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
  • A01N25/02—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
• • 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
  • A01N25/28—Microcapsules or nanocapsules

Definitions

• the present invention encompasses aqueous dispersions comprising a nanoparticulate formulation of crop protection actives in which the nanoparticle core-shell structures have an average particle diameter of 0.05 to 2.0 ⁇ m, and the crop protection agent in the core is X-ray amorphous together with one or more polymers is present and the shell of a stabilizing shell matrix is produced by a method which is characterized in that
• step (b) mixing the solution obtained in step (a) with the core polymer or a solution of the core polymer in a water-miscible organic solvent, which polymer is not or only partially soluble in water or aqueous solutions or water-solvent mixtures, and
• solid nanoparticulate formulations obtainable from the abovementioned dispersions, agrochemical formulations of a solid carrier treated with a dispersion mentioned above, methods for treating seeds, and / or methods for controlling undesired plant growth and / or for controlling undesired insect or mite infestation on plants and / or for controlling phytopathogenic fungi based on the abovementioned dispersions or agrochemical formulations.
• Nanoparticulate crop protection formulations as described e.g. from EP 932339-A have a number of advantages, e.g. the rate of dissolution and the solubility of the nanoparticulate formulations in the agriculturally important solvents relatively high. Also, the application rates of the crop protection agents used in the nanoparticulate formulations can often be reduced.
• aqueous dispersions of nanoparticulate preparations are prepared, it is desirable that these dispersions remain stable even after prolonged storage and that no agglomeration of the particles or growth of the particles (such as, for example, through Ostwald ripening) takes place.
• the nanoparticulate crop protection formulations used in the state of the art if they are dispersed in an aqueous solution and stored for a correspondingly long time, show an improvement in the storage stability of the formulation which is in need of improvement.
• the object of the present invention was therefore to provide agrochemical formulations which have an improved storage stability compared to the prior art.
• aqueous dispersions comprising a nanoparticulate formulation of crop protection active ingredients in which the nanoparticles
• Core-shell structures having a mean particle diameter of 0.05 to 2.0 microns, preferably 0.1-0.9 ⁇ m and, the phytoprotective agent in the core is present in X-ray amorphous together with one or more polymers, wherein the polymer is not or only partially is soluble in water or aqueous solutions or water-solvent mixtures - and the shell of a stabilizing shell matrix is prepared by a process which is characterized in that
• step (b) mixing the solution obtained in step (a) with the core polymer or a solution of the core polymer in a water-miscible organic solvent, and
• the crop protection agent and the core polymer may be dissolved together in a water-miscible organic solvent.
• Suitable solvents for steps a) and b) are organic, water-miscible solvents which are volatile and thermally stable and contain only carbon, hydrogen, oxygen, nitrogen and sulfur. Conveniently, they are miscible under normal conditions to at least 10 wt .-% with water and have a boiling point below 200 ° C, preferably below 100 ° C and / or have less than 10 carbon atoms. Preferred are corresponding alcohols, esters, ketones, ethers and acetals.
• ethanol n-propanol, I- Sopropanol, butyl acetate, ethyl acetate, tetrahydrofuran, acetone, 1, 2-propanediol-1-n-propyl ether or 1, 2-butanediol-1 methyl ether.
• isopropanol isopropanol, tetrahydrofuran and acetone.
• aqueous solution used in step c) comes as a solvent water or mixtures of water with water-miscible excipients such as glycols and glycerol into consideration.
• Preferred solvent is water.
• the solutions in step (c) are mixed by vigorous stirring or shaking in a suitable device, or by injecting the two components into a mixing chamber so that vigorous mixing occurs.
• Mixing chamber processes are known from WO 05/44221 or EP-A 932339.
• the two components are injected with hard jet into the mixing chamber.
• the mixing process can be discontinuous or, preferably, continuous. As a result of the mixing process, precipitation occurs.
• the solvents used can be removed after the mixing step (c). Depending on the boiling point, this may be done by methods known to those skilled in the art such as e.g. Distillation, if appropriate under reduced pressure, or extraction or membrane filtration take place. , Furthermore, the dispersion obtained can be known to those skilled in the drying processes, such. Freeze drying (lyophilization), spray drying or spray granulation.
• the core of the nanoparticles according to the invention can consist of one, two, three or more phases.
• the core of the nanoparticles according to the invention consists of at least three phases, wherein one phase consists of amorphous particles of the crop protection active, and the other phase represents a molecular dispersion of the crop protection active in a polymer matrix, and the third phase comprises a crop protection agent.
• free polymer phase represents.
• the core of the nanoparticles according to the invention consists of at least two phases, wherein one phase consists of amorphous particles of the active ingredient, and the other phase represents a molecular disperse distribution of the active ingredient in a polymer matrix.
• the term "at least two phases” here means that in addition to the two phases mentioned, further phases may be present, which in turn consist of respectively
• the core of the nanoparticles according to the invention consists of at least two phases, wherein one phase consists of amorphous active substance, and the other phase represents a drug-free polymer matrix.
• the core of the nanoparticles according to the invention consists of a molecular disperse distribution of the active ingredient in a polymer matrix.
• the crop protection agent is present in the core X-ray amorphous along with one or more polymers.
• the term with one or more polymers means that
• the polymer matrix, in which the crop protection agent is molecularly dispersed can consist of one, two, three or four polymers; preferably one or two polymers, more preferably a polymer;
• the crop protection agent-free polymer particles may consist of one, two, three or four polymers, preferably one or two polymers, more preferably a polymer, which may be different from or identical to the polymer of the polymer matrix; In a preferred embodiment, the polymer in the crop protection agent-free particles is identical to the polymer in the polymer matrix.
• all polymers which are in a temperature range between 0 and 240 ° C., a pressure range between 1 and 100 bar, a pH range from 0 to 14 or ionic strengths to 10 are suitable as polymeric constituents which are located in the core of the particles of the crop protection active ingredient preparation according to the invention 10 mol / l are not or only partially soluble in water or aqueous solutions or water-solvent mixtures.
• Virial coefficient which makes a statement about the behavior of a polymer in a solvent (mixture), can be determined experimentally, for example by light scattering measurement or determination of the osmotic pressure.
• the dimension of this coefficient is (mol-l) / g 2 .
• One or more polymers can be used.
• the molar masses of the polymers used are in the range from 1000 to 10,000,000 g / mol, preferably in the range 1,000 to 1,000,000 g / mol. In principle, all polymers suitable for the field of application plant protection are suitable.
• Suitable core polymers are polymers based on the following monomers:
• Triethylene glycol divinyl ether triethylene glycol divinyl methyl ether, trimethylolpropane trimethacrylate, trimethylolpropane trivinyl ether, vinyl (2-ethylhexyl) ether, vinyl 4-tert-butyl butyl benzoate, vinyl acetate, vinyl chloride, vinyl dodecyl ether, vinylidene chloride, vinyl isobutyl ether, vinyl isopropyl ether, vinyl propyl ether and vinyl tert-butyl ether.
• polymers includes both homo- and copolymers.
• the skilled person can control the desired water insolubility of the core polymer by choosing suitable monomers and their relative proportions in the polymer.
• the hydrophilic monomers mentioned in the above list have this desired insolubility only in combination with at least one further hydrophobic monomer and therefore can not be used as homopolymer as the core polymer.
• Suitable copolymers are both random and alternating systems, block copolymers or graft copolymers.
• the term copolymers encompasses polymers which are made up of two or more different monomers, or in which the incorporation of at least one monomer into the polymer chain can be implemented in various ways, e.g. in the case of stereo block copolymers.
• Polyvinyl ethers such as e.g. Polybenzyloxyethylene, polyvinyl acetals, polyvinyl esters, e.g. Polyvinyl acetate, polyoxytetramethylene, polycarbonates, polyesters, polysiloxanes, polyurethanes, polyacrylamides, e.g. Poly (N-isopropylacrylamide), polymethacrylamides, polyhydroxybutyrates, acetylated polyvinyl alcohols, polyacrylates, e.g.
• Polyphenoxyethyl acrylate polymethyl acrylate, polyethyl acrylate, polydodecyl acrylate, poly (i-bornyl acrylate), poly (n-butyl acrylate), poly (t-butyl acrylate), polycyclohexyl acrylate, poly (2-ethylhexyl acrylate), polyhydroxypropyl acrylate, polymethacrylates, e.g.
• Polymethyl methacrylate poly (n-amyl methacrylate), poly (n-butyl methacrylate), polyethyl methacrylate, poly (hydroxypropyl methacrylate), polycyclohexyl methacrylate, poly (2-ethylhexyl methacrylate), polylauryl methacrylate, poly (t-butyl methacrylate), polybenzyl methacrylate, poly ( i-bornyl methacrylate), polyglycidyl methacrylate and polystearyl methacrylate, polystyrene, as well as copolymers based on styrene, eg with maleic anhydride, styrene-butadiene copolymers, methylmethacrylate-styrene copolymers, N-vinylpyrrolidone copolymers, polycaprolactones, polycaprolactams, poly (N-vinylcaprolactam), Gutta Per
• Methylcellulose (degree of substitution 3 - 40%), ethylcellulose, butylcellulose, isopropylcellulose, cellulose esters, such as e.g. Cellulose acetate, starches, modified starches such as methyl ether starch, gum arabic, chitin, shellac, as well as copolymers and block copolymers of the monomers of the above-mentioned. Links.
• biodegradable polymers Of particular interest are biodegradable polymers.
• biodegradable polymers is intended to include all polymers which meet the definition of biodegradability given in DIN V 54900, in particular compostable polyesters.
• biodegradability means that the polyesters disintegrate in a reasonable and detectable time.
• the degradation can be carried out hydrolytically and / or oxidatively and be effected for the most part by the action of microorganisms such as bacteria, yeasts, fungi and algae.
• the biodegradability can be e.g. determine that polyesters are mixed with compost and stored for a certain time. According to ASTM D 5338, ASTM D 6400 and DIN V 54900, C02-free air, for example, is allowed to flow through ripened compost during composting and subjected to a defined temperature program.
• biodegradability is defined as the ratio of the net CO 2 release of the sample (after deduction of CO 2 release by the compost without sample) to the maximum CO 2 release of the sample (calculated from the carbon content of the sample) as biodegradability
• Biodegradable polyester usually show after a few days of composting significant degradation phenomena such as fungal growth, crack and hole formation.
• biodegradable polymers are biodegradable polyesters such as polylactide, polyalkylene adipate repthalates and polylactide glycoside. Particularly preferred are biodegradable polyalkylene adipate repthalates, preferably polybutylene adipate terephthalates. Suitable polyalkylene adipate repthalates are e.g. in DE 4 440 858 (and are commercially available, for example Ecoflex® from BASF).
• interfacial or surface active polymeric protective olloids are interfacial or surface active polymeric protective olloids.
• these surface-active or surface-active polymeric protective oligomers may be admixed with low molecular weight amphiphilic compounds which lead to the stabilization of these polymeric protective colloids.
• Suitable low molecular weight amphiphilic compounds are both ionic and nonionic surfactants.
• Suitable ionic surfactants are, for example, alkylarylsulfonates, phenylsulfonates, alkylsulfates, alkylsulfonates, alkyl ether sulfates, alkylaryl ether sulfates, alkylpolyglycol ether phosphates, polyarylphenyl ether phosphates, alkyl sulfosuccinates, olefin sulfonates, paraffin sulfonates, petroleum sulfonates, taurides, sarcosides, fatty acids, alkylnaphthalenesulfonic acids, naphthalenesulfonic acids, lignin sulfonic acids, lignin sulfite waste liquor , including their alkali, alkaline earth, ammonium and amine salts, alkyl phosphates, quaternary ammonium compounds, alkyl phosphates,
• Suitable nonionic surfactants are, for example, alkylphenol alkoxylates, alcohol alkoxylates, fatty amine alkoxylates, polyoxyethylene glycol fatty acid esters, castor oil alkoxylates, fatty acid alkoxylates, fatty acid amide alkoxylates, fatty acid polydiethanolamides, lanolin ethoxylates, fatty acid polyglycol esters, isotridecyl alcohol, fatty acid amides, fatty acid esters, silicone oils, alkyl polyglycosides, glycerol fatty acid esters.
• Suitable surface or surface active polymeric protective olloids are also referred to as protective colloids and may be synthetic polymers as well as biopolymers or modified biopolymers.
• Suitable synthetic protective colloids are polymers based on the following monomers:
• 2-methyl-N-vinylimidazole acrylamide, acrylamidomethylpropanesulfonic acid, acrylonitrile, acrylic acid, aminopropyl vinyl ether, butanediol monoacrylate, butanediol monomethacrylate, butanediol monovinyl ether, butyl acrylate, butyl methacrylate, diethylaminoethyl vinyl ether, diethylene glycol monovinyl ether, dimethylaminoethyl acrylate, dimethylaminoethyl acrylate metochloride, dimethylaminoethyl methacrylate, dimethylaminoethyl methacrylate quaternized with methyl chloride, dimethylaminopropyl methacrylamide, ethyl acrylate , Ethylene glycol monovinyl ether, ethylhexyl acrylate, ethylhexyl methacrylate
• Ionizable monomers may optionally be completely or partially neutralized before, during or after the polymerization.
• polymers includes both homo- and copolymers.
• the person skilled in the art can control the desired amphiphilia of the sheath polymer by selecting suitable monomers and their relative proportions in the polymer.
• the strongly hydrophobic monomers mentioned in the above list have the desired amphiphilia only in combination with at least one further hydrophilic monomer and therefore can not be used as homopolymers as enveloping polymers.
• Suitable copolymers are both random and alternating systems, block copolymers or graft copolymers.
• copolymers encompasses polymers which are made up of two or more different monomers or in which the incorporation of at least one monomer into the polymer chain can be realized in various ways, as is the case, for example, with the stereoblock copolymers
• Particularly preferred polymers are polyethylene glycol, polypropylene glycol, polyethylene glycol-polypropylene glycol block copolymers, polyethylene glycol alkyl ethers, polypropylene glycol alkyl ethers, polyethylene glycol-polypropylene glycol ether block copolymers, polyvinyl alcohol, polyvinylpyrrolidone, polyvinylcaprolactam, polyacrylamidomethylpropylsulfonic acid, polycarboxylates such as e.g.
• polyacrylic acid for example, polyacrylates, maleic anhydride / olefin copolymers (for example Sokalan®CP9, BASF) and copolymers based on the monomers of these polymers, furthermore Polyoxyethylenglyceroltriricinoleat and condensation products of sulfonated naphthalenes or phenols with formaldehyde and optionally urea, the as water-soluble salts such as.
• Sokalan®CP9 for example, polyacrylates, maleic anhydride / olefin copolymers
• copolymers based on the monomers of these polymers furthermore Polyoxyethylenglyceroltriricinoleat and condensation products of sulfonated naphthalenes or phenols with formaldehyde and optionally urea, the as water-soluble salts such as.
• sodium salt such as naphthalenesulfonic acid-formaldehyde condensation products or condensation products of phenolsulphonic acid, formaldehyde and urea are present (for example, compounds such as Wettol®D1, Tamol®NN, Tamol®NH BASF or Mornet®D425 from Witco).
• biopolymers or modified biopolymers suitable as protective colloids are gelatin, pectin, chitosan, starch, modified starch, dextrin, gum arabic, casein, caseinate, methylcellulose, carboxymethylcellulose, hydroxypropylcellulose, and alginates.
• polyvinyl alcohol is used as the component for the shell matrix.
• maleic anhydride is / olefin copolymers (fe. Sokalan ® CP9, BASF) is used as a component for the coating matrix.
• polyvinylpyrrolidone is used as the component for the shell matrix.
• polyoxyethylene glycerol triricinoleate is used as the component for the shell matrix.
• a naphthalenesulfonic fonkondensat (Na salt, eg Wettol ® D2) is used as a component for the coating matrix.
• Sparingly soluble crop protection agents are known to the skilled person from the literature.
• crop protection active ingredient means that at least one crop protection active agent from the group of insecticides, fungicides, herbicides and / or safeners (see Pesticide Manual, 13th Ed. (2003)) is selected here for the present formulation.
• Slightly soluble means that the crop protection agent has a solubility of not more than 500 mg / l in water at room temperature.
• insecticides indicates, but is not limited to, possible crop protection agents:
• Organo (thio) phosphates azinphos-methyl, chloropyrifos, chlorpyrifos-methyl, chlorophenvinphos, diazinon, disulphoton, ethion, fenitrothion, fenthion, isoxathione, malathion, methidathione, methyl-parathion, oxydemeton-methyl, paraoxone, parathion, phenthoate, phosalone, phosmet, phosphamidone, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorophone; A.2.
• Carbamates alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulphane, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, thiodicarb, triazamate;
• A.4. Growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorofluorotron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozides, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, a tetronic acid derivative of formulaF 1 ,
• Nicotine receptor agonists / antagonists clothianidin, dinotefuran, thiacloprid;
• GABA antagonists acetoprole, endosulfan, ethiprole, fipronil, vaniliprole;
• Macrolide insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad;
• METI I acaricides fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad;
• METI II and IM compound acequinocyl, fluacyprim, hydramethylnone;
• Decoupler compounds chlorfenapyr;
• A.1 Inhibitors of oxidative phosphorylation cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
• R 1 is -CH 2 OCH 2 CH 3 or H and R "is CF 2 CF 2 CF 3 or CH 2 CH (CHs) 3 , anthra- nilamide compounds of the formula r 3
• B1 is hydrogen or chlorine
• B2 is bromine or CF3
• RB is CH3 or CH (CH3) 2
• malononitrile compounds as described in JP 2002 284608, WO 02/89579, WO 02/90320, WO 02/90321, WO 04/06677, WO 04/20399, or JP 2004 99597, N-R'-2,2-dihalo-1-R "cyclopropane-carboxamides-2- (2,6-dichloro- ⁇ , ⁇ , ⁇ , ⁇ tri-fluoro-p-tolyl) hydrazones or N-R'-2,2-di (R "') propionamides 2- (2,6-dichloro- ⁇ , ⁇ , ⁇ , ⁇ -trifluoro-p-tolyl ) -hydrazones, wherein R 'is methyl or ethyl, halo is chloro or bromo, R "is hydrogen or methyl and R'" is methyl or
• Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, 2- (ortho ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3 methoxy-methyl acrylate;
• Carboxylic acid amides Carboxylic acid anilides: Benalaxyl, Benodanil, Boscalid, Carboxin, Mepronil, Fenfuram, Fenhexamid, Flutolanil, Furametpyr, Metalaxyl, Ofurace, Oxadixyl, Oxycarboxin, Penthiopyrad, Thifluzamide, Tiadinil, 4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid - (4'-Bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl -2-ethyl-thiazole-5-carboxylic acid (4'-chloro-3'-fluorobiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl
• Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide;
• Triazoles Bitertanol, Bromuconazole, Cyproconazole, Difenoconazole, Diniconazole, Enilconazole, Epoxiconazole, Fenbuconazole, Flusilazole, Fluquinconazole, Flutriafol, Hexaconazole, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Penconazole, Propiconazole, Prothioconazole, Simeconazole, Tebuconazole, Tetraconazole, Triadimenol, Triadimefon , Triticonazole;
• - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
• Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
• Nitrogen-containing heterocyclyl compounds - pyridines: fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine;
• Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
• - piperazines triforins
• - Pyrroles fludioxonil, fenpiclonil
• Dicarboximides iprodione, procymidone, vinclozolin;
• acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, quinoxyfen, tricyclazole, 5-chloro-7- (4-methyl- piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyiminimide, 2-butoxy-6-iodo-3-propyl- chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindole-1-sulfonyl) - [1, 2,4] tazazole-1-sulfonic acid dimethylamide;
• Organometallic compounds fentin salts
• Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
• Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
• Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toluylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene;
• Nitrophenyl derivatives binapacryl, dinocap, dinobuton;
• herbicides The following list of herbicides indicates, but is not limited to:
• ALS inhibitors such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, Pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, imazamethabenz, imazamox, imazapic, imazapyr
• Herbicides such as metflurazon, norflurazon, flufenican, diflufenican, picolinafen, beflubutamide, fluridone, flurochloridone, flurtamone, mesotrione, sulcotrione, isoxachlorotole, isoxaflutole, benzofenap, pyrazolynate, pyrazoxyfen, benzobicyclone, amitrole, cloma- zone, aclonifen, 4- (3 -trifluoromethylphenoxy) - 2- (4-trifluoromethylphenyl) pyrimidine, and 3-heterocyclyl-substituted benzoyl derivatives of the formula (see WO-A-96/26202, WO-A-97/41 116, WO-A-97/411 17 and WO-A-97/41 1 18)
• R 8 , R 10 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -
• R 9 represents a heterocyclic radical selected from the group consisting of thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 4,5 - Dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl and 4,5-dihydroisoxazol-5-yl, wherein said radicals may carry one or more substituents, for example, mono-, di-, tri- or tetrasubstituiert by halogen, Ci-C 4 -alkyl, -C 4 -alkoxy, CrC 4 - haloalkyl, -C
• R 13 hydrogen or C 1 -C 6 -alkyl, if the pH is ⁇ 8.
• Mitosis inhibitors such as Benfluralin, Butraline, Dinitramine, Ethalfluralin, Fluchloralin, i-Sopropalin, Methalpropalin, Nitralin, Oryzalin, Pendimethalin, Prodiamine, Profluralin, Trifluralin, Amiprofos-methyl, Butamifos, Dithiopyr, Thiazopyr, Propyzamide, Chlorthal, Carbetamide, Chlorpropham and propham;
• VLCFA inhibitors such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethyl, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S-metolachlor, pretilachlor, propisochlor, prynachlor, terbuchlor, thenylchlorine, xylachlor, CDEA, Epronaz, Diphenamid, napropamide, naproanilide, pethoxamide, flufenacet, mefenacet, fentrazamide, anilofos, piperophos, cafenstrole, indanofan and tridiphan; Cellulose biosynthesis inhibitors such as dichlobenil, chlorthiamide, isoxaben and flupoxam; Herbicides such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etin
• safener has the following meaning: It is known that in some cases better herbicidal compatibility can be achieved by the combined application of specifically acting herbicides with organic active compounds, which themselves can have a herbicidal action. In these cases, these compounds act as an antidote or antagonist and are referred to as “safeners” due to the fact that they reduce or prevent crop damage.
• a crop protection agent selected from the group of fungicides or insecticides, more preferably from the group consisting of ⁇ -Cypermethrin, Boscalid, Pyraclostrobin, Metconazol, Epoxiconazol and Metaflumizone ne, most preferably from the group consisting of ⁇ -Cypermethrin, Pyraclostrobin and metaflumizone.
• SDS sodium dodecyl sulfate
• the amounts of the various components are selected according to the invention so that the preparations 0.1 to 70 wt .-%, preferably 1 to 40 wt .-%, of active ingredient, 1 to 80 wt .-%, preferably 10 to 60 wt.
• % of one or more amphiphilic polymers shell polymer
• the percentages by weight refer to a dry powder which is obtainable from the abovementioned dispersions.
• the above-mentioned aqueous dispersions may also contain further formulation auxiliaries.
• formulation aid describes surfactants such as wetting agents, adhesives or, anti-foaming agents, thickeners, antifreeze, and bactericides.
• intended formulations may additionally contain adhesives and possibly pigments.
• thickeners ie compounds which impart a pseudoplastic flow behavior to the formulation, ie high viscosity at rest and low viscosity in the agitated state
• thickeners are, for example, polysaccharides or organic layer minerals such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (US Pat. Rhone Poulenc) or Veegum® (RT Vanderbilt) or Attaclay® (Engelhardt).
• Suitable antifoams are, for example, silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, organofluorine compounds and mixtures thereof.
• Bactericides may be added to stabilize the aqueous fungicide formulation.
• Suitable bactericides which may be present in the formulations according to the invention are all bactericides which are customary for the formulation of agrochemical active compounds, for example bactericides based on diclorophene and benzyl alcohol hemiformal. Examples of bactericides are Proxel® from the company ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas.
• Suitable antifreeze agents are e.g. Ethylene glycol, propylene glycol or glycerin.
• surfactants are alkali, alkaline earth, ammonium salts of
• Suitable adhesives which may be present in seed dressing formulations are all customary binders which can be used in pickling agents.
• Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
• dyes to the dispersions according to the invention. All dyes customary for such purposes are suitable here. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 1 12 and Cl.
• Solvent Red 1 known dyes, as well as pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 1 12, pigment red 48: 2, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
• solid crop protection formulations which can be prepared by drying an aqueous dispersion according to the invention by known methods, which optionally, as mentioned above, may contain further Formu réellessangeffen.
• aqueous dispersion according to the invention can also be dried by known methods which do not contain any further formulation auxiliaries. Subsequently, either the solid crop protection formulations corresponding formulation auxiliary can be added.
• processes for the preparation of an agrochemical formulation comprise treating a solid support with a dispersion according to the invention or a solid crop protection formulation according to the invention, and agrochemical formulations obtainable by the abovementioned process.
• the solid crop protection formulation of the invention may be dispersed in a solvent.
• solvents which may be present in the seed dressing formulations according to the invention, all come in agrochemical means usable organic solvents (including the above-mentioned solvent) and water into consideration.
• 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 y-butyrolactone, moreover, strongly polar solvents, such as dimethyl sulfoxide, also aromatic hydrocarbons, such as xylene, also esters, such as propylene glycol monomethyl ether acetate, adipic acid-5 dibutylester, diacetate, heptyl acetate, citric acid tri-n-butyl ester, diethyl phthalate and di-n-butyl phthalate, and further alcohols such as ethanol, n- and i-propanol, n-
• Suitable solid carriers are solid carriers or seeds.
• Suitable solid carriers are e.g. Mineral earths such as silica gels, fumed kaisic acids, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, talc, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide and ground plastics, fertilizers, such as Ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products such as corn meal, tree bark, wood and nutshell meal, cellulose powder and other solid carriers.
• Mineral earths such as silica gels, fumed kaisic acids, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, talc, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide and ground plastics
• fertilizers such as Ammonium sulfate, ammoni
• seed is used as a solid carrier.
• the agrochemical formulation is pickled seed.
• stain includes all seed treatment techniques known to those skilled in the art (e.g., “seed dressing”, “seed coating” and “pelleting”).
• seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms.
• seed preferably describes grains and seeds here.
• Suitable seeds are cereals seed crops, root crops, oilseeds, vegetable seeds, spice seed, ornamental seed, eg durum wheat seed, wheat, barley, oats, rye, maize (forage maize and sweetcorn), soya, oilseed, cruciferous vegetables, cotton, sunflowers, Bananas, Rice, Oilseed Rape, Beets, Beet, Beet, Eggs, Potatoes, Grass, (Ornamental) Lawn, Fodder Grass, Tomatoes, Leek, Pumpkin, Cabbage, Iceberg Lettuce, Pepper, Greens, Melons, Brassica spp, Melons, Beans, Peas, garlic, onions, carrots, tubers such as sugar cane, tabbak, grapes, petunia and geraniums, pansies, balsam, preferably wheat, corn, soy and rice. Seed may also be seed of transgenic or plant obtained by conventional breeding methods.
• seed can be used which is tolerant to herbicides, fungicides or insecticides, e.g. plants resistant to sulfonylureas, imidazolinones or gluconate or glyphosate (see, for example, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, US Pat. No. 5,013,659) or in transgenic plants , eg Cotton producing Bacillus thuringiensis toxin (Bt toxins) and thereby resistant to certain harmful organisms (EP-A-0142924, E P-A-0193259).
• seed of plants can be used, which are used in comparison with conventional plants have modified properties.
• modified starch synthesis for example WO 92/11376, WO 92/14827, WO 91/19806) or fatty acid compositions (WO 91/13972).
• the present invention claims methods for controlling undesired plant growth and / or for controlling undesired insect or mite infestation on plants and / or for controlling phytopathogenic fungi, characterized in that seeds of crop plants are treated as described above with a dispersion or solid crop protection formulation according to the invention ,
• the present invention also relates to methods for controlling undesired plant growth and / or for controlling undesired insect or mite infestation on plants and / or for controlling phytopathogenic fungi, characterized in that the fungi / insects, their habitat or the fungus or insect Insect infestation to be protected plants or soils or the undesirable plants, the soil on which the undesirable plants grow, o- their seeds with a dispersion of the invention or solid crop protection formulation according to the invention or an agrochemical formulation according to the invention, in which a solid carrier is used as a solid carrier , treated.
• phytopathogenic fungi describes but is not limited to the following species: Alternaria spp. on rice, vegetables, soya beans, oilseed rape, sugarbeet and fruits, Aphanomyces spp. on sugar beet and vegetables, Bipolaris and Drechslera spp. Corn, cereals, rice and ornamental grass, Blumeria graminis (powdery mildew) on cereals, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals, grapes, Bremia lactucae on lettuce, Cercospora spp. on corn, soybean, and sugar beet, Cochliobolus spp.
• Millipedes e.g. Blaniulus spp
• Ants for example Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Pogonomyrmex spp and Pheidole megacephala,
• Flies e.g. Agromyza oryzea, Chrysomia bezziana, Chrysomia hominivorax, Chrysomia macellaria, Contarina sorghicola, Cordylobia anthropophaga, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, DeNa antique, DeNa coarctata, DeNa platura, DeNa radicum, Fannia canicularis, Gasterophilus intestinalis, Geomyza tri punctata, Glossina morsitans, Haematobia irritants, Haplodiplosis equestris, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Muscina stabulans, Oestrus ovis, Opo
• Heteroptera e.g. Acrosternum hilare, Blissus leucopterus, Cicadellidae e.g. Empoasca fabae, Chrysomelidae, Cyrtopeltis notatus, Delpahcidae, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Eushistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nephotettix spp, Nezara viridula, Pentatomidae, Piesma quadrata, Solubea insularis and Thyanta perditor,
• Lepidoptera for example Agrotis ypsilon, Agrotis segetum and other Agrotis spp, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Chilo suppresalis and other Chilo spp.
• Orthoptera e.g. Acrididae, Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina Stauronotus maroccanus and Tachycines asynamorus;
• Termites e.g. Calotermes flavicollis, Coptotermes spp, Dalbulus maidis, Leucotermes flavipes, Macrotermes gilvus, Reticulitermes lucifugus, and Termes natalensis;
• Thrips e.g. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici and other Frankliniella spp, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips simplex and Thrips tabaci,
• Arachnids for example eg of the families Argasidae, Ixodidae and Sarcoptidae, eg Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp eg Aculus badendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp eg Phy
• Nematodes especially plant parasitic nematodes e.g. "root-knot” nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other melodiogynous spp; cyst-forming nematodes, Globodera rostochiensis and other Globodera spp; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera spp; Seed gall nematodes, Anguina spp; Star and foliar nematodes, Aphelenchoides spp; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus spp; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus spp
• Controlling undesired plant growth means controlling / destroying plants that grow in places where they are undesirable, e.g. from
• a molecularly disperse solution of 20 g of pyraclostrobin (purity: 96.2%) and 40 g of polymer ([poly (methyl methacrylate / styrene)] in 260 g of THF was fed to a mixing chamber at 25 ° C. There, it was mixed with 3000 g of an aqueous solution of polyvinyl alcohol (87 . -89% hydrolyzed; Mw: 13000-23000) the concentration of polyvinyl alcohol in the aqueous solution was 30 g / L the entire process was carried out under a pressure limit of 40bar After mixing, a colloidally pyraclostrobin was - dispersion obtained with white-turbid hue.. By quasi-elastic Light scattering (Bl 90), the average particle size was determined to be 700 nm. The solids content was 4.24% (Mettler Toledo HR 73 Halogen Moisture Analyzer)
• a molecularly disperse solution of 20 g of pyraclostrobin (purity: 96.2%) and 40 g of polymer (copolymer of 4-vinylpyridine and phenoxyethyl acrylate) in 260 g of THF was fed at 25 ° C to a mixing chamber. There, it was mixed with 3000 g of an aqueous solution of polyvinyl alcohol (87-89% hydrolyzed M w : 13000-23000). The concentration of polyvinyl alcohol in the aqueous solution was 30 g / L. The entire process took place under pressure limitation to 40 bar. After mixing, a colloidally disperse pyraclostrobin dispersion having a white cloudy color was obtained. By quasi-elastic light scattering (Bl 90), the average particle size was determined to be 296 nm. The solids content was 4.07% (Mettler Toledo HR 73 Halogen Moisture Analyzer)

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• 2006
  • 2006-10-17 CN CNA2006800399585A patent/CN101296617A/zh active Pending
  • 2006-10-17 CA CA002625861A patent/CA2625861A1/en not_active Abandoned
  • 2006-10-17 US US12/091,183 patent/US20080227646A1/en not_active Abandoned
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• 2008
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