EP0257066A1 - Water soluble powder glyphosate formulation - Google Patents
Water soluble powder glyphosate formulationInfo
- Publication number
- EP0257066A1 EP0257066A1 EP87901322A EP87901322A EP0257066A1 EP 0257066 A1 EP0257066 A1 EP 0257066A1 EP 87901322 A EP87901322 A EP 87901322A EP 87901322 A EP87901322 A EP 87901322A EP 0257066 A1 EP0257066 A1 EP 0257066A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formulation
- glyphosate
- alkyl
- active agent
- water soluble
- 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.)
- Ceased
Links
Classifications
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
Definitions
- This invention relates to a novel watersoluble powdered glyphosate formulation.
- Glyphosate (N-phosphonomethylglycine) is well- known in the art as an effective herbicide. It is known in the art that glyphosate, which is an organic acid, is rela ⁇ tively insoluble in water. Therefore, glyphosate is normally formulaed and applied as a water-soluble salt, especially as the isopropylamine salt.
- glyphosate is normally formulaed and applied as a water-soluble salt, especially as the isopropylamine salt.
- Various formulations of glyphosate are disclosed in U.S. Patents 4,405,531, 3977,860 and 3,853,530.
- Roundup ⁇ Herbicide is the widely used commercial form of glyphosate and comprises the isopropylamine salt of glyphosate, surfactant(s) , other adjuvants and water. Roundup® Herbicide is sold as a water-soluble concentrate.
- the present invention relates to a herbicidal water ⁇ soluble dry-particulate glyphosate formulation comprising the sodium salt of glyphosate and a surface active agent having the following formula:
- R, and R ⁇ are independently methyl or ethyl;
- R 3 is methyl, ethyl, benzyl or C 1Q to C _ alkyl;
- R. is Cm r , to C- o alkyl and
- X is chloro or bromo.
- the water soluble powder formulation of the present invention has an efficacy substantially equivalent to Roundup® Herbicide ' .
- the powdered formulation will enable substantial savings in transportation and storage costs. A more thorough disclosure of the present invention is presented in the detail ⁇ ed description which follows.
- the present invention relates to a herbicidal, water soluble dry-particulate glyphosate formulation compris ⁇ ing the sodium salt of glyphosate and a surface-active agent having the following formula:
- R 2 NR 3 (X) R tripod wherein R, and R ⁇ are independently methyl or ethyl; R 3 is methyl, ethyl, benzyl or C . to C g alkyl, R 4 is C- Q to C.g alkyl and C is chloro or bromo.
- the water-soluble dry-particulate glyphosate formu ⁇ lation of the present invention has herbicidal efficacy which is substantially equivalent to the commercial glyphosate • formulation Roundup. Further; the formulation of the present invention is comparably efficacious at smaller surfactant to glyphosate rations than sodium glyphosate formulations com ⁇ prising the same surfactant(s) as' used in Roundup Herbicide. This indicates that the surfactants of the present invention are more efficient in maintaining the sodium salt of glypho- • sate in contact with the surface of the. plant to facilitate penetration of the glyphosate into the plant than is the surf ⁇ actant(s) used in Roundupr Herbicide.
- Glyphosate is well-known to those skilled in the art.
- Several processes for the preparation of glyphosate are disclosed in the patent and chemical literature, e.g., U.S. Patents 3,977,860 and 4,486,358.
- the * powdered sodium salt of glyphosate (mono, di, sesqui) can be prepared by a variety of processes.
- the sodium salt of glyphosate can be prepared in accordance with the procedure set forth in U.S. Patent 4,140,513.
- glyphosate can be mixed with an alkali base such as sodium hydroxide and the solution spray- dried to form the powdered sodium salt of gylphosate.
- the mono-sodium salt can be prepared by adding a solid alkali metal base with agitation to an aqueous slurry of N-phosphonomethylglycine containing at least 50% solids.
- Surfactants useful in the formulation of the present invention are commercially available from a number of manufacturers. Suitable surfactants are •described in McCutcheon's Detergents and Emulsifiers, North American Edition 1980 Annual and in McCutcheon's Detergent and Emulsifiers International Edition 1982. Suitable surfactants which are useful in the formulation of the present invention are alkyl-trimethyl ammonium chloride, alkyl-benzyl-dimethyl ammonium chloride and dialkyl dimethyl ammonium chloride. The preferred alkyl-trimethyl ammonium chloride surfactant is cetyl- trimethyl ammonium chloride. Preferred cetyl-trimethyl.
- ammonium chlorides are Emulgin IB-25, Drewfax 277, Dehyquat A and Dodigin 226. It will be obvious to one skilled in the art that other surfactants within the scope of the present invention will also be useful.
- the formulations of the present invention are comprised of a dry, free-flowing particulate solid with varying particle sizes from powder to granules. Formulations of the present invention comprise the following ingredients:
- the sodium sailt of glyphosate useful in the formulation of the present invention will suitably have a water content of less than 3% by weight.
- the formulations of the present invention may also be admixed with other additives such as urea, ammonium sulfate, silica, thickening agents, anti-foam agents such as silicones, water-repellants, humectants, chelating agents, dyes, dispersing agents, and other powdered active " ingredients such as herbicides and fungicides or the like.
- additives such as urea, ammonium sulfate, silica, thickening agents, anti-foam agents such as silicones, water-repellants, humectants, chelating agents, dyes, dispersing agents, and other powdered active " ingredients such as herbicides and fungicides or the like.
- formulations of the present invention can be readily diluted in water by the farmer in a spray tank prior to use. Suitable application rates of active ingredients will vary depending on plant species, but generally 90 to 360 grams per hectare on an acid equivalent basis will be suitable.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
La présente invention se rapporte à une nouvelle composition de glyphosate en poudre hydrosoluble.The present invention relates to a new composition of glyphosate in water-soluble powder.
Description
Title: "WATER SOLUBLE POWDER GLYPHOSATE FORMULATION"
This invention relates to a novel watersoluble powdered glyphosate formulation.
Glyphosate (N-phosphonomethylglycine) is well- known in the art as an effective herbicide. It is known in the art that glyphosate, which is an organic acid, is rela¬ tively insoluble in water. Therefore, glyphosate is normally formulaed and applied as a water-soluble salt, especially as the isopropylamine salt. Various formulations of glyphosate are disclosed in U.S. Patents 4,405,531, 3977,860 and 3,853,530. Roundup^ Herbicide is the widely used commercial form of glyphosate and comprises the isopropylamine salt of glyphosate, surfactant(s) , other adjuvants and water. Roundup® Herbicide is sold as a water-soluble concentrate.
It is desired in the art to find a water-soluble powder formulation of glyphosate which has the equivalent efficacy of Roundup^
Summary of the Invention
The present invention relates to a herbicidal water¬ soluble dry-particulate glyphosate formulation comprising the sodium salt of glyphosate and a surface active agent having the following formula:
wherein R, and R~ are independently methyl or ethyl; R3 is methyl, ethyl, benzyl or C1Q to C _ alkyl; R. is Cm r, to C- o alkyl and X is chloro or bromo.
The water soluble powder formulation of the present invention has an efficacy substantially equivalent to Roundup® Herbicide'. The powdered formulation will enable substantial savings in transportation and storage costs. A more thorough disclosure of the present invention is presented in the detail¬ ed description which follows.
Detailed Description of The Invention
The present invention relates to a herbicidal, water soluble dry-particulate glyphosate formulation compris¬ ing the sodium salt of glyphosate and a surface-active agent having the following formula:
R2NR3 (X) R„ wherein R, and R~ are independently methyl or ethyl; R3 is methyl, ethyl, benzyl or C . to C g alkyl, R4 is C-Q to C.g alkyl and C is chloro or bromo.
The water-soluble dry-particulate glyphosate formu¬ lation of the present invention has herbicidal efficacy which is substantially equivalent to the commercial glyphosate• formulation Roundup. Further; the formulation of the present invention is comparably efficacious at smaller surfactant to glyphosate rations than sodium glyphosate formulations com¬ prising the same surfactant(s) as' used in Roundup Herbicide. This indicates that the surfactants of the present invention are more efficient in maintaining the sodium salt of glypho- • sate in contact with the surface of the. plant to facilitate penetration of the glyphosate into the plant than is the surf¬ actant(s) used in Roundupr Herbicide.
Glyphosate is well-known to those skilled in the art. Several processes for the preparation of glyphosate are disclosed in the patent and chemical literature, e.g., U.S. Patents 3,977,860 and 4,486,358. The* powdered sodium salt of glyphosate (mono, di, sesqui) can be prepared by a variety of processes. First, the sodium salt of glyphosate can be prepared in accordance with the procedure set forth in U.S. Patent 4,140,513. Alternatively, glyphosate can be mixed with an alkali base such as sodium hydroxide and the solution spray- dried to form the powdered sodium salt of gylphosate. Alternatively, the mono-sodium salt can be prepared by adding a solid alkali metal base with agitation to an aqueous slurry of N-phosphonomethylglycine containing at least 50% solids.
Surfactants useful in the formulation of the present invention are commercially available from a number of manufacturers. Suitable surfactants are •described in McCutcheon's Detergents and Emulsifiers, North American Edition 1980 Annual and in McCutcheon's Detergent and Emulsifiers International Edition 1982. Suitable surfactants which are useful in the formulation of the present invention are alkyl-trimethyl ammonium chloride, alkyl-benzyl-dimethyl ammonium chloride and dialkyl dimethyl ammonium chloride. The preferred alkyl-trimethyl ammonium chloride surfactant is cetyl- trimethyl ammonium chloride. Preferred cetyl-trimethyl. ammonium chlorides are Emulgin IB-25, Drewfax 277, Dehyquat A and Dodigin 226. It will be obvious to one skilled in the art that other surfactants within the scope of the present invention will also be useful. The formulations of the present invention are comprised of a dry, free-flowing particulate solid with varying particle sizes from powder to granules.
Formulations of the present invention comprise the following ingredients:
Ingredient Wt % sodium glyphosate 5 to 95 Surfactant 5 to 40
Preferred formulations are as follows:
Ingredient Wt % sodium glyphosate 15 to 85 surfactant 5 to 20
The sodium sailt of glyphosate useful in the formulation of the present invention will suitably have a water content of less than 3% by weight.
The formulations of the present invention may also be admixed with other additives such as urea, ammonium sulfate, silica, thickening agents, anti-foam agents such as silicones, water-repellants, humectants, chelating agents, dyes, dispersing agents, and other powdered active" ingredients such as herbicides and fungicides or the like.
The formulations of the present invention can be readily diluted in water by the farmer in a spray tank prior to use. Suitable application rates of active ingredients will vary depending on plant species, but generally 90 to 360 grams per hectare on an acid equivalent basis will be suitable.
The following examples are presented to illustrate the present invention as well as some of the various embodiments of the invention. These examples are presented as being illustrative of the
novel formulations and are.not intended to be a limitation after the scope thereof.
Example 1
Typical formulation Wt %
1. monosodium glyphosate 91.2 cetyl trimethyl ammonium chloride 8.8
2. monosodium glyphosεte 90.9 alkyl dimethyl benzyl ammonium 9.1 chloride
Example 2
In this greenhouse test, two variety of difficult to kill plants prevalent in Brazil were treated with formulations of the present invention, Brachiaria (a narrow leaf plant) and Euphorbia (a broad leaf plant). The mono-sodium salt of glyphosate was tank-mixed in water with the indicated surfactant to provide indicated glyphosate concentration as set forth in the following tables. "A" designated trade secret surfactant(s) used in Roundup® Herbicide. "B" designates a surfactant chemically identical to "A" but produced by a different manufacture.
Table. I •
Test 1
Rate Percent Control
Glyphosate ** Surfactant Brachiaria Euphorbia
(q/ha) Surfactant Rate DAT) DAT)*
360 Drewfax 277 90 99 (20) 69 (20)
II 180 99 74 II
Emulgin IB-25 90 95 63 II
II 180 97 67 II
B 90 97 74 II
II 180 100 80 II
Roundup® 99 80 II
Test 2
360 Emulgin IB-25 90 96 (21) 41 (21)
II 180 97 66 II
Dehyquat A 90 92 49 II
II 180 100 67 II
A 90 98 59 II
II 180 96 62 II
•B 90 98 64 II
II 180 98 71 II
Roundup® 100 73 II
* Days after treatment ** Acid equivalent basis
Table II
Surfactant Percent Control
Commercial Ratio BRACHIARIA EUPHORBIA Name Common Name Glyph*:Surf 10 DAT. 21 DAT 10 DAT 21 DAT
Emulgin cetyl-trimethyl IB-25 ammonium chloride 1:0.06 83 92 53 69
II II 1:0.13 86 97 58 74
II II 1:0.19 96 99 60 72
Dodigen 226 alkyl-benzyl-
10 dimethyl ammonium chloride 1:0,13 69 91 61 74
II II 1:0.25 78 96 59 75
II II 1:0.38 93 98 77 79
•
Dodigen dialkyl dimethyl
15 1881 ammonium chloride 1:0.13 79 91 52 68
II II 1:0.25 87 97 63 71
Roundup® 97 99 50 75
* Acid equivalent basis
Table III Application glyphosate concentration 360 g ha (a.e.)
Percent Control
Rate Brachiaria Euphorbia
Surfactant g ha 21 DAT 21 DAT
Emulgin IB-25 45 91 32
II 90 93 47
II 180 95 53
A 45 85 47 ω
10 II 90 95 56 I
II 180 98 68
Roundup® • 98 50
Although this invention has been described with respect to specific embodiments, the details" hereof are not to be construed as limitations, for it will be apparent that various equivalents, changes and- modifications may be resorted to without departing from the spirit and scope thereof and it is understood that such equivalent embodiments are intended to be included within the scope of this invention.
Claims
1. A herbicidal water-soluble, particulate formulation comprising the sodium salt of N-phosphono- methylgycine and a surface-active agent having the following formula:
wherein t and R2 are independently methyl or ethyl; R3 is methyl, ethyl benzyl or C10 to C18 alkyl; R4 is Cio to Cis alkyl and X is chloro or bromo.
2. The formulation of Claim 1 wherein the salt of N-phosphonomethylglycine is the monosodium salt.
3. The formulation of Claim 1 wherein the- surface active agent is cetyl-trimethylammonium chloride.
4. The formulation of Claim 1 wherein the surface active agent is alkyl-benzyl-dimethylammonium chloride.
5. The formulation of Claim 1 wherein the surface active agent is dialkyl dimethylammonium chloride. -11-
6. A herbicidal, water soluble, particulate formulation comprising the monosodium salt 'of N-phosphonomethylglycine and a surface active agent having the following formula:
wherein Rx and R2 are independently methyl, ethyl; R3 is methyl, ethyl, or benzylor Cι0 to C18 alkyl; R4 is Cio to C18 alkyl and X is chloro or bromo.
7. A herbicidal, water soluble, particulate formulation comprising the monosodium salt of N-phos¬ phonomethylglycine and cetyl-trimethyl ammonium chloride,
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR8600462A BR8600462A (en) | 1986-02-04 | 1986-02-04 | HERBICIDE FORMULATION |
| BR8600462 | 1986-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0257066A1 true EP0257066A1 (en) | 1988-03-02 |
Family
ID=4039479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87901322A Ceased EP0257066A1 (en) | 1986-02-04 | 1987-02-03 | Water soluble powder glyphosate formulation |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0257066A1 (en) |
| JP (1) | JPS63502826A (en) |
| AU (1) | AU590829B2 (en) |
| BR (1) | BR8600462A (en) |
| DK (1) | DK515887A (en) |
| FI (1) | FI874262A (en) |
| HU (1) | HU200542B (en) |
| NO (1) | NO874158D0 (en) |
| RO (1) | RO100335A2 (en) |
| WO (1) | WO1987004595A1 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ231897A (en) * | 1988-12-30 | 1992-09-25 | Monsanto Co | Dry water-soluble granular composition comprising glyphosate and a liquid surfactant |
| DE3926800A1 (en) * | 1989-08-14 | 1991-02-21 | Hoechst Ag | WATER-DISPERSIBLE GRANULES FOR USE IN PLANT PROTECTION |
| US5364832A (en) * | 1990-08-10 | 1994-11-15 | Hoechst Aktiengesellschaft | Water-dispersible granules comprising fenoxaprop-ethyl and/or fenchlorazole |
| DK165156C (en) * | 1989-12-20 | 1993-03-01 | Cheminova Agro As | HERBICID FORMULATION CONTAINING GLYPHOSATE ACID |
| GB9002495D0 (en) * | 1990-02-05 | 1990-04-04 | Monsanto Europe Sa | Glyphosate compositions |
| US5430005A (en) * | 1991-08-02 | 1995-07-04 | Monsanto Company | Herbicidal compositions |
| US5614468A (en) * | 1995-06-07 | 1997-03-25 | Monsanto Company | Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a liquid-solid reaction system |
| US5633397A (en) * | 1995-06-07 | 1997-05-27 | Monsanto Company | Preparation of ammonium glyphosate via a gas-solid reaction system |
| US5710103A (en) * | 1996-04-03 | 1998-01-20 | Albemarle Corporation | Glyphosate compositions comprising hydrocarbyl dimethyl amine oxide and quaternary ammonium halide |
| US5783516A (en) * | 1996-06-28 | 1998-07-21 | Albemarle Corporation | Herbicidal and plant growth regulant compositions and their use |
| US5703016A (en) * | 1996-09-30 | 1997-12-30 | Albemarle Corporation | Surfactant composition for use with glyphosate comprising dimethyl amine oxide, polyethoxylated alcohol, and pyridinium halide |
| US6107249A (en) * | 1996-10-07 | 2000-08-22 | Zeneca Limited | Glyphosate formulations |
| PT936860E (en) * | 1996-10-25 | 2002-07-31 | Monsanto Technology Llc | COMPOSITION AND METHOD FOR TREATING PLANTS WITH EXOGENEOUS CHEMICALS |
| AR010033A1 (en) * | 1996-10-25 | 2000-05-17 | Monsanto Technology Llc | COMPOSITION AND METHOD FOR TREATING PLANTS WITH EXOGENOUS CHEMICAL COMPOUNDS. |
| CZ2002254A3 (en) | 1999-07-28 | 2002-07-17 | Monsanto Technology Llc | Process for preparing ammonium glyphosate paste that can be subjected to further treatment |
| 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 |
| US6734142B2 (en) | 2001-04-23 | 2004-05-11 | Monsanto Technology Llc | Ammonium glyphosate compositions and process for their preparation |
| EP1538910A2 (en) | 2002-08-31 | 2005-06-15 | Monsanto Technology LLC | Process for the preparation of a dry pesticidal composition containing a dicarboxylate component |
| CN100389116C (en) * | 2006-06-12 | 2008-05-21 | 江苏好收成韦恩农药化工有限公司 | Method for producing glyphosate monovalent salt using glyphosate bivalent, trivalent salt |
| MX2009008934A (en) * | 2007-02-26 | 2009-08-28 | Dow Agrosciences Llc | Process for the preparation of certain substituted sulfilimines. |
| CA3033440A1 (en) | 2016-08-09 | 2018-02-15 | Monsanto Technology Llc | Herbicidal compositions comprising glyphosate and a monocarboxylic acid salt |
| EP3821709A4 (en) * | 2018-07-05 | 2022-04-13 | Kao Corporation | Herbicide composition |
| JP7321761B2 (en) | 2018-07-05 | 2023-08-07 | 花王株式会社 | herbicide composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3008186A1 (en) * | 1980-03-04 | 1981-10-15 | Hoechst Ag, 6000 Frankfurt | SYNERGISTIC COMBINATIONS OF PHOSPHINOTHRICIN |
| AU6912181A (en) * | 1980-04-18 | 1981-10-22 | Imperial Chemical Industries Ltd. | Pesticidal formulations |
| DE3035554A1 (en) * | 1980-09-20 | 1982-05-06 | Hoechst Ag, 6000 Frankfurt | HERBICIDAL AGENTS |
| US4528023A (en) * | 1983-07-25 | 1985-07-09 | Stauffer Chemical Company | Enhancement of herbicidal activity of tetraaluminum salts of N-phosphonomethylglycine |
| FI86501C (en) * | 1985-05-29 | 1992-09-10 | Stauffer Chemical Co | Solid, essentially non-hygroscopic phytoactive mixture and its predominant aging process |
-
1986
- 1986-02-04 BR BR8600462A patent/BR8600462A/en unknown
-
1987
- 1987-02-03 WO PCT/BR1987/000004 patent/WO1987004595A1/en not_active Application Discontinuation
- 1987-02-03 EP EP87901322A patent/EP0257066A1/en not_active Ceased
- 1987-02-03 HU HU871232A patent/HU200542B/en not_active IP Right Cessation
- 1987-02-03 JP JP62501265A patent/JPS63502826A/en active Pending
- 1987-02-03 AU AU70331/87A patent/AU590829B2/en not_active Ceased
- 1987-09-29 FI FI874262A patent/FI874262A/en not_active Application Discontinuation
- 1987-10-01 DK DK515887A patent/DK515887A/en not_active Application Discontinuation
- 1987-10-02 RO RO129937A patent/RO100335A2/en unknown
- 1987-10-02 NO NO874158A patent/NO874158D0/en unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO8704595A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7033187A (en) | 1987-08-25 |
| NO874158L (en) | 1987-10-02 |
| FI874262A0 (en) | 1987-09-29 |
| RO100335A2 (en) | 1991-08-27 |
| WO1987004595A1 (en) | 1987-08-13 |
| AU590829B2 (en) | 1989-11-16 |
| DK515887D0 (en) | 1987-10-01 |
| NO874158D0 (en) | 1987-10-02 |
| FI874262A (en) | 1987-09-29 |
| DK515887A (en) | 1987-10-01 |
| BR8600462A (en) | 1987-09-01 |
| JPS63502826A (en) | 1988-10-20 |
| RO100335B1 (en) | 1990-11-30 |
| HUT45855A (en) | 1988-09-28 |
| HU200542B (en) | 1990-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU590829B2 (en) | Water soluble powder glyphosate formulation | |
| AU691425B2 (en) | Glyphosate formulations containing etheramine surfactants | |
| EP0650326B1 (en) | Herbicidal compositions | |
| US5710103A (en) | Glyphosate compositions comprising hydrocarbyl dimethyl amine oxide and quaternary ammonium halide | |
| AU728022B2 (en) | Herbicidal and plant growth regulant compositions and the use thereof | |
| EP0483095A2 (en) | Improved formulations | |
| KR100189390B1 (en) | Herbicide solution based on N-phosphonomethylglycine | |
| EP0902622B1 (en) | Herbicidal and plant growth regulant compositions and their use | |
| US5710104A (en) | Glyphosate compositions comprising polyethoxylated monohydric primary alcohols | |
| US5783516A (en) | Herbicidal and plant growth regulant compositions and their use | |
| EP0902621B1 (en) | Herbicidal and plant growth regulant compositions and their use | |
| WO1997036494A1 (en) | Herbicidal and plant growth regulant compositions and their use | |
| CA2318657E (en) | Glyphosate formulations containing etheramine surfactants | |
| JP2004527565A (en) | Glyphosate composition and use thereof | |
| WO1997036490A1 (en) | Herbicidal and plant growth regulant compositions and their use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE FR GB IT LI LU NL SE |
|
| 17P | Request for examination filed |
Effective date: 19880209 |
|
| 17Q | First examination report despatched |
Effective date: 19890620 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED |
|
| 18R | Application refused |
Effective date: 19910822 |
|
| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: TEIXEIRA COSTA FILHO, GERALDO Inventor name: BERGSON FERNANDES BARRETO, HENRI Inventor name: VON ZUBEN, FERNANDO, JOSE |