WO2019080227A1 - Composé d'isoxazole benzoyle substitué ou tautomère et sel de celui-ci, procédé de préparation, composition herbicide et application - Google Patents

Composé d'isoxazole benzoyle substitué ou tautomère et sel de celui-ci, procédé de préparation, composition herbicide et application

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Publication number
WO2019080227A1
WO2019080227A1 PCT/CN2017/112015 CN2017112015W WO2019080227A1 WO 2019080227 A1 WO2019080227 A1 WO 2019080227A1 CN 2017112015 W CN2017112015 W CN 2017112015W WO 2019080227 A1 WO2019080227 A1 WO 2019080227A1
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WO
WIPO (PCT)
Prior art keywords
group
alkyl
alkoxy
salt
halogenated
Prior art date
Application number
PCT/CN2017/112015
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English (en)
Chinese (zh)
Inventor
连磊
征玉荣
何彬
彭学岗
金涛
崔琦
刘娜
Original Assignee
青岛清原化合物有限公司
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Application filed by 青岛清原化合物有限公司 filed Critical 青岛清原化合物有限公司
Publication of WO2019080227A1 publication Critical patent/WO2019080227A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—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
    • 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
    • C07D413/14—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
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the invention belongs to the technical field of pesticides, and in particular relates to a substituted benzoyl isoxazole compound or a tautomer thereof, a salt, a preparation method, a herbicidal composition and application.
  • patent CN101981016 A discloses a 4-(3-aminobenzoyl) group of formula (I). 5-5-cyclopropyl isoxazole or a salt thereof: Table A discloses a compound wherein X is Cl and Y is CF 3 (No.
  • Patent WO 97/46530 A1 discloses a ketone compound of the following Formula I as a herbicide:
  • the present invention provides a substituted benzoyl isoxazole compound or a tautomer thereof, a salt thereof, and a preparation method thereof Herbicidal compositions and applications.
  • R 1 R 2 N stands for among them
  • R b is selected from the group consisting of hydrogen, C 1-6 alkyl, halogenated C 1-6 alkyl, C 2-6 alkenyl, halogenated C 2-6 alkenyl, C 1-6 alkoxy C 1-6 alkane , halogenated C 1-6 alkoxy C 1-6 alkyl, C 1-6 alkylcarbonyl, halogenated C 1-6 alkylcarbonyl, C 1-6 alkylsulfonyl, C 1-6 alkane Oxycarbonyl group, C 1-6 alkylaminocarbonyl group, C 1-6 alkylcarbonyl C 1-6 alkyl group, C 1-6 alkoxycarbonyl C 1-6 alkyl group, C 1-6 alkylaminocarbonyl C 1 ⁇ 6 alkyl, unsubstituted or 1-3 independently selected from halogen, nitro, cyano, C 1-6 alkyl, halogenated C 1-6 alkyl, C 1-6 alkoxy, halogen An aryl
  • R a is selected from one or more of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, carboxy, amino, C 1 -C 6 alkylsulfonyl, C 1-6 alkyl, halo C 1 to 6 alkyl, C 2 to 6 alkenyl, halogenated C 2 to 6 alkenyl, C 1 to 6 alkoxy, halo C 1-6 alkoxy, C 1-6 alkylamino, C 2-6 alkenyloxy, halo C 2-6 alkenyloxy, C 2-6 alkenylamino, halogenated C 2-6 alkenylamino, C 1-6 alkylcarbonyl, halogenated C 1-6 alkylcarbonyl a C 1-6 alkoxycarbonyl group, a C 1-6 alkylaminocarbonyl group, a C 1-6 alkoxy C 1-6 alkyl group, a halogenated C 1-6 alkoxy C 1-6 alkyl group, C 1 ⁇
  • Het is selected from 3 to 8 nitrogen-containing heterocyclic groups having 1 to 3 hetero atoms, such as a 4 to 8 membered lactam group, an imidazolyl group, a pyrazolyl group, and a ring having a C and a 1-position.
  • R a One or more groups selected from the group consisting of C 1-4 alkyl, C 1-4 alkoxy, nitro, halogen, cyano, amino, C 1-6 alkylamino, C 1-6 alkylsulfonyl ;
  • R b is selected from one or more of hydrogen, C 1-6 alkyl, halogenated C 1-6 alkyl;
  • Het is selected from the group consisting of butyrolactam, valerolactam, caprolactam, heptanolactam, piperazinone, morpholinone, thiomorpholinone, imidazolyl, pyrazolyl
  • R a is selected from one of fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, nitro, cyano, amino, C 1-6 alkylamino, C 1 -C 6 alkylsulfonyl or a plurality of groups
  • R b is selected from one or more of hydrogen, C 1-6 alkyl, halogenated C 1-6 alkyl;
  • R 11 is selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, cyclopropyl, methoxy, ethoxy, methoxymethyl, methoxyethyl, B Oxymethyl, ethoxyethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, with or without halogen substitution
  • the salt is a potassium salt, a sodium salt, an ammonium salt, a calcium salt, a pyridinium salt or a choline salt.
  • the aryl group is a 6-10 membered aryl group, including a phenyl group or a naphthyl group, etc.; the heteroaryl group is a 5-10 membered heteroaryl group having 1-3 O, S, N heteroatoms, for example Pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazole Base, pyridazinyl, triazinyl, quinolyl, quinoxalinyl, fluorenyl, benzotriazolyl, benzothienyl, benzofuranyl, isoquinolyl, tetrahydroquinolyl, etc. .
  • the salt is an agrochemically acceptable salt, preferably an acid addition salt obtained by reacting a compound of this type with a chemically acceptable acid, or a compound having an acidic group and a basic compound The salt produced.
  • the acid is preferably selected from the group consisting of inorganic acids (such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid) and organic acids (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzene).
  • the basic compound is preferably selected from the group consisting of sodium hydroxide and potassium hydroxide. Calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate or potassium hydrogencarbonate.
  • the above pharmaceutically acceptable salts are easily separated and can be purified by conventional separation methods such as solvent extraction, dilution, recrystallization, column chromatography, and preparative thin layer chromatography.
  • a method of preparing the substituted benzoyl isoxazole compound or a tautomer thereof, a salt thereof, comprising the steps of:
  • the compound of formula II is combined with a hydroxylamine salt such as hydroxylamine hydrochloride in a suitable solvent such as ethanol, methanol, isopropanol, DMF or acetonitrile, a suitable base such as sodium acetate/potassium, sodium hydroxide/potassium, sodium tetrabutoxide/
  • a suitable solvent such as ethanol, methanol, isopropanol, DMF or acetonitrile
  • a suitable base such as sodium acetate/potassium, sodium hydroxide/potassium, sodium tetrabutoxide/
  • the compound of formula I is prepared by reacting potassium, sodium carbonate/potassium at room temperature up to the boiling point of the solvent.
  • the chemical reaction equation is:
  • X is a C1-C6 alkoxy group or a C1-C6 alkylamino group or the like.
  • a herbicidal composition comprising at least one of the substituted benzoyl isoxazole compounds or tautomers and salts thereof as an active component.
  • the active ingredient is present in an amount of from 0.1 to 99% by weight.
  • a method for controlling a harmful plant comprising: using a herbicidally effective amount of the substituted benzoyl isoxazole compound or a tautomer thereof, a salt thereof, or the herbicidal composition described above Plant or harmful plant area.
  • the substituted benzoyl isoxazole compound or a tautomer thereof, a salt thereof, is used to control weeds in a useful crop, preferably, the useful crop is treated by a transgenic crop or a genome editing technique. crop.
  • the compounds of formula I-1 of the present invention have outstanding herbicidal activity.
  • the active substances of the present invention are also effective for perennial weeds which grow from rhizomes, rhizomes, or other perennial organs and are difficult to control. In this regard, it is generally not important to use the substance before, before, or after germination. Particular mention is made of representative examples of monocotyledonous and dicotyledonous weed populations which can be controlled by the compounds of the invention, without limiting the identified species.
  • weed species in which the active substance is effective include monocotyledons: annual oats, rye, grasses, maiden, ferraris, medlar, genus, foxtail, and sedge, and perennial ice. Genus, Bermudagrass, Rhizoma and sorghum, and perennial sedge.
  • dicotyledonous weed species species whose effects can be extended to, for example, the annual genus Polyporus, Amaranth, Pomna, Wild Sesame, Stellaria, Amaranthus, White Mustard, Ipomoea, and Yellow Flower Genus, Matricaria and genus, and perennial weeds, genus, genus and genus.
  • the active substance of the present invention is effectively controlled under the condition of rice seeding Harmful plants, such as cockroaches, genus, genus, genus, genus, cane, and sedge.
  • the compound of the present invention is applied to the surface of the soil before germination, the weeds of the weeds can be completely prevented before the weeds grow, or when the weeds grow out of the cotyledons, and finally completely die after three to four weeks.
  • the compound of the present invention is particularly resistant to the following plants, and is active in the following plants, such as Apila, Xiaoye Sesame, Rolling Stalk, Poria, Ivy, Herba, Arabian, Pansy, Pansy, Poria and Kochia. .
  • the compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, there is no damage to important economic crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybean. Or the damage is trivial. In particular, it is well compatible with cereal crops such as wheat, barley and corn, especially wheat. Thus, the compounds of the invention are highly suitable for the selective control of unwanted plants in agricultural or ornamental plants.
  • Transgenic plants Due to their herbicidal nature, these active substances can be used to control harmful plants in genetically engineered plant cultivation that is known or to be present.
  • Transgenic plants generally have superior traits, such as resistance to specific insecticides, particularly specific herbicides, resistance to pathogenic microorganisms of plant diseases or plant diseases, such as specific insect or fungal, bacterial or viral microorganisms.
  • Other specific traits are related to the following conditions of the product, such as quantity, quality, storage stability, composition and specific ingredients.
  • the obtained transgenic plant product has an increased starch content or an improved starch quality or a different fatty acid composition.
  • the compound of the formula I-1 of the present invention or a salt thereof is preferably used for economically important transgenic crops and ornamental plants such as cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn, or for Cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants.
  • the compounds of the formula I-1 are preferably used as herbicides for the cultivation of useful plants which are resistant or resistant to the toxic effects of the herbicide by genetic engineering.
  • glufosinate herbicides eg EP-0242236 A, EP-0242246 A
  • glyphosate herbicides WO 92/00377
  • sulfonate An ureide herbicide EP-0257993 A, US-5013659 A
  • transgenic crop plant such as cotton which is capable of producing a Bacillus thuringiensis toxin (Bt toxin) which protects against damage by a particular pest (EP-0142924 A, EP-0193259 A);
  • Plant cells of the activity-reducing gene product can be prepared by, for example, 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 product of the above gene product.
  • DNA molecules comprising the entire coding sequence of the gene product, including any flanking sequences that may be present, and the use of DNA molecules comprising only a portion of the coding sequence, which must be sufficiently long to achieve antisense in the cell Effect. Sequences that are highly homologous but not identical to the gene product coding sequence can also be used.
  • the synthesized protein can be localized in any desired plant cell compartment.
  • the synthesized protein can be localized in any desired plant cell compartment.
  • 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 recombined into whole plants using known techniques.
  • the control can be improved or expanded.
  • the range of weeds, the application rate at the time of application is preferably a combination of the resistance of the transgenic crops and the performance of the herbicide, and the effects of the growth and yield of the transgenic crop plants.
  • the invention therefore also provides the use of said compounds as herbicides to control harmful plants in plants of transgenic crops.
  • the compounds of the invention can significantly modulate the growth of crop plants. By modulating the involvement of plant metabolism, these compounds are used to orient the components of the plant and promote harvesting, such as drying and dwarfing the plants. Moreover, they are also suitable for regulating and inhibiting unwanted plant growth without destroying the growth of the crop. Inhibition of plant growth plays a very important role in many monocotyledonous and dicotyledonous crops, as this reduces or completely prevents lodging.
  • the compound of the present invention can be applied using a general formulation, and a wettable powder, a concentrated emulsion, a sprayable solution, a powder or granules can be used.
  • a herbicidal composition comprising a compound of formula 1-1.
  • the physical and/or chemical physical parameters of the compound of formula 1-1 can be formulated in a variety of ways.
  • suitable formulations are: wettable powders (WP), water soluble powders (SP), water soluble concentrates, concentrated emulsions (EC), emulsions such as oil dispersed in water and water dispersed in oil (EW) , sprayable solution, suspension concentrate (SC), dispersible oil suspension (OD), oil or water diluent, solution of miscible oil, powder (DP), capsule suspension (CS) ), seed dressing composition, particles for spreading and soil application, sprayed particles, coated particles and absorbent particles, water dispersible particles (WG), water soluble particles (SG), ULV (super Low volume) formula, microcapsules and wax products.
  • WP wettable powders
  • SP water soluble powders
  • EC concentrated emulsions
  • EW oil dispersed in water and water dispersed in oil
  • SC sprayable solution, suspension concentrate
  • OD dispersible oil suspension
  • DP powder
  • Wettable powders can be uniformly dispersed in water, in addition to active substances, including diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersing agents), such as polyethoxylated alkylphenols, poly Ethoxylated fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkyl phenyl sulfonate, sodium lignosulfonate, 2, 2'- dinaphthylmethane Sodium 6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate.
  • the herbicide active substance is finely ground, for example, using a conventional apparatus such as a hammer mill, a fan mill and a jet mill, and an auxiliary agent is simultaneously or sequentially mixed.
  • a concentrated emulsion such as butanol, cyclohexanone, dimethylformamide, xylene or a higher boiling aromatic compound or a mixture of hydrocarbons or solvents, and adding one more One or more ionic and/or nonionic surfactants (emulsifiers).
  • emulsifiers which can be used are, for example, calcium alkylaryl sulfonates of calcium dodecylbenzene sulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or polyoxyethylene sorbent such as polyoxyethylene sorbitan fatty ester A glycan ester.
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or polyoxyethylene sorbent such as polyoxyethylene sorbitan fatty ester A gly
  • the active substance and the finely divided solid matter are ground to obtain a powder, a solid substance such as talc, a natural clay such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • a water or oil based suspension can be prepared by, for example, wet milling using a commercially available bead mill with or without the addition of a surfactant of the other formulation type described above.
  • an aqueous organic solvent may be used, using a stirrer, a colloid mill and/or a static mixer, and if necessary, a surfactant of another formulation type as described above may be added.
  • the granules are prepared by spraying the active material onto the adsorbate, granulating with an inert material, or concentrating the active material onto the surface of, for example, a sand or kaolinite carrier, granulating the inert material by a binder, and adhering Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil.
  • Suitable actives can be plasmidized by the method of preparing fertilizer granules, and if necessary, fertilizer can be mixed.
  • the water-suspended granules are prepared by a usual method such as spray-drying, fluidized bed granulation, disc granulation, mixing using a high speed mixer, and extrusion without a solid inert material.
  • the content of the active material in the water-suspended granules mainly depending on whether the active material is liquid or solid, and auxiliaries, fillers 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 dispersing agent, an emulsifier, a penetrating agent, a preservative, an antifreezing agent, a solvent, a filler, a carrier, a coloring agent, an antifoaming agent, an evaporation inhibitor, and pH and viscosity modifiers commonly used in all cases.
  • insecticide active substances such as insecticides, acaricides, herbicides and fungicides, or with safeners, fertilizers and/or plant growth regulators.
  • safeners for premixed or filled mix.
  • the commercially available formulations are diluted in a conventional manner, for example, in wettable powders, concentrated emulsions, suspensions, and granules suspended in water, diluted with water.
  • Granules for granules or soil application or sprayed and sprayed solutions are generally not required to be further diluted with inert materials prior to use.
  • the amount of the compound of the formula I-1 required varies depending on the external conditions, such as temperature, humidity, the nature of the herbicide used, and the like. It can have a large range of variation, for example between 0.001 and 1.0 kg/ha, or more active substance, but preferably between 0.005 and 750 g/ha, in particular between 0.005 and 250 g/ha.
  • the activity level criteria for harmful plant damage are as follows:
  • Grade 9 growth control rate is above 95%
  • Level 7 growth control rate is above 80%
  • Level 5 The growth control rate is above 60%
  • Level 2 growth control rate is 5-20%
  • Level 1 The growth control rate is below 5%
  • the above growth control rate is the fresh weight control rate.
  • test compound of the present invention is dissolved in acetone, and then added to Tween 80, diluted with a certain amount of water to a certain concentration of the solution, sprayed to the plant with a spray tower On the object.
  • the cells were cultured for 3 weeks in the greenhouse, and the experimental effects of the weeds after 3 weeks are shown in Table 2.
  • the application dose is 300 g/ha of active ingredient.
  • the compounds of the present invention generally have better weed control effects, especially for the broad-leaved weeds such as sage, sorghum, ramie, which are widely occurring in corn field, and have good effects.
  • the broad-leaved weeds such as Phyllostachys pubescens, which are resistant to ALS inhibitors, have extremely high activity.
  • the compounds of the present invention have been tested to have good activity and crop safety against key weeds in live and transplanted paddy fields at suitable dosages.
  • the post-emergence test conditions were the same as above, and the test was 50 g/ha; the observation time was 20 days after the test.
  • the compounds of the present invention are significantly superior to the comparative compounds in herbicidal activity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (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 composé d'isoxazole benzoyle substitué ou un tautomère et un sel de celui-ci, un procédé de préparation, une composition herbicide et une application. Le composé d'isoxazole benzoyle substitué ou le tautomère et le sel de celui-ci sont représentés par la formule générale I-1 : dans laquelle R1R2N représente, et R représente. La matière active herbicide obtenue présente un meilleur effet herbicide, une gamme plus large du spectre d'activité et une meilleure sécurité. AA%%%R1R2N représente BB%%%R représente
PCT/CN2017/112015 2017-10-24 2017-11-21 Composé d'isoxazole benzoyle substitué ou tautomère et sel de celui-ci, procédé de préparation, composition herbicide et application WO2019080227A1 (fr)

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CN201711002420.3A CN107759581B (zh) 2017-10-24 2017-10-24 取代的苯甲酰基异恶唑类化合物或其互变异构体、盐、制备方法、除草组合物及应用

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CN107759581B (zh) * 2017-10-24 2021-05-14 青岛清原化合物有限公司 取代的苯甲酰基异恶唑类化合物或其互变异构体、盐、制备方法、除草组合物及应用
CN109293640B (zh) * 2018-10-31 2020-05-19 青岛清原化合物有限公司 一种取代的含氮杂芳环甲酰胺衍生物及其除草组合物和用途
WO2020156106A1 (fr) * 2019-01-29 2020-08-06 青岛清原化合物有限公司 Formamides d'aryle hétérocycliques ou sel de ceux-ci, procédé de préparation, composition de désherbage et utilisation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
CN101981016A (zh) * 2008-03-26 2011-02-23 拜尔农作物科学股份公司 有效的除草剂4-(3-氨基苯甲酰基)-5-环丙基异噁唑
CN107759581A (zh) * 2017-10-24 2018-03-06 青岛清原化合物有限公司 取代的苯甲酰基异恶唑类化合物或其互变异构体、盐、制备方法、除草组合物及应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10112104A1 (de) * 2001-03-14 2002-09-26 Bayer Ag Herbizide auf Basis von substituierten Arylketonen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
CN101981016A (zh) * 2008-03-26 2011-02-23 拜尔农作物科学股份公司 有效的除草剂4-(3-氨基苯甲酰基)-5-环丙基异噁唑
CN107759581A (zh) * 2017-10-24 2018-03-06 青岛清原化合物有限公司 取代的苯甲酰基异恶唑类化合物或其互变异构体、盐、制备方法、除草组合物及应用

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