CS235988B2 - Method of n-phosphonomethylglycine organic salts preparation - Google Patents
Method of n-phosphonomethylglycine organic salts preparation Download PDFInfo
- Publication number
- CS235988B2 CS235988B2 CS838107A CS810783A CS235988B2 CS 235988 B2 CS235988 B2 CS 235988B2 CS 838107 A CS838107 A CS 838107A CS 810783 A CS810783 A CS 810783A CS 235988 B2 CS235988 B2 CS 235988B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- carbon atoms
- compound
- chloride
- phosphonomethylglycine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 229910052698 phosphorus Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011574 phosphorus Chemical group 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000005191 phase separation Methods 0.000 claims abstract description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract description 6
- 125000005537 sulfoxonium group Chemical group 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 abstract description 2
- 150000001805 chlorine compounds Chemical group 0.000 abstract description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 17
- 239000004009 herbicide Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- OWUGVJBQKGQQKJ-UHFFFAOYSA-M trimethylsulfanium;chloride Chemical compound [Cl-].C[S+](C)C OWUGVJBQKGQQKJ-UHFFFAOYSA-M 0.000 description 11
- -1 sulfoxonium halide Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 5
- 239000005648 plant growth regulator Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- DLFKJPZBBCZWOO-UHFFFAOYSA-N 8-methyl-n,n-bis(8-methylnonyl)nonan-1-amine Chemical compound CC(C)CCCCCCCN(CCCCCCCC(C)C)CCCCCCCC(C)C DLFKJPZBBCZWOO-UHFFFAOYSA-N 0.000 description 2
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- POYMFKJUYZDXAT-UHFFFAOYSA-N 1-(4-iodophenyl)pyrrolidine Chemical compound C1=CC(I)=CC=C1N1CCCC1 POYMFKJUYZDXAT-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- PDOGCHRAEBICEX-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical group OC(=O)COC1=CC=C(Cl)C=C1Cl.OC(=O)COC1=CC=C(Cl)C=C1Cl PDOGCHRAEBICEX-UHFFFAOYSA-N 0.000 description 1
- DFRHETNXRZJTGA-UHFFFAOYSA-N 2-(phosphanylmethylamino)acetic acid Chemical compound OC(=O)CNCP DFRHETNXRZJTGA-UHFFFAOYSA-N 0.000 description 1
- GVNLTKPENATPJA-UHFFFAOYSA-N 4-methylpentan-2-one;hydrochloride Chemical compound Cl.CC(C)CC(C)=O GVNLTKPENATPJA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000241413 Propolis Species 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
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229940069949 propolis Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000003799 water insoluble solvent Substances 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)]
-
- 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/457,812 US4431594A (en) | 1983-01-13 | 1983-01-13 | Method for preparation of salts of N-phosphonomethylglycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235988B2 true CS235988B2 (en) | 1985-05-15 |
Family
ID=23818168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS838107A CS235988B2 (en) | 1983-01-13 | 1983-11-03 | Method of n-phosphonomethylglycine organic salts preparation |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4431594A (en]) |
| EP (1) | EP0117337B1 (en]) |
| JP (1) | JPS59128396A (en]) |
| KR (1) | KR900003454B1 (en]) |
| AR (1) | AR246088A1 (en]) |
| AT (1) | ATE37030T1 (en]) |
| AU (1) | AU562827B2 (en]) |
| BG (2) | BG60165B2 (en]) |
| BR (1) | BR8306690A (en]) |
| CA (1) | CA1213903A (en]) |
| CS (1) | CS235988B2 (en]) |
| DD (1) | DD234273A5 (en]) |
| DE (1) | DE3377913D1 (en]) |
| DK (1) | DK167358B1 (en]) |
| ES (1) | ES8504693A1 (en]) |
| FI (1) | FI80045C (en]) |
| HU (1) | HU193534B (en]) |
| IL (1) | IL70036A (en]) |
| MX (1) | MX158972A (en]) |
| NO (1) | NO169288C (en]) |
| NZ (1) | NZ206020A (en]) |
| PL (1) | PL146421B1 (en]) |
| PT (1) | PT77710B (en]) |
| RO (1) | RO88471A (en]) |
| YU (1) | YU43199B (en]) |
| ZA (1) | ZA838049B (en]) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0376508U (en]) * | 1989-11-29 | 1991-07-31 | ||
| IL101539A (en) * | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Non-hygroscopic mono-ammonium salts of n-phosphonomethyl glycine derivatives their preparation and pesticidal compositons containing them |
| GB9111974D0 (en) * | 1991-06-04 | 1991-07-24 | Ici Plc | Novel process |
| GB9525956D0 (en) * | 1995-12-19 | 1996-02-21 | Zeneca Ltd | Manufacture of glyphosate salts |
| WO1999005914A1 (en) * | 1997-07-30 | 1999-02-11 | Monsanto Company | Process and compositions promoting biological effectiveness of exogenous chemical substances in plants |
| WO2000032045A1 (en) | 1998-11-30 | 2000-06-08 | Monsanto Technology Llc | Promoting biological effectiveness of exogenous chemical substances in plants |
| AUPR682201A0 (en) | 2001-08-03 | 2001-08-30 | Nufarm Limited | Glyphosate composition |
| MX2009008934A (es) * | 2007-02-26 | 2009-08-28 | Dow Agrosciences Llc | Proceso para la preparacion de algunas sulfiliminas sustituidas. |
| CA2726461C (en) | 2008-11-06 | 2016-02-16 | Sn Biotech Technologies Sp. Z O.O. Sp. K. | A liquid, homogenous herbicide composition, a method of weed control, a method of production of liquid, homogenous herbicide composition and use of a liquid, homogenous herbicide composition for weed control |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2271707A (en) * | 1937-06-24 | 1942-02-03 | Gen Aniline & Film Corp | Wetting agent |
| US2831019A (en) * | 1956-07-27 | 1958-04-15 | California Ink Company Inc | Method of preparing quaternary ammonium naphthenates |
| US4196143A (en) * | 1974-07-01 | 1980-04-01 | The Dow Chemical Company | Substituted phenoxyalkyl quaternary ammonium compounds |
| ES465139A1 (es) * | 1976-12-20 | 1978-10-01 | Monsanto Co | Un procedimiento para preparar una mono-o disal de n-fosfo- nometilglicina. |
| US4340761A (en) * | 1980-11-24 | 1982-07-20 | The Dow Chemical Company | Preparation of phosphonium phenoxide salts |
| US4315765A (en) * | 1980-12-04 | 1982-02-16 | Stauffer Chemical Company | Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides |
| US4341549A (en) * | 1981-08-24 | 1982-07-27 | Stauffer Chemical Company | Phosphonium salts of N-phosphonomethylglycine and their use as herbicides and plant growth regulants |
-
1983
- 1983-01-13 US US06/457,812 patent/US4431594A/en not_active Expired - Lifetime
- 1983-10-19 DE DE8383306353T patent/DE3377913D1/de not_active Expired
- 1983-10-19 AT AT83306353T patent/ATE37030T1/de not_active IP Right Cessation
- 1983-10-19 EP EP83306353A patent/EP0117337B1/en not_active Expired
- 1983-10-20 NZ NZ206020A patent/NZ206020A/en unknown
- 1983-10-20 NO NO833828A patent/NO169288C/no not_active IP Right Cessation
- 1983-10-24 FI FI833872A patent/FI80045C/fi not_active IP Right Cessation
- 1983-10-24 IL IL70036A patent/IL70036A/xx not_active IP Right Cessation
- 1983-10-25 AR AR83294638A patent/AR246088A1/es active
- 1983-10-26 DK DK491083A patent/DK167358B1/da not_active IP Right Cessation
- 1983-10-26 AU AU20587/83A patent/AU562827B2/en not_active Ceased
- 1983-10-28 ZA ZA838049A patent/ZA838049B/xx unknown
- 1983-10-28 CA CA000439925A patent/CA1213903A/en not_active Expired
- 1983-10-28 ES ES526880A patent/ES8504693A1/es not_active Expired
- 1983-10-31 HU HU833737A patent/HU193534B/hu not_active IP Right Cessation
- 1983-11-01 JP JP58203792A patent/JPS59128396A/ja active Granted
- 1983-11-01 RO RO83112457A patent/RO88471A/ro unknown
- 1983-11-03 CS CS838107A patent/CS235988B2/cs unknown
- 1983-11-09 DD DD83256503A patent/DD234273A5/de not_active IP Right Cessation
- 1983-11-10 PL PL1983244495A patent/PL146421B1/pl unknown
- 1983-11-15 KR KR1019830005425A patent/KR900003454B1/ko not_active Expired
- 1983-11-22 YU YU2299/83A patent/YU43199B/xx unknown
- 1983-11-23 PT PT77710A patent/PT77710B/pt unknown
- 1983-12-01 BG BG096741A patent/BG60165B2/bg unknown
- 1983-12-01 BG BG063287A patent/BG60103B2/bg unknown
- 1983-12-05 BR BR8306690A patent/BR8306690A/pt not_active IP Right Cessation
- 1983-12-21 MX MX199858A patent/MX158972A/es unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1166664A3 (ru) | Способ борьбы с нежелательной растительностью | |
| FI57955C (fi) | N-fosfonometylglysinderivat som kan anvaendas som herbisidiskt eller fytotoxiskt medel | |
| CS235988B2 (en) | Method of n-phosphonomethylglycine organic salts preparation | |
| EP0102694B1 (en) | Method for preparation of n-phosphonomethylglycine | |
| US4422982A (en) | Method for preparation of N-phosphonomethylglycine | |
| JPH0257077B2 (en]) | ||
| CS239903B2 (en) | Processing of aminomethyl phosphoric acid derivatives | |
| US5300680A (en) | Process for preparing sulfonium or sulfoxonium salts of N-phosphonomethylglycine | |
| US4507251A (en) | β-Oximinoalkylphosphonic acid esters | |
| SU673139A3 (ru) | Инсектицидное средство | |
| HRP940884A2 (en) | Method for preparation of salts of n-phosphonomethylglycine | |
| US4743403A (en) | Process for preparing organo-sulfonium halides | |
| EP0369076A1 (en) | Process for preparation of trisubstituted sulfonium and sulfoxonium salts of N-phosphonomethylglycine | |
| US3886238A (en) | S,S-dialkyl-N-substituted phosphoroamidodithionites | |
| CS242887B2 (en) | Method of n-phosphonium methyl glycine preparation | |
| PL141020B1 (en) | Process for preparing n-phosphonomethylglycine | |
| PL237983B1 (pl) | Sacharyniany alkilo[2-(2-hydroksyetoksy)etylo]dimetyloamoniowe, sposób ich otrzymywania oraz zastosowanie jako deterenty pokarmowe | |
| CS241089B2 (en) | Method of n-phosphonomethylglycine and its salts' production | |
| PL237982B1 (pl) | Acesulfamiany alkilo[2-(2-hydroksyetoksy)etylo]dimetyloamoniowe, sposób ich otrzymywania oraz zastosowanie jako deterenty pokarmowe | |
| JPH0149140B2 (en]) |