WO2016116058A1 - Composé hétérocyclique de triazine ayant une activité nématicide, son procédé de préparation et son utilisation - Google Patents

Composé hétérocyclique de triazine ayant une activité nématicide, son procédé de préparation et son utilisation Download PDF

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WO2016116058A1
WO2016116058A1 PCT/CN2016/071608 CN2016071608W WO2016116058A1 WO 2016116058 A1 WO2016116058 A1 WO 2016116058A1 CN 2016071608 W CN2016071608 W CN 2016071608W WO 2016116058 A1 WO2016116058 A1 WO 2016116058A1
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徐晓勇
李忠
王高磊
陈修雷
张经纬
邵旭升
须志平
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华东理工大学
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    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N43/82—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
    • A01N43/72—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
    • A01N43/88—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 six-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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D491/02—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 two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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
    • C07D495/02—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 two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the invention belongs to the field of pesticides.
  • the present invention relates to a triazine heterocyclic compound having nematicidal activity, a process for its preparation and use.
  • Plant parasitic nematodes are a class of pathogenic microorganisms that are extremely harmful. They are widely distributed, diverse, and adaptable to the environment. They can be parasitic in the roots, stems, leaves, seeds, shoots and fruits of plants, and can pass feeding activities. Mechanical damage to the host plant and plundering of the host plant's nutrients, especially its esophageal gland secretions, can cause a series of lesions in the host plant, and infect the host plant with other pathogenic microorganisms, causing compound disease and loss of yield. On a global scale, plant parasitic nematodes cause agricultural losses of more than $100 billion annually, severely restricting the development of the agricultural economy.
  • One of the objects of the present invention is to provide a novel chemical nematicide agent with high efficiency, low toxicity and good environmental compatibility, a preparation method and application thereof.
  • X is O or S
  • Q is a carbonyl group Thiocarbonyl-amino Thiocarbonyl-amino-carbonyl Or covalent bond;
  • L is a substituted or unsubstituted C 1-6 alkylene group, a substituted or unsubstituted C 1-6 haloalkylene group, a substituted or unsubstituted C 2-6 alkenylene group, a substituted or unsubstituted C 2-6 haloalkenylene, substituted or unsubstituted C 2-6 alkynylene, substituted or unsubstituted C 2-6 haloalkynylene, substituted or unsubstituted C 3-7 cycloalkylene , substituted or unsubstituted C 5-7 cycloalkenylene, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted 5 or 6 membered heterocyclylene, or substituted Or an unsubstituted 8- to 14-membered heteroarylene ring or a tricyclic ring system, said substitution being substituted by one
  • L is a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 1-6 haloalkyl group, a substituted or unsubstituted C 2-6 alkenyl group, a substituted or unsubstituted C 2-6 halogenated group Alkenyl, substituted or unsubstituted C 2-6 alkynyl, substituted or unsubstituted C 2-6 haloalkynyl, substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted C 5 7 cycloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 5 or 6 membered heterocyclic, or substituted or unsubstituted 8 to 14 membered heteroaryl ring Or a tricyclic ring system, said substitution being substituted by one or more groups
  • A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclic group, or a substituted or unsubstituted 8 to 14 membered heteroaryl ring or three
  • said substitution is substituted by one or more groups selected from the group consisting of halogen, cyano, nitro, R', OR', Si(R') 3 , NR'R", C(O)R', C(O)OR', C(O)NR'R", SR', S(O) m R 1 , S(O) 2 NR'R", OC(O)R 1 , OC(O)NR'R", OS(O) 2 R 1 , OS(O) 2 NR'R", N(R 2 )C(O)R 1 , N(R 2 )C(O)NR 'R', N(R
  • G represents a substituent at any one or more positions of A, and G is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, Substituted or unsubstituted C 2-6 alkynyl, C 2-6 haloalkynyl, or substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted C 5-7 cycloalkenyl, substituted or Unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 5 or 6 membered heterocyclic group, or substituted or unsubstituted 8 to 12 membered heteroaryl bicyclic ring system, said substitution being Substituted by one or more groups selected from the group consisting of halogen, cyano, nitro, R', OR', Si(R') 3 , NR'R",
  • R' and R" are each independently H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C 2-6 haloalkynyl, or substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted C 5-7 cycloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene a substituted or unsubstituted 5 or 6 membered heterocyclic group, or a substituted or unsubstituted 8 to 12 membered heteroarylbicyclic ring system, said substitution being one or more groups selected from the group consisting of Substituted: halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C
  • R 1 is C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, or Substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted C 5-7 cycloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 5 or a 6-membered heterocyclic group, or a substituted or unsubstituted 8- to 12-membered heteroaryl bicyclic ring system, said substitution being substituted by one or more groups selected from the group consisting of halogen, cyano, and nitrate , C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6
  • R 2 is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl or C 2-6 haloalkynyl , or a substituted or unsubstituted C 3-7 cycloalkyl group, a substituted or unsubstituted C 5-7 cycloalkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5 a meta or 6-membered heterocyclic group, or a substituted or unsubstituted 8- to 12-membered heteroaryl bicyclic ring system, said substitution being substituted by one or more groups selected from the group consisting of halogen, cyano , nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2
  • R 3 , R 4 and R 6 are each independently H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 Alkynyl or C 2-6 haloalkynyl;
  • R 5 is C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl or C 2-6 haloalkynyl;
  • n 1 or 2;
  • n 0, 1, 2, 3, 4 or 5.
  • the compound is selected from the group consisting of:
  • X is O or S.
  • L is a substituted or unsubstituted C 1-6 alkylene group, a substituted or unsubstituted C 1-6 haloalkylene group, a substituted or unsubstituted C 2-6 alkenylene group, Substituted or unsubstituted C 2-6 haloalkenylene, substituted or unsubstituted C 2-6 alkynylene, substituted or unsubstituted C 3-7 cycloalkylene, substituted or unsubstituted C 5 7 cycloalkenylene, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted 5 or 6 membered heterocyclylene, or substituted or unsubstituted 8 to 12 a heteroarylene bicyclic ring system, said substitution being substituted by one or more groups selected from the group consisting of halogen, cyano, nitro, C 1-4 alkylene group,
  • L is a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 1-6 haloalkyl group, a substituted or unsubstituted C 2-6 alkenyl group, a substituted or unsubstituted C 2-6 haloene A substituted or unsubstituted C 2-6 alkynyl group, a substituted or unsubstituted C 3-7 cycloalkyl group, a substituted or unsubstituted C 5-7 cycloalkenyl group, a substituted or unsubstituted phenyl group, a substituted or An unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclic group, or a substituted or unsubstituted 8- to 12-membered heteroaryl bicyclic ring system, said substitution being one selected from the group consisting of Or substituted by a plurality of
  • L is any group shown in the L column of Tables 2 to 6 in the examples.
  • M is none; or M is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 Alkynyl, trimethylsilylethynyl, or substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted C 5-7 cycloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted a naphthyl, substituted or unsubstituted 5 or 6 membered heterocyclic group, or a substituted or unsubstituted 8 to 14 membered heteroarylbicyclic or tricyclic ring system, said substitution being selected from the group consisting of Substituted by one or more groups: halogen, cyano, nitro, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 alky
  • M is any group shown in column M of Tables 2 to 6 in the examples.
  • A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclic group, or a substituted or unsubstituted 8 to 12 member.
  • a heteroaryl bicyclic ring system said substitution being substituted by one or more groups selected from the group consisting of halogen, cyano, nitro, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy group, C 1-4 haloalkoxy group, phenoxy group, amino sulfonic acid group, amino-carbonyl group, C 1-4 alkyl-carbonyl group, C 1-4 alkoxy group-carbonyl group, C 1-4 alkylamino-carbonyl or phenylamino-carbonyl.
  • G is H, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, trimethyl Silyl ethynyl, or substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted C 5-7 cycloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted Or an unsubstituted 5- or 6-membered heterocyclic group or a substituted or unsubstituted 8- to 12-membered heteroaryl bicyclic ring system, said substitution being substituted by one or more groups selected from the group consisting of: Halogen, cyano, nitro, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 alkyl-carbonyl, C 1-4 alkoxy-
  • the compound is a compound listed in Tables 2 to 6 in the examples.
  • an agricultural composition comprising:
  • the compound according to the first aspect of the invention or the optical isomer, cis-trans isomer or agrochemically acceptable salt of the compound or the agricultural product according to the second aspect of the invention, is provided in a third aspect of the invention.
  • the composition is used for killing or preventing a plant or plant parasitic nematode or for preparing a nematicide composition for killing or preventing a plant or plant parasitic nematode.
  • a method for producing a compound according to the first aspect of the invention, or an optical isomer, a cis-trans isomer or a pesticide-acceptable salt of the compound is provided.
  • X, Y, Q, L, M, A, G, and n are as defined above.
  • a nematicidal and/or nematode-resistant method comprising the steps of: applying the compound of the first aspect of the invention or the agricultural composition of the second aspect to suffering Or plants that may be exposed to nematodes, the soil around them, or the environment.
  • a process for the preparation of the agricultural composition of the second aspect of the invention comprising the steps of: (1) the compound of the first aspect of the invention, optical isomerism thereof The physicochemical, cis-trans isomer or agrochemically acceptable salt, or a combination thereof; is mixed with (2) a pesticidally acceptable carrier and/or excipient to form the agricultural composition.
  • the inventors have unexpectedly discovered and synthesized a series of triazine heterocyclic compounds having novel structures and significant insecticidal activities after long-term and intensive research. On this basis, the inventors completed the present invention.
  • C 1-6 alkyl refers to a straight or branched alkyl group having from 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec. Base, tert-butyl, or the like.
  • C 2-6 alkenyl refers to a straight or branched alkenyl group having 2 to 6 carbon atoms, such as ethenyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, or a similar group.
  • C 2-6 alkynyl refers to a straight or branched alkynyl group having 2 to 6 carbon atoms, such as an ethynyl group, a propynyl group, or the like.
  • C 3-7 cycloalkyl refers to a cyclic alkyl group having from 3 to 7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or the like.
  • C 5-7 cycloalkenyl refers to a cyclic alkenyl group having from 5 to 7 carbon atoms having one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1 , 3-cyclohexadienyl, 1,4-cyclohexadienyl, or the like.
  • C 1-4 alkoxy refers to a straight or branched alkoxy group having from 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, Butoxy, isobutoxy, sec-butoxy, tert-butoxy, or the like.
  • halogen means fluoro, chloro, bromo, or iodo.
  • halogenated refers to a group substituted with one or more of the above halogen atoms, which may be the same or different, such as trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl, or the like.
  • ring or “ring system” refers to a carbocyclic or heterocyclic ring.
  • heterocycle means that at least one of the atoms forming the heterocyclic backbone is not carbon and is nitrogen, oxygen or sulfur. Typically, the heterocycle contains no more than 4 nitrogens, no more than 2 oxygens, and/or no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated or fully unsaturated ring.
  • ring system refers to a fused ring in which two or more rings are taken together.
  • the term "5- or 6-membered heterocyclyl” refers to a five- or six-membered ring containing one or more heteroatoms selected from nitrogen, oxygen or sulfur, such as pyridinyl, thiazolyl, isothiazolyl, Thienyl, furyl, pyrrolyl, pyrazolyl, pyrimidinyl, tetrahydrofuranyl, 4,5-dihydrothiazol-2-yl, 2-cyanoimido-4-oxo-1,3-thiazolidine- 3-yl, 2-cyanoimino-4-oxo-1,3-thiazin-3-yl, oxazolyl, isoxazolyl, 1H-tetrazolyl, 1H-1, 2, 3 -triazolyl, 4H-1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-
  • heterocyclic ring system refers to a ring system in which at least one ring in the ring system is a heterocyclic ring.
  • heteromatic ring system refers to a system in which at least one ring in the ring system is an aromatic ring.
  • the term "8- to 12-membered heteroaryl bicyclic ring system” or “8- to 14-membered heteroaryl bicyclic or tricyclic ring system” may be selected from the group consisting of benzofuran, benzo[b] Thiophene, anthracene, quinoline, isoquinoline, 1H-carbazole, 1H-benzo[d]imidazole, benzo[d]thiazole, benzo[d]oxazole, benzo[d]isoxazole, Benzo[d][1,2,3]thiadiazole, 2,3-dihydroimidazo[1,2-a]pyridine, quinazoline, quinoxaline, porphyrin, pyridazine, 1,8 -naphthyridine, 4,5,6,7-tetrahydrobenzo[b]thiophene, benzo[b]thiophene-1,1-dioxane, 8H-ind
  • alkyl refers to a group in which one hydrogen atom is absent from an alkane molecule; the term “alkylene” refers to a group in which two hydrogen atoms are absent from an alkane molecule.
  • alkenylene alkynylene
  • cycloalkylene cycloalkenylene
  • phenylene naphthylene
  • heterocyclylene or "Asia”
  • heteroaryl or tricyclic ring system is similar.
  • the groups of the present invention may be substituted with a substituent selected from the group consisting of halogen, cyano, nitro, C 1-6 unless otherwise specified as "substituted or unsubstituted".
  • inert solvent a variety of solvents that do not react with the starting materials, including various linear, branched or cyclic alcohols, ethers or ketones, alkyl halides, 1,4-dioxane, acetonitrile, tetrahydrofuran, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and the like.
  • the compounds of the invention may contain one or more asymmetric centers and thus occur as racemates, racemic mixtures, single enantiomers, diastereomeric compounds and single diastereomers.
  • the asymmetric center that can exist depends on the nature of the various substituents on the molecule. Each such asymmetric center will independently produce two optical isomers, and all Possible optical isomers and diastereomeric mixtures and pure or partially pure compounds are included within the scope of the invention.
  • the invention includes all isomeric forms of the compounds.
  • Y or Q when Y or Q is a covalent bond, it means that the groups on both sides of Y or Q are linked by a covalent bond.
  • active substance of the invention or “active compound of the invention” means a compound of the formula (I), an optical isomer, a cis-trans isomer or a pesticide-acceptable salt thereof. Its heterocyclic structure containing N and S has remarkable nematicidal activity, and the nematicidal spectrum is broad and stable.
  • agrochemically acceptable salt means that the anion of the salt is known and acceptable in forming a pharmaceutically acceptable salt of a nematicide.
  • the salt is water soluble.
  • the acid addition salts formed from the compounds of formula (I) include salts of mineral acids, such as hydrochlorides, phosphates, sulfates, nitrates; and salts comprising organic acids, such as acetates, Benzoate and the like.
  • the active substance of the present invention can be used as a control and elimination of a wide range of agroforestry plant parasitic nematodes.
  • "nematicidal agent” is a collective term for a substance having an action of controlling all plant parasitic nematodes mentioned herein.
  • plant-parasitic nematodes include, but are not limited to, root-knot nematodes, such as Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne exigua, Meloidogyne hapla , Meloidogyne incognita, Meloidogyne javanica, and other genus Meloidogyne; cyst nematodes, such as Globodera rostochiensis, Globodera pallida, Globodera tabacum, and other genus Globodera; heterologous nematodes, such as Heterodera avenae, Heterodera glycines, and Heterodera schachtii ), Heterodera trifolii, and other Heterodera; nematode nematodes, such as Anguina funesta, Anguina tritici, and other genus Anguina );
  • elegans such as Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, and other Ditylenchus; Cone nematodes such as Dolichodorus; Nematodes, such as Helicopterchus dihystera, Helicotylenchus multicintus, and other Helicotyllenus; sheath nematodes, such as Hemicycliophora and Hemicriconemoides; Nematodes, such as the collateral nematode (Hoploaimus columbus) And other genus Hoploaimus; pseudo-root nodule nematodes such as Nacobbus aberrans and other genus Nacobbus; needle nematodes such as Longidorus elongatus and other species of the genus Nematode ( N.
  • elegans such as Paratylenchus
  • root rot nematodes such as Pratylenchus brachyurus, Pratylenchus coffee, Pratylenchus zeae, puncture short Nematode (Pratylenchus penetrans), and other genus Pratylenchus
  • perforated nematodes such as Radopholus similis and other genus Radopholus
  • kidney-shaped nematodes such as Rotylenchus robustus And other Rotylenchus
  • Remnant nematodes such as the genus Trichodorus primitivus and other genus Trichodorus
  • dwarf nematodes such as the Tylenchorhynchus claytoni, indefinite dwarf Nematode (Tylenchorhynchus dubius), and other dwarf nematodes (Tylenchorhynchus); citrus nematodes, such as citrus half Tylenchulus semipene
  • the compounds of the present invention have a particularly good control effect against Meloidogyne incognita.
  • the active substance of the present invention can be prepared into a nematicidal composition in a conventional manner.
  • These active compounds can be formulated into conventional preparations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active substances, in polypolymers Microcapsules, coatings for seeds, and preparations for use with burning devices, such as smoked cartridges, smoked cans and smokers, as well as ULV cold mist and hot fog (Warm Mist) formulation.
  • preparations can be produced by known methods, for example, by mixing the active compound with an extender which is a liquid or liquefied gas or solid diluent or carrier, and optionally a surfactant, an emulsifier and/or A dispersant and/or a foam former.
  • an extender which is a liquid or liquefied gas or solid diluent or carrier
  • a surfactant for example, an organic solvent can also be used as an auxiliary.
  • an organic solvent can also be used as an auxiliary.
  • a liquid solvent When a liquid solvent is used as the diluent or carrier, it is basically suitable, such as: aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride Or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffin, such as mineral oil fractions; alcohols such as ethanol or ethylene glycol and their ethers and lipids; ketones such as acetone, methyl ethyl ketone, methyl isobutyl Ketone or cyclohexanone; or less common polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride Or
  • the diluent or carrier of the liquefied gas refers to a liquid which will become a gas at normal temperature and pressure, such as an aerosol propellant such as a halogenated hydrocarbon and butane, propane, nitrogen and carbon dioxide.
  • the solid carrier may be ground natural minerals such as kaolin, clay, talc, quartz, activated clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals such as highly dispersed silicic acid, alumina And silicates.
  • the solid carrier for the granules is ground and graded natural zircon, such as calcite, marble, pumice, sepiolite and dolomite, And inorganic and organic coarse powder synthesized particles, and organic materials such as sawdust, coconut shell, corn cobs and tobacco stem particles.
  • Emulsified columns of nonionic and anionic agents can be used as emulsifiers and/or foam formers.
  • polyoxyethylene-fatty acid esters polyoxyethylene-fatty alcohol ethers, such as alkaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, and white Protein hydrolysate.
  • Dispersing agents include lignin sulfite waste liquors and methylcellulose.
  • Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, may be employed in the formulation.
  • Colorants such as inorganic dyes such as iron oxide, oxidized diamond and Prussian blue; organic dyes such as azo dyes or metal phthalocyanine dyes; and trace nutrients such as iron, manganese, boron, copper, cobalt, aluminum may be used. And zinc salts, etc.
  • the active compounds of the present invention may be formulated as a mixture with other active compounds in their commercial preparations or in the dosage forms prepared from these preparations, these other active compounds being insecticides, bactericides, fungicides, Herbicides, growth control agents, etc.
  • Insecticides include, for example, phosphates, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms such as avermectin, and fungicides including methoxy acrylates, amides, triazoles Wait.
  • the active compounds of the invention may also be formulated as a mixture with synergists in their commercial preparations or in the dosage forms prepared from these preparations, which are compounds which increase the action of the active compound, due to the activity The compound itself is active, and it is not necessary to add a synergist.
  • formulations usually contain from 0.001 to 99.99% by weight, preferably from 0.01 to 99.9% by weight, more preferably from 0.05 to 90% by weight, based on the total weight of the nematicide composition, of the active compound of the invention.
  • concentration of the active compound in the commercial preparation or the dosage form used can vary within a wide range.
  • concentration of active compound in the dosage form used may range from 0.0000001 to 100% (g/v), preferably between 0.0001 and 1% (g/v).
  • the compound of the formula (I) of the present invention can be produced by the following method, however, the conditions of the method, such as the reactant, the solvent, the base, the amount of the compound used, the reaction temperature, the time required for the reaction, and the like are not limited to the following explanations. .
  • the compounds of the present invention may also be conveniently prepared by combining various synthetic methods described in the specification or known in the art, and such combinations are readily made by those skilled in the art to which the present invention pertains.
  • each reaction is usually carried out in an inert solvent at a reaction temperature of -20 to 120 ° C (preferably -10 to 0 ° C or 20 to 30 ° C or 80 to 100 ° C).
  • the reaction time is usually from 2 to 24 hours, preferably from 4 to 18 hours.
  • the base used in the reaction includes, but is not limited to, triethylamine, diisopropylethylamine, diethylamine, piperidine, piperazine, morpholine, N-methylmorpholine, triethylenediamine ( DABCO), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)
  • potassium carbonate potassium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, or a combination thereof.
  • the starting compound of the formula (d) of the present invention can be synthesized by a method comprising the following steps:
  • a compound of the formula (a) and BTC are reacted in an inert solvent at a constant temperature (e.g., -10 to -5 ° C) to obtain a compound of the formula (b).
  • a constant temperature e.g., -10 to -5 ° C
  • the method comprises the steps of:
  • the compound of the formula (II) of the present invention can be synthesized by the following method:
  • X, Y, L, M, G and A are as defined above, and n is an integer from 0 to 5;
  • the compound of formula (e) and (p1) in the presence of a base (such as potassium carbonate, etc.), an inert solvent (such as DMF or acetone) as a solvent, the compound of formula (e) and (p1)
  • a base such as potassium carbonate, etc.
  • an inert solvent such as DMF or acetone
  • the compound is reacted at a certain temperature (for example, 80 to 90 ° C or reflux) for a certain period of time (for example, 8 to 12 hours). After the reaction is completed, it is cooled to room temperature, and the solvent is distilled off under reduced pressure, and water is added to the residue. The organic phase is washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and then purified to give the compound of formula (II).
  • a base such as potassium carbonate, etc.
  • an inert solvent such as DMF or acetone
  • the compound of the formula (II) can be synthesized by the following method:
  • X, Y, L, M, G and A are as defined above, and n is an integer from 0 to 5;
  • the compound of the formula (III) of the present invention can be synthesized by the following method:
  • X, L, M, G and A are as defined above, and n is an integer from 0 to 5;
  • the compound of the formula (IV) of the present invention can be synthesized by the following method:
  • X, L, M, G and A are as defined above, and n is an integer from 0 to 5;
  • the compound of the formula (V-VI) of the present invention can be synthesized by the following method:
  • X, L, M, G and A are as defined above, and n is an integer from 0 to 5;
  • the compound of the formula (n1) is reacted with the compound of the formula (o'1) at room temperature for a period of time (for example, 8 to 12 hours). After the reaction is completed, it is suction filtered, and the filter cake is weighed with absolute ethanol. Crystallization gives the compound of formula (V).
  • an inert solvent such as acetonitrile
  • the compound of the formula (n1) is reacted with the compound of the formula (o'2) at room temperature for a period of time (for example, 8 to 12 hours). After the reaction is completed, the filtrate is concentrated by suction, and the filtrate is concentrated. Isolation gives the compound of formula (VI).
  • an inert solvent such as dichloromethane
  • the intermediate product is contained in an amount of 10 to 99.99% by weight; preferably 20 to 90% by weight; more preferably 50 to 80% by weight.
  • the inventors can purify the intermediate product and then carry out the next reaction; of course, the reaction mixture containing the compound can be directly subjected to the next reaction.
  • the synthesis of the target compound was similar to the step 1.4 of Example 1, except that 3-(4-bromobutyl)-7-fluorobenzo[d][1,2,3]triazin-4 (3H) was used. - Ketone instead of 3-(3-bromopropyl)-7-chlorobenzo[d][1,2,3]triazin-4(3H)-one. Yellow solid, yield 53%.
  • the synthesis of the target compound was similar to the step 1.4 of Example 1, except that 3-(5-bromopentyl)-6-methylbenzo[d][1,2,3]triazine-4 (3H) was used.
  • the ketone replaces 3-(3-bromopropyl)-7-chlorobenzo[d][1,2,3]triazin-4(3H)-one. Light yellow solid in 65% yield.
  • the synthesis of the target compound was similar to the step 1.4 of Example 1, except that 3-(6-bromohexyl)-7-methoxybenzo[d][1,2,3]triazine-4 (3H) was used.
  • the ketone replaces 3-(3-bromopropyl)-7-chlorobenzo[d][1,2,3]triazin-4(3H)-one. Light yellow solid, yield 41%.
  • the synthesis of the target compound was similar to the step 1.4 of Example 1, except that 3-(3-bromopropyl)-6-methylthieno[3,2-d][1,2,3]triazine was used. -4(3H)-one instead of 3-(3-bromopropyl)-7-chlorobenzo[d][1,2,3]triazin-4(3H)-one. Yellow solid, yield 18%.
  • the synthesis of the target compound was similar to the step 9.2 of Example 9, except that 3-(4-bromobutyl)-7-vinylbenzo[d][1,2,3]triazine-4 (3H) was used. )-ketone instead of 3-(4-bromobutyl)-7-vinylbenzo[d][1,2,3]triazin-4(3H)-one, with 6-bromospiro[porphyrin- 3,2'-[1,3]dioxan-2-one replaces spiro[porphyrin-3,2'-[1,3]dioxolan-2-one. White solid, yield 88%.
  • Triazine-4(3H)-one, 0.036 g (0.192 mmol) of cuprous iodide and 0.34 ml (2.4 mmol) of triethylamine were added with 5 ml of acetonitrile, and reacted at room temperature for 2 hours. An appropriate amount of silica gel was added to the reaction mixture, and the solvent was evaporated.
  • the preparation method of 7-fluorobenzo[d][1,2,3]triazin-4(3H)-one is similar to the step 1.1 of Example 1, except that 2-amino-4-fluorobenzoic acid is used. Instead of 2-amino-4-chlorobenzoic acid.
  • the synthesis of the target compound was similar to the step 15.3 of Example 15 except that 3-(3-hydroxypropyl)-5-bromobenzo[d][1,2,3]triazin-4 (3H) was used. - Ketone instead of 3-(3-hydroxypropyl)-7-fluorobenzo[d][1,2,3]triazin-4(3H)-one. White solid, yield 26%.
  • the synthesis of the target compound was similar to the step 15.3 of Example 15 except that 3-(3-hydroxypropyl)-6-trifluoromethylbenzo[d][1,2,3]triazine-4 was used. (3H)-ketone instead of 3-(3-hydroxypropyl)-7-fluorobenzo[d][1,2,3]triazin-4(3H)-one. White solid in 16% yield.
  • the preparation of the target compound was similar to the step 23.2 of Example 23, except that 3-(3-aminopropyl)-7-nitrobenzo[d][1,2,3]triazine-4 (3H) was used.
  • )-ketone instead of 3-(3-aminopropyl)benzo[d][1,2,3]triazin-4(3H)-one with 3-(5-ethyl-1,2,4- Oxadiazol-3-yl)benzoyl isothiocyanate replaces 2-(trifluoromethoxy)benzoyl isothiocyanate. Light yellow solid in 65% yield.
  • Root-knot nematode belongs to the genus Nematode, Tylenchida, Suborder, Subspecies, Heteroderidea, Meloidogyninae, Root-knot nematode, which is a serious hazard. Plant parasitic nematodes.
  • the sample to be tested is prepared into a liquid solution at a desired concentration, and a sufficient amount of second-instar larvae of the root-knot nematode is prepared. After planting a one-week old cucumber seedling into a test tube, an appropriate amount of the prepared liquid was added to the test tube, and about 2000 larvae were inserted into each test tube. The tubes were placed at 20-25 ° C for 10 hours under light, and after 20 days, the results were counted and the number of roots on the roots of each plant was counted. Each sample was tested 3 times, and each sample was subjected to 4 replicate treatments per test.
  • Distilled water was used as a blank control, distilled water plus root-knot nematode was used as a negative control, and phenylphosphorus and avermectin solutions were used as positive controls.
  • Inhibition rate (%) (negative control score - test group score) / negative control score ⁇ 100%
  • Y is "-" to indicate that Y is a covalent bond
  • M is "/" to indicate that M is none.
  • Embodiment 26 A composition comprising a nematicidal agent of the compound of the present invention
  • the following components were prepared in proportion: 5.0% by weight, the same as any of the compounds II-1 to VI-36 (Tables 2 to 6); 30.0% polyvinylpyrrolidone-vinyl acetate copolymer; 30.0% Alkyl polyglycosides; 15.0% oleic acid glyceride; 20.0% water.
  • the following components were prepared in proportion: 65.0% of any of the compounds II-1 to VI-36 (Tables 2 to 6); 2.0% of dodecylphenol polyglycol ether; 4.0% of sodium lignosulfonate; 6.0% sodium aluminum silicate; 23.0% montmorillonite (calcined).
  • the following components were prepared in proportion: 20.00% of any of the compounds II-1 to VI-36 (Tables 2 to 6); 5.00% polyvinylpyrrolidone-vinyl acetate copolymer; 5.00% montanic acid wax; 1.00% wood Calcium sulfonate; 1.00% polyoxyethylene/polyoxypropylene block copolymer; 2.00% stearyl alcohol (POE 20); 0.20% polyorganosilicon; 0.05% colorant red dye; 65.75% water.

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Abstract

La présente invention concerne un composé hétérocyclique de triazine ayant une activité nématicide, son procédé de préparation et son utilisation. Plus spécifiquement, l'invention concerne un composé de formule (I) ou un isomère optique, un isomère cis-trans ou des sels acceptables du point de vue pesticide de celui-ci, et leur procédé de préparation. Une composition à visée agricole comprenant le composé et son utilisation sont en outre décrites. Le composé manifeste une excellente activité nématicide.
PCT/CN2016/071608 2015-01-21 2016-01-21 Composé hétérocyclique de triazine ayant une activité nématicide, son procédé de préparation et son utilisation WO2016116058A1 (fr)

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PL232272B1 (pl) * 2015-07-28 2019-05-31 Fundacja Univ Im Adama Mickiewicza W Poznaniu Zastosowanie amidów 7-karboksybenzo[1,2,3]tiadiazolu jako regulatora wzrostu roślin
CN108084104A (zh) * 2017-12-27 2018-05-29 温州大学 1，2，3-苯并三嗪-4（3h）-酮化合物的合成方法
CN108276352B (zh) * 2018-03-13 2022-09-20 华东理工大学 一种具有杀线虫活性的含氮杂环化合物及其制法和用途

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