51276-47-2

Usage

Enzyme inhibitor

This dephospho transition-state analogue (FW = 177.10 g/mol; CAS 51276- 47-2) is naturally occurring glutamate analogue, first isolated from Streptomyces viridochromogenes. Phosphonothricin is a slow, tight-binding inhibitor of glutamine synthetase that binds at the glutamate binding site and stabilizes the flap of a glutamyl residue in a position blocking glutamate entry into the active site, thereby trapping the inhibitor on the enzyme. Phosphinothricin undergoes an ATP-dependent phosphorylation. Note: Phosphinothricin is a component of the antibiotics bialaphos and phosalacine. The monoammonium salt of the racemic compound, also called glufosinate-ammonium, is a post-emergent herbicide.

Metabolic pathway

When 14C-phosphinothricin [homoalanin-4-yl- (methyl)phosphinic acid] is incubated in the cell suspension cultures of soybean, wheat, and maize, in maize cells which take up to 50% of the applied radioactivity, four different metabolites are detected which are identified as 4-methylphosphinico-2-oxo- butyric acid, 4-methylphosphinico-2-hydroxybutyric acid, 4-methylphosphinicobutyric acid, and 3- methylphosphinicopropionic acid. In soybean and wheat cultures, 10 and 6% of the applied radioactivity is taken up, respectively. In soybean, only one metabolite, 3-methylphosphinicopropionic acid, is detected, whereas in wheat, 4-methyl- phosphinicobutyric acid is additionally present.

InChI:InChI=1/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)

Upstream product

• 74-90-8 hydrogen cyanide 
• 59374-45-7 (3,3-Dimethoxy-propyl)-methyl-phosphinic acid ethyl ester 
• 15715-41-0 methyldiethoxyphosphine 
• 73385-92-9 ethyl methyl-(3,3-diethoxypropyl)phosphinate 
• 151-50-8 potassium cyanide 
• 36120-72-6 methyl-vinyl-phosphinic acid 2-chloro-ethyl ester 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 40682-54-0 ethyl N-benzylideneglycinate 
• 63314-88-5 vinylmethylphosphinic acid methyl ester 
• 139574-94-0 methyl 2-(benzylideneamino)-4-(methoxymethylphosphinyl)butyrate 
• 139574-95-1 2-{[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-amino}-4-(methoxy-methyl-phosphinoyl)-butyric acid methyl ester 
• 139575-01-2 2-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-4-(methoxy-methyl-phosphinoyl)-butyric acid methyl ester 
• 87647-63-0 4-(Methoxy-methyl-phosphinoyl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid ethyl ester 
• 109541-73-3 METHYL DL-2-(1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)-4-(ETHOXYMETHYLPHOSPHINYL)BUTANOATE 

Downstream Products

• 77182-82-2 2-amino-4-(hydroxymethylphosphinyl)butyric acid monoammonium salt 
• 82785-28-2 4-[hydroxy(methyl)phosphonyl]-DL-homoalanine 
• 15090-23-0 2-carboxyethyl-methyl-phosphinic acid 
• 79778-02-2 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid 
• 35597-44-5 L-phosphinothricin 
• 328-50-7 α-ketoglutaric acid 
• 77182-82-2 ammonium glufosinate 

Relevant academic research and scientific papers

Preparation method of glufosinate-ammonium

The invention discloses a preparation method of glufosinate-ammonium. The preparation method comprises the following steps that 1, in alkaline environment, 4-(hydroxymethyl phosphono)-2-carbonyl butyric acid (I) and a benzylamine solution react to produce 2-[( phenyl amino)-4-(methyl sodium phosphate)-sodium butyrate (II); 2, 2-[(phenyl amino)-4-(methyl sodium phosphate)-sodium butyrate (II) is subjected to acid hydrolysis to obtain glufosinate-ammonium (III). Compared with the prior art, the preparation method has the advantages that the conditions are mild; the yield of the glufosinate-ammonium is high; the purity is high.

Glufosinate ammonium preparation method

The invention relates to a glufosinate ammonium preparation method. According to the present invention, nitro is introduced by using a simple and economical method, and is reduced under a mild condition so as to introduce amino group as the key step, such that the method for introducing amino by using other expensive amino acid derivatives or other toxic nitrogen-containing compounds is avoided, and the amino protection and deprotection during the reaction is eliminated; and the preparation method has advantages of simple reaction process, mild condition, simple and easily-available raw materials, simple operation and good atom economy, and is extremely suitable for industrial production.

Process for preparing glufosinate acid with hydrogenation method

The invention discloses a process for preparing precursor glufosinate acid of glufosinate acid with a catalytic hydrogenation method. The process comprises the following steps: firstly, reacting N-ethyl acetamidomalonate with 2-[ethyoxyl(methyl)phosphonyl] acetaldehyde under the actions of an acid binding agent and a dehydrating agent to generate an intermediate, namely, 2-acetamido-4-[ethyoxyl(methyl)phosphonyl]butyl-2-olefine acid ester; secondly, separating and purifying the intermediate, performing hydrogenation by taking ethanol as a solvent under the catalytic action of a hydrogenation catalyst to obtain a product, namely, 2-acetamido-4-[ethyoxyl(methyl)phosphonyl]ethyl butyrate, wherein the two-step yield can be 85 percent or more; lastly, performing deprotection with concentrated hydrochloric acid, and removing the hydrochloric acid to obtain the glufosinate acid. The process has the advantages of easiness in reaction and post-treatment operation, high yield, recyclability of the hydrogenation catalyst and the like, and has a very wide industrial prospect.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

A aminonitrile preparation method and process for the preparation of the intermediates of glufosinate

The invention discloses a preparation method of amino-nitrile and an intermediate for preparing glufosinate-ammonium. The preparation method disclosed by the invention aims at solving the problem of low glufosinate-ammonium yield by using acetal in the existing methods. Different from the existing methods for preparing glufosinate-ammonium, the method disclosed by the invention comprises the following steps: firstly reacting acetal with acetylchloride to obtain an enol ether intermediate, reacting the enol ether intermediate with sodium cyanide to obtain amino-nitrile, and finally hydrolyzing the amino-nitrile to obtain the glufosinate-ammonium. The method has the advantages of higher reaction yield and capacity of remarkably reducing the production cost of the glufosinate-ammonium.

LJ reaction in the preparation wittich reagent and application of glufosinate in

The present invention relates to an application of a new LJ intramolecular isomerization reaction in preparation of a wittig reagent and a herbicide of glufosinate-ammonium. With the application, a new approach of a synthesis route for preparing the wittig reagent and the glufosinate-ammonium is developed, the disadvantages of the existing wittig reaction are improved, and the industrial design of the glufosinate-ammonium production is improved.

The purification process of a grass ammonium phosphine

The invention provides a glufosinate purifying technology including the following steps: (1) adding glufosinate hydrochloride to alcohol R1OH, adding R2NH2 for ammoniation, adjusting the pH to 7.0-14.0, cooling and filtering, removing a solvent from a filtrate to obtain glufosinate ammonium salt and a small amount of organic impurities; (2) dissolving the glufosinate ammonium salt obtained by the steps (1) in an appropriate amount of water, leading in CO2 for neutralizing to the pH of 2.0-5.0, adding a proper amount of alcohol R3OH for precipitation of glufosinate acid, centrifugally filtrating to obtain the glufosinate acid which contains a small amount of ammonium hydrogen carbonate or organic amine carbonates; (3) heating for drying a glufosinate acid filtering cake obtained by the step (2) for decomposition and volatilization of the ammonium hydrogen carbonate or organic amine carbonates to obtain high purity glufosinate acid. The glufosinate purifying technology is simple in steps, the obtained glufosinate is low in inorganic salt content and high in purity, and compared with a traditional technology using epoxy ethane and epoxy propane, the purifying technology using carbon dioxide for separation of glufosinate hydrochloride and HCl is more economical, and high in safety, and has a higher industrialization prospect.

Method for preparing high-purity glufosinate-ammonium by organic alkali process

The invention discloses a method for preparing high-purity glufosinate-ammonium by an organic alkali process. The method comprises the following steps: by using a glufosinate-ammonium hydrochloride solution as a raw material, filtering the raw material, concentrating, directly adding tertiary amine R1R2R3N1 into the concentrated solution under the heating condition of 60-80 DEG C, and keeping the temperature to carry out hydrochloric acid removal reaction; after the reaction finishes, cooling to -3 to -8 DEG C to precipitate a glufosinate-ammonium free acid crude product; adding alcohol into the crude product, pulping, and filtering, wherein the obtained filter cake is glufosinate-ammonium free acid; adding alcohol into the glufosinate-ammonium free acid, heating to 30-50 DEG C, introducing ammonia gas to react; and after the reaction finishes, cooling to crystallize, filtering, and drying to obtain the glufosinate-ammonium with the purity of at least 88%.

Purification method for glufosinate-ammonium

The invention relates to a purification method for glufosinate-ammonium. The method comprises the following steps that a glufosinate-ammonium hydrochloride crude product is dissolved into a solvent, then, alkaline is added to be subjected to a reaction, the pH value is adjusted to be 7-10, reduced pressure distillation is performed to remove some solvent, then filtering is performed to remove ammonium chloride and other undissolved substances; acid is added into the reaction solution to be subjected to a reaction, the pH value is adjusted to be 1-4.5, and then filtering and drying are performed to obtain glufosinate-ammonium acid; the glufosinate-ammonium acid is dissolved into the solvent, then, ammonia gas is introduced to be subjected to a salt forming reaction, glufosinate-ammonium solid is separated out, and filtering and drying are performed to obtain high-purity glufosinate-ammonium. According to the purification technology, fatty amine hard to remove and high-risk ethylene oxide and epoxypropane are prevented from being used, the steps are simple, the obtained glufosinate-ammonium is low in inorganic salt content and high in purity, yield and safety, water or alcohol is used as the solvent in the technological process, ammonium hydroxide and inorganic base are used for being subjected to a neutral reaction, the glufosinate-ammonium conforms to the environment-friendly and economical principle, and the good industrial prospect is achieved.

A glufosinate hydrochloride by the method of preparation grass ammonium phosphine acid (by machine translation)

The present invention discloses a one-glufosinate hydrochloride by the method of preparation grass ammonium phosphine acid, firstly the glufosinate hydrochloric acid salt is dissolved in the alcohol, then adding ammonia in and after the, precipitated grass ammonium phosphine acid. The method of the invention not only can be obtained in high yield high-purity grass ammonium phosphine acid, but also can save a large amount of water and alcohol, is suitable for industrial application. (by machine translation)