WO2011069931A1 - Formulation of light-sensitive pesticides and comb polymers containing a uv absorber - Google Patents

Formulation of light-sensitive pesticides and comb polymers containing a uv absorber

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Publication number
WO2011069931A1
WO2011069931A1 PCT/EP2010/068909 EP2010068909W WO2011069931A1 WO 2011069931 A1 WO2011069931 A1 WO 2011069931A1 EP 2010068909 W EP2010068909 W EP 2010068909W WO 2011069931 A1 WO2011069931 A1 WO 2011069931A1
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WO
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Patent type
Prior art keywords
monomer
uv
uv absorber
composition according
peg
Prior art date
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PCT/EP2010/068909
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German (de)
French (fr)
Inventor
Richard Riggs
Oliver Labisch
Arocha Paola Uribe
Michael Ishaque
Christian Bittner
Original Assignee
Basf Se
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, 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
    • A01N25/22Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/34Esters containing nitrogen
    • C08F220/36Esters containing nitrogen containing oxygen in addition to the carboxy oxygen

Abstract

The invention relates to a compound containing a pesticide and a polymeric UV absorber comprising, as monomeric units, a) a UV absorber containing an ethylenically unsaturated group (UV monomer), and b) a polyalkylene oxide containing an ethylenically unsaturated group (PEG monomer). The invention further relates to a method for producing said polymeric UV absorber, wherein the UV monomer and the PEG monomer are radically polymerized, and to a compound containing a pesticide and said polymeric UV absorber. Finally, the invention also relates to a method for combating phytopathogenic fungi and/or undesirable plant growth and/or undesirable insect or mite infestation and/or for regulating the growth of plants, wherein said compound is allowed to act on the respective pests, the habitat thereof or the plants to be protected from the respective pest, the ground and/or undesirable plants and/or the useful plants and/or the habitat thereof.

Description

Formulation of light-sensitive pesticides and UV absorbers containing comb polymers

The present invention relates to a composition comprising a pesticide and a polymeric UV absorber comprising, as monomer units a), a UV absorber comprising an ethylenically unsaturated group (UV-monomer), and b) a polyalkylene oxide containing an ethylenically unsaturated group (PEG monomer). Furthermore, the invention relates to a process for the preparation of said polymeric UV absorber, wherein the UV-monomer and the PEG-monomer are radically polymerized, and a composition comprising a pesticide and the abovementioned polymeric UV absorber. Finally, it relates to a method for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, where ge the aforementioned composition on the respective pests, their habitat, or the from the particular pest to be protected plants, the soil and / or on undesired plants and / or the crop plants and / or leaves their habitat. Combinations of preferred features with other preferred features are encompassed by the present invention. Various polymeric UV-absorbers are known:

WO 89/03386 discloses UV absorbing copolymers composed of UV absorbers with ethylenically unsaturated groups, and various comonomers. The copolymers own for the production of contact lenses.

EP 0123368 discloses polymers comprising an olefinic p-aminobenzoate, N-vinylpyrrolidone, and (meth) acrylic acid. The polymers own for the production of sunscreen. US 3,992,356 discloses polymers for cosmetic applications comprising in the chain makromoleklaren an acrylic ester-containing ultraviolet absorber, and optional comonomer mers, such as vinyl stearate or stearyl (meth) acrylate.

EP 0896006 discloses polymeric UV absorber based on acrylic ester-containing UV absorbers, Alkylvinyethern and optionally alkyl acrylates.

WO08134674 discloses UV absorbers for ophthalmic lenses.

Agrochemical formulations comprising a pesticide and a UV absorber are also known: WO 2008/085682 discloses a composition comprising photo labile pesticide and a UV protection agent, for example, Uvinul® P25 (PEG-25 para-aminobenzoic acid) can be. EP 0,376,888 A1 discloses compositions for controlling harmful insects containing a harmful changing the behavior of the substance and a pesticidally active compound contained in a flowable matrix both, that protects the behavior-modifying substance from UV radiation. The compositions and UV absorbers from the prior art have various disadvantages: UV-sensitive pesticides were not sufficiently stabilized; high amounts of surfactants had the agrochemical formulation can be added to achieve a high stability of drug dispersions; the surface activity of UV absorber was low, they were poorly soluble or poorly comparable träglich in agrochemical formulations. Object was therefore to find a UV absorber which overcomes the disadvantages of the prior art.

The object was achieved by a composition comprising a pesticide and a polymeric UV absorbers comprising as monomeric units

a) a UV absorber comprising an ethylenically unsaturated group (UV-monomer), and

b) a polyalkylene oxide containing an ethylenically unsaturated group (PEG monomer). UV absorber comprising an ethylenically unsaturated group (referred to hereinafter as UV monomer) are generally known. Examples of UV-monomers, the compounds represented b in EP 0896006, the formula I in unit (wherein the ethylenically unsaturated group there in the form of the polymerized, ie saturated mold is shown), which are hereby incorporated by reference. Further examples of UV-monomers are disclosed in US 5,620,838, formula (I) compounds represented, which are hereby incorporated by reference. UV-monomers containing a benzotriazol-groups are preferred. In a further preferred embodiment, the UV-monomers are the in Figure 1A, 1 B and 1 C compounds represented 1 to 27. More preferably, the UV absorber 2 in Fig. 1A (2- (2'-hydroxy-5'- methacryl- oxyethylphenyl) -2H-benzotriazole). Mixtures of different UV monomers may be included in the polymeric UV absorber.

Polyalkylene oxides containing one ethylenically unsaturated group (hereinafter also called PEG-monomer) are generally known. The PEG monomer preferably contains at least three alkylene oxide groups, more preferably it contains five to 50 alkylene oxide groups. Suitable alkylene oxide groups are for example ethylene oxide, propylene oxide, butylene oxide, preferably ethylene oxide. Examples of ethylenically unsaturated groups are vinyl, acrylate or Methacrlyat groups.

Very particularly preferred PEG monomers are those of formula A

wherein R1 = H or CH 3, R2 = H or Ci-Ci 2 -alkyl, R 3 = H or Ci-Ci 2 -alkyl, R4 = H or Ci-Ci2-alkyl, and n = 3 - 50. R1 is preferably CH 3. R 2 is preferably CH 3. R3 is preferably H or CH3, especially H. R4 is preferably H or CH3, especially H. n is preferably 5 - 35, especially 7 - 30 PEG-monomers, in particular those of formula A, may be obtained by known methods, for example, from WHERE

2006/024538 or WO 2008/068213. Mixtures of various PEG monomers may be included in the polymeric UV absorber

The polymeric UV absorbers, at least one further monomer unit c) th contained, which are usually polymerierbar with the UV-monomers and the PEG-monomer. These include in particular monoethylenically unsaturated monomers (monomers C). Examples for this are:

C1 monoethylenically unsaturated mono- and dicarboxylic acids having 3 to 8 carbon atoms such as acrylic acid, methacrylic acid, crotonic acid, isocrotonic acid, maleic acid, fumaric acid and itaconic acid,

C2 alkyl esters of monoethylenically unsaturated mono- and di-C3-Cs-carboxylic acids, in particular acrylic acid and methacrylic acid with Ci-Cio-alkanols or C3-Cio-cycloalkanols such as methyl acrylate, ethyl acrylate, n-propyl, iso- propyl, n-butyl acrylate, iso-butyl acrylate, tert-butyl acrylate, n-hexyl acrylate, 2-

Ethylhexyl acrylate, cyclohexyl acrylate and the corresponding methacrylic esters,

C3 hydroxyalkyl esters of monoethylenically unsaturated mono- and di-Cs-Cs-carboxylic acids, in particular acrylic acid and methacrylic acid such as 2-hydroxyethyl acrylate, 3-hydroxypropyl, 4-hydroxybutyl, 2-Hydroxyethylmeth- acrylate, 3-hydroxypropyl methacrylate and 4-hydroxybutyl methacrylate,

C4 monoethylenically unsaturated nitriles such as acrylonitrile,

C5 vinyl aromatic monomers such as styrene and vinyltoluenes,

C6 monoethylenically unsaturated sulfonic acids and re phosphonic acids and their salts, in particular alkali metal salts thereof such as vinylsulfonic acid, allyl sulfonic acid, methallylsulfonic acid, styrenesulfonic acid, 2-Acryloxyethansulfonsäure, 2-acrylamido-2-methylpropanesulfonic acid, vinylphosphonic acid, allylphosphonic acid, 2- Acryloxyethanphosphonsäure, 2-acrylamido 2-methylpropanephosphonic acid, and C7 amino group-bearing monomers and their protonation and their square ternierungsprodukte such as [2- (N, N-dimethylamino) ethyl] acrylate, [2- (N, N-dimethylamino) ethyl] methacrylate, [3 - (N, N-dimethylamino) propyl] acrylate [2- (N, N-dimethylamino) propyl] methacrylate, [2- acrylate (N, N, N-trimethyl ammonium) ethyl], [2- (N, N, N-trimethyl ammonium) ethyl] methacrylate, [3- (N, N, N-trimethyl ammonium) propyl] acrylate [2- (N, N, N-trimethyl ammonium) propyl] methacrylate in the form of their chlorides, sulfates, and methosulfates.

Preferred monomeric unit c) are the monomers of group C1, in particular methacrylic acid and acrylic acid, especially methacrylic acid.

The molar ratio of monomer to UV-PEG monomer is usually in the range of 1: 9 to 9: 1, preferably in the range of 1: 5 to 5: 1, and in particular in the range from 1: 2 to 2: 1.

The molar ratio of monomeric unit (c) particularly of (meth) acrylic acid) to UV-monomer is usually in the range of 1: 9 to 9: 1, preferably in the range of 1: 5 to 5: 1, and in particular in the range of 1: 2 to 2: 1. The polymeric UV absorber has usually a proportion of UV monomer to all monomeric units of from 5 to 70 mol%, preferably from 10 to 60 mol%. In a further preferred embodiment, the UV-monomer has a content of all monomer units of 20 to 70 mol%, preferably 30 to 70 mol%, and especially 40 to 60 mol%.

In addition, it can be advantageous for increasing the molecular weight of the polymeric UV absorbers, the copolymerization in the presence of low levels of multi-ethylenically unsaturated monomers with z. perform, 2, 3 or 4 polymerizable double bonds (crosslinking). Examples include diesters and triesters ter ethylenically unsaturated carboxylic acids, in particular the bis- and trisacrylates of diols or polyols with 3 or more OH groups, z. As the bis-acrylates and bis meth-acrylates of ethylene glycol, diethylene glycol, triethylene glycol, neopentyl glycol or polyethylene glycols. Such crosslinkers are, if desired, used in an amount of related generally from 0.01 to 5 wt .-% on the total amount of the monomers to be polymerized. are preferably less than 0.01 wt .-% and in particular no crosslinker used.

The copolymerization of monomers having UV-PEG monomer and optionally further monomers is usually carried out in the presence of free radical encryption bonds, so-called initiators. Such compounds are usually present in amounts up to 30 wt .-%, preferably 0.05 to 15 wt .-% used, in particular 0.2 to 8 wt .-%, based on the monomers to be polymerized. In consisting of several components ren initiators (initiator systems z. B. in redox initiator systems), the above weight based on the sum of the components. Suitable initiators are, for example, organic peroxides and hydroperoxides, also peroxodisulfates, percarbonates, peroxyesters, hydrogen peroxide and azo compounds. Examples of initiators are hydrogen peroxide, dicyclohexyl peroxydicarbonate, diacetyl peroxide, di-tert-butyl peroxide, Diamylperoxid, dioctanoyl peroxide, di- decanoyl peroxide, dilauroyl peroxide, dibenzoyl peroxide, bis (o-toluyl), Succinylpe- hydroxide, methyl ethyl ketone peroxide, di-tert-butyl butyl hydroperoxide, acetyl, butyl peracetate, tert-Butylpermaleinat, tert-butyl perisobutyrate, tert-butyl perpivalate, tert-butyl peroctoate, tert-butyl perneodecanoate, tert-butyl perbenzoate, tert-butyl hydroperoxide, cumene hydroperoxide, tert-butyl perneodecanoate , tert-amyl perpivalate pylperoxidicarbamat, tert-butyl perpivalate, tert-butyl perbenzoate, tert-butyl peroxy-2-ethylhexanoate and diisopropyl; further, lithium, sodium, potassium and Ammoniumperoxodisul- fat, azo initiators, 2,2'-azobisisobutyronitrile, 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobis [2-methyl-N- ( -2-hydroxyethyl) propionamide, 1, 1-azobis (1 -cyclohexancarbonitril), 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (N, N'-dimethylenisobutyroamidin) - dihydrochloride, and 2,2'-azobis (2-amidinopropane) dihydrochloride, and the redox initiator systems described in the following.

Redox initiator systems contain at least one peroxide-containing compound in combination with a redox co-initiator, for example a reducing sulfur compound, eg. B. bisulfites, sulfites, thiosulfates, dithionites and tetrathionates of alkali metals or of ammonium compounds. So you can use combinations of peroxodisulfates with alkali metal or ammonium, z. B. Ammoniumperoxo- peroxodisulfate and ammonium. The amount of the peroxide-containing compound to redox co-initiator is from 30: 1 to 0.05: 1. The initiators can be used alone or in mixture with one another, z. Mixtures of hydrogen peroxide and sodium peroxodisulfate example.

The initiators can not or only slightly be soluble both water soluble and water. For the polymerization in aqueous medium are preferably used water-serlösliche initiators, that initiators which are soluble in the commonly used for the polymerization concentration in the aqueous polymerization medium. These include peroxodisulfates, azo initiators having ionic groups, organic hydroperoxides containing up to 6 C atoms, acetone, methyl ethyl ketone hydroperoxide and hydrogen peroxide, as well as the above-mentioned redox initiators.

In combination with the initiators or redox initiator systems, transition metal catalysts can be used in addition, z. As salts of iron, cobalt, Ni disgust, copper, vanadium and manganese. Suitable salts are, for. B. Eisen (II) .sulfat, cobalt (II) chloride, nickel (II) sulfate, or copper (l) chloride. Based on the monomers, the reducing transition metal salt is used in a concentration of 0.1 ppm to 1000 ppm. Thus, one can use combinations of hydrogen peroxide with salts egg sen (II), such as 0.5 to 30% hydrogen peroxide and 0.1 to 500 ppm of Mohr's salt.

Also in the copolymerization according to the invention in organic solvents, redox coinitiators and / or transition metal catalysts can also be used in combination with the above initiators, z. As benzoin, dimethylaniline, ascorbic acid and organic solvent-soluble complexes of heavy metals, such as copper, cobalt, iron, manganese, nickel and chromium. The amounts usually used of redox coinitiators or transition metal catalysts are about 0.1 to 1000 ppm, based on the amounts of monomeric ren.

In order to control the average molecular weight of the polymers according to the invention available, it is often convenient to carry out the copolymerization according to the invention in the presence of regulators. Customary regulators may be used, in particular organic SH-containing compounds, in particular water-soluble SH group-containing compounds such as 2-mercaptoethanol, 2-mercaptopropanol, 3-mercaptopropionic acid, cysteine, N-acetylcysteine, further phosphorous (III) - or phosphorus (I) compounds such as alkali metal or Erdalkalimetallhy- pophosphite, z. B. sodium, and hydrogen sulfites as sodium hydrogen sulfite. The polymerization regulators are generally used in amounts of from 0.05 to

10 wt .-%, especially 0.1 to 2 wt .-%, based on the monomers. Preferred regulators are the abovementioned SH-carrying compounds, especially water soluble SH-group-carrying compounds such as 2-mercaptoethanol, 2-mercaptopropanol, 3-mercaptopropionic acid, cysteine ​​and N-acetylcysteine.

The polymerization can be carried out according to the usual polymerization processes take place, including solution, precipitation, suspension or bulk polymerization. the method of solution polymerization is preferred that the polymerization in solvents or diluents.

Suitable solvents or diluents include both aprotic solvents, for counting. For example, the aforementioned aromatics such as toluene, o-xylene, p-xylene, cumene, chlorobenzene, ethylbenzene, technical-grade mixtures of alkyl aromatics, aliphatics and cycloaliphatics such as cyclohexane and technical aliphatics, ketones such as acetone, cyclohexanone and methyl ethyl ketone, ethers such as tetrahydrofuran, dioxane,

Diethyl ether, tert-butyl methyl ether, and Ci-C4-alkyl esters of aliphatic Ci-C4-carboxylic acids such as methyl acetate and ethyl acetate, further protic solvents such as glycols and glycol derivatives, polyalkylene glycols and their derivatives, Ci-C4-alkanols, such. B. n-propanol, n-butanol, isopropanol, ethanol or methanol, and water and mixtures of water with Ci-C4-alkanols such. As isopropanol / water mixtures. Preferably Copolymerisati- to the invention proceeds onsverfahren in water or a mixture of water with up to 60 wt .-% of Ci-C4-alkanols or glycols as solvent or diluent. Water is particularly preferably used as the sole solvent.

The polymerization is preferably substantial or complete exclusion of oxygen, preferably in an inert gas stream, for example. B. performed a nitrogen stream.

The polymerization can be carried out in the apparatuses customary for polymerization. These include stirred tanks, stirred tank cascades, autoclaves, tubular reactors and kneaders.

The polymerization is usually carried out at temperatures ranging from 0 to 300 ° C, preferably in the range of 40 to 120 ° C. The polymerization time is usually in the range of 0.5 h to 15 h and in particular in the range of 2 to 6 hours. The ruling in the polymerization pressure is in the success of polymerization of secondary importance and is usually in the range of 800 mbar to 2 bar and frequently ambient pressure.

Depending on the choice of the polymerization conditions comprise the polymeric UV absorber is usually weight average molecular weights (M w) in the range of 10,000 to 500,000 g / mol, preferably 12,000 to 300,000 g / mol, in particular from 15,000 to 100,000 g / mol. The weight average molecular weight M w can in a conventional manner by gel permeation chromatography, as explained in the examples are determined.

If the polymerization is carried out as a solution polymerization in water, a water removal is not required for many applications. Moreover, isolation of the polymeric UV absorber in the usual way in itself can be carried out, for example. For example, by spray drying of the polymerization mixture. If the polyvinyl lymerisation in a steam-volatile solvent or solvent mixture is performed, one can remove the solvent by injecting water vapor. the polymeric UV absorbers are preferably obtained in the form of an aqueous dispersion or solution. The solids content is preferably 10 to 80 wt .-%, in particular 30 to 65 wt .-%.

The invention further relates to polymeric UV absorber comprising, as monomer units a), a UV absorber comprising an ethylenically unsaturated group (UV-monomer), and

b) a polyalkylene oxide containing an ethylenically unsaturated group (monomer PEG), the PEG monomer of formula A corresponds,

wherein R1 = H or CH 3, R2 = H or Ci-Ci 2 -alkyl, R 3 = H or Ci-Ci 2 -alkyl, R4 = H or Ci-Ci2-alkyl, and n = 3 - 50. Preferred embodiments of the polymeric UV absorber are as described above. The invention also relates to a process for the preparation of the polymeric UV absorber according to the invention, wherein the UV-monomer and the PEG-monomer are radically polymerized. Suitable and preferred embodiments are as described above. The polymeric UV absorbers according to the invention are outstandingly suitable as additives for agrochemical formulations. Therefore, the invention also relates to a composition comprising a pesticide and a polymeric UV absorber according to the invention. The agrochemical composition according to the invention generally comprises 0.1 to 50 wt .-%, preferably 0.5 to 30 wt .-%, more preferably 1, 0 to 15 wt .-% polymeric UV absorber, each based on the composition.

The agrochemical composition according to the invention comprises in general from 0.01 to 95 wt .-%, preferably 0.5 to 80 wt .-%, particularly preferably 2 to 50 wt .-% and especially 5 to 20 wt.% Pesticide, based on the composition.

The weight ratio of pesticide to polymeric UV absorber is usually from 30: 1 to 1: 3, preferably 15: 1 to 1: 2, more preferably 8: 1 to 1: 1.

The term pesticide refers to at least one active substance selected from the group of fungicides, insecticides, nematicides, herbicides, safeners and / or growth regulators. Preferred pesticides are fungicides, insecticides and herbicides, in particular insecticides. Also mixtures of pesticides of two or more of the aforementioned classes can be used. The expert is familiar with such pesticides, for example, in Pesticide Manual, 14th Ed. (2006), The British Crop Protection Council, London can be found. Suitable insecticides are insecticides of the class of carbamates, organophosphates, organochlorine insecticides, phenylpyrazoles, pyrethroids, neonicotinoids, Spinosine, avermectins, milbemycins, juvenile hormone analogs, alkyl halides, organotin compounds, nereistoxin analogs, ureas benzoyl, diacylhydrazines, METI acaricides, and insecticides such as chloropicrin, Py- metrozin, flonicamid, clofentezine, hexythiazox, etoxazole, diafenthiuron, propargite, tetradifon, chlorfenapyr, DNOC, buprofezin, cyromazine, amitraz, hydramethylnon, acequinocyl, fluacrypyrim, rotenone, or derivatives thereof. Suitable fungicides are fungicides of the classes dinitroanilines, allylamines, anilinopyrimidines, antibiotics, aromatic hydrocarbons, benzenesulfonamide, benzimidazoles, benzisothiazoles, benzophenones, benzothiadiazoles, benzotriazines, benzyl carbamates, carbamates, carboxamides, Carbonsäureamdide, Chloronitrile, Cyanoacetamideoxime, Cyanoimidazole, Cyclopropanecarboxamide, dicarboximides, Dihydrodioxazine , Dinitrophenylcrotonate, dithiocarbamates, dithiolanes, Ethylphosphonate, Ethylaminothiazolcarboxamide, guanine nidines, hydroxy (2-amino-) pyrimidine, Hydroxyanilides, imidazoles, imidazolinones, A- norganika, Isobenzofuranone, methoxyacrylates, Methoxycarbamates, Morpholines, N-phenyl carbamates, Oxazolidinedione, Oximinoacetate , Oximinoacetamide, rimidinnucleoside Peptidylpy-, phenylacetamides, phenylamides, phenylpyrroles, phenylureas, phosphonates, Phosphorothiolate, Phthalamsäuren, phthalimides, piperazines, Piperidi- ne, propionamides, pyridazinones, pyridines, Pyridinylmethylbenzamide, P yrimidinamine, pyrimidines, Pyrimidinonehydrazone, Pyrroloquinolinone, quinazolinones, quinolines, quinones, sulfamides, Sulfamoyltriazole, Thiazolecarboxamide, thiocarbamates, thiocarbamates, thiophanate, Thiophenecarboxamide, Tolua-mide, triphenyltin compounds, triazines, triazoles. Suitable herbicides include herbicides of the classes of acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzoic zothiadiazinone, bipyridylium, carbamates, Chloroacetamide, chlorine carboxylic acids Cyc- lohexanedione, dinitroanilines, dinitrophenol, diphenyl ethers, glycines, imidazolinones, isoxazoles, isoxazolidinones , nitriles, N-phenylphthalimide, oxadiazoles, Oxazolidinedione, oxyacetamides, phenoxycarboxylic acids, phenyl carbamates, phenylpyrazoles, Phenylpy- razoline, Phenylpyridazine, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridine carboxylic acids, Pyridinecarbo- xamide, pyrimidinediones, pyrimidinyl (thio ) benzoate, quinolinecarboxylic acids, Semicarba- zone, sulphonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, Thiadiazo- le, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolinones, triazolo carboxamides, triazolopyrimidines, triketones, uracils, and ureas.

Preferred herbicides are napropamide, Proparnil, bentazone, paraquat dichloride, loxydim Cyc-, sethoxydim, ethalfluralin, oryzalin, pendimethalin, trifluralin, Acifluren, nifen Aclo-, fomesafen, oxyfluoren, ioxynil, Imazetapyr, imazaquin, chloridazon, norflurazon, thiazopyr, triclopyr, dithiopyr , diflufenican, picolinafen, amidosulfuron, molinate, comparable nolate, Promethon, metribuzin, azafenidin, carfentrazone-ethyl, sulfentrazone, metolachlor Xuron, monolinuron, fluchloralin and Flurenol. Preferred fungicides are cyprodinil, fuberidazole, dimethomorph, Procloraz, triflumizole, tridemorph, Edifenfos, fenarimol, nuarimol, ethirimol, Quinoxylen, dithianon, metominostrobin, trifloxystrobin, Dichloflu- amide, Bromuconnazol and myclobutanil. Preferred insecticides acephate, azinphos-ethyl, azinphos-methyl, isofenphos, chlorpyrifos-methyl, dimethylvinphos, phorate, phoxim, prothiofos, cyhexatin, alanycarb, ethiofencarb, pirimicarb, thiodi- carb, fipronil, bioallethrin, bioresmethin, deltamethrin, fenpropathin , Flucythrinate, Taufluvalinate, alpha-cypermethrin, metaflumizone, Zetacypermethrin, resmethin, tefluthrin, lambda cyhalothrin and hydramethylnon. In a further embodiment, preferred pesticides pyrethroids or metaflumizone, in particular pyrethroids. Particularly preferred pesticides are alpha-cypermethrin and metaflumizone.

In one embodiment of pesticides are used, which are UV-sensitive. These UV sensitivity can be determined in simple preliminary tests. Preferably pesticides are regarded as UV-sensitive, if strength upon irradiation of a pesticide film weight by drying an 25th% solution of the pesticide in a suitable solvent, preferably in acetone, with UVA / IS-light of wavelength 300-800 nm within 24 h at 25 ° C composed of at least 20.% are degraded. Typically, this is an illumination intensity from 10,000 to 100,000 lux, preferably 50,000 to 80,000 Lux used. The pesticides are considered to be degraded when the concentration of the pesticide (or a pesticidal component in a mixture of several pesticides components) is reduced accordingly. There are generally several ways known as degrade UV sensitive pesticides. So chemical bonds can be isomerized, radicalized or split, and optionally thereafter reacting again. For example, E / Z isomers may double bonds of pesticides (such as metaflumizone) by UV light are isomerized so that an isomer that has pesticidal activity is stored in the other environmentally isomer has less activity. With the composition of the invention and the UV absorbers according to the invention any or all of these pathways can be inhibited.

The composition of the invention may be in the stakes for agrochemical formulations usual types of compositions such. As solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type depends on the particular intended use; it should ensure a fine and uniform distribution of the compound of the invention in any case. Examples for composition types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), E- mulsionen (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS ) or granules (GR, FG, GG, MG), which can be soluble or dispersible either in water, as well as gels for treatment of plant propagation materials such as seeds (GF). Bait for animals, such as ants or rats, various of the foregoing types of compositions can be present, preferably as a powder, pastes, granules or gels. Generally, the composition types (eg. B. SC, EC OD, FS, WG, SG, WP, SP, SS, WS, GF) are employed diluted. Supply sammensetzungstypen as DP, DS, GR, FG, GG, MG or bait be used undiluted as a rule. Preferred composition types are suspensions.

The inventive compositions may further contain auxiliaries customary for crop protection agents, wherein the selection of the aid according to the specific application form or the active compound. Examples of suitable auxiliaries are solvents, solid carriers, surface active compounds (lubilisatoren as more solar, protective colloids, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and adhesives (for. Example, for seed treatment) or customary auxiliaries for bait formulation (z. B. attractants, animal feed, bitter substances).

As the solvent, water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl, fatty acids and fatty acid esters and strongly polar solvents, for example amines such as N-methylpyrrolidone. In principle, solvent mixtures can be used as well as mixtures of the aforementioned solvents and water.

Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products such as cereal flour, tree bark, wood and nutshell meal, cellulose powder or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, adhesives, dispersants or emulsifiers) are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, come. B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphthalene (Morwet ® types, Akzo Nobel, USA) and dibutyl (nekal ® types, BASF, Germany), and of fatty acids, alkyl - and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers Canole, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl, tributyl tylphenylpolyglykolether, alkylaryl polyether alcohols, isotridecyl alcohol, Fettalkoholethy- oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or Polyoxypropylenal-, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and proteins, denatured proteins, polysaccharides (eg Methylc ellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol ® types, Clariant, Switzerland), Polycarboxyla- te (Sokalan ® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lupamin ® - types, BASF, Germany), polyethyleneimine (Lupasol ® types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.

Examples of thickeners (ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion) are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ®, CP Kelco, U.S.A.), Rhodopol ® 23 (Rho dia, France) or Veegum ® (RT Vanderbilt, USA) or attaclay ® (Engelhard Corp., NJ, USA). Bactericides can be added to stabilize the composition. Examples of bactericides are those based on dichlorophen and benzyl alcohol formal and isothiazolinone derivatives such as alkylisothiazolinones and Benzisothiazolino- nen (Acetide ® MBS from Thor Chemie).. Examples of suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

Examples of defoamers are 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.

Examples of composition types are:

1 . Composition types for dilution with water

i) Water-soluble concentrates (SL, LS)

10 parts by weight of the pesticide are dissolved in 90 parts by weight of water or a water-soluble solvent. Alternative, wetters or other auxiliaries are added. On dilution in water, the pesticide dissolves. Obtained in this way, a composition with 10 wt .-% active ingredient. ii) Dispersible concentrates (DC)

20 parts by weight of the pesticide in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersing agent such. As polyvinylpyrrolidone dissolved. When diluted with water gives a dispersion. The active compound content is 20 wt .-%

iii) Emulsifiable concentrates (EC)

15 parts by weight of the pesticide in 75 parts by weight of xylene with addition of

Calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) was dissolved. Dilution with water gives an emulsion. The composition of is 15 wt .-% active ingredient.

iv) Emulsions (EW, EO, ES)

25 parts by weight of the pesticide can be dissolved with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) in 35 parts by weight of xylene. This mixture is by means of an emulsifying machine (z. B. Ultra-Turrax) at 30

Parts by weight of added water and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active ingredient content of 25 wt .-%.

v) Suspensions (SC, OD, FS)

20 parts by weight of the pesticide be yaw dispersants with addition of 10 parts by weight of crushed and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active substance content in the composition is 20% by weight.

vi) Water-dispersible and water-soluble granules (WG, SG)

50 parts by weight of the pesticide be yaw with addition of 50 parts by weight of dispersants and wetting agents and finely ground by means of technical appliances (for. Example TRUSION Ex, spray tower, fluidized bed) prepared as water or wasserlösli- che granules. Dilution with water gives a stable dispersion or solution of the active compound. The composition has an active ingredient content of 50 wt .-%.

vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the pesticide be yaw dispersants with addition of 25 parts by weight and ground wetters and silica gel in a rotor-stator mill. Dilution with water gives a stable dispersion or solution of the active compound. The active ingredient content of the composition is 75 wt .-%.

viii) gels (GF)

In a ball mill, 20 parts by weight of the pesticide, 10 parts by weight

Dispersants, 1 part by weight of swelling agent ( "gelling agent") and ground 70 parts by weight of water or an organic solvent to give a fine suspension. Dilution with water gives a stable suspension containing 20 wt .-% active ingredient results.

2. Composition types to be applied undiluted

ix) Dustable powders (DP, DS)

5 parts by weight of the pesticide are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5 wt .-% active ingredient.

x) Granules (GR, FG, GG, MG)

0.5 parts by weight of the pesticide is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with 0.5 wt .-% of active ingredient;

xi) ULV solutions (UL)

10 parts by weight of the pesticide are solvents in 90 weight parts of an organic solu- z. B. xylene dissolved. This gives a composition to be applied undiluted with 10 wt .-% active ingredient.

The compounds can be used as such or in the form of their compositions, eg. B. in the form of directly sprayable solutions, powders, suspensions, dispersions, E- mulsionen, oil dispersions, pastes, dusts, materials for spreading or granules, by spraying, atomizing, dusting, scattering, bait station, swabbing, dipping or pouring. Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) are prepared by addition of water. th To prepare emulsions, oil dispersions, the substances Pas- or dissolved in an oil or solvent as such or by means of wetter, tackifier, dispersant or emulsifier can be homogenized in water. but it can also consist of active substance, wetter, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared which are suitable for dilution with water.

The active ingredient concentrations in the finished formulations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. The application rates for the use in crop protection depending on the type of effect desired, between 0.01 and 2.0 kg of active compound per ha. In the treatment of plant propagation materials, such. Example seed, amounts of active compound are generally from 1 to 1000 g / 100 kg, preferably used 5 to 100 g / 100 kg of propagation material or seeds. When used in the protection of materials or stored products, the amount of active ingredient depends on the type of application area and on the desired effect. Usual amounts up wall are the protection of materials, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.

The present invention further relates to a method of combating phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, where the composition of the invention to the particular pests, their habitat, or allowed to act before the particular pest to be protected plants, the soil and / or on undesired plants and / or the crop plants and / or their habitat. Under habitat, the cultivation, the crop plants or the plant material is customarily area of ​​useful plants, understood. The inventive composition containing a pesticide is naturally not suitable for use in humans and not admitted. is advantages of the present invention that the polymeric UV absorber to stabilize UV-sensitive pesticides, especially already at low concentrations of polymethyl rem UV absorbers. Another advantage is that less surfactants used are brewing chen to a high stability of drug dispersions to obtain particular drug suspensions. It is also advantageous that UV absorbers of the invention can reduce the surface tension of water more, which means that they report a higher surface activity. The UV absorbers are readily soluble in agrochemical formulations, or highly compatible with see agrochemical formulations, such as aqueous emulsions and aqueous suspensions. For example, no additional emulsifier is necessary in order to incorporate the UV absorber into the formulation.

The following examples illustrate the invention without limiting it.

Examples

UV absorber A: 2- (2'-hydroxy-5'-methacryloxyethylphenyl) -2H-benzotriazole (CAS no.

96478-09-0), commercially available as Ciba® Tinuvin® R796 from CIBA Chemicals special- ty.

MPEGMA350 (methyl polyethylene glycol-350-methyl acrylate), MPEGMA475 (methyl polyethylene glycol-475-methyl acrylate), and MPEGMA1 100 (Methylpolyethylenglykol- 1100-methyl acrylate) are (by esterification or transesterification of methacrylic acid or methyl methacrylate to the corresponding methyl polyethylene glycol average molecular weight 375, 475 or 1 100 g / mol) available. MPEGMA350 is commercially available as Bisomer® MPEG350MA of Cognis.

example 1

Were provided 76.2 g of toluene and heated under nitrogen to 75 ° C. Subsequently, 105.6 g of a 65% solution of MPEGMA1 100 in toluene and 155.0 g of a 13% solution of UV absorber A in toluene were added over a period of 5 hours. Simultaneously added over a period of 5.5 hours, 0.65 g of t-butyl peroxopivalate in 28.3 g of toluene. Polymerization was then continued for one hour. Thereafter 207.1 g water was added and the toluene circles excluded. a 19 wt .-% clear aqueous solution of polymer 1 (Mw was obtained

27900 g / mol as determined by gel permeation chromatography) with a pH of 7.3.

example 2

Analogously to Example 1, a polymer was prepared, in addition methacrylic acid (MAS) was copolymerized. The molar ratio of UV absorber to methacrylic acid and the resulierenden molecular weights of the polymers 2 and 3 are shown in Table 1 summarized. The polymers were clear water.

example 3

Were provided 77.9 g of toluene and heated under nitrogen to 75 ° C. Subsequently, 200.7 g MPEGMA475 and 1049.8 g of a 13% solution of UV absorber A in toluene were added over a period of 5 hours. At the same time was added over a period of 5.5 hours, 4.4 g of t-butyl peroxopivalate in 44.7 g of toluene. Polymerization was then continued for one hour. Thereafter 786.7 g water was added and the toluene azeotropically. Then 0.34 g sodium hydroxide solution (25% strength) was netraulisiert. a 15% aqueous solution of the polymer 4 was obtained with a pH of 7.5.

example 4

Were initially introduced 150.7 g of toluene and heated under nitrogen to 75 ° C. Subsequently, 147.9 g MPEGMA350 and 1050.0 g of a 13% solution of UV absorber A in toluene were added over a period of 5 hours. At the same time was added over a period of 5.5 hours, 4.41 g of t-butyl peroxopivalate in 45.6 g of toluene. Polymerization was then continued for one hour. Thereafter 663.6 g water was added and the toluene azeotropically. Then 0.34 g sodium hydroxide solution (25% strength) was netraulisiert. 1 a 1% aqueous solution of the polymer 5 Man erhiellt with a pH of 7.6.

Overview of the polymers from Examples 1 to 4

Table 1

example 5

A commercial formulation of metaflumizone (Alverde®) containing 240 g / l metaflumizone was treated with 96 g / l Polymer no. 1 -5 and then was was diluted with water so as to give an active ingredient content of 10 g / l. Approximately 20 mg of the formulation so prepared were applied to a microscope slide to dry for 30 minutes to cool and 24 h continuously exposed (Atlas Suntest CRT plus, corresponding to setting "outdoor", exposure, the same spectrum and intensity as normal sunlight at noon in summer). After the exposure time the samples were dissolved in dimethylsulfoxide the residual content of metaflumizone was (by quantitative UPLC BEH C18 column 1, 7 μηι 2,1x100;. elution with a gradient of acetonitrile / 0.1% H3P04 rising of 5/95 to 95 / 5) is determined (reference) For comparison, in each bracketing a sample without UV Abosrber run along allowed evaluation.:. 2 samples were dissolved than zero samples after drying without exposure at once and the content of metaflumizone determined the resulting average value was as. 100% and the remaining samples normalized against it. the results of ER are summarized in table 2.

table 2

a) not according to the invention

Claims

claims
A composition comprising a pesticide and a polymeric UV absorber as monomeric units
a) a UV absorber comprising an ethylenically unsaturated group (UV monomer), and
b) a polyalkylene oxide containing an ethylenically unsaturated group (PEG monomer)
includes.
The composition of claim 1, wherein the PEG monomer containing at least three alkylene oxide groups.
The composition of claim 1 or 2, wherein the PEG monomer contains five to 50 alkylene oxide groups.
A composition according to any one of claims 1 to 3, wherein the polymeric UV absorber containing, as monomer unit c) (meth) acrylic acid.
Composition according to one of claims 1 to 4, wherein the molar ratio of monomer to UV-PEG monomer in the range of 1: 1: 9 to. 9
Composition according to one of claims 1 to 5, wherein the UV-monomer contains a benzotriazole groups.
A composition according to any one of claims 1 to 6, wherein the molar ratio of (meth) acrylic acid to UV monomer in the range of from 1: 9 to 9: 1.
A composition according to any one of claims 1 to 7, wherein the polymeric UV absorber has a proportion of UV monomer to all monomeric units of from 5 to 70 mol%.
Composition according to one of claims 1 to 8, wherein the molecular weight is M of the polymeric UV absorber in the range from 10,000 to 500,000 g / mol.
A composition according to any one of claims 1 to 9, wherein the pesticide is sensitive to UV.
A composition according to any one of claims 1 to 10, wherein the weight ratio of pesticide to polymeric UV absorbers in the range of 30: 3: 1 to. 1
12. The composition according to any one of claims 1 to 1 1, wherein the pesticide napropamide, Proparnil, bentazone, paraquat dichloride, cycloxydim, sethoxydim, ethalfluralin, oryzalin, pendimethalin, trifluralin, Acifluren, aclonifen, fomesafen oxyfluoren, ioxynil, Imazetapyr, imazaquin, chloridazon , norflurazon, thiazopyr, triclopyr, dithiopyr, diflufenican, picolinafen, amidosulfuron, molinate, vernolate, Promethon, metribuzin, azafenidin, carfentrazone-ethyl, sulfentrazone, metoxu- ron, monolinuron, fluchloralin, flurenol, cyprodinil, fuberidazole, dimethomorph, Procloraz, triflumizole , tridemorph, Edifenfos, fenarimol, nuarimol, ethirimol, noxylen Qui, dithianon, metominostrobin, trifloxystrobin, Dichlofluamid, Bromuconna- zole, myclobutanil, acephate, azinphos-ethyl, azinphos-methyl, isofenphos, chlorpyriphos-methyl, dimethylvinphos, phorate , phoxim, prothiofos, cyhexatin, alany- carb, ethiofencarb, pirimicarb, thiodicarb, fipronil, bioallethrin, bioresmethin, tamethrin Del-, fenpropat out Flucythrinate, Taufluvalinate, alpha-cypermethrin, methyl taflumizon, Zetacypermethrin, resmethin, tefluthrin, lambda cyhalothrin or hydramethylnon is.
13, polymeric UV absorbers comprising as monomeric units
a) a UV absorber comprising an ethylenically unsaturated group (UV monomer), and
b) a polyalkylene oxide containing an ethylenically unsaturated group (monomer PEG), the PEG monomer of formula A corresponds, wherein R1 = H or CH 3, R2 = H or Ci-Ci 2 -alkyl, R 3 = H or Ci-Ci 2 -alkyl, R4 = H or Ci-Ci 2 alkyl, and n = 3-50.
14. A process for preparation of the polymeric UV absorber as claimed in claim 13, wherein the UV-monomer and the PEG-monomer are radically polymerized.
15. A method for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, where the composition according to claims 1 1 to 14 to the respective pests, their habitat, or allowed to act before the particular pest to be protected plants, the soil and / or on undesired plants and / or the crop plants and / or their habitat.
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