AR127934A1 - Síntesis de glufosinato mediante el uso de un proceso basado en hidantoinasa - Google Patents
Síntesis de glufosinato mediante el uso de un proceso basado en hidantoinasaInfo
- Publication number
- AR127934A1 AR127934A1 ARP220103397A ARP220103397A AR127934A1 AR 127934 A1 AR127934 A1 AR 127934A1 AR P220103397 A ARP220103397 A AR P220103397A AR P220103397 A ARP220103397 A AR P220103397A AR 127934 A1 AR127934 A1 AR 127934A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- glufosinate
- salts
- c8alkyl
- amino acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 6
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 title abstract 5
- 239000005561 Glufosinate Substances 0.000 title abstract 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 8
- -1 N-carbamoyl amino Chemical group 0.000 abstract 7
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 abstract 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract 5
- 229940091173 hydantoin Drugs 0.000 abstract 5
- 125000005907 alkyl ester group Chemical group 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 238000003776 cleavage reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 108091022884 dihydropyrimidinase Proteins 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 230000007017 scission Effects 0.000 abstract 2
- IAJOBQBIJHVGMQ-SCSAIBSYSA-N (2R)-glufosinate Chemical compound C[P@@](O)(=O)CC[C@@H](N)C(O)=O IAJOBQBIJHVGMQ-SCSAIBSYSA-N 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
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- 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
-
- 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
- A01N43/24—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 two or more hetero atoms
- A01N43/26—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 two or more hetero atoms five-membered rings
- A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
-
- 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
-
- 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
- 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
-
- 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)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Un método para elaborar glufosinato, que comprende las etapas de hidrolizar una hidantoína con una enzima hidantoinasa para formar un compuesto de aminoácido de N-carbamoilo seguida de escisión de la porción de carbamoilo de dicho compuesto de aminoácido de N-carbamoilo. Reivindicación 1: Un método para elaborar glufosinato, su éster de alquilo o las sales de este caracterizado porque tienen la fórmula (3), en donde R es H o C₁-C₈alquilo, que comprende las etapas de: a) hidrolizar una hidantoína que tiene la fórmula (1), en donde R es H o C₁-C₈alquilo, mediante una enzima hidantoinasa para formar un aminoácido de N-carbamoilo que tiene la fórmula (2), en donde R es H o C₁-C₈alquilo, y b) escindir la porción de carbamoilo del aminoácido de N-carbamoilo que tiene la fórmula (2). Reivindicación 2: El método de acuerdo con la reivindicación 1, caracterizado porque la etapa de escisión b) proporciona glufosinato, su éster de alquilo o las sales de este que tiene la fórmula (3), en donde R es H o C₁-C₈alquilo, preferentemente, H o C₁-C₆alquilo, con mayor preferencia, H o C₂-C₄alquilo, incluso con mayor preferencia, etilo o butilo y, en particular, etilo. Reivindicación 4: El método de acuerdo con cualquiera de las reivindicaciones 1 a 3, caracterizado porque al menos 40%, preferentemente, al menos 50% y, en particular, al menos 70%, de la hidantoína que tiene la fórmula (1) se convierte en L-glufosinato, su éster de alquilo o las sales de este que tienen la fórmula (3a), en donde la fórmula (3a) es como se define en la reivindicación 3. Reivindicación 7: El método de acuerdo con cualquiera de las reivindicaciones 1 a 6, caracterizado porque la etapa de hidrólisis a) se realiza a un pH de 6 a 11, preferentemente, de 6,5 a 10, con mayor preferencia, de 7 a 9,5 y, en particular, de 7,5 a 9 y/o a una temperatura de 20 a 50ºC, preferentemente, de 25 a 45ºC, con mayor preferencia, de 30 a 42ºC y, en particular, de 32 a 40ºC. Reivindicación 15: Una composición caracterizada porque comprende una hidantoína que tiene la fórmula (1b), en donde R es H o C₁-C₈alquilo, un aminoácido de N-carbamoilo que tiene la fórmula (2a), en donde R es H o C₁-C₈alquilo y L-glufosinato o las sales de este. Reivindicación 16: La composición de acuerdo con la reivindicación 15, caracterizada porque la cantidad de L-glufosinato o las sales de este son de al menos 40% en peso, preferentemente, al menos 50% en peso y, en particular, al menos 70% en peso, en función de la cantidad total de la hidantoína que tiene la fórmula (1b), el aminoácido de N-carbamoilo que tiene la fórmula (2a) y L-glufosinato o las sales de este. Reivindicación 18: Un método para controlar malezas selectivamente en un área, preferentemente, caracterizado porque contiene un cultivo de semillas plantadas o cultivos que son resistentes a glufosinato, que comprende: aplicar al área una cantidad eficaz de una composición que comprende L-glufosinato o las sales de este en una proporción enantiomérica de al menos 50%, preferentemente, en un exceso enantiomérico mayor de 70%, sobre D-glufosinato o las sales de este y más de 0,01% en peso a menos de 10% en peso, en función de la cantidad total de la composición, de un aminoácido de N-carbamoilo que tiene la fórmula (2), en donde R es H o C₁-C₈alquilo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21213750 | 2021-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR127934A1 true AR127934A1 (es) | 2024-03-13 |
Family
ID=79170944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP220103397A AR127934A1 (es) | 2021-12-10 | 2022-12-12 | Síntesis de glufosinato mediante el uso de un proceso basado en hidantoinasa |
Country Status (8)
| Country | Link |
|---|---|
| KR (1) | KR20240121809A (es) |
| CN (1) | CN118369324A (es) |
| AR (1) | AR127934A1 (es) |
| AU (1) | AU2022405733A1 (es) |
| CA (1) | CA3240053A1 (es) |
| IL (1) | IL313405A (es) |
| MX (1) | MX2024007018A (es) |
| WO (1) | WO2023105080A1 (es) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3142036A1 (de) | 1981-10-23 | 1983-05-05 | Hoechst Ag, 6230 Frankfurt | Phosphorhaltige hydantoine, verfahren zu deren herstellung und ihre verwendung |
| 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 (de) | 1989-06-23 | 1991-01-03 | Hoechst Ag | Verfahren zur isolierung von l-2-amino-4-methylphosphinobuttersaeure-ammoniumsalz aus einer enzymatischen transaminierungsloesung |
| DE4407197A1 (de) | 1994-03-04 | 1995-09-07 | Hoechst Schering Agrevo Gmbh | Verfahren zur Herstellung von /L/-Homoalanin-4-yl-(methyl)phosphinsäure und deren Salze durch Racematspaltung |
| DE19848129A1 (de) | 1998-10-19 | 2000-04-20 | Basf Ag | Verfahren zur Herstellung chiraler Carbonsäuren aus Nitrilen mit Hilfe einer Nitrilase oder Mikroorganismen, die ein Gen für die Nitrilase enthalten |
| AU2003288189B8 (en) | 2002-12-02 | 2009-06-25 | Basf Aktiengesellschaft | L-rhamnose-inducible expression systems |
| EP2762484A4 (en) | 2011-09-30 | 2015-05-06 | Meiji Seika Pharma Co Ltd | PROCESS FOR PRODUCING FREE ACID GLUFOSINATE P |
| CN111662325B (zh) | 2019-03-05 | 2023-03-24 | 利尔化学股份有限公司 | 一种制备l-草铵膦的方法 |
| CN112574117B (zh) * | 2019-09-29 | 2022-09-20 | 利尔化学股份有限公司 | 一种草铵膦海因中间体及类似物的制备方法 |
| CN113045604B (zh) | 2021-04-13 | 2023-03-17 | 河北威远生物化工有限公司 | 一种草铵膦的合成方法 |
| CN113072579B (zh) * | 2021-04-13 | 2022-09-27 | 河北威远生物化工有限公司 | 一种草铵膦的制备方法 |
-
2022
- 2022-12-12 WO PCT/EP2022/085315 patent/WO2023105080A1/en active Application Filing
- 2022-12-12 AU AU2022405733A patent/AU2022405733A1/en active Pending
- 2022-12-12 CN CN202280080698.5A patent/CN118369324A/zh active Pending
- 2022-12-12 MX MX2024007018A patent/MX2024007018A/es unknown
- 2022-12-12 IL IL313405A patent/IL313405A/en unknown
- 2022-12-12 CA CA3240053A patent/CA3240053A1/en active Pending
- 2022-12-12 AR ARP220103397A patent/AR127934A1/es unknown
- 2022-12-12 KR KR1020247022736A patent/KR20240121809A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2022405733A1 (en) | 2024-06-20 |
| WO2023105080A1 (en) | 2023-06-15 |
| CA3240053A1 (en) | 2023-06-15 |
| CN118369324A (zh) | 2024-07-19 |
| KR20240121809A (ko) | 2024-08-09 |
| IL313405A (en) | 2024-08-01 |
| MX2024007018A (es) | 2024-06-19 |
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