EP1711055A2 - Preparations pulverulentes - Google Patents

Preparations pulverulentes

Info

Publication number
EP1711055A2
EP1711055A2 EP05706921A EP05706921A EP1711055A2 EP 1711055 A2 EP1711055 A2 EP 1711055A2 EP 05706921 A EP05706921 A EP 05706921A EP 05706921 A EP05706921 A EP 05706921A EP 1711055 A2 EP1711055 A2 EP 1711055A2
Authority
EP
European Patent Office
Prior art keywords
polyurethane
agrochemical active
powder formulation
formulation according
powder
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05706921A
Other languages
German (de)
English (en)
Inventor
Karl Reizlein
Joachim Krüger
Hanns-Peter Müller
Horst Gruttmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1711055A2 publication Critical patent/EP1711055A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Definitions

  • the present invention relates to new powder formulations containing agrochemical active substances and polymers, processes for the preparation of these formulations and their use for the application of agrochemical active substances.
  • Microparticles are already known from WO 99/00013, which contain certain polymers mixed with agrochemical active substances. These preparations are prepared by dissolving polymers and agrochemical active ingredients in an organic solvent that is not very miscible with water, then dispersing this solution in water using emulsifiers, then evaporating the solvent and decanting and / or Filtration separated from the aqueous phase and then dried.
  • a disadvantage of this method is that many and complex measures have to be carried out and the use of relatively large apparatus is required when working on an industrial scale.
  • compositions for the controlled release of agrochemical active substances in an aqueous environment which contain a polymer, in particular a thermoplastic material, and a porosity-inducing agent.
  • WO 03/056921 and WO 03/105584 describe powder formulations which contain biodegradable hydroxyl-containing polyesters or copolymers of styrene and acrylonitrile.
  • At least one agrochemical active ingredient at least one polyurethane and / or polyurethane urea and optionally additives
  • the powder formulations according to the invention can be prepared by adding a mixture of at least one agrochemical active ingredient, at least one polyurethane and / or polyurethane urea and, if appropriate, additives Homogenized in the melt at temperatures between 50 ° C and 200 ° C and the mixture is crushed after cooling so that a powder is obtained in which the particles have a diameter below 125 microns.
  • powder formulations according to the invention are very well suited for the application of the agrochemical active ingredients contained to plants and / or their habitat.
  • powder formulations according to the invention are better suited for the application of the agrochemical active ingredients contained than the constitutionally most similar, known preparations. Above all, it is unexpected that the active components are released in the desired amount over a relatively long period of time.
  • the powder formulations according to the invention contain one or more agrochemical active ingredients.
  • agrochemical active substances are understood to mean all substances customary for plant treatment. Fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, plant nutrients and repellents may be mentioned as preferred. Solid agrochemical agents are preferred.
  • fungicides are:
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, trifloxystrobin, Validamycin A, vinclozolin,
  • bactericides are:
  • insecticides examples include acaricides and nematicides.
  • Bacillus thuringiensis 4-bromo-2- (4-chlorophenyl) -l- (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, Brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproxophon, Flufenproxophon, Flufenproxophon, Flufenproxionfon, Flufenproxophon, Flufenproxionfon, Flufenproxionfon, Flufenproxionfon, Flufenproxionfon, Flufenproxionfon, Fufenproxionproxophon, Fufionproxophon, Fufone Prox, Fufion Prox
  • HCH heptenophos, hexaflumuron, hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
  • Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophhion, Pyrachlophhion, Pyrachlophion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, pyrimidifen, pyriproxifen,
  • herbicides examples are:
  • Anilides such as diflufenican and propanil; Aryl carboxylic acids such as dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as oryzalin
  • Chlorcholine chloride and ethephon are examples of plant growth regulators.
  • plant nutrients are customary inorganic or organic fertilizers for supplying plants with macro and / or micronutrients.
  • repellents are diethyl tolylamide, ethylhexanediol and butopyronoxyl.
  • insecticides which may preferably be contained in the powder formulations according to the invention:
  • herbicides which can preferably be contained in the powder formulations according to the invention:
  • the powder formulations according to the invention contain polyurethane (s) and / or polyurethane urea (s), optionally in a mixture with one or more further polymers.
  • Polyurethanes or polyurethane ureas which can be used for the preparation of the powder formulations according to the invention are reaction products of aliphatic or aromatic diisocyanates with macropolyols, macropolyamines, chain extenders and, if appropriate, chain terminators.
  • Macropolyols and macroamines are taken to mean compounds containing hydroxyl groups and amine groups, such as, for example, polyesters, polycarbonates and polyethers with a molar mass of more than 400 g / mol.
  • Chain extenders are short-chain diols, alkanolamines, water and diamines with a molecular weight below 400 g / mol.
  • Chain terminators are monoalcohols, monoamines and ammonia.
  • the ratio of the isocyanate groups to groups reactive with isocyanate is 1.1: 1 to 1: 2.
  • the starting products can optionally be combined with one another.
  • difunctional compounds are used.
  • proportions of mono- or higher-functional compounds can also be used in such quantities that processing in the melt is possible thermoplastic or in solution.
  • the polyurethanes or polyurethane ureas which can be used for the preparation of the powder formulations according to the invention preferably have a content of urethane groups (NH-CO-O) or urea groups (NH-CO-NH) of 1 to 55% by weight, particularly preferably 1, 5 to 50% by weight.
  • diisocyanates ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane diisocyanate, cyclohexane-1, 3- and -1,4-diisocyanate and any mixtures of these isomers, l -Isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane, 2,4- and 2,6-hexahydrotoluylene diisocyanate and any mixtures of these isomers, hexahydro-1, 3- and / or -1, 4-phenylene diisocyanate , Perhydro-2,4'- and / or -4,4 ' - diphenylmethane diisocyanate and norbornane diisocyanates (eg US-A 3,492,330).
  • TDI tolylene diisocyanate
  • MDI diphenylmethane diisocyanate
  • phenylene diisocyanate phenylene diisocyanate and xylylene diisocyanate.
  • HDI 1,6-hexamethylene diisocyanate
  • IPDI l-isocyanate-3,3,5-trimethyl-5-isocyanatomethylcyclohexane
  • H perhydro-2,4- v and / or -4,4 "-diphenylmethane diisocyanates
  • TDI tolylene diisocyanate
  • MDI diphenylmethane diisocyanate
  • higher-functional isocyanates such as the isocyanurate of HDI (Desmodur® N 3300, Bayer) or the trimere of IPDI (Desmodur® Z 4300, Bayer) can also be used. However, it must be ensured that an average functionality of two is not significantly exceeded. If necessary, reactants with higher Functionality can be compensated for by using other reaction partners with a lower functionality than two.
  • Suitable monofunctional isocyanates are, for example, stearyl isocyanate and cyclohexyl isocyanate.
  • Suitable polyesters are e.g. Reaction products of polyhydric, preferably dihydric and optionally additionally trihydric alcohols with polyhydric, preferably dihydric carboxylic acids or their derivatives capable of esterification.
  • the polycarboxylic acids can be aliphatic, cycloaliphatic, aromatic and / or heterocyclic in nature, e.g. by halogen atoms, substituted and / or unsaturated.
  • polyhydric alcohols are e.g. Ethylene glycol, propylene glycol (l, 2) and - (1,3), butylene glycol (l, 4) and - (2,3), hexanediol (l, 6), octanediol (l, 8), Neopentyl glycol, 1,4-bis (hydroxymethyl) cyclohexane, trimethylolpropane, trimethylolethane, further di-, tri-, tetra- and higher polyethylene glycols, di- and higher polypropylene glycols as well as di- and higher polybutylene glycols in question.
  • the polyesters can have a proportion of terminal carboxyl groups. Lactone polyester, e.g.
  • ⁇ -caprolactone or from hydroxycarboxylic acids, e.g. ⁇ -hydroxycaproic acid can be used.
  • hydroxy-functional polyesters known from fat chemistry such as e.g. Castor oil and its transesterification products are used.
  • Suitable polycarbonates containing hydroxyl groups are those of the type known per se, which e.g. by reacting diols such as propanediol (1,3), butanediol (1,4) and / or hexanediol (1,6), diethylene glycol, triethylene glycol, tetraethylene glycol or thiodiglycol with diaryl carbonates, e.g. Diphenyl carbonate or phosgene can be produced (DE-A 16 94 080, DE-A 22 21 751).
  • diols such as propanediol (1,3), butanediol (1,4) and / or hexanediol (1,6)
  • diethylene glycol triethylene glycol
  • tetraethylene glycol or thiodiglycol e.g. Diphenyl carbonate or phosgene can be produced (DE-A 16 94 080, DE-A 22 21 751).
  • polyester polyols and the polycarbonate diols In addition to the polyester polyols and the polycarbonate diols, mixtures of polyether polyols and polyester polyols and mixtures of polyether polyols and polycarbonate diols can also be used.
  • Suitable polyether diols can be prepared by reacting one or more alkylene oxides with 2 to 4 carbon atoms in the alkylene radical with one starter molecule, the two contains bound active hydrogen atoms.
  • alkylene oxides are: ethylene oxide, 1,2-popylene oxide, epichlorohydrin and 1,2-butylene oxide and 2,3-butylene oxide. Ethylene oxide, propylene oxide and mixtures of 1,2-propylene oxide and ethylene oxide are preferably used.
  • the alkylene oxides can be used individually alternately in succession or as mixtures.
  • starter molecules are: water, amino alcohols such as N-alkyl-diethanolamines, for example N-methyl-diethanol-amine and diols such as ethylene glycol, 1,3 propylene glycol, 1,4-butanediol and 1,6-hexanediol. If appropriate, mixtures of starter molecules can also be used.
  • amino alcohols such as N-alkyl-diethanolamines, for example N-methyl-diethanol-amine
  • diols such as ethylene glycol, 1,3 propylene glycol, 1,4-butanediol and 1,6-hexanediol. If appropriate, mixtures of starter molecules can also be used.
  • Suitable polyether diols are also the hydroxyl-containing polymerization products of tetrahydroturan.
  • Short-chain diols and / or diamines with a molecular weight of 60 to 400 g / mol are used as chain extenders, preferably aliphatic diols with 2 to 14 carbon atoms, such as, for example, ethanediol, 1,6-hexanediol, diethylene glycol, dipropylene glycol and in particular 1,4-butanediol , or (cyclo) aliphatic diamines, such as isophoronediamine, ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, N-methyl-propylene-1,3-diamine, N j N'-dimethyl-ethylenediamine.
  • aliphatic diols with 2 to 14 carbon atoms such as, for example, ethanediol, 1,6-hexanediol, diethylene glycol, dipropylene glycol and in particular 1,4-butanedi
  • Diesters of terephthalic acid with glycols having 2 to 4 carbon atoms and hydroxyalkylene ether of hydroquinone are also suitable. Mixtures of the chain extenders mentioned above can also be used. Smaller amounts of triplets can also be added. 1,2-Propanediol, 1,4-butanediol and 1,6-hexanediol are particularly preferred.
  • alkanolamines examples include 2-aminoethanol and 2-methylaminoethanol.
  • conventional monofunctional compounds can also be used in small amounts, e.g. as a chain terminator or mold release.
  • Examples include alcohols such as ethanol, butanol, octanol and stearyl alcohol or amines such as benzylamine, butylamine and stearylamine.
  • polyurethanes and / or polyurethane ureas should be used which have an average molecular weight of 200 to 50,000 g / mol, preferably of 250 to 20,000 g / mol.
  • the polyurethanes which can be used for the preparation of the powder formulations according to the invention can be prepared by the prepolymer process, the diisocyanate / diisocyanate mixture being first mixed with the polyol / polyol mixture and reacted to give a prepolymer, and then the chain extension, if appropriate, being carried out continuously in solvent.
  • Another possible embodiment is to have one or more isocyanate-reactive compound (s) in a solvent, e.g. Acetone, chloroform or methylene chloride, and the compound containing isocyanate groups, optionally with catalysis, metered.
  • a solvent e.g. Acetone, chloroform or methylene chloride
  • the reaction can be completed by post-heating with stirring.
  • Additives which can be present in the plant treatment compositions according to the invention are all substances which are customarily usable in such polymer preparations. Fillers, lubricants, lubricants and stabilizers known from plastics technology are preferably considered.
  • fillers are: titanium dioxide, barium sulfate, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, and phosphates.
  • lubricants and lubricants are: magnesium stearate. Stearic acid, talc and bentonite.
  • Antioxidants and substances which protect the polymers from undesired degradation during processing are suitable as stabilizing agents.
  • the concentrations of the individual components can be varied within a substantial range in the powder formulations according to the invention.
  • the content of agrochemical active ingredients is generally between 1 and 50% by weight, preferably between 5 and 40% by weight,
  • Polyurethane (s) and / or polyurea (s) generally between 50 and 99% by weight, preferably between 55 and 95% by weight and additives generally between 0 and 30% by weight, preferably between 0 and 20% by weight.
  • the powder formulations can be produced on extruders, kneaders or in stirred vessels.
  • the polyurethanes and / or polyurethane ureas at 50 to 200 ° C with the agrochemical active ingredients mixed.
  • Existing solvent can be removed via an evaporation extruder or from a stirred tank via a distillation bridge.
  • the resulting liquid and homogeneous mixture is transported on cooling belts or cooling rollers using conventional discharge devices. After cooling, the solidified product is removed from the cooling device and broken. The resulting raw granulate is then comminuted and sieved using conventional milling equipment in such a way that a powder is formed in which the particles have a diameter below 125 ⁇ m.
  • Another possible embodiment consists in producing a low-melting, low-molecular, well-crystallizing polyurethane, dissolving in another polyurethane and the agrochemical active ingredient at elevated temperature, and crushing the non-tacky mixture which is solid at room temperature.
  • This version is particularly suitable for active ingredients that decompose at temperatures of 80 to 150 ° C.
  • All mills that are usually used for such purposes can be considered as milling devices.
  • Pin mills, ball mills, jet mills or classifying mills can preferably be used, a mill of the ACM 2 type from Hosokawa Mikropul being mentioned as an example.
  • the powder formulations according to the invention can be used as such or after the addition of further formulation auxiliaries for the application of agrochemical active ingredients in crop protection both in agriculture and forestry and in horticulture.
  • All customary components which can be used in plant treatment compositions are considered as formulation auxiliaries, such as, for example, dyes, wetting agents, dispersing agents, emulsifiers, defoamers, preservatives, components which delay drying, antifreezing agents, secondary thickeners, solvents and, in the case of the manufacture of mordants, also Glue.
  • Suitable dyes which can be used for the further preparation of the powders according to the invention as plant treatment agents are all dyes customary for such purposes. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples which may be mentioned are the dyes known under the names Rhodamine B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1.
  • Suitable wetting agents which can be used for the formulation of the powders according to the invention are all substances which are customary for the formulation of agrochemical active compounds and which promote wetting.
  • Alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
  • Suitable dispersants and / or emulsifiers which can be used to formulate the powders according to the invention are all nonionic, anionic and cationic dispersants customary for formulating active agrochemicals. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used.
  • Suitable nonionic dispersants include, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate formaldehyde condensates.
  • Defoamers which can be used to formulate the powders according to the invention are all foam inhibitors which are customary for formulating active agrochemicals. Silicone defoamers and magnesium stearate can preferably be used.
  • Suitable preservatives which can be used for the formulation of the powders according to the invention are all substances customary for such purposes for the formulation of agrochemical active substances. Examples include dichlorophene and benzyl alcohol hemiform.
  • All components which can be used for such purposes in agrochemical compositions are suitable as components which delay drying and as anti-freeze agents which can be used to formulate the powders according to the invention.
  • Polyhydric alcohols such as glycerol, ethanediol, propanediol and polyethylene glycols of different molecular weights, are preferred.
  • Secondary thickeners which can be used to formulate the powders according to the invention are all substances which can be used in agrochemical compositions for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silica are preferred.
  • Suitable solvents which can be used to formulate the powders according to the invention are all organic solvents which can be used in agrochemical compositions.
  • Ketones such as methyl isobutyl ketone and cyclohexanone, furthermore amides, such as dimethylformamide, furthermore cyclic compounds, such as N-methyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone, N-octyl-caprolactam, N-dodecyl-caprolactam and ⁇ -butyrolactone, in addition strongly polar solvents, such as dimethyl sulfoxide, also aromatic hydrocarbons, such as xylene, also esters, such as propylene glycol monomethyl ether acetate, adipic acid dibutyl ester, acetic acid hexyl ester, acetic acid heptyl ester, citric acid buti-tri-tri Dieth
  • adhesives can also be used to formulate the powders according to the invention.
  • all conventional binders which can be used in pickling agents are suitable.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferred.
  • Dispersions of biodegradable polyester-polyurethane-polyureas in water are also particularly preferred as adhesives. Such dispersions are known (cf. WO 01/17347).
  • the powder formulations according to the invention can be used in practice as such or after mixing with further formulation auxiliaries and / or plant treatment agents and, if appropriate, after further dilution with water.
  • the application is carried out using customary methods, for example by scattering, pouring, spraying or spraying.
  • the powders according to the invention can be converted particularly advantageously by adding appropriate formulation auxiliaries and, if appropriate, diluents into dressing agents with which seeds of the most varied types can be treated.
  • dressings are suitable for dressing the seeds of cereals, such as wheat, barley, rye, oats and triticale, as well as the seeds of rice, corn, rapeseed, peas, field beans, cotton, sunflowers and beets or also vegetable seeds of the most varied of natures.
  • the seed dressing formulations can also be used for dressing seeds of transgenic plants. In cooperation with the substances formed by expression, synergistic effects can also occur.
  • the procedure for dressing is that the seeds are placed in a mixer, the desired amount of dressing formulation is added either as such or after prior dilution with water and mixed until the formulation is evenly distributed on the seed , If necessary, a drying process follows.
  • the powder formulations according to the invention and the formulations which can be prepared therefrom by further mixing with formulation auxiliaries and / or plant treatment agents are outstandingly suitable for applying agrochemical active substances to plants and / or their habitat. They ensure the release of the active components in the desired amount over a longer period of time.
  • the application rate of the powder formulations according to the invention and of the preparations which can be prepared therefrom by further mixing with formulation auxiliaries can be varied within a substantial range. It is based on the agrochemical active substances present, on their content in the plant treatment products, on the respective indication and the field of application.
  • the distillation residue is poured onto a Teflon sheet and pulverized in a brown mix after cooling. After sieving over a mesh size of 63 ⁇ m, 98 g were obtained. According to the grain size determination, 50% of the particles are ⁇ 24 ⁇ m.
  • the active substance content determined by GLC is 20.1%.
  • Samples are taken from the suspension at the times specified below, filtered through a 0.2 ⁇ m microfilter and the active substance content is determined by means of HPLC.
  • Samples are taken from the suspension at the times specified below, filtered through a 0.2 ⁇ m microfilter and the active substance content is determined by means of HPLC.
  • a prepolymer is prepared in a three-necked flask stirring apparatus by introducing 11 1 g of isophorone diisocyanate and introducing 35.4 g of 1,6-hexanediol in portions at 120.degree. The mixture is stirred until the calculated value of 11.48% NCO is reached or is little less. 10.92% NCO was found.
  • 36.6 g of the prepolymer is dissolved in 120 g of methylene chloride and added dropwise to a solution of 10.7 benzylamine and 50 g of methylene chloride with cooling at room temperature. A few minutes after the end of the dropping, the solution is NCO-free according to the IR spectrum. 21.6 g of imidacloprid are introduced. The batch is slowly heated up to 150 ° C while doing so Methylene chloride removed by distillation. Vacuum is applied at 150 ° C up to 15 mbar. The melt is poured onto a Teflon sheet, pulverized in a brown mix and the powder is sieved out to particles ⁇ 125 ⁇ m. 30.0% imidacloprid, determined by HPLC, were found.
  • Samples are taken from the suspension at the times specified below, filtered through a 0.2 ⁇ m microfilter and the active substance content is determined by means of HPLC.
  • Samples are taken from the suspension at the times specified below, filtered through a 0.2 ⁇ m microfilter and the active substance content is determined by means of HPLC.
  • Example 7 Preparation of a powder formulation with a temperature-sensitive active ingredient 30 g of methiocarb, 20 g of polyurethane from Example 5, 85.8 g of the acetone solution from Example 6 and 0.1 g of stearic acid are heated to 110 ° C. in a three-necked flask stirring apparatus the acetone is removed via a distillation bridge first at normal pressure and then up to 15 mbar. The melt is poured onto a Teflon sheet, ground in a brown mix after cooling and sieved to particles ⁇ 125 ⁇ m. The active substance content found via HPLC is 26.5%.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des préparations pulvérulentes qui sont constituées d'au moins une substance active agrochimique, d'au moins un polyuréthanne et/ou d'une urée de polyuréthanne, ainsi que, éventuellement, d'additifs. Ces préparations présentent un diamètre particulaire inférieur à 125 mu m. La présente invention concerne également des procédés pour produire ces préparations et leur utilisation pour l'application de substances actives agrochimiques.
EP05706921A 2004-01-28 2005-01-19 Preparations pulverulentes Withdrawn EP1711055A2 (fr)

Applications Claiming Priority (2)

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DE102004004143A DE102004004143A1 (de) 2004-01-28 2004-01-28 Pulver-Formulierungen
PCT/EP2005/000474 WO2005072525A2 (fr) 2004-01-28 2005-01-19 Preparations pulverulentes

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EP1711055A2 true EP1711055A2 (fr) 2006-10-18

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US (1) US20080069892A1 (fr)
EP (1) EP1711055A2 (fr)
JP (1) JP2007519658A (fr)
KR (1) KR20070000486A (fr)
CN (1) CN1913776A (fr)
AU (1) AU2005207871A1 (fr)
BR (1) BRPI0507144A (fr)
CA (1) CA2554529A1 (fr)
DE (1) DE102004004143A1 (fr)
RU (1) RU2006130690A (fr)
WO (1) WO2005072525A2 (fr)

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DE102007028923A1 (de) * 2007-06-22 2008-12-24 Lanxess Deutschland Gmbh Biozodwirkstoff haltige partikuläre Polymere
DE102008032779A1 (de) * 2008-07-11 2010-01-14 Bayer Materialscience Ag Polyurethanharnstoff-Lösungen
DE102008050415A1 (de) 2008-10-04 2010-04-08 Bayer Technology Services Gmbh Freisetzungs-System zur kontrollierbaren Freisetzung einer Substanz
US20210400975A1 (en) 2020-06-26 2021-12-30 Lonza Solutions Ag Methods and Compositions for Use in Glued-Wood Products

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DE3039882A1 (de) * 1980-10-22 1982-05-27 Bayer Ag, 5090 Leverkusen Ektoparasitizidhaltige polyurethane
JPS63238007A (ja) * 1987-03-25 1988-10-04 Showa Electric Wire & Cable Co Ltd 防蟻剤
DE3903247A1 (de) * 1989-02-03 1990-08-09 Shell Int Research Fungizid wirkende zusammensetzung, verfahren zu ihrer herstellung und ihre verwendung, insbesondere zur heilenden behandlung von an pilzerkrankungen leidenden pflanzen
JPH0680505A (ja) * 1991-09-18 1994-03-22 Shinto Paint Co Ltd 害虫駆除剤及び害虫駆除方法
US20050054537A1 (en) * 2002-01-10 2005-03-10 Hanns-Peter Muller Powder formulations

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BRPI0507144A (pt) 2007-06-26
US20080069892A1 (en) 2008-03-20
CA2554529A1 (fr) 2005-08-11
WO2005072525A2 (fr) 2005-08-11
WO2005072525A3 (fr) 2005-10-06
JP2007519658A (ja) 2007-07-19
RU2006130690A (ru) 2008-03-10
CN1913776A (zh) 2007-02-14
DE102004004143A1 (de) 2005-08-18
AU2005207871A1 (en) 2005-08-11
KR20070000486A (ko) 2007-01-02

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