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Surfactant Systems for Agriculturally Active

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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-me- tolachlor, 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 stor- age 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,
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