WO2021082901A1 - Composé de phénylisoxazoline et son utilisation - Google Patents

Composé de phénylisoxazoline et son utilisation Download PDF

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WO2021082901A1
WO2021082901A1 PCT/CN2020/120564 CN2020120564W WO2021082901A1 WO 2021082901 A1 WO2021082901 A1 WO 2021082901A1 CN 2020120564 W CN2020120564 W CN 2020120564W WO 2021082901 A1 WO2021082901 A1 WO 2021082901A1
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alkyl
hydrogen
methyl
butyl
haloalkyl
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PCT/CN2020/120564
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Chinese (zh)
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杨吉春
关爱莹
卢政茂
吴峤
马宏娟
刘长令
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沈阳中化农药化工研发有限公司
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Publication of WO2021082901A1 publication Critical patent/WO2021082901A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-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
    • A01N43/80—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
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • the invention belongs to the field of agricultural herbicides, and specifically relates to a phenylisoxazoline compound and its use.
  • CN1939127 discloses CK-1 (Compound No. 9) and CK-2 (Compound No. 12) and has certain herbicidal activity.
  • CN105753853 discloses isoxazoline compounds CK-3 (Compound No. 5) and CK-4 (Compound No. 7) with herbicidal activity.
  • the present invention provides a phenylisoxazoline compound and its use.
  • the present invention provides a phenylisoxazoline compound, as shown in the general formula (I):
  • R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 6 alkyl
  • R 3 is selected from hydrogen, cyano, C 1 -C 6 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;
  • R 4 is selected from hydrogen, cyano, C 1 -C 6 alkyl, CO 2 R 7 or CH 2 OR 8 ;
  • R 5 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 8 , CH 2 SiC [three (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio Or C 1 -C 6 alkylsulfonyl;
  • R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are : Halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy Carbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;
  • R 5 and R 6 may be connected with adjacent C to form a three-membered ring, a four-membered ring, a five-membered ring or a six-membered ring;
  • R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
  • R 7 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furimethylene, thiazolymethylene, tetrahydrofurimethylene or pyridine methylene, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl
  • R 8 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino Sulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkyl Aminothiocarbonyl
  • R 9 and R 10 are respectively selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, SO 2 NH (C 1- C 6 alkyl) or SO 2 N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl);
  • Q is selected from any of the following Q1-Q13;
  • R 11 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
  • R 12 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
  • R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 6 alkyl;
  • R 14 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
  • R 15 is selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 6 haloalkyl;
  • the preferred compound of the present invention is: in the general formula (I)
  • R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 4 alkyl
  • R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
  • R 4 is selected from hydrogen, cyano, C 1 -C 4 alkyl, CO 2 R 7 or CH 2 OR 8 ;
  • R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 Si [tris (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
  • R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
  • R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;
  • R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
  • R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furylidene, thiazolyl, tetrahydrofurylidene or pyridinemethylene, the following groups are: halogen, CN, NO 2 , C 1 -C 4 al
  • R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino Sulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, C 1 -C 4 alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkyl Aminothiocarbonyl
  • R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);
  • Q is selected from any of the following Q1-Q13;
  • R 11 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
  • R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 4 alkyl;
  • R 14 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 4 haloalkyl;
  • a further preferred compound of the present invention is: in the general formula (I)
  • R 1 and R 2 are respectively selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl;
  • R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, Ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy Radical or difluoroethoxy;
  • R 4 is selected from hydrogen, cyano or C 1 -C 4 alkyl
  • R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups, the following groups are: fluorine, chlorine, bromine , CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, three Fluoromethoxy, trifluoroethoxy or difluoroethoxy;
  • R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10.
  • Unsubstituted or substituted by 1-2 groups independently selected from the following groups, the following groups are: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl , Trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;
  • R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;
  • R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
  • R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furanmethylene or tetrahydrofuranmethylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-buty
  • R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 3 alkylamino Sulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, di(C 1 -C 3 )alkyl Aminothiocarbonyl
  • R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);
  • Q is selected from any of the following Q1-Q13;
  • R 11 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl
  • R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
  • R 13 is selected from hydrogen, halogen or C 1 -C 4 alkyl
  • R 14 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl
  • R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 2 haloalkyl;
  • the more preferred compound of the present invention is: in general formula (I)
  • R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
  • R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 groups independently selected from the following: fluorine, chlorine, bromine or methyl;
  • R 4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
  • R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , Methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;
  • R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or 1 -2 independently substituted phenyl groups selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethyl Oxy;
  • R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
  • R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
  • R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, allyl, propargyl, C 1 -C 3 alkoxy C 1- C 3 alkyl, C 1 -C 4 alkylcarbonyloxy C 2 -C 3 alkyl, C 2 -C 4 alkenyl carbonyloxy C 2 -C 3 alkyl, di(C 1 -C 3 alkyl)amino C 2 -C 3 alkyl, (C 1 -C 3 alkyl) amino C 2 -C 3 alkyl, unsubstituted or substituted by 1-4 independently selected from the following groups of phenyl, benzyl, furanolide Methyl or tetrahydrofuran methylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl or tert-butyl;
  • R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkane Alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or benzene with 1-3 independently selected from the following groups Carbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C
  • R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);
  • Q is selected from any of the following Q1-Q13;
  • R 11 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
  • R 12 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, tert Butoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
  • R 13 is selected from hydrogen, fluorine, chlorine, bromine, methyl or ethyl
  • R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
  • R 15 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl or difluoroethyl;
  • a further preferred compound of the present invention is: in the general formula (I)
  • R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine or bromine;
  • R 3 is selected from hydrogen or C 1 -C 4 alkyl
  • R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
  • R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5.
  • R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
  • R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
  • R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
  • R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methyl Acryloyloxy, dimethylaminoethyl, diethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, methylene tetrahydrofuran Group
  • R 8 is selected from hydrogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkane Alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 2 )alkylaminosulfonyl, C 1 -C 2 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl , C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or by 1-3 independently selected from the following groups phenylcarbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 alkyl carbonyl or quinoline carbonyl: fluorine, chlorine, bro
  • R 9 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 10 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1 -C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);
  • Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8 or Q13;
  • R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
  • R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
  • R 13 is selected from hydrogen, fluorine, chlorine, bromine or methyl
  • R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;
  • R 15 is selected from methyl, cyclopropyl or trifluoromethyl
  • the further preferred compound of the present invention is: in the general formula (I)
  • R 1 and R 2 are each selected from hydrogen, fluorine or chlorine
  • R 3 is selected from hydrogen or C 1 -C 4 alkyl
  • R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
  • R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 , CH 2 SiC (CH 3 ) 3.
  • Unsubstituted or substituted phenyl groups independently selected from the following groups: fluorine, chlorine or bromine;
  • R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
  • R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
  • R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
  • R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from the phenyl substituted by the
  • R 8 is selected from hydrogen, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, cyclopropanoyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, two (C 1 -C 2 )alkylaminosulfonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio, C 2 -C 4 alkylcarbonyl, phenylacetyl, phenylpropionyl , 2-Methyl-4-chlorophenoxyacetyl, 2,4-dichlorophenoxyacetyl,
  • R 9 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-chloropropyl or 2-chloropropyl;
  • R 10 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, methoxycarbonylmethylene, ethoxycarbonylmethylene, SO 2 NHCH 3 , SO 2 NHC 2 H 5 , SO 2 N(CH 3 ) 2 or SO 2 N(CH 3 )[CH(CH 3 ) 2 ];
  • Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;
  • R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
  • R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
  • R 13 is selected from hydrogen, chlorine, bromine or methyl
  • R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;
  • R 1 and R 2 are each selected from hydrogen, fluorine or chlorine
  • R 3 is selected from hydrogen, methyl or ethyl
  • R 4 is selected from hydrogen or methyl
  • R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 or CH 2 SiC (CH 3 ) 3 ;
  • R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, cyclopropyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 or CO 2 R 7 ;
  • R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
  • R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
  • R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from phenyl substituted by the following
  • Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;
  • R 11 is selected from methyl or difluoromethyl
  • R 12 is selected from methyl, trifluoromethyl, difluoromethyl, isopropoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
  • R 13 is selected from chlorine, bromine or methyl
  • R 14 is selected from methyl, isopropyl, isobutyl or tert-butyl;
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
  • Cycloalkyl A substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
  • Halogenated alkyl groups straight or branched chain alkyl groups.
  • the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichloromethane Fluoromethyl, trifluoromethyl, etc.
  • Alkoxy straight or branched chain alkyl, connected to the structure via an oxygen atom bond.
  • Halogenated alkoxy groups straight-chain or branched-chain alkoxy groups. The hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms.
  • alkylthio straight or branched chain alkyl group, connected to the structure via a sulfur atom bond.
  • Halogenated alkylthio linear or branched alkylthio. The hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms.
  • Alkenyl straight or branched chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
  • Alkylsulfonyl A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO 2 -), such as a methylsulfonyl group.
  • Halogenated alkylsulfonyl linear or branched alkylsulfonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
  • Alkylsulfinyl A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO-), such as a methylsulfinyl group.
  • Halogenated alkylsulfonyl linear or branched alkylsulfinyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
  • Alkoxycarbonyl The alkoxy is connected to the structure via a carbonyl group, such as CH 3 OCO- or CH 3 CH 2 OCO-.
  • Alkoxyalkyl alkyl-O-alkyl-, such as CH 3 OCH 2 -.
  • Alkylcarbonyloxyalkoxycarbonyl alkyl-CO-O-alkyl- OCO-, such as CH 3 COOCH 2 OCO-, CH 3 COOCH 2 CH 2 OCO- or C 2 H 5 COOCH 2 CH 2 OCO-, etc.
  • Alkylcarbonyl The alkyl group is connected to the structure via the carbonyl group, such as CH 3 CO- or CH 3 CH 2 CO-.
  • Haloalkylcarbonyl The haloalkyl is connected to the structure via a carbonyl group, such as CF 3 CO- or CF 2 HCO-.
  • Cycloalkylcarbonyl Cycloalkyl is connected to the structure via carbonyl, such as cyclopropanoyl or cyclohexylformyl.
  • Halogenated cycloalkylcarbonyl group The halogenated cycloalkyl group is connected to the structure via a carbonyl group, such as 1-chlorocyclopropanoyl and the like.
  • Alkylaminosulfonyl alkyl -NH-SO 2 -, such as CH 3 NHSO 2 -or C 2 H 5 NHSO 2 -and so on.
  • Dialkylaminosulfonyl dialkyl-N-SO 2 -, such as (CH 3 ) 2 NSO 2 -or (C 2 H 5 ) 2 NSO 2 -, etc.
  • Alkylaminocarbonyl alkyl-NH-CO-, such as CH 3 NHCO- or C 2 H 5 NHCO- etc.
  • Dialkylaminocarbonyl dialkyl-N-CO-, such as (CH 3 ) 2 NCO- or (C 2 H 5 ) 2 NCO-, etc.
  • Dialkylaminothiocarbonyl dialkyl-N-CS-, such as (CH 3 ) 2 NCS- or (C 2 H 5 ) 2 NCS-, etc.
  • Alkylthioalkylcarbonyl alkyl-S-alkyl-CO, such as CH 3 SCH 2 CO or CH 3 SCH 2 CH 2 CO.
  • Aryl polyvalent aromatic groups, such as phenyl and naphthyl. Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms.
  • SO 2 NH C 1 -C 4 alkyl: -SO 2 NHCH 3 or -SO 2 NHC 2 H 5 and the like.
  • SO 2 N(C 1 -C 2 alkyl) C 1 -C 4 alkyl: -SO 2 N(CH 3 ) 2 or -SO 2 N(CH 3 )[CH(CH 3 ) 2 ], etc.
  • Part of the compounds of the present invention can be illustrated by specific compounds listed in Table 1 to Table 35, but the present invention is not limited to these compounds.
  • the compound of the present invention can be a compound represented by the general formula I-1, which can be obtained from the oxime-based compound III through chlorination ring closure by the method described in the literature, such as J.Agric.FoodChem. 2005,53,8639-8643, CN105753853, WO2006090234, etc.
  • the oxime compound III can be obtained from the methyl intermediate VI through the oxidation of chromium trioxide by the method described in the literature, and the intermediate V is obtained by decarboxylation to obtain the aldehyde compound IV, which is then obtained through hydroxamidoximation, such as CN1402979, Chemical Reaction Engineering and Technology, 2002, 18(4), 373-376, Journal of Advanced Chemistry, 2003, 24(7), 1225-1230, etc.
  • Methyl intermediate VI can be obtained from intermediate VII through bromination or chlorination of NBS, Br 2 , NCS or Cl 2 , or from intermediate XIV and hydrazine ring.
  • Intermediate VII can be obtained by VIII and hydrazine ring or by re-etherification of X and hydrazine ring.
  • Intermediate VIII can be obtained by reacting XI with R 2 CO 2 CH 3 , R 2 CO 2 C 2 H 5 , (R 2 CO) 2 O or R 2 COCl
  • intermediate XIV can be obtained from XIII and R 2 CO 2 CH 3 , R 2 CO 2 C 2 H 5 , (R 2 CO) 2 O or R 2 COCl reaction, please refer to Bioorganic & Medicinal Chemistry, 2018, 26(12), 3406-3413, Tetrahedron Letters, 2016, 57(14) , 1555-1559, Handbook on Herbicides, 2014, 263-276, etc.
  • X can be obtained by reacting XI with dimethyl carbonate or diethyl carbonate.
  • the compound of the present invention can be a compound represented by the general formula I-2, which can be obtained by reacting intermediate XVI with acetic anhydride or acetyl chloride with the aid of the method described in the literature, and specifically Refer to the Journal of Heterocyclic Chemistry, 1987, 24(5), 1391-6, WO8501637 and WO2000034249; when Q is selected from Q6, the compound of the present invention may be a compound of general formula I-3, which can be obtained from intermediates by the method described in the literature XVI is obtained in two steps.
  • the compound of the present invention can be a compound represented by the general formula I-4, which can be obtained from intermediate XVI in two steps by means of the method described in the literature.
  • Literature can refer to EP860435, WO9817632, Organic Process Research & Development (2001), 5(6), 593-598 or EP448188.
  • the compound of the present invention can effectively control barnyardgrass, setaria, alien sedge, cyperus, crabgrass, shepherd's purse, velvetleaf, zinnia, amaranth, purslane, cocklebur, nightshade, cassia , Wild watermelon seedlings, wild soybeans and other weeds, good results can be obtained at low doses. It has certain safety to wheat, corn and rice, and can be used as a herbicide in agriculture. Therefore, the present invention also includes the use of compounds of general formula (I) for controlling weeds.
  • the compounds of the general formula (I) of the present invention are also suitable for drying and/or defoliating plants.
  • 2-methoxypropene was replaced with 4-methyl-4-ethyl pentenoate, methyl methacrylate, and ethyl methacrylate.
  • step 10 2-methoxypropene was replaced with isobutylene and 4- Ethyl methyl-4-pentenoate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, ethylene glycol dimethacrylate, phenyl methacrylate, isobutyl methacrylate Ester, 2-(tert-butylamino) ethyl methacrylate, tetrahydrofurfuryl methacrylate, N-tert-butylmethacrylamide, 2-methylenylbutyrolactone, 2-(trimethylsilylmethyl) ) Ethyl acrylate, methyl trifluoromethacrylate, 1-cyclohexene-1-methyl methacrylate, methyl acrylate, ethyl acrylate, isobutyl acrylate
  • the herbicidal activity test method of the compound of the invention is as follows:
  • test design dose spray treatment (spray pressure 1.95kg/cm 2 , spray volume 500L/hm 2 , crawler speed 1.48km/h) on a crawler crop sprayer (designed and produced by British Engineer Research Ltd.).
  • the test is set to be repeated 3 times. After the test materials are processed, they are placed in the operation hall. After the liquid is naturally dried in the shade, it is placed in the greenhouse for management according to conventional methods. Observation and recording of the weeds' response to the medicament is carried out. After treatment, the test medicament's control effect on weeds is regularly visually inspected.
  • control effect classification standard 0 means invalid, 100% means complete kill or severe suppression of weeds.
  • Tested for herbicidal activity Compounds 1-12, 1-16, 1-18, 1-19, 1-21, 1-23, 1-24, 1-29, 1-40, 1-42, 1-124, 1 -126, 1-194, 1-195, 1-301, 2-1, 2-12, 2-16, 2-18, 2-19, 2-23, 2-27, 2-32, 2-39 , 2-41, 2-42, 2-52, 2-124, 2-126, 2-160, 2-173, 2-194, 2-195, 2-214, 2-215, etc. at 600g ai/hm
  • the herbicidal activity of pre-emergence and post-emergence treatments on Zinnia, Abutilon, Setaria and Barnyardgrass were all over 85%, showing higher activity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne un composé de phénylisoxazoline et son utilisation. Le composé de phénylisoxazoline est représenté par la formule générale (I). Le composé de formule générale (I) a une bonne activité herbicide, et peut lutter efficacement contre les herbes de type pied-de-coq, Setaria viridis, Cyperus difformis, Juncellus serotinus, Digitaria sanguinalis, Arthraxon hispidus, Abutilon theophrasti, Zinnia elegans, Amaranthus retroflexus, Portulaca oleracea, Xanthium strumarium, Solanum nigrum, Cassia tora, Hibiscus trionum, soja sauvage et d'autres mauvaises herbes ; en outre, le composé peut exercer un bon effet de désherbage à faible dosage, a une certaine sécurité vis-à-vis de cultures telles que le maïs, le blé et le riz, et peut être utilisé en tant qu'herbicide en agriculture.
PCT/CN2020/120564 2019-10-29 2020-10-13 Composé de phénylisoxazoline et son utilisation WO2021082901A1 (fr)

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CN1413209A (zh) * 1999-12-22 2003-04-23 巴斯福股份公司 3－(4,5－二氢异噁唑－5－基)－苯甲酰基吡唑
WO2016095768A1 (fr) * 2014-12-16 2016-06-23 沈阳中化农药化工研发有限公司 Composé d'urée de pyrimidine contenant des isoxazolines et son utilisation
CN105777733A (zh) * 2014-12-16 2016-07-20 沈阳中化农药化工研发有限公司 一种含异恶唑啉的四氢邻苯二甲酰亚胺类化合物及其用途

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DE4417837A1 (de) * 1994-05-20 1995-11-23 Basf Ag Substituierte 3-Phenylpyrazole
CN104812739B (zh) * 2012-09-25 2017-12-12 拜尔农作物科学股份公司 具有除草作用的3‑苯基异噁唑啉衍生物

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WO2016095768A1 (fr) * 2014-12-16 2016-06-23 沈阳中化农药化工研发有限公司 Composé d'urée de pyrimidine contenant des isoxazolines et son utilisation
CN105777733A (zh) * 2014-12-16 2016-07-20 沈阳中化农药化工研发有限公司 一种含异恶唑啉的四氢邻苯二甲酰亚胺类化合物及其用途

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