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WO1987004595A1 - Water soluble powder glyphosate formulation - Google Patents

Water soluble powder glyphosate formulation Download PDF

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Publication number
WO1987004595A1
WO1987004595A1 PCT/BR1987/000004 BR8700004W WO8704595A1 WO 1987004595 A1 WO1987004595 A1 WO 1987004595A1 BR 8700004 W BR8700004 W BR 8700004W WO 8704595 A1 WO8704595 A1 WO 8704595A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
glyphosate
alkyl
active agent
water soluble
Prior art date
Application number
PCT/BR1987/000004
Other languages
French (fr)
Inventor
Geraldo Teixeira Costa Filho
Fernando José VON ZUBEN
Henri Bergson Fernandes Barreto
Original Assignee
Monsanto Do Brasil S.A.
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.)
Filing date
Publication date
Application filed by Monsanto Do Brasil S.A. filed Critical Monsanto Do Brasil S.A.
Priority to HU871232A priority Critical patent/HU200542B/en
Publication of WO1987004595A1 publication Critical patent/WO1987004595A1/en
Priority to FI874262A priority patent/FI874262A/en
Priority to DK515887A priority patent/DK515887D0/en
Priority to NO874158A priority patent/NO874158L/en

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.

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  • 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

A novel water-soluble powder glyphosate formulation.

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:
Figure imgf000003_0001
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
Figure imgf000009_0001
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
Figure imgf000010_0001
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

WE CLAIM:
1. A herbicidal water-soluble, particulate formulation comprising the sodium salt of N-phosphono- methylgycine and a surface-active agent having the following formula:
Figure imgf000012_0001
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:
Figure imgf000013_0001
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,
PCT/BR1987/000004 1986-02-04 1987-02-03 Water soluble powder glyphosate formulation WO1987004595A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
HU871232A HU200542B (en) 1986-02-04 1987-02-03 Water soluble powder glyphosate formulation.
FI874262A FI874262A (en) 1986-02-04 1987-09-29 VATTYLOSLIG GLYFOSATPULVERSAMMANSAETTNING.
DK515887A DK515887D0 (en) 1986-02-04 1987-10-01 WATER SOLUBLE, POWDER-FORMULATED GLYPHOSATE FORMULATION
NO874158A NO874158L (en) 1986-02-04 1987-10-02 WATER SOLUBLE, POWDER-GLYPHOSATE MATERIALS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BR8600462A BR8600462A (en) 1986-02-04 1986-02-04 HERBICIDE FORMULATION
BRPI8600462 1986-02-04

Publications (1)

Publication Number Publication Date
WO1987004595A1 true WO1987004595A1 (en) 1987-08-13

Family

ID=4039479

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/BR1987/000004 WO1987004595A1 (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) DK515887D0 (en)
FI (1) FI874262A (en)
HU (1) HU200542B (en)
NO (1) NO874158L (en)
RO (1) RO100335A2 (en)
WO (1) WO1987004595A1 (en)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990007275A1 (en) * 1988-12-30 1990-07-12 Monsanto Company Improved glyphosate formulations
WO1991008666A1 (en) * 1989-12-20 1991-06-27 Cheminova Agro A/S A herbicidal formulation containing glyphosate acid
EP0526444A1 (en) * 1991-08-02 1993-02-03 Monsanto Company Herbicidal compositions
US5464807A (en) * 1990-02-05 1995-11-07 Monsanto Company Methods of using glyphosate compositions comprising alkoxylated quaternary ammonium surfactants
US5543385A (en) * 1989-08-14 1996-08-06 Hoechst Aktiengesellschaft Water-dispersible glufosinate granules
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
EP0413267B1 (en) * 1989-08-14 1997-11-12 Hoechst Schering AgrEvo GmbH Water-dispersible granules
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
US5710103A (en) * 1996-04-03 1998-01-20 Albemarle Corporation Glyphosate compositions comprising hydrocarbyl dimethyl amine oxide and quaternary ammonium halide
WO1998015181A1 (en) * 1996-10-07 1998-04-16 Zeneca Limited Glyphosate formulations
WO1998017110A1 (en) * 1996-10-25 1998-04-30 Monsanto Company Composition and method for treating plants with exogenous chemicals
US5783516A (en) * 1996-06-28 1998-07-21 Albemarle Corporation Herbicidal and plant growth regulant compositions and their use
US6130186A (en) * 1996-10-25 2000-10-10 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6448434B1 (en) 1999-07-29 2002-09-10 Monsanto Technology Llc Process for making ammonium glyphosate powder
US6599858B1 (en) 1999-07-29 2003-07-29 Monsanto Technology Llc Process for making ammonium glyphosate flakes
US6605568B1 (en) 1999-07-28 2003-08-12 Monsanto Technology Llc Process for making a downstream processable ammonium glyphosate paste
US6734142B2 (en) 2001-04-23 2004-05-11 Monsanto Technology Llc Ammonium glyphosate compositions and process for their preparation
US7141532B2 (en) 2002-08-31 2006-11-28 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
CN112367842A (en) * 2018-07-05 2021-02-12 花王株式会社 Herbicidal composition
US11129388B2 (en) 2016-08-09 2021-09-28 Monsanto Technology Llc Solid herbicidal concentrate compositions
EP3821709A4 (en) * 2018-07-05 2022-04-13 Kao Corporation Herbicide composition

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MX2009008934A (en) * 2007-02-26 2009-08-28 Dow Agrosciences Llc Process for the preparation of certain substituted sulfilimines.

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EP0039144A2 (en) * 1980-04-18 1981-11-04 Imperial Chemical Industries Plc Pesticidal formulations suitable for electrodynamic spraying and a solution suitable for use in making them
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US4528023A (en) * 1983-07-25 1985-07-09 Stauffer Chemical Company Enhancement of herbicidal activity of tetraaluminum salts of N-phosphonomethylglycine
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Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0378985A1 (en) * 1988-12-30 1990-07-25 Monsanto Company Improved glyphosate formulations
WO1990007275A1 (en) * 1988-12-30 1990-07-12 Monsanto Company Improved glyphosate formulations
US5872078A (en) * 1988-12-30 1999-02-16 Monsanto Europe S.A. Glyphosate formulations
US6228807B1 (en) 1988-12-30 2001-05-08 Monsanto Company Glyphosate formulations
US5656572A (en) * 1988-12-30 1997-08-12 Monsanto Company Method of controlling weeds
EP0413267B1 (en) * 1989-08-14 1997-11-12 Hoechst Schering AgrEvo GmbH Water-dispersible granules
US5543385A (en) * 1989-08-14 1996-08-06 Hoechst Aktiengesellschaft Water-dispersible glufosinate granules
WO1991008666A1 (en) * 1989-12-20 1991-06-27 Cheminova Agro A/S A herbicidal formulation containing glyphosate acid
US5464807A (en) * 1990-02-05 1995-11-07 Monsanto Company Methods of using glyphosate compositions comprising alkoxylated quaternary ammonium surfactants
EP0526444A1 (en) * 1991-08-02 1993-02-03 Monsanto Company Herbicidal compositions
US5633397A (en) * 1995-06-07 1997-05-27 Monsanto Company Preparation of ammonium glyphosate via a gas-solid reaction system
US5716903A (en) * 1995-06-07 1998-02-10 Monsanto Company Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a liquid-solid reaction system
US5614468A (en) * 1995-06-07 1997-03-25 Monsanto Company Preparation of ammonium glyphosate using aqueous ammonium hydroxide in a liquid-solid reaction system
US5710103A (en) * 1996-04-03 1998-01-20 Albemarle Corporation Glyphosate compositions comprising hydrocarbyl dimethyl amine oxide and quaternary ammonium halide
US5858921A (en) * 1996-04-03 1999-01-12 Albemarle Corporation Glyphosate herbicidal and plant growth regulant compositions and their use
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
WO1998015181A1 (en) * 1996-10-07 1998-04-16 Zeneca Limited Glyphosate formulations
AU755024B2 (en) * 1996-10-25 2002-11-28 Monsanto Technology Llc Composition and method for treating plants with exogenous chemicals
US6093680A (en) * 1996-10-25 2000-07-25 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6130186A (en) * 1996-10-25 2000-10-10 Monsanto Company Composition and method for treating plants with exogenous chemicals
WO1998017110A1 (en) * 1996-10-25 1998-04-30 Monsanto Company Composition and method for treating plants with exogenous chemicals
US6479434B1 (en) 1996-10-25 2002-11-12 Monsanto Technology Llc Composition and method for treating plants with exogenous chemicals
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EP0257066A1 (en) 1988-03-02
AU590829B2 (en) 1989-11-16
HU200542B (en) 1990-07-28
BR8600462A (en) 1987-09-01
FI874262A0 (en) 1987-09-29
DK515887A (en) 1987-10-01
DK515887D0 (en) 1987-10-01
HUT45855A (en) 1988-09-28
JPS63502826A (en) 1988-10-20
NO874158D0 (en) 1987-10-02
AU7033187A (en) 1987-08-25
RO100335B1 (en) 1990-11-30
RO100335A2 (en) 1991-08-27
NO874158L (en) 1987-10-02
FI874262A (en) 1987-09-29

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