Surfactant Systems for Agriculturally Active

(19) &

(11) EP 1 423 001 B1

(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 25/30 (2006.01) A01N 57/20 (2006.01) 09.11.2011 Bulletin 2011/45 A01N 43/70 (2006.01)

(21) Application number: 02757590.1 (86) International application number: PCT/US2002/028207 (22) Date of filing: 05.09.2002 (87) International publication number: WO 2003/022049 (20.03.2003 Gazette 2003/12)

(54) SURFACTANT SYSTEMS FOR AGRICULTURALLY ACTIVE COMPOUNDS OBERFLÄCHENAKTIVE SYSTEME FÜR LANDWIRTSCHAFTLICH AKTIVE VERBINDUNGEN SYSTEMES TENSIOACTIFS DESTINES A DES COMPOSES ACTIFS SUR LE PLAN AGRICOLE

(84) Designated Contracting States: • FOWLER, Jeffrey, D. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Syngenta Crop Protection, Inc. IE IT LI LU MC NL PT SE SK TR Greensboro, NC 27409 (US)

(30) Priority: 07.09.2001 US 317474 P (74) Representative: Arunasalam, Velautha-Cumaran Syngenta Participations AG (43) Date of publication of application: Intellectual Property 02.06.2004 Bulletin 2004/23 P.O. Box 4058 Basel (CH) (73) Proprietor: Syngenta Participations AG 4058 Basel (CH) (56) References cited: EP-A- 0 511 611 WO-A-00/35284 (72) Inventors: WO-A-00/35863 WO-A-96/08150 • HOPKINSON, Michael J. US-A- 5 877 112 US-A- 5 885 931 Syngenta Crop Protection Inc Greensboro, NC 27409 (US) Remarks: • MOORE, Carolyn, E. Thefile contains technical information submitted after Syngenta Crop Protection, Inc. the application was filed and not included in this Greensboro, NC 27409 (US) specification

Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 423 001 B1

Printed by Jouve, 75001 PARIS (FR) 1 EP 1 423 001 B1 2

Description atrazine; S-metolachlor, atrazine and benoxacor; S-metolachlor, atrazine and butavenacil; S-metolachlor, atra- [0001] The invention provides herbicidal compositions zine, benoxacor and butafenacil; glyphosate, acetochlor that contain a surfactant system and one or more herbi- and atrazine; glyphosate, S-metolachlor and atrazine; cidally active compounds and a fertilizer. The composi- 5 glufosinate, acetochlor and atrazine; glufosinate, S-me- tions also comprise alkyl polyglycosides, anionic sur- tolachlor and atrazine; mesotrione and S-metolachlor; factants, basic compounds, and/or nonionic surfactants. mesotrione, S-metolachlor and benoxacor; mesotrione, The herbicidal compositions exhibit excellent chemical S-metolachlor and atrazine; or mesotrione, S-metol- and physical stability as well as tank-mix compatibility achlor, benoxacor and atrazine. ; properties that are highly desirable for commercial prod- 10 at least one alkyl polyglycoside; ucts in the agricultural chemicals industry. at least one fertilizer, which comprises nitrogen, phos- [0002] The challenge involved in developing commer- phorous and/or potassium; cially acceptable products containing herbicidally active at least one anionic surfactant selected from a polyaryl- compounds continues to increase due to the rapid emer- phenol polyalkoxyether sulfate and a polyarylphenol gence of more complex customer and regulatory require- 15 polyalkoxyether phosphate; and ments. The formulation of products containing multiple at least one basic compound; active ingredients with very different physical properties wherein the alkyl polyglycoside is a compound of formula is increasingly required in the marketplace to provide a (II): broader spectrum of biological activity in a single product offering. These compositions must exhibit excellent20 chemical stability and must also maintain a high level of physical stability under a severe range of storage and use conditions. Handling of a liquid product in bulk storage facilities represents a special challenge because the product can be subject to high shear forces at both high 25 and low temperatures. The complexity of the application medium into which the compositions will be blended is also rapidly increasing, creating significant new require- ments for compatibility in the application process. This emerging area of performance is critical to customer sat- 30 isfaction and commercial success with a product since poor compatibility in the final use mixture can cause blockage of sprayer screens and nozzles, preventing proper application of the product At the same time that the demand on the herbicidal composition performance 35 has been increasing, the number of auxiliary chemicals where n is the degree of polymerization and is from 1 to approved for use in herbicidal compositions by the U.S. 3, preferably 1 or 2, and R 5 is a branched or straight chain EPA has been decreasing due to more stringent stand- alkyl group having from 4 to 18 carbon atoms or a mixture ards for the toxicological and ecological properties of of alkyl groups having from 4 to 18 carbon atoms; and these materials. 40 wherein the at least one anionic surfactant is neutralized [0003] WO 00/35863 describes a surfactant system for to the inflection point in the titration curve with the at least use in agrochemical compositions comprising an alkox- one basic compound. ylated tristyrylphenol acid neutralized with alkoxylated [0006] The invention provides flowable concentrates alkyl amine. The compositions may contain further con- comprising water; at least one active compound as de- ventional formulation aids such as antifoaming biostatic 45 fined above; at least one alkyl polyglycoside of formula and thickening agents. (II); at least one fertilizer, which comprises nitrogen, [0004] WO 96/08150 relates to microemulsions con- phosphorous and/or potassium; at least one anionic sur- taining a surfactant mixture which comprises an ethoxy- factantselected from polyarylphenol polyalkoxyether sul- lated acid, an alkyl polyglycoside, ethoxylated castor oil, fates and polyarylphenol polyalkoxyether phosphates; at optionally ethoxylated alkyl phenyl phosphate and a co- 50 least one basic compound; and, optionally, at least one surfactant. nonionic surfactant. The at least one anionic surfactant [0005] The inventionprovides aherbicidal composition is neutralized to the inflection point in the titration curve comprising with the at least one basic compound. The flowable con- at least one herbicidally active compound selected from centrates may be, for example, suspoemulsions, aque- glyphosate; S-metolachlor; atrazine,; glufosinate; aceto- 55 ous suspension concentrates, aqueous emulsion con- chlor; mesotrione; glyphosate andmetolachlor; S- centrates, or oilmiscible flowable concentrates. glyphosate, S-metolachlor and atrazine,; glyphosate, S- [0007] The invention provides water-in-oil emulsions, metolachlor, atrazine and benoxacor; S-metolachlor and capsule emulsions and polymer-stabilized aqueous

2 3 EP 1 423 001 B1 4 emulsions comprising water; at least one active com- by weight, preferably in an amount of 0.5 to 4% by weight. pound as defined above; at least one alkyl polyglycoside [0013] The anionic surfactants used in the invention of formula (II); at least one fertilizer, which comprises may be any known in the art. The anionic surfactants are nitrogen, phosphorous and/or potassium; at least one selected from polyarylphenol polyalkoxyether sulfate anionic surfactant selected from polyarylphenol poly- 5 and/or at least one polyarylphenol polyalkoxyether phos- alkoxyether sulfates and polyarylphenol polyalkoxyether phate. phosphates; at least one basic compound,; and, option- [0014] Exemplary polyaryl phenol polyalkoxyether sul- ally, at least one nonionic surfactant. The at least one fates and phosphates include polyarylphenol polyethox- anionic surfactant is neutralized to the inflection point in yether sulfates and phosphates, and salts thereof. The the titration curve with the at least one basic compound. 10 term "aryl" includes, for example, phenyl, tolyl, naphthyl, [0008] The herbicidal compositions, flowable concen- tetrahydronaphthyl, indanyl, indenyl, styryl, and mixtures trates, water-in-oil emulsions, capsule emulsions, and thereof. Exemplary polyarylphenol polyethoxyether sul- polymer-stabilized aqueous emulsions of the invention fates and phosphates include tristyrylphenol polyethox- may further comprise other additives, such as thickeners, yether sulfates and phosphates. The polyarylphenol flow enhancers, wetting agents, antifoaming agents,15 polyalkoxether sulfates and phosphates may have a de- buffers, lubricants, fillers, drift control agents, deposition gree of alkoxylation (e.g., ethoxylation) of between about enhancers, adjuvants, evaporation retardants, frost pro- 1 and about 50, preferably between about 2 and about tecting agents, insect attracting odor agents, fragrances, 40, more preferably between about 5 and about 30. Com- and the like. mercially available polyarylphenol polyalkoxyether sul- [0009] It has been unexpectedly discovered that the 20 fates and phosphates include, for example, SOPRO- compositions of the invention, which contain fertilizers, PHOR® 4 D 384 (Rhodia Corporation, Cranbury, NJ) do not exhibit any visible flocculation after about one (tristyrylphenol (EO)16 sulfate ammonium salt), SOPRO- hour. The fertilizers comprise nitrogen, phosphorous PHOR® 3 D 33 (Rhodia Corporation, Cranbury, NJ) (tris- and/or potassium. In one embodiment, the fertilizer may tyrylphenol (EO)16 phosphate free acid), SOPRO- be 10-34-0 fertilizer. 25 PHOR® FLK (Rhodia Corporation, Cranbury, NJ) (tris- [0010] Exemplary alkyl polyglycosides include APG® tyrylphenol (EO)16 phosphate potassium salt), DEH- 325 (Cognis Corporation, Cincinnati, OH) (an alkyl poly- SCOFIX® 904 (Albright & Wilson Americas, Inc., Glen glycoside in which the alkyl group contains 9 to 11 carbon Allen, VA) (tristyrylphenol polyethoxylated ether phos- atoms and has an average degree of polymerization of phate triethanolamine salt), HOE® S 3475 (Hoechst) 1.6), PLANTAREN® 2000 (Cognis Corporation, Cincin- 30 (tristyrylphenol polyethoxylated ether phosphate trieth- niiti, OH) (an alkyl polyglycoside in which the alkyl group anolamine salt), and SOPROPHOR® RAM/384 (tristy- contains 8 to 16 carbon atoms and has an average de- rylphenol polyethoxylated ether sulfate neutralized with gree of polymerization of 1.4), PLANTARN® 1300 (Cog- polyethoxylated oleylamine). In other embodiments, the nis Corporation, Cincinnuti, OH) (an alkyl polyglycoside polyarylphenol polyalkoxyether sulfates and phosphates in which the alkyl group contains 12 to 16 carbon atom.s 35 may be mono-arylphenol polyalkoxyether sulfates and and has an average degree of polymerization of 1.6), phosphates, such as styrylphenol polyethoxyether sul- AGRIMUL® PG 2067 (Cognis Corporation, Cincinnati, fates and phosphates. OH) (an alkyl polyglycoside in which the alkyl group con- [0015] Other anionic surfactants may also be included tains 8 to 10 carbon atoms and has an average degree in the herbicidal compositions of the invention. Such an- 40 ofpolymerization of 1.7), AGRZMCTL® PG 2069 (Cognis ionic surfactants include, for example, C 8-20 alkyl carbox- Corporation, Cincinnati, OH) (an alkyl polyglycoside in ylates including fatty acids, C8-20 alcohol sulfates, C8-20 which the alkyl group contains 9 to 11 carbon atoms and alcohol phosphate mono- and diesters, C 8-20 alcohol and has an average degree of polymerization of 1.6), (C8-20 alkyl)phenol polyoxyethylene ether carboxylates, AGRIMUL® PG 2076 (Cognis Corporation, Cincinnati, sulfates and sulfonates, C8-20 alcohol and (C8-20 alkyl) OH) (an alkyl polyglycoside in which the alkyl group con- 45 phenol polyoxyethylene phosphate mono- and diesters, tains 8 to 10 carbon atoms and has an average degree C8-20 alkylbenzene sulfonates, naphthalene sulfonates of polymerization of 1.5), ATPLUS® 438 (Uniqema, Inc., and formaldehyde condensates thereof, lignosulfonates, Wilmington, DE) (an alkylpolysaccharide in which the G8-20 alkyl sulfosuccinates and sulfosuccinamates, and alkyl group contains 9 to 11 carbon atoms), and AT- C8-2o acyl glutamates, sarcosinates, isethionates and PLUS® 452 (Uniqema, Inc., Wilmington, DE) (an alkyl- 50 taurates. Of these anionic surfactants, it is preferable to polysaccharide in which the alkyl group contains 8 to 10 use C8-2o alkyl carboxylates including fatty acids, C8-20 carbon atoms). alcohol sulfates, C8-20 alcohol phosphate mono- and di- [0011] In preferred embodiments, the alkyl polyglyco- esters, C8-20 alcohol polyoxyethylene ether carboxy- side is a (C8-10 alkyl)-O(glucose)2 (e.g., AGRIMUL® PG lates, sulfates and sulfonates, C 8-20 alcohol polyoxyeth- 55 2067); a (C9-11 alkyl)-O(glucose)2 (e.g., AGRIMUL® PG ylene phosphate mono- and diesters, C 8-20 alkylbenzene 2069); or a mixture thereof. sulfonates, naphthalene sulfonates and formaldehyde [0012] The alkyl polyglycosides may be used in the condensates thereof, lignosulfonates, C8-20 alkyl sulfo- compositions of the invention in an amount of 0.1 to 8% succinates and sulfosuccinamates, and C 8-20 acyl gluta-

3 5 EP 1 423 001 B1 6 mates, sarcosinates, isethionates and taurates. anionic surfactants neutralized to the inflection point in [0016] In one embodiment, the compositions of the in- the titration curve with one or more basic compounds. vention may comprise at least one anionic surfactant. In The basic compound used to neutralize the different an- another embodiment, the compositions of the invention ionic surfactants may be the same or different. Such one may comprise at least two anionic surfactants. In another 5 or more additional anionic surfactants may include, for embodiment, the compositions of the invention may com- example, C8-20 alkyl carboxylates including fatty acids, prise at least three anionic surfactants. In another em- C8-20 alcohol sulfates, C8-20 alcohol phosphate mono- bodiment, the compositions of the invention may com- and diesters, C8-20 alcohol and (C8-20 alkyl)phenol poly- prise at least four anionic surfactants. The anionic sur- oxyethylene ether carboxylates, sulfates and sulfonates, 10 factants may be used in the compositions in an amount C8-20 alcohol and (C8-20 alkyl)phenol polyoxyethylene of 0.1 to 8% by weight, preferably in an amount of 1 to phosphate mono- and diesters, C8-20 alkylbenzene sul- 4% by weight. fonates, naphthalene sulfonates and formaldehyde con- [0017] The basic compounds may be any known in the densates thereof, lignosulfonates, C 8-20 alkyl sulfbsucci- art that are capable of neutralizing the anionic sur- nates and sulfosuccinamates, and C 8-20 acyl glutamates, factants. Basic compounds include, for example, inor- 15 sarcosinates, isethionates and taurates. Of these one or ganic bases, C8-18 alkyl amine polyalkoxylates, alkanol more additional anionic surfactants, it is preferable to use amines, alkanol amides, and mixtures thereof. C8-20 alkyl carboxylates including fatty acids, C 8-20 alco- [0018] Exemplary inorganic bases include ammonium hol sulfates, C 8-20 alcohol phosphate mono- and diesters, hydroxides, sodium hydroxides, potassium hydroxides, C8-20 alcohol polyoxyethylene ether carboxylates, sul- 20 calcium hydroxides, magnesium hydroxides, zinc hy- fates and sulfonates, 8-20 C alcohol polyoxyethylene droxides, and mixtures thereof. The C8-18 alkyl amine phosphate mono- and diesters, C8-20 alkylbenzene sul- polyalkoxylates may be, for example, C8-18 alkyl amine fonates, naphthalene sulfonates and formaldehyde con- polypropoxylates and/or C8-18 alkyl amine polyethoxy- densates thereof, lignosulfonates, C 8-20 alkyl sulfosucci- lates. Exemplary C8-18 alkyl amine polyalkoxylates in- nates and sulfosuccinamates, and C 8-20 acyl glutamates, clude tallow amine polyalkoxylates, cocoamine poly-25 sarcosinates, isethionates and taurates. alkoxylates, oleylamine polyalkoxylates, and stear- [0022] The anionic surfactants and basic compounds ylamine polyalkoxylates. The C8-18 alkyl amine poly- are preferably used in a ratio of about 1.1: One basic ethoxyates may have from 2 to 50 moles of ethylene ox- compound may be used to neutralize one or more anionic ide per molecule, more preferably from 2 to 20 moles of surfactants. In other embodiments, more than one basic 30 ethylene oxide per molecule. Exemplary 8-18 C alkyl compound may be used to neutralize one or more anionic amine polyethoxylates include tallow amine ethoxylates surfactants. (2 moles EO or 8 moles EO), cocoamine ethoxylates, [0023] The compositions of the invention may option- oleylamine ethoxylates, and stearylamine ethoxylates. ally further comprise one or more nonionic surfactants. Exemplary alkanol amines include diethanol amine and The "nonionic surfactants" are different compounds from triethanol amine. Exemplary alkanol amides include oleic 35 the alkyl polyglycosides described herein. Exemplary no- diethanolamide and linoleic diethanolamide, and the di- nionic surfactants include ethylene oxide-propylene ox- ethanolamides of other C8-18 fatty acids. ide block copolymers, ethylene oxide-butylene oxide [0019] The basic compounds may be used in an block copolymers, C2-6 alkyl adducts of ethylene oxide- amount of 0.1 to 8% by weight, preferably in an amount propylene oxide block copolymers, C 2-6 alkyl adducts of of 0.5 to 4% by weight. 40 ethylene oxide-butylene oxide block copolymers, poly- [0020] The one or more anionic surfactants are pref- propylene glycols, polyethylene glycols, polyarylphenol erably neutralized to the inflection point in the titration polyethoxy ethers, polyalkylphenol polyethoxy ethers, curve with the one or more basic compounds. One skilled polyglycol ether derivatives of saturated fatty acids, pol- in the art will recognize that the pH of the inflection will yglycol ether derivatives of unsaturated fatty acids, pol- vary according to the acid and base strengths of the com- 45 yglycol ether derivatives of aliphatic alcohols, polyglycol ponents being used, but will generally fall within the range ether derivatives of cycloaliphatic alcohols, fatty acid es- of about pH 4 to about pH 9, preferably about pH 5 to ters of polyoxyethylene sorbitan, alkoxylated vegetable about pH 7. For example, the compositions of the inven- oils, alkoxylated acetylenic diols, and mixtures thereof. tion may comprise at least one polyarylphenol polyalkox- The ethylene oxide-propylene oxide block copolymers yether sulfate and/or at least one polyarylphenol poly- 50 may comprise alkyl ether bases, such as butyl ether, me- alkoxyether phosphate neutralized to the inflection point thyl ether, propyl ether, ethyl ether, or mixtures thereof. in the titration curve with one or more basic compounds. Commercially available nonionic surfactants include, for [0021] In still other embodiments, the compositions of example, TOXDDUL® 8320 (Stepan Corporation, North- the invention comprise at least one anionic surfactant field, IL) (butyl ether derivative of EO/PO block copoly- selected from polyarylphenol polyalkoxyether sulfates 55 mer) and WITCONOL® NS 500LQ (Crompton Corpora- and polyarylphenol polyalkoxyether phosphates neutral- tion, Greenwich, CT) (butyl ether derivative of EO/PO ized to the inflection point in the titration curve with one block copolymer). or more basic compounds; and one or more additional [0024] The nonionic surfactants may be used in an

4 7 EP 1 423 001 B1 8 amount of 0 to about 8% by weight. In other embodi- present, milling a slurry of the active compound, water, ments, the nonionic surfactants may be used in an defoamer, and all or a portion of the water soluble sur- amount of more than 0 to 8% by weight, preferably in an factants may be indicated to achieve the desired particle amount of 0.1% by weight to 8% by weight, more pref- size. The particle size may be an average particle size erably in an amount of 0.5% by weight to 8% by weight, 5 of about 1 to about 20 microns, preferably about 1 to still more preferably in an amount of 0.5% by weight to about 15 microns, more preferably about 2 to about 10 3% by weight. microns. [0025] The herbicidally active compound is known in [0029] For oil-based products, the surfactant systems the art. The term may also apply to a compound that used according to the invention may be made by com- reduces the phytotoxic response to a herbicide (e.g.,10 bining the oil soluble surfactants with oily liquid active safener selected from benoxacor, cloquintocet, dichlo- compound, oil miscible/oil soluble solvents, and oil insol- rmid, fenclorim, fluxofenime, furilazole, oxabetrinil, salts uble solid active compounds. If an oil insoluble solid ac- thereof, or a mixture thereof). tive compound is present, it may be necessary to mill a [0026] The herbicidally active compounds may be slurry of the active compound, an oil or solvent, and a present in the compositions of the invention in an amount 15 portion or all of the oil soluble surfactants to obtain the of 1 to 75% by weight, preferably an amount of 5 to 70% desired particle size. The particle size may be an average by weight, more preferably in an amount of 10 to 65% by particle size of about 1 to about 20 microns, preferably weight, still more preferably in an amount of 10 to 40% about I to about 1S microns, more preferably about 2 to by weight. In other embodiments, the active compounds about 10 microns. may be present in the compositions of the invention in 20 [0030] Methods for making the surfactant systems of an amount of 50 to 65% by weight. It has been unexpect- the invention are also described in Examples 1-4. edly discovered that a broad range of active compounds [0031] It has also been unexpectedly discovered that may be used in the compositions of the invention to pro- the herbicidal compositions of the invention may be vide stable compositions. For example, the active com- mixed with water to form stable suspoemulsions. For ex- pounds may be water-soluble, oil- soluble, or insoluble in 25 ample, stable suspoemulsions will be formed in very soft water and oil. Thus, the compositions of the invention water (i.e., water containing 0 ppm calcium carbonate may contain active compounds that are water-soluble, equivalent)to very hard water (e.g., water containingover oil/solvent-soluble, and/or insoluble in water and oil/sol- 2,000 ppm calcium carbonate equivalent). Suspoemul- vent. The active compounds may be present in the com- sions have a liquid aqueous phase, which is generally a positions of the invention in the form of, for example, finely 30 continuous phase, a liquid oil phase, which is generally dispersed solids. In other embodiments, the active com- a discontinuous phase dispersed in the aqueous phase, pounds may be dispersed in a liquid phase. and a solid particulate phase, which is a discontinuous [0027] The compositions of the invention may further phase dispersed in one or both of the liquid phases. comprise other inert additives. Such additives include [0032] The herbicidal compositions of the invention thickeners, flow enhancers, wetting agents, antifoaming 35 may be used as flowable concentrates (which include agents, buffers, lubricants, fillers, drift control agents, suspoemulsions, aqueous suspension concentrates, deposition enhancers, adjuvants, evaporation retard- aqueous emulsion concentrates, and oil miscible flowa- ants, frost protecting agents, insect attracting odor ble concentrates), water-in-oil emulsions, capsule emul- agents, UV protecting agents, fragrances, and the like. sions and polyner-stabilized emulsions. Flowable con- The: thickener may be a compound that is soluble or able 40 centrates are often used for seed treatments. to swell in water, such as, for example, polysaccharides [0033] The herbicidal compositions of the invention of xanthans (e.g., anionic heteropolysaccharides), alig- may be used in conventional agricultural methods. For nates, guars or celluloses; synthetic macromolecules, example, the herbicidal compositions of the invention such as polyethylene glycols, polyvinyl pyrrolidones, pol- may be mixed with water and/or fertilizers and may be yvinyl alcohols, polycarboxylates of swellable structure- 45 applied preemergence and/or postemergence to a de- forming silicates such as pyrogenic or precipitated silicic sired locus by any means, such as airplane spray tanks, acids, bentonites, montmoriflonites, hectonites, or atta- knapsack spray tanks, cattle dipping vats, farm equip- pulgites; or organic derivatives of aluminum silicates. The ment used in ground spraying (e.g., boom sprayers, hand frost protecting agent may be, for example, ethylene gly- sprayers), and the like. The desired locus may be soil, col, propylene glycol, glycerol, diethylene glycol, trieth- 50 plants, and the like. The term "plants" includes seeds, ylene glycol, tetraethylene glycol, urea, or mixtures there- seedlings, saplings, roots, tubers, stems, stalks, foliage of. The antifoaming agent may be, for example, a poly- and fruits. dimethylsiloxane. [0034] Preferably, in the herbicidal compositions of the [0028] For water-based products, the surfactant sys- invention, the at least one agriculturally active compound tems used according to the invention may be made by 55 is present in an amount of 1 to 75% by weight; the at combining water-soluble surfactants, water-soluble ac- least one alkyl polyglycoside is present in an amount of tive compounds, water- insoluble solid active compounds 0.1 to 8% by weight; the at least one anionic surfactant and water. If a water-insoluble solid active compound is is present in an amount of 0.1 to 8% by weight; and the

5 9 EP 1 423 001 B1 10 at least one basic compound is present in an amount of [0040] An aqueous premix was prepared by stirring 0.1 to 8% by weight. together 23 grams of SOPROPHOR® 3D33 with 7 grams [0035] More preferably, in the herbicidal compositions of TOXIMUL®) TA-2, next adding 242.8 grams of water, of the invention, the at least one agriculturally active com- and then adding 229 grams of technical atrazine. Stirring pound is present in an amount of 15 to 70% by weight; 5 was continued until a uniform, fluid slurry was obtained. the at least one alkyl glycoside is present in an amount [0041] An S-metolachlor/benoxacor premix was made of 0.5 to 4% by weight; the at least one anionic surfactant by allowing 9 grams of benoxacor to dissolve into 187 is present in an amount of 1 to 4% by weight; and the at grams of s-metolachlor. Thereafter, 10 grams of BIO- least one basic compound is present in an amount of 0.5 SOFT® S-101 and 5 grams of WITCAMINE® TAM-80 to 4% by weight. 10 were added and stirred until totally dissolved. [0036] Even more preferably, in the herbicidal compo- [0042] The S-metolachlor premix and the aqueous sitions of the invention, the at least one agriculturally ac- premix were blended together simultaneously with good tive compound is present in an amount of 15 to 70% by agitation. weight; the at least one alkyl glycoside is present in an [0043] A solution was made from 108 grams glypho- amount of 0.5 to 4% by weight; the at least one anionic 15 sate isopropylamine salt in 66 grams of water. This was surfactant is present in an amount of 1 to 4% by weight; then added to the previous mixture. Next, 20 grams of the at least one basic compound is present in an amount AGRIMUL® PG 2067 was added to the mixture. of 0.5 to 4% by weight; and the at least one nonionic [0044] With good agitation, a dispersion of 1 gram of surfactant is present in an amount of 0.5 to 3% by weight. RHODOPOL® 23 and 0.5 grams of PROXEI® GXL were 20 prepared in 88.7 grams of water. The mixture was agi- Examples tated until full swelling of the RHODOPOL® 23 occurred. This dispersion was then added with stirring to the mix- [0037] The following examples are for purposes of il- ture previously described. To control foaming, 3 grams lustration only and are not intended to limit the scope of of Dow Corning Antifoam 1500 was added. the appended claims. 25 [0045] The resulting composition exhibited good phys- [0038] Generally, the compositions in the examples ical stability and fertilizer compatibility. were prepared by first preparing a series of premixes and blending the premixes to prepare the final composition. Example 2 Glyphosate isopropylamine salt was used as a 62% solution in water. Atrazine was used in a finely ground, com- 30 [0046] A composition was prepared with the following mercially-available form (i.e., more than 98% of the par- components: ticles are less than 44 microns in diameter). In the examples, the percentages are percentages by weight. 64.4% agriculturally active compounds (comprising 16.2% atrazine, 42.2% S-metolachlor, 2.1% benox- Example; 1 35 acor, 3.9% butafenacil); 0.9% tristyrylphenol polyethoxyether phosphate [0039] A composition was prepared with the following (SOPROPHOR® 3D33); components: 3.3% alkyl polyglycoside (AGRIMUL®) PG 2069); 1.5% butanol copolymer PO/EO (TOXIMUL® 8320); 53.2% agriculturally active compounds (comprising 40 0.8% tridecyl alcohol polyethoxyether phosphate 22.9% atrazine, 18.7% S-metolachlor, 0.9% benox- (STEPFAC® 8181); acor, and 10.8% glyphosate isopropylamine salt); 1% mixture of tristyrylphenol (EO) 8 sulfate and tal- 2.3% tristyrylphenol polyethoxyether phosphate lowamine (EO) 5 (DV-4636); (SOPROPHOR® 3D33); 1.5% linoleic diethanolamide (WITCAMIDE® 511); 0.7% tallow amine ethoxylate (2 moles EO) (TOX- 45 2.0% ethylene glycol; IMUL® TA-2); 0.03% anionic heteropolysaccharide (RHO- 2.0% alkyl polyglycoside (AGRIMUL® PG 2067); DOPOL® 23); 1.0% dodecylbenzene sulfonic acid (BIOSOFT® S- 0.03% 1,2-benaisothiazolin-3-one (PROXEL® 101); GXL); 0.5% tallow amine ethoxylate (8 moles EO) (WIT- 50 0.1 % polydimethylsiloxane (Dow Corning Antifoam CAMINE® TAM-80); 1500); and 0.1% anionic heteropolysaccharide (RHODOPOL® 24.44% water. 23); 0.05% 1,2-beztzisothiazolin-3-one (PROXEL® [0047] An aqueous premix was made by slurrying to- GXL); 55 gether 9 grams of SOPROPHOR® 3D33, 8 grams of 0.3% polydimethylsiloxane (Dow Corning Antifoam STEPFAC® 8181,15 grams of WTTCAMTDE® 511, and 1500); and 20 grams of ethylene glycol. Next, 200 grams of water 39.85% water. was added and stirred until uniform. Then, 162 grams of

6 11 EP 1 423 001 B1 12 technical atrazine was added and the premix was stirred [0055] The aqueous premix was added to the S-me- until uniform. tolachlor premix with continuous stirring and was blended [0048] An S-metolachlor premix was made by allowing until uniform. Next, 33 grams of AGRlMUL® PG 2069 21 grams of benoxacor, and 39 grams of butafenacil to were added. dissolve into 422 grams of S-metolachlor. To this solu- 5 [0056] An aqueous pregel was prepared by adding 0.3 tion, 15 grams of TOXIMUL® 8320 and 10 grams of DV- grams of RHODOPOL® 23 and 0.3 grams of PROXEL® 4636 were added and allowed to mix until uniform. GXL to 15.4 grams of water. The aqueous pregel was [0049] The aqueous premix and the metolachlor S- added to the mixture previously described. 1 gram of Dow premix were blended together until uniform using good Corning Antifoam 1500 was added to control foaming. agitation. To this mixture, 33 grams of AGRIMUL® PG- 10 [0057] The resulting composition exhibited good phys- 2069 were added. ical stability and fertilizer compatibility. [0050] An aqueous pregel was prepared by adding 0.3 grams of RHODOPOL® 23 and 0.3 grams of PROXEL® Example 4 GXL to 44.4 grams of water with vigorous agitation. Ag- itation was continued until the RHODOPOL® 15 23[0058] A composition was prepared with the following achieved full swelling. This mixture was added to the mix- components: ture previously described. 1 gram of Dow Corning Anti- foam 1500 was added to control foaming. 61.11% agriculturally active compounds (comprising [0051] The resulting composition exhibited good phys- 33.7% atrazine technical; 26.1% S-metolachlor and ical stability and fertilizer compatibility. 20 1.31% benoxacor); 1.7% tridecyl alcohol (EO) 6 phosphate (STEPFAC® Example 3 8181); 1% tallowamine (EO) 2 (TOXIMUL® TA-2); [0052] A composition was prepared with the following 0.3% mixture of tristyrylphenol (EO) 8 sulfate and components: 25 tallowamine (EO) 5 (DV-4636); 0.3% tristyryl phenol (EO) 25 (SOPROPHOR® S- 57.3% agriculturally active compounds (comprising 25); 28.6% atrazine; 24.9% S-metolachlor; 1.2% benox- 1.8% butoxy EO/PO block copolymer (WITCONOL® acor; 2.6% butafenacil); NS500LQ); 30 0.9% tnistyrylphenol polyethoxyether phosphate 1 % alkylpolyglycoside 9-11 (C) (AGRIMUL® (SOPROPHOR® 3D33); PG2069); 3.3% alkyl polyglycoside (AGRIMUL® PG 2069); 1% attapulgite clay (ATTAFLOW® FL); 1.5% butanol copolymer PO/EO (TOXIMUL® 8320); 0.67% tridecyl alcohol (EO) 6 (RENEX® 36); 0.8% tridecyl alcohol polyethoxyether phosphate 0.22% EO/PO block polymer (STEPFAC® 8323); (STEPFAC® 8181); 35 1.75% ethylene glycol; 1% mixture of tristyrylphenol (EO) 8 sulfate and tal- 0.1% silicons-based oil (Antifoam A); lowamine (EO) 5 (DV-4636); 0.03% 1,2-benzisothiazolin-3-one (PROXEL® 1.5% linoleic diethanolamide (WITCAMIDE® 511); GXL); 2.0% ethylene glycol; 0.03% xantham gum (RHODOPOL® 23); 0.03% anionic heteropolysaccharide (RHO-40 28.99% water. DOPOL® 23) 0.03% 1,2-benzisothiazolin-3-one (PROXEL® [0059] An aqueous premix was made by mixing 200 GXL); grams of water with 6.7 grams of RENEX® 36, 2.2 grams 0.1 % polydimethylsiloxane (Dow Corning Antifoam STEPFAC® 8323, 1 gram of Antifoam A and 17.5 grams 1500); and 45 of ethylene glycol. Next, 337 grams of technical atrazine 31.54% water. were added. The mixture was blended until uniform. [0060] An S-metolachlor premix was made by allowing [0053] An aqueous premix was prepared by mixing 9 13.1 grams of benoxacor to dissolve into 261 grams of grams of SOPROPHOR® 3D33, 8 grams of STEPFAC® S-metolachlor. Then, 17 grams of STEPFAC® 8181, 10 8181,15 grams of WITCAMID® 511, and 20 grams of 50 grams of TOXBFUL® TA-2, 3 grams of DV-4636, 18 ethylene glycol. This mixture was stirred until uniform. grams of WITCONOL® NS500LQ, and 3 grams of SO- Next, 300 grams of water were added, followed by the PROPHOR® S-25 were added with continuous mixing. addition of 286 grams of atrazine technical. [0061] The S-metolachlor premix was added to the [0054] An S-rnetolachlor premix was made by allowing aqueous premix and blended until uniform. 12 grams of benoxacor and 26 grams of butafenacil to 55 [0062] An aqueous pregel was prepared by adding 0.3 dissolve into 249 grams of S-metolachlor. Next 15 grams grams of PROXEL® GXL and 0.3 grams of RHO- of TOXIMUL® 8320 and 10 grams of DV- 4636 were add- DOPOL® 23 to 89.9 grams of water. The mixture was ed. agitated vigorously until the RHODOPOL® 23 swelled

7 13 EP 1 423 001 B1 14 completely. The aqueous pregel was added to the mix- tralized to the injection point in the titration curve with ture described in the previous paragraph. 10 grains of the at least one basic compound. AGR1MUL® PG2069 and 10 grams of ATTAFLOW® FL were added to complete the formulation. 2. The herbicidal composition of claim 1, further com- [0063] The resulting composition exhibited good phys- 5 prising at least one nonionic surfactant. ical stability and fertilizer compatibility. 3. The herbicidal composition of claim 1, wherein the polyarylphenol polyalkoxyether sulfate is a polyaryl- Claims phenol polyethoxyether sulfate and the polyarylphe- 10 nol polyalkoxyether phosphate is a polyarylphenol 1. A herbicidal composition comprising polyethoxyether phosphate. at least one herbicidally active compound selected from glyphosate; S-metolachlor; atrazine; glufosi- 4. The herbicidal composition of claim 3, wherein the nate; acetochlor; mesotrione; glyphosate and S- me- polyarylphenol polyethoxyether sulfate is a tristyryl- tolachlor; glyphosate, S-metolachlor and atrazine; 15 phenol polyethoxyether sulfate, and the polyarylphe- glyphosate, S-metolachlor, atrazine and benoxacor; nol polyethoxyether phosphate is a tristyrylphenol S-metolachlor and atrazine; S- metolachlor, atrazine polyethoxyether phosphate. and benoxacor; metolachlor, S- atrazine and butavenacil; S-metolachlor, atrazine, benoxacor and 5. The herbicidal composition of claim 1, wherein the 20 butafenacil; glyphosate, acetochlor and atrazine; basic compound is an inorganic base, a C8-18 alkyl glyphosate, S-metolachlor and atrazine; glufosinate, amine polyalkoxylate, an alkanol amine, an alkanol acetochlor and atrazine; glufosinate, S-metolachlor amide, or a mixture thereof. and atrazine; mesotrione and S-metolachlor; mesotrione, S-metolachlor and benoxacor; mesotrione, 6. The herbicidal composition of claim 5, wherein the S-metolachlor and atrazine; or mesotrione, S-metol- 25 basic compound is a tallow amine ethoxylate, a co- achlor, benoxacor and atrazine. ; coamine ethoxylate, a oleylamine ethoxylate, a at least one alkyl polyglycoside; stearylamine ethoxylate, a linoleic ctiethanolamide, at least one fertilizer, which comprises nitrogen, or a mixture thereof. phosphorous and/or potassium; at least one anionic surfactant selected from a pol- 30 7. The herbicidal composition of claim 2, wherein the yarylphenol polyalkoxyether sulfate and a polyaryl- nonionic surfactant is an ethylene oxide-propylene phenol polyalkoxyether phosphate; and oxide block copolymer, ethylene oxide- butylene ox- at least one basic compound; ide block copolymer, a C 2-6 alkyl adduct of an ethyl- wherein the alkyl polyglycoside is a compound of ene oxide-propylene oxide block copolymer, a C2-6 formula (TT): 35 alkyl adduct of an ethylene oxide-butylene oxide block copolymer, a polypropylene glycol, a polyethylene glycol, a polyarylphenol polyethoxy ether, a polyalkylphenol polyethoxy ether, a polyglycol ether derivative of a saturated fatty acid, a polyglycol ether 40 derivative of an unsaturated fatty acid, a polyglycol ether derivative of an aliphatic alcohol, a polyglycol ether derivative of a cycloaliphatic alcohol, a fatty acid ester of polyoxyethylene sorbitan, an alkoxylated vegetable oil, an alkoxylated acetylenic diol, or a 45 mixture thereof.

8. The herbicidal composition of claim 1, wherein the at least one herbicidally active compound is present in an amount of 1 to 75% by weight; the at least one 50 alkyl polyglycoside is present in an amount of 0.1 to 8% by weight; the at least one anionic surfactant is where n is the degree of polymerization and is from present in an amount of 0.1 to 8% by weight; and 1 to 3, preferably 1 or 2, and 5R is a branched or the at least one basic compound is present in an straight chain alkyl group having from 4 to 18 carbon amount of 0.1 to 8% by weight. atoms or a mixture of alkyl groups having from 4 to 55 18 carbon atoms; 9. The herbicidal composition of claim 8, wherein the and at least one herbicidally active compound is present wherein the at least one anionic surfactant is neu- in an amount of 15 to 70% by weight; the at least

8 15 EP 1 423 001 B1 16

one alkyl glycoside is present in an amount of 0.5 to Benoxacor; 4% by weight; the at least one anionic surfactant is Mesotrion, S-Metolachlor und Atrazin; oder Me- present in an amount of 1 to 4% by weight; and the sotrion, S-Metolachlor, Benoxacor und Atrazin; at least one basic compound is present in an amount mindestens ein Alkylpolyglycosid; of 0.5 to 4% by weight. 5 mindestens einen Dünger, der Stickstoff, Phos- phor und/oder Kalium umfasst; 10. The herbicidal composition of claim 9, wherein the mindestens ein anionisches Tensid aus der Rei- at least one herbicidally active compound is present he Polyarylphenolpolyalkoxyethersulfat und in an amount of 15 to 70% by weight; the at least Polyarylphenolpolyalkoxyetherphosphat; und one alkyl glycoside is present in an amount of 0.5 to 10 mindestens eine basische Verbindung; 4% by weight; the at least one anionic surfactant is wobei es sich bei dem Alkylpolyglycosid um eine present in an amount of 1 to 4% by weight; the at Verbindung der Formel (II) handelt: least one basic compound is present in an amount of 0.5 to 4% by weight; and the at least one nonionic surfactant is present in an amount of 0.5 to 3% by 15 weight.

11. The herbicidal composition of claim 1, which addi- tionally contains as the safener benoxacor, cloquintocet, dichlormid, fenclorim, fluxofenime, furilazole, 20 oxabetrinil, salts thereof, or a mixture thereof.

12. The herbicidal composition of claim 1, further comprising water. 25 13. The herbicidal composition of claim 1, further comprising a thickener.

14. The herbicidal composition, of claim 1, further com- worin n den Polymerisationsgrad bedeutet und prising an anti-foaming agent. 30 1 bis 3, vorzugsweise 1 oder 2, bedeutet, und R5 eine verzweigt- oder geradkettige Alkylgrup- 15. The herbicidal composition of claim 1, further com- pe mit 4 bis 18 Kohlenstoffatomen oder eine Mi- prising a frost protecting agent. schung aus Alkylgruppen mit 4 bis 18 Kohlen- stoffatomen bedeutet; 35 und Patentansprüche wobei das mindestens eine anionische Tensid mitder mindestens einenbasischen Verbindung 1. Herbizide Zusammensetzung, die Folgendes um- zum Wendepunkt der Titrationskurve neutrali- fasst: siert wird. 40 mindestens einen Herbizidwirkstoff aus der Rei- 2. Herbizide Zusammensetzung nach Anspruch 1, die he Glyphosate; S-Metolachlor, Atrazin; Glufosi- weiterhin mindestens ein nichtionisches Tensid um- nate; fasst. Acetochlor; Mesotrion; Glyrphosate und S-Me- tolachlor; 45 3. Herbizide Zusammensetzung nach Anspruch 1, wo- Glyphosate, S-Metolachlor und Atrazin; Glypho- bei es sich bei dem Polyarylphenolpolyalkoxyether- sate, S-Metolachlor, Atrazin und Benoxacor; S- sulfat um ein Polyarylphenolpolyethoxyethersulfat Metolachlor und und bei dem Polyarylphenolpolyalkoxyetherphos- Atrazin; S-Metolachlor, Atrazin und Benoxacor; phat um ein Polyarylphenolpolyethoxyetherphos- S-Metolachlor, Atrazin und Butavenacil; S-Me- 50 phat handelt. tolachlor, Atrazin, Benoxacor und Butafenacil; Glyphosate, 4. Herbizide Zusammensetzung nach Anspruch 3, wo- Acetochlor und Atrazin; Glyphosate, S-Metola- bei es sich bei dem Polyarylphenolpolyethoxyether- chlor und sulfat um ein Tristyrylphenolpolyethoxyethersulfat Atrazin; Glufosinate, Acetochlor und Atrazin; 55 und bei dem Polyarylphenolpolyethoxyetherphos- Glufosinate, S-Metolachlor und Atrazin; Me- phat um ein Tristyrylphenolpolyethoxyetherphos- sotrion und phat handelt. S-Metolachlor; Mesotrion, S-Metolachlor und

9 17 EP 1 423 001 B1 18

5. Herbizide Zusammensetzung nach Anspruch 1, wo- von 0,5 bis 3 Gew.-% vorliegt. bei es sich bei der basischen Verbindung um eine anorganische Base, ein C 8-18-Alkylaminpolyalkoxy- 11. Herbizide Zusammensetzung nach Anspruch 1, die lat, ein Alkanolamin, ein Alkanolamid oder eine Mi- zusätzlich als Safener Benoxacor, Cloquintocet, Di- schung davon handelt. 5 chlormid, Fenclorim, Fluxofenim, Furilazol, Oxaber- rinil, Salze davon oder eine Mischung davon enthält. 6. Herbizide Zusammensetzung nach Anspruch 5, wobei es sich bei der basischen Verbindung um ein 12. Herbizide Zusammensetzung nach Anspruch 1, die Talgaminethoxylat, ein Kokosaminethoxylat, ein weiterhin Wasser umfasst. Oleylaminethoxylat, ein Stearylaminethoxylat, ein 10 Linolsäurediethanolamid oder eine Mischung davon 13. Herbizide Zusammensetzung nach Anspruch 1, die handelt. weiterhin ein Verdickungsmittel umfasst.

7. Herbizide Zusammensetzung nach Anspruch 2, wo- 14. Herbizide Zusammensetzung nach Anspruch 1, die bei es sich bei dem nichtionischen Tensid um ein 15 weiterhin ein Antischaummittel umfasst. Ethylenoxid-Propylenoxid-Blockcopolymer, ein Ethylenoxid-Butylenoxid-Blockcopolymer, ein 15. Herbizide Zusammensetzung nach Anspruch 1, die C2-6-Alkyladdukt eines Ethylenoxid-Propylenoxid- weiterhin ein Frostschutzmittel umfasst. Blockcopolymers, ein C2-6-Alkyladdukt eines Ethy- lenoxid-Butylenoxid-Blockcopolymers, ein Polypro- 20 pylenglycol, ein Polyethylenglycol, einen Polyaryl- Revendications phenolpolyethoxyether, einen Polyalkylphenolpo- lyethoxyether, ein Polyglycoletherderivat einer ge- 1. Composition herbicide comprenant au moins un sättigten Fettsäure, ein Polyglycoletherderivat einer composé actif du point de vue herbicide, choisi parmi ungesättigten Fettsäure, ein Polyglycoletherderivat 25 le glyphosate ; le S-métolachlore ; l’atrazine ; le eines aliphatischen Alkohols, ein Polyglycoletherde- glufosinate ; l’acétochlore ; la mésotrione ; le gly- rivat eines cycloaliphatischen Alkohols, einen phosate, et le S-métolachlore ; le glyphosate, le S- Polyoxyethylensorbitanfettsäureester, ein alkoxy- métolachlore et l’atrazine ; le glyphosate, le S-mé- liertes pflanzliches Öl, ein alkoxyliertes Alkindiol tolachlore, l’atrazine et le bénoxacor ; le S-métola- oder eine Mischung davon handelt. 30 chlore et l’atrazine ; le S-métolachlore, l’atrazine et le bénoxacor ; le S-métolachlore, l’atrazine et le 8. Herbizide Zusammensetzung nach Anspruch 1, wo- butafenacil ;le S- métolachlore, l’atrazine, le bénoxa- bei der mindestens eine Herbizidwirkstoff in einer cor et le butafenacil ; le glyphosate, l’acétochlore et Menge von1 bis 75Gew.- % vorliegt; das mindestens l’atrazine ; le glyphosate, le métolachlore S- et eine Alkylpolyglycosid in einer Menge von 0,1 bis 8 35 l’atrazine ; le glufosinate, l’acétochlore, et l’atrazine ; Gew.-% vorliegt; das mindestens eine anionische le glufosinate, le S- métolachlore et l’atrazine ; la mé- Tensid in einer Menge von 0,1 bis 8 Gew.- % vorliegt; sotrione et le S-médaochlore ; la mésotrione, le S- und die mindestens eine basische Verbindung in ei- métolachlore et le bénoxacor ; la mésotrione, le S- ner Menge von 0,1 bis 8 Ges.-% vorliegt. métolachlore et l’atrazine ; ou la mésotrione, le S- 40 métolachlore, le bénoxacor et l’atrazine ; 9. Herbizide Zusammensetzung nach Anspruch 8, wo- au moins un alkylpolyglycoside ; bei der mindestens eine Herbizidwirkstoff in einer au moins un engrais, qui comprend l’azote, le phos- Menge von 15 bis 70 Gew.-% vorliegt; das minde- phore et/ou le potassium ; stens eine Alkylglycosid in einer Menge von 0,5 bis au moins un tensioactif anionique choisi parmi un 4 Gew.-% vorliegt; das mindestens eine anionische 45 polyalcoxyéthersulfate de polyarylphénol et un po- Tensid in einer Menge von 1 bis 4 Gew.-% vorliegt; lyalcoxyétherphosphate de polyarylphénol ; et und die mindestens eine basische Verbindung in ei- au moins un composé basique ; ner Menge von 0,5 bis 4 Gew.-% vorliegt. où l’alkylpolyglycoside est un composé de formule (II) : 10. Herbizide Zusammensetzung nach Anspruch 9, wo- 50 bei der mindestens eine Herbizidwirkstoff in einer Menge von 15 bis 70 Gew.-% vorliegt; das mindestens eine Alkylglycosid in einer Menge von 0,5 bis 4 Gew.-% vorliegt; das mindestens eine anionische Tensid in einer Menge von 1 bis 4 Gew.-% vorliegt; 55 die mindestens eine basische Verbindung in einer Menge von 0,5 bis 4 Gew.-% vorliegt; und das mindestens eine nichtionische Tensid in einer Menge

10 19 EP 1 423 001 B1 20

un copolymère séquencé oxyde d’éthylène-oxyde de propylène, un copolymère séquencé oxyde d’éthylène-oxyde de butylène, un adduit d’alkyle en C2-6 d’un copolymère séquencé oxyde d’éthylène- 5 oxyde de propylène, un adduit d’alkyle en C 2-6 d’un copolymère séquencé oxyde d’éthylène-oxyde de butylène, un polypropylèneglycol, un polyéthylène- glycol, un polyéthoxyéther de polyarylphénol, un po- lyéthoxyéther de polyalkylphénol, un dérivé d’éther 10 de polyglycol d’un acide gras saturé, un dérivé d’éther de polyglycol d’un acide gras insaturé, un dérivé d’éther de polyglycol d’un alcool aliphatique, un dérivé d’éther de polyglycol d’un alcool cycloali- phatique, un ester d’acide gras de polyoxyéthylène 15 sorbitan, une huile végétale alcoxylée, un diol acé- dans laquelle n est le degré de polymérisation et est tylénique alcoxylé, ou un mélange de ceux-ci. de 1 à 3, de préférence 1 ou 2, et R 5 est un groupe- ment alkyle à chaîne ramifiée ou droite ayant de 4 à 8. Composition herbicide selon la revendication 1, ca- 18 atomes de carbone ou un mélange de groupe- ractérisée en ce que ledit au moins un composé ments alkyle ayant de 4 à 18 atomes de carbone ; 20 actif du point de vue herbicide est présent dans une et quantité de 1 à 75% en poids ; ledit au moins un où ledit au moins un tensioactif anionique est neu- alkylpolyglycoside est présent dans une quantité de tralisé au point d’inflexion dans la cuve de titration 0,1 à 8 % en poids ; ledit au moins un tensioactif avec ledit au moins un composé basique. anionique est présent dans une quantité de 0,1 à 8 25 % en poids ; et ledit au moins un composé basique 2. Composition herbicide selon la revendication 1, est présent dans une quantité de 0,1 à 8 % en poids. comprenant en outre au moins un tensioactif nonio- nique. 9. Composition herbicide selon la revendication 8, ca- ractérisée en ce que ledit au moins un composé 3. Composition herbicide selon la revendication 1, ca- 30 actif du point de vue herbicide est présent dans une ractérisée en ce que le polyalcoxyéthersulfate de quantité de 15 à 70% en poids ; ledit au moins un polyarylphénol est un polyéthoxyéthersulfate de po- alkylglycoside est présent dans une quantité de 0,5 lyarylphénol et le polyalcoxyétherphosphate de po- à 4 % en poids ; ledit au moins un tensioactif anio- lyarylphénol est un polyéthoxyétherphosphate de nique est présent dans une quantité de 1 à 4 % en polyarylphénol. 35 poids ; et ledit au moins un composé basique est présent dans une quantité de 0,5 à 4 % en poids. 4. Composition herbicide selon la revendication 3, ca- ractérisée en ce que le polyéthoxyéthersulfate de 10. Composition herbicide selon la revendication 9, ca- polyarylphénol est un polyéthoxyéthersulfate de tris- ractérisée en ce que ledit au moins un composé tyrylphénol, et le polyéthoxyétherphosphate de po- 40 actif du point de vue herbicide est présent dans une lyarylphénol est un polyéthoxyétherphosphate de quantité de 15 à 70% en poids ; ledit au moins un tristyrylphénol. alkylglycoside est présent dans une quantité de 0,5 à 4 % en poids ; ledit au moins un tensioactif anio- 5. Composition herbicide selon la revendication 1, ca- nique est présent dans une quantité de 1 à 4 % en ractérisée en ce que le composé basique est une 45 poids ; ledit au moins un composé basique est pré- base minérale, un polyalcoxylate de C 8-18 alkylami- sent dans une quantité de 0,5 à 4 % en poids ; et ne, une alkanolamine, un alkanolamide, ou un mé- ledit au moins un tensioactif non ionique est présent lange de ceux-ci. dans une quantité de 0,5 à 3 % en poids.

6. Composition herbicide selon la revendication 5, ca- 50 11. Composition herbicide selon la revendication 1, ca- ractérisée en ce que le composé basique est un ractérisée en ce qu’ elle contient en outre, à titre de éthoxylate de tallowamine, un éthoxylate de cocoa- phytoprotecteur, le bénoxacor, le cloquintocet, le di- mine, un éthoxylate d’oleylamine, un éthoxylate de chlormide, le fenclorim, le fluxofénime, le furilazole, stéarylamine, un diéthanolamide linoléique, ou un l’oxabétrinil, les sels de ceux-ci, ou un mélange de mélange de ceux-ci. 55 ceux-ci.

7. Composition herbicide selon la revendication 2, ca- 12. Composition herbicide selon la revendication 1, ractérisée en ce que le tensioactif non ionique est comprenant en outre de l’eau.

11 21 EP 1 423 001 B1 22

13. Composition herbicide selon la revendication 1, comprenant en outre un épaississant.

14. Composition herbicide selon la revendication 1, comprenant en outre un agent anti-mousse. 5

15. Composition herbicide selon la revendication 1, comprenant en outre un agent de protection contre le gel. 10

12 EP 1 423 001 B1

REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• WO 0035863 A [0003] • WO 9608150 A [0004]