GB2233229A - Concentrated herbicidal compositions based on N-phosphonomethylglycine - Google Patents

Concentrated herbicidal compositions based on N-phosphonomethylglycine Download PDF

Info

Publication number
GB2233229A
GB2233229A GB9013692A GB9013692A GB2233229A GB 2233229 A GB2233229 A GB 2233229A GB 9013692 A GB9013692 A GB 9013692A GB 9013692 A GB9013692 A GB 9013692A GB 2233229 A GB2233229 A GB 2233229A
Authority
GB
United Kingdom
Prior art keywords
composition according
glyphosate
derivatives
nature
surfactant
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.)
Granted
Application number
GB9013692A
Other versions
GB9013692D0 (en
GB2233229B (en
Inventor
Francois Darchy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience SA
Original Assignee
Rhone Poulenc Agrochimie SA
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 Rhone Poulenc Agrochimie SA filed Critical Rhone Poulenc Agrochimie SA
Publication of GB9013692D0 publication Critical patent/GB9013692D0/en
Publication of GB2233229A publication Critical patent/GB2233229A/en
Application granted granted Critical
Publication of GB2233229B publication Critical patent/GB2233229B/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • 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
    • 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
    • A01N25/02—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 containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Liquid herbicidal compositions which consist of aqueous solutions containing a) N-phosphonomethylglycine (glyphosate; (HO)2 P(O)CH2NHCH2COOH) and/or one of its derivatives in a proportion of at least 40 g/l of glyphosate equivalent, and b) a surfactant of formula <IMAGE> [in which R is a C8-22 linear or branched, alkyl or alkenyl chain; A denotes an alkylene group; n, n' and n'' are integers such that n + n' + n'' is @between 1 and 15; and R<1> is hydrogen or an acyl radical] which has the nature @of a biological activator/herbicide. Incorporation of the above surfactant enables concentrated glyphosphate compositions to be formulated.

Description

0 HERBICIDAL COMPOSITIONS BASED ON N-PHOSPHONOMETHYLGLYCINE is The present
invention relates to new concentrated formulations based on Nphosphonomethylglycine or on compounds containing the Nphosphonomethy1glycyl group.
N-Phosphonomethy1glycine (sometimes called glyphosate). together with analogous compoundsi their herbicidal properties and the formulations which contain themi are described in particular in US Patent 3,799.758. Although many glyphosate derivatives which are water-soluble or insoluble are known, It is in fact very generally preferred to employ the watersoluble derivativesi and this is why it is the Nphosphonomethylglycine salts which have been generally developed or commercialized, especially the isopropylammonium salt.
More recently (European Patent Application No. 290.416), attempts have been made to develop concentrates based on N-phosphonomethy1glycine salts, which may contain N-phosphonomethylglycine in acidic form. but,, in any event# containing this Nphosphonomethylglycine and/or Its derivatives in soluble or solubilized forms, the feature of these concentrates being the presence of an alkoxylated amine of a particular type. This alkoxylated amine must contain not more than 12 alkoxy groups per molecule and it must have the nature of a surface-active agent and it must promote the herbicidal activity 'of the 9 N-phosphonomethy1glycine derivatives. It can be employed in a smaller quantity than the known surfactants of the known N-phosphonomethy1glycine formulations. at least with regard to the production of concentrates intended to be applied in the open air. in the form of dilute slurries, at a rate of 100 to 600 llha. When the N-phosphonomethy1glycine-based compositions are compositions containing an ammonium salt such as ammonium sulphate, the ethoxylated amine used in this Patent 290,416 is, in fact, an ethoxylated amine containing only 2 ethoxy groups per molecule.
An objective of the present invention is to provide concentrated compositions or formulations (also called concentrates) based on N-phosphonomethy1glycine, is and especially based on its water-soluble salts.
Another objective of the present invention is to provide concentrates based on N phosphonomethy1glycine or on Its derivatives giving rise to dilute spraying mixtures which have a good herbicidal activity.
Another objective of the invention is to provide concentrates based on N-phosphonomethy1glycine salts using new types of surface-active agents promoting the biological activity.
Another objective of the Invention Is to provide concentrates based on N-phosphonomethy1glycine salts using surfactants which have a capability for improved solubilization.
Another objective of the invention is to provide concentrates based on Nphosphonomethy1glycine salts using new types of surface-active agents which are compatible in concentrated solutions with certain inorganic salts and especially with ammonium sulphate.
It has now been found that these objectives could be wholly or partially attained by virtue of the compositions according to the invention. In what follows the percentages are percentages by weight unless specifically stated. Furthermore. glyphosate equivalent is the name given to the corresponding quantity of product if all the N- phosphonomethy1glycine derivative was in the form of ordinary Nphosphonomethylglycine.
These compositions are liquid compositions consisting of aqueous solutions containing:
a) N-phosphonomethy1glycine and/or one of its derivatives in a proportion of at least 40 g/1 of glyphosate equivalent, b) a surfactant (having the nature of an activator) of formula (A0)n R' R - N CH2 -CH2 -CH2 -N (A0)n a R1 (A0) a - R1 in which R is a linear or branched, alkyl or alkenyl chain containing from 8 to 22 carbon atoms A denotes an alkylene group, preferably ethylene or propylene n, n' and nll are integers such that n + n' + nll is between 1 and 15, preferably 3 and 12 R' is the hydrogen atom or an acyl radical such as formyl, acetyl or propanoyl (that is to say CH3-CH2-CO).
Naturally, this single surfactant may be replaced by a mixture of surfactants in which, on average. R. n, n' and nu correspond to the definitions given above.
An N-phosphonomethy1glycine derivative means a compound containing the chain sequence -CO-CH2-N-CH2-p=0 (the nitrogen atom having a free valency and the phosphorus atom having two free valencies), preferably a salt, ester or amide, these terms being taken in the broad seneei for example so as to Include the sulphonamides.
The present invention advantageously relates to the concentrated compositions such as described above and additionally relating to one or other of the following features:
a) the N-phosphonomethy1glycine is in a quantity not exceeding the solubility limit in the medium in question, preferably between 60 and 200 g/1 and still more preferably between 90 and 150 g/lr b) the concentrated solution contains an ammonium (NH,) salt such as the nitrate, phosphate, sulphamate. thiocyanate or preferably the sulphate, in a proportion of 50 to 400 g/1, preferably 100 to 300 g/1, c) the concentrated compositions are intended to be diluted by the agriculturists in containers containing water so as to make it possible to spread these diluted spraying mixtures at a rate of 100 to 600 llha. the active substancei for its part, being applied at a rate of 0.125 to 4.5 kg/ha, is d) the weight ratio glyphosate equivalent/surfactant is between 0.6 and 6, preferably between 1 and 3, e) the solvent Is water.
The relatively high quantity of surfactant shown above relates to this surfactant with the nature of a biological activator/herbicide. it being understood that the compositions according to theinvention may additionally contain. as will be 1 explained later, all kinds of other components, and especially surfactants of the most diverse kinds and wetting in nature; these surfactants are then employed in dosages which are much lower than the activator dosage.
The concentrated liquid compositions according to the invention are usually prepared merely by mixing the constituents.
The compositions according to the invention usually contain from 5 to 25 % (preferably from 7 to 20 %) of active substances (herbicides), from 0.5 to 40 % (preferably from 10 to 20 %) of surface-active agent(s) of an activating nature. from 10 to 50 % (preferably from 20,to 30 %) of an ammonium salt is (adjuvant). from 0.1 to 10 % of surface-active agent(s) of a wetting nature, from 0 to 30 % of suitable additives such as foam suppressors, corrosion inhibitors. sequestrantsi stabilizers. penetrating agents or adhesives. The compositions according to the invention mayi of course, also contain all the solid or liquid additives corresponding to the usual techniques of making up a formulation.
According to what has already been said, the concentrated compositions according to the Invention may contain one or more surface-active agents besides the surfactant with an activating nature defined above. The surface-active agent employed may be a wetting agent of ionic or nonionic type or a mixture of such surface-active agents. There may be mentioned, for example, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (especially alkylphenols or arylphenols)r salts of esters of sulphosuccinic acidst taurine derivatives (especially alkyltaurates), phosphoric esters of ethylene oxide polycondensates with alcohols or phenols. esters of fatty acids and of polyols, and derivatives of the above compounds containing sulphate, sulphonate and phosphate functional groups.
In addition to N-phosphonomethy1glycine and/or its derivatives, the compositions used in the invention may contain other known active substances with herbicidal properties or with plant growth-regulating properties.
As herbicidal substance which may be mixed with the glyphosphate derivatives in the compositions according to the Invention there may be mentioned acifluorfen (or its sodium salt). aclonifen, bifenoxi diflufenican. asulam, triazines (especially simazine and atrazine)i diuron and oxadiazon. herbicides of hormone or phenoxy types. especially 2.4-D, [214-DB]r RUP,, hydroxybenzonitriles (especially bromoxynll and ioxynil). imidazolinones (especially imazaquin and Imazapur) and sulphonylureas (especially chlorsulfuron - 8 and metsulfuron). The above names are standardized names used to denote the herbicides.
In most cases these herbicides are employed In a proportion of 1 to 400 parts by weight per 100 parts of glyphosate or of glyphosate equivalent. By employing the term glyphosate equivalent the calculation of the parts is thus reduced as If all the glyphosate derivatives were in the form of Nphosphonomethylglycine.
More precisely, when herbicidal active substances other than glyphosate are employed and are mixed with glyphosate, the following proportions are generally used for the weight ratio wr: (wr is equal is glyphosate or glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate glyphosate to glyphosate equivalentlother acifluorfen: 4/100 diuron or oxadiazon: 2 s wr aclonifen: 1/3:s bifenox: 1/3 s diflufenican: 2:s wr asulam: 114 s phenoxy: 213:s hydroxybenzonitrile: 1!s wr triazine: 1/3 s imidazolinone: sulphonylurea:
W,r Wr:S Wr wr:s wr!s 10016 s herbicide) wr S 91100 4 s 10/3 S 1 20 1 4 10 S 1 4 wr:5 100 is As a general rule, the herbicidal compositions used in the invention usually contain approximately from 0.05 to 95 % of one or more herbicidal active substances, approximately from 1 % to 95 % of one or more liquid carriers and optionally approximately from 0.1 to 50 % of one or more surface-active agents.
Examples of solutions according to the invention and examples of use of these solutions are given below by way of an example given without any limitation being implied. The active substance in these examples is Nphosphonomethy1glycine in the form of isopropylammonium salt.
EXAMPLE 1 - N-Phosphonomethy1glycine in the form of isopropylammonium salt 100 g/1 - Ammonium sulphate 200 g/1 - Surfactant of formula defined below 100 g/1 - Water sufficient quantity for 1 1 The surfactant used in this example was a product of formula (CH2-CHz-0)n H Cia H35- N with n + n 1 + n 11 = 3 is (CH2-CH2-0)n. H CH2 -CH2 -CH2 -N (CH2 -CH2 -0)n., H EXAMPLE 2
N-Phosphonomethyl.glycine, in the form of isopropylammonium salt Ammonium sulphate Surfactant employed in Example 1 Water sufficient quantity for EXAMPLE 3
N-Phosphonomethy1glycine in the form of Isopropylammonium salt Ammonium sulphate Surfactant employed In Example 1 Water sufficient quantity for EXAMPLE 4
N-Phosphonomethy1glycine in the form of Isopropylammonium salt Ammonium sulphate g/1 100 g/1 200 g/1 1 1 g/1 150 g/1 150 g/1 1 1 g/1 300 g/1 Surfactant employed in Example 1 100 g/1 Water sufficient quantity for 1 1 EXAMPLE 5
N-Phosphonomethy1glycine in the form of isopropylammonium salt 100 g/1 Acifluorfen In the form of sodium salt 4.5 g/1 Amonium sulphate 200 g/1 Surfactant of the formula defined above with n + n' + nll = 10 Water sufficient quantity for 1 1 These solutions are diluted in water in a proportion of 2.5 and 5 1 in 300 1 and the spraying mixtures thus obtained are sprayed onto various adventitious plants.
The compositions of Examples 1 to 4. employed in the dosage of 250 9/1 of active substance calculated in the form of N-phosphonomethy1glycine, exhibit an effectiveness on various weeds, especially morning glory. purslane and Indian mallow, which is markedly superior to that of commercial products. and especially of the product marketed under the trademark Round-up and which contains the same active substance In combination with ordinary surface-active agents.

Claims (23)

- 12 CLAIMS
1. A liquid herbicidal composition which comprises an aqueous solution containing:
a) N-phosphonomethy1glycine and/or one of its derivatives in a proportion of at least 40 g/1 of 5 glyphosate equivalent, and b) a surfactant of formula AO) n R1 R - N CH2-CH2-CH2-N (A0) n 1 R1 (A0) n't R1 in which R is a linear or branched, alkyl or alkenyl chain containing from 8 to 22 carbon atoms A denotes an alkylene group.
is n, n' and nll are integers such that n + n' + nll is from 1 to 15 Each R1, which may be the same or different is hydrogen or an acyl radical.
2. The composition according to claim 1, wherein A 20 is an ethylene or propylene group.
3. The composition according to claim 1 or 2, wherein n + n' + nll is between 3 and 12.
4. The composition according to any one of claims 1 to 3, wherein R1 is a formyl, acetyl or propanoyl radical, preferably acetyl. -
5. The composition according to any one of claims 1 to 4, wherein the Nphosphonomethy1glycine and/or one of its derivatives is in a quantity not exceeding the solubility limit in the medium in question and is from 60 to 200 g/1.
6. The composition according to any one of claims 1 to 5, wherein the Nphosphonomethy1glycine and/or one of its derivatives is in a quantity of from 90 to 150 g/1.
7. The composition according to any one of claims 1 to 6, wherein the concentrated solution contains an ammonium salt such as the nitrate, phosphate, sulphamate, thiocyanate or preferably the sulphate, in a proportion of 50 to 400 g/1.
8. The composition according to any one of claims 1 to 7, wherein the concentrated solution contains an ammonium salt in a proportion of 100 to 300 g/1.
9. The composition according to any one of claims 1 to 8, which is intended to be diluted in water so as to make it possible to spread these diluted spraying mixtures at a rate of 100 to 600 1/ha, the active substance, for its part, being applied at a rate of 0.125 to 4.5 kg/ha.
10. The composition according to one of claims 1 to 9, wherein the weight ratio glyphosate equivalent/surfactant is from 0.6 to-6.
11. The composition according to claim 10, wherein the weight ratio is from 1 to 3.
12. The composition according to any one of claims 1 to 11, wherein the solvent is water.
13. The composition according to any one of claims 1 to 12, which comprises other surfactants of a wetting nature and optionally one or more other additives selected from foam supressors, corrosion inhibitors, sequestrants, stabilizers, penetrating agents or adhesives.
14. The composition according to any one of claims 1 to 13, which comprises from 5 to 25 of herbicidal active substance, from 0.5 to 40 of surfaceactive agent(s) of an activating nature, from 10 to 50 % of an ammonium salt (adjuvant), from 0.1 to 10 % of surfaceactive agent(s) of a wetting nature, and from 0 to 30 of other additives.
15. The composition according to any one of claims 1 to 14, which comprises from 7 to 20 of herbicidal active substance, from 10 to 20 % of surfaceactive agent(s) of an activating nature, and from 20 to 30 % of ammonium salt.
16. The composition according to any one of claims 1 to 15, which comprises at least one other - 15 herbicide in addition to N-phosphonomethy1glycine and/or one of its derivatives.
17. The composition according to claim 16 wherein the other herbicide chosen from the group consisting of: 5 acifluorfen (or its sodium salt), aclonifen, bifenox, diflufenican, asulam, triazines (especially simazine and atrazine), diuron and oxadiazon, herbicides of hormone or phenoxy types, especially 2,4-D, [2,4-DB], MCPP, hydroxybenzonitriles (especially bromoxynil and ioxynil), 10 imidazolinones (especially imazaquin and imazapur) and sulphonylureas (especially chlorsulfuron and metsulfuron).
18. The composition according to claim 17, wherein the said other herbicides are present in the following weight ratio wr:
(wr is equal to glyphosate or glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + 25 glyphosate + glyphosate + glyphosate equivalent/other herbicide) acifluorfen: 4/100 5 wr 5 9/100 diuron or oxadiazon: 2 5 wr:5 4 aclonifen: 1/3 5 wr 5 10/3 bifenox: 1/3 5 wr 5 1 diflufenican: asulam: phenoxy: hydroxybenzonitrile: triazine: imidazolinone:
2 5 wr 5 l/ 4:5 wr 2/3 5 wr 1 5 wr 5 1/3 5 wr 1 5 wr 5 20:5 1:5 4 10:S 1 4 - 16 glyphosate + sulphonylurea: 100/6:5 wr 5 100.
19. The composition according to one of claims 16 to 18, which comprises acifluorfen or its sodium salt.
20. The composition according to claim 1 5 substantially as hereinbefore described.
21. A process for combating weeds, in which a composition according to one of claims 1 to 20 is employed.
22. The process according to claim 21, wherein the said composition is diluted and applied at a rate of 100 to 600 1/ha, the active substance being applied at a rate of 0.125 to 4.5 kg/ha.
23. The process according to claim 21 or 22 substantially as hereinbefore described.
1001 tlh. Pt-t Offire- state House. 66171 High Holborn. London WC1R4TP. Further copies may be obtained from Th,Eatent Office.
GB9013692A 1989-06-20 1990-06-20 Herbicidal compositions based on n-phosphonomethylglycine Expired - Lifetime GB2233229B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8908433A FR2648316A1 (en) 1989-06-20 1989-06-20 HERBICIDE COMPOSITIONS BASED ON N-PHOSPHONOMETHYLGLYCIN AND THEIR USE

Publications (3)

Publication Number Publication Date
GB9013692D0 GB9013692D0 (en) 1990-08-08
GB2233229A true GB2233229A (en) 1991-01-09
GB2233229B GB2233229B (en) 1992-05-06

Family

ID=9383094

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9013692A Expired - Lifetime GB2233229B (en) 1989-06-20 1990-06-20 Herbicidal compositions based on n-phosphonomethylglycine

Country Status (18)

Country Link
JP (1) JPH0334901A (en)
KR (1) KR910000016A (en)
AU (1) AU5756590A (en)
BR (1) BR9002986A (en)
CA (1) CA2019087A1 (en)
DE (1) DE4019362A1 (en)
DK (1) DK149390A (en)
FR (1) FR2648316A1 (en)
GB (1) GB2233229B (en)
GR (1) GR900100459A (en)
HU (1) HUT54023A (en)
IE (1) IE902130A1 (en)
IT (1) IT1248734B (en)
LU (1) LU87747A1 (en)
NL (1) NL9001407A (en)
PT (1) PT94414A (en)
SE (1) SE9002166L (en)
ZA (1) ZA904785B (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019941A1 (en) * 1993-03-09 1994-09-15 Kvk Agro A/S A herbicide preparation, a process for producing it and an activating additive for application therewith
WO1995003697A1 (en) * 1993-07-28 1995-02-09 Kemira Oy Herbicide composition, activity-promoting agent for improving the efficacy of the herbicide, and a method for treating cultivated plants
US6127317A (en) * 1997-09-17 2000-10-03 American Cyanamid Company Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt
US6214768B1 (en) 1998-09-14 2001-04-10 American Cyanamid Co. Synergistic herbicidal methods and compositions
US6239072B1 (en) * 1998-03-09 2001-05-29 Monsanto Company Tank mixtures and premixtures for weed control programs that include postmergence applications of glyphosate plus graminicides in glyphosate tolerant soybeans
US6277787B1 (en) 1998-09-14 2001-08-21 American Cyanamid Co. Synergistic herbicidal methods and compositions
US6420311B1 (en) 1999-08-18 2002-07-16 Huntsman Petrochemical Corporation Polyether diamine—based surfactant adjuvants and compositions thereof
US6436874B1 (en) 1998-04-08 2002-08-20 Aventis Cropscience Gmbh Synergistic herbicidal agents based on leaf herbicides containing phosphorus, imidazolinones and hormone weed killers
US6586367B2 (en) 1996-09-05 2003-07-01 Syngenta Crop Protection, Inc. Process for the control of weeds
US7135437B2 (en) 2000-05-19 2006-11-14 Monsanto Technology Llc Stable liquid pesticide compositions
WO2011009171A1 (en) * 2009-07-22 2011-01-27 Huntsman Corporation Australia Pty Limited Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions
US8293683B2 (en) 2006-12-06 2012-10-23 Akzo Nobel N.V. Alkylamidopropyl dialkylamine surfactants as adjuvants
EP1721523A3 (en) * 2000-05-19 2013-01-23 Monsanto Technology, LLC Aqueous pesticide formulations and novel surfactants
US9012365B2 (en) 2006-12-06 2015-04-21 Akzo Nobel N.V. Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962371A (en) * 1995-02-13 1999-10-05 Novartis Crop Protection, Inc. Herbicidal composition and method of controlling weeds
FR2737390B1 (en) * 1995-08-04 1997-09-19 Rhone Poulenc Chimie WATER-SOLUBLE PHYTOSANITARY COMPOSITION COMPRISING AT LEAST POLYACOXYLATED AMIDOAMINES
AUPO405696A0 (en) 1996-12-06 1997-01-09 Ici Australia Operations Proprietary Limited Herbicidal compositions
AU746589B2 (en) * 1997-07-30 2002-05-02 Monsanto Company Process and compositions promoting biological effectiveness of exogenous chemical substances in plants
FR2766669B1 (en) * 1997-07-30 1999-10-29 Flamel Tech Sa GLYPHOSATE EMULSION, ONE OF ITS PREPARATION METHODS, AND PHYTO-TOXIC COMPOSITION CONTAINING THE SAME
TW471950B (en) * 1997-09-17 2002-01-11 American Cyanamid Co Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt
DE19836684A1 (en) * 1998-08-13 2000-02-17 Hoechst Schering Agrevo Gmbh Use of a synergistic herbicidal combination including a glufosinate- or glyphosate-type, imidazolinone or protoporphyrinogen oxidase to control weeds in rice
US6992045B2 (en) 2000-05-19 2006-01-31 Monsanto Technology Llc Pesticide compositions containing oxalic acid
NZ529552A (en) * 2001-05-21 2006-07-28 Monsanto Technology Llc Pesticide concentrates containing etheramine surfactants
ES2323768T3 (en) * 2001-06-01 2009-07-24 Huntsman Petrochemical Corporation ADJUSTMENT AND PESTICIDE COMPOSITIONS.
DE10250551A1 (en) * 2002-10-30 2004-05-19 Clariant Gmbh Pesticide formulations containing alkoxylated amines
DE10250552A1 (en) * 2002-10-30 2004-05-19 Clariant Gmbh Pesticide formulations containing alkoxylated amines

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0290416A2 (en) * 1987-04-29 1988-11-09 Monsanto Europe S.A./N.V. Improved glyphosate formulations

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4528023A (en) * 1983-07-25 1985-07-09 Stauffer Chemical Company Enhancement of herbicidal activity of tetraaluminum salts of N-phosphonomethylglycine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0290416A2 (en) * 1987-04-29 1988-11-09 Monsanto Europe S.A./N.V. Improved glyphosate formulations

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU685437B2 (en) * 1993-03-09 1998-01-22 Kvk Agro A/S A herbicide preparation, a process for producing it and an activating additive for application therewith
US5795847A (en) * 1993-03-09 1998-08-18 Kvk Agro A/S Herbicide preparation, a process for producing it and an activating additive for application therewith
US6180566B1 (en) 1993-03-09 2001-01-30 Kvk Agro A/S Herbicide preparation, a process for producing it and an activating additive for application therewith
WO1994019941A1 (en) * 1993-03-09 1994-09-15 Kvk Agro A/S A herbicide preparation, a process for producing it and an activating additive for application therewith
WO1995003697A1 (en) * 1993-07-28 1995-02-09 Kemira Oy Herbicide composition, activity-promoting agent for improving the efficacy of the herbicide, and a method for treating cultivated plants
US7407913B2 (en) 1996-09-05 2008-08-05 Syngenta Crop Protection, Inc. Process for the control of weeds
US6586367B2 (en) 1996-09-05 2003-07-01 Syngenta Crop Protection, Inc. Process for the control of weeds
US6127317A (en) * 1997-09-17 2000-10-03 American Cyanamid Company Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt
US6239072B1 (en) * 1998-03-09 2001-05-29 Monsanto Company Tank mixtures and premixtures for weed control programs that include postmergence applications of glyphosate plus graminicides in glyphosate tolerant soybeans
US6436874B1 (en) 1998-04-08 2002-08-20 Aventis Cropscience Gmbh Synergistic herbicidal agents based on leaf herbicides containing phosphorus, imidazolinones and hormone weed killers
US6214768B1 (en) 1998-09-14 2001-04-10 American Cyanamid Co. Synergistic herbicidal methods and compositions
US6277787B1 (en) 1998-09-14 2001-08-21 American Cyanamid Co. Synergistic herbicidal methods and compositions
US6420311B1 (en) 1999-08-18 2002-07-16 Huntsman Petrochemical Corporation Polyether diamine—based surfactant adjuvants and compositions thereof
US7135437B2 (en) 2000-05-19 2006-11-14 Monsanto Technology Llc Stable liquid pesticide compositions
EP1721523A3 (en) * 2000-05-19 2013-01-23 Monsanto Technology, LLC Aqueous pesticide formulations and novel surfactants
US8293683B2 (en) 2006-12-06 2012-10-23 Akzo Nobel N.V. Alkylamidopropyl dialkylamine surfactants as adjuvants
US9012365B2 (en) 2006-12-06 2015-04-21 Akzo Nobel N.V. Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts
WO2011009171A1 (en) * 2009-07-22 2011-01-27 Huntsman Corporation Australia Pty Limited Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions
CN102469778A (en) * 2009-07-22 2012-05-23 胡茨曼澳大利亚股份有限公司 Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions
EP2456302A1 (en) * 2009-07-22 2012-05-30 Huntsman Corporation Australia Pty Limited Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions
EP2456302A4 (en) * 2009-07-22 2013-07-24 Huntsman Corp Australia Pty Ltd Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions
AU2010276088B2 (en) * 2009-07-22 2014-10-23 Indorama Ventures Oxides Australia Pty Limited Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions
CN102469778B (en) * 2009-07-22 2015-09-09 胡茨曼澳大利亚股份有限公司 Cocoalkyl polyamines alcoxylates is as the reagent for high strength Herbicidal combinations
US9578877B2 (en) 2009-07-22 2017-02-28 Huntsman Corporation Australia Pty Limited Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions

Also Published As

Publication number Publication date
HU903921D0 (en) 1990-11-28
PT94414A (en) 1991-02-08
IE902130L (en) 1990-12-20
IE902130A1 (en) 1991-01-02
IT9020701A0 (en) 1990-06-20
KR910000016A (en) 1991-01-29
GR900100459A (en) 1991-11-15
FR2648316A1 (en) 1990-12-21
IT1248734B (en) 1995-01-26
SE9002166D0 (en) 1990-06-18
JPH0334901A (en) 1991-02-14
HUT54023A (en) 1991-01-28
DK149390D0 (en) 1990-06-19
LU87747A1 (en) 1991-02-18
BR9002986A (en) 1991-08-20
NL9001407A (en) 1991-01-16
DK149390A (en) 1990-12-21
AU5756590A (en) 1991-01-03
IT9020701A1 (en) 1991-12-20
CA2019087A1 (en) 1990-12-20
DE4019362A1 (en) 1991-01-03
GB9013692D0 (en) 1990-08-08
ZA904785B (en) 1991-04-24
SE9002166L (en) 1990-12-21
GB2233229B (en) 1992-05-06

Similar Documents

Publication Publication Date Title
GB2233229A (en) Concentrated herbicidal compositions based on N-phosphonomethylglycine
EP0506788B1 (en) A herbicidal formulation containing glyphosate acid
KR0159995B1 (en) Herbicidal compositions comprising glyphosates and alkoxylated quaternary amine surfactants
RU2190329C2 (en) Herbicide compositions, method for elimination and suppression of weeds or undesired plants
JP3117088B2 (en) Aqueous concentrated formulation with little irritation to eyes
AU2008324145B2 (en) Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a viscosity reducing agent
AU641761B2 (en) Herbicidal solutions based on N-phosphonomethylglycine
US20080312083A1 (en) Herbicidal Composition Comprising and Aminophosphate or Aminophosphonate Salt and a Betaine
IE66599B1 (en) Defoamer for liquid wetting agents and low-foam liquid plant protection agents
PL187018B1 (en) Herbicidal composition
US5703016A (en) Surfactant composition for use with glyphosate comprising dimethyl amine oxide, polyethoxylated alcohol, and pyridinium halide
CA2015797A1 (en) Concentrated liquid compositions based on n-phosphonomethylglycine
JP4018753B2 (en) Herbicidal composition
PL210284B1 (en) Low foaming formulation of glyphosate
US5710104A (en) Glyphosate compositions comprising polyethoxylated monohydric primary alcohols
US5362705A (en) Herbicidal formulations containing n-phosphonomethylglycine and alkyl phenol polyoxyalkylene carboxylic acid surfactant
JP4323800B2 (en) Herbicidal composition
AU749008B2 (en) Phytosanitary formulations with high active substance content
US5679621A (en) Herbicidal and plant growth regulant compositions and their use

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940620