WO2012050141A1 - Composé à noyau hétéroaromatique et son utilisation pour la lutte contre les organismes nuisibles - Google Patents

Composé à noyau hétéroaromatique et son utilisation pour la lutte contre les organismes nuisibles Download PDF

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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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English (en)
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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    • 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

La présente invention concerne un nouveau composé qui a une activité de lutte contre les organismes nuisibles. La présente invention concerne : un composé à noyau hétéroaromatique qui est représenté par la formule (1); un procédé de production du composé à noyau hétéroaromatique; et un agent de lutte contre les organismes nuisibles qui contient le composé à noyau hétéroaromatique. (Dans la formule, Het représente un noyau hétéroaromatique à cinq chaînons ou six chaînons qui contient un ou plusieurs atomes choisis dans le groupe consistant en un atome d'azote, un atome d'oxygène ou un atome de soufre; J représente un groupe tert-butyle ou similaire; L représente une simple liaison, un groupe alkylène en C1-C3 ou similaire; A représente une simple liaison ou similaire; Q représente un groupe méthylène ou similaire; G représente un atome d'hydrogène, un atome d'halogène ou similaire; D représente -N= ou -CH=; et m représente 0 ou 1).
PCT/JP2011/073451 2010-10-14 2011-10-12 Composé à noyau hétéroaromatique et son utilisation pour la lutte contre les organismes nuisibles WO2012050141A1 (fr)

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US20220081417A1 (en) * 2020-09-16 2022-03-17 Nura Bio, Inc. Substituted pyridine derivatives as sarm1 inhibitors
WO2022255465A1 (fr) * 2021-06-02 2022-12-08 日本農薬株式会社 Composé de benzimidazole ou sel associé, insecticide/acaricide agricole et horticole et agent de lutte contre la filariose canine pour animaux le contenant, et son procédé d'utilisation
US11629136B1 (en) 2021-07-28 2023-04-18 Nura Bio, Inc. Substituted pyridine derivatives as SARM1 inhibitors
US11970481B1 (en) 2020-08-04 2024-04-30 Nura Bio, Inc. Substituted pyridine derivatives as SARM1 inhibitors

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11970481B1 (en) 2020-08-04 2024-04-30 Nura Bio, Inc. Substituted pyridine derivatives as SARM1 inhibitors
US20220081417A1 (en) * 2020-09-16 2022-03-17 Nura Bio, Inc. Substituted pyridine derivatives as sarm1 inhibitors
US11945796B2 (en) * 2020-09-16 2024-04-02 Nura Bio, Inc. Substituted pyridine derivatives as SARM1 inhibitors
WO2022255465A1 (fr) * 2021-06-02 2022-12-08 日本農薬株式会社 Composé de benzimidazole ou sel associé, insecticide/acaricide agricole et horticole et agent de lutte contre la filariose canine pour animaux le contenant, et son procédé d'utilisation
US11629136B1 (en) 2021-07-28 2023-04-18 Nura Bio, Inc. Substituted pyridine derivatives as SARM1 inhibitors

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