EP2373158A2 - Composition agrochimique comprenant un pesticide et un absorbeur d'uv - Google Patents

Composition agrochimique comprenant un pesticide et un absorbeur d'uv

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Publication number
EP2373158A2
EP2373158A2 EP09795363A EP09795363A EP2373158A2 EP 2373158 A2 EP2373158 A2 EP 2373158A2 EP 09795363 A EP09795363 A EP 09795363A EP 09795363 A EP09795363 A EP 09795363A EP 2373158 A2 EP2373158 A2 EP 2373158A2
Authority
EP
European Patent Office
Prior art keywords
absorber
alkyl
pesticide
weight
alkoxy
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Withdrawn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
EP09795363A
Other languages
German (de)
English (en)
Inventor
Andrea Misske
Christian Bittner
Michael Ishaque
Markus Hoffmann
Richard Riggs
Rüdiger Sens
Andre Kabat
Sylke Haremza
Douglas D. Anspaugh
David M. Terry
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
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP2373158A2 publication Critical patent/EP2373158A2/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Withdrawn legal-status Critical Current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
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas 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
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • Agrochemical composition comprising pesticide and UV absorber
  • the present invention relates to an agrochemical composition comprising pesticide and UV absorber, as well as the aforementioned UV absorbers. Furthermore, the invention relates to the use of UV absorbers in agrochemical compositions. It also 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. Combinations of preferred features with other preferred features are encompassed by the present invention.
  • Agrochemical compositions comprising pesticide and UV absorber are well known:
  • WO 1992/03926 discloses insecticidal compositions comprising a pyrethroid, a UV absorber and an antioxidant.
  • EP 0 376 888 A1 discloses compositions for controlling harmful insects comprising a substance which alters the behavior of the harmful substance and a pesticidally active compound, both of which are contained in a flowable matrix which protects the behavior-modifying substance from UV radiation.
  • the compositions generally consist of 51 to 98% by weight of the matrix, which is usually a UV absorber, which preferably has a viscosity of 1000 to 40,000 cp.
  • a suitable UV absorber is, for example, a mixture of the following alkoxylated 2- (2-hydroxyphenyl) -benzotriazoles TinuA and TinuB
  • TinuB in the weight ratio TinuA to TinuB of 50 to 38 which is available under the trade name Tinuvin® 1 130 from Ciba.
  • WO 2006/089747 discloses a method for protecting materials comprising applying a composition comprising a capsule containing a photolabile pesticide and a UV absorber such as alpha- [3- [3- (2H-benzotriazol-2-yl) -5- (1 , 1-dimethylethyl) -4-hydroxyphenyl] -1-oxopropyl] -omega-hydroxy-poly (oxy-1,2-ethanediyl).
  • WO 1997/42815 discloses a composition comprising a 0.1 to 20% pesticide, 0.01 to 30% pheromone and 40 to 98% UV absorber.
  • a UV absorber for example, Tinuvin 1130 can be occupied.
  • WO 2008/085682 discloses a composition comprising photolabile pesticide and a UV protecting agent, which may be, for example, Uvinul® P25 (PEG-25 para-aminobenzoic acid).
  • Cinnamic acid derivatives containing alkoxylated groups are also known: Philippon et al. (Synthetic Communications, 1997, 27 (15), 2651-2682) disclose a compound of the formula
  • the UV absorbers of the prior art have various disadvantages: other auxiliaries such as antioxidants must be added.
  • the UV absorbers must be used in a matrix. The UV absorbers were unable to stabilize photosensitive pesticides for sufficient time.
  • the object of the present invention was to provide alternative UV absorbers for use in agrochemical compositions. Another object was to find UV absorbers that stabilize UV-sensitive pesticides. The stabilization should be better than in the prior art, especially at lower concentrations of UV absorber. It was another object to find UV absorbers which allow easier formulation of pesticides, for example by requiring less adjuvants such as surfactants.
  • AO C 2 -C 4 alkoxy or CH 2 CH 2 NH; n: 3-50; m: 1 if UV is A or B, 3 if UV is C;
  • X NH or O
  • Ri is H or Ci-C 24 alkyl
  • UV a group selected from the formulas A to C, wherein R 2 : H, CN or CO 2 - (Ci-Ci 6 alkyl);
  • R 3 is H, C 1 -C 6 -alkyl, phenyl or phenyl substituted with C 1 -C 18 -alkoxy;
  • R 4 H or C 1 -C 18 alkoxy
  • R 5 is H, C 1 -C 18 alkyl, OH, or C 1 -C 18 alkoxy; R 6 : CrC 8 alkylene; or
  • R 7 is H or C 1 -C 12 alkyl; is, which are bound via # to the carbonyl group of I corresponds.
  • pesticide denotes 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, especially insecticides.
  • 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, alkylhalides, organotin compounds, nereistoxin analogues, 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, n
  • 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
  • Preferred herbicides are napropamide, proparnet, bentazone, paraquat dichloride, cyclopydim, sethoxydim, ethalfluralin, oryzalin, pendimethalin, trifluralin, aciflurene, aconifen, fomesafen, oxyfluorene, loxynil, imazetapyr, imazaquin, chloridazon, norflurazon, thiazopyr, triclopyr, dithiopyr , Diflufenican, picolinafen, amidosulfuron, molinates, enolates, promethone, metribuzin, azafenidine, carfentrazone-ethyl, sulfentrazone, metaxuron, monolinuron, fluchloralin and flurenol.
  • Preferred fungicides are cyprodinil, fuberidazole, dimethomorph, proclonaz, triflumizole, tridemorph, edifenfos, fenarimol, nuarimol, ethirimol, quinoxylene, dithianone, metominostrobin, trifloxystrobin, dichlofluamide, bromuconnazole and myclobutanil.
  • Preferred insecticides are acephates, azinophos-ethyl, azinphos-methyl, isofenphos, chlorpyriphos-methyl, dimethylvinphos, phorates, phoxim, prothiofos, cyhexatin, alanycarb, ethiofencarb, pirimicarb, thiodi carb, fipronil, bioallethrin, bioresemeth, deltamethrin, fenpropathine , Flucythrinates, baptized fluvalinates, alphacypermethrin, metaflumizone, cetacypermethrin, resmethin, tefluthrin, lambda cyhalothrin and hydramethylnon.
  • preferred insecticides are pyrethroids or metaflumizone, especially pyrethroids. Particularly preferred pesticides are alphacypermethrin and metaflumizone.
  • pesticides that are UV sensitive are used. This UV sensitivity can be determined in simple preliminary tests. Pesticides are preferably UV-sensitive when irradiated with a pesticide film obtained by drying a 25% strength by weight solution of the pesticide in a suitable solvent, preferably in acetone, with UV light, preferably UVA / IS light Wavelength 300-800 nm, be degraded within 24 h at 25 0 C to at least 20 wt.%.
  • the pesticides are considered to be degraded if the concentration of the pesticide (or a pesticide component in a mixture of several pesticide components) is correspondingly reduced.
  • Suitable UV absorbers are the structures of the formula I as defined above.
  • Suitable radicals AO are C 2 -C 4 alkoxy or -CH 2 CH 2 NH-, preferably -CH 2 CH 2 NH-, where C 2 -C 4 alkoxy is preferably -CH 2 CH 2 O-, -CH (CH 3 ) CH 2 O- or -CH (CH 2 CH 3 ) CH 2 O-, in particular -CH 2 CH 2 O-.
  • the subscript n stands for 3 to 50, preferably 3 to 30, in particular 3 to 25 and especially 3 to 15.
  • the subscript m stands for 1 if UV stands for A, B or D, or for 3 if UV stands for C.
  • Suitable radicals X are NH or O, preferably O.
  • Suitable radicals R 1 are H or C 1 -C 24 -alkyl, preferably C 1 -C 6 -alkyl, in particular CH 3 .
  • Ri is H or -C 24 alkyl, preferably C 6 - C 24 alkyl, more preferably C 6 -C 24 alkyl, in particular Cs-C 2 O alkyl, especially Cio-C 2 o alkyl, very specially CIO C 2 o branched alkyl.
  • polyethylenimine groups may be linear or branched, preferably branched Branched polyethylenimine groups usually have primary, secondary and tertiary amino groups
  • the molar ratio of primary / secondary / tertiary amino groups may be in the range from 1 / 0.5 / 0.2 to 1/1, 9 / 1.5, preferably in the range from 1 / 0.7 / 0.4 to 1 / 1, 5/1, 1.
  • Suitable groups UV are groups selected from the formulas A to C, preferably from B or C, the groups being bonded via # and the carbonyl group of formula I.
  • a suitable radical UV is a structure of the formula A.
  • R 2 H, CN or CO 2 - (Ci-Ci 6 alkyl), preferably CN or CO 2 - (Ci-Ci 6 alkyl), in particular CN;
  • R 3 is H, C 1 -C 6 -alkyl, phenyl or C 1 -C 6 -alkoxy-substituted phenlyl, preferably C 1 -C 6 -alkyl, phenyl or C 1 -C 18 -alkoxy-substituted phenyl, in particular phenyl or C 1 -C 18 -alkoxy-substituted phenyl; and
  • R 4 H or CrCl 8 alkoxy, preferably H.
  • Another suitable radical UV is a structure of the formula B.
  • R 5 is H, C 1 -C 18 alkyl, OH or C 1 -C 18 alkoxy, preferably H; and R 6 is C 1 -C 5 -alkylene, preferably C 1 -C 2 -alkylene, in particular CH 2.
  • Another suitable radical UV is a structure of the formula C.
  • R 7 is H or C 1 -C 12 -alkyl, preferably H.
  • the agrochemical composition comprises pesticide and UV absorber, wherein the UV absorber of a structure of formula III
  • n 3 to 50, preferably 3 to 25;
  • R 10 H, CN or CO 2 - (Ci-Ci 6 alkyl), preferably H or CN, in particular H;
  • R 1 is H, C 1 -C 6 -alkyl, phenyl or phenyl substituted by C 1 -C 18 -alkoxy, preferably H, phenyl or C 1 -C -alkoxy-substituted phenyl, in particular H;
  • R 12 H or C 1 -C 18 alkoxy, preferably H; and R 13 : H or C 1 -C 24 alkyl, preferably CH 3.
  • R 13 is H or C 1 -C 24 -alkyl, preferably C 6 -C 24 -alkyl, more preferably C 6 -C 24 -alkyl, in particular C 8 -C 20 -alkyl, especially C 10 -C 20 -alkyl, very particularly C 10 -C 20 -franched alkyl.
  • the agrochemical composition comprises pesticide and UV absorber, wherein the UV absorber of a structure of formula IV
  • n 3 to 50, preferably 3 to 25;
  • R 14 , R 15 independently of one another are H or C 1 -C 18 -alkoxy, preferably H or methoxy, in particular H;
  • R 16 H or C 1 -C 24 -alkyl, preferably C 1 -C 4 -alkyl, more preferably CH 3.
  • R 16 is H or C 1 -C 24 -alkyl, preferably C 6 -C 24 -alkyl, particularly preferably C 6 -C 24 -alkyl, in particular C 8 -C 20 -alkyl, especially C 10 -C 20 -alkyl, very particularly C 10 -C 20-branched alkyl.
  • the agrochemical composition comprises pesticide and UV absorber, wherein the UV absorber of a structure of the
  • n is 3 to 50, preferably 3 to 25;
  • R 17 , R 18 independently of one another are H or C 1 -C 18 -alkoxy, preferably H or methoxy, in particular H.
  • the agrochemical composition comprises pesticide and UV absorber, wherein the UV absorber of a structure of formula VI
  • n is 3 to 50, preferably 3 to 20, in particular 3 to 10;
  • R 19 C 1 -C 8 -alkylene, preferably C 1 -C 4 -alkylene, in particular CH 2 ;
  • R 20 H or CrC 24 alkyl, preferably CH 3 ;
  • R 21 H, C 1 -C 18 alkyl, OH or C 1 -C 18 alkoxy, preferably H.
  • R 20 is H or C 1 -C 24 -alkyl, preferably C 6 -C 24 -alkyl, particularly preferably C 6 -C 24 -alkyl, in particular C 8 -C 20 -alkyl, especially C 10 -C 20 -alkyl, very particularly C 10 -C 20 -franched alkyl.
  • the agrochemical composition comprises pesticide and UV absorber, wherein the UV absorber of a structure of formula VII
  • n is from 3 to 50, preferably from 3 to 25, in particular from 3 to 10;
  • R 22 H or C1-C24 alkyl, preferably CH 3;
  • R 23 H or C 1 -C 12 alkyl, preferably H.
  • R 22 is H or C 1 -C 24 -alkyl, preferably C 6 -C 24 -alkyl, more preferably C 6 -C 24 -alkyl, in particular C 8 -C 20 -alkyl, especially C 10 -C 20 -alkyl, very particularly C 10 -C 20 -franched alkyl ,
  • the agrochemical composition according to the invention generally comprises 0.01 to 95% by weight, preferably 0.5 to 80% by weight, more preferably 2 to 50% by weight and especially 5 to 20% by weight of pesticide, in each case based on the composition.
  • the UV absorbers generally have a surface tension at the boundary layer of water to air at 25 0 C of at most 50 mN / m, preferably of at most 46 mN / m, particularly preferably at most 44 mN / m, especially at most 40 mN / m on.
  • the agrochemical composition according to the invention generally comprises 0.1 to 50 wt .-%, preferably 0.5 to 30 wt .-%, particularly preferably 1, 0 to 15 wt .-% UV absorber, each based on the composition.
  • the weight ratio of pesticide to UV absorber is usually from 30: 1 to 1: 2, preferably 15: 1 to 2: 1, more preferably 8: 1 to 3: 1.
  • Agrochemical composition comprising pesticide and UV absorber may be present in common for agrochemical formulations composition types, eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules. The type depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • composition types are suspensions (SC, OD, FS), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), either in water may be soluble or dispersible, and gels for the treatment of plant propagation materials such as seed (GF).
  • Baits for animals, such as ants or rats may be of various of the aforementioned types of composition, preferably as powders, pastes, granules or gels.
  • the composition types eg SC, OD, FS, WG, SG, WP, SP, SS, WS, GF
  • Composition types such as DP, DS, GR, FG, GG, MG or bait are generally used undiluted.
  • Preferred types of compositions are suspensions.
  • auxiliaries customary for crop protection agents, the choice of auxiliaries being based on the specific application form or the active substance.
  • suitable auxiliaries are solvents, solid carriers, surface-active substances (such as further solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment) or customary Aid for bait formulation (eg attractants, feeds, bitter substances).
  • Suitable solvents include water, organic solvents such as medium to high boiling point mineral oil fractions such as kerosene and diesel oil, coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
  • solvent mixtures and mixtures of the abovementioned solvents and water can also be used.
  • Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • surfactants as surfactants (adjuvants, wetting agents, adhesives, dispersants or emulsifiers) are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg.
  • lignin 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, 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 of naphthalenesulfonic acids with Phenol and formaldehyde, polyoxyethyl tocylphenol ethers, ethoxylated isooctyl, octyl or nony
  • 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, U.S.A.), Rhodopol ® 23 (Rho dia, France) or Veegum ® (RT Vanderbilt, USA) or attaclay ® (Engelhard Corp., NJ, USA).
  • Bactericides may be added to stabilize the composition.
  • bactericides are those based on diclorophene and Benzylalkoholhemi- formal (Proxel ® Fa. ICI or Acticide ® RS Fa. Thor Chemie and Kathon ® MK Fa. Rohm & Haas) and isothiazolinone derivatives such as Alkylisothiazolinonen and Benzisothiazolinonen (Acticide ® MBS of Fa. 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.
  • composition types are:
  • compositions for dilution in water i) Water-soluble concentrates (SL, LS)
  • emulsions 15 parts by weight of the pesticide are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the composition has 15% by weight active ingredient content, iv) emulsions (EW, EO, ES)
  • the pesticide 25 parts by weight of the pesticide are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added by means of an emulsifying machine (eg Ultra-Turrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the composition has an active ingredient content of 25 wt .-%. v) suspensions (SC, OD, FS)
  • composition has one
  • the compounds may be used as such or in the form of their compositions, e.g. B. in the form of directly sprayable solutions, powders, suspensions, dispersions, e-mulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, misting, dusting, scattering, laying bait, painting, dipping or pouring.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. 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. In the treatment of plant propagation materials, eg. B. State, are generally used amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of propagating material or seed. When used in material or storage protection, the application rate depends on the substance according to the type of field of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • the present invention further relates to UV absorbers of the aforementioned formula I, wherein AO is CH 2 CH 2 NH when both R 2 and R 3 are H.
  • UV stands for a radical radical selected from the structures of the formulas B and C.
  • AO is CH 2 CH 2 NH.
  • the invention relates to a UV absorber, wherein the UV absorber of a structure of formula IX
  • n 3 to 50, preferably 3 to 25; and R 10 , R 11 , R 12 and R 13 are as defined above.
  • the invention relates to a UV absorber, wherein the UV absorber of a structure of the formula X.
  • n 3 to 50, preferably 3 to 25; and R 14 , R 15 and R 16 are as defined above.
  • the invention relates to a UV absorber, wherein the UV absorber of a structure of the formula XI
  • n 3 to 50, preferably 3 to 25; and R 17 and R 18 are as defined above.
  • the invention relates to a UV absorber, wherein the UV absorber of a structure of the formula XII where n is from 3 to 50, preferably from 3 to 25, in particular from 3 to 10; and R 19 , R 20 and R 21 are as defined above.
  • the invention relates to a UV absorber, wherein the UV absorber of a structure of the formula XIII
  • n is from 3 to 50, preferably from 3 to 25, in particular from 3 to 10; and R 22 and R 23 w are each defined above.
  • the UV absorbers according to the invention usually have a surface tension at the boundary layer of water to air at 25 ° C. of at most 50 mN / m, preferably at most 46 mN / m, particularly preferably at most 44 mN / m, especially at most 40 mN / m ,
  • the present invention furthermore relates to a use of the UV absorbers according to the invention in agrochemical compositions.
  • the use is preferred for use in agrochemical compositions.
  • Particularly preferred is the use for stabilizing UV-sensitive pesticides, especially against sunlight.
  • Preferred UV absorbers are those of the formulas III to XIV, in particular of the formulas IX to XIII. Suitable agrochemical compositions are as described above.
  • the present invention further 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, wherein the composition according to the invention on the respective pests, their habitat or the plants to be protected from the respective pest, the soil and / or undesirable plants and / or the crops and / or their habitat.
  • UV absorbers are readily soluble in agrochemical formulations, or highly compatible with agrochemical formulations such as aqueous emulsions and aqueous Sus pensions. For example, no additional emulsifier is necessary to incorporate the UV absorbers in the formulation.
  • Pluriol® A350E polyalkoxylene glycol monomethyl ether, OH number about 160 mg KOH / g, molecular weight about 350 g / mol, determined by means of OH number, commercially available as Pluriol® A350E from BASF.
  • Pluriol® A500E methyl polyethylene glycol, OH number about 110 mg KOH / g, molecular weight about 500 g / mol, determined by means of OH number, commercially available as Pluriol® A500E from BASF SE.
  • Pluriol® A500PE Butylpolyethylene glycol / propylene glycol copolymer, OH number about 15 mg KOH / g, molecular weight about 500 g / mol, determined by means of OH number, commercially available as Pluriol® A500PE from BASF SE.
  • Pluronic® 10500 poly (ethylene glycol-block-propylene glycol-block-ethylene glycol), having a propylene glycol block with a molar mass of 3250 g / mol and a total molecular weight of 6500 g / mol (commercially available as Pluronic® PE 10500 from BASF SE).
  • Wettol D1 sodium salt of a condensation product of phenol sulfonic acid
  • Urea-formaldehyde (commercially available as Wettol® D1 from BASF SE).
  • Bactericidal Aqueous mixture of 2.5% by weight of 2-methyl-4-isothiazolin-3-one (MIT) and 2.5% by weight of 1,2-benzisothiazolin-3-one (BIT) (commercially available as active ingredient).
  • MIT 2-methyl-4-isothiazolin-3-one
  • BIT 1,2-benzisothiazolin-3-one
  • Antifoam silicone-based, active content 20% by weight (commercially available as silicone SRE-PFL from Wacker)
  • Xanthan granular xanthan gum, 14% by weight water content, viscosity 2000 mPas as 0.3% by weight solution according to Brookfield (commercially available as Rhodopol ® G from Rhodia).
  • Lupasol® FG A polyethyleneimine having a molecular weight of about 800 g / mol (determined by light scattering), a ratio of primary to secondary to tertiary amine groups of 1 to 0.82 to 0.53 and water content of less than 2% by weight, commercial available as Lupasol® FG from BASF SE.
  • iso-tridekanol N A branched, aliphatic and primary C13 alcohol obtained by trimerization of butene and subsequent hydroformylation and hydrogenation (commercially available as Tridecanol® N from BASF SE).
  • Tinuvin® 384-2 A commercially available from CIBA AG UV absorber from the class of hydroxyphenylbenzotriazoles (95% benzene propenoic acid, 3- (2H-benzotriazol-2-yl) -5- (1, 1-dimethylethyl) -4-hydroxy , C7-9-alkyl esters and 5% 1
  • Uvinul® 3035 commercially available as BASF SE.
  • Uvinul® P25 p-aminobenzoic acid ethoxylate (45) (molecular weight about 1265 g / mol, the sum of x + y + z is about 25) is a commercially available product with
  • the solution was added to the flash column and eluted with methylene chloride, the starting material (4) and then with methanol, the product (27) from the column.
  • iso-tridekanol 160 g, 0.8 mol
  • KOH 2 g, 0.036 mol
  • ethylene oxide (634 g, 14.4 mol) is metered in up to a maximum pressure of 6 bar and, after the addition has ended, the mixture is stirred for a further 3 h.
  • the compound is mixed with synthetic magnesium silicate (3% by weight) and filtered.
  • the tridecyl octa decaoxyethylene glycol (13) (794 g, OH number 69 mg KOH / g) is obtained.
  • the solution was added to the flash column and eluted with methylene chloride, the starting material (9) and then with methanol, the product (34) from the column.
  • Example 4B Synthesis of 2,4,6-trianilino-p- (carboxy- [pluriol A500E] -yl) -1,3,5-triazine (361
  • Example 6B Synthesis of cinnamic acid 3,6,9,12-tetraoxatridecyl ester (44):
  • a formulation containing 100 g / l metaflumizone and 40 g / l UV absorber was prepared by two different methods: a) wet grinding with subsequent addition of UV absorber as in Example 9. b) wet grinding with UV absorber as in Example 8.
  • Example 8 Stability of suspension concentrate - wet grinding with UV absorber
  • the suspension concentrates A1 to A6 and C1 were prepared by wet grinding (1 h, at 3000 rev / min, Dispermat) of the components listed in Table 2 and 105 g of metaflumizone (95% by weight of purity) and 70 g of 1, 2 propylene glycol.
  • 20 g of Wettol D1, 5.0 g of defoamer, 3.0 g of xanthan, and 2.0 g of bactericide were added to these suspensions and made up to 1.0 L with water. After storage at 54 ° C. for two weeks, no change in particle size and particle distribution was found.
  • a sample of all experiments was diluted in each case with CIPAC water D (containing 342 ppm Ca / Mg ions) to a 0.1 and 1 wt.% Suspension. Virtually no sediment was found after 6 hours
  • Example 9 Stability of Suspension Concentrate - Subsequent Addition of UV Absorber
  • the suspension concentrates A7 to A17 were prepared by wet milling (1 h, at 3000 rpm, Dispermat) 105 g of metaflumizone (95% by weight purity), 70 g of 1, 2 propylene glycol and 11 g of Pluronic 10500.
  • a homogeneous, stable suspension was obtained in which at least 90% of the solid particles had a particle size of less than 5 ⁇ m and D (4; 3) was 1.0 ⁇ m.
  • Example 10 Stability of Suspension Concentrate - Subsequent Addition of UV Absorber
  • the suspension concentrates A21 to A31 were prepared as in Example 10, except that the concentration of Pluronic 10500 was 222 g / l and UV absorber was 80 g / l (Table 4). After storage at 54 ° C. for two weeks, no change in particle size and particle distribution was found.
  • Example 1 Test of UV stability of alphacypermethrin
  • UV absorber A solution of 20 mg of alphacypermethrin and 5 or 10 mg (ie, 25 and 50% by weight, respectively, of active ingredient) UV absorber in acetone was prepared. Some drops were on a glass plate, allowed to dry for one hour and then irradiated for 24 h with UVA / IS light of wavelength 300 to 800 nm. Subsequently, the irradiated mixture was dissolved in tetrahydrofuran and the content of alphacypermethrin (ie recovery) determined by HPLC chromatography. As a comparison, an identical sample was examined, which was stored for 24 h in darkness. The experiment shows that the UV absorbers significantly increase the stability of UV-sensitive drugs such as alphacypermethrin (Table 5).
  • the plants (Lima beans, Phaseolus lunatus) were irradiated at 26 0 C in a growth chamber constantly for 24 h per day with UV light.
  • the irradiation intensity in the UV range between 300 and 400 nm was measured and was 39 watt / m 2 .
  • the plants were treated in the two-leaf stage with an aqueous spray mixture containing the suspension concentrates (SC) A7 to A31 or C1 from Examples 9-11 with an application rate of 10 g / ha metaflumizone.
  • DAT days after treatment
  • the remaining active substance activity was determined with a bioassay on larvae of Spodoptera eridania (southern armyworm). For this, the larvae were brought into contact with the plants and mortality was determined three days later (Table 6).
  • the experiment demonstrates that the insecticide in formulations containing the tested UV absorbers is more stable to UV light than in formulations without UV absorbers.
  • the surface tension (OFS) of the UV absorbers was determined at 25 ° C. at concentrations of the UV absorber of about 1 mg / L to 5000 mg / L.
  • the OFS from water to air is for comparison at 72.4 mN / m, the OFS of commercial surfactants at about 30-35 mN / m.
  • Table 7 show that the UV absorbers according to the invention can significantly reduce the surface tension, ie that they are surface-active.

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

Abstract

L'invention concerne une composition agrochimique qui comprend un pesticide et un absorbeur d'UV, ainsi que les absorbeurs d'UV mentionnés. L'invention concerne également l'utilisation des absorbeurs d'UV dans des compositions agrochimiques. L'invention concerne en outre un procédé pour lutter contre des champignons phytopathogènes, les mauvaises herbes et/ou l'attaque des plantes par des insectes ou des acariens et/ou pour réguler la croissance des plantes.
EP09795363A 2008-12-03 2009-11-30 Composition agrochimique comprenant un pesticide et un absorbeur d'uv Withdrawn EP2373158A2 (fr)

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KR (1) KR20110099712A (fr)
CN (1) CN102300455A (fr)
AR (1) AR075659A1 (fr)
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US8404263B2 (en) * 2008-06-20 2013-03-26 Basf Se Agrochemical formulations comprising a pesticide, an organic UV-photoprotective filter and coated metal-oxide nanoparticles
WO2010130752A2 (fr) 2009-05-15 2010-11-18 Basf Se Benzotriazoles apolaires de haut poids moléculaire
US9125411B2 (en) 2010-04-15 2015-09-08 Basf Se UV absorbers for reducing the E/Z isomerization of pesticides
BR112013023786B1 (pt) * 2011-03-23 2019-04-30 Basf Se Processo para a preparação de derivados de s-triazina
WO2017157678A1 (fr) * 2016-03-17 2017-09-21 Basf Se Photodégradation réduite par dissolution conjointe de pyraclostrobine et d'absorbeur uv
EP3681291A1 (fr) * 2017-09-13 2020-07-22 Basf Se Nouvelles formulations agrochimiques
JP7664494B1 (ja) * 2023-09-12 2025-04-17 ロート製薬株式会社 新規トリアジン誘導体及びその塩、ならびに、それを用いた紫外線吸収剤、皮膚外用剤、及び、コーティング用組成物

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Publication number Priority date Publication date Assignee Title
WO1997015187A1 (fr) * 1995-10-25 1997-05-01 Abbott Laboratories Compositions pesticides protegees contre les rayons ultraviolets

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DE1914059A1 (de) * 1969-03-20 1970-10-01 Bayer Ag UV-Absorber
US4259189A (en) * 1978-01-19 1981-03-31 Exxon Research And Engineering Co. Novel liquid membrane formulations
DE58909558D1 (de) * 1988-12-28 1996-02-15 Ciba Geigy Ag Schädlingsbekämpfung
JPH04198148A (ja) * 1990-11-28 1992-07-17 Ipposha Oil Ind Co Ltd ２―ヒドロキシベンゾフェノン―４―オキシアルキレンエーテルの製造方法
DE19528529A1 (de) * 1995-08-03 1997-02-06 Bayer Ag Schädlingsbekämpfungsmittel
FR2819179B1 (fr) * 2001-01-11 2003-02-21 Oreal Compositions photoprotectrices a base de polymeres amphiphiles

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997015187A1 (fr) * 1995-10-25 1997-05-01 Abbott Laboratories Compositions pesticides protegees contre les rayons ultraviolets

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JP2012510492A (ja) 2012-05-10
AR075659A1 (es) 2011-04-20
CN102300455A (zh) 2011-12-28
US20110237665A1 (en) 2011-09-29
WO2010063657A3 (fr) 2010-09-16
KR20110099712A (ko) 2011-09-08
BRPI0917062A2 (pt) 2015-07-28

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