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WO2010043148A1 - Composé d’éther 2-cyano-3-amino (substitué)-3-phényl-acrylique, sa méthode de préparation et son utilisation - Google Patents

Composé d’éther 2-cyano-3-amino (substitué)-3-phényl-acrylique, sa méthode de préparation et son utilisation Download PDF

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Publication number
WO2010043148A1
WO2010043148A1 PCT/CN2009/074216 CN2009074216W WO2010043148A1 WO 2010043148 A1 WO2010043148 A1 WO 2010043148A1 CN 2009074216 W CN2009074216 W CN 2009074216W WO 2010043148 A1 WO2010043148 A1 WO 2010043148A1
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group
compound
cyano
substituted
preparation
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English (en)
Chinese (zh)
Inventor
王凤云
李刚
沈菲
王耀良
贺鹰
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JIANGSU FLAG CHEMICAL INDUSTRY Co Ltd
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JIANGSU FLAG CHEMICAL INDUSTRY Co Ltd
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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to the field of agricultural fungicides, and more particularly to a 2-cyano-3-(substituted)amino-3-phenyl acrylate compound, a composition, a process for the preparation thereof, and the use of a crop fungicide. Background technique
  • 2-cyanoacrylates were first seen in French patents in 1969, but it was not until 1981 that the hill reaction inhibitory activity of compound 1 was first reported. Such compounds have attracted great interest and synthesis. , the activity and mode of action have been studied in depth. Many of the 2-cyano-3-(substituted)amino-3-substituted phenylacrylic acids and their derivatives have a 3-substituted amine group such as Compound IV, Compound V and Compound VI. However, the structure of such a compound is different from that of the present invention.
  • European Patent EP 885.45 reports that certain other compounds such as 2-cyano-3-(substituted)amino-3-substituted anilino acrylates are reported to have bactericidal activity, but the structures of these compounds are also different from the structure of the present invention.
  • X and Y are respectively fluorine, chlorine, bromine, an alkyl group having 1 to 3 carbon atoms and an alkoxy group, a nitro group or a trifluoromethyl group.
  • An object of the present invention is to provide a 2-cyano-3-(substituted)amino-3-phenylacrylate compound which can control various crop diseases at a small dose.
  • Another object of the present invention is to provide a process for the preparation of the above compounds.
  • Still another object of the present invention is to provide the use of the above compounds in crop bactericides.
  • the object of the invention can be achieved by the following measures:
  • Ri or R 2 are each independently hydrogen, dC 6 unsubstituted or substituted alkyl, Ci-C 6 alkoxy, C 2 -C 6 ester, d-C 6 carboxylic, C 3 -C 6 naphthenic a heterocyclic methyl group, a C 3 -C 6 allyl group, a C 3 -C 6 propargyl group or a benzyl group, wherein the substituent of the substituted alkyl group is a halogen, a hydroxyl group or a cyano group Or alkoxy, said substituent of said substituted heterocyclylmethyl is halogen or monocyclic aryl; R 3 is C 3 -C 8 alkyl, C 3 -C 6 haloalkyl, C 3 - C 6 Alkoxyalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 heterocycloalkylmethyl.
  • R 2 is preferably independently hydrogen, CC 6 unsubstituted or substituted alkyl, CC 6 alkoxy, C 2 -Q ⁇ , d-C 6 carboxylic acid, C 3 -C 6 cycloalkyl, non a substituted or substituted heterocyclylmethyl, allyl, propargyl or benzyl group, wherein the substituent of the substituted alkyl group is a halogen, a hydroxyl group, a cyano group or an alkoxy group, and the substituted heterocyclic group The substituent of the group is 13 ⁇ 4 or benzyl, and the heterocyclylmethyl group is pyrrole or hydrogenated pyrrolemethyl, pyridylmethyl or thiazolylmethyl.
  • R 3 is preferably a C 3 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group or an oxocyclopentanylmethyl group.
  • Ri or R 2 is further preferably independently hydrogen, dC 6 alkyl, dC 6 chloroalkyl, dC 6 hydroxyalkyl, C-Ce cyanoalkyl, dC 6 alkoxyalkyl, d-C 6 alkane, respectively.
  • R 3 is further preferably a C 3 -C 6 alkyl group, a cyclohexyl group or an oxocyclopentanyl group.
  • R 2 is independently hydrogen
  • R 3 is C 3 -C 6 alkyl such as n-propyl, isopropyl, n-butyl, isobutyl or sec Butyl.
  • R 2 or R 3 is as defined above.
  • cyanoacetate is first added to a solution containing ethylene glycol in ethylene glycol dimethyl ether, and then benzoyl chloride is added to carry out the reaction, and finally acidified to obtain 2-cyano-3-hydroxy-3-benzene.
  • Base acrylate; another method for preparing compound II is: in a solvent containing cyanoacetate in dichloroethane, simultaneously adding benzoyl chloride and an acid binding agent triethylamine, finally filtering, and concentrating the filtrate to acidify 2-cyano-3-hydroxy-3-phenyl acrylate.
  • R 3 is a C 3 - 0>alkylalkyl group and various substituted alkoxyalkyl groups and a - ⁇ substituted alkyl group containing one or more halogen atoms such as fluorine, chlorine, bromine and iodine.
  • R 3 containing C 3 - C 6; 3 ⁇ 4 an alkyl group and various substituted alkyl and alkoxy containing one or more halogen atoms such as fluorine, chlorine, bromine, iodine C 3 - C 6 alkoxy substituted base.
  • the compound II and phosphorus oxychloride are placed in a 1:1.1 molar configuration in an inert solvent of dichloromethane or dichloroethane as a solvent, and the acid-binding agent triethylamine is added dropwise. After the completion of the dropwise addition, the reaction is continued for several hours, and then the alkali is used. And, extract, dry. Distilled liquid 2-cyano-3-chloro-3-phenyl acrylate (the following compound ⁇ ), the chemical reaction is as follows:
  • the compound of the present invention has a systemic activity and can be used as a foliar and soil fungicide. Can be applied to control a variety of crop diseases, such as wheat scab, cotton blight, pepper Phytophthora, 7J rice seedling disease, melon gray mold, wheat sheath blight, 7J rice blast, wheat rust Other diseases have better control effects.
  • crop diseases such as wheat scab, cotton blight, pepper Phytophthora, 7J rice seedling disease, melon gray mold, wheat sheath blight, 7J rice blast, wheat rust Other diseases have better control effects.
  • the invention also provides a fungicide composition prepared by using the above compound as an active ingredient and other auxiliary agents (carriers), And a process for the preparation of the composition, the compound of formula I is admixed with a carrier which may comprise a single compound of the invention or a mixture of several compounds.
  • the composition according to the invention is preferably present in an amount of from 1 to 99% by weight of active ingredient.
  • the carrier of the composition of the present invention is a substance which satisfies the following conditions; it is formulated with the active ingredient to facilitate application to the site to be treated, for example, plant, seed, or soil; or is advantageous for storage, transportation or handling.
  • the carrier may be a solid or a liquid, and includes a material which is usually a gas but which has been compressed into a liquid, and a carrier which is usually used in the preparation of the germicidal composition can be used.
  • Suitable solid carriers include natural and synthetic clays and silicates such as diatomaceous earth, talc, attapulgite, aluminum silicate (kaolin), montmorillonite and mica; calcium carbonate; calcium sulfate; ammonium sulfate; And synthetic calcium silicate or aluminum silicate; elements such as carbon and sulfur; naturally synthesized resins such as benzofuran resins, polyvinyl chloride and styrene polymers and copolymers; solid polychlorinated phenols; asphalt; waxes such as beeswax , paraffin.
  • natural and synthetic clays and silicates such as diatomaceous earth, talc, attapulgite, aluminum silicate (kaolin), montmorillonite and mica; calcium carbonate; calcium sulfate; ammonium sulfate; And synthetic calcium silicate or aluminum silicate; elements such as carbon and sulfur; naturally synthesized resins such as benzofuran resins, polyvinyl chloride and st
  • Suitable liquid carriers include water; alcohols such as isopropanol and ethanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexyl ketone; ethers; aromatic hydrocarbons such as benzene, toluene and xylene; petroleum fractions such as Kerosene and mineral oils; chlorinated hydrocarbons such as carbon tetrachloride, perchloroethylene and trichloroethane, usually mixtures of these liquids are also suitable.
  • the pesticidal composition is usually processed into the form of a concentrate and used for transport, which is diluted by the user prior to use.
  • the presence of a small amount of surfactant carrier aids in the dilution process.
  • at least one of the carriers is preferably a surfactant, for example the composition may contain at least two carriers, at least one of which is a surfactant.
  • the surfactant can be an emulsifier, dispersant or wetting agent; it can be a nonionic or ionic surfactant.
  • suitable surfactants include polyacrylic acid and sodium and lignosulfonate salts and calcium salts; condensation of fatty acids or fatty amines or amides having at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide a mixture of glycol, sorbitol, sucrose and pentaerythritol fatty acid esters and fatty amines or amides with ethylene oxide and/or propylene oxide; fatty alcohols or alkylphenols such as p-octylphenol or p-octylcresol a condensation with ethylene oxide and/or propylene oxide; a sulfate or a sulphate of these condensation products; an alkali or alkaline earth metal containing at least 10 carbon atoms of sulfuric acid or sulfonate in the
  • compositions of the present invention are wettable powders, powders, granules and solutions, emulsifiable concentrates, emulsions, suspension concentrates, aerosols, and aerosols.
  • Wettable powders usually contain 25, 50 or 75% by weight of active ingredient, and usually contain 3-10% by weight of dispersing agent in addition to the inert carrier, and if necessary, 0-10% by weight of stabilizer, and/or other additives are added.
  • the powder may usually be formed into a powder concentrate having a composition similar to that of the wettable powder but without a dispersing agent, and further diluted with a solid carrier in the field to give a composition usually containing 0.5 to 10% by weight of the active ingredient.
  • Granules are usually prepared to have a size of 10-100 mesh (1.676-0.152 mm), which can be made by agglomeration or injection technology. Ready. Typically, the granules will contain from 0.5 to 75% by weight of active ingredient and from 0 to 10% by weight of additives such as stabilizers, surfactants, sustained release modifiers.
  • the so-called "flowable dry powder” has a relatively small particle composition with a relatively high concentration of active ingredient.
  • Emulsifying concentrates in addition to solvents, usually contain a cosolvent, 1-50% W/V active ingredient, 2-20% W/V emulsifier and 0-20% W/V other additives such as stabilizers, infiltration when needed.
  • suspension concentrates usually contain 10-75% by weight of active ingredient, 0.5-15% by weight of dispersant, 0.1-10% by weight of other additives such as antifoaming agent, corrosion inhibitor, stabilizer, penetration Agents and adhesives.
  • Aqueous dispersions and emulsions for example compositions obtained by diluting a wettable powder or concentrate according to the invention with water, are also within the scope of the invention.
  • the emulsion may be of two types, water-in-oil or oil-in-water.
  • the compounds of the present invention are useful for controlling diseases caused by fungi (such as Fusarium, Rust or Botrytis, etc.) on plants.
  • fungi such as Fusarium, Rust or Botrytis, etc.
  • the compound represented by the compound I of the present invention is against Gibberella zeae, Fusarium oxysporum, Phytophthora capsici, and rice blast disease.
  • Gibberella fujikuroi) Botrytis cinerea
  • Rhizoctonia solani have good inhibitory activity.
  • A-1 Preparation method of 2-cyano-3-hydroxy-3-phenylpropionate n-propyl ester 1 :
  • the compound represented by the compound I of the present invention is against the wheat scab Gibberella zeae. cotton blight ox_3 ⁇ 4ro /w), ji3 ⁇ 4 ((Phytophthora capsici). rice blast disease
  • Botrytis cinerea and Rhizoctonia solani have good inhibitory activity.
  • the compounds Nol, No2, No3 and No 4 have the best effects.
  • Bactericidal activity test Toxic medium method
  • the drug compound Nol 2-cyano-3-(substituted)amino-3-phenyl acrylate was prepared into a concentration of 2 ⁇ g/ml to prepare a drug-containing medium, and then transferred to wheat after 8 hours.
  • Scab C/Me e//s ⁇ 3 ⁇ 4e
  • Compound A* is a known compound: 2-cyano-3-amino-3-phenyl acrylate

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé d’éther 2-cyano-3-amino (substitué)-3-phényl-acrylique, sa méthode de préparation et son utilisation. Le composé, qui a la structure de formule (I), possède une bonne activité fongicide et peut être utilisé pour la prévention et la guérison de maladies provoquées par divers champignons, tels que Fusarium, le champignon de la rouille ou le champignon de la moisissure grise et ainsi de suite.
PCT/CN2009/074216 2008-10-15 2009-09-25 Composé d’éther 2-cyano-3-amino (substitué)-3-phényl-acrylique, sa méthode de préparation et son utilisation Ceased WO2010043148A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200810155179.2 2008-10-15
CNA2008101551792A CN101381326A (zh) 2008-10-15 2008-10-15 2-氰基-3-(取代)胺基-3-苯基丙烯酸酯类化合物、制备方法及其应用

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WO2010043148A1 true WO2010043148A1 (fr) 2010-04-22

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012065904A3 (fr) * 2010-11-15 2012-07-19 Bayer Cropscience Ag Cyanonénamines et leur utilisation en tant que fongicides
JP2014505019A (ja) * 2010-11-15 2014-02-27 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー シアノエナミン類及び殺菌剤としてのそれらの使用
CN117430529A (zh) * 2023-10-16 2024-01-23 江苏省农药研究所股份有限公司 一种2-氰基丙烯酸酯类化合物盐及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101381326A (zh) * 2008-10-15 2009-03-11 江苏中旗化工有限公司 2-氰基-3-(取代)胺基-3-苯基丙烯酸酯类化合物、制备方法及其应用
CN102695699B (zh) * 2009-10-16 2016-02-24 拜耳知识产权有限责任公司 作为杀菌剂的氨基丙烯酸酯
EP2510787A1 (fr) 2011-04-15 2012-10-17 Bayer Cropscience AG Propènoates en tant que fongicides
CN102219776A (zh) * 2011-04-22 2011-10-19 贵州大学 含咪唑烷基团的氰基乙酸酯衍生物及其制备方法和用途
BR112014001265A2 (pt) * 2011-07-29 2017-02-21 Taisho Pharmaceutical Co Ltd composto de amidina ou seu sal
CN103360254A (zh) * 2012-04-10 2013-10-23 天津亨天利化学有限公司 一种α-氯(2-氯)苯乙酸甲酯的生产方法
CN109776453A (zh) * 2019-03-15 2019-05-21 江苏省农药研究所股份有限公司 一种3-氨基-2-氰基丙烯酸酯类化合物的制备方法
CN109879834A (zh) * 2019-03-15 2019-06-14 江苏省农药研究所股份有限公司 一种3-氨基-2-氰基丙烯酸酯类化合物及其应用
CN113845443A (zh) * 2021-09-27 2021-12-28 江苏省农药研究所股份有限公司 2-氰基-3-氨基丙烯酸酯类化合物的制备方法及中间体
CN117164479A (zh) * 2023-08-21 2023-12-05 甘肃康巴斯生物科技有限公司 一种氨基乙腈盐酸盐的制备方法
CN119977840B (zh) * 2023-11-10 2025-12-30 浙江省化工研究院有限公司 一种2-氰基丙烯酸酯类化合物及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088545A1 (fr) * 1982-03-05 1983-09-14 Fbc Limited Cyanopropenoates à activité fongicide et compositions les contenant
CN1160318C (zh) * 2001-05-08 2004-08-04 江苏省农药研究所 2-氰基-3-取代苯基丙烯酸酯类化合物、组合物及其制备方法以及在农作物杀菌剂上的应用
CN1559210A (zh) * 2004-02-18 2005-01-05 江苏省农药研究所有限公司 2-氰基-3-氨基-3-苯基丙烯酸乙酯防治农作物病害的应用
CN101258850A (zh) * 2008-04-18 2008-09-10 江苏中旗化工有限公司 2-氰基-3-氨基-3-苯基丙烯酸甲酯防治农作物病害的应用
CN101381326A (zh) * 2008-10-15 2009-03-11 江苏中旗化工有限公司 2-氰基-3-(取代)胺基-3-苯基丙烯酸酯类化合物、制备方法及其应用
CN101417962A (zh) * 2008-12-04 2009-04-29 江苏省农药研究所股份有限公司 2-氰基-3-氨基丙烯酸酯衍生物的制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088545A1 (fr) * 1982-03-05 1983-09-14 Fbc Limited Cyanopropenoates à activité fongicide et compositions les contenant
CN1160318C (zh) * 2001-05-08 2004-08-04 江苏省农药研究所 2-氰基-3-取代苯基丙烯酸酯类化合物、组合物及其制备方法以及在农作物杀菌剂上的应用
CN1559210A (zh) * 2004-02-18 2005-01-05 江苏省农药研究所有限公司 2-氰基-3-氨基-3-苯基丙烯酸乙酯防治农作物病害的应用
CN101258850A (zh) * 2008-04-18 2008-09-10 江苏中旗化工有限公司 2-氰基-3-氨基-3-苯基丙烯酸甲酯防治农作物病害的应用
CN101381326A (zh) * 2008-10-15 2009-03-11 江苏中旗化工有限公司 2-氰基-3-(取代)胺基-3-苯基丙烯酸酯类化合物、制备方法及其应用
CN101417962A (zh) * 2008-12-04 2009-04-29 江苏省农药研究所股份有限公司 2-氰基-3-氨基丙烯酸酯衍生物的制备方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012065904A3 (fr) * 2010-11-15 2012-07-19 Bayer Cropscience Ag Cyanonénamines et leur utilisation en tant que fongicides
JP2014505019A (ja) * 2010-11-15 2014-02-27 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー シアノエナミン類及び殺菌剤としてのそれらの使用
US9474275B2 (en) 2010-11-15 2016-10-25 Bayer Intellectual Property Gmbh Cyanoenamines and their use as fungicides
CN117430529A (zh) * 2023-10-16 2024-01-23 江苏省农药研究所股份有限公司 一种2-氰基丙烯酸酯类化合物盐及其制备方法和应用

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