WO2012102387A1 - Dérivé de pyrazole et pesticide - Google Patents

Dérivé de pyrazole et pesticide Download PDF

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Publication number
WO2012102387A1
WO2012102387A1 PCT/JP2012/051847 JP2012051847W WO2012102387A1 WO 2012102387 A1 WO2012102387 A1 WO 2012102387A1 JP 2012051847 W JP2012051847 W JP 2012051847W WO 2012102387 A1 WO2012102387 A1 WO 2012102387A1
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group
optionally substituted
alkyl
substituted
phenyl
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PCT/JP2012/051847
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Japanese (ja)
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沼田　昭
陽子 伊與部
光貴 富澤
公則 安藤
裕貴 古川
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日産化学工業株式会社
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Priority to JP2012554869A priority Critical patent/JPWO2012102387A1/ja
Publication of WO2012102387A1 publication Critical patent/WO2012102387A1/fr

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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
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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Definitions

  • R 7 represents a hydrogen atom or R 6a
  • R 8 and R 8a are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 14 , C 3 -C 8 cycloalkyl, R 14 optionally substituted (C 3 ⁇ C 8) cycloalkyl, C 2 ⁇ C 6 alkenyl, optionally substituted with R 14 (C 2 ⁇ C 6 ) alkenyl, C 3 ⁇ C 8 cycloalkenyl in, R 14 optionally substituted (C 3 ⁇ C 8) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally substituted with R 14 (C 2 ⁇ C 6 ) alkynyl, -S (O) 2 R 11a in, - C (O) R 12 , —N (R 13a ) R 13 , —C (O) OR 11a , —C (O)
  • R 12 represents a hydrogen atom or R 11a
  • R 13 and R 13a are each independently a hydrogen atom, cyano, C 1 ⁇ C 6 alkyl, optionally substituted with R 14a (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, in R 14a optionally substituted (C 2 ⁇ C 6) alkenyl, C 2 ⁇ C 6 alkynyl, optionally substituted with R 14a (C 2 ⁇ C 6 ) alkynyl, C 3 ⁇ C 8 cycloalkyl, optionally R 14a been (C 3 ⁇ C 8) cycloalkyl substituted, C 3 ⁇ C 8 cycloalkenyl, optionally substituted with R 14a (C 3 ⁇ C 8 ) cycloalkenyl, phenyl, naphthyl, with (Z 2) q2 Substituted phenyl, (Z 2 ) q2 substituted naphthyl, D2-1 to D
  • Alkyl group C 1 -C 6 alkoxy group, —CHO group, C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 haloalkoxycarbonyl group, C 1 -C 6 alkylaminocarbonyl group, C 1 -C 6 halo alkylaminocarbonyl group, a phenyl group, (Z 2) phenyl group substituted by q2, optionally substituted with D2-1 ⁇ D2-102, oxo group or thioxo group It may be,
  • R 13b is a hydrogen atom, cyano, substituted nitro, C 1 ⁇ C 6 alkyl, optionally substituted with R 14a (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, optionally with R 14a (C 2 ⁇ C 6) alkenyl, substituted C 2 ⁇ C 6 alkynyl, optionally substituted with R 14a (C 2 ⁇ C 6 ) alkynyl, C 3 ⁇ C 8 cycloalkyl, optionally with R 14a ( C 3 -C 8 ) cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 14a , —S (O) r R 15 , —C (O) R 16 , —C (O) OR 15a , —C (O) N (R 17a ) R 17 , —C (S) N (R 17a
  • the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, or a C 1 -C 6 alkylthio group.
  • R 24 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28 , optionally substituted with R 28 (C 2 ⁇ C 6 ) alkenyl, optionally substituted with R 28 (C 2 ⁇ C 6 ) alkynyl, optionally substituted with R 28 (C 3 ⁇ C 8 ) cycloalkyl Alkyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 28 , —OR 25 , —S (O) r R 25 , —C (O) OR 25 , —C (O) R 26 , — N (R 27a ) R 27 , -C (O) N (R 27a ) R 27 , -C (S) N (R 27a ) R 27 , -S (O
  • X 1 is a halogen atom, cyano, nitro, azide, —SCN, —SF 5 , C 1 -C 12 alkyl, (C 1 -C 12 ) alkyl optionally substituted with R 5 , C 3 -C 12 cyclo alkyl, optionally substituted with R 5 (C 3 ⁇ C 12 ) cycloalkyl, substituted C 2 ⁇ C 12 alkenyl, optionally with R 5 (C 2 ⁇ C 12 ) alkenyl, C 3 ⁇ C 12 cycloalkyl alkenyl, optionally substituted with R 5 (C 3 ⁇ C 12 ) cycloalkenyl, substituted C 2 ⁇ C 12 alkynyl, optionally with R 5 (C 2 ⁇ C 12 ) alkynyl, C 3 ⁇ C 12 allenyl , —OH, —OR 6 , —SH, —S (O) r R 6 , —S ( ⁇ NR 8b )
  • a 2 is D1-6, D1-7, D1-15 to D1-17, D1-25 to D1-27, D1-39, D1-40, D1-42, D1-44, D1-45 D1-47, D1-69, D1-73, D1-77, D1-78, D1-80, D1-81, D1-86, D1-87, D1-90 or D1-93, and p1,
  • p2, p3, p4 or p5 represents an integer of 1 or more
  • X 1 is a halogen atom, cyano, nitro, azide, —SCN, —SF 5 , C 1 -C 12 alkyl, (C 1 -C 12 ) alkyl optionally substituted with R 5 , C 3 -C 12 cyclo alkyl, optionally substituted with R 5 (C 3 ⁇ C 12 ) cycloalkyl, substituted C 2 ⁇ C 12 alkenyl, optionally with R 5 (C 2 ⁇ C 12 ) alkenyl, C 3 ⁇ C 12 cycloalkyl alkenyl, optionally substituted with R 5 (C 3 ⁇ C 12 ) cycloalkenyl, substituted C 2 ⁇ C 12 alkynyl, optionally with R 5 (C 2 ⁇ C 12 ) alkynyl, C 3 ⁇ C 12 allenyl , —OH, —OR 6 , —SH, —S (O) r R 6 , —S ( ⁇ NR 8b )
  • the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with a halogen atom, a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group.
  • X 1 forms a methylene chain together with R 3 to form a 5-membered ring together with the carbon atom to which X 1 is bonded, the carbon atom to which R 3 is bonded and the carbon atom to which A 2 is bonded.
  • the methylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and further contains a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 1 to C 6 alkylthio group, C 1 to C 6 haloalkylthio group, —NH 2 group, C 1 to C 6 alkylamino group, di (C 1 ⁇ C 6) alkylamino group, phenyl, naphthyl, (Z 2) phenyl substituted with q2, (Z 2) q2 that is substituted with naphthyl or D2-1 ⁇ D2-102, oxo group, thioxo group, an imino Group, Optionally substituted by a C 1 -C 6 alkylimino group or a
  • the alkylene chain or alkenylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and further, a halogen atom, a cyano group, a nitro group C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group , -NH 2 group, C 1 ⁇ C 6 alkylamino group, di (C 1 ⁇ C 6) alkylamino group, phenyl, naphthyl, phenyl substituted with (Z 2) q2, substituted with (Z 2) q2
  • the alkylene chain or alkenylene chain is , An oxygen atom, a sulfur atom or a nitrogen atom, and a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, C 1 ⁇ C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, -NH 2 group, C 1 -C 6 alkylamino group, di (C 1 -C 6 ) alkylamino group, phenyl, naphthyl, (Z 2 ) q2 Phenyl substituted with (Z 2 ) q2 substituted with naphthyl or D2-1 to D2-102, oxo group, thioxo group, imino group, C 1 -C 6 alkylim
  • R 1 and R 4 represent a hydrogen atom
  • B represents a ring represented by any one of B-1a, B-2a, B-2b, B-3a to B-5a;
  • B represents a ring represented by any of B-1a, B-2b, and B-3a;
  • a 3 represents —C (X 1b ) X 1c — X 1b and X 1c represent a hydrogen atom,
  • X 1 represents D2-37,
  • X 1a represents a hydrogen atom, C 1 -C 12 alkyl or (C 1 -C 12 ) alkyl optionally substituted with R 5 ,
  • R 5 represents a halogen atom, cyano, —OR 11 or —S (O) r R 11 ,
  • R 11 represents C 1 -C 6 alkyl,
  • R 1 and R 4 represent a hydrogen atom
  • a 2 represents D1-14, D1-31, D1-34, D1-35, D1-52, D1-57 or D1-68, and p1, p3, p4 or p8 represents an integer of 1.
  • the seed treatment agent according to the above [18], wherein the seed treatment method is immersion treatment.
  • the compounds encompassed by the present invention may have geometrical isomers of E-forms and Z-forms depending on the type of substituents. And a mixture containing the Z-form in an arbitrary ratio.
  • the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.
  • n- means normal
  • i- means iso
  • s- means secondary and tert- means tertiary
  • Ph means phenyl
  • C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule.
  • Represents a saturated hydrocarbon group for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1
  • Specific examples include 1,2-dimethyl-2-propenyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b haloalkenyl is represented by a linear or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms.
  • a monocyclic or complex ring structure from a member ring to a 6-member ring can be formed.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form.
  • Specific examples include 1-cyclopenten-1-yl group, 2-cyclopenten-1-yl group, 1-cyclohexen-1-yl group, 2-cyclohexen-1-yl group, and the like. Selected in a range of numbers.
  • C a -C b halocycloalkenyl has the following meaning: a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, a cyclic one having 1 to b carbon atoms, and one Alternatively, it represents an unsaturated hydrocarbon group having two or more double bonds, and can form a monocyclic or complex ring structure having 3 to 6 members. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form.
  • C a -C b haloalkynyl represents a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • an unsaturated hydrocarbon group having one or more triple bonds in the molecule.
  • the halogen atoms when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other.
  • Specific examples include 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group and the like. Each of which is selected for each specified number of carbon atoms.
  • C a -C b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1 Specific examples include 1,2,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylamino group , Ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, tert-butylamino group and the like. Selected by range.
  • di (C a -C b alkyl) amino in the present specification has the above-mentioned meaning that the number of carbon atoms which may be both the same or different from each other is ab.
  • Represents an amino group substituted by an alkyl group for example, dimethylamino group, ethyl (methyl) amino group, diethylamino group, n-propyl (methyl) amino group, i-propyl (methyl) amino group, di (n-propyl)
  • Specific examples include an amino group, a di (n-butyl) amino group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • Specific examples include an oxyimino group, an i-propyloxyimino group, an n-butyloxyimino group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning comprising a to b carbon atoms, for example, an acetyl group, a propionyl group, a butyryl group.
  • Specific examples thereof include isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like, and each is selected in the range of the designated number of carbon atoms.
  • C a -C b haloalkylcarbonyl in the present specification represents a haloalkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as a fluoroacetyl group, a chloroacetyl group, Difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylpropanoyl group Etc.
  • a fluoroacetyl group such as a fluoroacetyl group, a chloroacetyl group, Difluoroacetyl group, dichloroacetyl group, trifluoroacety
  • Famoyl group ethylsulfamoyl group, n-propylsulfamoyl group, i-propylsulfamoyl group, n-butylsulfamoyl group, i-butylsulfamoyl group, s-butylsulfamoyl group, Specific examples include a tert-butylsulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenylsulfinyl represents an alkenyl-S (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, and ranges of each designated number of carbon atoms. Selected.
  • Optionally substituted by R 5 in this specification (C a ⁇ C b) cycloalkyl, optionally substituted by R 5a (C a ⁇ C b ) cycloalkyl, optionally substituted by R 14 (C a ⁇ C b) cycloalkyl, substituted optionally substituted by R 14a (C a ⁇ C b ) cycloalkyl, optionally substituted by R 18 (C a ⁇ C b ) cycloalkyl, optionally by R 19 been (C a ⁇ C b) cycloalkyl, notation (C a ⁇ C b) cycloalkyl such as optionally substituted by optionally substituted (C a ⁇ C b) cycloalkyl or R 28 by R 23 can be any R 5, R 5a, R 14 , R 14a, by R 18, R 19, R 23 or R 28, an optionally substituted hydrogen atoms bonded to carbon atoms Cycloalkyl group having
  • Optionally substituted by R 5 in this specification (C a ⁇ C b) cycloalkenyl, optionally substituted by R 5a (C a ⁇ C b ) cycloalkenyl, optionally substituted by R 14 (C a -C b ) cycloalkenyl, optionally substituted by R 14a (C a -C b ) cycloalkenyl, optionally substituted by R 18 (C a -C b ) cycloalkenyl, optionally substituted by R 19 been (C a ⁇ C b) notation such as (C a ⁇ C b) cycloalkenyl optionally substituted by optionally substituted (C a ⁇ C b) cycloalkenyl or R 28 by a cycloalkenyl or R 23 can be any R 5, R 5a, R 14 , R 14a, by R 18, R 19, R 23 or R 28, hydrogen atoms bonded to carbon atoms Number
  • the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.
  • R 17 represents that, together with R 17a , a C 2 to C 7 alkylene chain is formed to form a 3- to 8-membered ring together with the nitrogen atom to which R 17 and R 17a are bonded.
  • the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.
  • the notation include, for example, aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine, thiazolidine-2-one, thiazolidine -2-thione, imidazolidine, imidazolidine-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1, 3-Oxazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazine- 2-one, 2H-3,4,5,
  • [R 8c and R 8d are combined to form a C 4 to C 6 alkylene chain or a C 4 to C 6 alkenylene chain, thereby forming 5 to 7 together with the carbon atom to which R 8c and R 8d are bonded.
  • a member ring may be formed, and the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.
  • Specific examples of such notations include thiazolidine-2-ylidene, 2,3-dihydrothiazol-2-ylidene, imidazolidine-2-ylidene, 2,3-dihydroimidazol-2-ylidene, 2,3-dihydro- 1,3,4-thiadiazole-2-ylidene, 1,2-dihydropyridine-2-ylidene, 2,3-dihydropyridazine-3-ylidene, 1,2-dihydropyrazin-2-ylidene, 1,2-dihydropyrimidine -2-ylidene, 6H-2,3-dihydro-1,3,4-thiadiazine-2-ylidene, and the like, and are selected in the range of the specified number of atoms.
  • [R 8e and R 8f are combined to form a C 4 to C 6 alkylene chain or a C 4 to C 6 alkenylene chain, thereby forming a 5 to 7 together with a sulfur atom to which R 8e and R 8f are bonded.
  • a member ring may be formed, and the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.
  • Specific examples of the notation include tetrahydrothiophene, tetrahydrothiophenone, tetrahydrothiopyran, thiopyran-4-one, 1,4-thioxan, and the like, and each is selected within the specified number of atoms.
  • X 1 II optionally substituted with R 5 (C 1 ⁇ C 6 ) alkyl [wherein, R 5 represents -S (O) r R 11, R 11 is C 1 ⁇ C 6 alkyl or C 1 Represents a C 6 haloalkyl, and r represents an integer of 0 to 2. ].
  • X 1 III optionally substituted with R 5 (C 1 ⁇ C 6 ) alkyl [wherein, R 5 represents a halogen atom. ].
  • X 1 IV D2-37.
  • examples of the range of the substituent represented by X 1a include the following groups.
  • X 1a II optionally substituted with R 5a (C 1 ⁇ C 6 ) alkyl [wherein, R 5a represents -S (O) r R 11, R 11 is C 1 ⁇ C 6 alkyl or C 1 Represents a C 6 haloalkyl, and r represents an integer of 0 to 2. ].
  • X 1a III optionally substituted with R 5a (C 1 ⁇ C 6 ) alkyl [wherein, R 5a represents a halogen atom. ].
  • examples of the range of the substituent represented by B include the following groups.
  • BI B-1 to B-6 [wherein A 3 represents —O—, —S (O) r —, —C (X 1b ) X 1c —, wherein X 1b and X 1c are each independently represents a hydrogen atom or a C 1 ⁇ C 6 alkyl Te, X 1d and X 1f is a hydrogen atom, n represents an integer 1, r is an integer of 0-2. ].
  • BIII B-3, B-6 [wherein A 3 represents —O—, —S (O) r —, —C (X 1b ) X 1c —, wherein X 1b and X 1c are each independently Represents a hydrogen atom or C 1 -C 6 alkyl, X 1d and X 1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].
  • BIV B-1 and B-3 [wherein A 3 represents —O—, —S (O) r —, —C (X 1b ) X 1c —, wherein X 1b and X 1c are each independently Represents a hydrogen atom or C 1 -C 6 alkyl, X 1d and X 1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].
  • B-1 [wherein A 3 represents —C (X 1b ) X 1c —, X 1b and X 1c each independently represent a hydrogen atom or C 1 -C 6 alkyl, and X 1d and X 1f represents a hydrogen atom, and n represents an integer of 1. ].
  • BVI: B-3 [wherein A 3 represents —C (X 1b ) X 1c —, X 1b and X 1c each independently represent a hydrogen atom or C 1 -C 6 alkyl, and X 1d and X 1f represents a hydrogen atom, n represents represents an integer of 1. ].
  • BVII B-4 [wherein A 3 represents —CH 2 —, and n represents an integer of 1.
  • BVIII B-1 [wherein A 3 represents —O—, X 1d and X 1f represent a hydrogen atom, and n represents an integer of 1. ].
  • BIX B-3 [wherein A 3 represents —O—, X 1d and X 1f represent a hydrogen atom, and n represents an integer of 1. ].
  • BX B-1 [wherein A 3 represents —S (O) r —, X 1d and X 1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2] . ].
  • BXI B-3 [wherein A 3 represents —S (O) r —, X 1d and X 1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].
  • each group which shows the range of each substituent in these compounds included in the present invention can be arbitrarily combined, and each represents the range of the present compound.
  • Examples of combinations of R 3 , A 2 , X 1 and X 1a include, for example, combinations shown in Table 1 below.
  • Examples of combinations of R 3 , B, X 1 and X 1a include the combinations shown in Table 2 below.
  • the combinations of Tables 1 and 2 are for illustrative purposes, and the present invention is not limited to these.
  • an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.
  • This reaction can be carried out without solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • an acid such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or Mitsunobu reaction using diethyl azodicarboxylate and triphenylphosphine or the like can be used.
  • the compound represented by the general formula (2-1) and the known general formula (6) [wherein X 1a represents the same meaning as described above.
  • the compound of the present invention represented by general formula (3) and general formula (4) can also be synthesized by reacting the compound represented by general formula (3).
  • the compound represented by the general formula (6) can be used in the range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by the general formula (2-1).
  • an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.
  • This reaction can be carried out without solvent, but a solvent may be used.
  • a solvent for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.
  • This reaction can be carried out without solvent, and a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • the amount of the compound represented by the general formula (11) can be used in the range of 0.8 to 5 equivalents relative to 1 equivalent of the compound represented by the general formula (10).
  • Some of the compounds represented by the general formula (11) used here are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to the methods described in the literature.
  • Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, copper acetate (monovalent).
  • the amount of the base used can be in the range of 0.1 to 10.0 equivalents relative to 1 equivalent of the compound represented by the general formula (10).
  • This reaction can be carried out without solvent, but a solvent may be used.
  • a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • the catalyst is used in an amount of 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 1 equivalent to 1 equivalent of the compound represented by the general formula (12).
  • the range is 0.2 equivalent.
  • the base to be used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate.
  • the amount of the base used is in the range of 0.1 to 10.0 equivalents with respect to 1 equivalent of the compound represented by the general formula (12). This reaction can be carried out without solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from 0 ° C. to the reflux temperature of the solvent to be used, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.
  • This reaction can be carried out without solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • an acid such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or Mitsunobu reaction using diethyl azodicarboxylate and triphenylphosphine or the like can be used.
  • this invention compound represented by General formula (22) and General formula (23) by making the compound represented by General formula (20) and the compound represented by well-known General formula (6) react. Can also be synthesized.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • the general formula (24) [wherein A 1 , A 3 , R 2 , R 4 , X 1 , n and n1 have the same meaning as described above.
  • This invention compound represented by this can be synthesize
  • the compound represented by the general formula (7) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the general formula (20).
  • an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • R 3 , R 4 and X 1 represent the same meaning as described above.
  • the compound represented by the general formula (16) [wherein A 1 , R 2 and n1 represent the same meaning as described above, and L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, —B (OH ) 2 groups or —B (OR 50 ) 2 groups (wherein R 50 represents the same or different C 1 to C 6 alkyl, or two G together represent —CH 2 CH 2 — Or -C (CH 3 ) 2 C (CH 3 ) 2- may be formed).
  • Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, copper acetate (monovalent). ), Copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide and the like.
  • the amount of the catalyst used is 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 0, relative to 1 equivalent of the compound represented by the general formula (30). It can be used in the range of 2 equivalents.
  • Examples of the base used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. .
  • the amount of the base used can be in the range of 0.1 to 10.0 equivalents relative to 1 equivalent of the compound represented by the general formula (30). This reaction can be carried out without a solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
  • the compound represented by the general formula (2-1) used in the production method A can be synthesized, for example, as follows.
  • Reaction formula 1 General formula (14) [wherein R 3 and R 4 represent the same meaning as described above. ] Can be synthesized by a known method such as Journal Heterocyclic Chemistry 1986, 23, 275. That is, the compound represented by the general formula (14) is converted into a known general formula (14) according to a known method known from the literature, for example, the method described in Journal of Organic Chemistry 2004, 69, 5578.
  • the compound represented by the general formula (12) used in the production method C can be synthesized, for example, as follows.
  • Reaction formula 2 The general formula (17) [wherein A 1, R 2, R 3 , R 4, J b and n1 represent the same meanings as described above. ] Can be synthesized by known methods such as Journal Heterocyclic Chemistry 1981, Vol. 18, p. 9. That is, the compound represented by the general formula (17) is converted into B (OR 50 ) according to a known method known in the literature, for example, the method described in Journal of Heterocyclic Chemistry 2004, 41, 931.
  • the compound represented by General Formula (20) used in Production Method D can be synthesized, for example, as follows.
  • Reaction formula 3 General formula (18) [wherein A 3 and R 4 represent the same meaning as described above, and n represents an integer of 0 to 3. ]
  • the compound represented by the general formula (18) is reacted with the compound represented by the known general formula (16) similarly to the above reaction formula 1 in the presence of a transition metal catalyst such as palladium and a base.
  • a transition metal catalyst such as palladium and a base.
  • the compound represented by the general formula (35) is reacted with N, N′-dimethylformamide dimethyl acetal (DMFDMA) according to a known method known in the literature, thereby obtaining a compound represented by the general formula (36) [in the formula A 3 , R 4 , n and EE represent the same meaning as described above. ] Can be easily produced.
  • the general formula (37) [wherein A 3 , R 4 , n and EE represent the same meaning as described above. ]
  • the general formula (38) [wherein A 3 , R 4 , X 1a , n and EE represent the same meaning as described above.
  • D2-7a, D2-32a, D2-32b, D2-33a, D2-34a, D2-34b, D2-37a, D2-37b, D2-81a, D2-82a, D2-108a and D2 -108b represents the following structural formulas, D2-32b and numbers written in each structural formula D2-37b represents the substitution position of X 2, numbers written in the structural formula of D2-108b is Z 2 is represented.
  • the compounds of the present invention are stored in warehouses, so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, so-called sanitary pests that cause various adverse effects in human living environments such as houses.
  • Insects as so-called stored grain pests that harm cereals and the like, and mites, crustaceans, molluscs, nematodes that occur and harm in similar situations can be effectively controlled at low concentrations.
  • Specific examples of insects, ticks, crustaceans, mollusks and nematodes that can be controlled using the compounds of the present invention include the following organisms, but the present invention is not limited to these. is not.
  • Hirazuhanaazamiuma (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), yellow tea thrips (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci), Kakikudaazamiuma (Ponticulothrips diospyrosi) etc. Moths in total.
  • Soybean flies (Asphondylia yushimai), mud wings (Sitodiplosis Clam fly, Agromyza oryzae, Chromatomyia (Pegomya cunicularia), Apple Maggot (Rhagoletis pomonella), Hessian Fly (Mayetiola destructor), Housefly (Musca domestica), Bumbleflies (Stomoxys calcitrans), Sheep Flies (Melophagus ovinus), Bullflies (vis) D (Hypoderma lineatum), sheep flies (Oestrus ⁇ ovis), tsetse flies (Glossina palpalis, Glossina morsitans), yellowtail (Prosimulium yezoensis), cattle fly (Tabanus trigonus), pallens), Aedes aegypti, Aedes albopicutus, Anopheles hyracanus sinesis, etc
  • Bumblebee (Apethymus kuri), Bumblebee (Athalia rosae), Bumblebee (Arge pagana), Bumblebee (Neodiprion sertifer), Bumblebee (Dryocosmus kuriphilus), Gantai (Eciton burchelli, Eciton schmitus), Eciton burchelli, Eciton schmitus Mammalia insects such as mandarina, bulldog ant (Myrmecia spp.), fire ant (Solenopsis spp.), pharaoh ant (Monomorium pharaonis).
  • Direct insects such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis, and Schistocerca gregaria.
  • Crustacea insects such as Onychiurus folsomi, Siberian white sibiricus, and Bourletiella hortensis.
  • Dust mites such as cyclamen dust mite (Phytonemus pallidus), chano dust mite (Polyphagotarsonemus latus), mite (Tarsonemus bilobatus), Spider mites such as cabbage mite (Penthaleus erythrocephalus) and wheat mite (Penthaleus major). Spider mites such as rice spider mite (Oligonychus shinkajii), citrus spider mite (Panonychus citri), blue spider mite (Panonychus mori), apple spider mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), spider mite (Tetranychus urticae), etc.
  • Spider mites such as rice spider mite (Oligonychus shinkajii), citrus spider mite (Panonychus citri), blue spider mite (Panonychus mori), apple spider mite (Panonychus ulmi), Kanzawa spider
  • Tick tick Boophilus microplus
  • Rhipicephalus sanguineus Tick tick
  • Tick tick Haemaphysalis longicornis
  • Tick tick Haemophysalis flava
  • Tick tick Haemophysalis campanulata
  • Tick tick Ixo tus tick
  • Tick such as Amblyomma spp.
  • Crawling ticks Cheyletiella yasguri
  • cat ticks Cheyletiella blakei
  • Acne mites such as Inodecarid mite (Demodex canis) and Caterpillar mite (Demodex cati).
  • Cucumber mites such as sheep cucumber mites (Psoroptes ovis).
  • Spider mites such as Sarcoptes scabiei, cattle spider mite (Notoedres cati), chicken spider mite (Knemidocoptes spp.).
  • Southern nematode nematode (Prathylenchus coffeae), Kitane-negususa nematode (Prathylenchus penetrans), Kurume rushes nematode (Prathylenchus vulnus), potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Heterodera lypter Nematodes such as root-knot nematodes (Meloidogyne incognita), rice-spotted nematodes (Aphelenchoides besseyi), and pine wood nematodes (Bursaphelenchus xylophilus).
  • endoparasites such as livestock, poultry, and pet animals that can be controlled using the compounds of the present invention include the following organisms, but the present invention is not limited to these. .
  • Haemonchus Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagotome Genus (Oesophagostomum), Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis ), Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxacaris, Parascaris and other nematodes .
  • Filariidae nematodes such as Wuchereria, Blueia, Onchoceca, Dirofilaria and Loa.
  • Dracunculidae nematodes such as the genus Deacunculus.
  • Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria bovis Eimeria spp. Such as Eimeria ovinoidalis. Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomanas spp., Giardia (Giardia spp.), Toxoplasma spp., Entamoeba histolytica, Theileria spp.
  • the compound of the present invention is also effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, and pyrethroid compounds. That is, the compound of the present invention is composed of the order of mucous (Coleoptera); Eyes), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Flyidae), Isoleoptera (Flea), Licea, and other insects, ticks In addition, pests belonging to gastropods and nematodes can be effectively controlled at low concentrations.
  • the compound of the present invention is extremely useful with little adverse effect on mammals, fish, crustaceans and beneficial insects (beneficial insects such as bees and bumblebees, natural enemies such as honeybees, wasps, mistletoe flies, mosquito bugs, and mites). Has features.
  • the compound of the present invention When using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreezing agent, binder, anti-caking agent. , Disintegrating agents, antifoaming agents, preservatives, anti-degradation agents, etc., adding liquid (soluble concentrate), emulsion (emulsifiable concentrate), wettable powder (wettable powder), water solvent (water soluble powder) Water dispersible granule, water soluble granule, suspension ⁇ concentrate, emulsion ⁇ concentrated ⁇ suspoemulsion, microemulsion, microemulsion, dustable powder ), Granules (tablets), and emulsifiable gels (emulsifiable gels).
  • a surfactant penetrant, spreading agent, thickener, antifreezing agent, binder, anti-caking agent.
  • solid support examples include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, nostirite, and allophane.
  • Bactericides (continued): sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salicylanilide, silthiofam (Silthiofam), simeconazole, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, thiadinyl, tioxymid, tolcrofos -Tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin,
  • the reaction vessel was replaced with nitrogen gas, followed by stirring at 120 ° C. for 3.5 hours. After completion of the reaction, 100 ml of water was added to the reaction solution, followed by extraction with ethyl acetate (200 ml ⁇ 1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 1: 1 to obtain 3.0 g of the desired product as a brown resin.
  • reaction solution was cooled to 0 ° C., and 5 ml of a 60 wt% sodium hydride (dispersed in mineral oil) 80 mg tetrahydrofuran suspension was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C. and stirred at the same temperature for 2 hours. After completion of the stirring, the reaction solution was cooled to room temperature, 0.3 g of methyl iodide was appropriately applied, and stirring was continued at room temperature for 3 days. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with ethyl acetate (50 ml ⁇ 1).
  • the obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the residue obtained after evaporation of the solvent was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 4: 6 to obtain 0.9 g of the desired product as a pale yellow solid.
  • reaction solution was stirred at 80 ° C. for 5 hours under a nitrogen atmosphere.
  • 30 ml of water was added and extracted with ethyl acetate (50 ml ⁇ 1).
  • the obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 4: 6 to obtain 0.4 g of the desired product as a pale yellow solid.
  • the obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with a gradient of n-hexane-ethyl acetate (1: 1) to ethyl acetate-methanol (4: 1) to give 35 mg of the objective compound as colorless. Obtained as an oil.
  • the obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 9: 1 to 3: 1) to obtain 96.2 mg of the desired product as a white solid. . Melting point: 119-120 ° C.
  • Test Example 1 Insecticidal test against brown planthopper A 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm. Rice leaf sheaths are immersed in this chemical solution for about 10 seconds, air-dried and placed in a test tube, and 5 second-instar larvae of Nilaparvata lugens are released per test tube, capped with a sponge and 25 Housed in a constant temperature room. The number of dead insects after 6 days was investigated, and the death rate (%) (number of dead insects ⁇ number of test insects ⁇ 100) was calculated. In addition, the test was performed by 2 continuous systems.
  • Test Example 2 Insecticidal test against leafhopper leafhopper A 10% emulsion of the compound of the present invention (10% wettable powder depending on the compound) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm. Rice leaf sheaths are immersed in this chemical solution for about 10 seconds, air-dried and placed in a test tube, and 5 second-instar larvae of Nephotettix cinchetics are released per test tube, capped with a sponge and 25 Housed in a constant temperature room. The number of dead insects after 6 days was investigated, and the dead insect rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems. As a result, among the compounds tested, the following compounds showed a death rate of 90% or more. Compounds of the present invention: 1-001, 1-007, 1-008, 1-025, 1-027, 1-037, 4-001, 4-002
  • Test Example 4 Insecticidal test against peach aphid Placed wet cotton wool on a glass petri dish with an inner diameter of 3 cm, placed kanran leaves cut into the same diameter on it, and released 4 mosquito aphids (Myzus persicae) adults did.
  • a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm.
  • the chemical solution was sprayed (2.5 mg / cm 2), covered, and stored in a constant temperature room at 25 ° C.
  • the number of dead insects after 6 days was investigated, and the dead insect rate was calculated from the same calculation formula as in Test Example 1.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the characters in the formula represent the following: Cb: number of insects before treatment in the untreated group Cai: number of live insects at the time of final survey in the untreated group Tb: number of insects before treatment in the treated group Tai: number of live insects at the time of final survey in the treated group Among the compounds tested, the following compounds showed a control value of 90% or more.
  • Test Example 7 Effect test on soybean aphids in seed treatment 2.4 mg of the compound of the present invention was diluted in 97.6 ⁇ l of acetone. Four soybean seeds were placed in a 50-ml plastic tube, and the diluted solution was poured from above, so that acetone was completely evaporated while stirring so that the compound was uniformly attached to the seeds. The treated seeds were planted at 4 grains / pot and left in the greenhouse. After the development of primary leaves, two adults of soybean aphids (Aphis glycines) were released in each strain. The number of surviving insects 7 days after release was investigated, and a control value was calculated from the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the characters in the formula represent the following: Cb: number of insects before treatment in the untreated group Cai: number of live insects at the time of final survey in the untreated group Tb: number of insects before treatment in the treated group Tai: number of live insects at the time of final survey in the treated group Among the compounds tested, the following compounds showed a control value of 90% or more.
  • Compounds of the present invention 1-007, 1-025, 1-027, 4-010
  • novel pyrazole derivative in the present invention exhibits excellent pest control activity, particularly insecticidal / miticidal activity, and is extremely useful with little adverse effect on non-target organisms such as mammals, fish and beneficial insects.
  • a compound It should be noted that all of the description, claims and abstract of Japanese Patent Application No. 2011-015351 filed on January 27, 2011 and Japanese Patent Application No. 2011-159137 filed on July 20, 2011. The contents of which are hereby incorporated herein by reference.

Abstract

La présente invention concerne un nouveau pesticide, en particulier un insecticide ou un acaricide. L'invention concerne ainsi un dérivé de pyrazole et un pesticide représentés par la formule générale (1). Dans cette formule, B est noyau pyrazole représenté par la formule structurelle (2). A2 est noyau hétérocyclique D1-1 à D1-102, ou phényle ou analogue substitué par (Z1)q. R1, R2 et R4 sont chacun individuellement atome d'hydrogène, atome d'halogène et/ou C1-C6 alkyle ou analogue. Enfin, Z1 est atome d'halogène, C1-C6 alkyle, ou (C1-C12) alkyle ou analogue éventuellement substitué par R5.
PCT/JP2012/051847 2011-01-27 2012-01-27 Dérivé de pyrazole et pesticide WO2012102387A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO2014007395A1 (fr) * 2012-07-06 2014-01-09 日産化学工業株式会社 Dérivé de pyrazole ou de thiazole, sel de celui-ci, et agent de lutte contre les ravageurs
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US10233155B2 (en) 2016-12-29 2019-03-19 Dow Agrosciences Llc Processes for the preparation of pesticide compounds
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RU2808434C2 (ru) * 2018-05-29 2023-11-28 Кумиай Кемикал Индастри Ко., Лтд. Производное пиразола и средство для борьбы с вредителями

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001163883A (ja) * 1999-12-03 2001-06-19 Pfizer Prod Inc 抗炎症／鎮痛剤としてのスルファモイルヘテロアリールピラゾール化合物
JP2004534754A (ja) * 2001-05-16 2004-11-18 バーテックス　ファーマシューティカルズ　インコーポレイテッド Ｓｒｃおよび他のプロテインキナーゼのインヒビター
WO2010017902A1 (fr) * 2008-08-14 2010-02-18 Bayer Cropscience Aktiengesellschaft Insecticides 4-phényl-1h-pyrazoles
JP2010523570A (ja) * 2007-04-03 2010-07-15 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 置換ベンゼン殺菌・殺カビ剤
WO2011045224A1 (fr) * 2009-10-12 2011-04-21 Bayer Cropscience Ag 1-(pyrid-3-yl)-pyrazole et 1-(pyrimid-5-yl)-pyrazole en tant qu'agents antiparasites

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001163883A (ja) * 1999-12-03 2001-06-19 Pfizer Prod Inc 抗炎症／鎮痛剤としてのスルファモイルヘテロアリールピラゾール化合物
JP2004534754A (ja) * 2001-05-16 2004-11-18 バーテックス　ファーマシューティカルズ　インコーポレイテッド Ｓｒｃおよび他のプロテインキナーゼのインヒビター
JP2010523570A (ja) * 2007-04-03 2010-07-15 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 置換ベンゼン殺菌・殺カビ剤
WO2010017902A1 (fr) * 2008-08-14 2010-02-18 Bayer Cropscience Aktiengesellschaft Insecticides 4-phényl-1h-pyrazoles
WO2011045224A1 (fr) * 2009-10-12 2011-04-21 Bayer Cropscience Ag 1-(pyrid-3-yl)-pyrazole et 1-(pyrimid-5-yl)-pyrazole en tant qu'agents antiparasites

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US9199964B1 (en) 2014-07-31 2015-12-01 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9809570B2 (en) 2014-08-19 2017-11-07 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US10005758B2 (en) 2014-08-19 2018-06-26 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9115115B1 (en) 2014-08-19 2015-08-25 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9522900B2 (en) 2014-08-19 2016-12-20 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9024031B1 (en) 2014-08-19 2015-05-05 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9663489B2 (en) 2014-09-12 2017-05-30 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9896430B2 (en) 2014-09-12 2018-02-20 Dow Agrosciences Llc Process for the preparation of 3-(3-CHLORO-1H-pyrazol-1-yl)pyridine
US9156813B1 (en) 2014-09-12 2015-10-13 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9422265B2 (en) 2014-09-12 2016-08-23 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
US9085552B1 (en) 2014-09-12 2015-07-21 Dow Agrosciences Llc Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine
WO2016071499A1 (fr) 2014-11-06 2016-05-12 Basf Se Composé hétérobicyclique de 3-pyridyle utilisé pour lutter contre les invertébrés nuisibles
US10138254B2 (en) 2014-12-02 2018-11-27 Bayer Cropscience Aktiengesellschaft Bicyclic compounds as pest control agents
US10100033B2 (en) 2016-12-29 2018-10-16 Dow Agrosciences Llc Processes for the preparation of pesticidal compounds
US10233155B2 (en) 2016-12-29 2019-03-19 Dow Agrosciences Llc Processes for the preparation of pesticide compounds
WO2018177995A1 (fr) 2017-03-31 2018-10-04 Bayer Cropscience Aktiengesellschaft Carboxamides tricycliques pour lutter contre les anthropodes
JP7334118B2 (ja) 2017-03-31 2023-08-28 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 節足動物を防除するための三環式カルボキサミド類
CN110475776A (zh) * 2017-03-31 2019-11-19 拜耳作物科学股份公司 用于防治节肢动物的三环羧酰胺
EP4298908A3 (fr) * 2017-03-31 2024-03-20 Bayer Animal Health GmbH Carboxamides tricycliques pour lutter contre les arthropodes
CN110475776B (zh) * 2017-03-31 2024-03-19 拜耳作物科学股份公司 用于防治节肢动物的三环羧酰胺
US11825838B2 (en) 2017-03-31 2023-11-28 Bayer Cropscience Aktiengesellschaft Tricyclic carboxamides for controlling arthropods
JPWO2019230590A1 (ja) * 2018-05-29 2021-07-08 クミアイ化学工業株式会社 ピラゾール誘導体及び有害生物防除剤
JP7305632B2 (ja) 2018-05-29 2023-07-10 クミアイ化学工業株式会社 ピラゾール誘導体及び有害生物防除剤
EP3808738A4 (fr) * 2018-05-29 2022-01-19 Kumiai Chemical Industry Co., Ltd. Dérivé de pyrazole et agent de lutte contre des organismes nuisibles
RU2808434C2 (ru) * 2018-05-29 2023-11-28 Кумиай Кемикал Индастри Ко., Лтд. Производное пиразола и средство для борьбы с вредителями
WO2019230590A1 (fr) 2018-05-29 2019-12-05 クミアイ化学工業株式会社 Dérivé de pyrazole et agent de lutte contre des organismes nuisibles
CN112236421B (zh) * 2018-05-29 2023-12-26 组合化学工业株式会社 吡唑衍生物和有害生物防治剂
KR102633747B1 (ko) 2018-05-29 2024-02-05 구미아이 가가쿠 고교 가부시키가이샤 피라졸 유도체 및 유해 생물 방제제
IL278957B1 (en) * 2018-05-29 2024-03-01 Kumiai Chemical Industry Co Consequences of pyrazole and pesticide
KR20210014653A (ko) 2018-05-29 2021-02-09 구미아이 가가쿠 고교 가부시키가이샤 피라졸 유도체 및 유해 생물 방제제
CN112236421A (zh) * 2018-05-29 2021-01-15 组合化学工业株式会社 吡唑衍生物和有害生物防治剂
US11964957B2 (en) 2018-05-29 2024-04-23 Kumiai Chemical Industry Co., Ltd. Pyrazole derivative and harmful organism-controlling agent
CN115260176A (zh) * 2022-09-02 2022-11-01 安徽农业大学 一种含噁唑基团的吡唑酰胺类衍生物及其制备方法和应用

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