WO1996008150A1 - Compositions de micro-emulsions pesticides aqueuses - Google Patents

Compositions de micro-emulsions pesticides aqueuses Download PDF

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Publication number
WO1996008150A1
WO1996008150A1 PCT/US1995/011135 US9511135W WO9608150A1 WO 1996008150 A1 WO1996008150 A1 WO 1996008150A1 US 9511135 W US9511135 W US 9511135W WO 9608150 A1 WO9608150 A1 WO 9608150A1
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Prior art keywords
ethoxylated
weight
microemulsion
alkyl
acid
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Application number
PCT/US1995/011135
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English (en)
Inventor
Mohamed A. Mostafa
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Akzo Nobel N.V.
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Publication of WO1996008150A1 publication Critical patent/WO1996008150A1/fr

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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
    • A01N25/02—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

Definitions

  • the present invention relates to aqueous based pesticidal microemulsion and to methods for preparing same.
  • Microemulsions are a unique class of thermodynamically stable mixtures of water, oil (pesticidal actives) and surface active agents in one phase which are an attractive alternative to EC's because of their increased stability, lack of organic solvent and ease of use. Microemulsions form spontaneously and are indefinitely storage stable. As a rule, however, microemulsions are difficult to formulate and are obtainable only with certain surfactant combinations and only within specific finite concentrations of these surfactant combinations. U.S.
  • composition of matter and a method of treating agricultural substrates in which an active ingredient, which may be a herbi ⁇ cide, is utilized in conjunction with an amount of a glycoside dispersing agent selected from the group consisting of fructo- side, glucoside, annoside, galactoside, taloside, guloside, alloside, altroside, idoside, arabinside, xyloside, lyxoside and riboside and mixtures thereof in an amount sufficient to form an emulsion or dispersion of the active ingredient.
  • a glycoside dispersing agent selected from the group consisting of fructo- side, glucoside, annoside, galactoside, taloside, guloside, alloside, altroside, idoside, arabinside, xyloside, lyxoside and riboside and mixtures thereof in an amount sufficient to form an emulsion or dispersion of the active ingredient.
  • U.S. Patent No. 5,227,402 describes plant protection agents based on aqueous microemulsions which contain, as emulsifiers, ethoxylated and phosphorylated, styryl-substituted phenols or salts thereof in combination with one or more non-phosphorylated emulsifiers belonging to the group comprising salts of (C 10 -C 16 )- alkyl-monoglycol to -hexaglycol ether-sulfates, salts of ⁇ -(C u - C 19 )-alkenol sulfates, salts of optionally chlorinated (C 13 - C 18 ) alkanesulfonic acids, salts of dodecylphenylsulfonic acid, amine oxethylates or ⁇ (C 9 -C 20 )-alkyl-fo-hydroxypolyoxylethylenes contain ing 2 to 22 moles of ethylene oxide.
  • EP 0 371 212 describes aqueous herbicidal microemulsions containing l,2-dimethyl-3,5 diphenylpyrazolium (difenzoquat) , an essentially water insoluble active ingredient and a nonionic surfactant.
  • GB 2,089,914 is directed to aqueous phenoxy emulsions which comprise 30-75% by weight of one or more herbicidally-active phenoxyalkanecarboxylic acid esters, 1.01 to 11.1 parts by weigh per 100 parts of ester of oil-soluble emulsifiers which are soluble in the esters and have an HLB value of 9 to 16, and one or more ionic or nonionic water-soluble dispersants.
  • GB 2,115,285 describes emulsions similar to those described in GB 2,089,914 with the exception that the emulsion of GB 2,115,285 additionally comprises 0.1 to 3 parts by weight of one or more alkali metal salts of single or multiple unsaturated fatty acid taurides or fatty acid alkyl taurides as water soluble dispersants.
  • the object of the present invention is to provide icroemulsion formulations which are comparable to emulsifiable concentrate systems but which do not contain undesirable aromat ⁇ ic, hydrocarbon solvents.
  • a further object is to provide aqueous based microemulsions which are environmentally acceptable and uniquely stable.
  • Another object of the present invention is to provide a surfactant package which allows one to prepare highly concentrated, stable, aqueous microemulsions and promotes the efficacy of the herbicidal actives in said microemulsions which leads to reduced application rates.
  • the present invention generally relates to an aqueous based pesticidal microemulsion formulation which comprises a pesticid ⁇ ally active compound, a surfactant mixture and water, wherein said surfactant mixture comprises an ethoxylated acid, an alkyl polycoside, an ethoxylated castor oil, optionally, an ethoxylated alkyl phenyl phosphate and a cosurfactant; the remainder being water.
  • the present invention also relates to methods of preparing said microemulsions. Detailed Description of the Invention
  • the present invention relates to aqueous-based pesticidal microemulsions which comprise at least one pesticidally active compound, a surfactant mixture and water, wherein said surfactant mixture comprises at least one ethoxylated acid, at least one alkyl polycoside, at least one ethoxylated castor oil, optionally at least one ethoxylated alkyl phenyl phosphate and a least one cosurfactant.
  • the present invention also relates to a surfactant mixture useful in formulating said microemulsions, wherein said surfactant mixture comprises at least one ethoxylated acid, at least one alkyl polycoside, at least one ethoxylated castor oil, optionally at least one ethoxylated alkyl phenyl phosphate and a least one cosurfactant.
  • the concentrated microemulsion of the present invention generally comprises from about 1 to 98% by weight actives, from about 3 to 40% surfactant mixture, and water to 100%.
  • the present microemulsion preferably comprises from about 20 to 95% by weight actives, from 5 to 35% by weight surfactant mixture, and water to 100%.
  • the microemulsion of the present invention comprises from about 35% to about 85% by weight actives, from 10 to 30% by weight surfactant mixture, and water to 100%.
  • the concentrated microemulsion of the present invention is diluted with water to the desired dilution level application rate.
  • the concentrated microemulsion of the present invention is diluted with water to yield an aqueous- based microemulsion containing from about 0.05 to about 50% by weight pesticidal active, more preferably from about 1 to 35% by weight actives, and still more preferably from about 1.5 to 30% actives.
  • the diluted microemulsions range in opacity from clear to milky depending on the weight % of the actives in the concentrate.
  • Actives which can be employed in the microemulsion of the present invention include but are not limited to insecticides, nematicides, herbicides, fungicides, plant growth regulators and combinations thereof.
  • Pesticidal actives which can be employed in the context of the present invention include phenoxy-type (e.g., 2,4-D), dinitro-type (e.g. trifluralin) , amide-type (e.g. propanil) , organo phosphate-type (e.g., azinophes-methyl) , urea-type (e.g., diuron) , triazine type (e.g., atrazine) , uracil-type (e.g., bromacil) , sulfonyl urea-type (e.g., nicosulfuron) , benzoic-type (e.g., dicamba) , diaryl ether-type (e.g., fluazifop-butyl) and nitrile-type (e.g., bromoxynil) pesticides, along with triazole- based fungicides such as azaconazole.
  • pesticidal actives which are preferred include but are not limited to esters of 4-chloro-2-methylphenoxy-acetic (MCPA) acid bromoxynil esters and esters of 2,4-dichlorophenoxy acetic acid (2,4-D), as well as acetochlor, bupirimate, butylate, chlorbufam, flurochloridone, esters of 2,4-DB acid, any dichlorprop ester, any fenoprop ester, fenpropimorph, fluoroglycofen-ethyl, fluroxpyr, ioxynil esters, esters of MCPB, mecoprop esters, metolachlor, molinate, propiconazole, pyridate, sethoxydim, 2,4,5-T ester, tebutam, triclopyr, azaconazole, triadimefon, thidiazuron, prometryn, bentazon, lactofen, acifluorin sodium, fomesuf
  • Especially preferred active ingredients are essentially water insoluble and include: straight or branched C 4 -C 10 alkyl esters of 2,4-D acid and mixtures thereof; straight or branched C 4 -C 10 alkyl esters of MCPA acid and mixtures thereof; and/or bromoxynil esters of straight or branched C 4 -C 10 alkanoic acids and mixtures thereof.
  • the isooctyl ester of 2,4-D acid, C 4 Hc, esters (mixed butyl esters) of MCPA acid and bromoxynil octanoat or mixtures thereof are especially preferred. In some circumstances, desirable results can be obtained by utilizing a combination of both the ester form of the pesticidal active and its parent acid.
  • Aqueous formulations of these pesticidally active ingredi- ents are normally prepared using the salts of these compounds which are water soluble, and not the esters. However, it has been found in some instances that an ester can be more effective because many of these essentially water insoluble pesticidally active ingredients are normally applied post-emergence to the foliage of the undesirable plant and the leaf penetration proper ties of the pesticide can be advantageously altered using variou lipophilic esters and/or acids of these pesticides.
  • the ethoxylated acid of the surfactant mixture of the present invention preferably contains from about 2 to 22 moles o ethylene oxide.
  • An ethoxylated oleic acid having from 2 to 22 moles of ethylene oxide is a preferred example.
  • Examples of preferred ethoxylated acids include Ethofat*0/15 and Ethofat*242/25 both of which are sold by Akzo Nobel Chemicals, Inc.
  • the surfactant mixture of the microemulsion of the present invention generally comprises from about 0.5 to 40% by weight ethoxylated acid. Still more preferred, said microemulsion contains from 1 to 30% and still more preferred 1.5 to 25% by weight ethoxylated acid.
  • Alkyl polycosides useful in the surfactant mixture of present invention include those prepared in accordance with U.S. Patent Numbers 3,219,656 and 3,598,865, which are incorporated herein by reference.
  • the alkyl polycosides of the present invention generally comply with the following general formula:
  • R (OG)x wherein R contains from 1 to about 30 carbon atoms, G is the saccharide backbone (glycosyl) of the molecule and x, which refers to the degree of saturation, is from 1 to 18.
  • Useful saccharide moieties for the glycoside include, but are not limited to fructosides, mannosides, glucosides, talosides, galactosides, gulosides, allosides, altrosides, idosides, anabinosides, lyxoside, xylosides, ribosides and mixtures there ⁇ of.
  • Preferred saccharide moieties include glucosides, xylosides and fructosides.
  • Glycoside*APG 325 (C 9 -C ) which can be pur ⁇ chased from Henkel Corporation is an alkyl polycoside which is preferably employed in the surfactant mixture of the present microemulsion. Also suitable for use in the present invention is Berol AE6202 which is an alkyl polyglycoside which can be purchased from Akzo Nobel Chemicals, Inc.
  • the surfactant mixture of the present invention generally contains from about 0.1 to about 20% by weight alkyl polycoside. Still more preferred, from about 1.0 to 15% by weight alkyl polycoside is employed.
  • the surfactant mixture also comprises from about 0.1 to about 45% by weight of ethoxylated castor oil, and still more preferred, from about 2 to 25% by weight.
  • Preferred ethoxylated castor oils have from between about 5 to 55 moles of ethylene oxide chemically combined with each mole of castor oil. Particu ⁇ larly good results are obtained with Alkamuls* EL 620 (30 EO) which is manufactured by Rhone Poulenc, and Berol 106 which is available from Akzo Nobel Chemicals, Inc.
  • Suitable ethoxylated alkyl phenyl phosphates are styryl- containing ethoxylated and phosphorylated phenols and more preferred, phenols of this type having three styrene radicals and approximately 16 to 20 moles of ethylene oxide.
  • Soprophore 3D33 ethoxylate tristysol phenol phosphate
  • Rhone Poulenc is a preferred ethoxylated alkyl phenol phosphate.
  • the surfactant package of the present invention comprises from about 0 to about 25% by weight of ethoxylated alkyl phenol phosphate is incorporated into the surfactant mixture of the present invention.
  • a more preferred range of alkyl phenyl phosphate is between about 2 to about 15 wt%.
  • the surfactant mixture of the present invention comprises from about .1 to 45% by weight, and more preferably, from about to about 25% cosurfactant.
  • Preferred cosurfactants are usually medium chain fatty alcohols, acids or amines.
  • the cosurfactant is preferably an alcohol of the formula R-OH wherein R is a straight or branched chain alkyl with 4 to 10 carbon atoms.
  • Especially preferred cosurfactants are alcohols of the above formula wherein the R group is a straight chain alcohol containing from 5 to 8 carbon atoms. Examples of preferred alcohols are pentanol, hexanol, heptanol octanol and mixtures thereof, with hexanol being the most preferred.
  • the present invention relates to an aqueous herbicidal microemulsion which comprises at least one herbicidally active component, a surfactant mixture and water, wherein comprises said surfactant mixture comprising of 0.5 to 40% by weight of an ethoxylated acid, 0.1 to 20% by weight of an alkyl polycoside, 0.1 to 45% by weight of an ethoxylated castor oil, 0 to 25% by weight of an ethoxylated alkyl phenyl phosphate and a cosurfactant; and water to 100%.
  • the aqueous-based herbicidal microemulsion of the present invention comprises from 1 to 98% herbicidal actives; from 3 to 40% surfactant mixture and the remainder water; wherein said herbicidally active material is selected from 2,4-D iso octyl ester, MCPA, trifluralin, propanil and mixtures thereof; and said surfactant mixture comprises of 0.5 to 40% by weight ethoxylated oleic acid; 0.5 to 20% by weight alkyl polycoside; .5 to 35% by weight of an ethoxylated castor oil; 0 to 15% by weight of an ethoxylated alkyl phenyl phosphate, and an alcohol as a cosurfactant; the remainder being water.
  • said herbicidally active material is selected from 2,4-D iso octyl ester, MCPA, trifluralin, propanil and mixtures thereof
  • said surfactant mixture comprises of 0.5 to 40% by weight ethoxylated
  • the aqueous-based herbicidal microemulsion of the present invention comprises from 35 to 98% herbicidal actives; from 3 to 40% surfactant mixture and the remainder water; wherein said herbicidally active material is selected from 2,4-D iso octyl ester, MCPA and mixtures thereof; and said surfactant mixture comprises of 1 to 30% by weight ethoxylated oleic acid; 1 to 25% by weight alkyl polycoside; 2 to 25% by weight of ethoxylated castor oil; 2 to 15% by weight of an ethoxylated alkyl phenyl phosphate, and 0.1 to 40% by weight hexanol as a cosurfactant; the remainder being water.
  • said herbicidally active material is selected from 2,4-D iso octyl ester, MCPA and mixtures thereof
  • said surfactant mixture comprises of 1 to 30% by weight ethoxylated oleic acid; 1 to 25% by weight alkyl polycoside
  • the microemulsion of the present invention comprises from 50 to 98% herbicidal actives; from 3 to 40% surfactant mixture, and the remainder water; wherein said herbicidally active material is selected from 2,4-D iso octyl ester, MCPA and mixtures thereof; and said surfactant mixture comprises of 1.5 to 15% by weight Ethofat* 242/25; 5 to 20% by weight Glycoside* APG-325; 5 to 20% by weight Alkamuls*EL- 620; 2 to 15% by weight Soprophore* 3D33, and 1 to 25% by weight hexanol as a cosurfactant; the remainder being water.
  • said herbicidally active material is selected from 2,4-D iso octyl ester, MCPA and mixtures thereof
  • said surfactant mixture comprises of 1.5 to 15% by weight Ethofat* 242/25; 5 to 20% by weight Glycoside* APG-325; 5 to 20% by weight Alkamuls*EL- 620; 2 to 15% by weight
  • the nature and stability of pesticidal microemulsions are influenced by the structure and chain length of the surfactant(s) and the structure of the cosurfactant. For example, solubilization increases with increase of ethoxylated alkyl phenols with same HLB. Also, solubilization increases with less branching of the hydrocarbon tail. So the relative stability of the microemulsion depends on the relative packing of the hydrophobic/hydrophilic portions of the surfactant molecule(s), which determines the bending of the interface.
  • the stable microemulsion concentrate of the present invention shows no sign of crystallization, salting-out or partition dissolution upon storing under adverse conditions ranging from -40'to 50*C, which is a considerable improvement over their EC counterparts which typically show physical instability under similar conditions.
  • a water dilution of the concentrate generally yields solubilized particles of less than about one (1) micron. This small particle size (non-gravity controlled) is advantageous in that it eliminates larger particl deposits on screens of spray application nozzles or settling out on standing due to gravity. Further, the water-based microemulsions of the present invention are more environmentally acceptable than their EC counterparts which require the use of solvents.
  • the pesticides are added to and mixed with a portion of the surfactants at a temperature of from about 30 - 70°. This is followed by incorporating the balance of the surfactants (some formulations contain Calcium Dodecyl Benzene Sulfonate) and the cosurfactant while maintaining the same temperature.
  • all surfactants, cosurfactant(s) and th pesticide(s) are blended together at a temperature of from about 30 -70°.
  • the dilution ranges from clear (transparent) to translucent-to-milky appearance depending on the original level of the pesticide(s) in the concentrated formulation. The lower the level of the pesticide, the clearer the diluent.
  • Step one The water insoluble pesticide(s) are mixed with the water-soluble surfactant, ethoxylated alkyl phenol phosphate and kept warm by a water bath maintained at 55°C.
  • Step two While maintaining the 55"C temperature, a preblend of all other surfactants (ethoxylated acid, alkyl polyglycoside, ethoxylated oil and the cosurfactant, hexyl alcohol) is added to the mixture of step one, and mixing is allowed to continue for 20-30 minutes.
  • surfactants ethoxylated acid, alkyl polyglycoside, ethoxylated oil and the cosurfactant, hexyl alcohol
  • the pesticide(s) are added to a preblend of all surfactants and cosurfactant. Allow mixing to continue for 20-30 minutes in a water bath maintained at 55 ⁇ C. (II. TYPICAL FORMULATIONS
  • composition 40% Wt 70% Wt 90% wt 96% wt**
  • Example 1 The exact procedure of Example 1 was utilized with the exceptio that 40g of technical MCPA was employed as the active ingredien
  • microemulsion-solubilized formulations of 70% and higher including those of Examples 3-6 exhibited the following properties: 1. Clear amber liquids as concentrates. Upon adding water of different hardness to the concentrated formulations, milky dilutions are generated. No settling or separation was observed after 24 hours.
  • a particle size ranging from between 0.4-0.9 micron.
  • microemulsion of Trifluralin does not survive freezing which is a common characteristic of formulations which incorporate the dinitro-class of pesticides.

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  • 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)
  • Toxicology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne en général une composition de micro-émulsion pesticide aqueuse qui comprend un composé à action pesticide, un mélange tensioactif et de l'eau, ledit mélange tensioactif comprenant un acide éthoxylé, un polycoside d'alkyle, une huile de ricin éthoxylée, éventuellement, un phosphate de phényle d'alkyle éthoxylé et un co-tensioactif, le reste étant de l'eau. L'invention concerne également des procédés de production de telles micro-émulsions.
PCT/US1995/011135 1994-09-15 1995-09-01 Compositions de micro-emulsions pesticides aqueuses WO1996008150A1 (fr)

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US08/306,356 1994-09-15

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998028976A1 (fr) * 1996-12-30 1998-07-09 Rhodia Inc. Composition adjuvante pouvant etre utilisee dans des applications agrochimiques
WO1999008517A1 (fr) * 1997-08-18 1999-02-25 Cognis Deutschland Gmbh Microemulsions
WO1999027781A1 (fr) * 1997-11-27 1999-06-10 Aventis Cropscience Gmbh Systemes tensioactifs pour preparations aqueuses liquides
WO2003022049A1 (fr) 2001-09-07 2003-03-20 Syngenta Participations Ag Systemes tensioactifs destines a des composes actifs sur le plan agricole
WO2003026422A1 (fr) * 2001-09-26 2003-04-03 Platte Chemical Co. Concentres formant une microemulsion herbicide, microemulsions et procedes
WO2006120554A1 (fr) * 2005-05-10 2006-11-16 Syngenta Participations Ag Compositions herbicides
US8232230B2 (en) 2000-12-01 2012-07-31 Helena Holding Company Manufacture and use of a herbicide formulation
US8426341B2 (en) 2005-05-27 2013-04-23 Helena Holding Company Herbicide formulation
US8536095B2 (en) 2008-07-03 2013-09-17 Monsanto Technology Llc Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants
EP4087397A4 (fr) * 2020-01-10 2024-01-24 Monsanto Technology Llc Compositions herbicides comprenant des agents retardateurs de dérive et leurs procédés de fabrication

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208301A (en) * 1978-07-07 1980-06-17 Diamond Shamrock Corporation Microemulsion defoamer compositions and processes for their production and use
USH224H (en) * 1985-05-30 1987-03-03 A. E. Staley Manufacturing Company Glycoside-containing agricultural treatment composition
US4853026A (en) * 1986-05-02 1989-08-01 Hoechst Aktiengesellschaft Herbicidal emulsions
US5154754A (en) * 1987-03-11 1992-10-13 Hoechst Aktiengesellschaft Oil-in-water emulsions and a process for their preparation and their use
US5227402A (en) * 1986-07-23 1993-07-13 Hoechst Aktiengesellschaft Concentrated aqueous microemulsions
US5435936A (en) * 1993-09-01 1995-07-25 Colgate Palmolive Co. Nonaqueous liquid microemulsion compositions

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208301A (en) * 1978-07-07 1980-06-17 Diamond Shamrock Corporation Microemulsion defoamer compositions and processes for their production and use
USH224H (en) * 1985-05-30 1987-03-03 A. E. Staley Manufacturing Company Glycoside-containing agricultural treatment composition
US4853026A (en) * 1986-05-02 1989-08-01 Hoechst Aktiengesellschaft Herbicidal emulsions
US5227402A (en) * 1986-07-23 1993-07-13 Hoechst Aktiengesellschaft Concentrated aqueous microemulsions
US5154754A (en) * 1987-03-11 1992-10-13 Hoechst Aktiengesellschaft Oil-in-water emulsions and a process for their preparation and their use
US5435936A (en) * 1993-09-01 1995-07-25 Colgate Palmolive Co. Nonaqueous liquid microemulsion compositions

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998028976A1 (fr) * 1996-12-30 1998-07-09 Rhodia Inc. Composition adjuvante pouvant etre utilisee dans des applications agrochimiques
WO1999008517A1 (fr) * 1997-08-18 1999-02-25 Cognis Deutschland Gmbh Microemulsions
US6255253B1 (en) 1997-08-18 2001-07-03 Cognis Deutschland Gmbh Microemulsions
AU737960B2 (en) * 1997-08-18 2001-09-06 Cognis Deutschland Gmbh & Co. Kg Microemulsions
WO1999027781A1 (fr) * 1997-11-27 1999-06-10 Aventis Cropscience Gmbh Systemes tensioactifs pour preparations aqueuses liquides
US6667276B1 (en) 1997-11-27 2003-12-23 Hoechst Schering Agrevo Gmbh Surfactant systems for liquid aqueous preparations
US8232230B2 (en) 2000-12-01 2012-07-31 Helena Holding Company Manufacture and use of a herbicide formulation
US6746988B2 (en) 2001-09-07 2004-06-08 Syngenta Crop Protection, Inc. Surfactant systems for agriculturally active compounds
WO2003022049A1 (fr) 2001-09-07 2003-03-20 Syngenta Participations Ag Systemes tensioactifs destines a des composes actifs sur le plan agricole
US6906004B2 (en) 2001-09-26 2005-06-14 Platte Chemical Co. Herbicide composition comprising herbicide compound in acid form and acidifying agent
WO2003026422A1 (fr) * 2001-09-26 2003-04-03 Platte Chemical Co. Concentres formant une microemulsion herbicide, microemulsions et procedes
US6803345B2 (en) 2001-09-26 2004-10-12 Platte Chemical Co. Herbicide microemulsion-forming-concentrates, microemulsions, and methods
WO2003026424A1 (fr) * 2001-09-26 2003-04-03 Platte Chemical Co. Compose herbicide sous forme d'acide et agent acidifiant
US7094735B2 (en) 2001-09-26 2006-08-22 Platte Chemical Co. Herbicide microemulsion-forming-concentrates, microemulsions, and methods
US6703346B2 (en) 2001-09-26 2004-03-09 Platte Chemical Co. Herbicide compositions comprising imidazolinone acid, methods of preparation, and methods of use
AU2002306811B2 (en) * 2001-09-26 2008-05-15 Platte Chemical Co. Herbicide microemulsion-forming-concentrates, microemulsions, and methods
US9237746B2 (en) 2001-09-26 2016-01-19 Platte Chemical Co. Herbicide composition comprising herbicide compound in acid form
US8759256B2 (en) 2001-09-26 2014-06-24 Platte Chemical Company Herbicide composition comprising herbicide compound in acid form and acidifying agent
US7776790B2 (en) 2001-09-26 2010-08-17 Platte Chemical Co. Herbicide compositions comprising suspension concentrate with glyphosate acid, methods of preparation, and methods of use
WO2006120554A1 (fr) * 2005-05-10 2006-11-16 Syngenta Participations Ag Compositions herbicides
CN101252835B (zh) * 2005-05-10 2012-05-30 先正达参股股份有限公司 除草组合物
EA013524B1 (ru) * 2005-05-10 2010-06-30 Зингента Партисипейшнс Аг Гербицидные композиции
EP1997376A1 (fr) * 2005-05-10 2008-12-03 Syngeta Participations AG Compositions herbicides
US8426341B2 (en) 2005-05-27 2013-04-23 Helena Holding Company Herbicide formulation
US8536095B2 (en) 2008-07-03 2013-09-17 Monsanto Technology Llc Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants
US9351486B2 (en) 2008-07-03 2016-05-31 Monsanto Technology Llc Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants
EP4087397A4 (fr) * 2020-01-10 2024-01-24 Monsanto Technology Llc Compositions herbicides comprenant des agents retardateurs de dérive et leurs procédés de fabrication

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