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WO2020006869A1 - Dérivé d'oxime formyle pyrimidinyle substitué, son procédé de préparation, composition herbicide et utilisation associée - Google Patents

Dérivé d'oxime formyle pyrimidinyle substitué, son procédé de préparation, composition herbicide et utilisation associée Download PDF

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Publication number
WO2020006869A1
WO2020006869A1 PCT/CN2018/105678 CN2018105678W WO2020006869A1 WO 2020006869 A1 WO2020006869 A1 WO 2020006869A1 CN 2018105678 W CN2018105678 W CN 2018105678W WO 2020006869 A1 WO2020006869 A1 WO 2020006869A1
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Prior art keywords
alkyl
alkoxy
halogen
substituted
alkylthio
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English (en)
Chinese (zh)
Inventor
连磊
张辽宁
崔琦
程传斌
刘鹏
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Qingdao Kingagroot Chemical Compound Co Ltd
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Qingdao Kingagroot Chemical Compound Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/84—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention belongs to the technical field of pesticides, and particularly relates to a substituted pyrimidineformyloxime derivative, a preparation method thereof, a herbicidal composition and application.
  • the invention provides a substituted pyrimidinylformyloxime derivative, a preparation method thereof, a herbicidal composition, and an application thereof.
  • the compound has excellent herbicidal activity and has higher crop safety, especially for corn, rice, and the like. Crops have established good selectivity.
  • R 1 and R 2 independently represent H, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio, unsubstituted or substituted aromatic , Benzyl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio, and groups represented by the formula -COR 5 where R 5 represents an alkyl group, a haloalkane Group, alkenyl, cycloalkyl, alkoxy, alkenyloxy, cycloalkoxy, alkylthio, alkenylthio, cycloalkylthio, unsubstituted or substituted benzyl, aryl, Heteroaryl, aryloxy, heteroaryloxy, arylmethoxy, heteroarylmethoxy, benzylthio, arylthio, heteroarylthio and available alkyl
  • X represents alkyl, alkoxy, alkylthio, halogen, alkenyl, alkynyl;
  • R 11 independently represents halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, unsubstituted or substituted aryl, Heteroaryl
  • R 12 represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy or benzyloxy;
  • R 13 represents H, alkyl, haloalkyl, phenyl, benzyl or CHR 31 C (O) OR 32 ;
  • R 31 represents H, alkyl or alkoxy;
  • R 32 represents H, alkyl or benzyl;
  • R 14 represents an alkyl group or a halogenated alkyl group
  • R 15 represents H, alkyl, formyl, alkyl acyl, haloalkyl acyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, or benzyloxycarbonyl;
  • R 16 represents H, alkyl;
  • R 17 represents H, alkyl, unsubstituted or phenyl substituted with 1-3 of halogen, alkyl, or alkoxy;
  • R 18 represents H, alkyl; or
  • N CR 17 R 18 represents
  • R 21 and R 24 each independently represent H or an alkyl group
  • R 22 and R 23 each independently represent H or an alkyl group; or NR 22 R 23 represents a 5- or 6-membered saturated or unsaturated ring that does not contain or contain an oxygen atom, a sulfur atom, or another nitrogen atom;
  • R 25 represents an alkyl group
  • A represents halogen and amino
  • B represents hydrogen, halogen, alkoxy, alkylthio, alkylamino, dialkylamino with or without halogen substitution;
  • C represents halogen and haloalkyl.
  • R 1 and R 2 independently represent H, cyano, C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy , C1-C8 acyloxy, C1-C8 alkylthio, unsubstituted or substituted aryl, benzyl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio And a group represented by formula -COR 5 in which R 5 represents C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy , C2-C8 alkenyloxy, C3-C8 cycloalkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C3-C8 cycloal
  • X represents C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halogen, C2-C8 alkenyl, C2-C8 alkynyl;
  • R 11 independently represents halogen, hydroxy, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino , Di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 groups in halogen, C1-C8 alkyl, C1-C8 alkoxy, nitro Base, naphthyl,
  • R 12 represents H, C1-C18 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, phenyl, phenoxy, or benzyloxy;
  • R 13 represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, benzyl or CHR 31 C (O) OR 32 ;
  • R 31 represents H, C1-C8 alkyl or C1-C8 alkoxy
  • R 32 represents H, C1-C8 alkyl or benzyl;
  • R 14 represents C1-C8 alkyl, halogenated C1-C8 alkyl
  • R 15 represents H, C1-C8 alkyl, formyl, C1-C8 alkyl acyl, halo C1-C8 alkyl acyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, or benzyloxy Carbonyl;
  • R 16 represents H, C1-C8 alkyl;
  • R 17 represents H, C1-C8 alkyl, unsubstituted or phenyl substituted by 1-3 of halogen, C1-C8 alkyl, C1-C8 alkoxy;
  • R 18 represents H, C1- C8 alkyl; or
  • N CR 17 R 18 represents
  • R 21 and R 24 each independently represent H or C1-C8 alkyl
  • R 22 and R 23 each independently represent H or C1-C8 alkyl; or NR 22 R 23 represents
  • R 25 represents C1-C8 alkyl
  • A represents halogen and amino
  • B represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, di-C1-C8 alkylamino with or without halogen substitution;
  • C represents halogen, halogenated C1-C8 alkyl.
  • the aryl groups in the R 1 and R 2 groups preferably include a phenyl group, an 2,3-dihydroindenyl group, or a naphthyl group; and the heteroaryl group includes 1-3 O, S, and N heteroatoms.
  • 5- to 10-membered heteroaryl groups such as pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazole Base, oxadiazolyl, thiadiazolyl, pyridazinyl, triazinyl, quinolinyl, quinoxalinyl, indolyl, benzotriazolyl, benzothienyl, benzofuranyl, iso Quinolinyl, tetrahydroquinolinyl and the like.
  • R 1 and R 2 independently represent hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, cyano, C1-C6 alkoxycarbonyl, and unsubstituted or selected Phenyl substituted with one or more of halogen, halogenated C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkoxy, and C2-C6 alkenyl;
  • X represents C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C2-C6 alkenyl, C2-C6 alkynyl;
  • R 11 independently represents halogen, hydroxy, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino , Di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 of halogen, C1-C6 alkyl, C1-C6 alkoxy, nitro Base, naphthyl,
  • R 12 represents H, C1-C14 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy or benzyloxy;
  • R 13 represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, benzyl or CHR 31 C (O) OR 32 ;
  • R 31 represents H, C1-C6 alkyl or C1-C6 alkoxy
  • R 32 represents H, C1-C6 alkyl or benzyl;
  • R 14 represents C1-C6 alkyl, halogenated C1-C6 alkyl
  • R 15 represents H, C1-C6 alkyl, formyl, C1-C6 alkylacyl, halo C1-C6 alkylacyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl;
  • R 16 represents H, C1-C6 alkyl;
  • R 17 represents H, C1-C6 alkyl, unsubstituted or phenyl substituted with 1-3 groups of halogen, C1-C6 alkyl, C1-C6 alkoxy;
  • R 18 represents H, C1- C6 alkyl; or
  • N CR 17 R 18 represents
  • R 21 and R 24 each independently represent H or C1-C6 alkyl
  • R 22 and R 23 each independently represent H or C1-C6 alkyl; or NR 22 R 23 represents
  • R 25 represents C1-C6 alkyl
  • A represents halogen and amino
  • B represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, di-C1-C6 alkylamino with or without halogen substitution;
  • C represents halogen, halogenated C1-C6 alkyl.
  • R 1 and R 2 independently represent hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, cyano, C1-C4 alkoxycarbonyl, and unsubstituted or selected Phenyl substituted with one or more of halogen, halogenated C1-C4 alkyl, C1-C4 alkyl, C1-C4 alkoxy, and C2-C4 alkenyl;
  • X represents C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogen, C2-C4 alkenyl, C2-C4 alkynyl;
  • R 11 independently represents halogen, hydroxy, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino , Di-C1-C4 alkylamino, C1-C4 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 groups of halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro Base, naphthyl,
  • R 12 represents H, C1-C8 alkyl, halo C1-C4 alkyl, C1-C4 alkoxy, phenyl, phenoxy or benzyloxy;
  • R 13 represents H, C1-C4 alkyl, halo C1-C4 alkyl, phenyl, benzyl or CHR 31 C (O) OR 32 ;
  • R 31 represents H, C1-C4 alkyl or C1-C4 alkoxy
  • R 32 represents H, C1-C4 alkyl or benzyl;
  • R 14 represents C1-C4 alkyl, halogenated C1-C4 alkyl
  • R 15 represents H, C1-C4 alkyl, formyl, C1-C4 alkylacyl, halo C1-C4 alkylacyl, C1-C4 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl;
  • R 16 represents H, C1-C4 alkyl;
  • R 17 represents H, C1-C4 alkyl, unsubstituted or phenyl substituted with 1-3 of halogen, C1-C4 alkyl, C1-C4 alkoxy;
  • R 18 represents H, C1- C4 alkyl; or
  • N CR 17 R 18 represents
  • R 21 and R 24 each independently represent H or C1-C4 alkyl
  • R 22 and R 23 each independently represent H or C1-C4 alkyl; or NR 22 R 23
  • R 25 represents C1-C4 alkyl
  • A represents halogen and amino
  • B represents hydrogen, halogen, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino, di-C1-C4 alkylamino with or without halogen substitution;
  • C represents halogen, halogenated C1-C4 alkyl.
  • R 1 and R 2 independently represent hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyano, methoxycarbonyl, ethoxycarbonyl, and unsubstituted or substituted selected from halogen, CF 3, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, methoxy and b Phenyl substituted with one or more groups in the oxy group;
  • X represents chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl;
  • Y represents NH 2 , NHMe, N (Me) 2 ,
  • A represents fluorine, chlorine, and amino
  • B represents hydrogen, fluorine, chlorine, methoxy, ethoxy, and methylthio with or without fluorine;
  • C stands for fluorine, chlorine, and trifluoromethyl.
  • the preparation method of the substituted pyrimidineformyloxime derivative includes the following steps:
  • the reaction is performed in an aprotic solvent under the action of a base and a condensing agent.
  • the reaction temperature is from 0 ° C to 90 ° C, preferably from 25 ° C to 30 ° C.
  • the solvent is selected from one of dichloromethane, dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene.
  • One or more mixed solvents are selected from one of dichloromethane, dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene.
  • One or more mixed solvents One or more mixed solvents.
  • the base is selected from one or more of organic bases such as triethylamine, trimethylamine, DIPEA, and DBU.
  • the condensing agent is PyBop, HATU or HOBt-EDCI.
  • a herbicide composition comprising a herbicidally effective amount of at least one of said substituted pyrimidineformyloxime derivatives.
  • the herbicide composition further includes a formulation aid.
  • a method for controlling harmful plants comprising using a herbicidally effective amount of at least one of said substituted pyrimidineformyloxime derivatives or said herbicide composition on plants or harmful plant areas.
  • the substituted pyrimidineformyloxime derivative is used for controlling harmful plants in useful crops.
  • the useful crop is a transgenic crop or a crop processed by genome editing technology.
  • the compounds of the formula I according to the invention have outstanding herbicidal activity.
  • the active substance of the present invention is also effective for perennial weeds, which are grown from rhizomes, rhizomes, or other perennial organs and are difficult to control. In this regard, it is generally not important whether the substance is used before sowing, before or after germination. Special mention is made of representative examples of monocotyledonous and dicotyledonous weed populations that can be controlled by the compounds of the present invention, without being limited to certain identified species.
  • weed species for which the active substance is effective include monocotyledonous plants: annual oats, rye, grasses, spectrums, ferraris, cormorants, tangs, foxtails and sedges, and perennial ice Puccinellia, Cynodon dactylona, Puccinellia and Sorghum, and perennial sedge.
  • dicotyledonous weed species species whose effects can be extended to, for example, annual Hogweed, Viola, Porona, wild sesame, Stellaria, Polygonum, White mustard, Ipomoea, Saffron Genus, Matricaria and Ramie, and Perennial Weed Convolvulus, Thistle, Rumex and Artemisia.
  • the active substance of the present invention effectively controls harmful plants, such as loquat, Cigurus, Alisma, Polygonum, canegrass and sedge, under the undetermined conditions of rice seeding.
  • the seedlings of weeds can be completely prevented before weeds grow, or the weeds can stop growing when weeds develop cotyledons, and finally die completely after three to four weeks.
  • the compounds of the present invention are particularly active against plants such as Apila, small sesame, Curcuma sibiricum, Stellaria, ivy leaf, Porvana, Arabian Porvana, Pansy and Loquat, Galium .
  • the compound of the present invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, it does not cause any damage to important economic crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton, and soybean Or, the damage is trivial. Especially compatible with cereal crops, such as wheat, barley and corn, especially wheat. Therefore, the compounds of the present invention are very suitable for selectively controlling unwanted plants in agricultural or ornamental plants.
  • Transgenic plants Due to their herbicidal properties, these active substances can be used to control harmful plants in the cultivation of genetically engineered plants that are known or will emerge.
  • Transgenic plants generally have superior traits, such as resistance to specific pesticides, particularly herbicides, resistance to plant diseases or pathogenic microorganisms of plant diseases, such as specific insect or fungal, bacterial or viral microorganisms.
  • Other special traits are related to the following conditions of the product, such as quantity, quality, storage stability, components and special ingredients. As such, it has been known that the obtained transgenic plant products have increased starch content or improved starch quality or different fatty acid components.
  • the compounds of the formula I or their salts according to the invention are preferably used in economically important genetically modified crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or in beets, Cultivation of cotton, soybean, rapeseed, potato, tomato, pea and other vegetable plants.
  • the compounds of the formula I are preferably used as herbicides for the cultivation of useful plants which are resistant or which are genetically engineered to be toxic to the herbicide.
  • Bacillus thuringiensis toxin Bacillus thuringiensis toxin
  • EP-0142924A Bacillus thuringiensis toxin
  • EP-0193259A Bacillus thuringiensis toxin
  • Plant cells with reduced activity gene products can be prepared, for example, by expressing at least one appropriate antisense-RNA, sense-RNA to achieve co-suppression, or by expressing at least one appropriately constructed ribozyme, It specifically cleaves the transcription products of the aforementioned gene products.
  • DNA molecules that contain the entire coding sequence of the gene product including any flanking sequences that may be present, and to use DNA molecules that contain only a portion of the coding sequence, which must be long enough to be antisense in the cell Effect. It is also possible to use sequences that have a high degree of homology to the gene product coding sequence but are not identical.
  • the synthesized protein When expressing a nucleic acid molecule in a plant, the synthesized protein can be localized in any desired plant cell compartment. However, in order to locate in a particular chamber, it is possible, for example, to link the coding region to a DNA sequence to ensure localization at a particular location. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).
  • Transgenic plant cells can be reconstituted into whole plants using known techniques.
  • the control can be improved or expanded
  • the range of weeds, improved application rates during application preferably a good combination of the resistance of transgenic crops and the performance of herbicides, and the effect of the growth and yield of transgenic crop plants.
  • the invention therefore also provides the use of said compounds as herbicides to control harmful plants in transgenic crop plants.
  • the compounds of the present invention can significantly regulate the growth of crop plants. By regulating participation in plant metabolism, these compounds are used to orient the control of plant components and promote harvesting, such as drying and dwarfing plants. They are also suitable for regulating and inhibiting unwanted plant growth without disrupting crop growth. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops because it can reduce or completely prevent lodging.
  • the compounds of the present invention can be applied using general formulations, and wettable powders, concentrated emulsions, sprayable solutions, powders, or granules can be used.
  • the invention thus also provides a herbicide composition comprising a compound of formula I.
  • the compounds of formula I can be formulated in a variety of ways depending on the usual biological and / or chemical physical parameters.
  • wettable powders WP
  • water-soluble powders SP
  • water-soluble concentrates such as oil-in-water dispersion and water-in-oil dispersion emulsion (EW)
  • Sprayable solutions suspending agent concentrates (SC), dispersible oil suspending agents (OD), suspensions with oil or water as a diluent, miscible oil solutions, powders (DP), capsule suspensions (CS ), Seed dressing composition, particles for seeding and soil application, spray particles, coated particles and absorbent particles, water-dispersible particles (WG), water-soluble particles (SG), ULV (ultra Low volume) formulations, microcapsules and wax products.
  • Wettable powders are uniformly dispersible in water.
  • active materials they also include diluents or inert materials, ionic and non-ionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenol, poly Ethoxy fatty alcohols, polyoxyethyl aliphatic amines, fatty alcohol polyglycol ether sulfates, alkyl sulfonates, alkyl phenyl sulfonates, sodium lignosulfonate, 2,2'-dinaphthyl methane Sodium-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleylmethyltaurine.
  • the active substance of the herbicide is finely milled, for example, using commonly used equipment such as a hammer mill, a fan mill, and an air jet mill, and the additives are mixed simultaneously or sequentially.
  • a concentrated emulsion such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents.
  • emulsifiers examples include calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaromatic polyglycol ethers, fatty alcohols Polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbites such as polyoxyethylene sorbitan fatty acid esters Glycan ester.
  • calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaromatic polyglycol ethers, fatty alcohols Polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters
  • the active substance and finely divided solid substance are ground to obtain a powder, such as talc, natural clays such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth.
  • a powder such as talc, natural clays such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth.
  • Water- or oil-based suspensions can be prepared by, for example, wet milling using a commercially available glass bead mill, with or without the addition of another type of surfactant as described above.
  • an aqueous organic solvent may be used, a stirrer, a colloid mill, and / or a static mixer may be used, and if desired, another type of surfactant as described above may be added.
  • Granules are prepared by the following method, spraying the active material on the adsorbent, granulating it with an inert material, or concentrating the active material on the surface of a carrier such as sand or kaolinite, granulating the inert material with a binder, Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil.
  • Suitable actives can be plasmided by the method of preparing fertilizer granules, and if necessary, mixed with fertilizer.
  • Water suspension granules are prepared using common methods, such as spray-drying, fluidized bed granulation, grinding disc granulation, mixing using a high-speed mixer, and extrusion without solid inert materials.
  • Agrochemical formulations usually contain from 0.1 to 99%, in particular from 0.1 to 95% by weight of the active substance formula I.
  • the concentration of the active substance in the wettable powder is, for example, from about 10 to 99% by weight, and the usual formulation components constitute the remaining amount to 100% by weight.
  • the concentration of the active substance in the concentrated emulsion may be about 1 to 90% by weight, preferably 5 to 80%.
  • the powder formulation contains 1 to 30% by weight of active substance, usually 5 to 20% by weight of active substance is preferred, however, the sprayable solution contains about 0.05 to 80% by weight, preferably 2 to 50% by weight of active substance .
  • the content of the active substance in the water-suspended granules it is mainly based on whether the active substance is liquid or solid, and the auxiliary agent, filler and the like used in granulation.
  • the content of the active substance in the aqueous suspension granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the preparation of the active substance may include a tackifier, a wetting agent, a dispersant, an emulsifier, a penetrant, a preservative, an antifreeze, a solvent, a filler, a carrier, a colorant, a defoamer, an evaporation inhibitor, and PH and viscosity modifiers are commonly used in all cases.
  • the mixing method may be Pre-mixed or filled.
  • suitable active substances that can be mixed with the active substance of the present invention are, for example, "World Encyclopedia of New Pesticides and Technologies", China Agricultural Science and Technology Press, 2010.9 and the documents cited here.
  • the herbicide active substance mentioned below can be mixed with a mixture of formula I, (note: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, with a code when appropriate): acetochlor Amine, Butachlor, Acetochlor, Mesochloride, Metolachlor, Smetochlor, Prochlortochlor, Toxachlor, Clotrim, Naproxyl, R-L-naphthopro Carbamide, Diazepam, Phenoxybenzamide, Bifentochlor, Piracetamide, Herbachlor, Flubutyramide, Bromobutyramide, Metformamide, High-Efficiency Dimethoxamine Thiachlor, acetochlor, flu
  • the activity level criteria for harmful plant destruction i.e. growth control rate are as follows:
  • Level 9 The growth control rate is above 95%
  • Level 8 The growth control rate is above 90%
  • the above growth control rate is the fresh weight control rate.
  • the application dose is 45 g / ha of the active ingredient and 450 kg / ha.
  • Control Compound A (From patent CN102675218B).
  • the application dose is 30 g / ha of active ingredient and 450 kg / ha.
  • Control Compound B Control compound C: chlorochloropyridine.
  • the compounds of the present invention significantly improve crop safety and herbicidal activity by changing the parent ring structure, substituents, and carboxy derivative types, especially for corn, rice, etc.
  • the key crops have established good selectivity, while the control compound has poor selectivity to main crops. It can be seen that the present invention has achieved excellent technical effects.
  • the test compound of the present invention was dissolved with acetone, then Tween 80 was added, and the solution was diluted with a certain water to a certain concentration solution, and sprayed immediately after sowing. After being applied in the greenhouse for 4 weeks, the experimental results were observed after 3 weeks. It was found that most of the medicaments of the present invention had an excellent effect under the measurement of 250 g / ha, especially for weeds such as yarrow, matang, ramie, and many compounds. Good selectivity for corn, wheat, rice, soybean, rape.
  • the compounds of the present invention generally have better weed control effects, especially for major weeds such as weeds, tangs, tangs, and ramie, which are widespread in corn fields, rice fields, and wheat fields.
  • Broadleaf, amaranth and other broadleaf weeds have good effects and good commercial value.
  • the broad-leaved weeds such as Amaranth, Sophora pallidum, Amaranth, Maijiagong, Zhuyuan, Stellaria, etc., which are resistant to ALS inhibitors, have extremely high activity.
  • the seeds of yarrow, firefly, wolf grass, and wild auntie were sown, and the soil was gently covered thereon. Thereafter, it was placed in a greenhouse with a water storage depth of 0.5-1 cm, and the tubers of Ye Cigu were implanted the next day or two days later. After that, the water storage depth was kept at 3-4 cm, and the wettability of the compound of the present invention will be adjusted according to the usual preparation method at the time point when the yarrow, firefly, wolfgrass reaches 0.5 leaves, and the wild leaf aunt reaches the primary leaf stage.
  • the water or diluted solution of the powder or suspension is uniformly dropped with a pipette to achieve a predetermined amount of effective ingredients.
  • the soil was leveled to a depth of 3-4 cm, and rice (japonica rice) at the 3-leaf stage was transplanted at a transplant depth of 3 cm the next day.
  • rice japonica rice
  • the compound of the present invention was treated in the same manner as described above.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention se rapporte au domaine technique des pesticides et concerne en particulier, un dérivé d'oxime formyle pyrimidinyle substitué représenté par la formule I, un procédé de préparation de celui-ci, une composition herbicide et une utilisation associée. R1 et R2 représentent indépendamment H, halogène, cyano, nitro, alkyle, etc. X représente alkyle, alcoxy, etc. Y représente nitro ou NR3R4. A représente halogène ou amino. B représente hydrogène, halogène, ou alcoxy, alkylthio, alkylamino, ou dialkylamino avec ou sans substitution halogène. C représente halogène ou haloalkyle. Ledit composé présente une excellente activité herbicide et une plus grande sécurité pour les cultures et offre une bonne sélectivité, en particulier pour des cultures clés telles que le maïs et le riz.
PCT/CN2018/105678 2018-07-05 2018-09-14 Dérivé d'oxime formyle pyrimidinyle substitué, son procédé de préparation, composition herbicide et utilisation associée Ceased WO2020006869A1 (fr)

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CN109721546B (zh) * 2018-12-29 2020-11-20 青岛清原化合物有限公司 取代的嘧啶芳酯衍生物及其制备方法、除草组合物和应用
CN109964943B (zh) * 2019-04-28 2021-05-28 江苏清原农冠杂草防治有限公司 包含嘧啶甲酰基肟类化合物的除草组合物及其应用
CN109942498A (zh) * 2019-05-07 2019-06-28 湖南省农业生物技术研究所 含腙结构的苯基嘧啶衍生物及其制备方法和应用
CN112841196B (zh) * 2019-11-12 2022-02-01 江苏清原农冠杂草防治有限公司 一种包含嘧啶羧酸苄酯类化合物的除草组合物及其应用
CN116965414B (zh) * 2022-04-21 2025-12-30 青岛清原作物科学集团有限公司 一种包含嘧啶甲酰基肟衍生物的除草组合物及其应用
CN118515618A (zh) * 2023-02-17 2024-08-20 青岛清原化合物有限公司 一种苯环取代的嘧啶羧酸类化合物及其制备方法、除草组合物和应用

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