CS235046B2 - Method of n-phosphonomethylglycine preparation - Google Patents

Method of n-phosphonomethylglycine preparation Download PDF

Info

Publication number: CS235046B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; phosphonomethylglycine; compound; diketopiperazine; molecular weight
Prior art date: 1982-07-29

Application number

CS835158A

Other languages

Czech (cs)

English (en)

Inventor

Rayman Y Wong

Nathan S Bunker

Original Assignee

Stauffer Chemical Co

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.)

1982-07-29

Filing date

1983-07-07

Publication date

1985-04-16

1983-07-07 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1985-04-16 Publication of CS235046B2 publication Critical patent/CS235046B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 24
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims description 7
-1 phosphorus compound Chemical class 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 10
239000011574 phosphorus Substances 0.000 claims abstract description 9
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
239000003795 chemical substances by application Substances 0.000 claims abstract description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
239000011707 mineral Substances 0.000 claims abstract description 7
BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 claims abstract description 7
239000002904 solvent Substances 0.000 claims abstract description 7
239000000376 reactant Substances 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
150000003839 salts Chemical group 0.000 claims description 11
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
239000012467 final product Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 9
230000003301 hydrolyzing effect Effects 0.000 abstract description 4
239000007795 chemical reaction product Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
239000000243 solution Substances 0.000 description 17
238000010992 reflux Methods 0.000 description 12
239000004009 herbicide Substances 0.000 description 11
230000002363 herbicidal effect Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
241000196324 Embryophyta Species 0.000 description 5
230000008635 plant growth Effects 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ROKAXOISGALEAP-UHFFFAOYSA-N [2,5-dioxo-4-(phosphonomethyl)piperazin-1-yl]methylphosphonic acid Chemical compound OP(O)(=O)CN1CC(=O)N(CP(O)(O)=O)CC1=O ROKAXOISGALEAP-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
230000012010 growth Effects 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical class CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
DGPSXMJBNDMVBE-UHFFFAOYSA-N OC(=O)CNC(F)(F)F Chemical class OC(=O)CNC(F)(F)F DGPSXMJBNDMVBE-UHFFFAOYSA-N 0.000 description 1
UNVGGERHRPPCFM-UHFFFAOYSA-N OP(=C)=O.NCC(O)=O Chemical compound OP(=C)=O.NCC(O)=O UNVGGERHRPPCFM-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000009835 boiling Methods 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
231100000357 carcinogen Toxicity 0.000 description 1
239000003183 carcinogenic agent Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000009306 commercial farming Methods 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1

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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
- 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
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CS835158A 1982-07-29 1983-07-07 Method of n-phosphonomethylglycine preparation CS235046B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/403,239 US4400330A (en)	1982-07-29	1982-07-29	Method for preparation of N-phosphonomethylglycine

Publications (1)

Publication Number	Publication Date
CS235046B2 true CS235046B2 (en)	1985-04-16

Family

ID=23595035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS835158A CS235046B2 (en)	1982-07-29	1983-07-07	Method of n-phosphonomethylglycine preparation

Country Status (18)

Country	Link
US (1)	US4400330A (da)
EP (1)	EP0102694B1 (da)
JP (1)	JPS5929698A (da)
KR (1)	KR840005460A (da)
AR (1)	AR231451A1 (da)
AT (1)	ATE29500T1 (da)
AU (1)	AU552195B2 (da)
BR (1)	BR8303922A (da)
CA (1)	CA1205486A (da)
CS (1)	CS235046B2 (da)
DD (1)	DD213220A5 (da)
DE (1)	DE3373479D1 (da)
DK (1)	DK299483A (da)
ES (1)	ES8500959A1 (da)
IL (1)	IL69096A0 (da)
PL (1)	PL140398B1 (da)
RO (1)	RO87040B (da)
ZA (1)	ZA834683B (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK467083A (da) *	1982-10-18	1984-04-19	Stauffer Chemical Co	Fremgangsmaade til fremstilling af n-phosphonomethylglycin
US4578224A (en) *	1982-10-18	1986-03-25	Stauffer Chemical Company	Method for preparation of salts of N-phosphonomethylglycine
CA1248531A (en) *	1984-04-17	1989-01-10	Jeffrey C. Watkins	4-substituted piperazine-2-carboxylic acids
US4694081A (en) *	1985-09-23	1987-09-15	Monsanto Company	Process to prepare 2,5-diketopiperazines
US4694082A (en) *	1985-09-23	1987-09-15	Monsanto Company	Compound 1,4-diisopropyl-2,5-diketopiperazine
US4804499A (en) *	1985-09-23	1989-02-14	Monsanto Company	Process for the preparation of N-substituted aminomethylphosphonic acids
US5352461A (en) *	1992-03-11	1994-10-04	Pharmaceutical Discovery Corporation	Self assembling diketopiperazine drug delivery system
CN1239473A (zh)	1997-02-13	1999-12-22	孟山都公司	制备氨基羧酸的方法
CA2339839A1 (en)	1998-08-12	2000-02-24	Monsanto Company	Continuous process for the preparation of n-(phosphonomethyl) iminodiacetic acid
BR112015000990B1 (pt)	2012-07-17	2020-04-28	Monsanto Technology Llc	Método para a síntese de um ácido aminoalquilenofosfônico ouseus ésteres fosfatos
WO2014012991A1 (en)	2012-07-17	2014-01-23	Straitmark Holding Ag	Method for the synthesis of n-(phosphonomethyl)glycine
RU2015103314A (ru) *	2012-07-17	2016-09-10	Страйтмарк Холдинг Аг	Способ синтеза N-фосфонометилиминодиуксусной кислоты
CN104812765B (zh)	2012-07-17	2017-06-06	斯特雷特马克控股股份公司	用于合成α‑氨基亚烷基膦酸的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2959590A (en) *		1960-11-08		Chz-chz
NL285361A (da) *	1961-11-13	1900-01-01
US3954761A (en) *	1968-10-17	1976-05-04	Petrolite Corporation	Piperazine phosphonic acids
RO65811A (fr) *	1974-06-26	1979-07-15	Budapesti Vegyimuevek	Procede pour obtenir du n-phosphonombethyl-glycine
DE2434312A1 (de) *	1974-07-17	1976-01-29	Bayer Ag	Heterocyclische phosphonsaeureester
DD123192A1 (da) *	1975-01-16	1976-12-05
US4053505A (en) *	1976-01-05	1977-10-11	Monsanto Company	Preparation of n-phosphonomethyl glycine

1982
- 1982-07-29 US US06/403,239 patent/US4400330A/en not_active Expired - Fee Related
1983
- 1983-06-21 CA CA000430889A patent/CA1205486A/en not_active Expired
- 1983-06-21 EP EP83303561A patent/EP0102694B1/en not_active Expired
- 1983-06-21 AT AT83303561T patent/ATE29500T1/de not_active IP Right Cessation
- 1983-06-21 DE DE8383303561T patent/DE3373479D1/de not_active Expired
- 1983-06-27 ZA ZA834683A patent/ZA834683B/xx unknown
- 1983-06-27 AU AU16277/83A patent/AU552195B2/en not_active Ceased
- 1983-06-28 IL IL69096A patent/IL69096A0/xx unknown
- 1983-06-28 JP JP58115299A patent/JPS5929698A/ja active Pending
- 1983-06-29 DK DK299483A patent/DK299483A/da not_active Application Discontinuation
- 1983-07-07 ES ES523938A patent/ES8500959A1/es not_active Expired
- 1983-07-07 CS CS835158A patent/CS235046B2/cs unknown
- 1983-07-08 AR AR293559A patent/AR231451A1/es active
- 1983-07-19 RO RO111668A patent/RO87040B/ro unknown
- 1983-07-22 BR BR8303922A patent/BR8303922A/pt unknown
- 1983-07-26 PL PL1983243175A patent/PL140398B1/pl unknown
- 1983-07-28 DD DD83253492A patent/DD213220A5/de unknown
- 1983-07-28 KR KR1019830003518A patent/KR840005460A/ko not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK299483D0 (da)	1983-06-29
ATE29500T1 (de)	1987-09-15
PL243175A1 (en)	1984-07-30
EP0102694B1 (en)	1987-09-09
DK299483A (da)	1984-01-30
DD213220A5 (de)	1984-09-05
BR8303922A (pt)	1984-04-24
ES523938A0 (es)	1984-11-01
AR231451A1 (es)	1984-11-30
US4400330A (en)	1983-08-23
ES8500959A1 (es)	1984-11-01
EP0102694A1 (en)	1984-03-14
KR840005460A (ko)	1984-11-12
JPS5929698A (ja)	1984-02-16
PL140398B1 (en)	1987-04-30
AU1627783A (en)	1984-02-02
IL69096A0 (en)	1983-10-31
RO87040A (ro)	1985-06-29
ZA834683B (en)	1985-02-27
AU552195B2 (en)	1986-05-22
RO87040B (ro)	1985-06-30
CA1205486A (en)	1986-06-03
DE3373479D1 (en)	1987-10-15

Publication	Publication Date	Title
US4547324A (en)	1985-10-15	Method for preparation of N-phosphonomethylglycine
US4168963A (en)	1979-09-25	Herbicidal agents
CS235046B2 (en)	1985-04-16	Method of n-phosphonomethylglycine preparation
SU682097A3 (ru)	1979-08-25	Гербицидное средство
CH646180A5 (de)	1984-11-15	Verfahren zur herstellung von n-phosphonomethyl-glycin.
HU176295B (en)	1981-01-28	Process for preparing n-perfluoro-acyl-n-phosphono-methyl-glycine derivatives and herbicide compositions contain
US4442041A (en)	1984-04-10	Method for preparation of N-phosphonomethylglycine
EP0098159B1 (en)	1986-09-03	Preparation of n-phosphonomethylglycine
US4428888A (en)	1984-01-31	Method for preparation of N-phosphonomethylglycine
US4415503A (en)	1983-11-15	Method for preparation of N-phosphonomethylglycine
US3316080A (en)	1967-04-25	Method for inhibiting growth of weeds and grasses
JP4391747B2 (ja)	2009-12-24	殺虫剤および害虫防除法
NO169288B (no)	1992-02-24	Fremgangsmaate for fremstilling av trimetylsulfoniumsaltetav n-fosfonometylglycin
US3305348A (en)	1967-02-21	Herbicidal composition and method employing diamino-s-triazine derivatives
US4605522A (en)	1986-08-12	Method for preparation of N-phosphonomethylglycine or salts
US4440695A (en)	1984-04-03	Method for preparation of N-phosphonomethylglycine
EP0107464B1 (en)	1986-01-08	Method for preparation of n-phosphonomethylglycine
CS241089B2 (en)	1986-03-13	Method of n-phosphonomethylglycine and its salts' production
SU1662997A1 (ru)	1991-07-15	Бутиловый эфир этил-1-(фениламино)циклогексилфосфиновой кислоты, про вл ющий гербицидную активность
KR790001258B1 (ko)	1979-09-18	2-[4-(5-할로겐치환 피리딜-2-옥시)페녹시]알칸카르복시산계 화합물의 제조방법
JPS6136485B2 (da)	1986-08-19
US3005695A (en)	1961-10-24	4-(2-chloro-4-fluoro-phenoxy)-butanoic acid and salts and esters thereof
JPH0149140B2 (da)	1989-10-23
CA1120747A (en)	1982-03-30	Herbicidal agents
JPS62108888A (ja)	1987-05-20	Ｎ−メチル−ｎ−ホスホノメチルヒドラジン誘導体、その製造方法及び該誘導体を有効成分とする除草剤