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Wo 2009/021985 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date PCT 19 February 2009 (19.02.2009) WO 2009/021985 A2 (51) International Patent Classification: (74) Agent: Patentanwalte Reitstδtter Kinzebach; Stern- AOlN 25/30 (2006.01) AOlN 47102 (2006.01) wartstr. 4, 81679 Munchen (DE). AOlN 25/04 (2006.01) AOlN 43/653 (2006.01) AOlN 53/00 (2006.01) AOlP 3/00 (2006.01) (81) Designated States (unless otherwise indicated, for every AOlN 47/24 (2006.01) AOlP 7/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, (21) International Application Number: CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, PCT/EP2008/060672 EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, (22) International Filing Date: 14 August 2008 (14.08.2008) LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, (25) Filing Language: English RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY,TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (26) Publication Language: English ZW (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 071 14462.0 16 August 2007 (16.08.2007) EP GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (71) Applicant (for all designated States except US): BASF SE European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, [-/DE]; 67056 Ludwigshafen (DE). FR, GB, GR, HR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, NO, PL, PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, (72) Inventors; and CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (75) Inventors/Applicants (for US only): ISRAELS, Rafel [NL/DE]; Roonstrasse 61, 50674 KoIn (DE). KLAM- Declaration under Rule 4.17: CZYNSKI, Katharine [PL/DE]; Forststrasse 4, 67459 — as to the applicant's entitlement to claim the priority of the Bohl-Iggelheim (DE). BRATZ, Matthias [DE/DE]; earlier application (Rule 4.17(Hi)) Kurpfalzstrasse 41, 67133 Maxdorf (DE). SCHLOTTER- BECK, UIf [DE/DE]; Burgstrasse 20, 68165 Mannheim Published: (DE). VOESTE, Dirk [DE/DE]; Berliner Platz 11, 671 17 — without international search report and to be republished Limburgerhof (DE). upon receipt of that report (54) Title: SEED TREATMENT COMPOSITIONS AND METHODS (57) Abstract: The invention relates to seed treatment compositions comprising active ingredient, polyarylphenol polyalkoxy ether phosphate and/or polyarylphenol polyalkoxy ether sulphate, and copolymer having polyalkoxy ether side chains. The polyarylphe- nol polyalkoxy ether phosphate and/or the polyarylphenol polyalkoxy ether sulphate in combination with the copolymer having polyalkoxy ether side chains are used as dispersant, especially to provide a dispersion of suspended active ingredient. The present invention also relates to methods of treating seed with such a composition. Seed treatment compositions and methods The invention relates to seed treatment compositions and methods of treating seed. The invention also relates to the use of polyarylphenol polyalkoxy ether phosphates and/or polyarylphenol polyalkoxy ether sulfates as well as of copolymers having polyalkoxy ether side chains in seed treatment compositions. Seed treatment is the process of applying active ingredients to seeds in order to sup port the germination and/or the growth of a large variety of crops. Typical examples include the application of pesticides such as fungicides, insecticides and plant growth regulators, as well as other active ingredients such as fertilizers. Being an alternative to traditional broadcast spraying of pesticides, seed treatment compositions must fulfil a number of special requirements which include their applica- bility to seeds in commercial equipment, the adhesion of the active ingredients to the treated seeds, and good flowability of the treated seeds. Of course, the treated seeds must still be capable of germination. A number of compositions widely used for seed treatment are dispersions. Such com- positions require one or more dispersants to lower the viscosity and to stabilize the dispersion against agglomeration and crystal growth. WO 2005/036963 describes suspension concentrates comprising an azole and/or a strobilurine, a penetration promoter from the alkanol alkoxylate group, a dispersant, water, and optionally further auxiliaries. The dispersant is a polymerisate of 2-methyl-2- propenoic acid methyl ether and α-(2-methyl-1-oxo-2-propenyl)- ω-methoxy-poly-(oxy- 1,2-ethandiyl) or a tristyrylphenol-ethoxylate and/or a propylene oxide-ethylene oxide block copolymer with a molecular weight from 8.000 to 10.000. The compositions are said to be useful for treating plants, seed and soil. Although the use of dispersants in seed treatment compositions is well-known in the art, the commonly used dispersants tend to provide seed treatment compositions which are not entirely satisfactory. It is especially the combination of seed-specific and gen eral requirements for seed treatment compositions that remains hard to achieve. An object of the present invention was to provide a seed treatment composition that is capable of forming a stable dispersion and suitable for seed treatment. Surprisingly, it has now been found that a combination of a polyarylphenol polyalkoxy ether phosphate and/or a polyarylphenol polyalkoxy ether sulfate with a copolymer hav- M/48201 ing polyalkoxy ether side chains forms an excellent dispersing system for a large num ber of agrochemicals in seed treatment compositions. The invention therefore relates to seed treatment compositions comprising active in- gredient, polyarylphenol polyalkoxy ether phosphate and/or polyarylphenol polyalkoxy ether sulphate, and copolymer having polyalkoxy ether side chains. Particular embodi ments of the compositions are defined in the claims and disclosed herein. The compositions of the present invention show a stable particle size of dispersed, in particular suspended, active ingredient(s). As used herein, a "composition" comprises at least one active ingredient and at least one auxiliary agent. As used herein, ingredients comprise active ingredients and auxiliary agents. In the present invention, an "active ingredient" is a compound which directly exerts a biologically relevant effect, preferably a pesticidal effect as described herein. The term "auxiliary agent" refers to a compound or combination of compounds which do not exert a biologically relevant effect of their own, but support the effects of the active ingredient(s). When auxiliary agents are used, their choice will depend on the active ingredients and on the procedures selected for seed treatment. Usually, the compositions thus comprise an active ingredient component ("A") and an auxiliary agent component ("B"). The active ingredient component ("A") of the composi tion comprises one or more than one active ingredient(s). The auxiliary agent compo nent ("B") comprises one or more auxiliary agent(s). As used herein, the term "at least one" refers to 1, 2 , 3 , or more members from a group and includes mixtures of 2 , 3 , or more different members from the group. Unless indicated otherwise, all amounts in % by weight refer to the weight of the total composition (or formulation). In general, the compositions comprise from 0.005% by weight to 95% by weight, pref erably from 0.01% by weight to 90% by weight, in particular from 0.1 or 0.5% by weight to 50% by weight, of the active ingredient component "A", the balance being formed by component "B". In this context, the active ingredients are employed in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum). M/48201 According to the invention, the active ingredient is especially selected from plant pro tection active agents (pesticides). Such an agent has the purpose or effect of prevent ing infection of a plant by any pest or of repelling, deterring or destroying the pest or of reducing in another way the damage caused by it. Plant pests can belong to different groups of organisms; the higher animals, in particular insects and acarids, include nu merous important pests, as do nematodes and snails; vertebrates, such as mammals and birds, are today of secondary importance in industrialized countries. Numerous groups of microbes, including fungi, bacteria, inclusive of mycoplasmas, viruses and viroids, comprise pests, and even weeds, which compete with useful plants for limited habitat and other resources, can be classed as pests in the broad sense. Pesticides comprise in particular aphicides, acaricides, desiccants, bactericides, chemosterilants, defoliants, antifeedants, fungicides, herbicides, herbicide safeners, insect attractants, insecticides, insect repellents, molluscicides, nematicides, mating disrupters, plant acti vators, plant growth regulators, rodenticides, mammal repellents, synergists, bird repel- lents and virucides. The following list of pesticides which can be used according to the invention, is intended to illustrate the possible active ingredients, but not to impose any limitation: A . Insecticides and Acaricides A.1 . Organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion,
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