WO2004107862A1 - Preparations contenant des oxydes d'amine et des tensioactifs anioniques - Google Patents

Preparations contenant des oxydes d'amine et des tensioactifs anioniques Download PDF

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Publication number
WO2004107862A1
WO2004107862A1 PCT/EP2004/005847 EP2004005847W WO2004107862A1 WO 2004107862 A1 WO2004107862 A1 WO 2004107862A1 EP 2004005847 W EP2004005847 W EP 2004005847W WO 2004107862 A1 WO2004107862 A1 WO 2004107862A1
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Prior art keywords
group
carbon atoms
preparation according
alkyl
acid
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PCT/EP2004/005847
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German (de)
English (en)
Inventor
Christian Sowa
Jose Carlos Almeida Mendonca
Nelson Laercio Bonami Briotto
Marcelo Andrade Da Luz
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Clariant Gmbh
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Publication of WO2004107862A1 publication Critical patent/WO2004107862A1/fr

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    • 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
    • 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

  • the invention relates to improving the effect of the biological activity of crop protection agents or pesticides (e.g. acaricides, bactericides, fungicides, herbicides, insecticides, molluscids, nematicides and rodenticides) and phytohormones in the presence of a mixture of an amine oxide and an anionic surfactant.
  • pesticides e.g. acaricides, bactericides, fungicides, herbicides, insecticides, molluscids, nematicides and rodenticides
  • Plant protection products or pesticides are chemical or natural substances that penetrate into plant cells, tissue or parasitic organisms in or on the plant and damage or destroy them.
  • the largest proportion of pesticides are herbicides, followed by insecticides and fungicides.
  • the most important herbicides are chemical substances which act on the transport system of plants, for example by inhibiting photosynthesis, fatty acid biosynthesis or amino acid biosynthesis, and which inhibit nucleation and growth until the plant dies.
  • Phytohormones control physiological reactions such as growth, blood flow, cell division and semen maturation.
  • auxiliary substances mostly surfactants as emulsifiers, wetting agents or adhesives, are added to the preparation of the agents containing these substances.
  • No. 5,858,921 teaches that the concentration of glyphosate can be reduced without reducing the biological activity if water-soluble, long-chain alkyldimethylamine oxides and water-soluble quaternary alkylammonium halides are added to the formulation.
  • US 5,750,468 Glyphosate formulations are described which contain tertiary or quaternary ether amines as adjuvant.
  • Organosilicones show good wetting and adsorption capacity, as numerous documents show, for example WO 99/56543 and US 5,821, 195.
  • a disadvantage is the sensitivity of the silicones to hydrolysis, both in the acidic medium at pH 2 to 5 and under basic conditions.
  • the task was to develop new auxiliaries for pesticides and / or phytohormones that increase their activity, similarly to silicone surfactants, greatly reducing the surface tension of the aqueous compositions containing these substances without decomposing under acidic or alkaline conditions, and economically, simply are easy to handle and are well tolerated by humans and the environment.
  • R 1 , R 2 and R 3 each independently represent a linear or branched alkyl group having 1 to 30, preferably 1 to 22 carbon atoms, a linear or branched alkenyl group having 2 to 30, preferably 2 to 22 carbon atoms, an alkylamidopropyl group having 5 to 22 Carbon atoms in the alkyl group, a
  • the invention relates to preparations containing
  • R 1 , R 2 and R 3 each independently represent a linear or branched alkyl group having 1 to 30, preferably 1 to 22 carbon atoms, a linear or branched alkenyl group having 2 to 30, preferably 2 to 22 carbon atoms, an alkylamidopropyl group having 5 to 22 Carbon atoms in the alkyl group, an alkenylamidopropyl group with 5 to 22 carbon atoms in the
  • the preparations according to the invention bring about a reduction in the surface tension of water well below 30 mN / m at 25 ° C. and have high hydrolysis stability in the pH range from 4 to 9, even at elevated temperatures.
  • the preparations according to the invention can contain active ingredients from the group of the herbicides, insecticides, fungicides, acaricides, bactericides, molluscids, nematicides and rodenticides.
  • Herbicide formulations are preferred.
  • Suitable herbicides are, without restricting the invention thereto, acifluorfen, asulam, benazolin, bentazone, bilanafos, bromacii, bromoxynil, chloramben, clopyralid, 2,4-D, 2,4-DB, dalapon, dicamba, dichloroprop, diclofop, endothall , Fenac, Fenoxaprop, Flamprop, Fluazifop, Flumiclorac, Fluoroglycofen, Fomesafen, Fosamine, Glufosinate, Haloxyfop, Imazapic, Imazamethabenz, Imazamox, Imazapyr, Imazaquin, Imazethapyr, loxynil, MCPA, NCPalamars, Quacamamid, Quicamamop, Acid, Mopal, Acid , 2,3,6-TBA, TCA.
  • the auxiliaries according to the invention are particularly suitable for crop protection agents containing herbicides of the substance class N-phosphonomethyl-glycine (glyphosate).
  • Glyphosates are used in large quantities as very environmentally friendly and at the same time highly effective and widely used herbicides in agriculture. They are preferably used as water-soluble salts, particularly preferably as alkali metal, ammonium, alkylamine, alkylsulfonium, alkylphosphonium, sulfonylamine or Aminoguanidine salt or used as a free acid.
  • Glyphosates in the form of the mono (isopropylammonium) salt or mono (trimethylsulfonium) salt are particularly preferably used.
  • the preparations contain growth-promoting phytohormones selected from the group of auxins, preferably indoI-3-acetic acid, methyl 4-chloroindole-3-acetate, 4-chloroindolacetyl aspartate, from the group of gibberellins (diterpenes) and from the group of cytokinins, and growth-inhibiting phytohormones, preferably abscisic acid, xanthaxins, jasmonic acid, jasmonates and ethylene-releasing substances such as L-methionine.
  • auxins preferably indoI-3-acetic acid, methyl 4-chloroindole-3-acetate, 4-chloroindolacetyl aspartate
  • gibberellins diterpenes
  • cytokinins cytokinins
  • growth-inhibiting phytohormones preferably abscisic acid, xanthaxins, jasmonic acid, jasmonates and ethylene-
  • Preferred compounds of the formula I are those in which R 1 , R 2 and R 3 each independently of one another denote a linear or branched alkyl group having 1 to 30, preferably 1 to 22, carbon atoms.
  • R 1 and R 2 are methyl groups and R 3 is an alkyl group having 5 to 22 and preferably 8 to 18 carbon atoms. Particularly preferred among these compounds are those in which R 3 denotes an alkyl group with 10 carbon atoms,
  • R 3 is an alkyl group having 12 to 16 carbon atoms, such as lauryldimethylamine oxide, and
  • a compound of the formula I is mixed with one or more anionic surfactants.
  • the mixture of amine oxide and anionic surfactant is very water-soluble, well compatible with other components and, in a synergistic manner, brings about a strong reduction in the surface tension.
  • Preferred anionic surfactants are straight-chain and branched alkyl sulfates, sulfonates, carboxylates, phosphates, sulfosuccinates and taurates, alkyl ester sulfonates, arylalkyl sulfonates and alkyl ether sulfates.
  • Alkyl sulfates are water-soluble salts or acids of the formula ROSO 3 M, in which R is preferably a C 1 -C 24 -hydrocarbon radical, particularly preferably an alkyl or hydroxyalkyl radical having 10 to 20 C atoms and particularly preferably a C 1 -C 8 -alkyl or Represents hydroxyalkyl.
  • M is hydrogen or a cation, preferably an alkali metal cation (e.g. sodium, potassium, lithium) or ammonium or substituted ammonium, e.g. a methyl, dimethyl and trimethylammonium cation or a quaternary ammonium cation such as tetramethylammonium and dimethylpiperidinium cation and quaternary ammonium cations derived from alkylamines such as ethylamine, diethylamine, triethylamine and mixtures thereof.
  • alkali metal cation e.g. sodium, potassium, lithium
  • ammonium or substituted ammonium e.g. a methyl, dimethyl and trimethylammonium cation or a quaternary ammonium cation such as tetramethylammonium and dimethylpiperidinium cation and quaternary ammonium cations derived from alkylamines such as ethylamine, die
  • the alkyl ether sulfates are water soluble salts or acids of the formula RO (A) m SO 3 M wherein R preferably is an unsubstituted C ⁇ o-C 2 4 alkyl or hydroxyalkyl group, particularly preferably a C ⁇ 2 -C 2 o alkyl or hydroxyalkyl group, and particularly preferably represents a Ci 2 -C ⁇ s alkyl or hydroxyalkyl radical.
  • A is an ethoxy or propoxy unit
  • m is a number greater than 0, typically between approximately 0.5 and approximately 6, particularly preferably between approximately 0.5 and approximately 3
  • M is a hydrogen atom or a cation, preferably a metal cation (e.g.
  • substituted ammonium cations are methyl, dimethyl, trimethylammonium and quaternary ammonium cations such as tetramethylammonium and
  • Dimethylpiperidinium cations as well as those derived from alkylamines such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • alkylamines such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • alkylamines such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • alkylamines such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • alkylamines such as ethylamine, diethylamine, triethylamine or mixtures thereof.
  • C 2 -C-i8-alkyl polyethoxylate 1, 0) sulfate
  • C ⁇ 2 -C ⁇ 8 alkyl polyethoxylate 3 , 0
  • alkyl sulfonates with straight-chain or branched C 6 -C 22 -alkyl chains for example primary paraffin sulfonates, secondary paraffin sulfonates, alkylarylsulfonates, for example linear alkylbenzenesulfonates with C5-C20-alkyl chains, alkylnaphthalenesulfonates, condensation products from naphthalenesulfonates and formaldehyde sulfonates, formaldehyde sulfonates, laldehyde sulfonates, formaldehyde sulfonates, formaldehyde sulfonates, and formaldehyde sulfates sulfonated linear esters of sulfonated polycarboxylic acids produced by sulfonating the pyrolysis products of alkaline earth metal citrates.
  • Suitable anionic surfactants are selected from alkylglycerol, Fettacylglycerinsulfaten, Oleylglycerinsulfaten, alkylphenol ether sulfates, alkyl phosphates, alkyl ether phosphates, isethionates, such as acylisethionates, N-acyl taurides, Alkylsuccinamaten, sulfosuccinates, Monoestern of sulfosuccinates (especially saturated and unsaturated C 2 -C 8 monoesters) and diesters of Sulfosuccinates (especially saturated and unsaturated C 12 -C 18 diesters), acyl sarcosinates, sulfates of alkyl polysaccharides such as sulfates of alkyl polyglycosides, branched primary alkyl sulfates and alkyl polyethoxy carboxylates such as those of the formula RO (CH 2 CH 2
  • the weight ratio of the one or more compounds of the formula I to the one or more anionic surfactants is from 95: 5 to 5:95, preferably from 80:20 to 20:80, particularly preferably from 80:20 to 70: 30 or from 20: 80 to 30: 70.
  • the preparations according to the invention contain one or more nonionic surfactants, amphoteric surfactants and / or cationic surfactants as a further component.
  • preparations according to the invention which contain one or more nonionic surfactants and / or one or more amphoteric surfactants as a further component.
  • Suitable nonionic surfactants are preferably fatty alcohol ethoxylates (alkyl polyethylene glycols), alkylphenol polyethylene glycols, alkyl mercaptan polyethylene glycols, fatty amine ethoxylates
  • Alkylaminopolyethylene glycols fatty acid ethoxylates
  • fatty acid ethoxylates acylpolyethylene glycols
  • polypropylene glycol ethoxylates eg Pluronics ®
  • fatty acid alkylolamides fatty acid amide polyethylene glycols
  • N-alkyl and N-alkoxy polyhydroxy fatty acid amides alkyl polysaccharides, sucrose esters, sorbitol esters and polyglycol ethers.
  • amphoteric surfactants are amphoacetates, particularly preferably monocarboxylates and dicarboxylates such as cocoamphocarboxypropionate, cocoamidocarboxypropionic acid, cocoamphocarboxyglycinate (or also referred to as cocoamphodiacetate) and cocoamphoacetate.
  • Cationic surfactants which can be used are di- (C 1 -C 24 ) -alkyldimethylammonium chloride or bromide, preferably di- (Ci2-Ci ⁇ ) -alkyldimethylammonium chloride or bromide; (C ⁇ o-C 24 ) alkyl dimethyl ethyl ammonium chloride or bromide; (C ⁇ o-C 24 ) alkyl trimethyl ammonium chloride or bromide, preferably cetyl trimethyl ammonium chloride or bromide and (C 2 oC 22 ) alkyl trimethyl ammonium chloride or bromide; (-C 0 -C 24 ) alkyl dimethylbenzyl ammonium chloride or bromide, preferably (Ci 2 -C 8 ) alkyl dimethylbenzyl ammonium chloride; N- (-C ⁇ -C ⁇ 8 ) alkyl pyridinium chloride or bromide, preferably N- (Ci2-
  • surfactant mixtures of compound of formula I and anionic surfactant, optionally mixed with nonionic, cationic and / or amphoteric surfactants are suitable as adjuvants in crop protection formulations, both in solid form and in gel or paste form, preferably in sprayable liquid form.
  • the formulations according to the invention can be prepared in solid form as powders, pellets, tablets or granules, which are dissolved in water before use.
  • Solid preparations can the pesticide and / or phytohormone in the amounts of 20 to 80, preferably from 50 to 75, particularly preferably from 60 to 70 wt .-% and surfactant mixtures of the compound of formula I and anionic surfactant, optionally mixed with nonionic and / or amphoteric surfactant in the amounts 5 to 50, preferably 10 to 30 wt .-%.
  • Concentrate formulations which are diluted before use can contain the pesticide and / or phytohormone in the amounts 5 to 50, preferably 20 to 40% by weight and the surfactant mixture in the amounts 5 to 70% by weight.
  • the formulations according to the invention can contain thickeners, anti-gel agents, freezing agents, solvents, dispersants, emulsifiers, preservatives, further adjuvants, binders, anti-foaming agents, thinners, disintegrants and wetting agents.
  • Xanthan gum and / or cellulose for example carboxy, methyl, ethyl or propyl cellulose, can be used as a thickening agent in the amounts by weight of 0.01 to 5%, based on the finished agent.
  • Water, ethylene glycol, diethylene glycol and monopropylene glycol are suitable as solvents.
  • Non-ionic, amphoteric, cationic and anionic surfactants are suitable as dispersants and emulsifiers.
  • Organic acids and their esters for example ascorbic acid, ascorbic palmitate, sorbate, benzoic acid, methyl and propyl 4-hydroxybenzoate, propionates, phenol, for example 2-phenylphenate, 1, 2-benzisothiazoiin-3-one, formaldehyde, sulfuric acid can be used as preservatives and their salts are used.
  • Polysilicones are suitable as defoamers.
  • adjuvants can be polyglycerol esters, alcohol ethoxylates, alkyl polysaccharides, fatty amine ethoxylates, sorbitan and sorbitol ethoxylate derivatives and derivatives of alk (en) yl succinic anhydride.
  • polyvinylpyrrolidone, polyvinyl alcohol, carboxymethyl cellulose, sugar, for example sucrose, sorbitol or starch are suitable as binders.
  • Carbon black, tallow, kaolin, aluminum, calcium or magnesium stearate, sodium tripolyphosphate, sodium tetraborate, sodium sulphate, silicates and sodium benzoate are suitable as thinners, absorbers or carriers.
  • Cellulose for example carboxymethyl cellulose, polyvinylpyrrolidone, sodium or potassium acetate, carbonates, bicarbonates, sesquicarbonates, ammonium sulfate or potassium hydrogen phosphate act as disintegrants.
  • Alcohol ethoxylates / propoxylates can be used as wetting agents.
  • a great advantage in terms of application technology is the high pH stability of the preparations according to the invention with surfactant mixtures of compounds of the formula I and anionic surfactant.
  • formulations according to the invention can be applied by the customary methods.
  • Aqueous concentrates and solid formulations are diluted with the appropriate amount of water before application.
  • the proportion of the adjuvant according to the invention is in the range from 0.15 to 2.1 kg / ha.
  • the volume of the formulation created for spraying is in the range from 50 to 1000 l / ha.
  • the content of compounds of the formula I in the preparations according to the invention can vary within wide limits.
  • the following formulations are preferred.
  • Formulations as "tank mix” and “ready to use compositions” contain 0.001 to 10% by weight, preferably 0.05 to 2% by weight of pesticide and / or phytohormone and 0.01 to 10% by weight, preferably 0.1 to 2 wt .-%, particularly preferably 0.2 to 1 wt .-% of the compounds of formula I.
  • the ratio of adjuvant to pesticide and / or phytohormone can be between 1:10 to 500: 1, in particular 1: 4 to 4: 1.
  • the preparations according to the invention contain water.
  • the invention therefore also relates to
  • compositions containing a preparation according to the invention and water are provided.
  • Another object of the invention is the use of a preparation according to the invention or a composition containing a preparation according to the invention and water for controlling weeds.
  • the invention furthermore also relates to the use of a preparation according to the invention or a composition comprising a preparation according to the invention and water for regulating the growth of plants.
  • Genaminox LA Genaminox LA lauryldimethylamine oxide 20% by weight
  • Genapol LRO fl alkyldiglycol ether sulfate, Na salt 20% by weight
  • Genapol LRO / Genaminox LA is more stable over a wide pH and temperature range compared to the silicone surfactant available under the trade name Silwet L-77.
  • Example 2 The static surface tension of Genapol LRO fl, Genaminox LA and a mixture of 80% Genapol LRO fl and 20% Genaminox LA was measured as a function of the concentration in water at a temperature of 25 ° C.
  • the surfactant mixtures indicated represent surfactant mixtures to be used in the preparations according to the invention.
  • the measured values are shown in Table 2. It was found that the surfactant mixtures have a synergistic effect in reducing the surface tension compared to the individual components.
  • Table 2 Static surface tension of the individual substances Genaminox LA and Genapol LRO and a surfactant mixture depending on the concentration at a temperature of 25 ° C
  • Measuring temperature 25 ° C method: combination of two methods: platinum ring method with automatic dilution, platinum plate
  • the static surface tension of a mixture of 80% Genapol LRO fl and 20% Genaminox LA was determined depending on the concentration for different water hardness levels.
  • the surfactant mixture used represents a surfactant mixture to be used in the preparations according to the invention. The measured values are shown in Table 3.

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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

Préparations qui contiennent (A) un ou plusieurs pesticides et / ou une ou plusieurs phytohormones, (B) un ou plusieurs oxydes d'amine et (C) un ou plusieurs tensioactifs anioniques.
PCT/EP2004/005847 2003-06-04 2004-05-29 Preparations contenant des oxydes d'amine et des tensioactifs anioniques WO2004107862A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10325199.5 2003-06-04
DE2003125199 DE10325199A1 (de) 2003-06-04 2003-06-04 Zubereitungen enthaltend Aminoxide und anionische Tenside

Publications (1)

Publication Number Publication Date
WO2004107862A1 true WO2004107862A1 (fr) 2004-12-16

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005089232A2 (fr) 2004-03-12 2005-09-29 Fmc Corporation Composition de glyphosate
WO2007054540A2 (fr) * 2005-11-10 2007-05-18 Rhodia Operations Composition herbicide comprenant des sels de potassium d’aminophosphate ou d’aminophosphonate
WO2013083537A1 (fr) * 2011-12-07 2013-06-13 Akzo Nobel Chemicals International B.V. Alkylsulfonates à courte chaîne dans des formulations de pesticides et applications
US8633136B2 (en) 2006-10-16 2014-01-21 Rhodia Operations Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions
US8637622B2 (en) 2007-04-05 2014-01-28 Rhodia Operations Copolymer including betaine units and hydrophobic and/or amphiphilic units, method for preparing same and uses thereof
US8841235B2 (en) 2010-08-10 2014-09-23 Rhodia Operations Agricultural pesticide compositions
WO2014199293A1 (fr) * 2013-06-12 2014-12-18 Upl Limited Formulations agrochimiques
US9045720B2 (en) 2004-12-30 2015-06-02 Rhodia Chimie Herbicidal composition comprising an aminophosphate or aminophosphonate salt, a betaine and an amine oxide
US9107405B2 (en) 2005-11-14 2015-08-18 Rhodia Operations Agricultural adjuvant compostions, pesticide compositions, and methods for using such compositions
US20170049099A1 (en) * 2008-08-19 2017-02-23 Akzo Nobel N.V. Thickening glyphosate formulations
EP3334278A4 (fr) * 2015-08-11 2019-01-16 Rhodia Operations Compositions herbicides à charge élevée stables comprenant des oxydes d'amines mélangés
US10993442B2 (en) 2008-06-18 2021-05-04 Stepan Company Ultra-high loading glyphosate concentrate

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GB2049427A (en) * 1979-03-28 1980-12-31 Monsanto Co Emulsifiable concentrate formulations compatible with water and liquid fertilizers
WO2001005225A1 (fr) * 1999-07-19 2001-01-25 Monsanto Technology Llc Compositions aqueuses concentrees de pesticide moins nocives pour les yeux et la peau
WO2001008482A1 (fr) * 1999-07-31 2001-02-08 Rhodia Consumer Specialties Limited Compositions herbicides
WO2002021916A2 (fr) * 2000-09-14 2002-03-21 Stepan Company Melange de tensio-actifs ternaires antimicrobiens comprenant des tensio-actifs cationiques, anioniques et de pontage, et procedes de preparation
WO2002026036A1 (fr) * 2000-09-29 2002-04-04 Syngenta Limited Composition agrochimique contenant des adjuvants a activite amplificatrice

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
GB2049427A (en) * 1979-03-28 1980-12-31 Monsanto Co Emulsifiable concentrate formulations compatible with water and liquid fertilizers
WO2001005225A1 (fr) * 1999-07-19 2001-01-25 Monsanto Technology Llc Compositions aqueuses concentrees de pesticide moins nocives pour les yeux et la peau
WO2001008482A1 (fr) * 1999-07-31 2001-02-08 Rhodia Consumer Specialties Limited Compositions herbicides
WO2002021916A2 (fr) * 2000-09-14 2002-03-21 Stepan Company Melange de tensio-actifs ternaires antimicrobiens comprenant des tensio-actifs cationiques, anioniques et de pontage, et procedes de preparation
WO2002026036A1 (fr) * 2000-09-29 2002-04-04 Syngenta Limited Composition agrochimique contenant des adjuvants a activite amplificatrice

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1722628A2 (fr) * 2004-03-12 2006-11-22 Fmc Corporation Composition de glyphosate
EP1722628A4 (fr) * 2004-03-12 2009-04-22 Fmc Corp Composition de glyphosate
AU2005222910B2 (en) * 2004-03-12 2010-06-10 Fmc Corporation Glyphosate composition
WO2005089232A2 (fr) 2004-03-12 2005-09-29 Fmc Corporation Composition de glyphosate
US9045720B2 (en) 2004-12-30 2015-06-02 Rhodia Chimie Herbicidal composition comprising an aminophosphate or aminophosphonate salt, a betaine and an amine oxide
WO2007054540A2 (fr) * 2005-11-10 2007-05-18 Rhodia Operations Composition herbicide comprenant des sels de potassium d’aminophosphate ou d’aminophosphonate
WO2007054540A3 (fr) * 2005-11-10 2007-09-13 Rhodia Recherches & Tech Composition herbicide comprenant des sels de potassium d’aminophosphate ou d’aminophosphonate
AU2006311022B2 (en) * 2005-11-10 2011-05-12 Specialty Operations France Herbicidal composition comprising aminophosphate or aminophosphonate potassium salt
AU2011200512B2 (en) * 2005-11-10 2012-12-06 Specialty Operations France Herbicidal composition comprising aminophosphate or aminophosphonate potassium salt
US9107405B2 (en) 2005-11-14 2015-08-18 Rhodia Operations Agricultural adjuvant compostions, pesticide compositions, and methods for using such compositions
US8633136B2 (en) 2006-10-16 2014-01-21 Rhodia Operations Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions
US8637622B2 (en) 2007-04-05 2014-01-28 Rhodia Operations Copolymer including betaine units and hydrophobic and/or amphiphilic units, method for preparing same and uses thereof
US10993442B2 (en) 2008-06-18 2021-05-04 Stepan Company Ultra-high loading glyphosate concentrate
US20170049099A1 (en) * 2008-08-19 2017-02-23 Akzo Nobel N.V. Thickening glyphosate formulations
US8841235B2 (en) 2010-08-10 2014-09-23 Rhodia Operations Agricultural pesticide compositions
CN104023530A (zh) * 2011-12-07 2014-09-03 阿克佐诺贝尔化学国际公司 农药配制剂中的短链烃基磺酸盐及施用
WO2013083537A1 (fr) * 2011-12-07 2013-06-13 Akzo Nobel Chemicals International B.V. Alkylsulfonates à courte chaîne dans des formulations de pesticides et applications
AU2012347377B2 (en) * 2011-12-07 2015-10-22 Akzo Nobel Chemicals International B.V. Short-chain alkyl sulfonates in pesticide formulations and applications
CN104023530B (zh) * 2011-12-07 2016-08-17 阿克佐诺贝尔化学国际公司 农药配制剂中的短链烃基磺酸盐及施用
WO2014199293A1 (fr) * 2013-06-12 2014-12-18 Upl Limited Formulations agrochimiques
US10506806B2 (en) 2013-06-12 2019-12-17 Upl Limited Agrochemical formulations
EP3334278A4 (fr) * 2015-08-11 2019-01-16 Rhodia Operations Compositions herbicides à charge élevée stables comprenant des oxydes d'amines mélangés
US11357228B2 (en) 2015-08-11 2022-06-14 Rhodia Operations Stable high-load herbicidal compositions comprising mixed amine oxides

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BRPI0401912A (pt) 2005-03-22

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