WO2012073995A1 - Composé cyclique hétéroaromatique et son application antiparasitaire - Google Patents

Composé cyclique hétéroaromatique et son application antiparasitaire Download PDF

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WO2012073995A1
WO2012073995A1 PCT/JP2011/077640 JP2011077640W WO2012073995A1 WO 2012073995 A1 WO2012073995 A1 WO 2012073995A1 JP 2011077640 W JP2011077640 W JP 2011077640W WO 2012073995 A1 WO2012073995 A1 WO 2012073995A1
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group
formula
compound
halogen atoms
represented
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PCT/JP2011/077640
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Japanese (ja)
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舞衣 伊藤
池上　宏
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住友化学株式会社
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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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond

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.
  • Patent Document 1 describes a compound having a thiazole ring and a pyridine ring in the molecule.
  • Patent Document 2 describes a compound having a pyrazole ring and a pyrimidine ring in the molecule.
  • An object of the present invention is to provide a novel compound having a controlling activity against pests.
  • the present inventor found that the compound represented by the following formula (1) has a control effect on pests, and further studied. As a result, the present invention has been completed.
  • Het is represented by the following formula H1, H2, H3, H4 or H5:
  • Y 1 represents —O—, —S— or —NE 2 —
  • Y 2 and Y 3 are the same or different and represent —CE 1 ⁇ or —N ⁇
  • at least one of Y 2 and Y 3 Are —CE 1 ⁇
  • Z 1 , Z 2 and Z 3 are the same or different and represent —CE 1 ⁇ or —N ⁇
  • E 1 has one or more halogen atoms
  • E 2 represents a C1-C2 alkyl group which may have one or more halogen atoms.
  • the mark represents the position where A is combined.
  • ⁇ represents a 5-membered heterocycle represented by 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 each represents a methyl group or an ethyl group
  • R 6 represents a hydrogen atom or a C1-C6 chain hydrocarbon group.
  • 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 Het is a group represented by the formula H1, H2, H3 or H5 (where x represents 0, 1 or 2).
  • 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 2 , —S (O) 2 —.
  • T 3 represents a C3-C9 trialkylsilyl group or a cyclopropyl group
  • R c represents a C1-C6 chain hydrocarbon group which may have one or more atoms or groups selected from ⁇ Group ⁇ >, —C (O) —T 2 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 2 , —S (O) 2 —.
  • R e represents a C1-C6 chain hydrocarbon group, hydrogen atom or cyclopropyl group which may have one or more atoms or groups selected from ⁇ 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 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 3 represents a C1-C6 alkyl group which may have one or more halogen atoms.
  • Represents a group represented by D represents —N ⁇ or —CH ⁇ , m represents 0 or 1;
  • Het is a group represented by the formula H1, Y 1 is —S—, Y 2 and Y 3 are —CH ⁇ , A is —O—, L is a single bond, A compound in which J is a group represented by formula J1, R 1 , R 2 and R 3 are all methyl groups, G is a hydrogen atom, D is —CH ⁇ and m is 0 , (2) Het is a group represented by the formula H1, Y 1 is —O—, Y 2 and Y 3 are —CH ⁇ , A and L are single bonds, and J is represented by the formula J2.
  • a compound in which D is -N and m is 0, (5) Het is a group represented by the formula H4, Z 1 is —N ⁇ , Z 2 and Z 3 are —CH ⁇ , A and L are single bonds, and J is represented by the formula J1.
  • R 1 and R 2 are both methyl groups
  • R 3 is a hydrogen atom or a methyl group
  • G is a hydrogen atom
  • D is —CH ⁇ or —N ⁇
  • Het is a group represented by the formula H5, Z 1 is —N ⁇ , Z 2 is —C (CH 3 ) ⁇ , and Z 3 is —CH ⁇ .
  • A is —O—, L is a single bond, 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 heteroaromatic ring compound represented by the following (hereinafter referred to as the present compound).
  • [Item 2] The heteroaromatic ring compound according to [Item 1], wherein Het is a group represented by the formula H1.
  • [Claim 3] The heteroaromatic ring compound according to [Claim 2], wherein Y 1 is —S— or —O—.
  • a pest control agent comprising the heteroaromatic ring compound according to any one of [Item 1] to [Item 13] and an inert carrier.
  • [Item 15] Use of the heteroaromatic ring compound according to any one of [Item 1] to [Item 13] for controlling pests.
  • [Item 16] A method for controlling pests comprising a step of applying an effective amount of the heteroaromatic ring compound according to any one of [Item 1] to [Item 13] 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 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.
  • a C1-C6 alkyl group such as butyl group, isobutyl group, sec-butyl group and 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 A C6 alkyl group; One or more atoms selected from ⁇ 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-fluor
  • 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, 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- (
  • 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.
  • examples of the “C3-C9 trialkylsilyl group” include a trimethylsilyl group, 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.
  • Examples of the “C2-C12 dialkylamino group optionally having one or more halogen atoms” in the compound of the present invention include N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl group.
  • An amino group and an N-methyl-N- (2,2,2-trifluoroethyl) amino group can 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.
  • Examples of the “C2-C8 dialkylamino group optionally having one or more halogen atoms” in the compounds of the present invention include N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropyl group.
  • An amino group and an N-methyl-N- (2,2,2-trifluoroethyl) amino group can be mentioned.
  • the “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)” is, for example, a phenyl group 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 4-nitrophenyl group, 2-nitrophenyl group, 4-chlorophenyl group, 2-chlorophenyl group, 2,6-dichlorophenyl group and 4-methylphenyl group.
  • each E 1 group may be the same or different.
  • 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 (R 1 and R 2 are both methyl groups)
  • R 3 is a hydrogen atom, a methyl group, or an ethyl group.
  • R 4 , R 5, and R 6 are all methyl groups
  • [Claim 1] The compound according to any one of [Aspect A] to [Aspect Z] and [Aspect 1] to [Aspect 23];
  • L is —CH 2 —
  • A is a single bond
  • J is a group represented by the formula J1 (R 1 and R 2 are both methyl groups
  • R 3 is a hydrogen atom, A methyl group or an ethyl group) or a group represented by formula J2 (wherein R 4 , R 5 and R 6 are all
  • G is a group represented by the formula G2, and R b is a C1-C6 chain hydrocarbon group which may have 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 which may have one or more atoms or groups selected from ⁇ Group ⁇ > [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
  • G is hydrogen atom, fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, propyl group, iso
  • 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 which may have one or more atoms or groups selected from ⁇ Group ⁇ > [Claim 1] and [Aspect A] to [Aspect Z] A compound according to any of the above;
  • 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 methyl group, an ethyl group, a propyl group or an isopropyl group [Claim 1] and the compound according to any one of [Aspect A] to [Aspect Z];
  • [Claim 1] which is a group and the compound according to any one of [Aspect A] to [Aspect Z];
  • any one of [Claim 1] and [Aspect A] to [Aspect Z] wherein G is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, or a 2,2,2-trifluoroethoxy group A compound according to claim 1;
  • G is a
  • G is a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, or a 2,2,2-trifluoroethylthio group. Any one of the compounds; In the formula (1), G is a group represented by the 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] and [Aspect A ] To [Aspect Z]
  • 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
  • the compound of the present invention can be produced, for example, according to the following (Production Method 1) to (Production Method 9).
  • Het1 represents a group of the formula H1, H2, H3 or H4, Lg 1 is a chlorine atom, a bromine atom, It represents a leaving group such as an iodine atom or a trifluoromethanesulfonyloxy group, Lg 2 represents a B (OH) 2 group or a B (OR f ) 2 group (wherein R f may be the same or different) , A C1-C6 alkyl group, and two R f can be bonded to form a —CH 2 CH 2 — group or a —C (CH 3 ) 2 C (CH 3 ) 2 — group.
  • the compound of the present invention can produce compound (1a) by reacting compound (2) with the compound represented by formula (3) in the presence of a solvent, a catalyst and 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, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile, and the like.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • acetonitrile 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 methylene chloride and chloroform
  • acetonitrile aceton
  • Examples of the catalyst used in the reaction include palladium catalysts such as tetrakis (triphenylphosphine) palladium and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium methylene chloride complex.
  • the amount of the catalyst used is in the range of 0.0001 to 0.1 times mol for 1 mol of compound (2).
  • Examples of the base used in the reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, cesium carbonate, potassium tert-butoxide, potassium phosphate, and organic acid salts such as sodium acetate and potassium acetate. Is mentioned.
  • the amount of the base used is in the range of 0.5 to 10 times mol per mol of compound (2).
  • Compound (3) is usually used at a ratio of 1 mol per 1 mol of compound (2), but can be appropriately changed.
  • the reaction temperature in the reaction is usually in the range of 20 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.
  • the reaction is preferably performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the compound (1a) can be isolated by carrying out ordinary post-treatment operations.
  • Lg 3 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, paratoluene. It represents a leaving group such as a sulfonyloxy group or a trifluoromethanesulfonyloxy group.
  • the compound (1b) of the present invention can be produced by reacting the compound (4) and the compound (5) in the presence of a base.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent such as ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, chlorides, and the like.
  • halogenated hydrocarbons such as methylene and chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • 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 in a proportion of 1 mol to 10 mol with respect to compound (4).
  • Compound (5) is usually used at a ratio of 1 mol per 1 mol of compound (4), but can be appropriately changed.
  • the reaction temperature in the reaction between the compound (4) and the compound (5) is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.
  • the compound (1b) of the present invention can be isolated by performing ordinary post-treatment operations.
  • Lg 4 represents a leaving group such as a fluorine atom, a chlorine atom or a bromine atom.
  • the compound (1c) of the present invention can be produced by reacting the compound (6) and the compound (7) in the presence of a base.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent such as ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, chlorides, and the like.
  • halogenated hydrocarbons such as methylene and chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • 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 in a proportion of 1 mol to 10 mol with respect to compound (6).
  • Compound (7) is usually used in a ratio of 1 mol per 1 mol of compound (6), but can be appropriately changed.
  • the reaction temperature in the reaction of the compound (6) and the compound (7) is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.
  • the compound (1c) of the present invention can be isolated by performing ordinary post-treatment operations.
  • Het2 represents a group represented by the formula H1, H2 or H3, and L ′ represents a single bond or one or more halogens.
  • Lg 5 represents a leaving group such as a chlorine atom, a bromine atom or an iodine atom
  • R g represents a hydrogen atom, a methyl group, a methylthio group, a methoxy group, a phenyl group
  • Compound (10) can be produced by reacting compound (8) with an alkyllithium compound and then reacting the resulting reaction intermediate with an aldehyde represented by formula (9).
  • Two Lg 1 of the compound (8) may be the same or different.
  • 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.
  • alkyllithium compound used in the reaction examples include n-, sec- or tert-butyllithium, preferably n-butyllithium.
  • the alkyllithium compound is usually used at a ratio of 1 mol per 1 mol of the compound (8), but can be appropriately changed.
  • the reaction temperature in the reaction between the compound (8) and the alkyl lithium compound is usually in the range of ⁇ 78 ° C. to 0 ° C., and the reaction time is usually in the range of 1 hour from the instant.
  • 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 between the reaction intermediate and compound (8) 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 (10) 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.
  • This reaction can be produced by the production method of compound (1a) described in production method 1 or a method analogous thereto.
  • reaction can be prepared by a Barton-McCombie dehydroxylation reaction known to those skilled in the art.
  • Compound (14) can be produced by reacting compound (6) with dihalopyrimidine compound (13) in the presence of a base.
  • Two Lg 4 groups in the compound (13) may be different from each other, but a compound in which the two Lg 4 groups are both chlorine atoms is preferable.
  • 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, aromatic hydrocarbons such as toluene and xylene, methylene chloride, and the like.
  • Halogenated hydrocarbons such as chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • 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 in a proportion of 1 mol to 10 mol with respect to 1 mol of the compound (6).
  • Compound (13) is usually used at a ratio of 1 mol per 1 mol of compound (6), 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.
  • the compound (14) can be isolated by performing ordinary post-treatment operations.
  • the compound (1e) of the present invention can be produced by dehalogenating the compound (14).
  • 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 (14).
  • 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 present compound (1e) can be isolated by removing the catalyst by filtration and then performing a usual post-treatment operation.
  • R b1 has one or more atoms or groups selected from ⁇ Group ⁇ >.
  • R b2 represents an OH-protecting group (for example, a methyl group, a methoxymethyl group, a benzyl group, etc.).
  • the compound (1g ′) of the present invention can be produced by reacting the compound (1f) 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, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • acetonitrile 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 methylene chloride and chloroform
  • acetonitrile examples include acetonitrile.
  • 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
  • the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (1f) 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 (1g ′) can be isolated by performing a general post-treatment operation after the reaction.
  • the compound (1h) of the present invention can be produced by deprotecting the compound (1i) of the present invention.
  • 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.
  • the compound (1g) of the present invention can be produced by reacting the compound (1h) of the present invention with R b Lg 3 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, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • acetonitrile 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 methylene chloride and chloroform
  • acetonitrile examples include acetonitrile.
  • 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 (1h) of the present invention.
  • R b Lg 3 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 of the present invention (1 g) can be isolated by carrying out normal post-treatment operations after completion of the reaction.
  • this invention compound (1g) includes this invention compound (1g ').
  • R c1 may have one or more atoms or groups selected from ⁇ Group ⁇ >. Represents a C6 chain hydrocarbon group.
  • the compound (1j) of the present invention can be produced by reacting the compound (1f) 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, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • acetonitrile 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 methylene chloride and chloroform
  • acetonitrile examples include acetonitrile.
  • 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 (1f) 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 (1j) of the present invention can be isolated by performing ordinary post-treatment operations.
  • the present compound (1j) is further subjected to an oxidation reaction known to those skilled in the art to convert -SR c1 in the present compound (1j) to -S (O) z1 R c1 (in this case) , Z1 represents 1 or 2).
  • the compound (1l) of the present invention can be produced by reacting the compound (1k) of the present invention with R d Lg 3 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, halogenated hydrocarbons such as methylene chloride and chloroform, acetonitrile.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • acetonitrile 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 methylene chloride and chloroform
  • acetonitrile examples include acetonitrile.
  • 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 ratio of 1 mol to 2 mol with respect to 1 mol of the compound (1k) of the present invention.
  • R e Lg 3 is usually used in a proportion of 1 mol per 1 mol of the compound (1k) 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 (1l) can be isolated by carrying out ordinary post-treatment operations.
  • R d or R e is a primary or secondary alkyl group
  • the present compound (1k) or the present compound (1l) is reduced with an aldehyde or a ketone compound instead of the above method.
  • This invention compound (1l) or this invention compound (1m) can also be manufactured by making it react in 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 moles with respect to 1 mole of the compound (1k) or the compound (1l) 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 (1k) or the compound (1l) 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 (1l) or the compound of the present invention (1m) can be isolated by performing ordinary post-treatment operations.
  • the compound (1o) of the present invention can be produced by reacting the pyridine compound represented by the formula (1n) with an oxidizing agent.
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include halogenated hydrocarbons such as methylene chloride 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 (1n).
  • 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 (1o) of the present invention can be isolated by carrying out ordinary post-treatment operations.
  • the intermediate of the present invention can be produced, for example, by the following method.
  • Het is a group represented by the formula H4, and an intermediate (4a) of a compound in which Z 1 , Z 2 and Z 3 are —CE 1 ⁇ is produced, for example, according to the following scheme be able to.
  • Compound (4a) can be produced by reacting compound (15) with p-toluenesulfonyl isocyanide compound (16) in the presence of a base.
  • the reaction is usually carried out in the presence of a solvent.
  • a solvent such as ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, chlorides, and the like.
  • halogenated hydrocarbons such as methylene and chloroform, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Examples of the base used in the reaction include sodium hydride, sodium tert-butoxide, potassium tert-butoxide, 1,8-diazabicyclo [5,4,0] undec-7-ene, n-butyllithium and the like.
  • the base is usually used in a proportion of 1 mol to 10 mol with respect to compound (15).
  • the reaction can be performed in the presence of an additive (for example, a metal salt such as lithium bromide) as necessary.
  • an additive for example, a metal salt such as lithium bromide
  • the paratoluenesulfonyl isocyanide compound (16) is usually used at a ratio of 1 mole per 1 mole of the compound (15), but can be changed as appropriate.
  • the reaction temperature in the reaction of the compound (15) and the compound (16) is usually in the range of ⁇ 78 ° C. to 30 ° C., and the reaction time is in the range of 0.1 hour to 24 hours.
  • the compound (4a) can be isolated by performing a normal post-treatment operation.
  • R h represents a C1-C6 alkyl group, and R h may be the same or different.
  • Compound (19) can be produced by reacting compound (17) with compound (18).
  • 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 methylene chloride and chloroform, acetonitrile, and the like. Nitriles, N, N-dimethylformamide, acid amides such as N-methylpyrrolidinone, sulfoxides such as dimethylsulfoxide, and mixtures thereof. Moreover, it can also be made to react by using an acetal compound represented by Formula (18) in excess without using a solvent. The amount thereof to be used is generally in the range of 1.0 mol to 10 mol with respect to 1 mol of compound (17).
  • the reaction temperature in the reaction of the compound (17) and the compound (18) is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.
  • the compound (19) can be isolated by ordinary post-treatment operations.
  • 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 methylene chloride and chloroform, acetonitrile, and the like. Nitriles, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
  • Hydrazine is usually used in a ratio of 1 mol per 1 mol of compound (19), but can be changed as appropriate.
  • the reaction temperature in the reaction of the compound (19) with hydrazine is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.
  • the compound (4b) can be isolated by carrying out a normal post-treatment operation.
  • an intermediate (4c) of a compound in which Het is a group represented by the formula H4, Z 1 and Z 3 are —CE 1 ⁇ , and Z 2 is —N ⁇ is, for example, the following scheme Can be manufactured according to
  • Compound (4c) can be produced from compound (19) described in Intermediate Production Method 2 by the production method of compound (4b) or a method analogous thereto.
  • an intermediate (4e) of a compound in which Het is a group represented by the formula H4 and Z 1 , Z 2 and Z 3 are —N ⁇ can be produced, for example, according to the following scheme Can do.
  • Examples of the solvent used in the reaction include acetic acid.
  • the hydrazine compound is usually used at a ratio of 1 mole per 1 mole of the compound (22), but can be appropriately changed.
  • the reaction temperature in the reaction between the compound (22) and the hydrazine compound is usually in the range of 0 ° C. to the boiling point of the solvent, and the reaction time is in the range of 0.1 to 24 hours.
  • the compound (4e) can be isolated by 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 waiba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpas, etc .; (Leguminivora glycinivolora), Azusa yamashiga (Matsumuraeses
  • 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, polyethylene glycol fatty acid ester, and the like, and alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate.
  • nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and the like
  • alkyl sulfonate alkyl benzene sulfonate
  • alkyl sulfate alkyl sulfate.
  • An ionic surfactant is mentioned.
  • formulation adjuvants 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 (iso
  • 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, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10,000 ppm. Agents, powders, etc. 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, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 1000 ppm. Apply aerosols, smoke, poisonous bait, 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, plant growth regulators, herbicides and synergists are shown below.
  • Nereistoxin compounds Cartap, Bensulpap, Thiocylam, Thiosultap, Monosultap, and Bisultap.
  • Neonicotinoid compounds Imidacloprid (Imidac1oprid), Nitenpyram (Nitenpyram), Acetamiprid (Acetamiprid), Thiamethoxam (Thiamethoxam), Thiacloprid (An) and dinotefurin (in)
  • Benzoylurea compounds Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexafluuron, Hexafluuron Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron, and fluazuuron.
  • 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.
  • 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
  • Triazine herbicidal compounds Atrazine, Ametrine, Cyanazine, Simazine, Propazine, Simetrin, Dimetamethrin, Dimethamethrin ), Triaziflam, and indaziflam.
  • Carbamate herbicidal compound Di-allate, Tri-alate, EPTC, Butyrate, Benchiocarb, Esprocarb, Molinate, Dimepiperate, Dimepiperate (Swep), Chlorprofham, Phenmedifam, Phenisopham, Pyributicalb, and Asuram.
  • Chloroacetanilide herbicidal compounds Acetochlor, Alaclor, Butachlor, Dimethenamide, Propaclor, Metazachlor, Metolachlor, Metolachlor Pretilachor), tenylchlor (Theny1ch1or), and petoxamide (Pethoxamide).
  • 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.
  • Triketone herbicidal compounds Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefril trione.
  • Aryloxyphenoxypropionic acid herbicidal compound Clodinafop-propargyl, Cyhalofop-butyl, Diclohop-methyl, Fenoxaprop-ethyl Fluazifop-butyl, haloxyhop-methyl, quizalofop-ethyl, and metamihop.
  • Trione oxime herbicidal compounds Alloxydim-sodium, cetoxydim, Butroxidim, Crethodim, Cloproxidim, Cyclodimoxime (Tralkoxydim), and Profoxydim.
  • Sulfonamide herbicidal compounds Flumeslam, Methoslam, Diclosram, Floraslam, chloranthramx, Penoxsulox and Penoxsulox.
  • 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 ) —).
  • JLA group, (E 1 ) n , D, G and m represent the combinations described in the following [Table 2] to [Table 3].
  • Q represents the following formula.
  • the JLA group, (E 1 ) n , D, G and m represent the combinations described in the following [Table 4] to [Table 5].
  • the JL group, (E 1 ) p , D, G and m in the formula represent the combinations described in the following [Table 6] to [Table 7].
  • the JL group, (E 1 ) n , D, G and m in the formula represent the combinations described in the following [Table 8] to [Table 12].
  • the JL group, E 1 , D, G and m in the formula represent the combinations described in the following [Table 13] to [Table 14].
  • the JLA group, (E 1 ) n , D, G and m represent the combinations described in the following [Table 15] to [Table 18].
  • JLA group, E 1 , D, G and m represent the combinations described in the following [Table 19] to [Table 20].
  • a part represents a weight part.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide-containing fine powder and 54 parts of diatomaceous earth were mixed, and the above-mentioned compounds 1-1 to 1-51, compounds 2-1 to 2-34, Any one of Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6-1 to 6-102, and Compounds 7-1 to 7-34 20 Add parts and mix to obtain each wettable powder.
  • Formulation Example 3 Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- Add 1 part of synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay to 2 parts of any one of 1 to 6-102 and compounds 7-1 to 7-34 To do. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
  • Formulation Example 4 Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- One part of any one of 1 to 6-102 and compounds 7-1 to 7-34 is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide-containing fine powder, 0.3 part of PAP and 93.7 of Fusami clay 93.7 are mixed. Add parts, mix well, and evaporate and remove acetone to obtain each powder.
  • 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 1-51, compounds 2-1 to 2-34, compounds 3-1 to 3 -38, compounds 4-1 to 4-104, compounds 5-1 to 5-38, compounds 6-1 to 6-102, and compounds 7-1 to 7-34 10 parts and water 55 parts Are mixed and finely pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 7 Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 10 mg of any one of 1 to 6-102 and compounds 7-1 to 7-34 is dissolved in 0.5 ml of acetone, and this solution is mixed with animal solid feed powder (bred breeding solid feed powder CE-2, Japan Treat to 5g, and mix evenly. Then, acetone is evaporated to dryness to obtain each poisonous bait.
  • animal solid feed powder termed breeding solid feed powder CE-2, Japan Treat to 5g, and mix evenly.
  • acetone is evaporated to dryness to obtain each poisonous bait.
  • Formulation Example 8 Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 0.1 part of any one of 1 to 6-102 and compounds 7-1 to 7-34 and 49.9 parts of neothiozole (Chuo Kasei Co., Ltd.) were placed in an aerosol can and fitted with an aerosol valve.
  • the oil agent aerosol is obtained by filling the part and 25 parts of LPG, adding shaking, and mounting the actuator.
  • Formulation Example 9 Compounds 1-1 to 1-51, Compounds 2-1 to 2-34, Compounds 3-1 to 3-38, Compounds 4-1 to 4-104, Compounds 5-1 to 5-38, Compounds 6- 0.6 part of any one of 1 to 6-102 and compounds 7-1 to 7-34, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, Deodorized kerosene 3.39 parts and emulsifier ⁇ Atmos 300 (registered trademark name of Atmos Chemical Co., Ltd.) ⁇ 1 part mixed and dissolved, and distilled water 50 parts are filled in an aerosol container, and after attaching the valve, Aqueous aerosol is obtained by pressure filling 40 parts of propellant (LPG).
  • LPG propellant
  • Test example 1 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Test example 2 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test 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

La présente invention concerne un nouveau composé possédant une activité antiparasitaire. La présente invention concerne un composé cyclique hétéroaromatique représenté par la formule (1) [Dans la formule, Het représente un hétérocycle de 5 éléments représenté par une formule H1, H2, H3, H4 ou H5 (Dans la formule, Y1, Y2, Y3, Z1, Z2 et Z3 ont la signification décrite dans les revendications de la présente demande, et la marque « · » à gauche de la formule développée représente une position qui se lie à A.) ; J représente un groupe t-butyle, un groupe triméthylsilyle, ou analogue ; L représente une liaison simple ou un groupe alkylène en C1-C3 ; A représente une liaison simple ou analogue ; G représente un atome d'hydrogène, un atome d'halogène ou analogue ; D représente -N= ou -CH= ; et m représente 0 ou 1.], un procédé de production de celui-ci, et un agent antiparasitaire contenant le composé cyclique hétéroaromatique.
PCT/JP2011/077640 2010-12-01 2011-11-30 Composé cyclique hétéroaromatique et son application antiparasitaire WO2012073995A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017104741A1 (fr) * 2015-12-16 2017-06-22 日本曹達株式会社 Composé de type arylazole et agent de lutte contre les organismes nuisibles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112016022451B1 (pt) * 2014-04-24 2021-03-30 Sumitomo Chemical Company, Limited Composto de diaril-azol e agente de controle de peste artrópoda

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63290870A (ja) * 1987-05-25 1988-11-28 Sumitomo Chem Co Ltd １，２，４−トリアゾ−ル誘導体、その製造法およびそれを有効成分とする殺虫剤
US4826867A (en) * 1986-08-26 1989-05-02 Bayer Aktiengesellschaft Substituted 1-aryl-3-tert.-butyl-pyrazoles
EP0400842A1 (fr) * 1989-05-18 1990-12-05 Schering Agrochemicals Limited Triazoles comme pesticides
US5064844A (en) * 1988-07-08 1991-11-12 Schering Agrochemicals Limited 1,2,3-triazole insecticides
WO1995000506A1 (fr) * 1993-06-24 1995-01-05 Bayer Aktiengesellschaft Pyridylpyrroles substitues et leur utilisation pour combattre des animaux parasites
WO1999006380A1 (fr) * 1997-08-01 1999-02-11 Nissan Chemical Industries, Ltd. Composes de tetrazole et agent de controle des parasites
WO2002068413A1 (fr) * 2001-02-22 2002-09-06 Bayer Cropscience Ag Pyrazolylpyrimidines
JP2009073776A (ja) * 2007-09-21 2009-04-09 Sumitomo Chemical Co Ltd 複素環化合物およびその有害節足動物防除剤
WO2010064688A1 (fr) * 2008-12-03 2010-06-10 日本農薬株式会社 Dérivés pyrimidines, insecticides pour cultures maraîchères comportant de tels dérivés et leur procédé d’utilisation
WO2010119879A1 (fr) * 2009-04-16 2010-10-21 Sumitomo Chemical Company, Limited Composé de pyrimidine et son utilisation pour la lutte antiparasitaire
WO2011042389A2 (fr) * 2009-10-09 2011-04-14 Bayer Cropscience Ag Phenylpyri(mi)dinylazoles

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4826867A (en) * 1986-08-26 1989-05-02 Bayer Aktiengesellschaft Substituted 1-aryl-3-tert.-butyl-pyrazoles
JPS63290870A (ja) * 1987-05-25 1988-11-28 Sumitomo Chem Co Ltd １，２，４−トリアゾ−ル誘導体、その製造法およびそれを有効成分とする殺虫剤
US5064844A (en) * 1988-07-08 1991-11-12 Schering Agrochemicals Limited 1,2,3-triazole insecticides
EP0400842A1 (fr) * 1989-05-18 1990-12-05 Schering Agrochemicals Limited Triazoles comme pesticides
WO1995000506A1 (fr) * 1993-06-24 1995-01-05 Bayer Aktiengesellschaft Pyridylpyrroles substitues et leur utilisation pour combattre des animaux parasites
WO1999006380A1 (fr) * 1997-08-01 1999-02-11 Nissan Chemical Industries, Ltd. Composes de tetrazole et agent de controle des parasites
WO2002068413A1 (fr) * 2001-02-22 2002-09-06 Bayer Cropscience Ag Pyrazolylpyrimidines
JP2009073776A (ja) * 2007-09-21 2009-04-09 Sumitomo Chemical Co Ltd 複素環化合物およびその有害節足動物防除剤
WO2010064688A1 (fr) * 2008-12-03 2010-06-10 日本農薬株式会社 Dérivés pyrimidines, insecticides pour cultures maraîchères comportant de tels dérivés et leur procédé d’utilisation
WO2010119879A1 (fr) * 2009-04-16 2010-10-21 Sumitomo Chemical Company, Limited Composé de pyrimidine et son utilisation pour la lutte antiparasitaire
WO2011042389A2 (fr) * 2009-10-09 2011-04-14 Bayer Cropscience Ag Phenylpyri(mi)dinylazoles

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017104741A1 (fr) * 2015-12-16 2017-06-22 日本曹達株式会社 Composé de type arylazole et agent de lutte contre les organismes nuisibles
CN108430976A (zh) * 2015-12-16 2018-08-21 日本曹达株式会社 芳基唑化合物和有害生物防除剂
KR20180095813A (ko) * 2015-12-16 2018-08-28 닛뽕소다 가부시키가이샤 아릴아졸 화합물 및 유해 생물 방제제
JPWO2017104741A1 (ja) * 2015-12-16 2018-10-04 日本曹達株式会社 アリールアゾール化合物および有害生物防除剤
JP2021020923A (ja) * 2015-12-16 2021-02-18 日本曹達株式会社 アリールアゾール化合物および有害生物防除剤
KR102282807B1 (ko) * 2015-12-16 2021-07-27 닛뽕소다 가부시키가이샤 아릴아졸 화합물 및 유해 생물 방제제
KR20210094161A (ko) * 2015-12-16 2021-07-28 닛뽕소다 가부시키가이샤 아릴아졸 화합물 및 유해 생물 방제제
US11180456B2 (en) 2015-12-16 2021-11-23 Nippon Soda Co., Ltd. Arylazole compound and pest control agent
KR102352912B1 (ko) 2015-12-16 2022-01-18 닛뽕소다 가부시키가이샤 아릴아졸 화합물 및 유해 생물 방제제
CN108430976B (zh) * 2015-12-16 2022-07-05 日本曹达株式会社 芳基唑化合物和有害生物防除剂
US11884633B2 (en) 2015-12-16 2024-01-30 Nippon Soda Co., Ltd. Arylazole compound and pest control agent

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