteroaromatic ring compounds.
　式（１ｘ） Formula (1x)
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
〔式中、
　Ｇzは、水素原子、Ｃ１－Ｃ３アルキル基（メチル基、エチル基等）、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基（メトキシ基、エトキシ基、２，２，２－トリフルオロエトキシ基等）、Ｃ１－Ｃ６アルキルチオ基（メチルチオ基、エチルチオ基等）、Ｃ２～Ｃ８ジアルキルアミノ基（Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基等）、ハロゲン原子（フッ素原子、塩素原子、臭素原子等）を表し、
　Ｄは－Ｎ＝または－ＣＨ＝（好ましくは、－ＣＨ＝）を表し、
　ｍは０または１（好ましくは０）を表す。〕
で示される［項１]記載のヘテロ芳香環化合物；
　式（１ｘ）において、Ｄが－ＣＨ＝であり、ｍが０である［項１]記載のヘテロ芳香環化合物；
　式（１ｙ） [Where,
G z represents a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C6 alkoxy group (methoxy group, ethoxy group, 2,2, etc.) optionally having one or more halogen atoms. 2-trifluoroethoxy group etc.), C1-C6 alkylthio group (methylthio group, ethylthio group etc.), C2-C8 dialkylamino group (N, N-dimethylamino group, N, N-diethylamino group etc.), halogen atom ( Fluorine atom, chlorine atom, bromine atom, etc.)
D represents —N═ or —CH═ (preferably —CH═);
m represents 0 or 1 (preferably 0). ]
The heteroaromatic ring compound according to [Claim 1] represented by:
[Claim 1] The heteroaromatic ring compound according to [1], wherein D is —CH═ and m is 0 in formula (1x);
Formula (1y)
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
〔式中、
　Ｇzは、水素原子、Ｃ１－Ｃ３アルキル基（メチル基、エチル基等）、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基（メトキシ基、エトキシ基、２，２，２－トリフルオロエトキシ基等）、Ｃ１－Ｃ６アルキルチオ基（メチルチオ基、エチルチオ基等）、Ｃ２～Ｃ８ジアルキルアミノ基（Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基等）、ハロゲン原子（フッ素原子、塩素原子、臭素原子等）を表し、
　Ｄは－Ｎ＝または－ＣＨ＝（好ましくは、－ＣＨ＝）を表し、
　ｍは０または１（好ましくは０）を表す。〕
で示される［項１]記載のヘテロ芳香環化合物；
　式（１ｙ）において、Ｄが－ＣＨ＝であり、ｍが０である［項１]記載のヘテロ芳香環化合物；
　式（１ｚ） [Where,
G z represents a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C6 alkoxy group (methoxy group, ethoxy group, 2,2, etc.) optionally having one or more halogen atoms. 2-trifluoroethoxy group etc.), C1-C6 alkylthio group (methylthio group, ethylthio group etc.), C2-C8 dialkylamino group (N, N-dimethylamino group, N, N-diethylamino group etc.), halogen atom ( Fluorine atom, chlorine atom, bromine atom, etc.)
D represents —N═ or —CH═ (preferably —CH═);
m represents 0 or 1 (preferably 0). ]
The heteroaromatic ring compound according to [Claim 1] represented by:
The heteroaromatic ring compound according to [Item 1], wherein D is —CH═ and m is 0 in Formula (1y);
Formula (1z)
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000033
〔式中、
　Ｇzは、水素原子、Ｃ１－Ｃ３アルキル基（メチル基、エチル基等）、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基（メトキシ基、エトキシ基、２，２，２－トリフルオロエトキシ基等）、Ｃ１－Ｃ６アルキルチオ基（メチルチオ基、エチルチオ基等）、Ｃ２～Ｃ８ジアルキルアミノ基（Ｎ，Ｎ－ジメチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基等）、ハロゲン原子（フッ素原子、塩素原子、臭素原子等）を表し、
　Ｄは－Ｎ＝または－ＣＨ＝（好ましくは、－ＣＨ＝）を表し、
　ｍは０または１（好ましくは０）を表す。〕
で示される［項１]記載のヘテロ芳香環化合物；
　式（１ｚ）において、Ｄが－ＣＨ＝であり、ｍが０である［項１]記載のヘテロ芳香環化合物。 [Where,
G z represents a hydrogen atom, a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C6 alkoxy group (methoxy group, ethoxy group, 2,2, etc.) optionally having one or more halogen atoms. 2-trifluoroethoxy group etc.), C1-C6 alkylthio group (methylthio group, ethylthio group etc.), C2-C8 dialkylamino group (N, N-dimethylamino group, N, N-diethylamino group etc.), halogen atom ( Fluorine atom, chlorine atom, bromine atom, etc.)
D represents —N═ or —CH═ (preferably —CH═);
m represents 0 or 1 (preferably 0). ]
The heteroaromatic ring compound according to [Claim 1] represented by:
The heteroaromatic ring compound according to [Item 1], wherein in formula (1z), D is —CH═ and m is 0.
　次に本発明化合物の製造法について説明する。 Next, a method for producing the compound of the present invention will be described.
　本発明化合物は、例えば、以下の（製造法１）～（製造法１０）にしたがって製造することができる。
（製造法１）
　本発明化合物のうち、Ｈｅｔが式Ｈ１、Ｈ２、Ｈ３またはＨ４で示される環であり、Ｑが式Ｑ１で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 The compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 10).
(Production method 1)
Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q1 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
〔式中、Ｊ、Ｌ、Ａ、Ｄ、Ｇ、Ｒxおよびｍは前記と同じ意味を表し、Ｈｅｔ１は式Ｈ１、Ｈ２、Ｈ３またはＨ４で示される環を表し、Ｒy1は、＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基またはシクロプロピル基を表し、Ｌｇ１は、臭素原子またはヨウ素原子を表し、Ｌｇ２は、塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、パラトルエンスルホニルオキシ基、または、トリフルオロメタンスルホニルオキシ基等の脱離基を表す。〕
・（５ａ）→（３）
　化合物（５ａ）と金属マグネシウムとを反応させることによって生成するグリニャール反応剤を、式（２）で示されるアミド化合物と反応させることにより化合物（３）を製造することができる。 [Wherein, J, L, A, D, G, R x and m represent the same meaning as described above, Het1 represents a ring represented by the formula H1, H2, H3 or H4, and R y1 represents <group α > Represents a C1-C6 chain hydrocarbon group or a cyclopropyl group which may have one or more atoms or groups selected from: Lg 1 represents a bromine atom or an iodine atom, and Lg 2 represents chlorine It represents a leaving group such as an atom, bromine atom, iodine atom, methanesulfonyloxy group, paratoluenesulfonyloxy group, or trifluoromethanesulfonyloxy group. ]
・ (5a) → (3)
Compound (3) can be produced by reacting a Grignard reactant produced by reacting compound (5a) with metallic magnesium with an amide compound represented by formula (2).
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン等のエーテル類が挙げられる。 The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as diethyl ether and tetrahydrofuran.
　化合物（５ａ）１モルに対して、金属マグネシウムは通常１モルの割合で用いられるが、適宜変更することができる。また、必要に応じて触媒量の活性化剤を加えて、金属マグネシウムを活性化させることができる。該活性化剤としては、例えば、ヨウ素、１，２－ジブロモエタンが挙げられる。 Metallic magnesium is usually used at a ratio of 1 mole per 1 mole of compound (5a), but can be changed as appropriate. Further, if necessary, a catalytic amount of an activator can be added to activate the magnesium metal. Examples of the activator include iodine and 1,2-dibromoethane.
　化合物（５ａ）と金属マグネシウムとの反応における反応温度は、通常室温から用いる溶媒の沸点の範囲であり、反応時間は、通常瞬時から１時間の範囲である。 The reaction temperature in the reaction between the compound (5a) and metallic magnesium is usually in the range of the boiling point of the solvent used from room temperature, and the reaction time is usually in the range of 1 hour from the instant.
　化合物（５ａ）１モルに対して化合物（２）は通常１モルの割合で用いられるが、適宜変更することができる。 Compound (2) is usually used at a ratio of 1 mol per 1 mol of compound (5a), but can be appropriately changed.
　生成したグリニャール反応剤と化合物（２）との反応における反応温度は、通常－７８℃から溶媒の沸点の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。 The reaction temperature in the reaction between the produced Grignard reactant and the compound (2) is usually in the range of −78 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、化合物（３）を単離することができる。
・（３）→（７）
　化合物（３）を還元することにより、化合物（７）を製造することができる。 After completion of the reaction, the compound (3) can be isolated by carrying out ordinary post-treatment operations.
・ (3) → (7)
Compound (7) can be produced by reducing compound (3).
　還元方法としては、例えば、水素化ホウ素ナトリウムを用いる還元反応が挙げらる。化合物（３）１モルに対して、水素化ホウ素ナトリウムは通常０．２５モル～１モルの割合で用いられるが、適宜変更することができる。 Examples of the reduction method include a reduction reaction using sodium borohydride. Sodium borohydride is usually used at a ratio of 0.25 mol to 1 mol with respect to 1 mol of the compound (3), but can be appropriately changed.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばメタノール、エタノール、イソプロピルアルコール等のアルコール類が挙げられる。 The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include alcohols such as methanol, ethanol, isopropyl alcohol and the like.
　該反応における反応温度は、通常０℃から溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 0 ° C. to the boiling point of the solvent.
　該反応における反応時間は、通常瞬時から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 24 hours from the instant.
　反応終了後は、通常の後処理操作を行うことにより、化合物（７）を単離することができる。
・（５ａ）→（７）
　化合物（５ａ）をアルキルリチウム化合物と反応させた後に、生成する反応中間体と式（６）で示されるカルボニル化合物と反応させることにより、化合物（７）を製造することができる。 After completion of the reaction, the compound (7) can be isolated by performing ordinary post-treatment operations.
・ (5a) → (7)
Compound (7) can be produced by reacting compound (5a) with an alkyllithium compound and then reacting the resulting reaction intermediate with a carbonyl compound represented by formula (6).
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類が挙げられる。 The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Is mentioned.
　該反応に用いられるアルキルリチウム化合物としては、例えば、ブチルリチウムが挙げられる。化合物（５ａ）１モルに対して、アルキルリチウム化合物は通常１モルの割合で用いられるが、適宜変更することができる。 Examples of the alkyl lithium compound used in the reaction include butyl lithium. The alkyllithium compound is usually used in a proportion of 1 mol with respect to 1 mol of the compound (5a), but can be appropriately changed.
　化合物（５ａ）とアルキルリチウム化合物との反応における反応温度は、通常－７８℃から－５０℃の範囲であり、反応時間は、通常瞬時から１時間の範囲である。 The reaction temperature in the reaction between the compound (5a) and the alkyl lithium compound is usually in the range of −78 ° C. to −50 ° C., and the reaction time is usually in the range of 1 hour from the instant.
　化合物（５ａ）１モルに対して化合物（６）は通常１モルの割合で用いられるが、適宜変更することができる。 Compound (6) is usually used at a ratio of 1 mol per 1 mol of compound (5a), but can be appropriately changed.
　該反応中間体と化合物（６）との反応における反応温度は、通常－７８℃から３０℃の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。 The reaction temperature in the reaction between the reaction intermediate and compound (6) is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、反応混合物に水または塩化アンモニウム水溶液等を注加した後、有機溶媒で抽出し、通常の後処理操作を行うことにより、化合物（７）を単離することができる。
・（４）→（７）
化合物（４）をリチオ化した後に、生成する反応中間体と式（１６）で示されるカルボニル化合物と反応させることにより、化合物（７）を製造することができる。 After completion of the reaction, the compound (7) can be isolated by pouring water or an aqueous ammonium chloride solution into the reaction mixture, extracting with an organic solvent, and performing a normal post-treatment operation.
・ (4) → (7)
After lithiation of compound (4), compound (7) can be produced by reacting the resulting reaction intermediate with the carbonyl compound represented by formula (16).
　リチオ化に用いられるリチウム化合物としては、例えば、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔｅｒｔ－ブチルリチウム等のアルキルリチウム化合物、リチウムジイソプロピルアミド、リチウムテトラメチルピペリジド等のリチウムジアルキルアミド化合物が挙げられる。 Examples of the lithium compound used for lithiation include alkyllithium compounds such as butyllithium, sec-butyllithium and tert-butyllithium, and lithium dialkylamide compounds such as lithium diisopropylamide and lithium tetramethylpiperidide.
　中でも、化合物（４）のうち、Ｇが－ＮＨＣ（Ｏ）ｔ－Ｂｕである化合物のリチオ化は、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラメチルエチレンジアミン（ＴＭＥＤＡ）の存在下、ブチルリチウムを用いて行うことができる。 In particular, among the compounds (4), lithiation of a compound in which G is —NHC (O) t-Bu is performed by butyllithium in the presence of N, N, N ′, N′-tetramethylethylenediamine (TMEDA). Can be used.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばジエチルエーテル、テトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類が挙げられる。 The reaction is usually performed in the presence of a solvent, and examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane.
　化合物（４）１モルに対して、ブチルリチウムおよびＴＭＥＤＡはそれぞれ通常１モルの割合で用いられるが、適宜変更することができる。 Butyllithium and TMEDA are usually used in a ratio of 1 mol per 1 mol of compound (4), but can be appropriately changed.
　化合物（４）とブチルリチウムとの反応における反応温度は、通常－７８℃から３０℃の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。 The reaction temperature in the reaction between compound (4) and butyl lithium is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
　該反応中間体と化合物（１６）との反応における反応温度は、通常－７８℃から３０℃の範囲であり、反応時間は、通常０．１時間から２４時間の範囲である。 The reaction temperature in the reaction between the reaction intermediate and compound (16) is usually in the range of −78 ° C. to 30 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、化合物（７）を単離することができる。
・（７）→（１ａ）
　本発明化合物（１ａ）は、化合物（７）を脱ヒドロキシ化することにより製造することができる。脱ヒドロキシ化の方法としては、例えば、接触水素還元反応などが挙げられる。 After completion of the reaction, the compound (7) can be isolated by performing ordinary post-treatment operations.
・ (7) → (1a)
The compound (1a) of the present invention can be produced by dehydroxylating the compound (7). Examples of the dehydroxylation method include a catalytic hydrogen reduction reaction.
　接触水素還元反応は、溶媒および触媒の存在下、水素と反応させて行う。 The catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.
　該反応に用いられる溶媒としては、例えば酢酸が挙げられる。また必要に応じて硫酸等の鉱酸を加えることができ、その場合のモル比は化合物（７）１モルに対して、通常０．０１モル～１０モルである。 Examples of the solvent used in the reaction include acetic acid. If necessary, a mineral acid such as sulfuric acid can be added. In this case, the molar ratio is usually 0.01 mol to 10 mol with respect to 1 mol of the compound (7).
　該反応に用いられる触媒としては、例えば、パラジウム炭素等が挙げられる。 Examples of the catalyst used in the reaction include palladium on carbon.
　該反応における、水素圧は通常１気圧から５気圧である。 In this reaction, the hydrogen pressure is usually 1 to 5 atm.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、ろ過によって触媒を除去した後、通常の後処理操作を行うことにより、本発明化合物（１ａ）を単離することができる。
・（１ａ）→（１ｂ）
　さらに、本発明化合物（１ａ）とリチウムジイソプロピルアミド（以下、ＬＤＡと記す。）等の塩基とを反応させた後、Ｒy1－Ｌｇ２で示される化合物と反応させることにより、本発明化合物（１ｂ）を製造することもできる。
（製造法２）
　本発明化合物のうち、Ｈｅｔが式Ｈ１、Ｈ２、Ｈ３またはＨ４で示される環であり、Ｑが式Ｑ２で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of the reaction, the compound (1a) of the present invention can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.
・ (1a) → (1b)
Further, the compound (1b) of the present invention is reacted with a base such as lithium diisopropylamide (hereinafter referred to as LDA) and then reacted with a compound represented by R y1 -Lg 2. ) Can also be manufactured.
(Production method 2)
Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q2 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000035
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ１、Ｄ、Ｇおよびｍは前記と同じ意味を表し、Ｌｇ３は、ハロゲン原子を表す。〕
　本発明化合物（１ｃ）は、化合物（８）と、化合物（９）とを、塩基、および、必要に応じて銅化合物の存在下反応させることにより製造することができる。
（１）銅化合物を用いない場合：
　Ｌｇ３としては塩素原子またはフッ素原子が好ましい。 Wherein, J, L, A, Het1 , D, G and m are as defined above, Lg 3 represents a halogen atom. ]
The compound (1c) of the present invention can be produced by reacting the compound (8) with the compound (9) in the presence of a base and, if necessary, a copper compound.
(1) When no copper compound is used:
Lg 3 is preferably a chlorine atom or a fluorine atom.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げる。化合物（８）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (8).
　化合物（８）１モルに対して化合物（９）は通常１モルの割合で用いられるが、適宜変更することができる。 Compound (9) is usually used at a ratio of 1 mol per 1 mol of compound (8), but can be appropriately changed.
　該反応における反応温度は、通常２０℃から２００℃あるいは溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｃ）を単離することができる。
（２）銅化合物を用いる場合：
　Ｌｇ３としては臭素原子またはヨウ素原子が好ましい。 After completion of the reaction, the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations.
(2) When using a copper compound:
Lg 3 is preferably a bromine atom or an iodine atom.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げる。化合物（８）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (8).
　銅化合物としては、銅粉末、酸化銅（Ｉ）、塩化銅（Ｉ）、臭化銅（Ｉ）、ヨウ化銅（Ｉ）等が挙げられる。化合物（８）１モルに対して、銅化合物は通常０．０１モル～１０モルの割合で用いられる。 Examples of the copper compound include copper powder, copper oxide (I), copper chloride (I), copper bromide (I), copper iodide (I) and the like. The copper compound is usually used in a proportion of 0.01 mol to 10 mol with respect to 1 mol of the compound (8).
　化合物（８）１モルに対して化合物（９）は通常１モルの割合で用いられるが、適宜変更することができる。 Compound (9) is usually used at a ratio of 1 mol per 1 mol of compound (8), but can be appropriately changed.
　該反応における反応温度は、通常５０℃から２００℃あるいは溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 50 ° C. to 200 ° C. or the boiling point of the solvent.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。
反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｃ）を単離することができる。
（製造法３）
　本発明化合物のうち、Ｈｅｔが式Ｈ１、Ｈ２、Ｈ３またはＨ４で示される環であり、Ｑが式Ｑ３で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 The reaction time in the reaction is usually in the range of 0.1 hour to 24 hours.
After completion of the reaction, the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations.
(Production method 3)
Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q3 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000036
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ１、Ｄ、Ｇおよびｍは前記と同じ意味を表し、Ｌｇ３は、ハロゲン原子を表し、ｙ１は１または２を表す。〕
　本発明化合物（１ｄ）は、化合物（１０）と、化合物（９）とを、塩基、および、必要に応じて銅化合物の存在下反応させるか、あるいは、化合物（５ｂ）と、化合物（１１）とを、塩基、および、必要に応じて銅化合物の存在下反応させることにより製造することができる。
・（１ｄ）の製造
（１）銅化合物を用いない場合：
　Ｌｇ３としては塩素原子またはフッ素原子が好ましい。 Wherein, J, L, A, Het1 , D, G and m are as defined above, Lg 3 represents a halogen atom, y1 is 1 or 2. ]
The compound (1d) of the present invention is obtained by reacting the compound (10) and the compound (9) in the presence of a base and, if necessary, a copper compound, or the compound (5b) and the compound (11). Can be produced in the presence of a base and, if necessary, a copper compound.
-Production of (1d) (1) When not using a copper compound:
Lg 3 is preferably a chlorine atom or a fluorine atom.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げる。化合物（１０）または化合物（１１）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
　化合物（１０）または化合物（１１）１モルに対して化合物（９）または化合物（５ｂ）は通常１モルの割合で用いられるが、適宜変更することができる。 The compound (9) or the compound (5b) is usually used at a ratio of 1 mol per 1 mol of the compound (10) or the compound (11), but can be appropriately changed.
　該反応における反応温度は、通常２０℃から２００℃あるいは溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｄ）を単離することができる。
（２）銅化合物を用いる場合：
　Ｌｇ３としては臭素原子またはヨウ素原子が好ましい。 After completion of the reaction, the compound of the present invention (1d) can be isolated by carrying out ordinary post-treatment operations.
(2) When using a copper compound:
Lg 3 is preferably a bromine atom or an iodine atom.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げられる。化合物（１０）または化合物（１１）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
　銅化合物としては、銅粉末、酸化銅（Ｉ）、塩化銅（Ｉ）、臭化銅（Ｉ）、ヨウ化銅（Ｉ）等が挙げられる。化合物（１０）または化合物（１１）１モルに対して、銅化合物は通常０．０１モル～１０モルの割合で用いられる。 Examples of the copper compound include copper powder, copper oxide (I), copper chloride (I), copper bromide (I), copper iodide (I) and the like. The copper compound is usually used in a proportion of 0.01 mol to 10 mol with respect to 1 mol of the compound (10) or the compound (11).
　化合物（１０）または化合物（１１）１モルに対して、化合物（９）または化合物（５ｂ）は通常１モル用いられるが、適宜変更することができる。 The compound (9) or the compound (5b) is usually used in an amount of 1 mol per 1 mol of the compound (10) or the compound (11), but can be appropriately changed.
　該反応における反応温度は、通常５０℃から２００℃あるいは溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 50 ° C. to 200 ° C. or the boiling point of the solvent.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｄ）を単離することができる。
・（１ｄ）→（１ｅ）
　さらに、本発明化合物（１ｄ）を、過酸化水素、メタクロロ過安息香酸（以下、ｍＣＰＢＡと記す。）、過ヨウ素酸ナトリウム等の酸化剤と反応させることにより、本発明化合物（１ｅ）を製造することもできる。
（製造法４）
　本発明化合物のうち、Ｈｅｔが式Ｈ１、Ｈ２、Ｈ３またはＨ４で示される環であり、Ｑが式Ｑ４で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of the reaction, the compound of the present invention (1d) can be isolated by carrying out ordinary post-treatment operations.
・ (1d) → (1e)
Further, the compound (1e) of the present invention is produced by reacting the compound (1d) of the present invention with an oxidizing agent such as hydrogen peroxide, metachloroperbenzoic acid (hereinafter referred to as mCPBA), sodium periodate or the like. You can also.
(Production Method 4)
Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H1, H2, H3 or H4 and Q is a group represented by the formula Q4 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000037
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ１、Ｄ、Ｇ、Ｒzおよびｍは前記と同じ意味を表し、Ｌｇ３は、ハロゲン原子を表し、Ｌｇ４は、ハロゲン原子またはトリフルオロメタンスルホニルオキシ基を表す。〕
　本発明化合物（１ｆ）は、化合物（１２）と、化合物（９）とを、塩基、および、必要に応じてパラジウム触媒の存在下反応させるか、あるいは、化合物（５ｃ）と、化合物（１３）とを、塩基、および、必要に応じてパラジウム触媒の存在下反応させることにより製造することができる。
（１）パラジウム触媒を用いない場合：
　Ｌｇ３およびＬｇ４としては塩素原子またはフッ素原子が好ましい。 Wherein, J, L, A, Het1 , D, G, R z and m are as defined above, Lg 3 represents a halogen atom, Lg 4 is a halogen atom or a trifluoromethanesulfonyloxy group To express. ]
The compound (1f) of the present invention is obtained by reacting the compound (12) with the compound (9) in the presence of a base and, if necessary, a palladium catalyst, or the compound (5c) and the compound (13). Can be produced in the presence of a base and, if necessary, a palladium catalyst.
(1) When no palladium catalyst is used:
Lg 3 and Lg 4 are preferably a chlorine atom or a fluorine atom.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、例えば、ピリジン、トリエチルアミン、ジイソプロピルエチルアミン等の有機塩基類、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等が挙げられる。化合物（１２）または化合物（１３）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include organic bases such as pyridine, triethylamine and diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (12) or compound (13).
　化合物（１２）または化合物（１３）１モルに対して化合物（９）または化合物（５ｃ）は通常１モルの割合で用いられるが、適宜変更することができる。 The compound (9) or the compound (5c) is usually used at a ratio of 1 mol per 1 mol of the compound (12) or the compound (13), but can be appropriately changed.
　該反応における反応温度は、通常２０℃から、２００℃または溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｆ）を単離することができる。
（２）パラジウム触媒を用いる場合：
　Ｌｇ３およびＬｇ４としては臭素原子、ヨウ素原子またはトリフルオロメタンスルホニルオキシ基が好ましい。 After completion of the reaction, the compound of the present invention (1f) can be isolated by carrying out ordinary post-treatment operations.
(2) When using a palladium catalyst:
Lg 3 and Lg 4 are preferably a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group.
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類が挙げられる。 The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. .
　該反応において用いられる塩基としては、例えば、ナトリウムtert-ブトキシド、炭酸セシウム等が挙げられる。化合物（１２）または化合物（１３）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include sodium tert-butoxide, cesium carbonate and the like. The base is usually used at a ratio of 1 mol to 10 mol with respect to 1 mol of the compound (12) or compound (13).
　該反応において用いられるパラジウム触媒としては、たとえば、｛１，１’－ビス（ジフェニルホスフィノ）フェロセン｝ジクロロパラジウム、およびトリス（ジベンジリデンアセトン）ジパラジウム（以下、Ｐｄ2(ｄｂａ)3と記す。）と４，５－ビス(ジフェニルホスフィノ)－９，９－ジメチルキサンテン（以下、キサントホスと記す。）との組み合わせ、等が挙げられる。化合物（１２）または化合物（１３）１モルに対して、パラジウム触媒は通常０．０１～０．２モルの割合で用いられる。 Examples of the palladium catalyst used in the reaction are {1,1′-bis (diphenylphosphino) ferrocene} dichloropalladium and tris (dibenzylideneacetone) dipalladium (hereinafter referred to as Pd 2 (dba) 3 . ) And 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene (hereinafter referred to as xanthophos), and the like. The palladium catalyst is usually used in a proportion of 0.01 to 0.2 mol with respect to 1 mol of the compound (12) or compound (13).
　化合物（１２）または化合物（１３）１モルに対して化合物（９）または化合物（５ｃ）は通常１モルの割合で用いられるが、適宜変更することができる。 The compound (9) or the compound (5c) is usually used at a ratio of 1 mol per 1 mol of the compound (12) or the compound (13), but can be appropriately changed.
　該反応における反応温度は、通常２０℃から１００℃の範囲である。 The reaction temperature in the reaction is usually in the range of 20 ° C to 100 ° C.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｆ）を単離することができる。
（製造法５）
　本発明化合物のうち、Ｄが－Ｎ＝であり、Ｈｅｔが式Ｈ１、Ｈ２、Ｈ３またはＨ４で示される環であり、Ｑが式Ｑ２、Ｑ３またはＱ４で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of the reaction, the compound of the present invention (1f) can be isolated by carrying out ordinary post-treatment operations.
(Production method 5)
Among the compounds of the present invention, a compound in which D is —N═, Het is a ring represented by the formula H1, H2, H3 or H4, and Q is a group represented by the formula Q2, Q3 or Q4 is, for example, It can be produced according to the following scheme.
Figure JPOXMLDOC01-appb-C000038
Figure JPOXMLDOC01-appb-C000038
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ１、Ｇおよびｍは前記と同じ意味を表し、Ｑaは、式Ｑ２、Ｑ３またはＱ４で示される基を表し、Ｌｇ３は、ハロゲン原子を表す。〕
・（１５）の製造
　化合物（１５）は、化合物（１４）とジハロピリミジン化合物（１６）とを、塩基の存在下に反応させることにより製造することができる。 Wherein, J, L, A, Het1, G and m are as defined above, Q a represents a group of the formula Q2, Q3 or Q4, Lg 3 represents a halogen atom. ]
-Production of (15) Compound (15) can be produced by reacting compound (14) with dihalopyrimidine compound (16) in the presence of a base.
　化合物（１６）の２つのＬｇ３は相異なっていてもよいが、２つのＬｇ３がともに塩素原子である化合物が好ましい。 Two Lg 3 in the compound (16) may be different from each other, but a compound in which the two Lg 3 are both chlorine atoms is preferable.
　該反応は、前記の製造法２（１）、製造法３（１）または製造法４（１）に準じて行うことができる。
・（１５）→（１ｇ）
　本発明化合物（１ｇ）は、化合物（１５）を脱ハロゲン化することにより製造することができる。脱ハロゲン化の方法としては、例えば、接触水素還元反応などが挙げられる。接触水素還元反応は、溶媒および触媒の存在下、水素と反応させて行う。 This reaction can be carried out according to the above Production Method 2 (1), Production Method 3 (1) or Production Method 4 (1).
・ (15) → (1g)
The compound (1g) of the present invention can be produced by dehalogenating the compound (15). Examples of the dehalogenation method include a catalytic hydrogen reduction reaction. The catalytic hydrogen reduction reaction is performed by reacting with hydrogen in the presence of a solvent and a catalyst.
　該反応に用いられる溶媒としては、例えば、メタノール、エタノール等のアルコール類、酢酸エチル等のエステル類、酢酸等のカルボン酸類および水が挙げられる。 Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, esters such as ethyl acetate, carboxylic acids such as acetic acid, and water.
　また必要に応じて塩基または酸を加えることができる。その場合のモル比は化合物（１５）１モルに対して、通常０．０１モル～１０モルである。 Also, a base or acid can be added as necessary. In this case, the molar ratio is usually 0.01 mol to 10 mol with respect to 1 mol of compound (15).
　該反応に用いられる塩基としては、例えば、酸化マグネシウム、水酸化ナトリウム、酢酸ナトリウム、トリエチルアミンが挙げられる。酸としては、例えば、硫酸、塩酸が挙げられる。 Examples of the base used in the reaction include magnesium oxide, sodium hydroxide, sodium acetate, and triethylamine. Examples of the acid include sulfuric acid and hydrochloric acid.
　該反応に用いられる触媒としては、例えば、パラジウム炭素が挙げられる。 Examples of the catalyst used in the reaction include palladium on carbon.
　該反応における、水素圧は通常１気圧から５気圧である。 In this reaction, the hydrogen pressure is usually 1 to 5 atm.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、ろ過によって触媒を除去した後、通常の後処理操作を行うことにより、本発明化合物（１ｇ）を単離することができる。
（製造法６）
本発明化合物のうち、Ｈｅｔが式Ｈ５で示される環である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of the reaction, the compound of the present invention (1 g) can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.
(Production method 6)
Among the compounds of the present invention, a compound in which Het is a ring represented by the formula H5 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
〔式中、Ｊ、Ｌ、Ａ、Ｚ１、Ｚ２、Ｚ３、Ｒｘ、Ｒｙ、Ｄ、Ｇおよびｍは前記と同じ意味を表し、Ｌｇ２は、塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、パラトルエンスルホニルオキシ基、または、トリフルオロメタンスルホニルオキシ基等の脱離基を表す。〕
　該反応は、通常溶媒の存在下行われ、該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 [Wherein, J, L, A, Z 1 , Z 2 , Z 3 , R x , R y , D, G and m represent the same meaning as described above, and Lg 2 represents a chlorine atom, a bromine atom, an iodine atom Represents a leaving group such as methanesulfonyloxy group, para-toluenesulfonyloxy group, or trifluoromethanesulfonyloxy group. ]
The reaction is usually carried out in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, acetonitrile and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げられる。化合物（１７）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like. The base is generally used in the proportion of 1 mol to 10 mol with respect to 1 mol of the compound (17).
　化合物（１７）１モルに対して化合物（１８）は通常１モルの割合で用いられるが、適宜変更することができる。 Compound (18) is usually used in a ratio of 1 mol per 1 mol of compound (17), but can be appropriately changed.
　該反応における反応温度は、通常２０℃から２００℃あるいは溶媒の沸点の範囲である。 The reaction temperature in the reaction is usually in the range of 20 ° C. to 200 ° C. or the boiling point of the solvent.
　該反応における反応時間は、通常０．１時間から２４時間の範囲である。 The reaction time in the reaction is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｈ）を単離することができる。
（製造法７）
　本発明化合物のうち、Ｇが式Ｇ２で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of the reaction, the compound of the present invention (1h) can be isolated by carrying out ordinary post-treatment operations.
(Production method 7)
Among the compounds of the present invention, a compound in which G is a group represented by the formula G2 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000040
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ、Ｑ、Ｄ、Ｒｂおよびｍは前記と同じ意味を表し、Ｒb1は、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基を表し、Ｒb２は、ＯＨ基の保護基（例えば、メチル基、メトキシメチル基、ベンジル基等）を表し、Ｌｇ２は、塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、パラトルエンスルホニルオキシ基、または、トリフルオロメタンスルホニルオキシ基等の脱離基を表す。〕
・（１ｉ）→（１ｊ’）
　本発明化合物（１ｊ’）は、本発明化合物（１ｉ）とＲb1ＯＨとを、塩基の存在下に反応させることにより製造することができる。 [Wherein, J, L, A, Het, Q, D, R b and m have the same meaning as described above, and R b1 has one or more atoms or groups selected from <Group γ>. Represents an optionally substituted C1-C6 chain hydrocarbon group, R b2 represents a protecting group for an OH group (for example, a methyl group, a methoxymethyl group, a benzyl group, etc.), Lg 2 represents a chlorine atom, a bromine atom, A leaving group such as an iodine atom, a methanesulfonyloxy group, a paratoluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group is represented. ]
・ (1i) → (1j ′)
The compound (1j ′) of the present invention can be produced by reacting the compound (1i) of the present invention with R b1 OH in the presence of a base.
　該反応は、通常溶媒の存在下で行われるが、Ｒb1ＯＨを溶媒量用いてもよい。 The reaction is usually performed in the presence of a solvent, but R b1 OH may be used in an amount of a solvent.
　該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げられる。 Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
　本発明化合物（１ｉ）１モルに対して、Ｒb1ＯＨが通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。 R b1 OH is usually used in a proportion of 1 to 10 mol and a base is usually used in a proportion of 1 to 10 mol per mol of the compound (1i) of the present invention.
　該反応の反応温度は、通常０℃～溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。 The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｊ’）を単離することができる。
・（１ｌ）→（１ｋ）
　本発明化合物（１ｋ）は、化合物（１ｌ）を脱保護することにより製造することができる。 After completion of the reaction, the compound of the present invention (1j ′) can be isolated by carrying out ordinary post-treatment operations.
・ (1l) → (1k)
The compound (1k) of the present invention can be produced by deprotecting the compound (1l).
　保護基であるＲb２としては、例えば、メチル基、メトキシメチル基およびベンジル基が挙げられ、当業者に公知の方法で脱保護することができる。
・（１ｋ）→（１ｊ）
　本発明化合物（１ｊ）は、本発明化合物（１ｋ）とＲbＬｇ２とを、塩基の存在下に反応させることにより製造することができる。 Examples of the protecting group R b2 include a methyl group, a methoxymethyl group, and a benzyl group, which can be deprotected by methods known to those skilled in the art.
・ (1k) → (1j)
The compound (1j) of the present invention can be produced by reacting the compound (1k) of the present invention with R b Lg 2 in the presence of a base.
　該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
　該反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類、炭酸カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等の炭酸塩類等、水酸化ナトリウム、水酸化カリウム等の金属水酸化物、ピリジン、トリエチルアミン、ジイソプロピルエチルアミン等の有機塩基類、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等が挙げられる。本発明化合物（１ｋ）１モルに対して、塩基は通常１モル～１０モルの割合で用いられる。 Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide. Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is generally used in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (1k) of the present invention.
　本発明化合物（１ｋ）１モルに対して、ＲbＬｇ２は通常１モルの割合で用いられるが、適宜変更することができる。 Present compound (1k) with respect to 1 mole, R b Lg 2 is used usually in a proportion of 1 mole, but may be appropriately changed.
　該反応の反応温度は、通常０℃～溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間である。 The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually from 0.1 to 24 hours.
　反応終了後は、反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｊ）を単離することができる。 After completion of the reaction, the compound (1j) of the present invention can be isolated by carrying out an ordinary post-treatment operation after the completion of the reaction.
　なお、本発明化合物（１ｊ）は本発明化合物（１ｊ’）を包含する。
（製造法８）
　本発明化合物のうち、Ｇが式Ｇ３で示される基である化合物の一部は、例えば、下記のスキームにしたがって製造することができる。 In addition, this invention compound (1j) includes this invention compound (1j ').
(Production method 8)
Among the compounds of the present invention, a part of the compounds in which G is a group represented by the formula G3 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ、Ｑ、Ｄおよびｍは前記と同じ意味を表し、Ｒc1は、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基を表す。〕
　本発明化合物（１ｍ）は、本発明化合物（１ｉ）とＲc1ＳＨとを、塩基の存在下に反応させることにより製造することができる。 [Wherein, J, L, A, Het, Q, D and m represent the same meaning as described above, and R c1 may have one or more atoms or groups selected from <Group γ>. Represents a C1-C6 chain hydrocarbon group. ]
The compound (1m) of the present invention can be produced by reacting the compound (1i) of the present invention with R c1 SH in the presence of a base.
　該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
　該反応において用いられる塩基としては、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム、水素化ナトリウム、炭酸カリウム、炭酸セシウム、カリウムtert－ブトキシド等が挙げられる。 Examples of the base used in the reaction include sodium hydride, sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide and the like.
　本発明化合物（１ｉ）１モルに対して、Ｒc1ＳＨが通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。 R 1 C1 SH is usually used in a proportion of 1 to 10 mol and a base is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (1i) of the present invention.
　該反応の反応温度は通常０℃～溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間である。 The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually from 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｍ）を単離することができる。 After completion of the reaction, the compound of the present invention (1m) can be isolated by carrying out ordinary post-treatment operations.
　この反応終了後、本発明化合物（１ｍ）に対して、更に当業者に公知の酸化反応を行うことにより、本発明化合物（１ｍ）における－ＳＲc1を－Ｓ(Ｏ)z１Ｒc1（この場合、ｚ１は１または２を表す）に変換することもできる。
（製造法９）
　本発明化合物のうち、Ｇが式Ｇ４で示される基である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of this reaction, the compound (1m) of the present invention is further subjected to an oxidation reaction known to those skilled in the art to convert -SR c1 in the compound (1m) of the present invention to —S (O) z1 R c1 (in this case) , Z1 represents 1 or 2).
(Production method 9)
Among the compounds of the present invention, a compound in which G is a group represented by the formula G4 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000042
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ、Ｑ、Ｄ、Ｒｄ、Ｒｅおよびｍは前記と同じ意味を表し、Ｌｇ２は、塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、パラトルエンスルホニルオキシ基、または、トリフルオロメタンスルホニルオキシ基等の脱離基を表す。〕
・（１ｎ）→（１ｏ）
　本発明化合物（１ｏ）は、本発明化合物（１ｎ）とＲｄＬｇ２とを、塩基の存在下に反応させることにより製造することができる。 [Wherein, J, L, A, Het, Q, D, R d , R e and m represent the same meaning as described above, and Lg 2 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a para A leaving group such as a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group is represented. ]
・ (1n) → (1o)
The compound (1o) of the present invention can be produced by reacting the compound (1n) of the present invention with R d Lg 2 in the presence of a base.
　該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ－メチルピロリジノン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。 Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, N, N-dimethylformamide, Examples thereof include acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
　該反応に用いられる塩基としては、例えば水素化ナトリウム等のアルカリ金属水素化物類、炭酸カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等の炭酸塩類等、水酸化ナトリウム、水酸化カリウム等の金属水酸化物、ピリジン、トリエチルアミン、ジイソプロピルエチルアミン等の有機塩基類、水酸化ナトリウム、水酸化カリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等が挙げられる。本発明化合物（１ｎ）１モルに対して、塩基は通常１モル～２モルの割合で用いられる。 Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, carbonates such as potassium carbonate, potassium carbonate, cesium carbonate and sodium hydrogen carbonate, and metal water such as sodium hydroxide and potassium hydroxide. Examples thereof include oxides, organic bases such as pyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, sodium hydrogen carbonate and the like. The base is generally used in a proportion of 1 mol to 2 mol with respect to 1 mol of the compound (1n) of the present invention.
　本発明化合物（１ｎ）１モルに対して、ＲdＬｇ２が通常１モルの割合で用いられるが適宜変更することができる。 Present compound (1n) with respect to 1 mole, R d Lg 2 is used usually in a proportion of 1 mole may be suitably changed.
　該反応の反応温度は通常０℃～溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。 The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｏ）を単離することができる。
・（１ｏ）→（１ｐ）
　さらに、本発明化合物（１ｏ）に対して、上記に準じる方法でＲｅＬｇ２を反応させることにより、本発明化合物（１ｐ）を製造することができる。 After completion of the reaction, the compound of the present invention (1o) can be isolated by carrying out ordinary post-treatment operations.
・ (1o) → (1p)
Further, with respect to the present invention the compound (1o), by reacting R e Lg 2 is prepared by an analogous procedure to the above, it can be produced the present invention compound (1p).
　また、ＲｄまたはＲｅが１級または２級アルキル基である場合には、上記の方法に代えて、本発明化合物（１ｎ）または本発明化合物（１ｏ）と、アルデヒドまたはケトン化合物とを還元剤の存在下反応させることにより、本発明化合物（１ｏ）または本発明化合物（１ｐ）を製造することもできる。 When R d or R e is a primary or secondary alkyl group, the present compound (1n) or the present compound (1o) and an aldehyde or ketone compound are reduced instead of the above method. The present compound (1o) or the present compound (1p) can also be produced by reacting in the presence of an agent.
　該反応に用いられる還元剤としては、例えば、トリアセトキシ水素化ホウ素ナトリウムが挙げられる。本発明化合物（１ｎ）または本発明化合物（１ｏ）１モルに対して、トリアセトキシ水素化ホウ素ナトリウムは１～５モルの割合で用いられる。 Examples of the reducing agent used in the reaction include sodium triacetoxyborohydride. Sodium triacetoxyborohydride is used in a ratio of 1 to 5 mol per 1 mol of the compound (1n) or the compound (1o) of the present invention.
　該反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、１，４－ジオキサンなどのエーテル類、トルエン、キシレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム等のハロゲン化炭化水素類及びこれらの混合物が挙げられる。また、必要に応じて酢酸等のカルボン酸類を加えて反応を行う。 Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as dichloromethane and chloroform, and the like. A mixture is mentioned. Moreover, it reacts by adding carboxylic acids, such as an acetic acid, as needed.
　本発明化合物（１ｎ）または本発明化合物（１ｏ）１モルに対して、アルデヒドまたはケトン化合物は通常１モルの割合で用いられるが適宜変更することができる。 The aldehyde or ketone compound is usually used at a ratio of 1 mole per 1 mole of the compound (1n) or the compound (1o) of the present invention, but can be appropriately changed.
　該反応の反応温度は通常０℃～溶媒の沸点の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。 The reaction temperature of the reaction is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｏ）または本発明化合物（１ｐ）を単離することができる。
（製造法１０）
　本発明化合物のうち、ｍが１である化合物は、例えば、下記のスキームにしたがって製造することができる。 After completion of the reaction, the compound of the present invention (1o) or the compound of the present invention (1p) can be isolated by carrying out ordinary post-treatment operations.
(Production method 10)
Among the compounds of the present invention, a compound in which m is 1 can be produced, for example, according to the following scheme.
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000043
〔式中、Ｊ、Ｌ、Ａ、Ｈｅｔ、Ｑ、ＤおよびＧは前記と同じ意味を表す。〕
　本発明化合物（１ｒ）は、本発明化合物（１ｑ）を酸化剤と反応させることにより製造することができる。 [Wherein, J, L, A, Het, Q, D and G represent the same meaning as described above. ]
The compound (1r) of the present invention can be produced by reacting the compound (1q) of the present invention with an oxidizing agent.
　該反応は、通常溶媒の存在下で行われる。 The reaction is usually performed in the presence of a solvent.
　該反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等の脂肪族ハロゲン化炭化水素類、酢酸、水及びこれらの混合物が挙げられる。 Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, water, and mixtures thereof.
　該反応に用いられる酸化剤としては、例えば３－クロロ過安息香酸等のカルボン酸の過酸化物、過酸化水素水等が挙げられる。 Examples of the oxidizing agent used in the reaction include peroxides of carboxylic acids such as 3-chloroperbenzoic acid, hydrogen peroxide water, and the like.
　本発明化合物（１ｑ）１モルに対して、酸化剤が通常１～３モルの割合で用いられる。 The oxidizing agent is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the compound (1q) of the present invention.
　該反応の反応温度は、通常－２０～１００℃の範囲であり、反応時間は通常０．１時間から２４時間の範囲である。 The reaction temperature of the reaction is usually in the range of −20 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
　反応終了後は、通常の後処理操作を行うことにより、本発明化合物（１ｒ）を単離することができる。 After completion of the reaction, the compound (1r) of the present invention can be isolated by carrying out ordinary post-treatment operations.
　本発明化合物中には、例えば塩酸塩、硝酸塩、硫酸塩、臭化水素酸塩、リン酸塩、炭酸塩、酢酸塩、乳酸塩、クエン酸塩などの酸付加塩を形成させ得る化合物も存在する。それらの酸付加塩の製造も常法に従うことができ、本発明はこれらの酸付加塩をも包含する。 Among the compounds of the present invention, there are also compounds capable of forming acid addition salts such as hydrochloride, nitrate, sulfate, hydrobromide, phosphate, carbonate, acetate, lactate, citrate, etc. To do. The production of these acid addition salts can also follow conventional methods, and the present invention also includes these acid addition salts.
　本発明化合物が効力を有する有害生物としては、例えば、有害昆虫類や有害ダニ類等の有害節足動物、線形動物及び軟体動物が挙げられる。かかる有害生物としては、具体的には、例えば、以下のものが挙げられる。 Examples of pests for which the compounds of the present invention are effective include harmful arthropods such as harmful insects and harmful mites, linear animals and molluscs. Specific examples of such pests include the following.
　半翅目害虫：ヒメトビウンカ（Ｌａｏｄｅｌｐｈａｘ　ｓｔｒｉａｔｅｌｌｕｓ）、トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）、セジロウンカ（Ｓｏｇａｔｅｌｌａ　ｆｕｒｃｉｆｅｒａ）等のウンカ類、ツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｃｉｎｃｔｉｃｅｐｓ）、タイワンツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｖｉｒｅｓｃｅｎｓ）、チャノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｏｎｕｋｉｉ）等のヨコバイ類、ワタアブラムシ（Ａｐｈｉｓ　ｇｏｓｓｙｐｉｉ）、モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）、ダイコンアブラムシ（Ｂｒｅｖｉｃｏｒｙｎｅ　ｂｒａｓｓｉｃａｅ）、ユキヤナギアブラムシ（Ａｐｈｉｓ　ｓｐｉｒａｅｃｏｌａ）、チューリップヒゲナガアブラムシ（Ｍａｃｒｏｓｉｐｈｕｍ　ｅｕｐｈｏｒｂｉａｅ）、ジャガイモヒゲナガアブラムシ（Ａｕｌａｃｏｒｔｈｕｍ　ｓｏｌａｎｉ）、ムギクビレアブラムシ（Ｒｈｏｐａｌｏｓｉｐｈｕｍ　　ｐａｄｉ）、ミカンクロアブラムシ（Ｔｏｘｏｐｔｅｒａ　ｃｉｔｒｉｃｉｄｕｓ）、モモコフキアブラムシ（Ｈｙａｌｏｐｔｅｒｕｓ　ｐｒｕｎｉ）等のアブラムシ類、アオクサカメムシ（Ｎｅｚａｒａ　ａｎｔｅｎｎａｔａ）、ホソヘリカメムシ（Ｒｉｐｔｏｒｔｕｓ　ｃｌａｖｅｔｕｓ）、クモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ　　ｃｈｉｎｅｎｓｉｓ）、トゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ｐａｒｖｕｓ）、クサギカメムシ（Ｈａｌｙｏｍｏｒｐｈａ　ｍｉｓｔａ）等のカメムシ類、オンシツコナジラミ（Ｔｒｉａｌｅｕｒｏｄｅｓ　ｖａｐｏｒａｒｉｏｒｕｍ）、タバココナジラミ（Ｂｅｍｉｓｉａ　ｔａｂａｃｉ）、ミカンコナジラミ（Ｄｉａｌｅｕｒｏｄｅｓ　ｃｉｔｒｉ）、ミカントゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ　ｓｐｉｎｉｆｅｒｕｓ）等のコナジラミ類、アカマルカイガラムシ（Ａｏｎｉｄｉｅｌｌａ　ａｕｒａｎｔｉｉ）、サンホーゼカイガラムシ（Ｃｏｍｓｔｏｃｋａｓｐｉｓ　ｐｅｒｎｉｃｉｏｓａ）、シトラススノースケール（Ｕｎａｓｐｉｓ　ｃｉｔｒｉ）、ルビーロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｒｕｂｅｎｓ）、イセリヤカイガラムシ（Ｉｃｅｒｙａ　ｐｕｒｃｈａｓｉ）、フジコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ　ｋｒａｕｎｈｉａｅ）、クワコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ　ｌｏｎｇｉｓｐｉｎｉｓ）、クワシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ　ｐｅｎｔａｇｏｎａ）等のカイガラムシ類、グンバイムシ類、トコジラミ（Ｃｉｍｅｘ　ｌｅｃｔｕｌａｒｉｕｓ）等のトコジラミ類、及びキジラミ類等。　　　 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 (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypi), peach aphids (Myzus persicae), radish aphids (Brevicorine brassicae), aphid spiraecola, tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum pasid), citrus aphids (Topoptera citricidus), peach beetles Helmet beetle (Riptortus clavetus), spider helicopter (Leptocorisa chinensis), spider beetle (Eysarcoris parvus), winged beetle (Halyomorpha misista), and the like rodes vaporariorum), sweetpotato whitefly (Bemisia tabaci), mandarin orange whitefly (Dialeurodes citri), whiteflies such as mandarin orange spiny whitefly (Aleurocanthus spiniferus), Acamar scale insects (Aonidiella aurantii), Sanho zero scale insects (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), Ruby Roe beetle (Ceroplastes rubens), Iceria scale insect (Icerya purchasi), Fujino scale insect (Pranococcus kraunhiae), Swan scale scale (Pseudococcus long) ispinis), scale insects such as Pseudouracapis pentagona, bedbugs, bed bugs such as Chime lectularius, and whales. *
　鱗翅目害虫：ニカメイガ（Ｃｈｉｌｏ　ｓｕｐｐｒｅｓｓａｌｉｓ）、サンカメイガ（Ｔｒｙｐｏｒｙｚａ　ｉｎｃｅｒｔｕｌａｓ）、コブノメイガ（Ｃｎａｐｈａｌｏｃｒｏｃｉｓ　ｍｅｄｉｎａｌｉｓ）、ワタノメイガ（Ｎｏｔａｒｃｈａ　ｄｅｒｏｇａｔａ）、ノシメマダラメイガ（Ｐｌｏｄｉａ　ｉｎｔｅｒｐｕｎｃｔｅｌｌａ）、アワノメイガ（Ｏｓｔｒｉｎｉａ　ｆｕｒｎａｃａｌｉｓ）、ハイマダラノメイガ（Ｈｅｌｌｕｌａ　ｕｎｄａｌｉｓ）、シバツトガ（Ｐｅｄｉａｓｉａ　ｔｅｔｅｒｒｅｌｌｕｓ）等のメイガ類、ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｕｒａ）、シロイチモジヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｅｘｉｇｕａ）、アワヨトウ（Ｐｓｅｕｄａｌｅｔｉａ　ｓｅｐａｒａｔａ）、ヨトウガ（Ｍａｍｅｓｔｒａ　ｂｒａｓｓｉｃａｅ）、タマナヤガ（Ａｇｒｏｔｉｓ　ｉｐｓｉｌｏｎ），タマナギンウワバ（Ｐｌｕｓｉａ　　ｎｉｇｒｉｓｉｇｎａ），トリコプルシア属、ヘリオティス属、ヘリコベルパ属等のヤガ類、モンシロチョウ（Ｐｉｅｒｉｓ　ｒａｐａｅ）等のシロチョウ類、アドキソフィエス属、ナシヒメシンクイ（Ｇｒａｐｈｏｌｉｔａ　ｍｏｌｅｓｔａ）、マメシンクイガ（Ｌｅｇｕｍｉｎｉｖｏｒａ　ｇｌｙｃｉｎｉｖｏｒｅｌｌａ），アズキサヤムシガ（Ｍａｔｓｕｍｕｒａｅｓｅｓ　ａｚｕｋｉｖｏｒａ）、リンゴコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｏｒａｎａ　ｆａｓｃｉａｔａ）、チャノコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｈｏｎｍａｉ．）、チャハマキ（Ｈｏｍｏｎａ　ｍａｇｎａｎｉｍａ）、ミダレカクモンハマキ（Ａｒｃｈｉｐｓ　ｆｕｓｃｏｃｕｐｒｅａｎｕｓ）、コドリンガ（Ｃｙｄｉａ　ｐｏｍｏｎｅｌｌａ）等のハマキガ類、チャノホソガ（Ｃａｌｏｐｔｉｌｉａ　ｔｈｅｉｖｏｒａ）、キンモンホソガ（Ｐｈｙｌｌｏｎｏｒｙｃｔｅｒ　ｒｉｎｇｏｎｅｅｌｌａ）のホソガ類、モモシンクイガ（Ｃａｒｐｏｓｉｎａ　ｎｉｐｏｎｅｎｓｉｓ）等のシンクイガ類、リオネティア属等のハモグリガ類、リマントリア属、ユープロクティス属等のドクガ類、コナガ（Ｐｌｕｔｅｌｌａ　ｘｙｌｏｓｔｅｌｌａ）等のスガ類、ワタアカミムシ（Ｐｅｃｔｉｎｏｐｈｏｒａ　ｇｏｓｓｙｐｉｅｌｌａ）ジャガイモガ（Ｐｈｔｈｏｒｉｍａｅａ　ｏｐｅｒｃｕｌｅｌｌａ）等のキバガ類、アメリカシロヒトリ（Ｈｙｐｈａｎｔｒｉａ　ｃｕｎｅａ）等のヒトリガ類、及びイガ（Ｔｉｎｅａ　ｔｒａｎｓｌｕｃｅｎｓ）、コイガ（Ｔｉｎｅｏｌａ　ｂｉｓｓｅｌｌｉｅｌｌａ）等のヒロズコガ類等。 Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (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), Common moths such as Shibatatsuga (Pediasia teterrellus), Lotus moth (Spodoptera litura), Spodoptera exigua, Ayuyotoga (Pseudaletia separata), Yotoga Mestra brassicae, Agrotis ipsilon, Tamanagine waba (Plusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc. (Leguminivora, Glycinivolorella), Azusayamamushiga (Matsumuraeses azukikivora), Apple Kokukumonamaki (Adoxophyes orana fasciata), Chanokokumonmonakimohamaki (Adohomochamaki). ), Leafhoppers such as Archipes fuscocuppreanus, Cydonia pomonella, etc. Spiders such as leaf moths, Limantria, Euprocutis, etc., Suga such as Plutella xylostella, Pterinophora gossypiella, Phythromea operphylla such as Phythoreaea operculella Hitrigues such as ia cunea, and Hirokosukoga such as iga (Tinea translucens), Koiga (Tineola bisselliella) and the like.
　アザミウマ目害虫：ミカンキイロアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｏｃｃｉｄｅｎｔａｌｉｓ）、ミナミキイロアザミウマ（Ｔｈｒｉｐｓ　ｐａｒｍｉ）、チャノキイロアザミウマ（Ｓｃｉｒｔｏｔｈｒｉｐｓ　ｄｏｒｓａｌｉｓ）、ネギアザミウマ（Ｔｈｒｉｐｓ　ｔａｂａｃｉ）、ヒラズハナアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｉｎｔｏｎｓａ）などのアザミウマ類等。 Thrips of the order Thrips thrips, Sriptotrips dorsalis, Sriptorips dorsalis
　双翅目害虫：アカイエカ（Ｃｕｌｅｘ　ｐｉｐｉｅｎｓ　ｐａｌｌｅｎｓ）、コガタアカイエカ（Ｃｕｌｅｘ　ｔｒｉｔａｅｎｉｏｒｈｙｎｃｈｕｓ）、ネッタイイエカ（Ｃｕｌｅｘ　ｑｕｉｎｑｕｅｆａｓｃｉａｔｕｓ）等のイエカ類、ネッタイシマカ（Ａｅｄｅｓ　ａｅｇｙｐｔｉ）、ヒトスジシマカ（Ａｅｄｅｓ　ａｌｂｏｐｉｃｔｕｓ）等のエーデス属、シナハマダラカ（Ａｎｏｐｈｅｌｅｓ　ｓｉｎｅｎｓｉｓ）等のアノフェレス属、ユスリカ類、イエバエ（Ｍｕｓｃａ　ｄｏｍｅｓｔｉｃａ）、オオイエバエ（Ｍｕｓｃｉｎａ　ｓｔａｂｕｌａｎｓ）等のイエバエ類、クロバエ類、ニクバエ類、ヒメイエバエ類、タネバエ（Ｄｅｌｉａ　ｐｌａｔｕｒａ）、タマネギバエ（Ｄｅｌｉａ　ａｎｔｉｑｕａ）等のハナバエ類、イネハモグリバエ（Ａｇｒｏｍｙｚａ　ｏｒｙｚａｅ）、イネヒメハモグリバエ（Ｈｙｄｒｅｌｌｉａ　ｇｒｉｓｅｏｌａ）、トマトハモグリバエ、（Ｌｉｒｉｏｍｙｚａ　ｓａｔｉｖａｅ）、マメハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｔｒｉｆｏｌｉｉ）、ナモグリバエ（Ｃｈｒｏｍａｔｏｍｙｉａ　ｈｏｒｔｉｃｏｌａ）等のハモグリバエ類、イネキモグリバエ（Ｃｈｌｏｒｏｐｓ　ｏｒｙｚａｅ）等のキモグリバエ類、ウリミバエ（Ｄａｃｕｓ　ｃｕｃｕｒｂｉｔａｅ）、チチュウカイミバエ（Ｃｅｒａｔｉｔｉｓ　ｃａｐｉｔａｔａ）等のミバエ類、ショウジョウバエ類、オオキモンノミバエ（Ｍｅｇａｓｅｌｉａ　ｓｐｉｒａｃｕｌａｒｉｓ）等のノミバエ類、オオチョウバエ（Ｃｌｏｇｍｉａ　ａｌｂｉｐｕｎｃｔａｔａ）等のチョウバエ類、ブユ類、ウシアブ（Ｔａｂａｎｕｓ　ｔｒｉｇｏｎｕｓ）等のアブ類、及びサシバエ類等。 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. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc. Moguribae (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, fleas such as Megaselia spiracularis, Clogmial etc. Flies such, blackfly acids, Abu such as gadfly (Tabanus trigonus), and stable flies and the like.
　鞘翅目害虫：ウエスタンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｖｉｒｇｉｆｅｒａ　ｖｉｒｇｉｆｅｒａ）、サザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｕｎｄｅｃｉｍｐｕｎｃｔａｔａ　ｈｏｗａｒｄｉ）等のコーンルートワーム類、ドウガネブイブイ（Ａｎｏｍａｌａ　ｃｕｐｒｅａ）、ヒメコガネ（Ａｎｏｍａｌａ　ｒｕｆｏｃｕｐｒｅａ）、マメコガネ（Ｐｏｐｉｌｌｉａ　ｊａｐｏｎｉｃａ）等のコガネムシ類、メイズウィービル（Ｓｉｔｏｐｈｉｌｕｓ　ｚｅａｍａｉｓ）、イネミズゾウムシ（Ｌｉｓｓｏｒｈｏｐｔｒｕｓ　ｏｒｙｚｏｐｈｉｌｕｓ）、アズキゾウムシ（Ｃａｌｌｏｓｏｂｒｕｃｈｕｙｓ　ｃｈｉｅｎｅｎｓｉｓ）、イネゾウムシ（Ｅｃｈｉｎｏｃｎｅｍｕｓ　ｓｑｕａｍｅｕｓ）、ワタミゾウムシ（Ａｎｔｈｏｎｏｍｕｓ　ｇｒａｎｄｉｓ）、シバオサゾウムシ（Ｓｐｈｅｎｏｐｈｏｒｕｓ　ｖｅｎａｔｕｓ）等のゾウムシ類、チャイロコメノゴミムシダマシ（Ｔｅｎｅｂｒｉｏ　ｍｏｌｉｔｏｒ）、コクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ　ｃａｓｔａｎｅｕｍ）等のゴミムシダマシ類、イネドロオイムシ（Ｏｕｌｅｍａ　ｏｒｙｚａｅ）、ウリハムシ（Ａｕｌａｃｏｐｈｏｒａ　ｆｅｍｏｒａｌｉｓ）、キスジノミハムシ（Ｐｈｙｌｌｏｔｒｅｔａ　ｓｔｒｉｏｌａｔａ）、コロラドハムシ（Ｌｅｐｔｉｎｏｔａｒｓａ　ｄｅｃｅｍｌｉｎｅａｔａ）等のハムシ類、ヒメマルカツオブシムシ（Ａｎｔｈｒｅｎｕｓ　ｖｅｒｂａｓｃｉ）、ハラジロカツオブシムシ（Ｄｅｒｍｅｓｔｅｓ　ｍａｃｕｌａｔｅｓ）等のカツオブシムシ類、タバコシバンムシ（Ｌａｓｉｏｄｅｒｍａ　ｓｅｒｒｉｃｏｒｎｅ）等のシバンムシ類、ニジュウヤホシテントウ（Ｅｐｉｌａｃｈｎａ　ｖｉｇｉｎｔｉｏｃｔｏｐｕｎｃｔａｔａ）等のエピラクナ類、ヒラタキクイムシ（Ｌｙｃｔｕｓ　ｂｒｕｎｎｅｕｓ）、マツノキクイムシ（Ｔｏｍｉｃｕｓ　ｐｉｎｉｐｅｒｄａ）等のキクイムシ類、ナガシンクイムシ類、ヒョウホンムシ類、ゴマダラカミキリ（Ａｎｏｐｌｏｐｈｏｒａ　ｍａｌａｓｉａｃａ）等のカミキリムシ類、コメツキムシ類（Ａｇｒｉｏｔｅｓ　ｓｐｐ．）、及びアオバアリガタハネカクシ（Ｐａｅｄｅｒｕｓ　ｆｕｓｃｉｐｅｓ）等。 Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Maizeweville (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Azuki weevil (Callosobrchuchus chiensis), Rice weevil (Echinocnemus squatius) Weevil (Anthonomus grandis), Weevil weevil (Sphenophorus venatus) and other weevil, Tenebrio molitor, Aureum oleume olium (Olymoidum) Leaf beetles such as Phyllotreta striola, Colorado potato beetle (Leptinotarsa decemlineata), Japanese beetle ant beetle (Anthrenus versaci), Dermatodes sulculates, etc. Shimushi, Shibamushi (Lasiderma serricorne), etc .; Japanese beetles, longicorn beetles such as Anophorora malasiaca, click beetles (Agriotes spp.), And long-horned beetle (Paederus fuscipes).
　直翅目害虫：トノサマバッタ（Ｌｏｃｕｓｔａ　ｍｉｇｒａｔｏｒｉａ）、ケラ（Ｇｒｙｌｌｏｔａｌｐａ　ａｆｒｉｃａｎａ）、コバネイナゴ（Ｏｘｙａ　ｙｅｚｏｅｎｓｉｓ）、ハネナガイナゴ（Ｏｘｙａ　ｊａｐｏｎｉｃａ）、及びコオロギ類等。 Pterodoptera: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, Oroja japonica, etc.
　隠翅目害虫：ネコノミ（Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ　ｆｅｌｉｓ）、イヌノミ（Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ　ｃａｎｉｓ）、ヒトノミ（Ｐｕｌｅｘ　ｉｒｒｉｔａｎｓ）、ケオプスネズミノミ（Ｘｅｎｏｐｓｙｌｌａ　ｃｈｅｏｐｉｓ）等。 Insect pests: cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mouse fleas (Xenopsilla cheopes) and the like.
　シラミ目害虫：コロモジラミ（Ｐｅｄｉｃｕｌｕｓ　ｈｕｍａｎｕｓ　ｃｏｒｐｏｒｉｓ）、ケジラミ　（Ｐｈｔｈｉｒｕｓ　ｐｕｂｉｓ）、ウシジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｅｕｒｙｓｔｅｒｎｕｓ）、ヒツジジラミ（Ｄａｌｍａｌｉｎｉａ　ｏｖｉｓ）、ブタジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｓｕｉｓ）等。 Lice insect pests: Japanese lice (Pediculus humnus corporis), pheasants (Phythrus pubis), cattle lice (Haematopinus eurysternus), sheep lice (Dalmalinia ostois aus pis)
　膜翅目害虫：　イエヒメアリ（Ｍｏｎｏｍｏｒｉｕｍ　ｐｈａｒａｏｓｉｓ）、クロヤマアリ（Ｆｏｒｍｉｃａ　ｆｕｓｃａ　ｊａｐｏｎｉｃａ）、ルリアリ（Ｏｃｈｅｔｅｌｌｕｓ　ｇｌａｂｅｒ）、アミメアリ（Ｐｒｉｓｔｏｍｙｒｍｅｘ　ｐｕｎｇｅｎｓ）、オオズアリ（Ｐｈｅｉｄｏｌｅ　ｎｏｄａ）、ハキリアリ（Ａｃｒｏｍｙｒｍｅｘ　ｓｐｐ．）、ファイヤーアント（Ｓｏｌｅｎｏｐｓｉｓ　ｓｐｐ．）等のアリ類、スズメバチ類、アリガタバチ類、カブラハバチ（Ａｔｈａｌｉａ　ｒｏｓａｅ）、ニホンカブラバチ（Ａｔｈａｌｉａ　ｊａｐｏｎｉｃａ）等のハバチ類等。 Hymenoptera: Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Such as ants, hornets, hornets, bees (Athalia rosae), Japanese bees (Athalia japonica), and the like.
　ゴキブリ目害虫：チャバネゴキブリ（Ｂｌａｔｔｅｌｌａ　ｇｅｒｍａｎｉｃａ）、クロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｆｕｌｉｇｉｎｏｓａ）、ワモンゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ａｍｅｒｉｃａｎａ）、トビイロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｂｒｕｎｎｅａ）、トウヨウゴキブリ（Ｂｌａｔｔａ　ｏｒｉｅｎｔａｌｉｓ）等。 Cockroach eye pests: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta fuliginosa), Cockroach cockroach (Periplaneta americana), Japanese cockroach (Peripraneta bruna)
　シロアリ目害虫：ヤマトシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｓｐｅｒａｔｕｓ）、イエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、アメリカカンザイシロアリ（Ｉｎｃｉｓｉｔｅｒｍｅｓ　ｍｉｎｏｒ）、ダイコクシロアリ（Ｃｒｙｐｔｏｔｅｒｍｅｓ　ｄｏｍｅｓｔｉｃｕｓ）、タイワンシロアリ（Ｏｄｏｎｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、コウシュンシロアリ（Ｎｅｏｔｅｒｍｅｓ　ｋｏｓｈｕｎｅｎｓｉｓ）、サツマシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ　ｓａｔｓｕｍｅｎｓｉｓ）、ナカジマシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ　ｎａｋａｊｉｍａｉ）、カタンシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ　ｆｕｓｃｕｓ）、コダマシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ　ｋｏｄａｍａｉ）、クシモトシロアリ（Ｇｌｙｐｔｏｔｅｒｍｅｓ　ｋｕｓｈｉｍｅｎｓｉｓ）、オオシロアリ（Ｈｏｄｏｔｅｒｍｏｐｓｉｓ　ｊａｐｏｎｉｃａ）、コウシュウイエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ　ｇｕａｎｇｚｈｏｅｎｓｉｓ）、アマミシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｍｉｙａｔａｋｅｉ）、キアシシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｆｌａｖｉｃｅｐｓ　ａｍａｍｉａｎｕｓ）、カンモンシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｓｐ．）、タカサゴシロアリ（Ｎａｓｕｔｉｔｅｒｍｅｓ　ｔａｋａｓａｇｏｅｎｓｉｓ）、ニトベシロアリ（Ｐｅｒｉｃａｐｒｉｔｅｒｍｅｓ　ｎｉｔｏｂｅｉ）、ムシャシロアリ（Ｓｉｎｏｃａｐｒｉｔｅｒｍｅｓ　ｍｕｓｈａｅ）、Ｒｅｔｉｃｕｌｉｔｅｒｕｍｅｓ　ｆｌａｖｉｐｅｓ、Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｈｅｓｐｅｒｕｓ、Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｖｉｒｇｉｎｉｃｕｓ、Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｔｉｂｉａｌｉｓ、Ｈｅｔｅｒｏｔｅｒｍｅｓ　ａｕｒｅｕｓ、Ｚｏｏｔｅｒｍｏｐｓｉｓ　ｎｅｖａｄｅｎｓｉｓ等。 Termite pests: Yamato termites (Reticulitermes supertus), Japanese termites (Coptothermes formosanus), American white termites (Incitermes minors), Cyptotermes domesticus, Glypoptermes satsumensis, Gyptotermes nakajimai, Caterpillars (Glyptotermes fuscus), Termites (Glypoptermes kodamai), Shimotoshiroari (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis ), Termites termites (Pericapritermes nitobei), termites termites (Sinocapriters mushae), Reticulitermes fl ipes, Reticulitermes hesperus, Reticulitermes virginicus, Reticulitermes tibialis, Heterotermes aureus, Zootermopsis nevadensis or the like.
　ダニ目害虫：ナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｕｒｔｉｃａｅ）、カンザワハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｋａｎｚａｗａｉ）、ミカンハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｃｉｔｒｉ）リンゴハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｕｌｍｉ）、オリゴニカス属等のハダニ類、ミカンサビダニ（Ａｃｕｌｏｐｓ　ｐｅｌｅｋａｓｓｉ）、リュウキュウミカンサビダニ（Ｐｈｙｌｌｏｃｏｐｔｒｕｔａ　ｃｉｔｒｉ）、トマトサビダニ（Ａｃｕｌｏｐｓ　ｌｙｃｏｐｅｒｓｉｃｉ）、チャノサビダニ（Ｃａｌａｃａｒｕｓ　ｃａｒｉｎａｔｕｓ）、チャノナガサビダニ（Ａｃａｐｈｙｌｌａ　ｔｈｅａｖａｇｒａｎｓ）、ニセナシサビダニ（Ｅｒｉｏｐｈｙｅｓ　ｃｈｉｂａｅｎｓｉｓ）、リンゴサビダニ（Ａｃｕｌｕｓ　ｓｃｈｌｅｃｈｔｅｎｄａｌｉ）等のフシダニ類、チャノホコリダニ（Ｐｏｌｙｐｈａｇｏｔａｒｓｏｎｅｍｕｓ　ｌａｔｕｓ）等のホコリダニ類、ミナミヒメハダニ（Ｂｒｅｖｉｐａｌｐｕｓ　ｐｈｏｅｎｉｃｉｓ）等のヒメハダニ類、ケナガハダニ類、フタトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｌｏｎｇｉｃｏｒｎｉｓ）、ヤマトチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｆｌａｖａ）、タイワンカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｔａｉｗａｎｉｃｕｓ）、ヤマトマダニ（Ｉｘｏｄｅｓ　ｏｖａｔｕｓ）、シュルツマダニ（Ｉｘｏｄｅｓ　ｐｅｒｓｕｌｃａｔｕｓ）、ブラックレッグドチック（Ｉｘｏｄｅｓ　ｓｃａｐｕｌａｒｉｓ）、オウシマダニ（Ｂｏｏｐｈｉｌｕｓ　ｍｉｃｒｏｐｌｕｓ）、クリイロコイタマダニ（Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ｓａｎｇｕｉｎｅｕｓ）等のマダニ類、ケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｐｕｔｒｅｓｃｅｎｔｉａｅ）、ホウレンソウケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｓｉｍｉｌｉｓ）等のコナダニ類、コナヒョウヒダニ（Ｄｅｒｍａｔｏｐｈａｇｏｉｄｅｓ　ｆａｒｉｎａｅ）、ヤケヒョウヒダニ（Ｄｅｒｍａｔｏｐｈａｇｏｉｄｅｓ　ｐｔｒｅｎｙｓｓｎｕｓ）等のヒョウヒダニ類、ホソツメダニ（Ｃｈｅｙｌｅｔｕｓ　ｅｒｕｄｉｔｕｓ）、クワガタツメダニ（Ｃｈｅｙｌｅｔｕｓ　ｍａｌａｃｃｅｎｓｉｓ）、ミナミツメダニ（Ｃｈｅｙｌｅｔｕｓ　ｍｏｏｒｅｉ）等のツメダニ類、イエダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ　ｂａｃｏｔｉ）、トリサシダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ　ｓｙｌｖａｉｒｕｍ）、ワクモ（Ｄｅｒｍａｎｙｓｓｕｓ　ｇａｌｌｉｎａｅ）等のワクモ類、アオツツガムシ（Ｌｅｐｔｏｔｒｏｍｂｉｄｉｕｍ　ａｋａｍｕｓｈｉ）等のツツガムシ類、及びカバキコマチグモ（Ｃｈｉｒａｃａｎｔｈｉｕｍ　ｊａｐｏｎｉｃｕｍ）、セアカゴケグモ（Ｌａｔｒｏｄｅｃｔｕｓ　ｈａｓｓｅｌｔｉｉ）等のクモ類等。　　 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), Chanosabi mites (Calacarus carinatus), Chanogasabi mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple scab mites Achulus schizus endali) 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 (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), Tick ticks (Ixodes ovatus), Tick ticks (Ixodes persulcatus), Black legged ticks (Ixodes scapularis), Boophilus microplus, Rhipic mite (Rhipic) phalus sanguineus) ticks such as, Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), house dust mite such as pteronyssinus (Dermatophagoides ptrenyssnus), Hosotsumedani (Cheyletus eruditus), Stag Tsumedani ( Tilet mites, such as Cheyletus malaccensis, and Mite thorny (Cheyletus moorei), house dust mite (Ornithonysus bacoti), bird mite (Ornithonysus sylvairum) , Cucumbers such as Dermanysusus gallinae, tsutsugamushi such as Leptotropidum akamushi, and Chiracantium japonicum etc. *
　唇脚綱類：ゲジ（Ｔｈｅｒｅｕｏｎｅｍａ　ｈｉｌｇｅｎｄｏｒｆｉ）、トビズムカデ（Ｓｃｏｌｏｐｅｎｄｒａ　ｓｕｂｓｐｉｎｉｐｅｓ）等。 Lip limb class: Geji (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes), etc.
　倍脚綱類：ヤケヤスデ（Ｏｘｉｄｕｓ　ｇｒａｃｉｌｉｓ）、アカヤスデ（Ｎｅｄｙｏｐｕｓ　ｔａｍｂａｎｕｓ）等。 Double-legged class: Oxidus gracilis, Nadeyopus tambanus, etc.
　等脚目類：オカダンゴムシ（Ａｒｍａｄｉｌｌｉｄｉｕｍ　ｖｕｌｇａｒｅ）等。 Isopods: Armadillium vulgare, etc.
　腹足綱類：チャコウラナメクジ（Ｌｉｍａｘ　ｍａｒｇｉｎａｔｕｓ）、キイロコウラナメクジ（Ｌｉｍａｘ　ｆｌａｖｕｓ）等。 Gastropods: Limax marginatus, Limax flavus, etc.
　線虫類：イネシンガレセンチュウ（Ａｐｈｅｌｅｎｃｈｏｉｄｅｓ　ｂｅｓｓｅｙｉ）、イチゴメセンチュウ（Ｎｏｔｈｏｔｙｌｅｎｃｈｕｓ　ａｃｒｉｓ）、サツマイモネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｉｎｃｏｇｎｉｔａ）、キタネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｈａｐｌａ）、ジャワネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｊａｖａｎｉｃａ）、ダイズシストセンチュウ（Ｈｅｔｅｒｏｄｅｒａ　ｇｌｙｃｉｎｅｓ）、ジャガイモシストセンチュウ（Ｇｌｏｂｏｄｅｒａ　ｒｏｓｔｏｃｈｉｅｎｓｉｓ）、ミナミネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｃｏｆｆｅａｅ）、ムギネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｎｅｇｌｅｃｔｕｓ）等。 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 nectar (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus) and the like.
　本発明の有害生物防除剤は、本発明化合物と不活性担体とを含有する。本発明の有害生物防除剤は、通常、本発明化合物と固体担体、液体担体、ガス状担体等の不活性担体とを混合し、必要に応じて界面活性剤、その他の製剤用補助剤を添加して、乳剤、油剤、粉剤、粒剤、水和剤、フロアブル剤、マイクロカプセル剤、エアゾール剤、燻煙剤、毒餌剤、樹脂製剤等に製剤化されている。 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, liquid carrier, gaseous carrier, etc., and if necessary, a surfactant and other formulation adjuvants are added. Thus, they are formulated into emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smoke agents, poison baits, resin formulations and the like.
　本発明の有害生物防除剤は、本発明化合物を通常０．０１～９５重量％含有する。 The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
　製剤化の際に用いられる固体担体としては、例えば粘土類（カオリンクレー、珪藻土、ベントナイト、フバサミクレー、酸性白土等）、合成含水酸化珪素、タルク、セラミック、その他の無機鉱物（セリサイト、石英、硫黄、活性炭、炭酸カルシウム、水和シリカ等）、化学肥料（硫安、燐安、硝安、尿素、塩安等）等の微粉末及び粒状物等があげられる。 Examples of 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). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine fertilizers such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.) and granular materials.
　液体担体としては、例えば水、アルコール類（メタノール、エタノール、イソプロピルアルコール、ブタノール、ヘキサノール、ベンジルアルコール、エチレングリコール、プロピレングリコール、フェノキシエタノール等）、ケトン類（アセトン、メチルエチルケトン、シクロヘキサノン等）、芳香族炭化水素類（トルエン、キシレン、エチルベンゼン、ドデシルベンゼン、フェニルキシリルエタン、メチルナフタレン等）、脂肪族炭化水素類（ヘキサン、シクロヘキサン、灯油、軽油等）、エステル類（酢酸エチル、酢酸ブチル、ミリスチン酸イソプロピル、オレイン酸エチル、アジピン酸ジイソプロピル、アジピン酸ジイソブチル、プロピレングリコールモノメチルエーテルアセテート等）、ニトリル類（アセトニトリル、イソブチロニトリル等）、エーテル類（ジイソプロピルエーテル、１，４－ジオキサン、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテル、３－メトキシ－３－メチル－１－ブタノール等）、酸アミド類（Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等）、ハロゲン化炭化水素類（ジクロロメタン、トリクロロエタン、四塩化炭素等）、スルホキシド類（ジメチルスルホキシド等）、炭酸プロピレン及び植物油（大豆油、綿実油等）が挙げられる。 Examples of liquid carriers 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. (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyrate) Nitriles), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).
　ガス状担体としては、例えばフルオロカーボン、ブタンガス、ＬＰＧ（液化石油ガス）、ジメチルエーテル及び炭酸ガスが挙げられる。 Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
　界面活性剤としては、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリエチレングリコール脂肪酸エステル、等の非イオン界面活性剤、及びアルキルスルホン酸塩、アルキルベンゼンスルホン酸塩、アルキル硫酸塩等の陰イオン界面活性剤が挙げられる。 Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether and polyethylene glycol fatty acid ester, and negative ions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. An ionic surfactant is mentioned.
　その他の製剤用補助剤としては、固着剤、分散剤、着色剤及び安定剤等、具体的には例えばカゼイン、ゼラチン、糖類（でんぷん、アラビアガム、セルロース誘導体、アルギン酸等）、リグニン誘導体、ベントナイト、合成水溶性高分子（ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等）、ＰＡＰ（酸性リン酸イソプロピル）、ＢＨＴ（２，６－ジ－tert－ブチル－４－メチルフェノール）、ＢＨＡ（２－tert－ブチル－４－メトキシフェノールと３－tert－ブチル－４－メトキシフェノールとの混合物）が挙げられる。 Examples of other adjuvants for preparation include fixing 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).
　本発明の有害生物防除方法は、本発明化合物の有効量を有害生物に直接、及び／又は、有害生物の生息場所（植物体、土壌、家屋内、動物体等）に施用することにより行われる。本発明の有害生物防除方法には、本発明化合物が通常本発明の有害生物防除剤の形態で用いられる。 The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention directly to pests and / or to habitats of pests (plants, soil, households, animal bodies, etc.). . In the pest control method of the present invention, the compound of the present invention is usually used in the form of the pest control agent of the present invention.
　本発明の有害生物防除剤を農業分野の有害生物防除に用いる場合、その施用量は１００００ｍ2あたりの本発明化合物量で１～１００００ｇである。本発明の有害生物防除剤が乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、本発明化合物の濃度が０．０１～１００００ｐｐｍとなるように水で希釈して施用し、粒剤、粉剤等は、通常、そのまま施用する。 When the pest control agent of the present invention is used for pest control in the agricultural field, the application amount is 1 to 10,000 g in the amount of the present compound per 10,000 m 2 . When the pest control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually applied after diluting with water so that the concentration of the compound of the present invention is 0.01 to 10,000 ppm. Granules, powders and the like are usually applied as they are.
　これらの製剤や製剤の水希釈液は、有害生物または有害生物から保護すべき作物等の植物に直接散布処理してもよく、また耕作地の土壌に生息する有害生物を防除するために、該土壌に処理してもよい。 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 the soil of cultivated land. You may process to soil.
　また、シート状やひも状に加工した樹脂製剤を作物に巻き付ける、作物近傍に張り渡す、株元土壌に敷く等の方法により処理することもできる。 Also, it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
　本発明の有害生物防除剤を家屋内に生息する有害生物の防除に用いる場合、その施用量は、面上に処理する場合は処理面積１ｍ2あたりの本発明化合物量で、通常、０．０１～１０００ｍｇであり、空間に処理する場合は処理空間１ｍ3あたりの本発明化合物量で、通常、０．０１～５００ｍｇである。本発明の有害生物防除剤が乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常本発明化合物の濃度が０．１～１０００ｐｐｍとなるように水で希釈して施用し、油剤、エアゾール剤、燻煙剤、毒餌剤等はそのまま施用する。 When the pest control agent of the present invention is used for controlling pests living in a house, the amount applied is the amount of the compound of the present invention per 1 m 2 of treatment area when treated on the surface, usually 0.01. In the case of treatment in a space, the amount of the compound of the present invention per 1 m 3 of the treatment space is usually 0.01 to 500 mg. When the pest control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the compound of the present invention is 0.1 to 1000 ppm, and applied. Apply oils, aerosols, smoke, poison baits, etc. as they are.
　本発明の有害生物防除剤は、下記「作物」が栽培されている農地で使用することができる。 The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.
　農作物：トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピーナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ、タバコ等。 Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
　野菜；ナス科野菜（ナス、トマト、ピーマン、トウガラシ、ジャガイモ等）、ウリ科野菜（キュウリ、カボチャ、ズッキーニ、スイカ、メロン等）、アブラナ科野菜（ダイコン、カブ、セイヨウワサビ、コールラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等）、キク科野菜（ゴボウ、シュンギク、アーティチョーク、レタス等）、ユリ科野菜（ネギ、タマネギ、ニンニク、アスパラガス）、セリ科野菜（ニンジン、パセリ、セロリ、アメリカボウフウ等）、アカザ科野菜（ホウレンソウ、フダンソウ等）、シソ科野菜（シソ、ミント、バジル等）、イチゴ、サツマイモ、ヤマノイモ、サトイモ等。 Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
　果樹：仁果類（リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等）、核果類（モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等）、カンキツ類（ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等）、堅果類（クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等）、液果類（ブルーベリー、クランベリー、ブラックベリー、ラズベリー等）、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ、アブラヤシ等。 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.
　果樹以外の樹木：チャ、クワ、花木類（サツキ、ツバキ、アジサイ、サザンカ、シキミ、サクラ、ユリノキ、サルスベリ、キンモクセイ等）、街路樹（トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ、ニレ、トチノキ等）、サンゴジュ、イヌマキ、スギ、ヒノキ、クロトン、マサキ、カナメモチ、等。 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, eel, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
　芝生：シバ類（ノシバ、コウライシバ等）、バミューダグラス類（ギョウギシバ等）、ベントグラス類（コヌカグサ、ハイコヌカグサ、イトコヌカグサ等）、ブルーグラス類（ナガハグサ、オオスズメノカタビラ等）、フェスク類（オニウシノケグサ、イトウシノケグサ、ハイウシノケグサ等）、ライグラス類（ネズミムギ、　ホソムギ等）、カモガヤ、オオアワガエリ等。 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.
　その他：花卉類（バラ、カーネーション、キク、トルコギキョウ、カスミソウ、ガーベラ、マリーゴールド、サルビア、ペチュニア、バーベナ、チューリップ、アスター、リンドウ、ユリ、パンジー、シクラメン、ラン、スズラン、ラベンダー、ストック、ハボタン、プリムラ、ポインセチア、グラジオラス、カトレア、デージー、シンビジューム、ベゴニア等）、バイオ燃料植物（ヤトロファ、クルカス、ベニバナ、アマナズナ類、スイッチグラス、ミスカンサス、クサヨシ、ダンチク、ケナフ、キャッサバ、ヤナギ、藻類等）、観葉植物等。 Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), biofuel plants (Jatropha, Curcas, safflower, Amanasuna, switchgrass, Miscanthus, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.), ornamental plants, etc. .
　「作物」には、遺伝子組換え作物も含まれる。 “Crop” includes genetically modified crops.
　本発明の有害生物防除剤は、他の殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、植物成長調節剤、除草剤及び共力剤と混用又は併用することができる。かかる殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、除草剤及び共力剤の有効成分の例を以下に示す。 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, herbicides and synergists are shown below.
　殺虫剤の有効成分
（１）カーバメート系化合物
アラニカルブ（Ａｌａｎｙｃａｒｂ）、アルジカルブ（Ａｌｄｉｃａｒｂ）、ベンダイオカルブ（Ｂｅｎｄｉｏｃａｒｂ）、ベンフラカルブ（Ｂｅｎｆｕｒａｃａｒｂ）、ブトカルボキシム（Ｂｕｔｏｃａｒｂｏｘｉｍ）、ブトキシカルボキシム（Ｂｕｔｏｘｙｃａｒｂｏｘｉｍ）、カルバリル（Ｃａｒｂａｒｙｌ＝ＮＡＣ）、カルボフラン（Ｃａｒｂｏｆｕｒａｎ）、カルボスルファン（Ｃａｒｂｏｓｕｌｆａｎ）、クロエトカルブ（Ｃｌｏｅｔｈｏｃａｒｂ）、エチオフェンカルブ（Ｅｔｈｉｏｆｅｎｃａｒｂ）、フェノブカルブ（Ｆｅｎｏｂｕｃａｒｂ＝ＢＰＭＣ）、フェノチオカルブ（Ｆｅｎｏｔｈｉｏｃａｒｂ）、フォルメタネート（Ｆｏｒｍｅｔａｎａｔｅ）、フラチオカルブ（Ｆｕｒａｔｈｉｏｃａｒｂ）、イソプロカルブ（Ｉｓｏｐｒｏｃａｒｂ＝ＭＩＰＣ）、メチオカルブ（Ｍｅｔｈｉｏｃａｒｂ）、メソミル（Ｍｅｔｈｏｍｙｌ）、メトルカルブ（Ｍｅｔｏｌｃａｒｂ）、オキサミル（Ｏｘａｍｙｌ）、ピリミカーブ（Ｐｉｒｉｍｉｃａｒｂ）、プロポキスル（Ｐｒｏｐｏｘｕｒ：ＰＨＣ）、チオジカルブ（Ｔｈｉｏｄｉｃａｒｂ）、チオファノクス（Ｔｈｉｏｆａｎｏｘ）、トリアザメート（Ｔｒｉａｚａｍａｔｅ）、トリメサカルブ（Ｔｒｉｍｅｔｈａｃａｒｂ）、ＸＭＣ、及びキシリルカルブ（Ｘｙｌｙｌｃａｒｂ）。
（２）有機リン系化合物
アセフェート（Ａｃｅｐｈａｔｅ）、アザメチホス（Ａｚａｍｅｔｈｉｐｈｏｓ）、アジンホスエチル（Ａｚｉｎｐｈｏｓ－ｅｔｈｙｌ）、アジンホスメチル（Ａｚｉｎｐｈｏｓ－ｍｅｔｈｙｌ）、カズサホス（Ｃａｄｕｓａｆｏｓ）、クロルエトキシホス（Ｃｈｌｏｒｅｔｈｏｘｙｆｏｓ）、クロルフェンビンホス（Ｃｈ１ｏｒｆｅｎｖｉｎｐｈｏｓ）、クロルメフォス（Ｃｈｌｏｒｍｅｐｈｏｓ）、クロルピリホス（Ｃｈｌｏｒｐｙｒｉｆｏｓ）、クロルピリホスメチル（Ｃｈｌｏｒｐｙｒｉｆｏｓ－ｍｅｔｈｙｌ）、クマフォス（Ｃｏｕｍａｐｈｏｓ）、シアノホス（Ｃｙａｎｏｐｈｏｓ＝ＣＹＡＰ）、デメトン－Ｓ－メチル（Ｄｅｍｅｔｏｎ－Ｓ－ｍｅｔｈｙｌ）、ダイアジノン（Ｄｉａｚｉｎｏｎ）、ジクロルボス（Ｄｉｃｈｌｏｒｖｏｓ＝ＤＤＶＰ）、ジクロトホス（Ｄｉｃｒｏｔｏｐｈｏｓ）、ジメトエート（Ｄｉｍｅｔｈｏａｔｅ）、ジメチルビンホス（Ｄｉｍｅｔｈｙｌｖｉｎｐｈｏｓ）、ジスルホトン（Ｄｉｓｕｌｆｏｔｏｎ）、ＥＰＮ、エチオン（Ｅｔｈｉｏｎ）、エトプロホス（Ｅｔｈｏｐｒｏｐｈｏｓ）、エトリムホス（Ｅｔｒｉｍｆｏｓ）、ファムファー（Ｆａｍｐｈｕｒ）、フェナミホス（Ｆｅｎａｍｉｐｈｏｓ）、フエニトロチオン（Ｆｅｎｉｔｒｏｔｈｉｏｎ＝ＭＥＰ）、フェンチオン（Ｆｅｎｔｈｉｏｎ＝ＭＰＰ）、ホスチアゼート（Ｆｏｓｔｈｉａｚａｔｅ）、ヘプテノホス（Ｈｅｐｔｅｎｏｐｈｏｓ）、イミサイホス（Ｉｍｉｃｙｆｏｓ）、イソフェンホス（Ｉｓｏｆｅｎｐｈｏｓ）、Ｉｓｏｐｒｏｐｙｌ　Ｏ－（ｍｅｔｈｏｘｙａｍｉｎｏｔｈｉｏ－ｐｈｏｓｐｈｏｒｙｌ）ｓａｌｉｃｙｌａｔｅ、イソキサチオン（Ｉｓｏｘａｔｈｉｏｎ）、マラチオン（Ｍａｌａｔｈｉｏｎ）、メカルバム（Ｍｅｃａｒｂａｍ）、メスルフェンホス（Ｍｅｓｕｌｆｅｎｆｏｓ）、メタミドホス（Ｍｅｔｈａｍｉｄｏｐｈｏｓ）、メチダチオン（Ｍｅｔｈｉｄａｔｈｉｏｎ＝ＤＭＴＰ）、メビンホス（Ｍｅｖｉｎｐｈｏｓ）、モノクロトホス（Ｍｏｎｏｃｒｏｔｏｐｈｏｓ）、ナレッド（Ｎａｌｅｄ：ＢＲＰ）、オメトエート（Ｏｍｅｔｈｏａｔｅ）、オキシデメトンメチル（Ｏｘｙｄｅｍｅｔｏｎ－ｍｅｔｈｙｌ）、パラチオン（Ｐａｒａｔｈｉｏｎ）、メチルパラチオン（Ｐａｒａｔｈｉｏｎ－ｍｅｔｈｙｌ）、フェントエート（Ｐｈｅｎｔｈｏａｔｅ＝ＰＡＰ）、フォレート（Ｐｈｏｒａｔｅ）、ホサロン（Ｐｈｏｓａｌｏｎｅ）、ホスメット（Ｐｈｏｓｍｅｔ＝ＰＭＰ）、フォスファミドン（Ｐｈｏｓｐｈａｍｉｄｏｎ）、ホキシム（Ｐｈｏｘｉｍ）、ピリミホスメチル（Ｐｉｒｉｍｉｐｈｏｓ－ｍｅｔｈｙ１）、プロフェノホス（Ｐｒｏｆｅｎｏｆｏｓ）、プロペタムホス（Ｐｒｏｐｅｔａｍｐｈｏｓ）、プロチオホス（Ｐｒｏｔｈｉｏｆｏｓ）、ピラクロホス（Ｐｙｒａｃｌｏｒｆｏｓ）、ピリダフェンチオン（Ｐｙｒｉｄａｆｅｎｔｈｉｏｎ）、キナルホス（Ｑｕｉｎａｌｐｈｏｓ）、スルフォテップ（Ｓｕｌｆｏｔｅｐ）、テブピリムホス（Ｔｅｂｕｐｉｒｉｍｆｏｓ）、テメホス（Ｔｅｍｅｐｈｏｓ）、テルブホス（Ｔｅｒｂｕｆｏｓ）、テトラクロルビンホス（Ｔｅｔｒａｃｈ１ｏｒｖｉｎｐｈｏｓ）、チオメトン（Ｔｈｉｏｍｅｔｏｎ）、トリアゾホス（Ｔｒｉａｚｏｐｈｏｓ）、トリクロルホン（Ｔｒｉｃｈｌｏｒｐｈｏｎ＝ＤＥＰ）、バミドチオン（Ｖａｍｉｄｏｔｈｉｏｎ）、リン化アルミニウム（Ａｌｕｍｉｎｉｕｍ　ｐｈｏｓｐｈｉｄｅ）、ブタチオホス（Ｂｕｔａｔｈｉｏｆｏｓ）、ＤＣＩＰ（Ｄｉｃｈｌｏｒｏｄｉｉｓｏｐｒｏｐｙｌ　ｅｔｈｅｒ）、ジクロフェンチオン（Ｄｉｃｈｌｏｆｅｎｔｈｉｏｎ＝ＥＣＰ）、ホルモチオン（Ｆｏｒｍｏｔｈｉｏｎ）、リン化水素（Ｈｙｄｒｏｇｅｎ　ｐｈｏｓｐｈｉｄｅ）、オキシデプロホス（Ｏｘｙｄｅｐｒｏｆｏｓ＝ＥＳＰ）、プロパホス（Ｐｒｏｐａｐｈｏｓ）、サリチオン（Ｓａｌｉｔｈｉｏｎ）、及びスルプロホス（Ｓｕｌｐｒｏｆｏｓ）。
（３）ピレスロイド化合物
　アクリナトリン（Ａｃｒｉｎａｔｈｒｉｎ）、アレスリン（Ａｌｌｅｔｈｒｉｎ）、ベンフルスリン（Ｂｅｎｆｌｕｔｈｒｉｎ）、ベータ－シフルトリン（Ｂｅｔａ－Ｃｙｆｌｕｔｈｒｉｎ）、ビフェントリン（Ｂｉｆｅｎｔｈｒｉｎ）、シクロプロトリン（Ｃｙｃｌｏｐｒｏｔｈｒｉｎ）、シフルトリン（Ｃｙｆｌｕｔｈｒｉｎ）、シハロトリン（Ｃｙｈａｌｏｔｈｒｉｎ）、シペルメトリン（Ｃｙｐｅｒｍｅｔｈｒｉｎ）、デルタメトリン（Ｄｅｌｔａｍｅｔｈｒｉｎ）、エスフェンバレレート（Ｅｓｆｅｎｖａｌｅｒａｔｅ）、エトフェンプロックス（Ｅｔｈｏｆｅｎｐｒｏｘ）、フェンプロパトリン（Ｆｅｎｐｒｏｐａｔｈｒｉｎ）、フェンバレレート（Ｆｅｎｖａｌｅｒａｔｅ）、フルシトリネート（Ｆｌｕｃｙｔｈｒｉｎａｔｅ）、フルフェンプロックス（Ｆｌｕｆｅｎｏｐｒｏｘ）、フルメスリン（Ｆｌｕｍｅｔｈｒｉｎ）、フルバリネート（Ｆｌｕｖａｌｉｎａｔｅ）、ハルフェンプロックス（Ｈａｌｆｅｎｐｒｏｘ）、イミプロトリン（Ｉｍｉｐｒｏｔｈｒｉｎ）、ペルメトリン（Ｐｅｒｍｅｔｈｒｉｎ）、プラレトリン（Ｐｒａｌｌｅｔｈｒｉｎ）、ピレトリン（Ｐｙｒｅｔｈｒｉｎｓ）、レスメトリン（Ｒｅｓｍｅｔｈｒｉｎ）、シグマ－サイパーメスリン（ｓｉｇｍａ－Ｃｙｐｅｒｍｅｔｈｒｉｎ）、シラフルオフェン（Ｓｉｌａｆｌｕｏｆｅｎ）、テフルトリン（Ｔｅｆｌｕｔｈｒｉｎ）、トラロメトリン（Ｔｒａｌｏｍｅｔｈｒｉｎ）、トランスフルトリン（Ｔｒａｎｓｆｌｕｔｈｒｉｎ）、テトラメトリン（Ｔｅｔｒａｍｅｔｈｒｉｎ）、フェノトリン（Ｐｈｅｎｏｔｈｒｉｎ）、シフェノトリン（Ｃｙｐｈｅｎｏｔｈｒｉｎ）、アルファシペルメトリン（ａｌｐｈａ－Ｃｙｐｅｒｍｅｔｈｒｉｎ）、ゼータシペルメトリン（ｚｅｔａ－Ｃｙｐｅｒｍｅｔｈｒｉｎ）、ラムダシハロトリン（ｌａｍｂｄａ－Ｃｙｈａｌｏｔｈｒｉｎ）、ガンマシハロトリン（ｇａｍｍａ－Ｃｙｈａｌｏｔｈｒｉｎ）、フラメトリン（Ｆｕｒａｍｅｔｈｒｉｎ）、タウフルバリネート（ｔａｕ－Ｆｌｕｖａｌｉｎａｔｅ）、メトフルトリン（Ｍｅｔｏｆｌｕｔｈｒｉｎ）、プロフルトリン（Ｐｒｏｆｌｕｔｈｒｉｎ）、ジメフルトリン（Ｄｉｍｅｆｌｕｔｈｒｉｎ）、プロトリフェンビュート（Ｐｒｏｔｒｉｆｅｎｂｕｔｅ）、２，３，５，６－テトラフルオロ－４－（メトキシメチル）ベンジル　（ＥＺ）－（１ＲＳ，３ＲＳ；１ＲＳ，３ＳＲ）－２，２－ジメチル－３－プロプ－１－エニルシクロプロパンカルボキシレート、２，３，５，６－テトラフルオロ－４－メチルベンジル　（ＥＺ）－（１ＲＳ，３ＲＳ；１ＲＳ，３ＳＲ）－２，２－ジメチル－３－プロプ－１－エニルシクロプロパンカルボキシレート、及び２，３，５，６－テトラフルオロ－４－（メトキシメチル）ベンジル　（１ＲＳ，３ＲＳ；１ＲＳ，３ＳＲ）－２，２－ジメチル－３－（２－メチル－１－プロペニル）シクロプロパンカルボキシレート等。
（４）ネライストキシン化合物
　カルタップ（Ｃａｒｔａｐ）、ベンスルタップ（Ｂｅｎｓｕ１ｔａｐ）、チオシクラム（Ｔｈｉｏｃｙｃｌａｍ）、チオスルタップ（Ｔｈｉｓｕｌｔａｐ）、モノスルタップ（Ｍｏｎｏｓｕｌｔａｐ）、及びビスルタップ（Ｂｉｓｕｌｔａｐ）。
（５）ネオニコチノイド化合物
　イミダクロプリド（Ｉｍｉｄａｃ１ｏｐｒｉｄ）、ニテンピラム（Ｎｉｔｅｎｐｙｒａｍ）、アセタミプリド（Ａｃｅｔａｍｉｐｒｉｄ）、チアメトキサム（Ｔｈｉａｍｅｔｈｏｘａｍ）、チアクロプリド（Ｔｈｉａｃｌｏｐｒｉｄ）、ジノテフラン（Ｄｉｎｏｔｅｆｕｒａｎ）、及びクロチアニジン（Ｃｌｏｔｈｉａｎｉｄｉｎ）。
（６）ベンゾイル尿素化合物
　ビストリフルロン（Ｂｉｓｔｒｉｆｌｕｒｏｎ）、クロルフルアズロン（Ｃｈｌｏｒｆｌｕａｚｕｒｏｎ）、ジフルベンズロン（Ｄｉｆｌｕｂｅｎｚｕｒｏｎ）、フルシクロクスロン（Ｆｌｕｃｙｃｌｏｘｕｒｏｎ）、フルフェノクスロン（Ｆｌｕｆｅｎｏｘｕｒｏｎ）、ヘキサフルムロン（Ｈｅｘａｆｌｕｍｕｒｏｎ）、ルフェヌロン（Ｌｕｆｅｎｕｒｏｎ）、ノバルロン（Ｎｏｖａｌｕｒｏｎ）、ノビフルムロン（Ｎｏｖｉｆｌｕｍｕｒｏｎ）、テフルベンズロン（Ｔｅｆｌｕｂｅｎｚｕｒｏｎ）、トリフルムロン（Ｔｒｉｆｌｕｍｕｒｏｎ）、及びフルアズロン（ｆｌｕａｚｕｒｏｎ）。
（７）フェニルピラゾール化合物
　アセトプロール（Ａｃｅｔｏｐｒｏｌｅ）、エチプロール（Ｅｔｈｉｐｒｏｌｅ）、フィプロニル（Ｆｉｐｒｏｎｉ１）、バニリプロール（Ｖａｎｉｌｉｐｒｏｌｅ）、ピリプロール（Ｐｙｒｉｐｒｏｌｅ）、及びピラフルプロール（Ｐｙｒａｆｌｕｐｒｏｌｅ）。
（８）Ｂｔトキシン殺虫剤
　バチルス・チューリンゲンシス菌由来の生芽胞および産生結晶毒素、並びにそれらの混合物。
（９）ヒドラジン化合物
　クロマフェノジド（Ｃｈｒｏｍａｆｅｎｏｚｉｄｅ）、ハロフェノジド（Ｈａｌｏｆｅｎｏｚｉｄｅ）、メトキシフェノジド（Ｍｅｔｈｏｘｙｆｅｎｏｚｉｄｅ）、及びテブフェノジド（Ｔｅｂｕｆｅｎｏｚｉｄｅ）。
（１０）有機塩素化合物
　アルドリン（Ａｌｄｒｉｎ）、ディルドリン（Ｄｉｅｌｄｒｉｎ）、ジエノクロル（Ｄｉｅｎｏｃｈｌｏｒ）、エンドスルファン（Ｅｎｄｏｓｕｌｆａｎ）、メトキシクロル（Ｍｅｔｈｏｘｙｃｈｌｏｒ）、クロルデン（Ｃｈｌｏｒｄａｎｅ）、及びＤＤＴ。
（１１）その他の殺虫剤有効成分
　マシン油（Ｍａｃｈｉｎｅ　ｏｉｌ）、硫酸ニコチン（Ｎｉｃｏｔｉｎｅ－ｓｕｌｆａｔｅ）、ニコチン（Ｎｉｃｏｔｉｎｅ）、アバメクチン（Ａｂａｍｅｃｔｉｎ）、エマメクチン安息香酸塩（Ｅｍａｍｅｃｔｉｎ－ｂｅｎｚｏａｔｅ）、ミルベメクチン（Ｍｉｌｂｅｍｅｃｔｉｎ）、レピメクチン（Ｌｅｐｉｍｅｃｔｉｎ）、スピノサッド（Ｓｐｉｎｏｓａｄ）、スピネトラム（Ｓｐｉｎｅｔｏｒａｍ）、インドキサカルブ（Ｉｎｄｏｘａｃａｒｂ）、メタフルミゾン（Ｍｅｔａｆｌｕｍｉｚｏｎｅ）、ブプロフェジン（Ｂｕｐｒｏｆｅｚｉｎ）、シロマジン（Ｃｙｒｏｍａｚｉｎｅ）、ハイドロプレン（Ｈｙｄｒｏｐｒｅｎｅ）、メトプレン（Ｍｅｔｈｏｐｒｅｎｅ）、キノプレン（Ｋｉｎｏｐｒｅｎｅ）、ピリプロキシフェン（Ｐｙｒｉｐｒｏｘｙｆｅｎ）、フェノキシカルブ（Ｆｅｎｏｘｙｃａｒｂ）、クロルフェナピル（Ｃｈｌｏｒｐｈｅｎａｐｙｒ）、ＤＮＯＣ、ジアフェンチウロン（Ｄｉａｆｅｎｔｈｉｕｒｏｎ）、ピメトロジン（Ｐｙｍｅｔｒｏｚｉｎｅ）、フロニカミド（Ｆｌｏｎｉｃａｍｉｄ）、ピリフルキナゾン（Ｐｙｒｉｆｌｕｑｕｉｎａｚｏｎｅ）、ピリダリル（Ｐｙｒｉｄａｌｙｌ）、トルフェンピラド（Ｔｏｌｆｅｎｐｙｒａｄ）、フルリムフェン（Ｆｌｕｒｉｍｆｅｎ）、フルフェネリム（Ｆｌｕｆｅｎｅｒｉｍ）、スピロテトラマット（Ｓｐｉｒｏｔｅｔｒａｍａｔ）、スピロメシフェン（Ｓｐｉｒｏｍｅｓｉｆｅｎ）、スルフォキサフロール（ｓｕｌｆｏｘａｆｌｏｒ）、クロラントラニリプロール（Ｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、シアントラニリプロール（Ｃｙａｎｔｒａｎｉｌｉｐｒｏｌｅ）、フルベンジアミド（Ｆｌｕｂｅｎｄｉａｍｉｄｅ）、
下記式（Ｋ）： Active Ingredients of Insecticide (1) Carbamate Compounds Alaniccarb, Aldicarb, Bendiocarb, Benfurcarb, Butocaboxim, Butoxycarbyl, Butoxycarboxyl = NAC), Carbofuran, Carbosulfan, Cloethocarb, Ethiofencarb, Fenobucarb (BPMC), Fenothiocarb (Fenothiocarb, Fenothiocarb) ratiocarb, isoprocarb (Isoprocarb = MIPC), methiocarb (Methiocarb), methomyl (Methomyl), metorcarb (Metocarb), oxamyl (Oxamyl), pirimicarb (Pro), propoxyl (Pro) ), Triazamate, Trimesacarb, XMC, and Xylylcarb.
(2) Organophosphorus compounds: Acetate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Kazusafos, Chlorethhosphine, Chlorethophos , Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos = CYAP, Demeton-S-methyl, Demethon-S Jiku Rubos (Dichlorvos = DDVP), Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Etoprofos, Ethoprophos ), Fenamiphos, Fennitrothion (MEP), Fenthion (MPP), Phosphiazate, Heptenophos (Imicyfos), Ifenfos (Ipofos) Ethoxyaminothio-phosphoryl) salicylate, isoxathion (Isoxathion), malathion (Malathion), mecarbam (Mecarbom), mesulfophos (Mesulfofos), methobin (Methodophos), methidophos (Methidophos) (Naled: BRP), Omethoate, Oxydemethon-methyl, Parathion, Methylparathion, Phenthoate = PAP Phorate, Phosalone, Phosmet = PMP, Phosphamidon, Phoxim, Pirimiphos-methi, Profenfos (Pro), Profenfos (Pro), Profenfos (Profenfos) , Pyrachlorfos, pyridafenthion, quinalphos, sulfotep, tebupyrimfos, temephos, terubfos, terbufos, terbufos, terbufos nphos), thiomethon (Thiomethon), triazophos (Triazophos), trichlorphone (TRICHPHORON = DEP), bamidthione (Vamidothion), aluminum phosphide (Phiothiophene), rothiophos Formothion, Hydrogen phosphide, Oxydeprofos (ESP), Propafos, Salithion, and Sulprofos.
(3) Pyrethroid compounds Acrinathrin, Allethrin, Benfluthrin, Beta-Cyfluthrin, Bifenthrin, Cycloprothrin, Cycloprothrin (Cycloprothrin, Cycloprothrin, Cycloprothrin) , Cypermethrin, Deltamethrin, Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Fulcitrate F lucytrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praletrin, prethrin. Resmethrin, Sigma-Cypermethrin, Silafluofen, Tefluthrin, Tralomethrin, Transfluthrin, Tetramethrin thrin), phenothrin, cyphenothrin, alpha-Cypermethrin, zeta-Cypermethrin, lambda cihalothrin (lambda-Cyhalothrin) ), Furamethrin, tau-fluvalinate, methofluthrin, profluthrin, dimethylfluthrin, trifluorophenbute5, protrifenbute5, protrifenbute5 4- (Methoxyme L) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4- (methoxymethyl) Benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate and the like.
(4) Nereistoxin compounds Cartap, Bensulpap, Thiocylam, Thiosultap, Monosultap, and Bisultap.
(5) Neonicotinoid compounds Imidacloprid (Imidac1oprid), Nitenpyram (Nitenpyram), Acetamiprid (Acetamiprid), Thiamethoxam (Thiamethoxam), Thiacloprid (An) and dinotefurin (in)
(6) Benzoylurea compounds Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexafluuron, Hexafluuron Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron, and fluazuuron.
(7) Phenylpyrazole compounds Acetoprole, Ethiprole, Fipronil, Vaniliprole, Pyriprole, and Pyrafluprole.
(8) Bt toxin insecticide Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof.
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds Aldrin, Dieldrin, Dienochlor, Endosulfan, Methoxychlor, Chlordane, and DDT.
(11) Other Insecticide Active Ingredients Machine oil (Machine oil), nicotine sulfate (Nicotine-sulfate), nicotine (Nicotine), abamectin (Abamectin), emamectin benzoate (Emamectin-benzoate), milbemectin (Milbemectin) (Lepidectin), Spinosad, Spinetoram, Indoxacarb, Metaflumizone, Buprofezine, Cyromene, Cyromene, Cyromene, Cyromene ), Pyriproxyfen, Phenoxycarb, Chlorphenapyr, DNOC, Diafenthiuron, Pymetrozine, Pymetrozine, Pymetrozine Tolfenpyrad, Flurimfen, Flufenerim, Spirotetramat, Spiromesifen, Sulfoxaflor, Chloranthrolitrol orantraniliprole, cyantraniliprole, fulvendiamide,
The following formula (K):
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000044
〔式中、
　Ｒ100は塩素原子、臭素原子またはトリフルオロメチル基を表し、
　Ｒ200は塩素原子、臭素原子またはメチル基を表し、
　Ｒ300は塩素原子、臭素原子またはシアノ基を表す。〕
で示される化合物、
下記式（Ｌ）： [Where,
R 100 represents a chlorine atom, a bromine atom or a trifluoromethyl group,
R 200 represents a chlorine atom, a bromine atom or a methyl group,
R 300 represents a chlorine atom, a bromine atom or a cyano group. ]
A compound represented by
The following formula (L):
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000045
〔式中、
　Ｒ1000は塩素原子、臭素原子またはヨウ素原子を表す。〕
で示される化合物、メトキサジアゾン（Ｍｅｔｏｘａｄｉａｚｏｎｅ）、スルフラミド（Ｓｕｌｆｌｕｒａｍｉｄ）、亜ヒ酸（Ａｒｓｅｎｉｃ　ａｃｉｄ）、ベンクロチアズ（Ｂｅｎｃｌｏｔｈｉａｚ）、石灰窒素（Ｃａｌｃｉｕｍ　ｃｙａｎａｍｉｄｅ）、石灰硫黄合剤（Ｃａｌｃｉｕｍ　ｐｏｌｙｓｕｌｆｉｄｅ）、メタム・アンモニウム（Ｍｅｔａｍ－ａｍｍｏｎｉｕｍ）、メタム・ナトリウム（Ｍｅｔａｍ－ｓｏｄｉｕｍ）、オレイン酸カリウム（Ｐｏｔａｓｓｉｕｍ　ｏｌｅａｔｅ）、硫黄（Ｓｕｌｆｕｒ）、及びトラロピリル（Ｔｒａｌｏｐｙｒｉｌ）。 [Where,
R 1000 represents a chlorine atom, a bromine atom or an iodine atom. ]
, Methoxadiazone, sulfuramide, arsenous acid, benclothiaz, lime nitrogen (Calcium flude) (Calcium flude) ammonium, Metam-sodium, Potassium oleate, Sulfur, and Tralopyril.
　殺ダニ剤の有効成分
アセキノシル（Ａｃｅｑｕｉｎｏｃｙｌ）、アミトラズ（Ａｍｉｔｒａｚ）、ベンゾキシメート（Ｂｅｎｚｏｘｉｍａｔｅ）、ビフェナゼート（Ｂｉｆｅｎａａｔｅ）、ブロモプロピレート（Ｂｒｏｍｏｐｒｏｐｙｌａｔｅ）、キノメチオネート（Ｃｈｉｎｏｍｅｔｈｉｏｎａｔ）、クロルベンジレート（Ｃｈｌｏｒｏｂｅｎｚｉｌａｔｅ）、ＣＰＣＢＳ（Ｃｈｌｏｒｆｅｎｓｏｎ）、クロフェンテジン（Ｃｌｏｆｅｎｔｅｚｉｎｅ）、シフルメトフェン（Ｃｙｆｌｕｍｅｔｏｆｅｎ）、ジコホル（Ｄｉｃｏｆｏｌ）、エトキサゾール（Ｅｔｏｘａｚｏｌｅ）、フェナザキン（Ｆｅｎａｚａｑｕｉｎ）、酸化フェンブタスズ（Ｆｅｎｂｕｔａｔｉｎ　ｏｘｉｄｅ）、フェノチオカルブ（Ｆｅｎｏｔｈｉｏｃａｒｂ）、フェンピロキシメート（Ｆｅｎｐｙｒｏｘｉｍａｔｅ）、フルアクリピリム（Ｆｌｕａｃｒｙｐｙｒｉｍ）、ヘキシチアゾクス（Ｈｅｘｙｔｈｉａｚｏｘ）、プロパルギット（Ｐｒｏｐａｒｇｉｔｅ＝ＢＰＰＳ）、ポリナクチン複合体（Ｐｏｌｙｎａｃｔｉｎｓ）、ピリダベン（Ｐｙｒｉｄａｂｅｎ）、ピリミジフェン（Ｐｙｒｉｍｉｄｉｆｅｎ）、テブフェンピラド（Ｔｅｂｕｆｅｎｐｙｒａｄ）、テトラジホン（Ｔｅｔｒａｄｉｆｏｎ）、スピロジクロフェン（Ｓｐｉｒｏｄｉｃｌｏｆｅｎ）、アミドフルメット（Ａｍｉｄｏｆｌｕｍｅｔ）、及びシエノピラフェン（ｃｙｅｎｏｐｙｒａｆｅｎ）。 Active ingredients of acaricides: Acequinocyl, Amitraz, Benzoximate, Bifenaate, Bromopropyl, BSPC, Chromethionate, Chromethionate ), Clofentezine, cyflumetofen, dicofol, etoxazole, fenazaquin, fenbutatin oxide, fenothiophen Pyroximate, Fluacrylpyrim, Hexythiaxox, propargite (di), di (R), pyridene (P), piridaben (Pyriben) Diclofen, Spirodiclofen, Amidoflumet, and Cyenopyrafen.
　殺線虫剤の有効成分
　臭化メチル（Ｍｅｔｈｙｌ　ｂｒｏｍｉｄｅ）、Ｄ－Ｄ（１，３－Ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、ＤＣＩＰ、フォスチアゼート（Ｆｏｓｔｈｉａｚａｔｅ）、塩酸レバミゾール（Ｌｅｖａｍｉｓｏｌ）、メチルイソチオシアネート（Ｍｅｔｈｙｉｓｏｔｈｉｏｃｙａｎａｔｅ）、酒石酸モランテル（Ｍｏｒａｎｔｅｌ　ｔａｒｔａｒａｔｅ）、及びイミシアホス（Ｉｍｉｃｙａｆｏｓ）。 Active ingredient of nematicide Methyl bromide, DD (1,3-Dichloropropene), DCIP, Fostiazate, levamisole hydrochloride, Levimisol, Methylisothiocyanate tartarate), and Imicyafos.
　殺菌剤の有効成分
　アザコナゾール（Ａｚａｃｏｎａｚｏｌｅ）、ビテルタノール（Ｂｉｔｅｒｔａｎｏｌ）、ブロムコナゾール（Ｂｒｏｍｕｃｏｎａｚｏｌｅ）、シプロコナゾール（Ｃｙｐｒｏｃｏｎａｚｏｌｅ）、ジフェノコナゾール（Ｄｉｆｅｎｏｃｏｎａｚｏｌｅ）、ジニコナゾールＭ（Ｄｉｎｉｃｏｎａｚｏｌｅ－Ｍ）、エポキシコナゾール（Ｅｐｏｘｉｃｏｎａｚｏｌｅ）、フェナリモル（Ｆｅｎａｒｉｍｏｌ）フェンブコナゾール（Ｆｅｎｂｕｃｏｎａｚｏｌｅ）、フルシラゾール（Ｆｌｕｓｉｌａｚｏｌｅ）、フルキンコナゾール（Ｆｌｕｑｕｉｎｃｏｎａｚｏｌｅ）、フルトリアホール（Ｆｌｕｔｒｉａｆｏｌ）、ヘキサコナゾール（Ｈｅｘａｃｏｎａｚｏｌｅ）、イマザリル（Ｉｍａｚａｌｉｌ）、イミベンコナゾール（Ｉｍｉｂｅｎｃｏｎａｚｏｌｅ）、イプコナゾール（Ｉｐｃｏｎａｚｏｌｅ）、メトコナゾール（Ｍｅｔｃｏｎａｚｏｌｅ）、ミクロブタニル（Ｍｙｃｌｏｂｕｔａｎｉｌ）、ヌアリモル（Ｎｕａｒｉｍｏｌ）、オキスポコナゾール（Ｏｘｐｏｃｏｎａｚｏｌｅ）、ペフラゾエート（Ｐｅｆｕｒａｚｏａｔｅ）、ペンコナゾール（Ｐｅｎｃｏｎａｚｏｌｅ）、プロクロラズ（Ｐｒｏｃｈｌｏｒａｚ）、プロピコナゾール（Ｐｒｏｐｉｃｏｎａｚｏｌｅ）、プロチオコナゾール（Ｐｒｏｔｈｉｏｃｏｎａｚｏｌｅ）、ピリフェノクス（Ｐｙｒｉｆｅｎｏｘ）、シメコナゾール（Ｓｉｍｅｃｏｎａｚｏｌｅ）、テブコナゾール（Ｔｅｂｕｃｏｎａｚｏｌｅ）、テトラコナゾール（Ｔｅｔｒａｃｏｎａｚｏｌｅ）、トリアジメホン（Ｔｒｉａｄｉｍｅｆｏｎ）、トリアジメノール（Ｔｒｉａｄｉｍｅｎｏｌ）、トリフルミゾール（Ｔｒｉｆｌｕｍｉｚｏｌｅ）、トリホリン（Ｔｒｉｆｏｌｉｎ）、トリティコナゾール（Ｔｒｉｔｉｃｏｎａｚｏｌｅ）、アルジモルフ（Ａｌｄｉｍｏｒｐｈ）、ドデモルフ（Ｄｏｄｅｍｏｒｐｈ）、フェンプロピモルフ（Ｆｅｎｐｒｏｐｉｍｏｒｐｈ）、トリデモルフ（Ｔｒｉｄｅｍｏｒｐｈ）、フェンプロピジン（Ｆｅｎｐｒｏｐｉｄｉｎ）、ピペラリン（Ｐｉｐｅｒａｌｉｎ）、スピロキサミン（Ｓｐｉｒｏｘａｍｉｎｅ）、フェンヘキサミド（Ｆｅｎｈｅｘａｍｉｄｅ）、ピリブチカルブ（Ｐｙｒｉｂｕｔｉｃａｒｂ）、ナフチフィン（Ｎａｐｈｔｉｆｉｎｅ）、テルビナフィン（Ｔｅｒｂｉｎａｆｉｎｅ）等のステロール生合成阻害化合物；
　ベノミル（Ｂｅｎｏｍｙｌ）、カルベンダジム（Ｃａｒｂｅｎｄｅｚｉｍ）、フベリダゾール（Ｆｕｂｅｒｉｄａｚｏｌｅ）、チアベンダゾール（Ｔｈｉａｂｅｎｄａｚｏｌｅ）、チオファネート（Ｔｈｉｐｈａｎａｔｅ）、チオファネートメチル（ｔｈｉｏｐｈａｎａｔｅ－ｍｅｔｈｙｌ）、ジエトフェンカルブ（Ｄｉｅｔｈｏｆｅｎｃａｒｂ）、ゾキサミド（Ｚｏｘａｍｉｄｅ）ペンシクロン（Ｐｅｎｃｙｃｕｒｏｎ）、フルオピコリド（Ｆｌｕｏｐｉｃｏｌｉｄｅ）等の細胞***阻害殺菌化合物；
　クロゾリネート（Ｃｈｌｏｚｏｌｉｎａｔｅ）、イプロジオン（Ｉｐｒｏｄｉｏｎｅ）、プロシミドン（Ｐｒｏｃｙｍｉｄｏｎｅ）、ビンクロゾリン（Ｖｉｎｃｌｏｚｏｌｉｎ）、キノキシフェン（Ｑｕｉｎｏｘｙｆｅｎ）、プロキナジド（Ｐｒｏｑｕｉｎａｚｉｄ）、フェンピクロニル（Ｆｅｎｐｉｃｌｏｎｉｌ）、フルジオキソニル（Ｆｌｕｄｉｏｘｏｎｉｌ）等のシグナル伝達系阻害殺菌化合物；
　シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）、ピリメタニル（ｐｙｒｉｍｅｔｈａｎｉｌ）、メパニピリム（Ｍｅｐａｎｉｐｙｒｉｍ）等のアミノ酸生合成阻害殺菌化合物；
メタラキシル（Ｍｅｔａｌａｘｙｌ）、ベナラキシル（Ｂｅｎａｌａｘｙｌ）、オキソリニック酸（Ｏｘｏｌｉｎｉｃ　ａｃｉｄ）等の核酸生合成阻害殺菌化合物；
　イソプロチオラン（Ｉｓｏｐｒｏｔｈｉｏｌａｎｅ）、イプロベンホス（Ｉｐｒｏｂｅｎｆｏｓ）、トルクロホスメチル（Ｔｏｌｃｌｏｆｏｓ－ｍｅｔｈｙｌ）、プロチオカルブ（Ｐｒｏｔｈｉｏｃａｒｂ）、ジメトモルフ（Ｄｉｍｅｔｈｏｍｏｒｐｈ）、ベンチアバリカルブイソプロピル（Ｂｅｎｔｈｉａｖａｌｉｃａｒｂ－ｉｓｏｐｒｏｐｙｌ）、イプロバリカルブ（Ｉｐｒｏｖａｌｉｃａｒｂ）、マンジプロパミド（Ｍａｎｄｉｐｒｏｐａｍｉｄ）等の脂質・膜合成阻害殺菌化合物；
　ジクロシメット（Ｄｉｃｌｏｃｙｍｅｔ）、カルプロパミド（Ｃａｒｐｒｏｐａｍｉｄ）、フェノキサニル（Ｆｅｎｏｘａｎｉｌ）、フサライド（Ｆｔｈａｌｉｄｅ）、トリシクラゾール（Ｔｒｉｃｙｃｌａｚｏｌｅ）、ピロキロン（Ｐｙｒｏｑｕｉｌｏｎ）等のメラニン生合成阻害殺菌化合物；
　アゾキシストロビン（Ａｚｏｘｙｓｔｒｏｂｉｎ）、ジモキシストロビン（Ｄｉｍｏｘｙｓｔｒｏｂｉｎ）、エネストロビン（Ｅｎｅｓｔｒｏｂｉｎ）、フルオキサストロビン（Ｆｌｕｏｘａｓｔｒｏｂｉｎ）、クレソキシムメチル（Ｋｒｅｓｏｘｉｍ－ｍｅｔｈｙｌ）、メトミノストロビン（Ｍｅｔｏｍｉｎｏｓｔｒｏｂｉｎ）、オリサストロビン（Ｏｒｙｓａｓｔｒｏｂｉｎ）、ピコキシストロビン（Ｐｉｃｏｘｙｓｔｒｏｂｉｎ）、ピラクロストロビン（Ｐｙｒａｃｌｏｓｔｒｏｂｉｎ）、ピリベンカルブ（Ｐｙｒｉｂｅｎｃａｒｂ）トリフロキシストロビン（Ｔｒｉｆｌｏｘｙｓｔｒｏｂｉｎ）等のストロビルリン殺菌化合物；
カルボキシン（Ｃａｒｂｏｘｉｎ）、オキシカルボキシン（Ｏｘｙｃａｒｂｏｘｉｎ）、メプロニル（Ｍｅｐｒｏｎｉｌ）、フルトラニル（Ｆｌｕｔｏｒａｎｉｌ）、フラメトピル（Ｆｕｒａｍｅｔｏｐｙｒ）、チフルザミド（Ｔｈｉｆｌｕｚａｍｉｄｅ）、ボスカリド（Ｂｏｓｃａｌｉｄ）、ペンチオピラド（Ｐｅｎｔｈｉｏｐｙｒａｄ）、フルオピラム（Ｆｌｕｏｐｙｒａｍ）、ビキサフェン（Ｂｉｘａｆｅｎ）、イソピラザム（Ｉｓｏｐｙｒａｚａｍ）、ペンフルフェン（Ｐｅｎｆｌｕｆｅｎ）、セダキサン（Ｓｅｄａｘａｎ）、フルキサピロキサド（Ｆｌｕｘａｐｙｒｏｘａｄ）等のアニリド系殺菌化合物；
アシベンゾラールＳメチル（Ａｃｉｂｅｎｚｏｌａｒ－Ｓ－ｍｅｔｈｙｌ）、プロベナゾール（Ｐｒｏｂｅｎａｚｏｌｅ）、チアジニル（Ｔｉａｄｉｎｉｌ）、イソチアニル（Ｉｓｏｔｉａｎｉｌ）等の抵抗性誘導化合物；
　バリダマイシンＡ（Ｖａｌｉｄａｍｙｃｉｎ　Ａ）、ポリオキシンＢ（Ｐｏｌｙｏｘｉｎ　Ｂ）等のグルカン合成阻害殺菌化合物；
　ブラストサイジンＳ（Ｂｌａｓｔｃｉｄｉｎ－Ｓ）、カスガマイシン（Ｋａｓｕｇａｍｙｃｉｎ）、ストレプトマイシン（Ｓｔｒｅｐｔｏｍｙｃｉｎ）等のタンパク質生合成阻害殺菌化合物；
　チウラム（Ｔｈｉｕｒａｍ）、マンコゼブ（Ｍａｎｃｏｚｅｂ）、クロロタロニル（Ｃｈｌｏｒｏｔｈａｌｏｎｉｌ）、キャプタン（Ｃａｐｔａｎ）、ジクロフルアニド（Ｄｉｃｈｌｏｆｌｕａｎｉｄ）、フォルペット（Ｆｏｌｐｅｔ）、イミノクタジン（Ｉｍｉｎｏｃｔａｄｉｎｅ）、ジラム（Ｚｉｒａｍ）等のマルチサイト接触活性の殺菌化合物；
アミスルブロム（Ａｍｉｓｕｌｂｒｏｍ）；シアゾファミド（Ｃｙａｚｏｆａｍｉｄ）；フェリムゾン（Ｆｅｒｉｍｚｏｎｅ）；フルアジナム（Ｆｌｕａｚｉｎａｍ）；ビナパクリル（Ｂｉｎａｐａｃｒｙｌ）；ジノカップ（Ｄｉｎｏｃａｐ）；ファモキサドン（Ｆａｍｏｘａｄｏｎｅ）；フェナミドン（Ｆｅｎａｍｉｄｏｎｅ）；エタボキサム（Ｅｔｈａｂｏｘａｍ）；メトラフェノン（Ｍｅｔｒａｆｅｎｏｎｅ）；シフルフェナミド（Ｃｙｆｌｕｆｅｎａｍｉｄ）等。 Active ingredients of fungicides Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Difenaconol, Dinicoconol D, Iniconazole E (Fenarimol) Fenbuconazole, Flucilazole, Fluquinconazole, Flutriafol, Hexaconazole, Imazaril (Imazalil) Imibenconazole, Ipconazole, Iconconazole, Metconazole, Microbutanil, Nuarimol, Oxpoconazole, Puroazo Propiconazole, Prothioconazole, Pyrifenox, Simeconazole, Tebuconazole, Tetraconazole, Triazimone fon), triadimenol (Triadimenol), triflumizole (Triflumizole), trifolin (Trifolin), triticonazole (Triticonazole), aldimorph (Dodimorph), dodemorph (Morph) , Fenpropidin, Piperalin, Spiroxamine, Fenhexamide, Pyributicarb, Naftifine, Terbinafine (Terbinafine)
Benomyl, Carbendazim, Fuberidazole, Thiabendazole, Thiophaneate, Thiophaneate, ThiophanateMethyl, ThiophanateMethyl ) And other cell division inhibiting bactericidal compounds;
Clozolinate (Chlozolinate), Iprodione (Iprodione), Procymidone (Procymidone), Vinclozoline (Quinoxyfen), Proquinazin (Proquinodil), Fenpiclonil (Fenpiclonil)
Bactericidal compounds that inhibit amino acid biosynthesis such as cyprodinil, pyrimethanil, mepanipyrim;
Bactericidal compounds that inhibit nucleic acid biosynthesis, such as metalaxyl, benalaxyl, oxolinic acid;
Isoprothiolane (Iproprotiolane), Iprobenfos (Iprobenfos), Toluclofos-methyl (Prothiocarb), Dimethomorphic (Benthiatropiprob) Bactericidal compounds that inhibit lipid and membrane synthesis;
Melanin biosynthesis inhibiting bactericidal compounds such as diclocymet, carpropamide, phenoxanil, fthalide, tricyclazole, pyroquilon, etc .;
Azoxystrobin, dimoxystrobin, enestrobin, fluoxastrobin, cresoxime-methyl, methinostrobin (methominostrobin) Strobilurin bactericidal compounds such as Pyroxystrobin, Pyraclostrobin, Pyribencarb Trifloxystrobin;
Carboxin, Oxycarboxin, Mepronil, Flutolanil, Furametopyr, Thifluzamide, Flupy, penthirid, P Anilide bactericidal compounds such as Bixafen, Isopyrazam, Penflufen, Sedaxan, Fluxapyroxad;
Resistance-inducing compounds such as Acibenzolar-S-methyl, Probenazole, Tiadinil, Isotianil;
Glucan synthesis-inhibiting fungicidal compounds such as validamycin A and polyoxin B;
Protein biosynthesis inhibiting bactericidal compounds such as Blastcidin-S, Kasugamycin, Streptomycin, etc .;
Thiuram, Mancozeb, Chlorothalonil, Captan, Diclofluanid, Folpet, Iminoctaine, Bacteria of Ziram (Zira) Compound;
Amisulbrom; Cyazofamid; Ferimzone; Fluazinam; Binapacryl; Dinocapone; Famoxadone; Famoxadone; Cyflufenamide and the like.
　除草剤の有効成分
（１）フェノキシ脂肪酸除草性化合物
　２，４－ＰＡ、ＭＣＰ、ＭＣＰＢ、フェノチオール（Ｐｈｅｎｏｔｈｉｏ１）、メコプロップ（Ｍｅｃｏｐｒｏｐ）、フルロキシピル（Ｆｌｕｒｏｘｙｐｙｒ）、トリクロピル（Ｔｒｉｃｌｏｐｙｒ）、クロメプロップ（Ｃｌｏｍｅｐｒｏｐ）、及びナプロアニリド（Ｎａｐｒｏａｎｉｌｉｄｅ）。
（２）安息香酸除草性化合物
　２，３，６－ＴＢＡ、ジカンバ（Ｄｉｃａｍｂａ）、クロピラリド（Ｃｌｏｐｙｒａｌｉｄ）、ピクロラム（Ｐｉｃｌｏｒａｍ）、アミノピラリド（Ａｍｉｎｏｐｙｒａｌｉｄ）、キンクロラック（Ｑｕｉｎｃｌｏｒａｃ）、及びキンメラック（Ｑｕｉｎｍｅｒａｃ）。
（３）尿素除草性化合物
ジウロン（Ｄｉｕｒｏｎ）、リニュロン（Ｌｉｎｕｒｏｎ）、クロルトルロン（Ｃｈｌｏｒｔｏｌｕｒｏｎ）、イソプロツロン（Ｉｓｏｐｒｏｔｕｒｏｎ）、フルオメツロン（Ｆｌｕｏｍｅｔｕｒｏｎ）、イソウロン（Ｉｓｏｕｒｏｎ）、テブチウロン（Ｔｅｂｕｔｈｉｕｒｏｎ）、メタベンズチアズロン（Ｍｅｔｈａｂｅｎｚｔｈｉａｚｕｒｏｎ）、クミルロン（Ｃｕｍｙ１ｕｒｏｎ）、ダイムロン（Ｄａｉｍｕｒｏｎ）、及びメチルダイムロン（Ｍｅｔｈｙｌ－ｄａｉｍｕｒｏｎ）。
（４）トリアジン除草性化合物
　アトラジン（Ａｔｒａｚｉｎｅ）、アメトリン（Ａｍｅｔｏｒｙｎ）、シアナジン（Ｃｙａｎａｚｉｎｅ）、シマジン（Ｓｉｍａｚｉｎｅ）、プロパジン（Ｐｒｏｐａｚｉｎｅ）、シメトリン（Ｓｉｍｅｔｒｙｎ）、ジメタメトリン（Ｄｉｍｅｔｈａｍｅｔｒｙｎ）、プロメトリン（Ｐｒｏｍｅｔｒｙｎ）、メトリブジン（Ｍｅｔｒｉｂｕｚｉｎ）、トリアジフラム（Ｔｒｉａｚｉｆｌａｍ）、及びインダジフラム（Ｉｎｄａｚｉｆｌａｍ）。
（５）ビピリジニウム除草性化合物
　パラコート（Ｐａｒａｑｕａｔ）、及びジクワット（Ｄｉｑｕａｔ）。
（６）ヒドロキシベンゾニトリル除草性化合物
　ブロモキシニル（Ｂｒｏｍｏｘｙｎｉｌ）、及びアイオキシニル（Ｉｏｘｙｎｉｌ）。
（７）ジニトロアニリン除草性化合物
　ペンディメタリン（Ｐｅｎｄｉｍｅｔｈａｌｉｎ）、プロジアミン（Ｐｒｏｄｉａｍｉｎｅ）、及びトリフルラリン（Ｔｒｉｆｌｕｒａｌｉｎ）。
（８）有機リン除草性化合物
　アミプロホスメチル（Ａｍｉｐｒｏｆｏｓ－ｍｅｔｈｙｌ）、ブタミホス（Ｂｕｔａｍｉｆｏｓ）、ベンスリド（Ｂｅｎｓｕ１ｉｄｅ）、ピペロホス（Ｐｉｐｅｒｏｐｈｏｓ）、アニロホス（Ａｎｉｌｏｆｏｓ）、グリホサート（Ｇｌｙｐｈｏｓａｔｅ）、グルホシネート（Ｇｌｕｆｏｓｉｎａｔｅ）、グルホシネート－Ｐ（Ｇｌｕｆｏｓｉｎａｔｅ－Ｐ）、及びビアラホス（Ｂｉａｌａｐｈｏｓ）。
（９）カーバメート除草性化合物
　ジアレート（Ｄｉ－ａｌｌａｔｅ）、トリアレート（Ｔｒｉ－ａｌｌａｔｅ）、ＥＰＴＣ、ブチレート（Ｂｕｔｙｌａｔｅ）、ベンチオカーブ（Ｂｅｎｔｈｉｏｃａｒｂ）、エスプロカルブ（Ｅｓｐｒｏｃａｒｂ）、モリネート（Ｍｏｌｉｎａｔｅ）、ジメピペレート（Ｄｉｍｅｐｉｐｅｒａｔｅ）、スエップ（Ｓｗｅｐ）、クロルプロファム（Ｃｈｌｏｒｐｒｏｐｈａｍ）、フェンメディファム（Ｐｈｅｎｍｅｄｉｐｈａｍ）、フェニソファム（Ｐｈｅｎｉｓｏｐｈａｍ）、ピリブチカルブ（Ｐｙｒｉｂｕｔｉｃａｒｂ）、及びアシュラム（Ａｓｕｌａｍ）。
（１０）酸アミド除草性化合物
　プロパニル（Ｐｒｏｐａｎｉｌ）、プロピザミド（Ｐｒｏｐｙｚａｍｉｄｅ）、ブロモブチド（Ｂｒｏｍｏｂｕｔｉｄｅ）、及びエトベンザニド（Ｅｔｏｂｅｎｚａｎｉｄ）。
（１１）クロロアセトアニリド除草性化合物
　アセトクロール（Ａｃｅｔｏｃｈｌｏｒ）、アラクロール（Ａｌａｃｈｌｏｒ）、ブタクロール（Ｂｕｔａｃｈｌｏｒ）、ジメテナミド（Ｄｉｍｅｔｈｅｎａｍｉｄ）、プロパクロール（Ｐｒｏｐａｃｈｌｏｒ）、メタザクロール（Ｍｅｔａｚａｃｈｌｏｒ）、メトラクロール（Ｍｅｔｏｌａｃｈｌｏｒ）、プレチラクロール（Ｐｒｅｔｉｌａｃｈｌｏｒ）、テニルクロール（Ｔｈｅｎｙ１ｃｈ１ｏｒ）、及びペトキサミド（Ｐｅｔｈｏｘａｍｉｄ）。
（１２）ジフェニルエーテル除草性化合物
　アシフルオルフェン（Ａｃｉｆｌｕｏｒｆｅｎ－ｓｏｄｉｕｍ）、ビフェノックス（Ｂｉｆｅｎｏｘ）、オキシフルオルフェン（Ｏｘｙｆｌｕｏｒｆｅｎ）、ラクトフェン（Ｌａｃｔｏｆｅｎ）、フォメサフェン（Ｆｏｍｅｓａｆｅｎ）、クロメトキシニル（Ｃｈｌｏｍｅｔｈｏｘｙｎｉ１）、及びアクロニフェン（Ａｃｌｏｎｉｆｅｎ）。
（１３）環状イミド除草性化合物
　オキサジアゾン（Ｏｘａｄｉａｚｏｎ）、シニドンエチル（Ｃｉｎｉｄｏｎ－ｅｔｈｙｌ）、カルフェントラゾンエチル（Ｃａｒｆｅｎｔｒａｚｏｎｅ－ｅｔｈｙｌ）、スルフェントラゾン（Ｓｕｒｆｅｎｔｒａｚｏｎｅ）、フルミクロラックペンチル（Ｆｌｕｍｉｃｌｏｒａｃ－ｐｅｎｔｙｌ）、フルミオキサジン（Ｆｌｕｍｉｏｘａｚｉｎ）、ピラフルフェンエチル（Ｐｙｒａｆｌｕｆｅｎ－ｅｔｈｙｌ）、オキサジアルギル（Ｏｘａｄｉａｒｇｙ１）、ペントキサゾン（Ｐｅｎｔｏｘａｚｏｎｅ）、フルチアセットメチル（Ｆｌｕｔｈｉａｃｅｔ－ｍｅｔｈｙｌ）、ブタフェナシル（Ｂｕｔａｆｅｎａｃｉｌ）、ベンズフェンジゾン（Ｂｅｎｚｆｅｎｄｉｚｏｎｅ）、ベンカルバゾン（Ｂｅｎｃａｒｂａｚｏｎｅ）、及びサフルフェナシル（Ｓａｆｌｕｆｅｎａｃｉｌ）。
（１４）ピラゾール除草性化合物
　ベンゾフェナップ（Ｂｅｎｚｏｆｅｎａｐ）、ピラゾレート（Ｐｙｒａｚｏ１ａｔｅ）、ピラゾキシフェン（Ｐｙｒａｚｏｘｙｆｅｎ）、トプラメゾン（Ｔｏｐｒａｍｅｚｏｎｅ）、及びピラスルホトール（Ｐｙｒａｓｕｌｆｏｔｏｌｅ）。
（１５）トリケトン除草性化合物
　イソキサフルトール（Ｉｓｏｘａｆｌｕｔｏｌｅ）、ベンゾビシクロン（Ｂｅｎｚｏｂｉｃｙｃｌｏｎ）、スルコトリオン（Ｓｕｌｃｏｔｒｉｏｎｅ）、メソトリオン（Ｍｅｓｏｔｒｉｏｎｅ）、テンボトリオン（Ｔｅｍｂｏｔｒｉｏｎｅ）、及びテフリルトリオン（Ｔｅｆｕｒｙｌｔｒｉｏｎｅ）。
（１６）アリールオキシフェノキシプロピオン酸除草性化合物
　クロジナホッププロパルギル（Ｃｌｏｄｉｎａｆｏｐ－ｐｒｏｐａｒｇｙｌ）、シハロホップブチル（Ｃｙｈａｌｏｆｏｐ－ｂｕｔｙｌ）、ジクロホップメチル（Ｄｉｃｌｏｆｏｐ－ｍｅｔｈｙｌ）、フェノキサプロップエチル（Ｆｅｎｏｘａｐｒｏｐ－ｅｔｈｙｌ）、フルアジホップブチル（Ｆｌｕａｚｉｆｏｐ－ｂｕｔｙｌ）、ハロキシホップメチル（Ｈａｌｏｘｙｆｏｐ－ｍｅｔｈｙｌ）、キザロホップエチル（Ｑｕｉｚａｌｏｆｏｐ－ｅｔｈｙｌ）、及びメタミホップ（Ｍｅｔａｍｉｆｏｐ）。
（１７）トリオンオキシム除草性化合物
　アロキシジム（Ａｌｌｏｘｙｄｉｍ－ｓｏｄｉｕｍ）、セトキシジム（Ｓｅｔｈｏｘｙｄｉｍ）、ブトロキシジム（Ｂｕｔｒｏｘｙｄｉｍ）、クレソジム（Ｃｌｅｔｈｏｄｉｍ）、クロプロキシジム（Ｃｌｏｐｒｏｘｙｄｉｍ）、シクロキシジム（Ｃｙｃｌｏｘｙｄｉｍ）、テプラロキシジム（Ｔｅｐｒａｌｏｘｙｄｉｍ）、トラルコキシジム（Ｔｒａｌｋｏｘｙｄｉｍ）、及びプロフォキシジム（Ｐｒｏｆｏｘｙｄｉｍ）。
（１８）スルホニル尿素除草性化合物
　クロルスルフロン（Ｃｈｌｏｒｓｕｌｆｕｒｏｎ）、スルホメツロンメチル（Ｓｕｌｆｏｍｅｔｕｒｏｎ－ｍｅｔｈｙｌ）、メトスルフロンメチル（Ｍｅｔｓｕ１ｆｕｒｏｎ－ｍｅｔｈｙ１）、クロリムロンエチル（Ｃｈｌｏｒｉｍｕｒｏｎ－ｅｔｈｙｌ）、トリベニュロンメチル（Ｔｒｉｂｅｎｕｒｏｎ－ｍｅｔｈｙｌ）、トリアスルフロン（Ｔｒｉａｓｕｌｆｕｒｏｎ）、ベンスルフロンメチル（Ｂｅｎｓｕｌｆｕｒｏｎ－ｍｅｔｈｙ１）、チフェンスルフロンメチル（Ｔｈｉｆｅｎｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、ピラゾスルフロンエチル（Ｐｙｒａｚｏｓｕｌｆｕｒｏｎ－ｅｔｈｙ１）、プリミスルフロンメチル（Ｐｒｉｍｉｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、ニコスルフロン（Ｎｉｃｏｓｕｌｆｕｒｏｎ）、アミドスルフロン（Ａｍｉｄｏｓｕｌｆｕｒｏｎ）、シノスルフロン（Ｃｉｎｏｓｕｌｆｕｒｏｎ）、イマゾスルフロン（Ｉｍａｚｏｓｕｌｆｕｒｏｎ）、リムスルフロン（Ｒｉｍｓｕｌｆｕｒｏｎ）、ハロスルフロンメチル（Ｈａ１ｏｓｕｌｆｕｒｏｎ－ｍｅｔｈｙ１）、プロスルフロン（Ｐｒｏｓｕｌｆｕｒｏｎ）、エタメトスルフロンメチル（Ｅｔｈａｍｅｔｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、トリフルスルフロンメチル（Ｔｒｉｆｌｕｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、フラザスルフロン（Ｆｌａｚａｓｕｌｆｕｒｏｎ）、シクロスルファムロン（Ｃｙｃ１ｏｓｕｌｆａｍｕｒｏｎ）、フルピルスルフロン（Ｆｌｕｐｙｒｓｕｌｆｕｒｏｎ）、スルホスルフロン（Ｓｕｌｆｏｓｕ１ｆｕｒｏｎ）、アジムスルフロン（Ａｚｉｍｓｕｌｆｕｒｏｎ）、エトキシスルフロン（Ｅｔｈｏｘｙｓｕｌｆｕｒｏｎ）、オキサスルフロン（Ｏｘａｓｕｌｆｕｒｏｎ）、ヨードスルフロンメチルナトリウム（Ｉｏｄｏｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ－ｓｏｄｉｕｍ）、フォラムスルフロン（Ｆｏｒａｍｓｕｌｆｕｒｏｎ）、メソスルフロンメチル（Ｍｅｓｏｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、トリフロキシスルフロン（Ｔｒｉｆｌｏｘｙｓｕｌｆｕｒｏｎ）、トリトスルフロン（Ｔｒｉｔｏｓｕｌｆｕｒｏｎ）、オルソスルファムロン（ｏｒｔｈｏｓｕｌｆａｍｕｒｏｎ），フルセトスルフロン（Ｆｌｕｃｅｔｏｓｕｌｆｕｒｏｎ）、及びプロピリスルフロン（Ｐｒｏｐｙｒｉｓｕｌｆｕｒｏｎ）。
（１９）イミダゾリノン除草性化合物
　イマザメタベンズメチル（Ｉｍａｚａｍｅｔｈａｂｅｎｚ－ｍｅｔｈｙｌ）、イマザメタピル（Ｉｍａｚａｍｅｔｈａｐｙｒ）、イマザモックス（Ｉｍａｚａｍｏｘ）、イマザピル（Ｉｍａｚａｐｙｒ）、イマザキン（Ｉｍａｚａｑｕｉｎ）、イマゼタピル（Ｉｍａｚｅｔｈａｐｙｒ）等。
（２０）スルホンアミド除草性化合物
　フルメトスラム（Ｆｌｕｍｅｔｓｕｌａｍ）、メトスラム（Ｍｅｔｏｓｕｌａｍ）、ジクロスラム（Ｄｉｃｌｏｓｕｌａｍ）、フロラスラム（Ｆｌｏｒａｓｕｌａｍ）、クロランスラムメチル（Ｃｌｏｒａｎｓｕｌａｍ－ｍｅｔｈｙｌ）、ペノキススラム（Ｐｅｎｏｘｓｕｌａｍ）、及びピロキススラム（Ｐｙｒｏｘｓｕｌａｍ）。
（２１）ピリミジニルオキシ安息香酸除草性化合物
　ピリチオバックナトリウム（Ｐｙｒｉｔｈｉｏｂａｃ－ｓｏｄｉｕｍ）、ビスピリバックナトリウム（Ｂｉｓｐｙｒｉｂａｃ－ｓｏｄｉｕｍ）、ピリミノバックメチル（Ｐｙｒｉｍｉｎｏｂａｃ－ｍｅｔｈｙ１）、ピリベンゾキシム（Ｐｙｒｉｂｅｎｚｏｘｉｍ）、ピリフタリド（Ｐｙｒｉｆｔａｌｉｄ）、及びピリミスルファン（Ｐｙｒｉｍｉｓｕｌｆａｎ）。
（２２）その他の除草性化合物
　ベンタゾン（Ｂｅｎｔａｚｏｎ）、ブロマシル（Ｂｒｏｍａｃｉｌ）、ターバシル（Ｔｅｒｂａｃｉｌ）、クロルチアミド（Ｃｈｌｏｒｔｈｉａｍｉｄ）、イソキサベン（Ｉｓｏｘａｂｅｎ）、ジノセブ（Ｄｉｎｏｓｅｂ）、アミトロール（Ａｍｉｔｒｏｌｅ）、シンメチリン（Ｃｉｎｍｅｔｈｙｌｉｎ）、トリジファン（Ｔｒｉｄｉｐｈａｎｅ）、ダラポン（Ｄａ１ａｐｏｎ）、ジフルフェンゾピルナトリウム（Ｄｉｆｌｕｆｅｎｚｏｐｙｒ
－ｓｏｄｉｕｍ）、ジチオピル（Ｄｉｔｈｉｏｐｙｒ）、チアゾピル（Ｔｈｉａｚｏｐｙｒ）、フルカルバゾンナトリウム（Ｆｌｕｃａｒｂａｚｏｎｅ－ｓｏｄｉｕｍ）、プロポキシカルバゾンナトリウム（Ｐｒｏｐｏｘｙｃａｒｂａｚｏｎｅ－ｓｏｄｉｕｍ）、メフェナセット（Ｍｅｆｅｎａｃｅｔ）、フルフェナセット（Ｆｌｕｆｅｎａｃｅｔ）、フェントラザミド（Ｆｅｎｔｒａｚａｍｉｄｅ）、カフェンストロール（Ｃａｆｅｎｓｔｒｏｌｅ）、インダノファン（Ｉｎｄａｎｏｆａｎ）、オキサジクロメホン（Ｏｘａｚｉｃｌｏｍｅｆｏｎｅ）、ベンフレセート（Ｂｅｎｆｕｒｅｓａｔｅ）、ＡＣＮ、ピリデート（Ｐｙｒｉｄａｔｅ）、クロリダゾン（Ｃｈｌｏｒｉｄａｚｏｎ）、ノルフルラゾン（Ｎｏｒｆｌｕｒａｚｏｎ）、フルルタモン（Ｆｌｕｒｔａｍｏｎｅ）、ジフルフェニカン（Ｄｉｆｌｕｆｅｎｉｃａｎ）、ピコリナフェン（Ｐｉｃｏｌｉｎａｆｅｎ）、ベフルブタミド（Ｂｅｆｌｕｂｕｔａｍｉｄ）、クロマゾン（Ｃｌｏｍａｚｏｎｅ）、アミカルバゾン（Ａｍｉｃａｒｂａｚｏｎｅ）、ピノキサデン（Ｐｉｎｏｘａｄｅｎ）、ピラクロニル（Ｐｙｒａｃｌｏｎｉｌ）、ピロキサスルホン（Ｐｙｒｏｘａｓｕｌｆｏｎｅ）、チエンカルバゾンメチル（Ｔｈｉｅｎｃａｒｂａｚｏｎｅ－ｍｅｔｈｙｌ）、アミノシクロピラクロール（Ａｍｉｎｏｃｙｃｌｏｐｙｒａｃｈｌｏｒ）、イプフェンカルバゾン（Ｉｐｆｅｎｃａｒｂａｚｏｎｅ）、及びメチオゾリン（Ｍｅｔｈｉｏｚｏｌｉｎ）。
共力剤の有効成分
　ピペロニル　ブトキサイド（Ｐｉｐｅｒｏｎｙｌ　ｂｕｔｏｘｉｄｅ）、　セサメックス（Ｓｅｓａｍｅｘ）、スルホキシド（Ｓｕｌｆｏｘｉｄｅ）、Ｎ－（２－エチルへキシル）－８，９，１０－トリノルボルン－５－エン－２，３－ジカルボキシイミド（ＭＧＫ　２６４）、Ｎ－デクリイミダゾール（Ｎ－Ｄｅｃｌｙｉｍｉｄａｚｏｌｅ）、ＷＡＲＦ－アンチレジスタント（ＷＡＲＦ－ａｎｔｉｒｅｓｉｓｔａｎｔ）、ＴＢＰＴ、ＴＰＰ、ＩＢＰ、ＰＳＣＰ、ヨウ化メチル（ＣＨ3Ｉ）、ｔ－フェニルブテノン（ｔ－Ｐｈｅｎｙｌｂｕｔｅｎｏｎｅ）、ジエチルマレエート（Ｄｉｅｔｈｙｌｍａｌｅａｔｅ）、ＤＭＣ、ＦＤＭＣ、ＥＴＰ、及びＥＴＮ。
　上記の混用または併用できる有効成分のうち、特に好ましい例として、カルタップ塩酸塩、フィプロニル、メトキシフェノジド、テブフェノジド、クロチアニジン、スピノサド、スピネトラム、クロラントラニリプロール、シアントラニリプロールなどの殺虫剤の有効成分、ジクロシメット、フサライド、トリシクラゾール、ピロキロン、アゾキシストロビン、メトミノストロビン、オリサストロビン、フルトラニル、フラメトピル、チフルザミド、プロベナゾール、チアジニル、イソチアニル、バリダマイシン，カスガマイシン、フェリムゾンなどの殺菌剤の有効成分が挙げられる。 Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (Phenothio1), mecoprop (Fluoxypyr), triclopyr (Triclopyr), Clomeprop, Clomeprop Naproanilide.
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds diuron (Diuron), linuron (Linuron), chlortoluron (Chlortururon), isoproturon (Isoproturon), fluometuron (Isouron) (Isouron), Tebutiuron (Tebuthuron (Tebuthuron) , Cumyluron, Daimuron, and Methyl-daimuron.
(4) Triazine herbicidal compounds Atrazine, Ametrine, Cyanazine, Simazine, Propazine, Simetrin, Dimetamethrin, Dimethamethrin ), Triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compound Paraquat and Diquat.
(6) Hydroxybenzonitrile herbicidal compound Bromoxynil and Ioxynil.
(7) Dinitroaniline herbicidal compound Pendimethalin, Prodiamine, and Trifluralin.
(8) Organophosphorus herbicidal compounds Amiprofos-methyl, Butamifos, Bensulide, Piperophos, Anilofos, Glyphosate, Glufonate, Glufonate P (Glufosinate-P), and Bialaphos.
(9) Carbamate herbicidal compound: Di-allate, Tri-alate, EPTC, Butyrate, Benchiocarb, Esprocarb, Molinate, Dimepiperate, Dimepiperate (Swep), Chlorprofham, Phenmedifam, Phenisopham, Pyributicalb, and Asuram.
(10) Acid amide herbicidal compound Propanil, Propyzamide, Bromobutide, and Etobenzanide.
(11) Chloroacetanilide herbicidal compounds Acetochlor, Alaclor, Butachlor, Dimethenamide, Propaclor, Metazachlor, Metolachlor, Metolachlor Pretilachor), tenylchlor (Theny1ch1or), and petoxamide (Pethoxamide).
(12) Diphenyl ether herbicidal compound acifluorfen (Acifluorfen-sodium), bifenox (Oxyfluorfen), lactofen (Lactofen), fomesafen (Chlophenoxy), clomethoxypheny (Chlophenoxy)
(13) Cyclic imide herbicidal compounds Oxadiazone, Cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumilacrac-pentyl Oxazine (Flumioxazin), Pyraflufen-ethyl, Oxadiargyl (Oxadialy), Pentoxazone, Fluthiacet-methyl, Butafenzene (Butafenzil) azone), and saflufenacil.
(14) Pyrazole herbicidal compounds: Benzofenap, Pyrazolate, Pyrazoxifene, Topramzone, and Pyrasulfotole.
(15) Triketone herbicidal compounds Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefril trione.
(16) Aryloxyphenoxypropionic acid herbicidal compound Clodinafop-propargyl, Cyhalofop-butyl, Diclohop-methyl, Fenoxaprop-ethyl Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, and metamihop.
(17) Trione oxime herbicidal compounds Alloxydim-sodium, cetoxydim, Butroxidim, Crethodim, Cloproxidim, Cyclodimoxime (Tralkoxydim), and Profoxydim.
(18) Sulphonylurea herbicidal compound Chlorsulfuron, Sulfomethuron-methyl, Metsulfuron-methyl, Chlorimuron-ethyl, Tribenuron methyl Tribenuron-methyl), trisulfuron (Triasulfuron), bensulfuron-methyl (Bensulfuron-methy1), thifensulfuron-methyl (Pyrazsulfuron-methyl), pyrysulfururon-methyl- (1) Nicosulfuron (Nico sulfuron, amidosulfuron, minosulfuron, imosulfuron, rimsulfuron, halosulfuronmethyl (Halsulfuron-sulfuron) , Triflusulfuron-methyl, frazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azulfurium Azulsulfuron, ethoxysulfuron, oxasulfuron, sodium iodosulfuron methyl sodium (Idosulfuron-methyl-sodium), foramsulfuron, mesosulfuron methyl Trisulfursulfuron, Tritosulfuron, Orthosulfururon, Flucetosulfuron, and Propyrisulfuron.
(19) Imidazolinone herbicidal compounds Imazametabenzmethyl (Imazamethapyr), imazamoxyl, imazapyr (i), imazapir (in), imazakin (in)
(20) Sulfonamide herbicidal compounds Flumeslam, Methoslam, Diclosram, Floraslam, chloranthramx, Penoxsulox and Penoxsulox.
(21) Pyrimidinyloxybenzoic acid herbicidal compound Pyrithiobac-sodium, Bispyribac-sodium, Pyriminobac-methyl1, Pyribenzoximf, Pyribenzoximf And Pyrimisulfan.
(22) Other herbicidal compounds: Bentazone, Bromasil, Terbacil, Chlorthiamid, Isoxaben, Dinoseb, Amitrol, Methiline, C Tridiphane, Dalapon (Dalapon), Diflufenzopyr sodium (Diflufenzopyr)
-Sodium), dithiopyr, thiazopyr, flucarbazone sodium (Flucarbazone-sodium), propoxycarbazone sodium (propoxycarbazone-sodium), mefenacet flufenet , Caffentrol, Indanofan, Oxadiclomephone, Benfrateate, ACN, Pyridate, Chloridazon, Norflurazon, Norflurazon Tumon (Flutamone), Diflufenican, Picolinafene (Picolinafene), Beflubutamid (Clozone), Amicalazone (Pinroxenil), Pinoxaden (Pinoxaden) Methyl (Thiencarbazone-methyl), Aminocyclopyrachlor, Ipfencarbazone, and Methiozoline.
Active ingredient of synergist Piperonyl butoxide, Sesamex, Sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-di Carboximide (MGK 264), N-decrimimidazole (N-Declinimidazole), WARF-anti-resistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH 3 I), t-phenyl butyl Tenon (t-Phenylbutenone), Diethylmaleate, DMC, FDMC, ETP, and ETN.
Among the active ingredients that can be used in combination or in combination, particularly preferred examples include active ingredients of insecticides such as cartap hydrochloride, fipronil, methoxyphenozide, tebufenozide, clothianidin, spinosad, spinetoram, chlorantraniliprole, cyantraniliprole Examples include active ingredients of fungicides such as diclocimet, fusaride, tricyclazole, pyroxylone, azoxystrobin, metminostrobin, orisatrobin, flutolanil, furamethpyr, tifluzamide, probenazole, thiazinyl, isothianyl, validamycin, kasugamycin, and ferrimzone.
　以下、製造例、製剤例、試験例等により本発明をさらに詳しく説明するが、本発明はこれらの例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.
　まず、本発明化合物の製造例を以下に示す。 First, production examples of the compound of the present invention are shown below.
　製造例１
　４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）ピリジン（化合物２－１）の製造 Production Example 1
Production of 4- (5-tert-butylthiophen-2-ylmethyl) pyridine (Compound 2-1)
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000046
　２－ブロモ－５－ｔｅｒｔ－ブチルチオフェン１．００ｇとテトラヒドロフラン５０ｍｌとの混合物に、－７８℃で、ｎ－ブチルリチウム（１．６Ｍのヘキサン溶液）３．１３ｍｌを滴下し、－７８℃で１時間攪拌した。次に、－７８℃で、イソニコチンアルデヒド０．５２ｍｌを滴下した。－７８℃で１０分間攪拌した後、０℃まで昇温し、飽和炭酸水素ナトリウムを注加した。反応混合物を酢酸エチルで抽出し、有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、（５－ｔｅｒｔ－ブチルチオフェン－２－イル）（ピリジン－４－イル）メタノール０．７１ｇを得た。
1H-NMR (CDCl3) δ: 1.34 (9H, s), 5.97 (1H, s), 6.66 (1H, d), 6.73-6.74 (1H, m), 7.38-7.39 (2H, m), 8.58 (2H, dd).
　（５－ｔｅｒｔ－ブチルチオフェン－２－イル）（ピリジン－４－イル）メタノール０．７１ｇ、硫酸０．３ｍｌ、酢酸９．０ｍｌおよびＰｄ炭素（触媒量）を混合し、約１気圧の水素雰囲気下、室温で２．５時間攪拌した。反応混合物を濾過した後、濾液に水酸化ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）ピリジン０．３２ｇを得た。
1H-NMR (CDCl3) δ: 1.34 (9H, s), 4.07 (2H, s), 6.60 (1H, d), 6.64 (1H, d), 7.18 (2H, dd), 8.52 (2H, dd).
　製造例２
　４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－フルオロピリジン（化合物２－２）の製造 To a mixture of 1.00 g of 2-bromo-5-tert-butylthiophene and 50 ml of tetrahydrofuran, 3.13 ml of n-butyllithium (1.6M hexane solution) was added dropwise at −78 ° C., and 1 at −78 ° C. Stir for hours. Next, at -78 ° C., 0.52 ml of isonicotinaldehyde was added dropwise. After stirring at −78 ° C. for 10 minutes, the temperature was raised to 0 ° C., and saturated sodium bicarbonate was added. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.71 g of (5-tert-butylthiophen-2-yl) (pyridin-4-yl) methanol.
1 H-NMR (CDCl 3 ) δ: 1.34 (9H, s), 5.97 (1H, s), 6.66 (1H, d), 6.73-6.74 (1H, m), 7.38-7.39 (2H, m), 8.58 (2H, dd).
(5-tert-Butylthiophen-2-yl) (pyridin-4-yl) methanol 0.71 g, sulfuric acid 0.3 ml, acetic acid 9.0 ml and Pd carbon (catalytic amount) were mixed, and hydrogen atmosphere at about 1 atm. The mixture was stirred at room temperature for 2.5 hours. After filtering the reaction mixture, an aqueous sodium hydroxide solution was poured into the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.32 g of 4- (5-tert-butylthiophen-2-ylmethyl) pyridine.
1 H-NMR (CDCl 3 ) δ: 1.34 (9H, s), 4.07 (2H, s), 6.60 (1H, d), 6.64 (1H, d), 7.18 (2H, dd), 8.52 (2H, dd ).
Production Example 2
Preparation of 4- (5-tert-butylthiophen-2-ylmethyl) -3-fluoropyridine (Compound 2-2)
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000047
　２－ブロモ－５－ｔｅｒｔ－ブチルチオフェン１．９５ｇとテトラヒドロフラン７０ｍｌとの混合物に、－７８℃で、ｎ－ブチルリチウム（１．６Ｍのヘキサン溶液）６．１２ｍｌを滴下し、－７８℃で１時間攪拌した。次に、－７８℃で、３－フルオロイソニコチンアルデヒド０．９８ｍｌを滴下した。－７８℃で１０分間攪拌した後、０℃まで昇温し、飽和炭酸水素ナトリウムを注加した。反応混合物を酢酸エチルで抽出し、有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、（５－ｔｅｒｔ－ブチルチオフェン－２－イル）（３－フルオロピリジン－４－イル）メタノール２．０６ｇを得た。
1H-NMR (CDCl3) δ: 1.34 (9H, s), 6.28 (1H, s), 6.66 (1H, d), 6.76 (1H, d), 7.65 (1H, t), 8.40 (1H, s), 8.46 (1H, d).
　（５－ｔｅｒｔ－ブチルチオフェン－２－イル）（３－フルオロピリジン－４－イル）メタノール０．７８ｇ、硫酸１．０ｍｌ、酢酸２０ｍｌおよびＰｄ炭素（触媒量）を混合し、約１気圧の水素雰囲気下、室温で３時間攪拌した。反応混合物を濾過した後、濾液に水酸化ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－フルオロピリジン０．６６ｇを得た。
1H-NMR (CDCl3) δ: 1.35 (9H, s), 4.13 (2H, s), 6.64 (2H, s), 7.17 (1H, t), 8.33 (1H, d), 8.41 (1H, d).
　製造例３
　４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－メトキシピリジン（化合物２－７）の製造 To a mixture of 1.95 g of 2-bromo-5-tert-butylthiophene and 70 ml of tetrahydrofuran, 6.12 ml of n-butyllithium (1.6M hexane solution) was added dropwise at -78 ° C., and 1 at −78 ° C. Stir for hours. Next, 0.98 ml of 3-fluoroisonicotinaldehyde was added dropwise at −78 ° C. After stirring at −78 ° C. for 10 minutes, the temperature was raised to 0 ° C., and saturated sodium bicarbonate was added. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 2.06 g of (5-tert-butylthiophen-2-yl) (3-fluoropyridin-4-yl) methanol.
1 H-NMR (CDCl 3 ) δ: 1.34 (9H, s), 6.28 (1H, s), 6.66 (1H, d), 6.76 (1H, d), 7.65 (1H, t), 8.40 (1H, s ), 8.46 (1H, d).
(5-tert-Butylthiophen-2-yl) (3-fluoropyridin-4-yl) methanol (0.78 g), sulfuric acid (1.0 ml), acetic acid (20 ml) and Pd carbon (catalytic amount) were mixed, and about 1 atm of hydrogen was mixed. Stir for 3 hours at room temperature under atmosphere. After filtering the reaction mixture, an aqueous sodium hydroxide solution was poured into the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.66 g of 4- (5-tert-butylthiophen-2-ylmethyl) -3-fluoropyridine.
1 H-NMR (CDCl 3 ) δ: 1.35 (9H, s), 4.13 (2H, s), 6.64 (2H, s), 7.17 (1H, t), 8.33 (1H, d), 8.41 (1H, d ).
Production Example 3
Production of 4- (5-tert-butylthiophen-2-ylmethyl) -3-methoxypyridine (Compound 2-7)
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000048
　４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－フルオロピリジン０．２１ｇ、ナトリウムメトキシド（２８％のメタノール溶液）１．６３ｇ、およびＮ，Ｎ－ジメチルホルムアミド２．０ｍｌの混合物を、１２０℃で、３時間攪拌した。反応混合物に水を注加した後、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－メトキシピリジン０．１４ｇを得た。
1H-NMR (CDCl3) δ: 1.34 (9H, s), 3.95 (3H, s), 4.07 (2H, s), 6.60 (1H, d), 6.63 (1H, d), 7.07 (1H, d), 8.17 (1H, d), 8.23 (1H, s).
　製造例４
４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－（メチルチオ）ピリジン（化合物２－１０）の製造 A mixture of 0.21 g 4- (5-tert-butylthiophen-2-ylmethyl) -3-fluoropyridine, 1.63 g sodium methoxide (28% methanol solution), and 2.0 ml N, N-dimethylformamide. The mixture was stirred at 120 ° C. for 3 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.14 g of 4- (5-tert-butylthiophen-2-ylmethyl) -3-methoxypyridine.
1 H-NMR (CDCl 3 ) δ: 1.34 (9H, s), 3.95 (3H, s), 4.07 (2H, s), 6.60 (1H, d), 6.63 (1H, d), 7.07 (1H, d ), 8.17 (1H, d), 8.23 (1H, s).
Production Example 4
Preparation of 4- (5-tert-butylthiophen-2-ylmethyl) -3- (methylthio) pyridine (Compound 2-10)
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000049
　４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－フルオロピリジン０．２１ｇ、ナトリウムチオメトキシド０．１２ｇ、およびＮ，Ｎ－ジメチルホルムアミド２．０ｍｌの混合物を、室温で３時間攪拌した。反応混合物に水を注加した後、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４－（５－ｔｅｒｔ－ブチルチオフェン－２－イルメチル）－３－（メチルチオ）ピリジン０．１３ｇを得た。
1H-NMR (CDCl3) δ: 1.34 (9H, s), 2.52 (3H, s), 4.16 (2H, s), 6.61 (1H, d), 6.64 (1H, d), 7.08 (1H, d), 8.34 (1H, d), 8.46 (1H, s).
　製造例５
４－（１－ｔｅｒｔ－ブチルピラゾール－４－イルメチル）ピリジン（化合物３－３５）の製造 A mixture of 0.21 g of 4- (5-tert-butylthiophen-2-ylmethyl) -3-fluoropyridine, 0.12 g of sodium thiomethoxide and 2.0 ml of N, N-dimethylformamide was stirred at room temperature for 3 hours. did. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.13 g of 4- (5-tert-butylthiophen-2-ylmethyl) -3- (methylthio) pyridine.
1 H-NMR (CDCl 3 ) δ: 1.34 (9H, s), 2.52 (3H, s), 4.16 (2H, s), 6.61 (1H, d), 6.64 (1H, d), 7.08 (1H, d ), 8.34 (1H, d), 8.46 (1H, s).
Production Example 5
Preparation of 4- (1-tert-butylpyrazol-4-ylmethyl) pyridine (Compound 3-35)
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000050
　４－ブロモ－１－ｔｅｒｔ－ブチルピラゾール０．４０ｇとジエチルエーテル２０ｍｌとの混合物に、－７０℃で、ｎ－ブチルリチウム（１．６Ｍのヘキサン溶液）１．４８ｍｌを滴下した。次に、－７０℃で、イソニコチンアルデヒド０．２５ｇを滴下した。－７０℃で４５分間攪拌した後、室温まで昇温し、水を反応液に注加した。反応混合物を酢酸エチルで抽出し、有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、（１－ｔｅｒｔ－ブチルピラゾール－４－イル）（ピリジン－４－イル）メタノール８３ｍｇを得た。
1H-NMR (CDCl3) δ: 1.55 (9H, s), 5.83 (1H, s), 7.33-7.43 (3H, m), 7.43 (1H, s), 8.55 (2H, dd).
　（１－ｔｅｒｔ－ブチルピラゾール－４－イル）（ピリジン－４－イル）メタノール８２ｍｇ、硫酸０．５ｍｌ、酢酸７．０ｍｌおよびＰｄ炭素（触媒量）を混合し、約１気圧の水素雰囲気下、室温で２時間攪拌した。反応混合物を濾過した後、濾液ろ液に水酸化ナトリウム水溶液を注加し、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮し、４－（１－ｔｅｒｔ－ブチルピラゾール－４－イルメチル）ピリジン７５ｍｇを得た。
1H-NMR (CDCl3) δ: 1.57 (9H, s), 3.82 (2H, s), 7.13 (2H, dd), 7.28 (1H, s), 7.37(1H, s), 8.50 (2H, dd).
　製造例６
　４－（３－ｔｅｒｔ－ブチルピラゾール－１－イルメチル）ピリジン（化合物５－１）の製造 To a mixture of 0.40 g of 4-bromo-1-tert-butylpyrazole and 20 ml of diethyl ether, 1.48 ml of n-butyllithium (1.6 M hexane solution) was added dropwise at -70 ° C. Next, at −70 ° C., 0.25 g of isonicotinaldehyde was added dropwise. After stirring at −70 ° C. for 45 minutes, the temperature was raised to room temperature, and water was poured into the reaction solution. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 83 mg of (1-tert-butylpyrazol-4-yl) (pyridin-4-yl) methanol.
1 H-NMR (CDCl 3 ) δ: 1.55 (9H, s), 5.83 (1H, s), 7.33-7.43 (3H, m), 7.43 (1H, s), 8.55 (2H, dd).
82 mg of (1-tert-butylpyrazol-4-yl) (pyridin-4-yl) methanol, 0.5 ml of sulfuric acid, 7.0 ml of acetic acid and Pd carbon (catalytic amount) were mixed, and under a hydrogen atmosphere of about 1 atm. Stir at room temperature for 2 hours. After filtering the reaction mixture, an aqueous sodium hydroxide solution was poured into the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 75 mg of 4- (1-tert-butylpyrazol-4-ylmethyl) pyridine.
1 H-NMR (CDCl 3 ) δ: 1.57 (9H, s), 3.82 (2H, s), 7.13 (2H, dd), 7.28 (1H, s), 7.37 (1H, s), 8.50 (2H, dd ).
Production Example 6
Production of 4- (3-tert-butylpyrazol-1-ylmethyl) pyridine (Compound 5-1)
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
　水素化ナトリウム０．３２ｇとＮ，Ｎ－ジメチルホルムアミド１．５ｍｌの混合物に３－ｔｅｒｔ－ブチルピラゾール０．４０ｇとＮ，Ｎ－ジメチルホルムアミド３．５ｍｌの混合物を０℃で滴下し、室温で５分間攪拌した。次に４－クロロメチルピリジン塩酸塩０．５３ｇを０℃で加え、５０℃で４０分間攪拌した。放冷した反応混合物に水を注加した後、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４－（３－ｔｅｒｔ－ブチルピラゾール－１－イルメチル）ピリジン０．５６ｇを得た。
1H-NMR (CDCl3) δ: 1.33 (9H, s), 5.30 (2H, s), 6.18 (1H, d), 6.97 (2H, d), 7.29 (1H, d), 8.55 (2H, d).
　製造例７
　４－［３－（２，２－ジメチルプロピル）－１，２，４－トリアゾール－１－イルメチル］ピリジン（化合物６－１８）の製造 To a mixture of 0.32 g of sodium hydride and 1.5 ml of N, N-dimethylformamide, a mixture of 0.40 g of 3-tert-butylpyrazole and 3.5 ml of N, N-dimethylformamide was added dropwise at 0 ° C., and 5 ml at room temperature. Stir for minutes. Next, 0.53 g of 4-chloromethylpyridine hydrochloride was added at 0 ° C., and the mixture was stirred at 50 ° C. for 40 minutes. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.56 g of 4- (3-tert-butylpyrazol-1-ylmethyl) pyridine.
1 H-NMR (CDCl 3 ) δ: 1.33 (9H, s), 5.30 (2H, s), 6.18 (1H, d), 6.97 (2H, d), 7.29 (1H, d), 8.55 (2H, d ).
Production Example 7
Production of 4- [3- (2,2-dimethylpropyl) -1,2,4-triazol-1-ylmethyl] pyridine (Compound 6-18)
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000052
　水素化ナトリウム０．２２ｇとＮ，Ｎ－ジメチルホルムアミド４．０ｍｌの混合物に３－（２，２－ジメチルプロピル）－１Ｈ－１，２，４－トリアゾール０．３０ｇを０℃で加え、室温で５分間攪拌した。次に４－クロロメチルピリジン塩酸塩０．３５ｇを０℃で加え、５０℃で１０分間攪拌した。放冷した反応混合物に水を注加した後、酢酸エチルで抽出した。有機層を水洗した後、無水硫酸マグネシウムで乾燥し、減圧下に濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、４－［３－（２，２－ジメチルプロピル）－１，２，４－トリアゾール－１－イルメチル］ピリジン０．２９ｇを得た。
1H-NMR (CDCl3) δ: 1.00 (9H, s), 2.65 (2H, s), 5.33 (2H, s), 7.07 (2H, dd), 8.05(1H, s), 8.60 (2H, dd).
　以下、前述の実施製造例に記載の方法に準じた製造方法により製造される化合物を例示する。 To a mixture of 0.22 g of sodium hydride and 4.0 ml of N, N-dimethylformamide was added 0.30 g of 3- (2,2-dimethylpropyl) -1H-1,2,4-triazole at 0 ° C., and at room temperature. Stir for 5 minutes. Next, 0.35 g of 4-chloromethylpyridine hydrochloride was added at 0 ° C., and the mixture was stirred at 50 ° C. for 10 minutes. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 0.29 g of 4- [3- (2,2-dimethylpropyl) -1,2,4-triazol-1-ylmethyl] pyridine.
1 H-NMR (CDCl 3 ) δ: 1.00 (9H, s), 2.65 (2H, s), 5.33 (2H, s), 7.07 (2H, dd), 8.05 (1H, s), 8.60 (2H, dd ).
Hereinafter, the compound manufactured by the manufacturing method according to the method as described in the above-mentioned Example manufacture example is illustrated.
　表中、Ｍｅはメチル基（ＣＨ3－）、Ｅｔはエチル基（ＣＨ3ＣＨ2－）、Ｐｒはプロピル基（ＣＨ3ＣＨ2ＣＨ2－）、ｉ－Ｐｒはイソプロピル基（（ＣＨ3）2ＣＨ－）、ｔ－Ｂｕはｔｅｒｔ－ブチル基（（ＣＨ3）3Ｃ－）を表し、ｓｅｃ－Ｂｕはｓｅｃ－ブチル基（ＣＨ3ＣＨ2ＣＨ（ＣＨ3）－）を表す。 In the table, Me is a methyl group (CH 3 —), Et is an ethyl group (CH 3 CH 2 —), Pr is a propyl group (CH 3 CH 2 CH 2 —), and i-Pr is an isopropyl group ((CH 3 )). 2 CH—) and t-Bu represent a tert-butyl group ((CH 3 ) 3 C—), and sec-Bu represents a sec-butyl group (CH 3 CH 2 CH (CH 3 ) —).
　表中、「（Ｅ１）n」の列において、ｎが１である場合は、例えば「３－Ｍｅ」のように示し、これは、Ｅ１がＨｅｔで表されるヘテロ芳香環の３位に置換したメチル基であることを意味し、ｎが０である場合は、「－」のように示し、無置換であることを意味する。 In the table, in the column “(E 1 ) n ”, when n is 1, for example, “3-Me” is indicated, which is the 3-position of the heteroaromatic ring in which E 1 is represented by Het. It means that it is a substituted methyl group, and when n is 0, it is shown as “-”, which means that it is unsubstituted.
　式（Ａ－１）で表される化合物。 Compound represented by formula (A-1).
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
　式中のＪ－Ｌ－Ａ基、（Ｅ１）n、Ｑ、Ｄ、Ｇ及びｍは、下記の〔表７〕～〔表１０〕に記載の組み合わせを表す。 In the formula, the JLA group, (E 1 ) n , Q, D, G and m represent the combinations described in the following [Table 7] to [Table 10].
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000057
　式（Ａ－２）で表される化合物。 Compound represented by formula (A-2).
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000058
　式中のＪ－Ｌ－Ａ基、（Ｅ１）n、Ｑ、Ｄ、Ｇ及びｍは、下記の〔表１１〕～〔表１２〕に記載の組み合わせを表す。 In the formula, the JLA group, (E 1 ) n , Q, D, G and m represent the combinations described in the following [Table 11] to [Table 12].
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000060
　式（Ａ－３）で表される化合物。 Compound represented by formula (A-3).
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000061
　式中のＪ－Ｌ基、（Ｅ１）n、Ｑ、Ｄ、Ｇ及びｍは、下記の〔表１３〕～〔表１６〕に記載の組み合わせを表す。 The JL group, (E 1 ) n , Q, D, G and m in the formula represent the combinations described in the following [Table 13] to [Table 16].
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000065
　式（Ａ－４）で表される化合物。 Compound represented by formula (A-4).
Figure JPOXMLDOC01-appb-C000066
Figure JPOXMLDOC01-appb-C000066
　式中のＪ－Ｌ基、Ｅ１、Ｑ、Ｄ、Ｇ及びｍは、下記の〔表１７〕～〔表１８〕に記載の組み合わせを表す。 The JL group, E 1 , Q, D, G and m in the formula represent the combinations described in the following [Table 17] to [Table 18].
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000068
　式（Ａ－５）で表される化合物。 Compound represented by formula (A-5).
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000069
　式中のＪ－Ｌ－Ａ基、（Ｅ１）n、Ｒｘ、Ｒｙ、Ｄ、Ｇ及びｍは、下記の〔表１９〕～〔表２２〕に記載の組み合わせを表す。 In the formula, the JLA group, (E 1 ) n , R x , R y , D, G and m represent the combinations described in the following [Table 19] to [Table 22].
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000073
式（Ａ－６）で表される化合物。 A compound represented by formula (A-6).
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000074
式中のＪ－Ｌ－Ａ基、Ｅ１、Ｒｘ、Ｒｙ、Ｄ、Ｇ及びｍは、下記の〔表２３〕～〔表２４〕に記載の組み合わせを表す。 In the formula, JLA group, E 1 , R x , R y , D, G and m represent the combinations described in the following [Table 23] to [Table 24].
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000076
　〔表７〕～〔表２４〕に記載した本発明化合物の物性値を下記の〔表２５〕に示す。 The physical properties of the compounds of the present invention described in [Table 7] to [Table 24] are shown in [Table 25] below.
Figure JPOXMLDOC01-appb-T000077
Figure JPOXMLDOC01-appb-T000077
　次に本発明化合物の製剤例を示す。なお、部は重量部を表す。 Next, formulation examples of the compound of the present invention are shown. In addition, a part represents a weight part.
　製剤例１
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 １０部を、キシレン３５部とＮ，Ｎ－ジメチルホルムアミド３５部との混合物に溶解し、ポリオキシエチレンスチリルフェニルエーテル１４部およびドデシルベンゼンスルホン酸カルシウム６部を加え、混合して各々の乳剤を得る。 Formulation Example 1
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 10 parts of any one of 1 to 6-34 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added. In addition, each emulsion is obtained by mixing.
　製剤例２
　ラウリル硫酸ナトリウム４部、リグニンスルホン酸カルシウム２部、合成含水酸化珪素微粉末２０部および珪藻土５４部を混合し、更に上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 ２０部を加え、混合して各々の水和剤を得る。 Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of a synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth were mixed, and the above-mentioned compounds 1-1 to 1-68, compounds 2-1 to 2-34, 20 parts of any one of compounds 3-1 to 3-68, compounds 4-1 to 4-34, compounds 5-1 to 5-102 and compounds 6-1 to 6-34 are added and mixed to Get wettable powder.
　製剤例３
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 ２部に、合成含水酸化珪素微粉末１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部およびカオリンクレー６５部を加え混合する。ついで、この混合物に適当量の水を加え、さらに攪拌し、造粒機で製粒し、通風乾燥して各々の粒剤を得る。 Formulation Example 3
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 1 part of any one of 1 to 6-34 is mixed with 1 part of synthetic hydrous silicon fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay. 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.
　製剤例４
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 １部を適当量のアセトンに溶解し、これに合成含水酸化珪素微粉末５部、ＰＡＰ０．３部およびフバサミクレー９３．７部を加え、充分攪拌混合し、アセトンを蒸発除去して各々の粉剤を得る。 Formulation Example 4
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 1 part of any one of 1 to 6-34 was dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydrous fine powder, 0.3 part of PAP and 93.7 parts of fusami clay were added, and the mixture was sufficiently stirred and mixed. Acetone is removed by evaporation to obtain each powder.
　製剤例５
　ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩およびホワイトカーボンの混合物（重量比１：１）３５部と、上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 １０部と、水５５部とを混合し、湿式粉砕法で微粉砕することにより、各々の製剤を得る。 Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), the above-mentioned compounds 1-1 to 1-68, compounds 2-1 to 2-34, compounds 3-1 to 3 -68, compound 4-1 to 4-34, compound 5-1 to 5-102, compound 6-1 to 6-34 10 parts of any one and water 55 parts are mixed, and wet pulverization method is used. Each preparation is obtained by fine grinding.
　製剤例６
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 ０．１部をキシレン５部およびトリクロロエタン５部に溶解し、これを脱臭灯油８９．９部に混合して各々の油剤を得る。 Formulation Example 6
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 0.1 part of any one of 1 to 6-34 is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of deodorized kerosene to obtain each oil agent.
　製剤例７
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 １０ｍｇをアセトン０．５ｍｌに溶解し、この溶液を、動物用固形飼料粉末（飼育繁殖用固形飼料粉末ＣＥ－２、日本クレア株式会社商品）５ｇに処理し、均一に混合する。ついでアセトンを蒸発乾燥させて各々の毒餌を得る。 Formulation Example 7
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 10 mg of any one of 1 to 6-34 is dissolved in 0.5 ml of acetone, and this solution is treated with 5 g of animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd.). Mix evenly. Then, acetone is evaporated to dryness to obtain each poisonous bait.
　製剤例８
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 ０．１部、ネオチオゾール（中央化成株式会社）４９．９部をエアゾール缶に入れ、エアゾールバルブを装着した後、ジメチルエーテル２５部、ＬＰＧ２５部を充填し振とうを加え、アクチュエータを装着することで油剤エアゾールを得る。 Formulation Example 8
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- Put 1 part of 1 to 6-34 0.1 part and 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) into an aerosol can, attach an aerosol valve, then fill with 25 parts of dimethyl ether and 25 parts of LPG and shake. And an oil aerosol is obtained by mounting the actuator.
　製剤例９
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種 ０．６部、ＢＨＴ（２，６－ジ－tert－ブチル－４－メチルフェノール）０．０１部、キシレン５部、脱臭灯油３．３９部および乳化剤｛アトモス３００（アトモスケミカル社登録商標名）｝１部を混合溶解したものと、蒸留水５０部とをエアゾール容器に充填し、バルブを装着した後、該バルブを通じて噴射剤（ＬＰＧ）４０部を加圧充填して水性エアゾールを得る。
製剤例１０
　上述の化合物１－１から１－６８、化合物２－１から２－３４、化合物３－１から３－６８、化合物４－１から４－３４、化合物５－１から５－１０２および化合物６－１から６－３４のいずれか１種を５部及びフェリムゾン５部を、ラウリル硫酸ナトリウム４部、リグニンスルホン酸カルシウム２部、合成含水酸化珪素微粉末２０部及び珪藻土残部を混合した中に加え、よく攪拌混合して水和剤１００部を得る。
製剤例１１～２５
　フェリムゾン５部に代えて、［表２６］記載のそれぞれの化合物及び使用量で適用した以外は製剤例１０と同様の操作を行い、それぞれの水和剤１００部を得る。 Formulation Example 9
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- 1 to 6-34, 0.6 part, BHT (2,6-di-tert-butyl-4-methylphenol) 0.01 part, xylene 5 parts, deodorized kerosene 3.39 parts and emulsifier { Atmos 300 (registered trade name of Atmos Chemical Co., Ltd.) Pressure filling to obtain an aqueous aerosol.
Formulation Example 10
Compounds 1-1 to 1-68, Compounds 2-1 to 2-34, Compounds 3-1 to 3-68, Compounds 4-1 to 4-34, Compounds 5-1 to 5-102 and Compound 6- Add 5 parts of any one of 1 to 6-34 and 5 parts of ferrimzone into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon hydroxide fine powder and the remainder of diatomaceous earth, Mix well and obtain 100 parts of wettable powder.
Formulation Examples 11-25
Instead of 5 parts of ferrimzone, the same operation as in Preparation Example 10 was carried out except that each compound and the amount used described in [Table 26] were applied to obtain 100 parts of each wettable powder.
Figure JPOXMLDOC01-appb-T000078
Figure JPOXMLDOC01-appb-T000078
　次に、本発明化合物の有害生物防除効力を試験例により示す。 Next, the pest control effect of the compound of the present invention is shown by test examples.
　試験例１
　製剤例５により得られた本発明化合物の製剤を本発明化合物の濃度が５００ｐｐｍとなるように水で希釈し、試験用薬液を調製した。 Test example 1
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 500 ppm to prepare a test drug solution.
　ポリエチレンカップに植えた第２葉展開期のイネ幼苗に、上記試験用薬液１０ｍｌを散布した。風乾後、トビイロウンカの３～４齢幼虫を２０頭放して、２５℃の温室内に保管した。６日後イネに寄生したトビイロウンカの数を調査し、下式により防除価を求めた。 10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the brown planthopper were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthoppers infested with rice was investigated, and the control value was determined by the following formula.
　防除価（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
なお、式中の文字は以下の意味を表す。 Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
　　　Ｃｂ：無処理区の処理前の虫数
　　　Ｃａｉ：無処理区の観察時の虫数
　　　Ｔｂ：処理区の処理前の虫数
　　　Ｔａｉ：処理区の観察時の虫数
　その結果、下記の本発明化合物の試験用散布液の処理区が、防除価９０％以上を示した。
化合物２－１、２－７、２－８、２－１０、５－１、５－１８。 Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compound of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.
Compounds 2-1, 2-7, 2-8, 2-10, 5-1, 5-18.
　試験例２
　製剤例５により得られた本発明化合物の製剤を本発明化合物の濃度が５００ｐｐｍとなるように水で希釈し、試験用散布液を調製した。 Test example 2
The formulation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 500 ppm to prepare a test spray solution.
　一方、プラスチックカップに植えたキュウリ幼苗（第１本葉展開期）にワタアブラムシ約３０頭を接種し、１日間放置した。この幼苗に、前記希釈液２０ｍｌを各々散布した。 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. Each of the seedlings was sprayed with 20 ml of the diluent.
　散布６日後に該キュウリの葉上に寄生したワタアブラムシ生存虫数を調査し、以下の式により防除価を求めた。 6 days after spraying, the number of live cotton aphids that parasitized on the cucumber leaves was investigated, and the control value was determined by the following formula.
　防除価（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
なお、式中の文字は以下の意味を表す。 Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
　　　Ｃｂ：無処理区の処理前の虫数
　　　Ｃａｉ：無処理区の観察時の虫数
　　　Ｔｂ：処理区の処理前の虫数
　　　Ｔａｉ：処理区の観察時の虫数
　その結果、下記の本発明化合物の試験用散布液の処理区が、防除価９０％以上を示した。
化合物２－１、２－２、２－７、２－１０、５－１。 Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compound of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.
Compounds 2-1, 2-2, 2-7, 2-10, 5-1.
　試験例３
　製剤例５により得られた本発明化合物の製剤を本発明化合物の濃度が２００ｐｐｍとなるように水で希釈し、試験用薬液を調製した。 Test example 3
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 200 ppm to prepare a test drug solution.
　ポリエチレンカップに植えた第２葉展開期のイネ幼苗に、上記試験用薬液１０ｍｌを散布した。風乾後、トビイロウンカの３～４齢幼虫を２０頭放して、２５℃の温室内に保管した。６日後イネに寄生したトビイロウンカの数を調査し、下式により防除価を求めた。 10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the brown planthopper were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthoppers infested with rice was investigated, and the control value was determined by the following formula.
　防除価（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
なお、式中の文字は以下の意味を表す。 Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
　　　Ｃｂ：無処理区の処理前の虫数
　　　Ｃａｉ：無処理区の観察時の虫数
　　　Ｔｂ：処理区の処理前の虫数
　　　Ｔａｉ：処理区の観察時の虫数
　その結果、下記の本発明化合物の試験用散布液の処理区が、防除価９０％以上を示した。 Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compound of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.
　化合物３－３５。 Compound 3-35.
　試験例４
　製剤例５により得られた本発明化合物の製剤を本発明化合物の濃度が２００ｐｐｍとなるように水で希釈し、試験用散布液を調製した。 Test example 4
The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the concentration of the compound of the present invention was 200 ppm to prepare a test spray solution.
　一方、プラスチックカップに植えたキュウリ幼苗（第１本葉展開期）にワタアブラムシ約３０頭を接種し、１日間放置した。この幼苗に、前記希釈液２０ｍｌを各々散布した。 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. Each of these seedlings was sprayed with 20 ml of the diluted solution.
　散布６日後に該キュウリの葉上に寄生したワタアブラムシ生存虫数を調査し、以下の式により防除価を求めた。 6 days after spraying, the number of live cotton aphids that parasitized on the cucumber leaves was investigated, and the control value was determined by the following formula.
　防除価（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
なお、式中の文字は以下の意味を表す。 Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
　　　Ｃｂ：無処理区の処理前の虫数
　　　Ｃａｉ：無処理区の観察時の虫数
　　　Ｔｂ：処理区の処理前の虫数
　　　Ｔａｉ：処理区の観察時の虫数
　その結果、下記の本発明化合物の試験用散布液の処理区が、防除価９０％以上を示した。 Cb: number of insects before treatment in the untreated group Cai: number of insects when observed in the untreated group Tb: number of insects before treatment in the treated group Tai: number of insects when observed in the treated group As a result, the following compound of the present invention The treatment group of the spray liquid for the test showed a control value of 90% or more.
　化合物３－３５。 Compound 3-35.
　本発明化合物は、有害生物の防除に有用である。 The compound of the present invention is useful for controlling pests.

Claims (21)

  1. 式（１）
    Figure JPOXMLDOC01-appb-C000001
     〔式中、
    　Ｈｅｔは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる１個以上のヘテロ原子を含む５または６員へテロ芳香環を表し（ここで、ＡおよびＱはそれぞれ、該５または６員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５または６員へテロ芳香環上で互いに隣接することはない。該５または６員へテロ芳香環は、Ａ及びＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝、－Ｏ－、－Ｓ－および－ＮＥ２－からなる群より選ばれる３もしくは４個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子を表し、Ｅ２は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基を表す。）、
    　Ｊは、下式Ｊ１またはＪ２：
    Figure JPOXMLDOC01-appb-C000002
     （式中、
    　Ｒ1およびＲ2は、同一または相異なり、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ３アルキル基を表し、
    　Ｒ3は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６鎖式炭化水素基、ハロゲン原子または水素原子を表し、
    　Ｒ4およびＲ5は、同一または相異なり、Ｃ１－Ｃ３アルキル基を表し、
    　Ｒ6は、水素原子またはＣ１－Ｃ６鎖式炭化水素基を表す。）で示される基を表し、
    　Ｌは、単結合または１個以上のハロゲン原子を有していてもよいＣ１－Ｃ３アルキレン基を表し、
    　Ａは、ＡがＨｅｔで表される該５または６員へテロ芳香環を構成する炭素原子に結合する場合には、単結合、－Ｏ－、または－Ｓ（Ｏ）x－を表し（ここで、ｘは、０、１または２を表す。）、ＡがＨｅｔで表される該５または６員へテロ芳香環を構成する窒素原子に結合する場合には、単結合を表し、
    　Ｑは、ＱがＨｅｔで表される該５または６員へテロ芳香環を構成する炭素原子に結合する場合には、下式Ｑ１、Ｑ２、Ｑ３またはＱ４：
    Figure JPOXMLDOC01-appb-C000003
     （式中、
    　ＲxおよびＲyは、同一または相異なり、＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、シアノ基、ハロゲン原子、水素原子またはシクロプロピル基を表し、
    　ｙは０、１または２を表し、
    　Ｒzは、＜群α＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1、－Ｓ（Ｏ）2－Ｔ2、水素原子またはシクロプロピル基を表し、
    　Ｔ1は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ１２ジアルキルアミノ基、水酸基、アミノ基、水素原子またはシクロプロピル基を表し、
    　Ｔ2は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基を表す。）で示される基を表し、
    　ＱがＨｅｔで表される該５または６員へテロ芳香環を構成する窒素原子に結合する場合には、Ｑは式Ｑ１で示される基を表し、
    　Ｇは、水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸基、メルカプト基もしくはアミノ基を表すか、または、下式Ｇ１、Ｇ２、Ｇ３もしくはＧ４：
    Figure JPOXMLDOC01-appb-C000004
     ｛式中、
    　Ｒaは、＜群β＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、シクロプロピル基または－Ｃ（Ｏ）－Ｔ1を表し、
    　Ｒbは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1、－Ｓ（Ｏ）2－Ｔ2、Ｃ３－Ｃ９トリアルキルシリル基またはシクロプロピル基を表し、
    　Ｒcは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1またはシクロプロピル基を表し、
    　ｚは０、１または２を表し、
    　Ｒdは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、－Ｃ（Ｏ）－Ｔ1、－Ｓ（Ｏ）2－Ｔ2またはシクロプロピル基を表し、
    　Ｒeは、＜群γ＞より選ばれる１個以上の原子もしくは基を有していてもよいＣ１－Ｃ６鎖式炭化水素基、水素原子またはシクロプロピル基を表す。
    　（ここで、Ｔ1およびＴ2は前述と同義であるが、Ｇが式Ｇ２、Ｇ３またはＧ４で示される基の場合には、Ｔ1は、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ６アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ１２ジアルキルアミノ基、アミノ基、水素原子またはシクロプロピル基を表す。）｝で示される基を表し、
    　Ｄは－Ｎ＝または－ＣＨ＝を表し、
    　ｍは０または１を表す。
    ＜群α＞：ハロゲン原子、シアノ基およびシクロプロピル基からなる群、
    ＜群β＞：１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルチオ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルホニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ８ジアルキルアミノ基、ハロゲン原子、シアノ基、Ｃ３－Ｃ９トリアルキルシリル基およびシクロプロピル基からなる群、
    ＜群γ＞：１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルコキシ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルチオ基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルフィニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルスルホニル基、１個以上のハロゲン原子を有していてもよいＣ１－Ｃ４アルキルアミノ基、１個以上のハロゲン原子を有していてもよいＣ２－Ｃ８ジアルキルアミノ基、フェニル基（該フェニル基は、メチル基、メトキシ基、塩素原子およびニトロ基からなる群より選ばれる１個以上の基を有していてもよい。）、ハロゲン原子、シアノ基、Ｃ３－Ｃ９トリアルキルシリル基およびシクロプロピル基からなる群。〕
    で示されるヘテロ芳香環化合物。     Formula (1)
    Figure JPOXMLDOC01-appb-C000001
     [Where,
    Het represents a 5- or 6-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (wherein A and Q are the 5- or 6-membered members, respectively) The atom bonded to the carbon atom or nitrogen atom constituting the heteroaromatic ring, and the atom bonded to A and the atom bonded to Q are not adjacent to each other on the 5- or 6-membered heteroaromatic ring. The 6-membered heteroaromatic ring has 3 or 4 atoms selected from the group consisting of —CE 1 ═, —N═, —O—, —S— and —NE 2 — together with atoms to which A and Q are bonded. Or E 1 represents a C1-C2 alkyl group which may have one or more halogen atoms, a hydrogen atom or a halogen atom, and E 2 has one or more halogen atoms. Represents a C1-C2 alkyl group ),
    J is the following formula J1 or J2:
    Figure JPOXMLDOC01-appb-C000002
     (Where
    R 1 and R 2 are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
    R 3 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom,
    R 4 and R 5 are the same or different and represent a C1-C3 alkyl group,
    R 6 represents a hydrogen atom or a C1-C6 chain hydrocarbon group. ) Represents a group represented by
    L represents a single bond or a C1-C3 alkylene group which may have one or more halogen atoms,
    A represents a single bond, —O—, or —S (O) x — when A is bonded to the carbon atom constituting the 5- or 6-membered heteroaromatic ring represented by Het (here, X represents 0, 1 or 2.), when A is bonded to the nitrogen atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, it represents a single bond;
    When Q is bonded to a carbon atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, the following formula Q1, Q2, Q3 or Q4:
    Figure JPOXMLDOC01-appb-C000003
     (Where
    R x and R y are the same or different and each may have one or more atoms or groups selected from <Group α>, C1-C6 chain hydrocarbon group, cyano group, halogen atom, hydrogen atom Or a cyclopropyl group,
    y represents 0, 1 or 2;
    R z is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group α>, —C (O) —T 1 , —S (O) 2 —. T 2 represents a hydrogen atom or a cyclopropyl group,
    T 1 has a C1-C6 alkyl group which may have one or more halogen atoms, a C1-C6 alkoxy group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C6 alkylamino group, an optionally substituted C2-C12 dialkylamino group, a hydroxyl group, an amino group, a hydrogen atom or a cyclopropyl group,
    T 2 represents a C1-C6 alkyl group which may have one or more halogen atoms. ) Represents a group represented by
    When Q is bonded to a nitrogen atom constituting the 5- or 6-membered heteroaromatic ring represented by Het, Q represents a group represented by the formula Q1;
    G represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group or an amino group, or the following formulas G1, G2, G3 or G4:
    Figure JPOXMLDOC01-appb-C000004
     {Where,
    R a represents a C1-C6 chain hydrocarbon group, a cyclopropyl group or —C (O) —T 1 which may have one or more atoms or groups selected from <Group β>
    R b is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, —C (O) —T 1 , —S (O) 2 —. T 2 represents a C3-C9 trialkylsilyl group or a cyclopropyl group,
    R c represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from <Group γ>, —C (O) —T 1 or a cyclopropyl group;
    z represents 0, 1 or 2;
    R d is a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from <Group γ>, —C (O) —T 1 , —S (O) 2 —. Represents T 2 or a cyclopropyl group,
    R e represents a C1-C6 chain hydrocarbon group, a hydrogen atom or a cyclopropyl group which may have one or more atoms or groups selected from <Group γ>.
    (Here, T 1 and T 2 are as defined above, but when G is a group represented by the formula G2, G3 or G4, T 1 may have one or more halogen atoms. A good C1-C6 alkyl group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, one or more Represents a C2-C12 dialkylamino group optionally having a halogen atom, an amino group, a hydrogen atom or a cyclopropyl group.)}
    D represents —N═ or —CH═,
    m represents 0 or 1;
    <Group α>: Group consisting of halogen atom, cyano group and cyclopropyl group,
    <Group β>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms A group consisting of an amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, a C3-C9 trialkylsilyl group, and a cyclopropyl group;
    <Group γ>: C1-C4 alkoxy group which may have one or more halogen atoms, C1-C4 alkylthio group which may have one or more halogen atoms, one or more halogen atoms C1-C4 alkylsulfinyl group which may have one, C1-C4 alkylsulfonyl group which may have one or more halogen atoms, C1-C4 alkyl which may have one or more halogen atoms An amino group, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a phenyl group (the phenyl group is one selected from the group consisting of a methyl group, a methoxy group, a chlorine atom and a nitro group) And a group consisting of a halogen atom, a cyano group, a C3-C9 trialkylsilyl group and a cyclopropyl group. ]
    The heteroaromatic ring compound shown by these.
  2. Ｈｅｔが下式Ｈ１またはＨ２：
    Figure JPOXMLDOC01-appb-C000005
     （式中、
    　Ｘ１、Ｘ２、Ｘ３およびＸ４は、同一または相異なり、－ＣＥ１＝または－Ｎ＝を表す。
    　但し、Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの少なくとも１つは－Ｎ＝を表す。）
    で示される環である請求項１に記載のヘテロ芳香環化合物。     Het has the following formula H1 or H2:
    Figure JPOXMLDOC01-appb-C000005
     (Where
    X 1 , X 2 , X 3 and X 4 are the same or different and represent —CE 1 ═ or —N═.
    Provided that at least one of X 1, X 2, X 3 and X 4 represent -N =. )
    The heteroaromatic ring compound of Claim 1 which is a ring shown by these.
  3. Ｘ１、Ｘ２、Ｘ３およびＸ４のうちの１つが－Ｎ＝であり、それ以外が、同一または相異なり、－ＣＥ１＝である請求項２に記載のヘテロ芳香環化合物。 The heteroaromatic compound according to claim 2 , wherein one of X 1 , X 2 , X 3 and X 4 is -N =, the other is the same or different, and -CE 1 =.
  4. Ｈｅｔが式Ｈ１で示される環である請求項３に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 3, wherein Het is a ring represented by the formula H1.
  5. Ｈｅｔが下式Ｈ３、Ｈ４またはＨ５：
    Figure JPOXMLDOC01-appb-C000006
     （式中、
    　Ｙ１、Ｙ２およびＹ３のうちの１つは、－Ｏ－、－Ｓ－または－ＮＥ２－を表し、残りの２つは、同一または相異なり、－ＣＥ１＝または－Ｎ＝を表し、
    　Ｚ１、Ｚ２およびＺ３は、同一または相異なり、－ＣＥ１＝または－Ｎ＝を表す。）
    で示される環である請求項１に記載のヘテロ芳香環化合物。     Het is represented by the following formula H3, H4 or H5:
    Figure JPOXMLDOC01-appb-C000006
     (Where
    One of Y 1 , Y 2 and Y 3 represents —O—, —S— or —NE 2 —, and the other two are the same or different and represent —CE 1 ═ or —N═. Represent,
    Z 1 , Z 2 and Z 3 are the same or different and represent —CE 1 ═ or —N═. )
    The heteroaromatic ring compound of Claim 1 which is a ring shown by these.
  6. Ｈｅｔが式Ｈ３で示される環である請求項５に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 5, wherein Het is a ring represented by the formula H3.
  7. Ｙ１、Ｙ２およびＹ３のうちの１つが－Ｓ－である請求項６に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 6, wherein one of Y 1 , Y 2 and Y 3 is -S-.
  8. Ｙ１、Ｙ２およびＹ３のうちの１つが－Ｓ－であり、それ以外が、同一または相異なり、－ＣＥ１＝である請求項７に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 7, wherein one of Y 1 , Y 2 and Y 3 is -S-, and the others are the same or different and -CE 1 =.
  9. Ｙ１が－Ｓ－である請求項７に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 7, wherein Y 1 is -S-.
  10. Ｙ１が－Ｓ－であり、Ｙ２およびＹ３が、同一または相異なり、－ＣＥ１＝である請求項９に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 9, wherein Y 1 is -S-, Y 2 and Y 3 are the same or different and -CE 1 =.
  11. Ｈｅｔが式Ｈ４で示される環である請求項５に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 5, wherein Het is a ring represented by the formula H4.
  12. Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、かつ、Ｚ３が－ＣＥ１＝または－Ｎ＝であるか、あるいは、Ｚ１が－ＣＥ１＝であり、Ｚ２が－Ｎ＝であり、かつ、Ｚ３が－ＣＥ１＝である請求項１１に記載のヘテロ芳香環化合物。 Z 1 is -N =, Z 2 is -CE 1 = and Z 3 is -CE 1 = or -N =, or Z 1 is -CE 1 = and Z 2 There is -N =, and heteroaromatic ring compound of claim 11 Z 3 is -CE 1 =.
  13. Ｚ１が－Ｎ＝であり、Ｚ２およびＺ３が同一または相異なり－ＣＥ１＝であるか、あるいは、Ｚ２が－Ｎ＝であり、Ｚ１およびＺ３が同一または相異なり－ＣＥ１＝である請求項１２に記載のヘテロ芳香環化合物。 Z 1 is -N = and Z 2 and Z 3 are the same or different -CE 1 =, or Z 2 is -N = and Z 1 and Z 3 are the same or different -CE The heteroaromatic ring compound according to claim 12, wherein 1 =.
  14. Ｈｅｔが式Ｈ５で示される環である請求項５に記載のヘテロ芳香環化合物。 The heteroaromatic ring compound according to claim 5, wherein Het is a ring represented by the formula H5.
  15. Ｚ１が－Ｎ＝であり、Ｚ２が－ＣＥ１＝であり、かつ、Ｚ３が－ＣＥ１＝または－Ｎ＝であるか、あるいは、Ｚ１が－ＣＥ１＝であり、Ｚ２が－Ｎ＝であり、かつ、Ｚ３が－ＣＥ１＝である請求項１４に記載のヘテロ芳香環化合物。 Z 1 is -N =, Z 2 is -CE 1 = and Z 3 is -CE 1 = or -N =, or Z 1 is -CE 1 = and Z 2 The heteroaromatic ring compound according to claim 14, wherein is -N = and Z 3 is -CE 1 =.
  16. Ｚ１が－Ｎ＝であり、Ｚ２およびＺ３が同一または相異なり－ＣＥ１＝であるか、あるいは、Ｚ２が－Ｎ＝であり、Ｚ１およびＺ３が同一または相異なり－ＣＥ１＝である請求項１５に記載のヘテロ芳香環化合物。 Z 1 is -N = and Z 2 and Z 3 are the same or different -CE 1 =, or Z 2 is -N = and Z 1 and Z 3 are the same or different -CE The heteroaromatic ring compound according to claim 15, wherein 1 =.
  17. 　Ｈｅｔが、窒素原子、および硫黄原子からなる群より選ばれる１個以上のヘテロ原子を含む５または６員へテロ芳香環であり（ここで、ＡおよびＱはそれぞれ、該５または６員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５または６員へテロ芳香環上で互いに隣接することはない。該５または６員へテロ芳香環は、Ａ及びＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝および－Ｓ－からなる群より選ばれる３もしくは４個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子である。）、
    　Ｊが、式Ｊ１またはＪ２（Ｒ1およびＲ2が、同一または相異なり、Ｃ１－Ｃ３アルキル基であり、Ｒ3が、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒ4およびＲ5が、同一または相異なり、Ｃ１－Ｃ３アルキル基であり、Ｒ6が、Ｃ１－Ｃ６鎖式炭化水素基である。）で示される基であり、
    　Ｌが、単結合またはＣ１－Ｃ３アルキレン基であり、
    　Ａが単結合であり、
    　Ｑが式Ｑ１（ＲxおよびＲyが、水素原子である。）で示される基であり、
    　Ｇが、水素原子、ハロゲン原子、または、式Ｇ１、Ｇ２、Ｇ３もしくはＧ４｛Ｒaは、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒbは、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒcは、Ｃ１－Ｃ６鎖式炭化水素基であり、ｚが０、１または２であり、Ｒdが、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒeが、Ｃ１－Ｃ６鎖式炭化水素基である。｝で示される基であり、
    　Ｄが－ＣＨ＝であり、
    　ｍが０である請求項１記載のヘテロ芳香環化合物。     Het is a 5- or 6-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom (wherein A and Q are the 5- or 6-membered heteroaromatic ring, respectively) An atom to which A is bonded and an atom to which Q is bonded are not adjacent to each other on the 5- or 6-membered heteroaromatic ring, bonded to a carbon atom or a nitrogen atom constituting the aromatic ring. hetero aromatic ring together with the atoms to which a and Q are bonded, -CE 1 =, - N = is composed of three or four atoms or groups selected from the group consisting of and -S-, E 1 is one A C1-C2 alkyl group optionally having a halogen atom, a hydrogen atom or a halogen atom).
    J is the formula J1 or J2 (R 1 and R 2 are the same or different and are a C1-C3 alkyl group, R 3 is a C1-C6 chain hydrocarbon group, and R 4 and R 5 are The same or different, a C1-C3 alkyl group, and R 6 is a C1-C6 chain hydrocarbon group).
    L is a single bond or a C1-C3 alkylene group,
    A is a single bond,
    Q is a group represented by the formula Q1 (R x and R y are hydrogen atoms),
    G is a hydrogen atom, a halogen atom, or a formula G1, G2, G3 or G4 {R a is a C1-C6 chain hydrocarbon group, R b is a C1-C6 chain hydrocarbon group; R c is a C1-C6 chain hydrocarbon group, z is 0, 1 or 2, R d is a C1-C6 chain hydrocarbon group, and R e is a C1-C6 chain hydrocarbon group. It is a hydrogen group. }, And
    D is -CH =
    The heteroaromatic ring compound according to claim 1, wherein m is 0.
  18. 　Ｈｅｔが、窒素原子、および硫黄原子からなる群より選ばれる１個以上のヘテロ原子を含む５員へテロ芳香環であり（ここで、ＡおよびＱはそれぞれ、該５員へテロ芳香環を構成する炭素原子または窒素原子に結合し、Ａが結合した原子とＱが結合した原子とが該５員へテロ芳香環上で互いに隣接することはない。該５員へテロ芳香環は、Ａ及びＱが結合した原子と共に、－ＣＥ１＝、－Ｎ＝および－Ｓ－からなる群より選ばれる３個の原子または基から構成され、Ｅ１は１個以上のハロゲン原子を有していてもよいＣ１－Ｃ２アルキル基、水素原子またはハロゲン原子である。）、
    　Ｊが、式Ｊ１（Ｒ1およびＲ2が、同一または相異なり、Ｃ１－Ｃ３アルキル基であり、Ｒ3が、Ｃ１－Ｃ６鎖式炭化水素基である。）で示される基であり、
    　Ｌが、単結合またはＣ１－Ｃ３アルキレン基であり、
    　Ａが単結合であり、
    　Ｑが式Ｑ１（ＲxおよびＲyが、水素原子である。）で示される基であり、
    　Ｇが、水素原子、ハロゲン原子、または、式Ｇ２もしくはＧ３｛Ｒbは、Ｃ１－Ｃ６鎖式炭化水素基であり、Ｒcは、Ｃ１－Ｃ６鎖式炭化水素基であり、ｚが０である。｝で示される基であり、
    　Ｄが－ＣＨ＝であり、
    　ｍが０である請求項１記載のヘテロ芳香環化合物。     Het is a 5-membered heteroaromatic ring containing one or more heteroatoms selected from the group consisting of a nitrogen atom and a sulfur atom (wherein A and Q constitute the 5-membered heteroaromatic ring, respectively) The atom to which A is bonded and the atom to which Q is bonded are not adjacent to each other on the 5-membered heteroaromatic ring. It is composed of three atoms or groups selected from the group consisting of —CE 1 ═, —N═ and —S— together with an atom to which Q is bonded, and E 1 may have one or more halogen atoms A good C1-C2 alkyl group, a hydrogen atom or a halogen atom).
    J is a group represented by the formula J1 (wherein R 1 and R 2 are the same or different and are a C1-C3 alkyl group and R 3 is a C1-C6 chain hydrocarbon group);
    L is a single bond or a C1-C3 alkylene group,
    A is a single bond,
    Q is a group represented by the formula Q1 (R x and R y are hydrogen atoms),
    G is a hydrogen atom, a halogen atom, or a formula G2 or G3 {R b is a C1-C6 chain hydrocarbon group, R c is a C1-C6 chain hydrocarbon group, and z is 0 is there. }, And
    D is -CH =
    The heteroaromatic ring compound according to claim 1, wherein m is 0.
  19. 請求項１～１８のいずれか一項に記載のヘテロ芳香環化合物と不活性担体とを含有する有害生物防除剤。 A pest control agent comprising the heteroaromatic ring compound according to any one of claims 1 to 18 and an inert carrier.
  20. 有害生物を防除するための請求項１～１８のいずれか一項に記載のヘテロ芳香環化合物の使用。 Use of the heteroaromatic ring compound according to any one of claims 1 to 18 for controlling pests.
  21. 請求項１～１８のいずれか一項に記載のヘテロ芳香環化合物の有効量を有害生物又は有害生物の生息場所に施用する工程を含む有害生物の防除方法。 A pest control method comprising a step of applying an effective amount of the heteroaromatic compound according to any one of claims 1 to 18 to a pest or a pest habitat.
PCT/JP2011/073451 2010-10-14 2011-10-12 Heteroaromatic ring compound and use thereof for pest control WO2012050141A1 (en)

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