AU2003255369A1

AU2003255369A1 - Protectant formulations

Info

Publication number: AU2003255369A1
Application number: AU2003255369A
Authority: AU
Inventors: Rafel Israels; Ulrich Schwiedoip; John Seidel; Bernd Springer
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2002-08-19
Filing date: 2003-08-05
Publication date: 2004-03-29
Also published as: DE10237821A1; WO2004021783A1; AR040976A1

Description

IN THE MATTER OF an Australian Application corresponding to PCT Application PCT/EP2003/008632 RWS Group Ltd, of Europa House, Marsham Way, Gerrards Cross, Buckinghamshire, England, hereby solemnly and sincerely declares that, to the best of its knowledge and belief, the following document, prepared by one of its translators competent in the art and conversant with the English and German languages, is a true and correct translation of the PCT Application filed under No. PCT/EP2003/008632 Date: 4 February 2005 C. E. SITCH Deputy Managing Director - UK Translation Division For and on behalf of RWS Group Ltd (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International publication date (10) International publication number 18 March 2004 (18.03.2004) PCT WO 2004/021783 Al (51) International patent classification 7 : A0IN 25/10, (84) Designated states (regional): ARIPO Patent (GH, GM, 43/653 KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian Patent (AM, AZ, BY, KG, KZ, MD, RU, TJ, (21) International application number: PCT/EP2003/008632 TM), European Patent (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, (22) International filing date: 5 August 2003 (05.08.2003) NL, PT, RO, SE, SI, SK, TR), OAPI Patent (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, (25) Language of filing: German SN, TD, TG). (26) Language of publication: German Declarations under Rule 4.17: - As to applicant's entitlement to apply for and be granted (30) Data relating to the priority: a patent (Rule 4.17(u)) for the following designations 10237821.5 19 August 2002 (19.08.2002) DE AE, AG, AL, AM AT, AU, AZ BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DI( DM, DZ (71) Applicant (for all designated States except US): BAYER EC, EE, ES, Fl, GB, GD, GE, GH, GM HR, HU, ID, CROPSCIENCE AKTIENGESELLSCHAFT [DE/DE]; IL, IN, IS, JP, KE, KG, KP, KR, KZ LC, LK LR, LS, Alfred-Nobel-Str. 50, 40789 Monheim (DE). LT, LU, LV, M, MD, MG, MK, MN, MW MX MZ, NI, NO, NZ, OM PG, PH, PL, PT RO, RU, SC, SD, SE, (72) Inventors; and SG, SK, SL, SY, TJ, TM TN, TR, T, 77, UA, UG, UZ, (75) Inventors/Applicants (US only): ISRAELS, Rafel [NL/DE]; VC, VN, YU, ZA, ZM ZW, APP Patent (GH, GM Dechant-Miebach-Weg 16, 40764 Langenfeld (DE). KE, LS, MW, MZ, SD, SL, SZ TZ, UG, ZM ZW), SCHWIEDOP, Ulrich [DE/DE]; Unter'm Dorfgarten 16, Eurasian Patent (AM AZ BY, KG, KZ, MD, RU, TJ 40789 Monheim (DE). SPRINGER, Bernd [DE/DE]; TM), European Patent (AT, BE, BG, CH, CY, CZ, DE, Haferkamp 8, 51061 Cologne (DE). SEIDEL, John [AU/AU]; DK, EE, ES, FL FR, GB, GR, HU, 1E, IT, LU, MC, NL, Waterview, PO Box 42, Walla Walla, New South Wales 2659 PT, RO, SE, 51, SK, TR), QAPI Patent (BF, BJ, CF, (AU). CG, CI, CM GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (74) Joint Representative: BAYER CROPSCIENCE As to the applicant's entitlement to claim the priority of AKTIENGESELLSCHAFT; Kaiser-Wilheim-Allee, 51373 the earlier application (Rule 4.1 7(iii))for all Leverkusen (DE). designations. (81) Designated states (national): AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, Published: DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, - With International Search Report. HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, For an explanation of the two-letter codes and the other MZ, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, abbreviations, reference is made to the explanations SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, ("Guidance Notes on Codes and Abbreviations") at the VC, VN, YU, ZA, ZM, ZW. beginning of each regular edition ofthe PCT Gazette. (54) Titld* PROTECTANT FORMULATIONS As printed (54) Bezeichnung: BEIZMI'ITL-FORM1JIERUNGEN u(57) Abstract: The invention creates to novel protectant formulations which contain at least onC r4 H 3 C--C-O--4CHF-CH-o- C-CH 3 agrochemical active ingredient that is suitable for IK, E3 Eprotecting seeds, triethylene glycol diacetate of 0 0 formula (r) and additives. The invention also relates to a method for producing the novel seed protectant formulations and to their use for protecting seeds. (57) Zusammenfassung: Neue Beizmittel-Formulieruneen, die mindestens elinen zur Beiung von Saagul geigneen arche- WO 2004/021783 - 1 - PCT/EP2003/008632 Protectant formulations The present invention relates to novel seed dressing formulations, to a process for 5 preparing them, and to their use for dressing seed. It has already been disclosed to dress seed using preparations of one or more agrochemical substances, organic solvents, and additives. By this method the active components can be applied effectively to the surface of the seed grains. A 10, disadvantage of the solvent-based dressing formulations however, is that they are not miscible with water. Moreover, they are highly flammable, intensely odoured, and in many cases also environmentally burdensome. Also already described has been the dressing of seed using water-based dressing 15 formulations. In contrast to the corresponding solvent-containing formulations, these preparations represent a smaller burden on the environment. Moreover, they are more odour-neutral and can be diluted or even washed off with water. A disadvantageous feature, however, is that water-based preparations have a relatively poor dressing pattern. Moreover, active substances sensitive to hydrolysis may suffer 20 decomposition fairly easily in water-based formulations. Novel seed dressing formulations have now been found which are composed of * at least one active agrochemical substance suitable for dressing seed, 25 * triethylene glycol diacetate of the formula H3C-C -O CH--CH-0 -CH3 ) 0 O and 30 WO 2004/021783 - 2 - PCT/EP2003/008632 * additives. It has also been found that seed dressing formulations of the invention may be prepared by mixing 5 e at least one active agrochemical substance suitable for dressing seed, * triethylene glycol diacetate of the formula

HC-C-O+CHF-CH

2 -0 -C-CH 3 10 0 0 and * additives 15 homogeneously and optionally grinding the product formed. Finally, it has been found that the seed dressing formulations of the invention may be used to very good effect for dressing seed. 20 Moreover, the invention also provides seed dressed with seed dressing formulations of the invention and the plant propagation material of said seed. It is to be considered extremely surprising that the seed dressing formulations of the 25 invention may be applied completely evenly to seed even following dilution with water beforehand. Another unexpected feature is that, in the presence of sensitive substances, the dressing formulations of the invention exhibit a much better stability than corresponding preparations containing no triethylene glycol diacetate.

WO 2004/021783 - 3 - PCT/EP2003/008632 The seed dressing formulations of the invention are distinguished by a number of advantages. For instance, they are very well miscible with water and exhibit an outstanding dressing pattern. Another favourable feature is that active substances sensitive to hydrolysis can be applied by means of the seed dressing formulations of 5 the invention without any significant decomposition of the active components. Moreover, even readily degradable substances, such as gibberellins, are stable for a relatively long time in the formulations of the invention. Another advantage, finally is that seed has an extremely intensive colouring when treated with seed dressing formulations of the invention comprising colorants. 10 The seed dressing formulations of the invention comprise one or more active agrochemical substances. In the present context, active agrochemical substances are all substances common for 15 the dressing of seed. With preference, mention may be made of fungicides, bactericides, insecticides, acaricides, and nematicides. Examples of fungicides that may be mentioned include the following: 20 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2',6'-dibromo-2-methyl 4'-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N-(4 trifluoromethylbenzyl)-benzamide; (E)-2-methoximino-N-methyl-2-(2-phenoxy phenyl)-acetamide; 8-hydroxyquinoline sulphate; methyl (E)-2-{2-[6-(2-cyanophen oxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate; methyl (E)-methoximino[alpha 25 (o-tolyloxy)-o-tolyl]-acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole, benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromu conazole, bupirimate, buthiobate, 30 WO 2004/021783 - 4 - PCT/EP2003/008632 calcium polysulphide, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram, 5 dichlorophen, diclobutrazole, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolon, edifenphos, epoxyconazole, ethirimol, etridiazole, 10 fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox, fluoxastrobin, 15 guazatine, hexachlorobenzene, hexaconazole, hymexazole, 20 imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione, iprovalicarb, isoprothiolane, kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, 25 mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil, nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, 30 ofurace, oxadixyl, oxamocarb, oxycarboxin, WO 2004/021783 - 5 - PCT/EP2003/008632 pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, pro benazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, prothioconazole, pyrazophos, 5 pyrifenox, pyrimethanil, pyroquilon, quintozene (PCNB), quinoxyfen, spiroxanune, 10 tebuconazole, tecloftalam, technazene, tetraconazole, thiabendazole, thicyofen, thio phanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triaz oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, 15 validamycin A, vinclozolin, zineb, ziram. 20 Examples that may be mentioned of bactericides include: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, oc thilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclofta lam, copper sulphate, and other copper preparations. 25 Examples of insecticides, acaricides, and nematicides that may be mentioned include: abamectin, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin, 30 Bacillus thuringiensis, 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluorome thyl)-lH-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bi- WO 2004/021783 -6 - PCT/EP2003/008632 fenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben, cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, 5 chloretoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, N-[(6-chloro-3 pyridinyl)-methyl]-N'-cyano-N-methyl-ethanimidamide, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, 10 deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos, 15 fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fen oxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazuron, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fono phos, formothion, fosthiazate, fubfenprox, furathiocarb, 20 HCH, heptenophos, hexaflumuron, hexythiazox, imidacloprid, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda cyhalothrin, lufenuron, 25 malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos, methami dophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, monocroto phos, moxidectin, 30 naled, NC 184, nitenpyram, omethoate, oxamyl, oxydemethon M, oxydeprofos, WO 2004/021783 - 7 - PCT/EP2003/008632 parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phos phamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenophos, promecarb, propaphos, propoxur, prothiophos, prothoate, pymetrozine, pyrachlophos, pyrida 5 phenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos, salithion, sebufos, silafluofen, sulfotep, sulprofos, 10 tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorovinphos, thiacloprid, thiafenox, thiamethoxam, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathene, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb, 15 vamidothion, XMC, xylylcarb, zetamethrin. The triethylene glycol diacetate of the formula (I) in the seed dressing formulations of the invention is already known. 20 The seed dressing formulations of the invention further comprise one or more additives. Suitable additives include all customary components which can be used in seed dressing, such as, for example, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins 25 and optionally water as well. Colorants which may be present in the seed dressing formulations of the invention include all colorants customary for such purposes. Use may be made both of pigments, of sparing solubility in water, and of dyes, which are soluble in water. 30 Examples that may be mentioned include the colorants known under the designations rhodamine B, C.I. Pigment Red 112, and C.I. Solvent Red 1.

WO 2004/021783 - 8 - PCT/EP2003/008632 Suitable wetting agents that may be present in the seed dressing formulations of the invention include all substances which promote wetting and are customary in the formulation of active agrochemical substances. With preference it is possible to use alkylnaphthalene-sulphonates, such as diisopropyl- or diisobutyl-naphthalene 5 sulphonates. Suitable dispersants and/or emulsifiers that may be present in the seed dressing formulations of the invention include all nonionic, anionic, and cationic dispersants that are customary in the formulation of active agrochemical substances. With preference, it 10 is possible to use nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers, and their phosphated or sulphated derivatives. Particularly suitable anionic dispersants are ligninsulphonates, polyacrylic salts, and arylsulphonate-formaldehyde 15 condensates. Defoamers that may be present in the seed dressing formulations of the invention include all foam-inhibiting substances which are customary in the formulation of active agrochemical substances. With preference it is possible to use silicone defoamers and 20 magnesium stearate. Preservatives that may be present in the seed dressing formulations of the invention include all substances which can be used for such purposes in agrochemical compositions. By way of example, mention may be made of dichlorophen and benzyl 25 alcohol hemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations of the invention include all substances which can be used for such purposes in agrochemical compositions. Preferred suitability is possessed by cellulose derivatives, acrylic acid -derivatives, xanthan, modified clays, and highly disperse silica. 30 WO 2004/021783 -9 - PCT/EP2003/008632 Suitable adhesives which may be present in the seed dressing formulations of the invention include all customary binders which can be used in seed dressing. With preference, mention may be made of polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose. 5 Suitable gibberellins which may be present in the seed dressing formulations of the invention include preferably substances of the formula 0 HO (II) 10

CH

3 COOH CH 2 in which R stands for a hydrogen atom or a hydroxyl group and 15 the dashed line indicates that in the position of the ring either a C-C single bond or a C=C double bond is present. Examples that may be mentioned of gibberellins of the formula (II) include the following: c=o HO 'OH 20 CH3 COOH CH2 gibberellin AI (I-1) WO 2004/021783 - 10 - PCT/EP2003/008632 c=o HO 'Unnu OH 2 gibberellin

A

3 (= gibberellic acid) (11-2) c=o HO 5 CH3 COOH CH2 gibberellin A 4 (11-3) and c=oI HOI 2 gibberellin

A

7 10 (11-4) Particular preference is given to gibberellic acid of the formula (11-2). The gibberellins of the formula (II) are known (cf. R. Wegler "Chemie der Pflanzen 15 schutz- and Schadlingsmittel", Volume 2, Springer Verlag, Berlin-Heidelberg-New York, 1970, pages 401 - 412). If agrochemical active substances not decomposed by hydrolysis are present in the seed dressing formulations of the invention then the formulations may also include 20 water.

WO 2004/021783 - 11 - PCT/EP2003/008632 In the seed dressing formulations of the invention, the concentrations of the individual components may be varied within a relatively wide range. For instance, the amount 5 e of active agrochemical substances is generally between 0.1 and 50% by weight, preferably between 0.5 and 20% by weight; of triethylene glycol diacetate of the formula (I) is generally between 50 and 95% by weight, preferably between 50 and 90% by weight and 10 * of additives is generally between 1 and 30% by weight, preferably between 5 and 20% by weight. For the implementation of the process of the invention, suitable starting materials 15 include all those components which have already been mentioned in connection with the description of the seed dressing formulations of the invention. For the implementation of the process of the invention, a generally adopted procedure is to mix the components with one another in any order and with stirring. Where the 20 active agrochemical substances or other constituents are solid components, the product formed after mixing can be comminuted by grinding to the particular particle size desired. In general, formulations are prepared in which the average size of the solid particles lies between 0.5 and 40 pm. For comminuting the premixes it is possible to use all any grinding equipment which can normally be used for this 25 purpose. By way of example, mention may be made of bead mills. The temperatures when preparing the seed dressing formulations of the invention may be varied within a relatively wide range. Preparation is generally carried out at temperatures between 10*C and 70*C, preferably between 15'C and 50*C. 30 The seed dressing formulations of the invention may be used directly or after dilution with water beforehand to treat seed of any of a very wide variety of types. For instance, WO 2004/021783 - 12 - PCT/EP2003/008632 the concentrates in accordance with the invention or the preparations obtainable therefrom by dilution with water may be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also the seed of maize, rice, oilseed rape, peas, field beans, cotton, sunflowers, and beets, or else vegetable seed of any of a very 5 wide variety of kinds. The seed dressing formulations of the invention or their dilute preparations may also be used to dress seed of transgenic plants. In this context, synergistic effects may also arise in interaction with the substances formed by expression. 10 Suitable mixing equipment for treating seed with the seed dressing formulations of the invention or the preparations prepared from them by adding water includes all mixing equipment which can commonly be used for dressing. The specific procedure adopted when dressing comprises introducing the seed into a mixer, adding the particular desired amount of seed dressing formulation, either as it is or following dilution with 15 water beforehand, and carrying out mixing until the formulation is uniformly distributed on the seed. Optionally, a drying operation follows. The application rate of the seed dressing formulations of the invention may be varied within a relatively wide range. It is guided by the particular active agrochemical 20 substances, by their amount in the formulations, and by the seed. The preparation and use of the seed dressing formulations of the invention are evident from the following examples.

WO 2004/021783 - 13 - PCT/EP2003/008632 Preparation Examples Example 1 5 A seed dressing formulation is prepared by mixing 2 parts by weight of tebuconazole, 5 parts by weight of a red colorant with the designation Pigment Red 112, 1 part by weight of polyethylene oxide-polypropylene oxide-polyethylene oxide 10 copolymer (dispersant) with the designation Pluronic PE 10 500, and 91 parts by weight of triethylene glycol diacetate at room temperature with intensive stirring. The product obtained is subsequently ground using a bead mill so finely that the average size of the solid particles is 15 ~1 gim. In this way a homogeneous, red-coloured suspension is obtained. Example 2 A seed dressing formulation is prepared by mixing 20 2 parts by weight of tebuconazole, 5 parts by weight of a red colorant with the designation Pigment Red 112, 1 part by weight of polyethylene oxide-polypropylene oxide-polyethylene oxide copolymer (dispersant) with the designation Pluronic PE 10 500, 25 1 part by weight of highly disperse silica (Aerosil 200), and 91 parts by weight of triethylene glycol diacetate at room temperature with intensive stirring. The product obtained is subsequently ground using a bead mill so finely that the average size of the solid particles is 30 ~ 1 pm. In this way a homogeneous, red-coloured suspension possessing an outstanding sedimentation stability is obtained.

WO 2004/021783 - 14 - PCT/EP2003/008632 Example 3 A seed dressing formulation is prepared by mixing 5 2 parts by weight of tebuconazole, 5 parts by weight of a red colorant with the designation Pigment Red 112, 1 part by weight of polyethylene oxide-polypropylene oxide-polyethylene oxide copolymer (dispersant) with the designation Pluronic PE 10 500, 1 part by weight of highly disperse silica (Aerosil 200), 10 1 part by weight of gibberellic acid of the formula (11-2), and 90 parts by weight of triethylene glycol diacetate at room temperature with intensive stirring. The product obtained is subsequently ground using a bead mill so finely that the average size of the solid particles is 15 ~ 1 pm. In this way a homogeneous, red-coloured suspension is obtained. Comparative Examples Example A 20 A seed dressing formulation is prepared by mixing 2 parts by weight of tebuconazole, 5 parts by weight of a red colorant with the designation Pigment Red 112, 25 1 part by weight of polyethylene oxide-polypropylene oxide-polyethylene oxide copolymer (dispersant) with the designation Pluronic PE 10 500 and 91 parts by weight of water at room temperature with intensive stirring. The product obtained is subsequently ground using a bead mill so finely that the average size of the solid particles is 1 pm. In this way a homogeneous, red-coloured suspension is obtained.

WO 2004/021783 - 15 - PCT/EP2003/008632 Example B A seed dressing formulation is prepared by mixing 5 2 parts by weight of tebuconazole, 5 parts by weight of a red colorant with the designation Pigment Red 112, 1 part by weight of polyethylene oxide-polypropylene oxide-polyethylene oxide copolymer (dispersant) with the designation Pluronic PE 10 500, 1 part by weight of highly disperse gibberellic acid of the formula (11-2) and 10 90 parts by weight of water at room temperature with intensive stirring. The product obtained is subsequently ground using a bead mill so finely that the average size of the solid particles is ~ 1 pm. In this way a homogeneous, red-coloured suspension is obtained. Use Examples 15 Example I a) In a laboratory dressing apparatus (Mini rotostat) 2 kg of wheat seed are treated for 20 seconds with 6 ml of a mixture of 20 1 part by weight of seed dressing formulation from Example 1 and 2 parts by weight of water prepared immediately beforehand. 25 b) In a laboratory dressing apparatus (Mini rotostat) 2 kg of wheat seed are treated for 20 seconds with 6 ml of a mixture of 1 part by weight of seed dressing formulation from Example A and 2 parts by weight of water WO 2004/021783 - 16 - PCT/EP2003/008632 prepared immediately beforehand. This gives dressed wheat seed. 5 A comparison of the two dressed seed batches shows the following: The seed treated in accordance with (a) is fully uniformly dressed and coloured an intense red. 10 In contrast, the seed treated in accordance with (b) is not completely uniformly dressed and is less intensively red in coloration. Example II 15 The seed dressing formulations of Example 3 and Example B are stored at a temperature of 54'C for 2 weeks and then assayed for gibberellic acid. In the seed dressing formulation of Example 3 the gibberellic acid content is still 20 1 per cent by weight. In the seed dressing formulation of Example B the gibberellic acid content is now only 0.1 per cent by weight. 25 In respect of decomposition, therefore, the formulation of the invention is significantly more stable than the prior art, comparative formulation.

Claims

1. Seed dressing formulations comprising 5 e at least one active agrochemical substance suitable for dressing seed, e triethylene glycol diacetate of the formula H 3 C-C-O+CH--CH

2 -O--C-CH 3 O 0 10 and * additives. 15 2. Seed dressing formulations according to claim 1, characterized in that fungicides, bactericides, insecticides, acaricides and/or nematicides are present as active agrochemical substances.

3. Seed dressing formulations according to claim 1, characterized in that 20 tebuconazole is present as an active agrochemical substance.

4. Seed dressing formulations according to claim 1, characterized in that imidacloprid is present as an active agrochemical substance. 25

5. Seed dressing formulations according to claim 1, characterized in that triadimenol is present as an active agrochemical substance.

6. Process for preparing seed dressing formulations according to claim 1, characterized in that 30 e at least one active agrochemical substance suitable for dressing seed, WO 2004/021783 - 18 - PCT/EP2003/008632 * triethylene glycol diacetate of the formula H 3 C-C-O+CHF-CH 2 -O1-CH 3 (I) O O1 0 0 5 and e additives 10 are mixed homogeneously and optionally the product formed is ground.

7. Use of seed dressing formulations according to claim 1 for dressing seed.

8. Seed dressed with seed dressing formulations according to claim 1, and the 15 plant propagation material of said seed.