WO2020034181A1 - Composé de sel de triphényl-phosphonium quaternaire, son procédé de préparation et son application - Google Patents

Composé de sel de triphényl-phosphonium quaternaire, son procédé de préparation et son application Download PDF

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WO2020034181A1
WO2020034181A1 PCT/CN2018/100964 CN2018100964W WO2020034181A1 WO 2020034181 A1 WO2020034181 A1 WO 2020034181A1 CN 2018100964 W CN2018100964 W CN 2018100964W WO 2020034181 A1 WO2020034181 A1 WO 2020034181A1
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formula
compound represented
compound
catalyst
preparation
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PCT/CN2018/100964
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WO2020034181A9 (fr
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覃兆海
王家尧
刘雪莲
唐大超
肖玉梅
李佳奇
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中国农业大学
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Priority to AU2018436544A priority Critical patent/AU2018436544B2/en
Priority to CA3101114A priority patent/CA3101114C/fr
Priority to PCT/CN2018/100964 priority patent/WO2020034181A1/fr
Publication of WO2020034181A1 publication Critical patent/WO2020034181A1/fr
Publication of WO2020034181A9 publication Critical patent/WO2020034181A9/fr

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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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds

Definitions

  • the invention belongs to the technical field of pesticides, and particularly relates to a class of triphenylphosphonium salt compounds, and a preparation method and application thereof.
  • This kind of fungicide has high efficiency, broad spectrum, strong surface activity, strong slime stripping and cleaning effect, low foaming, low dosage, low toxicity, no environmental pollution, good compatibility, wide pH range (pH 2 ⁇ 12) And good chemical stability and other advantages, is the representative of a new generation of cationic surfactant fungicides, widely used in medical and health, oil field extraction, water treatment, food industry, agriculture and daily life and many other fields.
  • the quaternary phosphonium salt has a high affinity for mitochondria, it is widely used in the mitochondrial targeted delivery of drugs in the field of medicine. , Help reduce the amount of drugs used and reduce toxic and side effects.
  • An object of the present invention is to provide a triphenylphosphonium salt compound and a preparation method thereof.
  • X is selected from CH 2 , N, S or O;
  • Y is selected from halogen (Cl, Br or I), CH 3 SO 3 , CF 3 CO 2 , CH 3 CO 2 , CF 3 SO 3 , PhCO 2 , HOC 6 H 4 CO 2 , (CH 2 CO 2 ) 2 , (CHCO 2 ) 2, and any one of Formula W;
  • n is an integer from 0 to 16;
  • Q is selected from Formula Ia or Formula Ib;
  • R 1 represents H or a C 1 to C 12 alkyl group
  • Ar is selected from any one of the following A 1 to A 8
  • Q 1 is selected from any one of H or B 1 to B 11 ;
  • R 2 , R 3 , R 4 , R 5 and R 6 are all selected from hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, C 1 -C 8 fluoroalkyl, C 1 -C 8 fluoroalkoxy, halogen, nitro, cyano, benzene At least one of oxy, pyridyloxy, methanesulfonyl, and trifluoromethanesulfonyl, the halogen is selected from any one of fluorine, chlorine, bromine, and iodine; m is an integer from 0-4; o, q and r are both integers of 0-5; p is an integer of 0-3; the binding sites of R 2 , R 3 , R 5 and R 6 are at least one of the remaining 5 binding sites, where, when When When When When When When When When When When When When When When When When When When When When When When When When When
  • R 7 is selected from hydrogen, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 fluoroalkyl, C At least one of 1- C 5 fluoroalkoxy, halogen, nitro, cyano, phenoxy, pyridyloxy, carboxyl, methanesulfonyl, and trifluoromethanesulfonyl, the halogen selected from fluorine Any of chloro, bromo, and iodine, s is an integer from 0 to 5; the binding site of R 7 is at least one of the remaining 5 binding sites, where when s> 1, R 7 may be The same or different; in the formula B 6 , R 8 and R 9 are both selected from hydrogen, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 fluoroalkyl any one fluoroalkyl C alkoxy and
  • Z is selected from N or CH, and M is selected from NH or O.
  • X is selected from CH 2 or O;
  • Y is selected from halogen, AcO (CH 3 CO 2 ) , P-toluenesulfonyl (TsO), PhCO 2 and HOC 6 H 4 CO 2 ;
  • n is an integer of 4 to 11;
  • Q is selected from Ia or Ib.
  • Halogen refers to fluorine, chlorine, bromine, and iodine.
  • Alkyl represents a linear or branched alkyl group, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, tert-pentyl and the like.
  • the aryl group and the aryl part of the aryloxy group include a phenyl group, a pyridyl group, a furyl group, and the like.
  • geometric isomers are formed by carbon-carbon double bonds or carbon-nitrogen double bonds connecting different substituents (respectively different configurations are represented by Z and E).
  • the compound of formula I according to the present invention may be a Z-isomer, an E-isomer, or a mixture of the two in any ratio.
  • the compound of formula I of the present invention may be specifically selected from the following numbered compounds
  • the compound of formula I of the present invention may be specifically selected from the following numbered compounds
  • Another object of the present invention is to provide a method for preparing the above-mentioned phosphonium salt compound (compound represented by Formula I).
  • the method for preparing a sulfonium salt compound (compound represented by Formula I) provided by the present invention includes the following steps: under a catalyst or catalyst-free condition, a compound represented by Formula VII and triphenylphosphine are subjected to a nucleophilic reaction in an organic solvent To obtain a compound represented by formula I.
  • the definitions of Y, Q, X and n are the same as those in the formula I; in the above preparation method, the catalyst is sodium iodide or potassium iodide.
  • the molar ratio of the catalyst to the compound represented by formula VII is (0.01-0.1): 1.
  • the reaction temperature of the nucleophilic reaction is 25-180 ° C, preferably 80-115 ° C, specifically 82 ° C, and the reaction time is 4-24h, and specifically 8-12h.
  • the molar ratio of the compound represented by Formula VII to triphenylphosphine is 1: (1-2), and specifically, 1: (1-1.3).
  • the organic solvent is selected from at least one of acetonitrile, ethylene glycol dimethyl ether, benzene, toluene, and 1,2-dichloroethane.
  • the nucleophilic reaction can be specifically carried out according to the following steps: evacuating the catalyst, triphenylphosphine and the compound represented by formula VII and magnetons, filling with nitrogen; adding an organic solvent under nitrogen protection, and stirring at room temperature for 5-10 minutes, and then This is reacted at 80-115 ° C for 8-12 hours to obtain a compound represented by formula I.
  • the compound represented by the formula VII is prepared as follows: the compound represented by the formula IV (or the compound represented by the formula V) in the presence of a catalyst (or the presence of an acid-binding agent) in an organic solvent and the compound represented by the formula VI The compound shown is reacted to obtain a compound represented by formula VII.
  • the definition of Q 1 and Ar is the same as Formula Ia; in Formula V, the definition of Q 2 is the same as Formula Ib; in Formula VI, the definitions of X, Y, and n are the same as those of Formula I, U The definitions are all the same as Ib.
  • U is a COO group.
  • the acid-binding agent is pyridine, triethylamine, ethylenediamine, potassium carbonate, cesium carbonate, NMM (N-methylmorpholine), and NaH; and the catalyst is EDCI / HOBT, CDI, DMAP / DCC, HATU / DIPEA, and DIC.
  • the molar ratio of the acid binding agent to the compound represented by Formula IV is (2-5): 1, and specifically, it may be: (2-3): 1.
  • the molar ratio of the catalyst to the compound represented by Formula IV is (1-2.5): 1, and specifically, it can be: (1.2-2): 1.
  • the molar ratio of the compound represented by IV to the compound represented by Formula VI is 1: (1-2), and specifically, it can be 1: 1.05.
  • the molar ratio of the acid binding agent to the compound represented by Formula V is (2-5): 1, and specifically, it can be: (2-3): 1.
  • the molar ratio of the catalyst to the compound represented by Formula V is (1-2.5): 1, and specifically, it can be: (1.2-2): 1.
  • the molar ratio of the compound represented by V and the compound represented by Formula VI is 1: (1-2), and specifically may be 1: 1.05.
  • the reaction temperature of the reaction is -20-35 ° C, and the reaction time is 1-6h.
  • the organic solvents are dichloromethane, tetrahydrofuran, acetonitrile, N, N-dimethylformamide (DMF), 1,4-dioxane, and toluene.
  • the reaction is selected according to the following steps (taking the reaction of the compound represented by Formula IV and the compound represented by VI as an example): the compound represented by Formula IV, the catalyst DMAP / DCC and the magnetons are evacuated and filled with nitrogen; under the protection of nitrogen Add an organic solvent, lower the temperature of the ice-salt bath to -10 ° C, and stir for 5-10 min. Then dilute Formula V in the solvent and slowly drop it into the reaction flask for 0.5-4 h to obtain the compound represented by Formula VII.
  • the compound represented by formula IV is prepared as follows: the compound represented by formula II and an acid binding agent are reacted with a compound represented by formula III in an organic solvent to obtain a compound represented by formula IV.
  • the definition of Ar is the same as Formula I; in Formula III, R 1 is the same as Formula I.
  • the acid-binding agent is pyridine, triethylamine, ethylenediamine, potassium carbonate, cesium carbonate, and NaH.
  • the molar ratio of the catalyst to the compound represented by Formula II is (2-5): 1, and specifically may be: (2-3): 1.
  • the molar ratio between the compound represented by II and the compound represented by formula III is 1: (1-1.2), and specifically, it can be 1: 1.05.
  • the reaction temperature of the reaction is -20-35 ° C, and the reaction time is 1-6h.
  • the organic solvents are dichloromethane, tetrahydrofuran, acetonitrile, N, N-dimethylformamide (DMF), 1,4-dioxane, and toluene.
  • the reaction can be specifically carried out according to the following steps: evacuating the acid binding agent, the compound represented by Formula II and the magnet, and filling it with nitrogen; adding an organic solvent under the protection of nitrogen, cooling the ice-salt bath to -10 ° C and stirring for 5-10 minutes, Dilute the formula III with the solvent and slowly drop it into the reaction flask for 0.5-4 h to obtain the compound represented by the formula IV.
  • the compounds represented by formula II, formula III, formula V and formula VI in the present invention can be purchased through commercial routes or obtained by one-step reaction of raw materials.
  • the compound represented by formula II can be biphenyl containing various substituents. 2-Amine, arylpyridylamine, aniline, benzylamine and various heterocyclic amines.
  • the compound represented by formula III can be specifically obtained from various substituted benzoic acid, phenylacetic acid, and various substituted heterocyclic formic acid in one step.
  • the invention also protects a bactericide composition and a preparation method thereof.
  • the composition includes a sulfonium salt compound (compound represented by Formula I) and an agriculturally acceptable carrier, wherein the mass percentage content of the sulfonium salt compound (active ingredient) in the single agent is 0.1 to 99%, specifically, It is 30 to 60%.
  • the phosphonium salt compound may be a single compound of the present invention or a mixture of several compounds of the present invention.
  • the preparation method of the fungicide composition provided by the present invention includes the following steps: the sulfonium salt compound (the compound represented by the formula I) and an agriculturally acceptable carrier are mixed uniformly to obtain the preparation.
  • the agriculturally acceptable carrier has the following characteristics: 1) after being formulated with the active ingredient, it is convenient to apply to the site to be treated, such as: plants, seeds or soil; 2) it is convenient for storage, transportation or handling; 3) it can be Is a solid or liquid, including substances that are usually gas but have been compressed into a liquid. In short, carriers commonly used in formulating bactericidal preparations for agricultural use can be used.
  • the agriculturally acceptable carrier may be specifically selected from a solid carrier and / or a liquid carrier.
  • the solid support is selected from at least one of natural or synthetic silicate, ammonium sulfate, calcium sulfate, aluminum oxide silicate, natural or synthetic resin, polychlorophenol, starch, bentonite, and wax, wherein, the The natural or synthetic silicate may be specifically selected from at least one of attapulgite, talc, aluminum silicate, diatomaceous earth, mica, montmorillonite, and calcium silicate, and the natural or synthetic resin may be specifically selected from At least one of a benzofuran resin, a styrene polymer (molecular weight of 50,000 to 200,000), and a styrene copolymer (such as a styrene-butadiene copolymer); the wax may be specifically selected from beeswax and / Or paraffin.
  • natural or synthetic silicate may be specifically selected from at least one of attapulgite, talc, aluminum silicate, diatomaceous earth, mica, montmorillonite,
  • the liquid carrier is selected from at least one of water, a C1-C4 alcohol, a C3-C8 ketone, an aromatic hydrocarbon, a petroleum fraction, and a C6-C12 chlorinated hydrocarbon, wherein the alcohol may specifically be ethanol and / or Ethylene glycol, the ketone may be at least one of acetophenone, acetone, methyl ethyl ketone, and cyclohexanone, the aromatic hydrocarbon may be at least one of benzene, toluene, and xylene, and the petroleum fraction may be specifically It may be kerosene and / or mineral oil, and the chlorinated hydrocarbon may specifically be at least one of carbon tetrachloride, dichloromethane, and trichloroethane.
  • the alcohol may specifically be ethanol and / or Ethylene glycol
  • the ketone may be at least one of acetophenone, acetone, methyl ethyl ket
  • the fungicide composition is processed into a concentrate and used for transportation, which is diluted by the user before application.
  • the fungicide composition provided by the present invention may further include a surfactant.
  • the added amount of the surfactant may be an acceptable amount in agricultural fungicides.
  • the surfactant may be selected from at least one of an emulsifier, a dispersant, a wetting agent, and a penetrant.
  • the emulsifier may be specifically selected from agricultural milk 500 # (calcium alkyl phenyl luteinate), agricultural milk 600 # phosphate (phenylphenol polyoxyethyl ether), agricultural milk 700 # (alkylphenol formaldehyde resin polyoxylate) Ethyl ether), agricultural milk 1600 # (phenethylphenol polyoxyethyl polypropylene ether), polyoxyalkylene alkyl aryl ether, and at least one of ethylene oxide-propylene oxide block copolymer Species.
  • the dispersant may be specifically selected from the group consisting of polycarboxylate, ligninsulfonate, alkylphenol polyoxyethylene formaldehyde condensate sulfate, calcium alkylbenzenesulfonate calcium salt, benzenesulfonic acid formaldehyde condensate sodium salt, and lauryl sulfate At least one of sodium, sulfonated castor oil sodium salt, sodium alkylaryl sulfonate, alkylphenol polyoxyethylene pyrimide, fatty acid polyoxyethylene ester, and ester polyoxyethylene pyrimide.
  • the wetting agent may be at least one selected from the group consisting of sodium dodecyl sulfate, sodium dodecylbenzenesulfonate, BX powder, saponin powder, silkworm sand, and sapindus powder.
  • the penetrant may be at least one selected from the group consisting of silicone polyoxyethylene ether, alkylaryl sulfonate, alcohol ether succinate, and phenol ether succinate.
  • auxiliaries may be added to the fungicide composition according to the present invention as appropriate.
  • the addition amount of the other auxiliary agents may be an acceptable amount in agricultural fungicides.
  • the other auxiliary agent may be selected from at least one of a disintegrant, an antifoaming agent, an antifreezing agent, and a thickener.
  • the disintegrant is selected from at least one of bentonite, urea, ammonium sulfate, aluminum chloride, and glucose.
  • the antifoaming agent is at least one selected from the group consisting of silicone oil, silicone compounds, C10-C20 saturated fatty acid compounds, and C8-C10 fatty alcohol compounds.
  • the antifreeze is selected from at least one of ethylene glycol, propylene glycol, glycerol, and polyethylene glycol.
  • the thickener is selected from at least one of xanthan gum, polyvinyl alcohol, and polyethylene glycol.
  • the fungicide composition prepared by the present invention may be added with corresponding ingredients according to methods known to those skilled in the art to prepare wettable powders, powders, granules, concentrated emulsions, emulsifiable concentrates, suspensions, aerosols or Aerosol and other dosage forms.
  • an effective amount of the fungicide composition of the present invention can be applied according to different crops and diseases, and can be implemented by foliar spraying, seed treatment or soil treatment.
  • the invention also protects a composition containing at least two active ingredients.
  • the active composition of the composition includes a phosphonium salt compound (a compound represented by Formula I) and at least one other active compound.
  • the other active compound may be at least one of known fungicides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners, and chemical pheromones, and more preferably bactericidal Agents and pesticides.
  • the composition is a bactericidal composition, which refers to a composition prepared by a compound represented by Formula I and one or more other bactericides and a preparation thereof, which are used to expand the scope of product control.
  • the other fungicides include: 2- (thiocyanomethylthio) benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, azoxystrobin, amisole, antimycin, and powdery parasitic spores , Azaconazole, azoxystrobin, Bacillus subtilis, benomyl, benzylcarb, fenthiapyr, benfifluconazole, biphenyl, thiacumid, biphenyltriazole, biphenylpyridine Myclosporin, blasticidin-S, borax, Bordeaux solution, boscalid, furfurazol, butanil sulfonate, dicarbendazim, carbendazim, carbendazim, verrudin
  • the composition is a bactericidal and insecticidal composition, which refers to a composition prepared by a compound represented by Formula I and one or more other pesticides and a preparation thereof, which are used to expand the scope of product control.
  • the other insecticides include: Avermectin, Acephate, Acetamiprid, Housefly Phosphorus, Acetonitrile, Pyrethrin, Cotton Lingwei, Aldicarb, Aldicarb, Acrymethrin , Aloxin, dichlorcarb, alpha-cypermethrin, alpha-ecdysone, endosulfan, thiothion, fendicarb, amine phosphate, sothothion, bismetham, pseudoequiline, beta Dimethophos, Azadirachtin, Pyridoxine, Pamphosphos, Azinphos-methyl, Azophos, Permethrin, Cephalcarb, Promethazol, Pesticide,
  • the compound of the formula I provided by the present invention has a broad spectrum and excellent bactericidal activity, and can be used to prevent and control a variety of crops caused by fungi of the four classes of ascomycetes, ascomycetes, basidiomycetes, and oomycetes. Disease. Good control results can be obtained at very low doses.
  • the compounds of the formula I have a certain systemic property and can be used as foliar and soil fungicides to prevent and cure diseases on many crops.
  • the following diseases can be controlled: pepper blight, tomato early blight, tomato late blight, tomato gray mold, rice blast, wheat leaf spot, apple rot, rice sheath blight, rice blast, rice blast disease, Rice blight, wheat powdery mildew, wheat scab, rape sclerotinia, cucumber downy mildew, cucumber wilt, cucumber gray mold, cucumber powdery mildew, apple powdery mildew, watermelon anthracnose, peanut brown spot, Melon fruit rot, cotton fusarium wilt, cotton verticillium wilt, and cotton blight.
  • FIG. 1 is a flow chart for the preparation of a compound represented by Formula I.
  • the compounds numbered Ia 4-11 a-81 to Ia 4-11 b-81 to Ia 4-11 a-184 to Ia 4-11 b-184 were all prepared according to the method in Example 1; numbered Ia 4-11
  • the compounds of a-185 to Ia 4-11 b-185 to Ia 4-11 a-553 to Ia 4-11 b-553 were all prepared by referring to the methods in Examples 1 and 2.
  • composition containing the compound represented by the formula I is as follows: (the following components are based on mass percentage content, the active component is metered after adding 100%)
  • Composition of wettable powder 50% of the compound of formula I, 5% of dispersant polycarboxylate, 3% of sodium dodecyl wetting agent, 42% of solid carrier or disintegrant bentonite; The proportions are mixed to obtain a mixture, which is subjected to jet milling to obtain a 50% wettable powder.
  • Composition of emulsifiable concentrate 30% of the compound represented by Formula I, 12% of an emulsifier polyoxyalkylene alkylaryl ether, 10% of an alkylaryl sulfonate sulphonate, and 48% of cyclohexanone as a liquid carrier. The ratios were mixed to obtain a clear solution of 30% of the compound.
  • composition of water-dispersible granules 70% of the compound represented by Formula I, 3% calcium alkylbenzene sulfonate as dispersant, 3% lignin sulfonate as dispersant, 4% sodium dodecyl sulfate as wetting agent, and solid Carrier or filler starch 20%; 70% water-dispersible granules of the compound of formula I are prepared by mixing the components according to the ratio.
  • Example 8 Determination of bactericidal activity:
  • the compounds of formula I of the present invention are used to test various bacterial diseases in plants.
  • the test methods are as follows:
  • the diameter of each treated colony is measured by the cross method, and the colony growth diameter is calculated using formula (1), and the average value is taken.
  • Colony growth diameter colony diameter-bacteria cake diameter
  • the growth inhibitory rate of each compound against the pathogenic bacteria was calculated from the blank control colony growth diameter and the treated colony growth diameter, see formula (2) below.
  • Mycelial growth inhibition rate (%) (control colony growth diameter-chemical treatment colony growth diameter) / control colony growth diameter ⁇ 100 (2)
  • the triphenylphosphonium salt compound represented by the formula I provided by the present invention has a broad spectrum and excellent bactericidal activity, and can be used to control four broadly pathogenic fungi in various crops: ascomycetes, basidiomycetes, semi-strains, and eggs. Diseases caused by mycobacterial diseases. Good control effects can be obtained at low doses, and they are widely used in plant protection agents.

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Abstract

L'invention concerne un composé de sel de triphényl-phosphonium quaternaire, son procédé de préparation et son application. Le composé adopte la structure de la formule I. Le procédé de préparation met en œuvre une réaction nucléophile du composé de formule VII et une triphényl-phosphine dans un solvant organique avec ou sans catalyseur afin d'obtenir le composé de formule I, lequel sert à prévenir et traiter des maladies causées par une pluralité de germes, notamment des ovomycètes, des basidiomycètes, des ascomycètes et des champignons mi-connus présents sur une variété de plantes. Son application sur l'oïdium, la rouille du maïs, l'anthracnose du melon et analogues est concluante tout en assurant une lutte efficace à faible dosage.
PCT/CN2018/100964 2018-08-17 2018-08-17 Composé de sel de triphényl-phosphonium quaternaire, son procédé de préparation et son application WO2020034181A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU2018436544A AU2018436544B2 (en) 2018-08-17 2018-08-17 Quaternary triphenylphosphonium salt compound, preparation method therefor, and uses thereof
CA3101114A CA3101114C (fr) 2018-08-17 2018-08-17 Composes de sel de triphenylphosphonium, leur procede de production et leur utilisation
PCT/CN2018/100964 WO2020034181A1 (fr) 2018-08-17 2018-08-17 Composé de sel de triphényl-phosphonium quaternaire, son procédé de préparation et son application

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PCT/CN2018/100964 WO2020034181A1 (fr) 2018-08-17 2018-08-17 Composé de sel de triphényl-phosphonium quaternaire, son procédé de préparation et son application

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WO2009047240A1 (fr) * 2007-10-09 2009-04-16 Smithkline Beecham Corporation Dérivés d'indole utiles comme activateurs de ppar
CN102757459A (zh) * 2011-04-29 2012-10-31 上海源力生物技术有限公司 用于合成前列腺素类药物的中间体及其制备方法
WO2013172979A1 (fr) * 2012-05-14 2013-11-21 University Of Southern California Procédés et compositions destinés à l'imagerie de perfusion myocardique par tomographie par émission de positons
CN107226791A (zh) * 2017-06-13 2017-10-03 贵州医科大学 氮氧化物作为新型组蛋白去乙酰化酶抑制剂的抗肿瘤应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009047240A1 (fr) * 2007-10-09 2009-04-16 Smithkline Beecham Corporation Dérivés d'indole utiles comme activateurs de ppar
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