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AR132932A1 - SYNTHESIS OF GLUFOSINATE BY AN AMIDASE-BASED PROCESS - Google Patents

SYNTHESIS OF GLUFOSINATE BY AN AMIDASE-BASED PROCESS

Info

Publication number
AR132932A1
AR132932A1 ARP240101485A ARP240101485A AR132932A1 AR 132932 A1 AR132932 A1 AR 132932A1 AR P240101485 A ARP240101485 A AR P240101485A AR P240101485 A ARP240101485 A AR P240101485A AR 132932 A1 AR132932 A1 AR 132932A1
Authority
AR
Argentina
Prior art keywords
alkyl
glufosinate
carbamoyl
ethyl
formula
Prior art date
Application number
ARP240101485A
Other languages
Spanish (es)
Inventor
Gunther Zimmermann
Moritz Stefan Pott
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of AR132932A1 publication Critical patent/AR132932A1/en

Links

Classifications

    • 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
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
    • C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Un método para preparar glufosinato, que comprende las etapas de hidrolizar una N-carbamoil glufosinato amida con una enzima amidasa para formar un compuesto de N-carbamoil aminoácido seguido de la escisión de la porción carbamoílo de dicho compuesto de N-carbamoil aminoácido. Reivindicación 1: Un método para preparar glufosinato y/o una sal de este o un alquiléster de glufosinato y/o una sal de este, caracterizado porque el glufosinato o el alquiléster de glufosinato tiene una estructura molecular de acuerdo con la fórmula (1), en donde R es H o C₁-C₈ alquilo, preferentemente, H o C₁-C₆ alquilo, con mayor preferencia, H o C₂-C₄ alquilo, aun con mayor preferencia, etilo o butilo y con máxima preferencia, etilo, en donde el proceso comprende las siguientes etapas: a) hidrolizar una N-carbamoil glufosinato amida que tiene la fórmula (2), en donde R es H o C₁-C₈ alquilo, preferentemente, H o C₁-C₆ alquilo, con mayor preferencia, H o C₂-C₄ alquilo, aun con mayor preferencia, etilo o butilo y con máxima preferencia, etilo, mediante una enzima amidasa, preferentemente seleccionada de la lista que consiste en peptidasas, proteasas, amidasas lineales o amidasas cíclicas, para obtener un N-carbamoil aminoácido que tiene la fórmula (3), en donde R es H o C₁-C₈ alquilo, preferentemente, H o C₁-C₆ alquilo, con mayor preferencia, H o C₂-C₄ alquilo, aun con mayor preferencia, etilo o butilo y con máxima preferencia, etilo, y b) escindir la porción carbamoílo del N-carbamoil aminoácido que tiene la fórmula (3). Reivindicación 13: Una composición caracterizada porque comprende una N-carbamoil glufosinato amida que tiene la fórmula (2), en donde R es H o C₁-C₈ alquilo, preferentemente, H o C₁-C₆ alquilo, con mayor preferencia, H o C₂-C₄ alquilo, aun con mayor preferencia, etilo o butilo y con máxima preferencia, etilo.A method for preparing glufosinate, comprising the steps of hydrolyzing an N-carbamoyl glufosinate amide with an amidase enzyme to form an N-carbamoyl amino acid compound followed by cleavage of the carbamoyl portion of said N-carbamoyl amino acid compound. Claim 1: A method for preparing glufosinate and/or a salt thereof or a glufosinate alkyl ester and/or a salt thereof, characterized in that the glufosinate or the glufosinate alkyl ester has a molecular structure according to formula (1), wherein R is H or C₁-C₈ alkyl, preferably H or C₁-C₆ alkyl, more preferably H or C₂-C₄ alkyl, even more preferably ethyl or butyl and most preferably ethyl, wherein the process comprises the following steps: a) hydrolyzing an N-carbamoyl glufosinate amide having formula (2), wherein R is H or C₁-C₈ alkyl, preferably H or C₁-C₆ alkyl, more preferably H or C₂-C₄ alkyl, even more preferably, ethyl or butyl and most preferably ethyl, by an amidase enzyme, preferably selected from the list consisting of peptidases, proteases, linear amidases or cyclic amidases, to obtain an N-carbamoyl amino acid having the formula (3), wherein R is H or C1-C2 alkyl, preferably H or C1-C6 alkyl, more preferably H or C2-C4 alkyl, even more preferably ethyl or butyl and most preferably ethyl, and b) cleaving the carbamoyl portion of the N-carbamoyl amino acid having the formula (3). Claim 13: A composition characterized in that it comprises an N-carbamoyl glufosinate amide having the formula (2), wherein R is H or C₁-C₈ alkyl, preferably, H or C₁-C₆ alkyl, more preferably, H or C₂-C₄ alkyl, even more preferably, ethyl or butyl and most preferably, ethyl.

ARP240101485A 2023-06-13 2024-06-11 SYNTHESIS OF GLUFOSINATE BY AN AMIDASE-BASED PROCESS AR132932A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP23179058 2023-06-13

Publications (1)

Publication Number Publication Date
AR132932A1 true AR132932A1 (en) 2025-08-13

Family

ID=86776424

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP240101485A AR132932A1 (en) 2023-06-13 2024-06-11 SYNTHESIS OF GLUFOSINATE BY AN AMIDASE-BASED PROCESS

Country Status (4)

Country Link
CN (1) CN121335908A (en)
AR (1) AR132932A1 (en)
TW (1) TW202512923A (en)
WO (1) WO2024256370A1 (en)

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3047024A1 (en) 1978-11-11 1982-07-22 Hoechst Ag, 6000 Frankfurt Phosphorus-contg. cyanohydrin deriv. prepn. - by reacting phosphinate ester with cyanohydrin deriv. e.g. (meth)acrolein cyanohydrin
DE2849003A1 (en) 1978-11-11 1980-08-21 Hoechst Ag CYANHYDRINE DERIVATIVES CONTAINING PHOSPHORUS AND METHOD FOR THE PRODUCTION THEREOF
DE3319850C2 (en) 1983-06-01 1985-05-09 Hoechst Ag, 6230 Frankfurt Process for the preparation of phosphorus-containing cyanohydrin derivatives
AU599985B2 (en) 1986-06-09 1990-08-02 Meiji Seika Kaisha Ltd. New process for the production of L-2-amino-4- (hydroxymethyl-phosphinyl)-butyric acid
DE3920570A1 (en) 1989-06-23 1991-01-03 Hoechst Ag Recovery of L-2-amino-4-methyl-phosphino-butyric acid - from prod. of enzymatic trans;amination of 4-(hydroxy)(methyl) phosphinyl-2-oxo:butyric acid by stepwise acid and pptn.
DE4407197A1 (en) 1994-03-04 1995-09-07 Hoechst Schering Agrevo Gmbh Process for the preparation of / L / -Homoalanin-4-yl- (methyl) phosphinic acid and its salts by resolution
DE19736125A1 (en) 1997-08-20 1999-02-25 Hoechst Schering Agrevo Gmbh Preparation of phosphinyl-butyric acid derivatives
DE19848129A1 (en) 1998-10-19 2000-04-20 Basf Ag New nucleic acid sequence encoding Alcaligenes faecalis nitrilase polypeptide useful for converting racemic nitriles to chiral carboxylic acids
CN100445391C (en) 2002-12-02 2008-12-24 巴斯福股份公司 L-rhamnose-inducible expression system
US9255115B2 (en) 2011-09-30 2016-02-09 Meiji Seika Pharma Co. Ltd. Method for producing glufosinate P free acid
CN102372739B (en) 2011-12-05 2017-06-16 河北威远生化农药有限公司 A kind of synthetic method of glufosinate-ammonium
CN102399240A (en) 2011-12-27 2012-04-04 江苏优士化学有限公司 Improved synthesis method of glufosinate-ammonium and analogue
EP3143030B1 (en) 2014-05-13 2019-07-17 Basf Se Method for the preparation of cyanohydrins containing phosphorus

Also Published As

Publication number Publication date
CN121335908A (en) 2026-01-13
WO2024256370A1 (en) 2024-12-19
TW202512923A (en) 2025-04-01

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