CA2221298C - Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a solid reaction system - Google Patents
Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a solid reaction system Download PDFInfo
- Publication number
- CA2221298C CA2221298C CA002221298A CA2221298A CA2221298C CA 2221298 C CA2221298 C CA 2221298C CA 002221298 A CA002221298 A CA 002221298A CA 2221298 A CA2221298 A CA 2221298A CA 2221298 C CA2221298 C CA 2221298C
- Authority
- CA
- Canada
- Prior art keywords
- ammonium hydroxide
- glyphosate
- moisture content
- reaction mass
- product
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000000908 ammonium hydroxide Substances 0.000 title claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 44
- PDYXIVPKOMYDOK-UHFFFAOYSA-N Glyphosate-monoammonium Chemical compound [NH4+].OC(=O)CNCP(O)([O-])=O PDYXIVPKOMYDOK-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000007787 solid Substances 0.000 title abstract description 20
- 238000002360 preparation method Methods 0.000 title description 2
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000005562 Glyphosate Substances 0.000 claims abstract description 44
- 229940097068 glyphosate Drugs 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 29
- 239000002671 adjuvant Substances 0.000 claims abstract description 19
- 238000001035 drying Methods 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000003247 decreasing effect Effects 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 52
- 239000000843 powder Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 4
- 230000007423 decrease Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 abstract description 13
- 230000002363 herbicidal effect Effects 0.000 abstract description 10
- 239000004009 herbicide Substances 0.000 abstract description 9
- 239000005648 plant growth regulator Substances 0.000 abstract description 5
- 238000000227 grinding Methods 0.000 abstract description 4
- 230000003134 recirculating effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 38
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 28
- 229940001482 sodium sulfite Drugs 0.000 description 14
- 235000010265 sodium sulphite Nutrition 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 4
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 4
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 4
- 239000001099 ammonium carbonate Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- -1 flakes Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000007602 hot air drying Methods 0.000 description 2
- 150000004005 nitrosamines Chemical class 0.000 description 2
- 235000012149 noodles Nutrition 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DKEKFGVEUYLUPF-UHFFFAOYSA-N P(O)(O)(O)=O.NC(CCC)C(=O)O Chemical compound P(O)(O)(O)=O.NC(CCC)C(=O)O DKEKFGVEUYLUPF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000007425 progressive decline Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000011282 treatment 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)]
-
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/472,152 | 1995-06-07 | ||
| US08/472,152 US5614468A (en) | 1995-06-07 | 1995-06-07 | Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a liquid-solid reaction system |
| PCT/US1996/003081 WO1996040696A1 (en) | 1995-06-07 | 1996-03-05 | Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a liquid-solid reaction system |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2221298A1 CA2221298A1 (en) | 1996-12-19 |
| CA2221298C true CA2221298C (en) | 2001-06-05 |
Family
ID=23874396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002221298A Expired - Lifetime CA2221298C (en) | 1995-06-07 | 1996-03-05 | Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a solid reaction system |
Country Status (23)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5633397A (en) * | 1995-06-07 | 1997-05-27 | Monsanto Company | Preparation of ammonium glyphosate via a gas-solid reaction system |
| ATE277517T1 (de) * | 1999-07-28 | 2004-10-15 | Monsanto Technology Llp | Verfahren zur herstellung einer nachhaltig verarbeitbaren ammonium glyphosat paste |
| US6599858B1 (en) * | 1999-07-29 | 2003-07-29 | Monsanto Technology Llc | Process for making ammonium glyphosate flakes |
| US6448434B1 (en) * | 1999-07-29 | 2002-09-10 | Monsanto Technology Llc | Process for making ammonium glyphosate powder |
| CN1072672C (zh) * | 1999-11-08 | 2001-10-10 | 浙江新安化工集团股份有限公司 | 草甘膦酸铵的制备方法 |
| US6734142B2 (en) | 2001-04-23 | 2004-05-11 | Monsanto Technology Llc | Ammonium glyphosate compositions and process for their preparation |
| RU2210212C1 (ru) * | 2002-05-06 | 2003-08-20 | Кубанский государственный аграрный университет | Способ увеличения устойчивости сахарной свеклы к фитотоксическому воздействию гербицида раундап |
| RU2208314C1 (ru) * | 2002-05-06 | 2003-07-20 | Кубанский государственный аграрный университет | Раундапный антидот для вегетирующих растений сахарной свеклы |
| WO2004019684A2 (en) * | 2002-08-31 | 2004-03-11 | Monsanto Technology Llc | Process for the preparation of a dry pesticidal composition containing a dicarbodylate component |
| BR0313970A (pt) * | 2002-08-31 | 2005-09-06 | Monsanto Technology Llc | Composições pesticidas contendo ácidos dicarboxìlicos |
| US20050037924A1 (en) * | 2002-08-31 | 2005-02-17 | Monsanto Technology Llc | Sodium glyphosate compositions and process for their preparation |
| CN1244587C (zh) * | 2002-09-05 | 2006-03-08 | 浙江新安化工集团股份有限公司 | 气－液－固三相反应及溶剂萃取制备草甘膦酸铵 |
| AR037559A1 (es) * | 2002-11-19 | 2004-11-17 | Atanor S A | Una formulacion herbicida solida de n-fosfonometilglicina, bajo la forma de polvo, granulos o escamas, soluble o dispersable en agua, y el procedimiento para preparar dicha composicion |
| CN1328283C (zh) * | 2004-07-19 | 2007-07-25 | 中国科学院植物研究所 | 一种生产草甘膦酸铵盐的方法 |
| ITMI20051138A1 (it) * | 2005-06-17 | 2006-12-18 | Sipcam Spa | Processo per preparare granuli di glifosate ammonico |
| US20110071027A1 (en) * | 2009-09-18 | 2011-03-24 | Volker Heide | High strength aqueous glyphosate salt concentrates and methods |
| CN103109801B (zh) * | 2013-03-06 | 2014-08-27 | 段凤羽 | 一种草甘膦助剂及其制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4840659A (en) * | 1971-03-10 | 1989-06-20 | Monsanto Company | N-Phosphonomethylglycine phytotoxicant compositions |
| BR8600462A (pt) * | 1986-02-04 | 1987-09-01 | Monsanto Brasil | Formulacao herbicida |
| ZA871571B (en) * | 1986-03-20 | 1987-08-24 | Uniroyal Chemical Company, Inc. | Dry reactive processing |
| US5070197A (en) * | 1986-03-20 | 1991-12-03 | Uniroyal Chemical Company, Inc. | Dry reactive processing |
| US5047079A (en) * | 1986-08-18 | 1991-09-10 | Ici Americas Inc. | Method of preparation and use of solid, phytoactive compositions |
| JPH0825849B2 (ja) * | 1986-08-18 | 1996-03-13 | ストウフアー ケミカル カンパニー | 固形の植物活性組成物調製方法 |
| NZ231897A (en) * | 1988-12-30 | 1992-09-25 | Monsanto Co | Dry water-soluble granular composition comprising glyphosate and a liquid surfactant |
| NO901662L (no) * | 1989-04-17 | 1990-12-21 | Monsanto Co | Toert herbicid preparat med forbedret vannopploeselighet. |
| WO1992012637A1 (en) * | 1991-01-24 | 1992-08-06 | Monsanto Company | Improved glyphosate formulations |
| 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 |
| US5430005A (en) * | 1991-08-02 | 1995-07-04 | Monsanto Company | Herbicidal compositions |
| US5266553A (en) * | 1991-10-21 | 1993-11-30 | Riverdale Chemical Company | Method of manufacturing a dry water-soluble herbicidal salt composition |
| FR2692439A1 (fr) * | 1992-05-26 | 1993-12-24 | Osa Sacifia Prod | Produit applicable, comme agent phytotoxique comprenant un sel d'ammonium de (N-Phosphonométhyl)glycine, composition concentrée et préparation phytotoxique le contenant. |
| MY111437A (en) * | 1992-07-31 | 2000-05-31 | Monsanto Co | Improved glyphosate herbicide formulation. |
| WO1994010844A1 (en) * | 1992-11-06 | 1994-05-26 | Zeneca Limited | Dry water-dispersible glyphosate phytoactive formulation |
| US5633397A (en) * | 1995-06-07 | 1997-05-27 | Monsanto Company | Preparation of ammonium glyphosate via a gas-solid reaction system |
-
1995
- 1995-06-07 US US08/472,152 patent/US5614468A/en not_active Expired - Lifetime
-
1996
- 1996-03-05 PT PT96913769T patent/PT845000E/pt unknown
- 1996-03-05 NZ NZ307310A patent/NZ307310A/xx unknown
- 1996-03-05 JP JP9500436A patent/JP2963543B2/ja not_active Expired - Fee Related
- 1996-03-05 HU HU9802333A patent/HUP9802333A3/hu unknown
- 1996-03-05 KR KR1019970709040A patent/KR100266126B1/ko not_active Expired - Fee Related
- 1996-03-05 ES ES96913769T patent/ES2157441T3/es not_active Expired - Lifetime
- 1996-03-05 EP EP96913769A patent/EP0845000B1/en not_active Expired - Lifetime
- 1996-03-05 CA CA002221298A patent/CA2221298C/en not_active Expired - Lifetime
- 1996-03-05 BR BR9608562A patent/BR9608562A/pt not_active IP Right Cessation
- 1996-03-05 DK DK96913769T patent/DK0845000T3/da active
- 1996-03-05 WO PCT/US1996/003081 patent/WO1996040696A1/en active IP Right Grant
- 1996-03-05 DE DE69612857T patent/DE69612857T2/de not_active Expired - Lifetime
- 1996-03-05 RU RU98100223/04A patent/RU2164519C2/ru active
- 1996-03-05 AT AT96913769T patent/ATE201210T1/de not_active IP Right Cessation
- 1996-03-05 CN CN96196134A patent/CN1068601C/zh not_active Expired - Lifetime
- 1996-03-05 UA UA98010006A patent/UA48971C2/uk unknown
- 1996-03-05 AU AU56620/96A patent/AU694877B2/en not_active Expired
- 1996-03-14 TW TW085103069A patent/TW306867B/zh active
- 1996-05-23 AR ARP960102690A patent/AR004487A1/es active IP Right Grant
- 1996-06-05 IL IL11857796A patent/IL118577A/en not_active IP Right Cessation
- 1996-06-06 ZA ZA964775A patent/ZA964775B/xx unknown
-
1997
- 1997-01-03 US US08/778,890 patent/US5716903A/en not_active Expired - Lifetime
-
2001
- 2001-08-08 GR GR20010401207T patent/GR3036355T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| UA48971C2 (uk) | 2002-09-16 |
| TW306867B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-06-01 |
| NZ307310A (en) | 1999-01-28 |
| AU5662096A (en) | 1996-12-30 |
| CN1068601C (zh) | 2001-07-18 |
| IL118577A (en) | 2001-05-20 |
| HUP9802333A3 (en) | 1999-03-29 |
| PT845000E (pt) | 2001-09-28 |
| AU694877B2 (en) | 1998-07-30 |
| DE69612857D1 (de) | 2001-06-21 |
| HUP9802333A2 (hu) | 1999-02-01 |
| IL118577A0 (en) | 1996-10-16 |
| EP0845000B1 (en) | 2001-05-16 |
| ES2157441T3 (es) | 2001-08-16 |
| CA2221298A1 (en) | 1996-12-19 |
| KR100266126B1 (ko) | 2000-09-15 |
| KR19990022559A (ko) | 1999-03-25 |
| AR004487A1 (es) | 1998-12-16 |
| ZA964775B (en) | 1997-01-08 |
| CN1192743A (zh) | 1998-09-09 |
| ATE201210T1 (de) | 2001-06-15 |
| JP2963543B2 (ja) | 1999-10-18 |
| DK0845000T3 (da) | 2001-06-18 |
| GR3036355T3 (en) | 2001-11-30 |
| BR9608562A (pt) | 1999-07-06 |
| DE69612857T2 (de) | 2002-03-28 |
| JPH10507467A (ja) | 1998-07-21 |
| RU2164519C2 (ru) | 2001-03-27 |
| US5716903A (en) | 1998-02-10 |
| WO1996040696A1 (en) | 1996-12-19 |
| US5614468A (en) | 1997-03-25 |
| EP0845000A1 (en) | 1998-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2221298C (en) | Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a solid reaction system | |
| EP0378985B1 (en) | Improved glyphosate formulations | |
| CA2221299C (en) | Preparation of ammonium glyphosate via a gas-solid reaction system | |
| US20090318295A1 (en) | Solid herbicidal formulation of N-(phosphono-methyl)glycine and process for its preparation | |
| MXPA97009885A (en) | Preparation of ammonium glifosate using aqueous ammonium hydroxide in a liquid-sol dereaccion system | |
| AU635514C (en) | Improved glyphosate formulations | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20160307 |
|
| MKEX | Expiry |
Effective date: 20160307 |