WO2003015512A1 - Wasser-in-öl-polymerdispersion als additiv in wirkstoffhaltigen zusammensetzungen - Google Patents
Wasser-in-öl-polymerdispersion als additiv in wirkstoffhaltigen zusammensetzungen Download PDFInfo
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- WO2003015512A1 WO2003015512A1 PCT/EP2002/008224 EP0208224W WO03015512A1 WO 2003015512 A1 WO2003015512 A1 WO 2003015512A1 EP 0208224 W EP0208224 W EP 0208224W WO 03015512 A1 WO03015512 A1 WO 03015512A1
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- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
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- 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
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- 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
- A01N25/08—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 solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- 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
- A01N25/24—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 ingredients to enhance the sticking of the active ingredients
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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- 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
Definitions
- the present invention relates to a composition, a ner method for producing a composition, a composition obtainable by this ner method, the use of a water-in-oil polymer dispersion, a ner method for controlling an organism, a ner method for regulating the growth of plants and the use thereof the composition.
- DE 199 36 223 AI discloses an active ingredient-containing composition containing a water-in-oil polymer dispersion and at least one active ingredient.
- the active ingredients are added before, during or after the polymerization.
- a reduction in the so-called run-off effect and a reduction in the so-called leaching effect when applying the composition to substrates could be observed through the composition containing active ingredient described in DE 199 36 223 A1.
- a significant increase in the effectiveness of the active ingredient could not be determined by the compositions described in this document.
- a disadvantage of these compositions is that relatively large amounts of both the active ingredient and the water-in-oil polymer dispersion have to be used.
- the invention is based on the object of overcoming the disadvantages inherent in the prior art.
- the object of the invention is to provide a composition with the aid of which the effectiveness of active ingredients can be increased and the use concentration of these active ingredients can thus be reduced.
- Another object of the invention was to improve the availability of active substances to plants.
- the above-mentioned objects are achieved by a composition comprising
- the additive (A) consists of a water in-oil polymer dispersion (AI) a crosslinked polymer in an amount in a range of 10 to 70 wt .-%, preferably in a range of 20 to 50 wt .-% and more preferably in a range of 25 to 35 % By weight, based in each case on the total weight of the additive (A),
- AI water in-oil polymer dispersion
- (A2) a hydrophobic organic liquid in an amount in the range from 20 to 80% by weight, preferably in a range from 25 to 50% by weight and moreover preferably in a range from 30 to 40% by weight, in each case based on the total weight of the additive (A), (A3) one or more water-in-oil emulsifiers in an amount in a range from 0.5 to 10% by weight, preferably in a range from 1 to 8% by weight.
- % By weight and more preferably in a range from 2 to 6% by weight, in each case based on the total weight of the additive (A), (A5), one or more auxiliaries in an amount in a range from 0 to 20% by weight. %, preferably in a range from 0.01 to 10% by weight, based on the total weight of the additive (A), and
- the additive (A6) contains water in such an amount that the sum (AI) to (A6) is 100% by weight.
- the additive (A) in a composition consisting of water and the additive in an amount of 0.5% by weight, based on the total weight of the composition has at least one of the following, as described herein Test methods specific properties on:
- Composition has the additive (A) in a composition consisting of water and the additive in an amount of 1.5 wt .-%, based on the
- Total weight of the composition at least one of the following properties determined according to the test methods described herein: (al) Reduced flow rate of the aqueous mixture by at least
- the active ingredients (B) which differ from the additive (A) are preferably acaricides (AC), algicides (AL), attractants (AT), reppelents (RE)
- BA Bactericides
- FU fungicides
- HB herbicides
- I insecticides
- MO nematicides
- NE rodenticides
- SA savener
- ST sterilants
- SY Synergies
- NI Niricides
- PG growth regulators
- active ingredients is understood to mean all active ingredients known to the person skilled in the art and suitable without tebuconazole, imidacloprid, thiacloprid, trifloxystrobin and iprovalicarb.
- Growth regulators (PG) in the sense of this invention are substances which change the growth of a plant when it is brought into contact with the growth regulator (PG) compared to the growth of the same plant when it is not brought into contact with the growth regulator (PG) becomes.
- the composition contains at least two, preferably different, active ingredients (B) different from the additive (A).
- the composition contains at least three, preferably different, active ingredients (B) different from the additive (A).
- the composition contains at least four, preferably different, active ingredients (B) different from the additive (A).
- Cadusafos Eglinazin-ethyl HB; Edifenphos FU; Emamectin benzoate LN; Endosulfan LN, AC; Endothal AL, PG, HB; ⁇ -endotoxin from Bacillus thuringiensis LN; Enilconazole (see Imazalil); Epocholeon PG; Epoxiconazole FU; 7,8-epoxy-2-methyl-octadecane AT; EPTC HB; Esfenvalerat IN; Esprocarb HB; Et reviewingl PG etaconazole FU; Ethaboxam FU; Ethalfluralin HB; Ethanethiol RO; Ethanol MO ethephon PG; Ethidimuron HB; Ethiozin HB; Ethiofencarb IN; Ethion LN, AC ethoxyfen HB; Ethirimol FU; Ethoate-methyl AC, IN; Ethof
- Potassium sorbate FU Pretilachlor HB; Primisulfuron HB; Probenazole BA, FU; Prochloraz FU; Procyazin HB; Procymidone FU; Prodiamine HB; Profenofos AC, IN; Profluazole HB; Profulalin HB; Promecarb IN; Prometon HB; Prometryn HB; Pronamid HB; Pronumon AT; Propachlor HB; Propamocarb (hydrochloride) FU; Propanil HB; Propham PG, HB; Propaphos IN; Propaquizafop HB; Propargite AC, AT; Propazine HB; Propetamphos AC, LN; Propham HB, PG; Propiconazole FU; Propineb FU; Propionic acid FU, BA; Propoxur IN; Propyl 3-t-butylphenoxyacetate PG; Propyz
- glyphosate trimesium Sulfotep LN, AC; Sulfur FU, AC, RE; Sulfuric acid HB; Sulprofos IN; 2,4,5-T HB; Ta magrowth (TS303) PG; Tarsic acid IN; Tar oils FU, IN, HB; 2,3,6-TBA HB; TCA HB; TCMTB FU; Tebuconazole FU; Tebufenozid IN; Tebufenpyrad AC; Tebupyrimiphos IN; Tebutam HB; Tebuthiuron HB; Tecloftalam BA, FU; Technologies FU, PG; Teflubenzuron IN; Tefluthrin IN; Temephos IN; Tepraloxydim HB; Terbacil HB; Terbucarb HB; Terbuchlor HB; Terbufos NE, IN; Terbumeton HB; Terbuthylazine HB; Terbutryn HB; Terrazole FU; Te
- the active substance (B) is biological
- Bacillus spp. e.g. B. sphaericus LN, B. subtilis FU; B. thuringiensis LN with B. thuringiensis aizawai, B. thuringiensis israelensis, B. thuringiensis kurstaki, B. thuringiensis tenebrionis);
- Pseudomonas spp. Streptomyces griseoviridis FU; Granuloseviren LN or for example Nuclear Polyhedrose Virus IN.
- compositions according to the invention are those which contain at least one of the above-mentioned active ingredients, but not tebuconazole, imidacloprid, thiacloprid, trifloxystrobin and iprovalicarb.
- active ingredients tebuconazole, imidacloprid, thiacloprid, trifloxystrobin and iprovalicarb are contained.
- the active ingredient (B) different from the additive (A) in the composition according to the invention is preferably in an amount in a range from 0.0001 to 10% by weight, preferably in an amount in a range from 0.001 to 5% by weight , each based on the total weight of the composition.
- the crosslinked polymers (AI) contained in the water-in-oil polymer dispersions according to the invention are a class of polymers which are preferably produced by inverse emulsion polymerization. This produces finely divided, crosslinked polymers in a continuous, water-immiscible organic phase with the addition of water-in-oil emulsifiers.
- the crosslinked polymers (AI) are preferably water-swellable polymers.
- the polymer (AI) is preferably based on components
- Amounts by weight (cd) to (cß) is 100% by weight, the sum of the% by weight of the components giving 100% by weight.
- the monoethylenically unsaturated, acid group-containing monomers (cd) can be partially or completely, preferably partially, neutralized.
- the monoethylenically unsaturated, acid-group-containing monomers are preferably neutralized to at least 25 mol%, particularly preferably to at least 50 mol% and moreover preferably to 50-90 mol%.
- Neutralization is preferably carried out before the polymerization. Neutralization can also be carried out using alkali metal hydroxides, alkaline earth metal hydroxides, ammonia and carbonates and bicarbonates. Any other base is also conceivable, 16
- Preferred monoethylenically unsaturated monomers (cd) containing acid groups are acrylic acid, methacrylic acid, ethacrylic acid, chloroacrylic acid, ⁇ -cyanoacrylic acid, ⁇ -methylacrylic acid (crotonic acid), ⁇ -phenylacrylic acid, ⁇ -acryloxypropionic acid, sorbic acid, ⁇ -chlorosorbic acid, T-methylisocrotonic acid, T-methylisocrotonic acid p-Chlorocinnamic acid, ß-stearic acid, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid, maleic acid, fumaric acid, tricarboxyethylene and maleic anhydride, acrylic acid and methacrylic acid being particularly preferred and acrylic acid also being preferred.
- preferred monoethylenically unsaturated, acid group-containing monomers (cd) are furthermore ethylenically unsaturated sulfonic acid monomers or ethylenically unsaturated phosphonic acid monomers.
- Ethylenically unsaturated sulfonic acid monomers are preferably aliphatic or aromatic vinylsulfonic acids or acrylic or methacrylic sulfonic acids.
- aliphatic or aromatic vinylsulfonic acids are vinylsulfonic acid, allylsulfonic acid, 4-vinylbenzylsulfonic acid,
- Acrylic or methacrylic sulfonic acids are sulfoethyl acrylate, sulfoethyl methacrylate, sulfopropyl acrylate, sulfopropyl methacrylate, 2-hydroxy-3-methacryloxypropyl sulfonic acid and 2-acrylamido-2-methylpropanesulfonic acid.
- ethylenically unsaturated phosphonic acid monomers such as vinylphosphonic acid, allylphosphonic acid, vinylbenzylphosphonic acid,
- Acrylamidoalkylphosphonic acids acrylamidoalkyldiphosphonic acids, phosphonomethylated vinylamines and (meth) acrylicphosphonic acid derivatives are preferred.
- At least 20 mol%, particularly preferably at least 50 mol% and moreover preferably at least 75 mol% of the monoethylenically unsaturated, acid group-containing monomers on which the polymer (AI) is based are monomers containing carboxylate groups.
- the ethylenically unsaturated monomers (cd) containing a protonated nitrogen are dimethylaminoethyl (meth) acrylate hydrochloride and
- Dimethylaminoethyl (meth) acrylate hydrosulfate is preferred.
- Preferred ethylenically unsaturated monomers (cd) containing a quaternized nitrogen are trimethylammoniumethyl (meth) acrylate methosulfate, trimethylammoniumethyl (meth) acrylate chloride, dimethylethylammoniumethyl (meth) acrylate ethosulfate, (meth) acrylamidopropyltrimethylammonium chloride id (meth) sulfamethylammonium trimethyl ,
- Acrylamides and methacrylamides are preferred as monoethylenically unsaturated monomers (c ⁇ ) which can be copolymerized with (al).
- Possible acrylamides are alkyl-substituted acrylamides or aminoalkyl-substituted derivatives of acrylamide or methacrylamide, such as N-methylol (meth) acrylamide, vinylamides, such as N-vinylamides, N-vinylformamides, N-vinylacetamides, N-vinyl-N-methylacetamides, N-vinyl- N-methylformamide, vinylpyrrolidone, N, N-dimethylaminoacrylamide, dimethylacrylamide or diethylacrylamide, acrylamidopropyltrimethylammonium chloride and the corresponding methacrylamide derivatives as well as acrylamide and methacrylamide, with acrylamide being preferred.
- N-methylol (meth) acrylamide vinylamides, such as N-vinylamides, N-vinylformamides, N-vinylacetamides, N-vinyl-N-methylacetamides, N-vin
- water-dispersible monomers prefers as monoethylenically unsaturated monomers (o2) copolymerizable with (cd) are water-dispersible monomers prefers.
- Preferred water-dispersible monomers are acrylic acid esters and methacrylic acid esters, such as ethyl acrylate and ethyl methacrylate, butyl acrylate and butyl methacrylate, vinyl acetate, styrene and isobutylene.
- Preferred crosslinkers according to the invention are compounds which have at least two ethylenically unsaturated grappes within one molecule (crosslinker class I), compounds which have at least two functional groups which react with functional grapples of the monomers (al) or (oß) in a condensation reaction can (crosslinker class II), compounds which have at least one ethylenically unsaturated group and at least one functional group which can react with functional groups of the monomers (cd) or (al) (crosslinker class III), or polyvalent metal cations (crosslinker class IV).
- the compounds of crosslinking class I crosslink the polymers through the radical polymerization of the ethylenically unsaturated grapples of the crosslinker molecule with the monoethylenically unsaturated monomers (cd) or (cß), while for the compounds of crosslinking class II and the polyvalent metal cations of crosslinking class IV crosslinking of the polymers is achieved by the condensation reaction of the functional groups (crosslinking class II) or by electrostatic interaction of the polyvalent metal cation (crosslinking class IN) with the functional groups of the monomers (cd) or (oß).
- the polymer is crosslinked both by radical polymerization of the ethylenically unsaturated group and by a condensation reaction between the functional group of the crosslinking agent and the functional groups of the monomers (cd) or (oß).
- Preferred compounds of crosslinking class I are poly (meth) acrylic acid esters, which, for example, by the reaction of a polyol, such as ethylene glycol, propylene glycol, trimethylolpropane, 1,6-hexanediol, glycerol, pentaerythritol, polyethylene glycol or polypropylene glycol, an amino alcohol, a polyalkylene polyamine, such as Diethylene triamine or Triethylenetetraamine, or an alkoxylated polyol with acrylic acid or methacrylic acid can be obtained.
- a polyol such as ethylene glycol, propylene glycol, trimethylolpropane, 1,6-hexanediol, glycerol, pentaerythritol
- polyethylene glycol or polypropylene glycol an amino alcohol
- a polyalkylene polyamine such as Diethylene triamine or Triethylenetetraamine
- Other compounds of crosslinking class I are polyvinyl compounds, poly (meth) allyl compounds, (meth) acrylic acid esters of a monovinyl compound or (meth) acrylic acid esters of a mono (meth) allyl compound, preferably that
- Mono (meth) allyl compounds of a polyol or an amino alcohol preferred.
- the disclosures are hereby introduced as a reference and are therefore considered part of the disclosure.
- alkenyldi (meth) acrylates such as, for example, ethylene glycol di (meth) acrylate, 1,3-propylene glycol di (meth) acrylate, 1,4-butylene glycol di (meth) acrylate, 1,3-
- Pentaerythritol di (meth) acrylate, alkenyldi (meth) acrylamides such as N-methyldi (meth) acrylamide, N, N'-3-methylbutylidenebis (meth) acrylamide, N, N'- (1,2-di-hydroxyethylene) bis ( meth) acrylamide, N, N'-
- Hexamethylene bis (meth) acrylamide or N, N'-methylene bis (meth) acrylamide, polyalkoxydi (meth) acrylates such as, for example, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate,
- Di (meth) acrylate ester of trimethylolpropane preferably ethoxylated trimethylolpropane, preferably oxyalkylated with 1 to 30 mol of alkylene oxide per hydroxyl group, thioethylene glycol di (meth) acrylate, thiopropylene glycol di (meth) acrylate,
- crosslinking agents of crosslinking class I N, N'-methylenebisacrylamide, N, N'-methylenebismethacrylamide and triallylamine are particularly preferred.
- Preferred compounds of crosslinker class II are compounds which have at least two functional groups which can react in a condensation reaction with the functional groups of the monomers (cd) or (oß), preferably with acid groups, of the monomers (cd).
- These functional groups of the compounds of crosslinker class II are preferably alcohol, amine, aldehyde, glycidyl, isocyanate, carbonate or epichloride functions.
- Examples of compounds of crosslinking class II include polyols such as ethylene glycol, polyethylene glycols such as diethylene glycol, triethylene glycol and tetraethylene glycol, propylene glycol, polypropylene glycols such as dipropylene glycol, tripropylene glycol or tetrapropylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol 2,4-pentanediol, 1,6-hexanediol, 2,5-hexanediol, glycerol, polyglycerol, trimethylolpropane, polyoxypropylene, oxyethylene-oxypropylene block copolymers, sorbitan fatty acid esters,
- Polyoxyethylene sorbitan fatty acid esters pentaerythritol, polyvinyl alcohol and sorbitol, amino alcohols such as ethanolamine, diethanolamine, triethanolamine or propanolamine, polyamine compounds such as ethylene diamine, diethylene triaamine, triethylene tetraamine, tetraethylene pentaamine or pentaethylene hexaamine, polyglycidyl ether compounds
- Ethylene glycol diglycidyl ether polyethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol polyglycidyl ether, pentaerytitrite polyglycidyl ether, propylene glycol diglycidyl ether
- Polyisocyanates preferably diisocyanates such as 2,4-toluenediisocyanate and hexamethylene diisocyanate, polyaziridine compounds such as 2,2-bishydroxymethylbutanol-tris [3- (l-aziridinyl) propionate], 1,6-hexamethylene diethylene urea and diphenylmethane-bis-4 , 4'-N, N'-diethylene urea, halogen epoxides such as epichlorohydric and epibromohydrin and ⁇ -methylepichlorohydrin, alkylene carbonates such as 1,3-dioxolan-2-one (ethylene carbonate), 4-methyl-1,3-dioxolane-2- on (propylene carbonate), 4,5-dimethyl-l, 3-dioxolan-2-one, 4,4-dimethyl-l, 3-dioxolan-2-one, 4-ethyl-l, 3-dioxolan-2
- Glycidoxypropyltrimethoxysilane and ⁇ -aminopropyltrimethoxysilane are preferred.
- oxazolidinones such as 2-oxazolidinone, bis- and poly-2-oxazolidinones and diglycol silicates are preferred.
- Preferred compounds of class III are hydroxyl- or amino group-containing esters of (meth) acrylic acid and N-substituted (meth) acrylamides.
- Possible hydroxyl- or amino group-containing esters of acrylic acid and hydroxyl- or amino group-containing esters of methacrylic acid are, for example, 2-hydroxyethyl acrylate, N, N-dimethylaminoethyl acrylate and the analogous derivatives of methacrylic acid in protonated or quaternized form, such as dimethylaminoethyl (meth) acrylate hydrochloride.
- the polyvalent metal cations of crosslinking class IV are preferably derived from mono- or polyvalent cations, the monovalent in particular from alkali metals such as potassium, sodium, lithium, lithium being preferred.
- Preferred divalent cations are derived from zinc, beryllium, alkaline earth metals, such as magnesium, calcium, strontium, magnesium being preferred.
- Other higher-value cations which can be used according to the invention are cations of aluminum, iron, chromium, manganese, titanium, zirconium and other transition metals and double salts of such cations or mixtures of the salts mentioned.
- Aluminum salts and alums and their different hydrates such as, for. B.
- Al 2 (SO 4 ) 3 and its hydrates are particularly preferably used as crosslinkers of crosslinking class LV.
- Preferred embodiments of the water-in-oil polymer dispersion according to the invention are polymer dispersions in which the polymers are crosslinked by crosslinking agents of the following crosslinking classes or by crosslinking agents of the following combinations of crosslinking classes: I, II, III, IV, I II, I III, I IV, I II III, I II IV, I III IN, II ⁇ i IN, II IN or III IN.
- water-in-oil polymer dispersion according to the invention are polymer dispersions in which the polymers are crosslinked by any of the aforementioned crosslinking agents of crosslinking classes I.
- water-soluble crosslinkers are preferred.
- Tetraallyl ammonium chloride and allylnonaethylene glycol acrylate prepared with 9 moles of ethylene oxide per mole of acrylic acid are particularly preferred.
- At least 50 mol%, preferably at least 90 mol% and particularly preferably at least 99.9 mol% of the monomers are water-soluble in the polymer (AI).
- the hydrophobic, organic liquid (A2) can be any hydrophobic, organic liquid used by the person skilled in the art as a continuous phase in inverse emulsion polymerization.
- Preferred hydrophobic, organic liquids (A2) are aromatic and aliphatic linear, branched and cyclic hydrocarbons. These include hydrocarbons or their mixtures, preferably n- and or iso-paraffins, ligroin with a boiling range from 150 to 200 ° C., in particular also distillates from predominantly paraffinic and naphthenic-based petroleum, such as the so-called white oils.
- linear and branched liquid esters of natural and synthetic origin can also be contained as a continuous phase.
- hydrohobic organic liquids (A2) are furthermore those aliphatic dicarboxylic acid esters described in DE 35 24 950 A1, the disclosure of which is hereby introduced as a reference. Mixtures of the abovementioned liquids can also be present as hydrophobic, organic liquid (A2) in the water-in-oil polymer dispersions according to the invention.
- water-in-oil emulsifiers (A3) the compounds used by those skilled in the art as water-in-oil emulsifiers in inverse emulsion polymerization can be present in the water-in-oil polymer dispersion according to the invention.
- Water-in-oil emulsifiers (A3) with HLB values from 1 to 10, preferably from 2 to 8 and moreover preferably from 3 to 5 are preferred (Römpps Chemie Lexikon, 10th edition, see 1764, Franck'sche Stuttgart Publishing House).
- Preferred emulsifiers are e.g. B.
- water-in-oil emulsifiers are polymeric emulsifiers, as described, for example, in DE-C-2 4 12 266, the disclosure of which is hereby introduced as a reference.
- Especially preferred emulsifiers are polymeric emulsifiers with the trade name Hypermer ® (ICL London, England). Mixtures of different water-in-oil emulsifiers can also be present in the water-in-oil polymer dispersion according to the invention as water-in-oil emulsifiers (A3).
- oil-in-water emulsifiers (A4) which can be used by those skilled in the art as inverters or as activators of water-in-oil polymer dispersions
- Ethoxylated fatty alcohols are preferred, particularly preferred ethoxylated fatty alcohols, which are produced from linear and / or branched fatty alcohols with an alkyl chain length of more than 11 carbon atoms.
- ethoxylation products of highly branched alcohols which are accessible by oxosynthesis such as preferably isotridecyl alcohol.
- Particularly preferred as an inverter are ethoxylation products of higher, once branched alcohols, which are obtainable by Guerbet synthesis.
- Mixtures of different oil-in-water emulsifiers can also be present in the water-in-oil polymer dispersion according to the invention as oil-in-water emulsifiers (A4).
- auxiliaries (A5) polymer dispersions can in the inventive water-in-oil known to the person skilled compounds for the complexation for example, be contained formic acid wetting agents spreading antifreeze agents, dyes, and adhesion promoters of foreign ions such as Versenex ® 80, chain regulators.
- composition according to the invention can be poured through a sieve with a mesh width of 150 ⁇ m at 20 ° C. and a pressure of 1 bar without particles> 150 ⁇ m containing the crosslinked polymer remaining on the sieve.
- composition according to the invention can be poured through a sieve with a mesh width of 90 ⁇ m at 20 ° C. and a pressure of 1 bar without particles> 90 ⁇ m containing the crosslinked polymer remaining on the sieve.
- the invention further relates to a process for the preparation of the composition according to the invention, wherein water with the additive in the form of a water-in-oil polymer dispersion (PD) which comprises a hydrophobic organic phase and crosslinked polymers distributed therein
- PD water-in-oil polymer dispersion
- (PD1) a crosslinked polymer in an amount in a range from 10 to 70% by weight, preferably in a range from 20 to 50% by weight and moreover preferably in a range from 25 to 35% by weight, in each case based on the total weight of the additive, (PD2) of a hydrophobic organic liquid in an amount in a range from 20 to 80% by weight, preferably in a range from 25 to 50% by weight and particularly preferably in a range from 30 to 40% by weight
- % each based on the total weight of the additive, (PD3) one or more water-in-oil emulsifiers in an amount in a range from 0.5 to 10% by weight, preferably in a range from 1 to 8% by weight. % and more preferably in a range from 2 to 6% by weight, in each case based on the total weight of the additive,
- PD4 one or more oil-in-water emulsifiers in an amount in a range from 0.5 to 10% by weight, preferably in a range from 1 to 8% by weight and more preferably in a range from 2 to 6% by weight, in each case based on the total weight of the additive,
- PD5 one or more auxiliaries in an amount in a range from 0 to 20% by weight, preferably in a range from 0.01 to 10% by weight.
- the active ingredient other than the water-in-oil polymer dispersion (PD), the crosslinked polymer (PD1), the hydrophobic organic liquid (PD2), the water-in-oil emulsifier (PD3), the oil-in-water Emulsifier (PD4) and the auxiliaries (PD5) preferably correspond to the active ingredients (A) mentioned at the outset in connection with the composition according to the invention, crosslinked polymers (AI), hydrophobic, organic liquids (A2), Water-in-oil emulsifiers (A3), oil-in-water emulsifiers (A4) and auxiliaries (A5).
- Tap water is preferably used as water (C) for the composition according to the invention, while deionized water is preferably used as water (PD6 in the water-in-oil polymer dispersion.
- the water-in-oil polymer dispersion is prepared by the emulsion polymerization processes known to those skilled in the art, preferably by inverse emulsion polymerization.
- the monomers (cd), (ß) and optionally the crosslinking agents (ß) and the auxiliaries (PD5) are preferably dissolved in water (PD6) and this solution is then dissolved in the hydrophobic, organic liquid (PD2 in the presence of one or more water-in Oil emulsifiers (PD3)
- the polymerization is started by adding polymerization initiators or the polymerization initiators before adding the hydrophobic organic liquid (Disperse PD2 in the composition to ensure a uniform distribution of the initiators in the composition.
- Polymerization initiators can be dissolved or dispersed in a solution of monomers according to the invention.
- All radical-decomposing compounds known to those skilled in the art are suitable as initiators. These include in particular peroxides, hydroperoxides, hydrogen peroxide, persulfates, azo compounds and the so-called redox catalysts. The use of water-soluble catalysts is preferred. In some cases it is advantageous to use mixtures of different polymerization initiators. Among these mixtures, those of hydrogen peroxide and sodium or potassium peroxodisulfate are preferred, which can be used in any conceivable quantitative ratio.
- Suitable organic peroxides are preferably acetylacetone peroxide, methyl ethyl ketone peroxide, t-butyl hydroperoxide,
- azo compounds such as 2,2'-azobis- (2-amidinopropane) dihydrochloride, azo-bis-amidinopropane dihydrochloride, 2,2'-azobis (N, N-dimethylene) isobutyramidin- dihydrochloride , 2- (carbamoylazo) isobutyronitrile and 4,4'-azobis (4-cyanovaleric acid).
- the compounds mentioned are used in customary amounts, preferably in a range from 0.01 to 5, preferably from 0.1 to 2 mol%, in each case based on the amount of the monomers to be polymerized.
- the redox catalysts contain as oxidic component at least one of the above-mentioned per compounds and as reducing component preferably ascorbic acid, glucose, sorbose, manose, ammonium or alkali metal hydrogen sulfite, sulfate, thiosulfate, hyposulfite or sulfide, metal salts such as iron (II) ions or silver ions or
- Sodium hydroxymethylsulfoxylate Ascorbic acid or sodium pyrosulfite is preferably used as the reducing component of the redox catalyst. Based on the amount of monomers used in the polymerization, 1 * 10 "5 to 1 mol% of the reducing component of the redox catalyst and 1 * 10 " 5 to 5 mol% of the oxidizing component of the redox catalyst are used. Instead of, or in addition to, the oxidizing component of the redox catalyst, one or more, preferably water-soluble, azo compounds can be used. A redox system consisting of hydrogen peroxide, sodium peroxodisulfate and ascorbic acid is preferably used according to the invention.
- azo compounds according to the invention are preferred as initiators, with azo-bis-amidinopropane dihydrochloride being particularly preferred.
- the polymerization is initiated with the initiators in a temperature range from 30 to 90 ° C.
- the polymerization can be carried out isothermally, adiabatically or as a combination of an isothermal and adiabatic process.
- the polymerization is preferably carried out isothermally.
- the polymerization is started at a certain temperature under reduced pressure, as described, for example, in EP 228 397 B1, the disclosure of which is hereby introduced as a reference.
- the reduced pressure is set so that volatile substances such as water and constituents of the organic phase distill off due to the heat of polymerization and the temperature can be kept almost constant.
- the end of the polymerization is characterized in that no more distillate passes over.
- the polymerization process is started at a certain temperature in the range from 0 to 50 ° C., preferably 0 to 25 ° C.
- the polymerization is carried out at atmospheric pressure without external heat supply until a maximum final temperature of the dispersion, which is dependent on the content of the dispersion of polymerizable substance, is reached by the heat of polymerization.
- the process is preferably first carried out isothermally. At a predetermined time, the apparatus is aerated with inert gas and the polymerization is continued until a certain final temperature.
- the water-in-oil polymer dispersion is cooled.
- the oil-in-water emulsifiers (PD4) are added to the water-in-oil polymer dispersion as activators or inverters.
- the water-in-oil polymer dispersion used in the process according to the invention preferably has polymer particles with a size of less than 10 ⁇ m, preferably less than 2 ⁇ m and moreover preferably less than 1 ⁇ m. Furthermore, it is preferred that the additive in an aqueous mixture consisting of water and 2.75% by weight of the water-in-oil polymer dispersion (PD), based on the total weight of the aqueous mixture, the water-in Oil polymer dispersion (PD) contains 28% by weight of the crosslinked polymer (PDl), based on the total weight of the water-in-oil polymer dispersion (PD), has at least one of the following properties:
- the water-in-oil polymer dispersion (PD), the water and the active ingredient are mixed by simply combining and mixing the individual components.
- the water-in-oil polymer dispersion can be mixed with the water and then the active ingredient can be added.
- the active ingredient is preferably added to the composition according to the invention after the additive has been mixed with the water.
- the water-in-oil polymer dispersion is preferably mixed with water or with water containing an active ingredient by conveying the aqueous phase with the water-in-oil polymer dispersion (PD) against a shear body, preferably a static mixer.
- the aqueous phase with the water-in-oil polymer dispersion (PD) is conveyed onto this shear body at a pressure of greater than 1.1, preferably greater than 1.5 and particularly preferably greater than 2 bar, it also being preferred that the Pressure does not exceed 10 bar.
- the active compounds can be mixed in pure form with the water and the additive.
- the active substances can be mixed with the water and the additive in the form of active substance compositions, keeping the active substance and formulating agents, such as, for example, organic solvents.
- Preferred embodiments of the process according to the invention are those in which at least one of the active ingredients mentioned in connection with the compositions according to the invention, but not tebuconazole, imidacloprid, thiacloprid, trifloxystrobin and iprovalicarb, is used.
- at least one of the active ingredients tebuconazole, imidacloprid, thiacloprid, trifloxystrobin and iprovalicarb, preferably all of the aforementioned active ingredients are used.
- the invention further relates to a composition which can be obtained by the process according to the invention.
- This composition preferably has the same properties as the composition according to the invention described at the beginning.
- the invention further relates to the use of the additive (A) or an additive in the form of the water-in-oil polymer dispersion (PD) in a composition comprising at least one active ingredient different from the additive for (/ 31) increasing the effectiveness of the active ingredient in Comparison to the same
- Preferred embodiments of the use according to the invention are those uses which result from the following letters or letter combinations: ßl, ßl and ßlßß.
- the effectiveness of the active ingredient in combating an organism is preferably understood as Abbott's effectiveness and determined according to the following equation and stated in%:
- the effectiveness in combating an organism is increased if the effectiveness in combating an organism in the presence of the additive is greater than in combating an organism in the absence of the additive.
- the invention further relates to the use of the invention
- W (X) is the effectiveness of the active substance X when the same amount of the active substance X is administered as in the active substance combination in the presence of the additive, and
- active ingredients for the use (ßl) and (ßl) or as active ingredients in the combination of active ingredients for combating an organism preferred are those active ingredients mentioned in connection with the composition according to the invention which are capable of controlling organisms.
- Organisms are preferably harmful plants, in particular harmful herbs and grasses, harmful fungi, pests such as, for example, harmful insects, harmful bacteria, harmful nematodes and harmful viruses.
- the organisms which are controlled with the additive according to the invention are preferably located on or in a substrate.
- Whole plants or parts of plants such as stems, branches, flowers, leaves, whole or divided roots or tubers, seeds, seeds or fruit, smooth or rough surfaces such as walls, car tires or floors, liquid substrates such as water, in particular water, are preferred as substrates. or gaseous substrates such as air.
- the invention further relates to the use of the additive (A) or an additive in the form of the water-in-oil polymer dispersion (PD) in a composition comprising at least one active ingredient different from the additive for ( ⁇ l) increasing the effectiveness of the active ingredient in comparison at the same
- Preferred embodiments of the use according to the invention are those uses which result from the following letters or letter combinations: ⁇ l, ⁇ 2 and ⁇ l ⁇ 2.
- the effectiveness of the active ingredient in regulating the growth of a plant is preferably understood to mean a plant growth quotient.
- the plant growth quotient is defined as follows:
- the invention further relates to the use of the additive according to the invention in a composition comprising an active ingredient combination which has at least two different active ingredients which are different from the additive contains, to increase the effectiveness of at least one combination of two of the active ingredients (X, Y) of the active ingredient combination in the treatment of the growth of a plant in comparison to the effectiveness W (syn), where for W (syn) applies:
- W (X) is the effectiveness of the active substance X when the same amount of the active substance X is administered as in the active substance combination in the presence of the additive, and
- active substances for the uses ( ⁇ l) and ( ⁇ 2) or for use in a combination of active substances for regulating the growth of a plant those active substances mentioned in connection with the composition according to the invention are preferred which are capable of increasing the growth of plants regulate.
- the invention further relates to a method for controlling an organism, the organism being brought into contact with the compositions according to the invention.
- the organism is preferably located on or in a substrate.
- Preferred substrates and organisms are those substrates or organisms which have already been mentioned in connection with the uses ( ⁇ 1) and ( ⁇ 2) according to the invention.
- the invention further relates to a method for regulating the growth of a plant, the plant being brought into contact with the compositions according to the invention.
- compositions according to the invention is preferably carried out by brushing, dipping or spraying, spraying being particularly preferred.
- compositions according to the invention are preferably sprayed on from a spray liquid tank.
- the invention further relates to the use of the compositions according to the invention in agriculture, in forestry, in garden cultivation, in fruit growing, in vector control, in plant cultivation, in plant breeding, in seed, in plant material, in non-agricultural applications, for control or Control of organisms, in the storage or processing of fruits and field loads or vegetable materials.
- compositions according to the invention are particularly preferred to use as seed dressings and for dressing plant materials, preferably roots or tubers.
- a pipette is used to place 1.0 g of the composition at a height of 20 cm in the middle of the plate (8 cm from the side edge) on a plexiglass plate (length 46 cm, width 16 cm).
- the table top is placed at an angle on a table top so that the angle between the flat table top and the plastic top is 20 °. It is tracked which distance the mixture has covered.
- the flow rate is given in cm / sec and results from the following equation: the distance covered by the aqueous phase
- the viscosity of the water-in-oil polymer dispersion was determined using a Haake RV 20 Rotovisco viscometer with an M5 measuring head. 972.5 g of water with a hardness of 20-25 ° dH are placed in a 2 L plastic beaker and then 27.5 g of product are added with a disposable syringe. The mixture is stirred with the Mutifix record stirrer at 3200 revolutions per minute for 5 minutes and left to rest for 10 minutes. The Haake measuring cup is filled with the prepared solution in such a way that the top marking in the cup is covered by the solution. Now the measuring cup is inserted into the Haake viscometer which has been previously calibrated and fitted with the measuring body. The measurement takes place at switch levels 3 and 8. The displayed scale value is multiplied by the corresponding factor for each switch level, as indicated in the table below.
- 10 ⁇ l of the water-in-oil polymer dispersion are pipetted onto a slide and covered with a cover slip.
- the size of the polymer particles is formed under the light microscope as the average of the size of 100 polymer particles.
- compositions were prepared in such a way that firstly for a hectare each defined amount of a water-in-oil polymer dispersion was stirred into 300 liters of water (spray water amount), then the commercial active ingredient products (active ingredient formulations) were stirred in.
- Triticale stock in the growth stage 39 (in which the flag leaf is fully developed) plots with the composition were injected (growth stages of cereals: Novartis Product Information 2000, Novartis Agro GmbH).
- the compositions were prepared in such a way that firstly, for a hectare in each case a defined amount of a water-in-oil polymer dispersion was stirred into 300 liters of water (amount of spray water), and then the commercial growth regulators were stirred in.
- a backpack sprayer with a spray boom of 1.5m working width and 6 universal flat jet nozzles (Lechler 90-02) at a distance of 25 cm was used to apply the spray liquid.
- the plant height in the plots was measured 14 days and 28 days after application, from the ground to the middle of the ear length.
- the effectiveness of the active ingredient in regulating the growth of the plant is indicated by the plant growth quotient.
- the infection of the untreated controls was 16% after 22 days and 81% after 35 days.
- Table 2 shows that the additive (water-in-oil polymer dispersion) increases the effectiveness of the product. The effect is synergistic, since the effect found is greater than that which was to be expected by adding the effects of the individual active ingredient components.
- the table also shows that the additive reduces the decrease in the effectiveness of the product within a time interval of 13 days (35 days - 22 days).
- the infection of the untreated controls was 21%.
- Table 3 shows that the additive (water-in-oil polymer dispersion) increases the effectiveness of the product.
- the effect is synergistic, since the effect found is greater than that which was to be expected by adding the effects of the individual active ingredient components.
- CCC Cycocel
- a composition containing the amounts of the water-in-oil polymer dispersion given in Table 4 and Cycocel in the amounts indicated was sprayed onto triticale.
- the plant length was determined 14 days and 27 days after application. The following values were determined for the plant growth quotient and thus for the effectiveness of the active ingredient chlormequat chloride in the treatment of triticale:
- Table 4 shows that the additive (water-in-oil polymer dispersion) increases the straw-shortening effect of the product.
- Table 4 also shows that the additive reduces the drop in the effectiveness of the active ingredient within a time interval of 13 days (27 days - 14 days).
- a composition containing the amounts of the water-in-oil polymer dispersion given in Table 5 and Moddus in the given amounts was sprayed onto triticale.
- the plant length was determined 14 days and 27 days after application. The following values were determined for the plant growth quotient and thus for the effectiveness of the active ingredient trinexapec in the treatment of triticale:
- Table 5 shows that the additive (water-in-oil polymer dispersion) increases the straw-shortening effect of the product.
- Table 5 also shows that the additive reduces the drop in the effectiveness of the active ingredient within a time interval of 13 days (27 days - 14 days).
- a composition containing the amounts of the water-in-oil polymer dispersion given in Table 6 and Moddus and / or CCC in the given amounts was sprayed onto triticale.
- the plant length was determined 14 days after application. The following values were determined for the plant growth quotient and thus for the effectiveness of the active ingredients trinexapec and / or chlormequat chloride in the treatment of triticale:
- the water-in-oil polymer dispersion is mixed with water in the amounts given in Table 7 below. Tap water without additives serves as a control.
- Table 7 shows that the addition of the additive in the amounts given in Table 7 in an aqueous mixture is the time elapsed until a given amount of the water contained in the aqueous mixture (100% by weight or 95 % By weight) compared to the same amount of pure tap water.
- Example 8
- the water-in-oil polymer dispersion is mixed with water in the amounts given in Table 8 below. Tap water without additives serves as a control.
- Table 8 shows that the addition of the additive in the amounts given in Table 8 in an aqueous mixture reduces the flow rate.
Landscapes
- 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)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02764766A EP1416792A1 (de) | 2001-08-13 | 2002-07-24 | Wasser-in-öl-polymerdispersion als additiv in wirkstoffhaltigen zusammensetzungen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10138382.7 | 2001-08-13 | ||
DE10138382A DE10138382A1 (de) | 2001-08-13 | 2001-08-13 | Mischungen von Pflanzenschutzmitteln mit Wasser-in-Öl Polymerdispersion |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003015512A1 true WO2003015512A1 (de) | 2003-02-27 |
Family
ID=7694436
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/008224 WO2003015512A1 (de) | 2001-08-13 | 2002-07-24 | Wasser-in-öl-polymerdispersion als additiv in wirkstoffhaltigen zusammensetzungen |
Country Status (4)
Country | Link |
---|---|
US (1) | US20030118614A1 (de) |
EP (1) | EP1416792A1 (de) |
DE (1) | DE10138382A1 (de) |
WO (1) | WO2003015512A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015075646A1 (en) * | 2013-11-20 | 2015-05-28 | Adama Celsius B.V., Amsterdam (Nl), Schaffhausen Branch | Ready mix microemulsion formulation |
US10299471B2 (en) | 2015-06-16 | 2019-05-28 | Evonik Degussa Gmbh | Biodegradable super-spreading, organomodified trisiloxane |
WO2020173675A1 (en) * | 2019-02-26 | 2020-09-03 | Syngenta Crop Protection Ag | Formulation |
RU2810142C2 (ru) * | 2019-02-26 | 2023-12-22 | Сингента Кроп Протекшн Аг | Состав |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6696497B2 (en) * | 2000-02-23 | 2004-02-24 | Basf Aktiengesellschaft | Fungicidal mixtures |
DE10351004A1 (de) * | 2003-10-30 | 2005-05-25 | Basf Ag | Nanopartikuläre Wirkstoffformulierungen |
EA026063B1 (ru) | 2005-04-18 | 2017-02-28 | Басф Се | Сополимер, синтезированный из по меньшей мере трех различных моноэтиленненасыщенных мономеров |
GB0917134D0 (en) * | 2009-09-30 | 2009-11-11 | M I Drilling Fluids Uk Ltd | Crosslinking agents for producing gels and polymer beads for oilfield applications |
US9193898B2 (en) * | 2011-06-08 | 2015-11-24 | Nalco Company | Environmentally friendly dispersion system used in the preparation of inverse emulsion polymers |
CN104671928A (zh) * | 2013-11-27 | 2015-06-03 | 北京阿格瑞斯生物技术有限公司 | 一种高效复合型玉米叶面喷施剂及其使用方法 |
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WO2015075646A1 (en) * | 2013-11-20 | 2015-05-28 | Adama Celsius B.V., Amsterdam (Nl), Schaffhausen Branch | Ready mix microemulsion formulation |
US10299471B2 (en) | 2015-06-16 | 2019-05-28 | Evonik Degussa Gmbh | Biodegradable super-spreading, organomodified trisiloxane |
WO2020173675A1 (en) * | 2019-02-26 | 2020-09-03 | Syngenta Crop Protection Ag | Formulation |
RU2810142C2 (ru) * | 2019-02-26 | 2023-12-22 | Сингента Кроп Протекшн Аг | Состав |
Also Published As
Publication number | Publication date |
---|---|
EP1416792A1 (de) | 2004-05-12 |
DE10138382A1 (de) | 2003-02-27 |
US20030118614A1 (en) | 2003-06-26 |
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