EP2378867A2 - Formulations agrochimiques contenant des oxydes de pyrrolidone alkylène - Google Patents

Formulations agrochimiques contenant des oxydes de pyrrolidone alkylène

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Publication number
EP2378867A2
EP2378867A2 EP09765120A EP09765120A EP2378867A2 EP 2378867 A2 EP2378867 A2 EP 2378867A2 EP 09765120 A EP09765120 A EP 09765120A EP 09765120 A EP09765120 A EP 09765120A EP 2378867 A2 EP2378867 A2 EP 2378867A2
Authority
EP
European Patent Office
Prior art keywords
composition
composition according
butoxy
propoxy
pyrrolidone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09765120A
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German (de)
English (en)
Inventor
Christian Sowa
Ulrich Steinbrenner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP09765120A priority Critical patent/EP2378867A2/fr
Publication of EP2378867A2 publication Critical patent/EP2378867A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—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 stabilising the active ingredients
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—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 characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the present invention is a composition comprising pesticide and polyalkylene oxide. Further subject matter are pyrrolidone alkylene oxides and their use in agrochemical formulations. Another object is the use of the composition according to the invention for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants. Furthermore, the subject matter is the use of a composition according to the invention for controlling unwanted insect or mite infestation on plants and / or for controlling phytopathogenic fungi and / or for controlling undesired plant growth, treating seed of crop plants with the composition. Finally, the present invention also relates to seed treated with the composition according to the invention. Combinations of preferred features with other preferred features are encompassed by the present invention.
  • WO 94/22984 discloses a fuel composition comprising hydrocarbons and additives.
  • an additive inter alia, an adduct of 2-pyrrolidone and 20 1, 2-Epoxybutanechen is produced.
  • WO 03/050211 discloses an unleaded fuel comprising a fuel and an additive from the group of pyrrolidone alkylene oxides.
  • WO 88/06585 discloses pyrrolidonyl acrylate block polymers.
  • lactams can be used with polyalkylene oxide groups.
  • WO 88/06405 discloses iodine complexes with an alkylene oxide lactam and its use for disinfecting.
  • GB 930,668 discloses a hydroxyethoxyethoxyethylpyrrolidinone prepared by reaction of ethylene oxide and N- (2-hydroxyethyl) pyrrolidinone.
  • EP 0 785 297 discloses an aqueous acid bath for the electrodeposition of copper coatings containing copper salt, inorganic acid and a lactam alkoxylate (eg ⁇ -butyrolactam hexa ethoxylate).
  • the object of the present invention was to provide a composition comprising pesticide which enables a high pesticide loading while being stable.
  • stable means that the composition and in particular the composition diluted with water does not or only slightly tends to crystallize.
  • Another object was that the abovementioned composition has the low tendency to crystallize for both dissolved and suspended pesticides.
  • the object has been achieved by a composition comprising pesticide and polyalkylene oxide, wherein the polyalkylene oxide a Pyrrolidonalkylenoxid of the formula I.
  • R 1 is ethoxy, propoxy, butoxy and mixtures thereof;
  • R 2 is H and CrC 6 is alkyl; and
  • n has a value of 2 to 20; equivalent.
  • the group corresponds to this an alkoxy polymer formed from n monomer units of the alkoxy group R 1 .
  • R 1 is ethoxy, propoxy, butoxy and mixtures thereof. That is, the alkoxy polymer may be a homopolymer of ethoxy, propoxy or butoxy, or a copolymer composed of at least two different monomer units of ethoxy, propoxy or butoxy.
  • the copolymer may be a random mixed copolymer or a block copolymer, preferably, the copolymer is a block copolymer.
  • block copolymer means that the various monomer units each occur in a block of like monomer units in the polymer, for example, three ethoxy units followed by five propoxy units followed by two butoxy units.
  • alkoxy stands for -CH 2 -CH 2 -O-, "propoxy” for -CH 2 -CH (CHs) -O-, and "butoxy” for -CH 2 -CH (CH 2 CHs) -O
  • alkoxy units are generally known to the person skilled in the art and corresponding alkoxypolymers are obtainable, for example, by alkoxylation from the corresponding alkylene oxides, such as ethylene oxide, propylene oxide and butylene oxide.
  • the index n can be in a certain range of values, for example 2 to 20. This means both integer values, such as 3, 4 or 5, and values between them, as 3.15 can occur. The same applies to the indices m, o, and p.
  • R 1 is preferably butoxy and mixtures of butoxy with ethoxy and / or propoxy, more preferably butoxy and mixtures of butoxy with propoxy.
  • R 2 is H and C 1 -C 6 alkyl, preferably H and methyl, especially H.
  • the index n has a value of 2 to 20, preferably 2 to 16, particularly preferably 3 to 14.
  • the composition according to the invention usually contains at least 10% by weight, preferably at least 20% by weight, particularly preferably at least 30% by weight of pyrrolidone alkylene oxide I.
  • the composition usually contains at most 95% by weight, preferably at most 90% by weight, particularly preferably at most 80% by weight. % Pyrrolidonalalkylene oxide I.
  • the composition of the invention may be anhydrous or comprise an aqueous phase, preferably it is anhydrous.
  • the composition is anhydrous. It usually comprises at most 5% by weight, preferably at most 2% by weight, particularly preferably at most 0.5% by weight and especially at most 0.1% by weight of water.
  • the composition in this embodiment comprises at least 40% by weight, preferably at least 50% by weight, particularly preferably at least 60% by weight of solvent system, based on the composition.
  • the composition preferably comprises 40 to 95% by weight, preferably at least 50 to 90% by weight, particularly preferably at least 60 to 90% by weight, of solvent system, based on the composition.
  • the composition comprises an aqueous phase.
  • the composition comprises at least 5 wt.%, Preferably at least 10 wt.%, Particularly preferably at least 20 wt.% Water, based on the composition.
  • the composition in this embodiment comprises at least 20% by weight, preferably at least 30% by weight, particularly preferably at least 40% by weight of solvent system, based on the composition.
  • pesticide denotes at least one active ingredient selected from the group of fungicides, insecticides, nematicides, herbicides, safeners and / or growth regulators.
  • Preferred pesticides are fungicides, insecticides and herbicides, especially fungicides.
  • mixtures of pesticides of two or more of the above classes may be used.
  • One skilled in the art will be familiar with such pesticides as described, for example, in Pesticide Manual, 14th Ed. (2006), The British Crop Protection Council, London.
  • Suitable insecticides are insecticides of the carbamate class, organophosphates, organochlorine insecticides, phenylpyrazoles, Pyrethroids, neonicotinoids, spinosines, avermectins, milbemycins, juvenile hormone analogs, alkyl halides, organotin compounds, nereistoxin analogs, benzoylureas, diacylhydrazines, METI acaricides, and insecticides such as chloropicrin, pymetrozin, flonicamide, clofentezine, hexythiazox, etoxazole, Diafenthiuron, propargite, tetradifon, chlorfenapyr, DNOC, buprofezin, cyromazine, amitraz, hydramethylnone, acequinocyl, fluacrypyrim, rotenone, or their derivatives.
  • Suitable fungicides are fungicides of the classes dinitroanilines, allylamines, anilinopyrimidines, antibiotics, aromatic hydrocarbons, benzenesulfonamides, benzimidazoles, benzisothiazoles, benzophenones, benzothiadiazoles, benzotriazines, benzylcarbamates, carbamates, carboxamides, carboxylic acid amides, chloronitriles, cyanoacetamide oximes, cyanoimidazoles, cyclopropanecarboxamides, dicarboximides, dihydrodioxazines , Dinitrophenyl crotonates, dithiocarbamates, dithiolanes, ethylphosphonates, ethylaminothiazolecarboxamides, guanidines, hydroxy (2-amino) pyrimidines, hydroxyanilides, imidazoles, imidazolinones,
  • Suitable herbicides are herbicides of the classes of the acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ethers, glycines, imidazolinones, isoxazoles, isoxazolidinones , Nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates
  • the pesticide contains an insecticide, preferably the pesticide is at least one insecticide.
  • the pesticide contains a fungicide, preferably the pesticide consists of at least one fungicide.
  • Preferred fungicides are pyraclostrobin, metconazole and epoxiconazole.
  • the pesticide contains a herbicide, preferably the pesticide consists of at least one herbicide.
  • the pesticide contains a growth regulator, preferably the pesticide consists of at least one growth regulator. In one embodiment, the pesticide at 20 ° C.
  • pyrrolidone-nalkylene oxide is at least 10 g / l, preferably at least 30 g / l and particularly preferably at least 50 g / l soluble in pyrrolidone-nalkylene oxide.
  • the solvent system used here is the particular pyrrolidonalkylene oxide used.
  • At least one pesticide is at least 90% by weight, based on the pesticide, suspended in the solvent system in the form of solid particles. If the composition comprises at least two pesticides, at least one pesticide is at least 90% by weight dissolved in the solvent system. Preferably, the pesticide is at least 95 wt.%, Particularly preferably at least 98 wt.% Suspended in the solvent system.
  • the composition according to the invention usually comprises 0.1 to 70% by weight of pesticide, preferably 1 to 50% by weight, in particular 3 to 30% by weight, based on the composition.
  • the composition according to the invention optionally comprises a surfactant which means at least one surfactant.
  • Surfactants are compounds that reduce the surface tension of water. Examples of surfactants are ionic (anionic or cationic) and nonionic surfactants.
  • the composition comprises at least two surfactants, more preferably it comprises a nonionic surfactant and an anionic surfactant.
  • the quantitative ratio of nonionic to anionic surfactant is usually 1: 5 to 5: 1, preferably 1: 3 to 3: 1.
  • Suitable ionic surfactants are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphthalene (Morwet ® types, Akzo Nobel, USA) and dibutylnaphthalenesulfonic acid (nekal ® types, BASF, Germany), and of fatty acids , Alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formal
  • Preferred ionic surfactants are anionic surfactants.
  • Suitable anionic surfactants are alkali metal and ammonium salts of alkyl sulfates (alkyl radical: C8 to C12), of sulfuric monoesters of ethoxylated alkanols (degree of ethoxylation of from 4 to 30, alkyl radical: C12 to C18) and ethoxylated alkylphenols (degree of ethoxylation of from 3 to 50,
  • phosphate esters of an alkoxylated alcohol radical especially phosphate ester of an ethoxylated C10-16 fatty alcohol having an ethoxylation degree of from 3 to 15.
  • R1 and R2 are H atoms or C4 to C24 alkyl and are not simultaneously H atoms
  • M1 and M2 can be alkali metal ions and / or ammonium ions.
  • R 1 and R 2 preferably denote linear or branched alkyl radicals having 6 to 18 C atoms, in particular having 6, 12 and 16 C atoms or hydrogen, where R 1 and R 2 are not both simultaneously H atoms.
  • M1 and M2 are preferably sodium, potassium or ammonium, with sodium being particularly preferred.
  • Particularly advantageous compounds (I) are those in which M1 and M2 are sodium, R1 is a branched alkyl radical having 12 C atoms and R2 is an H atom or R1.
  • ком ⁇ онентs which have a proportion of 50 to 90% by weight of the monoalkylated product, such as, for example, Dowfax® 2A1 (trademark of the Dow Chemical Company).
  • Preferred anionic surfactants are alkali metal and ammonium salts of alkylarylsulfonic acids (alkyl group: C9 to C18), preferably linear or branched alkylbenzenesulfonic acids, and phosphate esters of an ethoxylated C10-16 fatty alcohol with ethoxylation degree of 3 to 15.
  • Suitable nonionic surfactants are polyoxyethylene octylphenol ethers, alkoxylated alcohols, such as ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters , Lignin-sulphite liquors as well as proteins, denatured proteins, polysaccharides (eg methylcellulose), hydrophobically modified starches, polyvinylalcohol (Mowiol ® types, Clariant), polyalkoxylates, polyvinylamine (Lupamin ® types, BASF SE), polyethylenimine (L
  • a suitable alkoxylated alcohol is preferably a fatty alcohol alkoxylated with ethylene oxide (EO) or propylene oxide (PO), in particular having 8 to 32, especially 9 to 18, carbon atoms in the fatty alcohol radical.
  • the alkoxylated fatty alcohol usually has a degree of ethoxylation of 1 to 30, preferably 2 to 10 and especially 4 to 8 ethylene oxide groups and / or a degree of propoxylation of 1 to 30, preferably 2 to 15, and especially 3 to 10 propylene oxide groups.
  • the block polymer is usually a di- or triblock polymer or its derivative, the polymeric fraction being composed of ethylene oxide and propylene oxide.
  • the average molecular weight is usually at least 1000 g / mol, preferably at least 2000 g / mol.
  • poly (ethylene oxide-block-propylene oxide) alkyl ethers having a molecular weight of at least 2000 g / mol and a Ci-10-Alkyletherech.
  • Preferred nonionic see surfactants are alkylphenol polyglycol, tristyrylphenol ethoxylates, ethoxylated castor oil, preferably each having 10 to 40 ethylene oxide units per molecule.
  • composition according to the invention may comprise further auxiliaries customary for agrochemical formulations, the choice of auxiliaries being based on the specific application form or the active ingredient.
  • auxiliaries are additional solvents, surfactants (such as solubilizers, protective colloids, wetting agents and adhesives), adjuvants, organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, dyes and adhesives (eg for seed treatment).
  • Additional solvents which may be included in the solvent system include organic solvents such as medium to high boiling point mineral oil fractions such as kerosene and diesel oil, coal tar oils and vegetable or animal oils, aliphatic, cyclic and aromatic hydrocarbons, e.g.
  • solvent mixtures can also be used. At least 30% by weight, preferably at most 10% by weight, based in each case on the solvent system, and particularly preferably no additional solvents, are preferably added to the composition according to the invention.
  • surfactants adjuvants, wetting agents, adhesives, dispersants or emulsifiers
  • the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids eg.
  • the emulsion of the invention may comprise high levels of surfactants and surfactant. It may comprise 0.1 to 40% by weight, preferably 1 to 30 and in particular 2 to 20% by weight total amount of surfactants and surfactants, based on the total amount of the composition.
  • adjuvants examples include organically modified polysiloxanes such as BreakThruS 240 ®; Alcohol alkoxylates such as Atplus ® 245 ® Atplus MBA 1303 ®, Plurafac LF and Lutensol ® ON; EO-PO block polymers, eg. B. Pluronic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. B. Lutensol ® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ® RA.
  • organically modified polysiloxanes such as BreakThruS 240 ®
  • Alcohol alkoxylates such as Atplus ® 245 ® Atplus MBA 1303 ®, Plurafac LF and Lutensol ® ON
  • EO-PO block polymers eg. B. Pluronic RPE 2035 ® and Genapol B ®
  • Alcohol ethoxylates e
  • thickeners ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion
  • thickeners are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ®, CP Kelco), Rhodopol ® 23 (Rhodia) or Veegum ® (RT Vanderbilt) or attaclay ® (Engelhard Corp.).
  • Bactericides may be added to stabilize the composition.
  • bactericides are those based on dichlorophen and benzyl alcohol formal (Proxel ®. Fa. ICI or Acetide ® RS from Thor Chemie and Kathon ® MK from. Rohm & Haas), and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acetide ® MBS from Thor Chemie).
  • Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
  • defoamers examples include silicone emulsions (such as, for example, silicone ® SRE, Wacker, Germany or Rhodorsil ®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned are those under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1, Pigment blue 15: 4, Pigment blue 15: 3, Pigment blue 15: 2, Pigment blue 15: 1, Pigment blue 80 , Pigment yellow low 1, Pigment yellow 13, 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 well-known dyes and pigments.
  • adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and CEI luloseether (Tylose ®, Shin-Etsu, Japan).
  • compositions according to the invention are in the form of agrochemical formulations.
  • Suitable agrochemical formulations are water-soluble concentrates (SL, LS), re-dispersible concentrates (DC), emulsifiable concentrates (EC), emulsions (EW, EO, ES, ME), suspensions (SC, OD, FS) or suspoemulsions (SE) in front.
  • the composition is in the form of an emulsifiable concentrate (EC).
  • composition of the invention is usually diluted before use to produce the so-called tank mix. Dilution is made of medium to high boiling point mineral oil fractions such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydr
  • the diluted composition is usually applied by spraying or atomizing.
  • wetting agents, adjuvants, herbicides, bactericides, fungicides can be added immediately before use (tank mix). These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • the pesticide concentration in the tank mix can be varied in larger areas. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the application rates in the application in crop protection, depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • the present invention also relates to the use of a erfindungsgmä call composition for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, wherein the composition of the respective pests whose Habitat or plants to be protected from the particular pest, soil and / or undesirable plants and / or crops and / or their habitat. Furthermore, the invention relates to the use of a composition according to the invention for controlling undesirable insect or mite infestation on plants and / or for controlling phytopathogenic fungi and / or for controlling undesired plant growth, treating crop seeds with the composition.
  • the invention relates to seed which has been treated with a composition according to the invention.
  • the treatment also called dressing
  • the seed preferably contains the composition according to the invention.
  • This composition can be applied to the seed undiluted or, preferably, diluted.
  • the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of pesticide is present in the compositions to be used for the stain.
  • the application can be done before sowing.
  • the treatment of plant propagation material in particular the treatment of seed, are known in the art, and carried out by dusting, coating, pelleting, dipping or impregnation of the plant propagation material, the treatment is preferably carried out by pelleting, coating and dusting, so that z , B. premature germination of the seed is prevented.
  • pesticide amounts of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of propagation material or seed are generally used.
  • the present invention also relates to a process for the preparation of a composition according to the invention wherein a pesticide and a pyrrolidone alkylene oxide I are mixed.
  • Preferred pyrrolidone alkylene oxides I and solvents are as described above.
  • the mixing is carried out by customary mixing methods, such as stirring, shaking, or other energy input.
  • Other auxiliaries which are used for the preparation of agrochemical formulations can be added in conventional amounts. Examples of suitable auxiliaries are as described above.
  • the invention further relates to pyrrolidone alkylene oxides of the formula II,
  • R 3 is propoxy
  • R 4 is H and CrC 6 is alkyl; and m has a value of 2 to 6.
  • the index m is preferably from 3 to 5.
  • R 4 is preferably H and methyl, especially H.
  • the invention further relates to pyrrolidone alkylene oxides of the formula III,
  • R 5 is mixtures of ethoxy and propoxy;
  • R 6 is H and CrC 6 is alkyl; and o has a value of 2 to 12.
  • the index o preferably has a value of 2 to 10, more preferably 3 to 8 and especially 3 to 6.
  • R 4 is preferably H and methyl, especially H.
  • the group corresponds
  • R5 is mixtures of ethoxy and propoxy. That is, the alkoxy polymer is a copolymer composed of ethoxy and propoxy.
  • the copolymer may be a random mixed copolymer or a block copolymer, preferably, the copolymer is a block copolymer.
  • the invention further relates to pyrrolidone alkylene oxides of the formula IV,
  • R 7 is butoxy and mixtures of butoxy with ethoxy and / or propoxy
  • R 8 is H and CrC 6 is alkyl; and p has a value of 2 to 18.
  • the index p is preferably from 2 to 18, more preferably from 2 to 14 and especially from 3 to 12.
  • R 4 is preferably H and methyl, especially H.
  • the group corresponds
  • alkoxy polymer formed from n mono-m + erections of the alkoxy group R 7 .
  • R 7 is butoxy and mixtures of butoxy with ethoxy and / or propoxy. That is, the alkoxy polymer may be a homopolymer of butoxy, or a copolymer composed of butoxy with ethoxy, butoxy with propoxy, or butoxy with ethoxy and with propoxy.
  • the copolymer may be a random mixed copolymer or a block copolymer, preferably the copolymer is a block copolymer, for example a diblock copolymer or a triblock copolymer.
  • the Pyrrolidonalkylenoxide of formula II, III and IV can be prepared by alkoxylation of pyrrolidone.
  • ethylene oxide, propylene oxide and butylene oxide can be used.
  • the alkoxylation can be catalyzed by strong bases, such as alkali metal hydroxides and alkaline earth metal hydroxides, Brönsted acids or Lewis acids, such as AICb, BF3.
  • catalysts such as hydrotalcite or double metal cyanides (DMC) can be used.
  • the alkoxylation is preferably carried out at temperatures of about 90 to 240 0 C, particularly preferably from 110 to 190 0 C.
  • the alkylene oxide or the mixture of different alkylene oxides is fed to pyrrolidone and catalyst under the vapor pressure of the alkylene oxide mixture prevailing at the selected reaction temperature or at a higher pressure.
  • the alkylene oxide can be reacted with an inert gas (for example gases, nitrogen, CO2) can be diluted up to 99.9%.
  • an inert gas for example gases, nitrogen, CO2
  • a further alkylene oxide for example propylene oxide
  • Suitable alkoxylation conditions are also described in Nikolaus Schonfeldt, Grenz inhabitassitule ⁇ thylenoxid adducts,ticianliche Verlagsgesellschaft mbH, Stuttgart 1984.
  • the alkoxylation is carried out in the presence of the catalyst without addition of a solvent.
  • the alkoxylation can also be carried out with the use of a solvent which is inert under the alkoxylation conditions.
  • the alkoxylation is catalyzed by at least one strong base.
  • Suitable strong bases are for. B. alkali metal, alkali metal hydroxides, alkaline earth metal or alkaline earth metal hydroxides.
  • the bases are generally used in an amount of from 0.01 to 1% by weight, based on the amount of the pyrrolidone to be alkoxylated (cf., G. Gee et al., J.Chem.Soc. (1961), p. 1345, B. Wojtech, Makromol Chem 66, (1966), p 180). Acid catalysis of the alkoxylation reaction is also possible.
  • Lewis acids such as AICb, BF 3 , BFs dietherates, BF 3 ⁇ H 3 PO 4 , SbCl 4 ⁇ 2 H 2 O, hydrotalcite (cf. PH Plesch, The Chemistry of Cationic Polymerization, Pergamon Press, New York (1963)).
  • the present invention also relates to the use of the pyrrolidone alkylene oxide of the above-described formula II, II and IV in agrochemical formulations.
  • Agrochemical formulations are known to the person skilled in the art. They usually contain a pesticide and optionally auxiliaries for agrochemical formulations, for example the abovementioned auxiliaries for agrochemical formulations.
  • the pyrrolidone alkylene oxides of the formula II, III and IV, especially III and IV, and especially IV, are particularly suitable as polyalkylene oxide in the composition according to the invention.
  • compositions in the form of emulsion concentrates are stable and do not tend to crystallize.
  • Surfactant 1 Tristyrylphenol ethoxylate with 16 moles of ethylene oxide per mole (commercially available as Soprophor® BSU from Rhodia S.A.).
  • Surfactant 2 Calcium dodecylbenzene sulfonate (commercially available as Calsogen® AR 100
  • Surfactant 3 Dodecylbenzenesulfonic acid, calcium salt (commercially available as Wettol® EM 1 from BASF).
  • Surfactant 4 nonionic surfactant based on ethoxylated castor oil (commercially available as Wettol® EM 31 from BASF).
  • Epoxyconazole Purity: 95.5% by weight Metconazole: Purity 98.8% by weight
  • Pyraclostrobin Purity 99.4% by weight
  • Example 1 B pyrrolidone + 4 butylene oxide
  • Example 1 C pyrrolidone + 5 butylene oxide
  • Example 1 D pyrrolidone + 5 propylene oxide + 1 butylene oxide
  • Example 1 E pyrrolidone + 10 propylene oxide + 1 butylene oxide
  • epoxiconazole 7.5 g of surfactant 1, 7.5 g of surfactant 2, 12.5 g of pyrrolidone alkylene oxide from Examples 1 were weighed out and made up to 100 ml total volume with ethylhexyl lactate. The batch was mixed by stirring at room temperature until a clear, homogeneous solution of epoxiconazole was obtained.
  • a sample of experiments A to F was diluted in each case with CIPAC water D (containing 342 ppm Ca / Mg ions) to a 1 wt.% Emulsion and allowed to stand for six hours at 20 0 C. During this time no crystals of expoxiconazole were formed.
  • metconazole 15.2 g metconazole, 5.0 g surfactant 3 and 5.0 g surfactant 4 were weighed and made up to 100 ml total volume with Pyrroxidonalkylenoxid from Example 1. The batch was mixed by stirring at room temperature until a clear, homogeneous solution of metconazole was obtained.

Abstract

L'invention concerne une composition comportant un pesticide et un oxyde de polyalkylène. L'invention concerne aussi des oxydes de pyrrolidone alkylène et leur utilisation dans des formulations agrochimiques, l'utilisation de ladite composition dans la lutte contre des champignons phytopathogènes et/ou des végétaux indésirables et/ou une attaque d'insectes ou d'acariens indésirables et/ou pour réguler la croissance de végétaux. L'invention porte également sur l'utilisation d'une composition de l'invention destinée à la lutte contre une attaque d'insectes ou d'acariens indésirables sur des végétaux et/ou contre des champignons phytopathogènes et/ou des végétaux indésirables, ladite composition servant au traitement de semences de plantes utiles. Enfin, l'invention concerne une semence traitée avec la composition de l'invention. L'invention comprend des combinaisons de caractéristiques préférées avec d'autres caractéristiques préférées.
EP09765120A 2008-12-19 2009-12-10 Formulations agrochimiques contenant des oxydes de pyrrolidone alkylène Withdrawn EP2378867A2 (fr)

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EP08172394 2008-12-19
PCT/EP2009/066778 WO2010069848A2 (fr) 2008-12-19 2009-12-10 Formulations agrochimiques contenant des oxydes de pyrrolidone alkylène
EP09765120A EP2378867A2 (fr) 2008-12-19 2009-12-10 Formulations agrochimiques contenant des oxydes de pyrrolidone alkylène

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KR (1) KR20110104527A (fr)
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BR (1) BRPI0917770A2 (fr)
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DE102009030412A1 (de) * 2009-06-25 2010-12-30 Clariant International Ltd. Polyalkylenglykol basierende Etherpyrrolidoncarbonsäuren und Konzentrate zur Herstellung synthetischer Kühlschmierstoffe, die diese enthalten
US20180064103A1 (en) * 2015-07-22 2018-03-08 John M. Moyer, IV Surfactants that improve the stability of agrichemical seed treatment formulations and custom blends and reduce their viscosity and dusting off properties

Citations (1)

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US4830851A (en) * 1987-03-03 1989-05-16 Gaf Corporation Polymeric halophors

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GB930668A (en) 1958-08-28 1963-07-10 Rohm & Haas Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams
US3823160A (en) 1971-10-04 1974-07-09 Gaf Corp Preparation of ether adducts of n-vinyl-2-pyrrolidone
US4760152A (en) 1987-03-02 1988-07-26 Gaf Corporation Pyrrolidonyl acrylate block polymers
EP0785297B1 (fr) 1990-03-19 2000-01-05 ATOTECH Deutschland GmbH Bain aqueuse acide pour le dépôt électrolytique d'une couche de cuivre brilliante, sans fissures et son application
US5352251A (en) 1993-03-30 1994-10-04 Shell Oil Company Fuel compositions
US7226489B2 (en) 2001-12-12 2007-06-05 Exxonmobil Research And Engineering Company Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits

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US4830851A (en) * 1987-03-03 1989-05-16 Gaf Corporation Polymeric halophors

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CN102256482A (zh) 2011-11-23
KR20110104527A (ko) 2011-09-22
US8268339B2 (en) 2012-09-18
JP2012512823A (ja) 2012-06-07
WO2010069848A2 (fr) 2010-06-24
WO2010069848A3 (fr) 2011-03-24
IL213252A0 (en) 2011-07-31
US20110251061A1 (en) 2011-10-13

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