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EP2405743A1 - Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol - Google Patents

Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol

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Publication number
EP2405743A1
EP2405743A1 EP10707532A EP10707532A EP2405743A1 EP 2405743 A1 EP2405743 A1 EP 2405743A1 EP 10707532 A EP10707532 A EP 10707532A EP 10707532 A EP10707532 A EP 10707532A EP 2405743 A1 EP2405743 A1 EP 2405743A1
Authority
EP
European Patent Office
Prior art keywords
pesticide
absorber
weight
absorbers
composition
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Withdrawn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
EP10707532A
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 EP2405743A1 publication Critical patent/EP2405743A1/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Withdrawn legal-status Critical Current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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2

Definitions

  • composition comprising pesticide and benzotriazole UV absorber
  • the present invention relates to an agrochemical composition comprising pesticide and UV absorber. Furthermore, the invention relates to UV absorbers and their use in agrochemical compositions. In addition, it relates to a method for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or M ubenfall and / or to regulate 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 agents for controlling harmful insects comprising a substance that modifies the behavior of the pests 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. As UV absorber, for example Tinuvin 1 130 can be occupied.
  • WO 2008/085682 discloses a composition comprising photolabile pesticide and a UV protecting agent, which may be, for example, a benzotriazole or its derivative.
  • UV absorbers from the class of benzotriazoles are known:
  • EP 0 280 650 discloses benzotriazoles of the following structure, wherein R can be, for example, -OCH 2 CH 2 OCH 2 CH 2 OC 2 H 5 or -NHCH 2 CH 2 OC 2 H 5 .
  • Ciba benzotriazoles of the following structure are commercially available.
  • Alkyl stands for a mixture of branched and linear C7-9 alkyl groups.
  • Tinuvin® R796, Ciba benzotriazoles of the following structure (CAS No. 96478-09-0) are commercially available.
  • the UV absorbers in particular from the class of benzotriazoles, from 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 from the class of benzotriazoles for use in agrochemical compositions put. Another object was to find benzotriazole UV absorbers that stabilize UV-sensitive pesticides. The stabilization should be better than in the prior art, especially at lower concentrations of benzotriazole UV absorber. It is also an object to find a benzotriazole UV absorber which has increased interfacial activity and can lower the surface tension of water more. It was another object to find benzotriazole UV absorbers which allow for easier formulation of pesticides, for example by requiring less adjuvants such as surfactants.
  • R 1 - [C 2 -C 4 alkoxy] n - (C 1 -C 18 alkyl) or - [CH 2 CH 2 NH] n -H; R 2 : H or Cl;
  • R 3 is H or C 1 -C 8 -alkyl; and n: 3 to 50, corresponds.
  • Suitable UV absorbers are the structures of the formula I as defined above.
  • Suitable radicals R 1 are - [C 2 -C 4 alkoxy] n - (Ci-Ci 8 alkyl) or - [CH 2 CH 2 NH] n -H, preferably - [C 2 -C 4 alkoxy] n - (Ci -Ci 8 alkyl) and more preferably - [CH 2 CH 2 O] n -CH 3 .
  • C 2 -C 4 alkoxy preferably stands for -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.
  • Mixtures of -CH 2 CH 2 O-, -CH (CH 3 ) CH 2 O- or -CH (CH 2 CH 3 ) CH 2 O- are likewise possible, the alkoxy units being determined in random Or mixtures thereof, preferably as blocks, Preference is given to mixtures of -CH 2 CH 2 O- and -CH (CH 3 ) CH 2 O-, in particular mixtures of -CH 2 CH 2 O- and -CH (CH 3 ) CH 2 O, which occur as blocks.
  • C 1 -C 18 alkyl usually denotes a linear or branched, preferably linear, alkyl group having 1 to 18 carbon atoms
  • the alkyl group is linear and contains 1 to 8, more preferably 1 to 4 and in particular one carbon atom
  • the alkyl group is branched and contains 3 to 18, preferably 6 to 18, more preferably 9 to 15, and especially 10 to 13 carbon atoms.
  • -CH 2 CH 2 NH- is a general empirical formula and represents a monomer unit of the polyethyleneimine group [CH 2 CH 2 NH] n .
  • These polyethyleneimine groups may be linear or branched, preferably they are branched primary, secondary and tertiary amino groups may be in the range of 1 / 0.5 / 0.2 to 1/1, 9 / 1.5, preferably in the range of 1 / 0.7 / 0.4 to 1/1, 5/1, 1.
  • n stands for 3 to 50, preferably 3 to 30, in particular 3 to 25 and especially 3 to 15. In a further preferred embodiment, n is at least 10 to 50, preferably 10.3 to 30, particularly preferably 10.5 to 25, and especially 1 1 to 20.
  • Suitable radicals X are NH or O, preferably O.
  • X is NH or O
  • R 1 is - [CH 2 CH 2 NH] n -H.
  • R 2 is usually H or Cl, preferably H.
  • R3 is usually H or Ci-Cs-alkyl, preferably Ci-Cs-alkyl, particularly preferably a branched Ci-Cs-alkyl, and especially tert-butyl.
  • the UV absorber corresponds to the formula II
  • C 1 -C 4 -alkyl usually stands for a linear or branched, preferably linear, alkyl group and preferably contains 1 to 4, more preferably 1 to 2 and in particular one carbon atom.
  • the UV absorbers usually have a surface tension (OFS) 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 up.
  • the OFS is usually at least 25 mN / m, preferably at least 30 mN / m.
  • 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.
  • 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 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,
  • 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 pesticides are pyrethroids or metaflumizone, especially pyrethroids. Particularly preferred pesticides are alphacypermethrin and metaflu
  • 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 pesticidal film obtained by drying a 25% strength by weight 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 0 C to at least 20 wt.% Degraded. Usually, an illuminance of 10,000 to 100,000 lux, preferably 50,000 to 80,000 lux, is used. 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.
  • 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 weight ratio of pesticide to UV absorber is usually from 30: 1 to 1: 3, preferably 15: 1 to 1: 2, particularly preferably 8: 1 to 1: 1.
  • Agrochemical composition comprising pesticide and UV absorber may be present in common for agrochemical formulations composition types, eg. B. 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), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or Granules (GR, FG, GG, MG), which may either be soluble or dispersible in water, and gels for the treatment of plant propagating materials, such as seeds (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.
  • composition types eg SC, EC 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 Bactericides, antifreeze agents, defoamers, optionally dyes and adhesives (eg for seed treatment) or conventional bait formulation aids (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 soils 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 the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B.
  • 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 dichlorophen and benzyl alcohol formal and isothiazolinone derivatives such as alkylisothiazolinones and Benzisothiazolino- nen (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.
  • composition types are: 1. Compositions for dilution in water i) Water-soluble concentrates (SL, LS)
  • the pesticide 50 parts by weight of the pesticide are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the composition has an active substance content of 50% by weight. vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS)
  • 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 for the preparation of emulsions, pastes or oil dispersions, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. 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 of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg in material protection, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated.
  • the present invention further relates to UV absorbers of formula III
  • Y is NH or O and R 2 , R 3 , n, m and the term "[CH 2 CH 2 NH] n -H" are as defined above In a preferred embodiment, Y is NH.
  • the UV absorbers of the formula III according to the invention usually 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, more preferably at most 44 mN / m, especially at most 40 mN / m on.
  • the OFS is usually at least 25 mN / m, preferably at least 30 mN / m.
  • the present invention furthermore relates to a use of the UV absorbers of the formula III 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.
  • 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 unwanted insect or M ubenfall and / or to regulate the growth of plants, wherein the composition of the invention to 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.
  • Advantages of the present invention is that they stabilize UV-sensitive pesticides, especially at low concentrations of UV absorbers. Another advantage is that less surfactants need to be used in order to obtain a high stability of active substance dispersions, in particular active substance suspensions.
  • the UV absorbers according to the invention can reduce the surface tension of water more strongly, ie that they exhibit a higher interfacial activity.
  • the UV absorbers are readily soluble in agrochemical formulations, or highly compatible with agrochemical formulations, such as aqueous emulsions and aqueous suspensions. For example, no additional emulsifier is necessary to incorporate the UV absorber in the formulation.
  • the following examples illustrate the invention without limiting it.
  • Pluriol® A350E polyalkoxylene glycol monomethyl ether, OH number approx. 160 mg KOH / g,
  • Pluriol® A350E methyl polyethylene glycol, OH number about 1 10 mg KOH / g, molecular weight about 500 g / mol, determined by OH number, commercially available as Pluriol® A500E from BASF SE.
  • Pluronic® 10500 poly (ethylene glycol-block-propylene glycol-block-ethylene glycol), having a propylene glycol block of molar mass 3250 g / mol and a total molecular weight of 6500 g / mol (commercially available as Pluronic® PE
  • MIT 2-methyl-4-isothiazolin-3-one
  • BIT 1,2-benzisothiazolin-3-one
  • Defoamer 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 Brookfield solution (commercially available as Rhodopol® G from Rhodia).
  • Alverde® Water based suspension concentrate of Metaflumizone containing
  • Lupasol® FG A polyethyleneimine having an average molecular weight of about 800 g / mol (as determined by GPC), a ratio of primary to secondary to amine tertiary groups of about 1 to 0.9 to 0.5, and water content of about 1 wt. %, commercially available as Lupasol® FG from BASF SE.
  • Tinuvin® 384-2 A UV absorber commercially available from CIBA AG from the class of hydroxyphenylbenzotriazoles (95% benzene propenoic acid, 3- (2H-benzotriazol-2-yl) -5- (1, 1-dimethylethyl) -4 -hydroxy, C7-9-alkyl ester and 5% 1-methoxy-2-propyl acetate).
  • Tinuvin® 109 A commercially available from CIBA AG UV absorber from the class of hydroxyphenylbenzotriazoles (mixture of 45-55 wt.% Of 3- (5-chloro-2H-benzotriazol-2-yl) -5- (1, 1 dimethyl-4-hydroxy-phenylpropanoic acid octoate and 45-55% by weight of 3- (5-chloro-2H-benzotriazol-2-yl) -5- (1, 1-dimethyl-ethyl) -4-hydroxy- phenylpropanklathylhexyl.
  • 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 called Uvinul® P25 from BASF SE.
  • Example 1 C Synthesis of 3- (3-benzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl) -propionic acid [Pluriol A350E] ester (5)
  • the solution was added to the flash column and eluted with toluene, the starting material (3) and then with methanol, the product (5) from the column.
  • Example 1 D Synthesis of 3- (3-benzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl) -propionic acid [Pluriol A500E] ester (7)
  • the solution was added to the flash column and eluted with a mixture of toluene and ethyl acetate (15: 2% by volume), the starting material (3) and then with methanol, the product (7) from the column.
  • Example 1 F Synthesis of 3- (3-benzotriazol-2-yl-5-tert-butyl-4-hydroxy-phenyl) -propionic acid [tridekanol-EOi8] ester (1 l)
  • the solution was added to the flash column and the starting material (3) was then eluted with ethyl acetate and then the product (10) was eluted from the column with methanol.
  • Example 1 G Synthesis of 2- (5-chloro-2H-benzotriazol-2-yl) -6-tert-butyl-4-hydroxyphenyl-propionic acid (13)
  • the solution was added to the flash column and eluted with methylene chloride, the starting material (14) and then with methanol, the product (15) from the column.
  • Example 1 K Synthesis of 3- (3-benzotriazol-2-yl-5-tert-butyl-4-hydroxyphenyl) propionic acid -Lupasol FG amide (17):
  • Example 2 Stability of Suspension Concentrate The suspension concentrates A18 and A19 were prepared by wet milling (1 h, at 3000 rpm, dispermat) 105 g of metaflumizone (95 wt% purity), 70 g of 1, 2-propylene glycol and Pluronic® 10500 ( Quantity see Table 1). 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.
  • Suspension concentrates A32 and A33 were prepared as in Example 2, except that the concentration of Pluronic 10500 was 222 g / L and UV absorber was 80 g / L (Table 2).
  • a formulation containing 100 g / l metaflumizone and 40 g / l UV absorber was prepared as described in Example 2. The formulation was diluted with water to give an active ingredient content of 10 g / L (Table 3) or 1 g / L (Table 4).
  • Example 4B UV stabilizing effect A commercial formulation of Metaflumizone (Alverde®) containing 240 g / l of meflafluizone was diluted with water to give an active ingredient content of 10 g / l. Various UV absorbers were added (Table 5) and analyzed as described under Example 4A. The results are summarized in 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) A17 to A33 or C1 from Examples 2-3 at 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 3).
  • the surface tension (OFS) of the UV absorbers 1 C and 1 F was determined at 25 ° C. at concentrations of the UV absorber of about 1 mg / L to 5000 mg / L (Table 4).
  • 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.
  • the results show that the UV absorbers according to the invention can significantly reduce the surface tension, ie that they are surface-active. They also show that they can lower the OFS more than commercially available UV absorbers.
  • the UV absorbers according to the invention are similar surface-active as commercial surfactants.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
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  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)

Abstract

La présente invention concerne une composition agrochimique comprenant un pesticide et un absorbeur d'UV. L'invention concerne également un absorbeur d'UV et son utilisation dans des compositions agrochimiques. L'invention concerne en outre un procédé de lutte contre des champignons phytopathogènes et/ou de lutte contre les adventices et/ou de lutte contre les infestations nuisibles par les insectes ou les acariens et/ou de régulation de la croissance de végétaux.
EP10707532A 2009-03-13 2010-03-10 Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol Withdrawn EP2405743A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16012409P 2009-03-13 2009-03-13
PCT/EP2010/053003 WO2010103021A1 (fr) 2009-03-13 2010-03-10 Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol

Publications (1)

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EP2405743A1 true EP2405743A1 (fr) 2012-01-18

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EP10707532A Withdrawn EP2405743A1 (fr) 2009-03-13 2010-03-10 Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol

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US (1) US20120058974A1 (fr)
EP (1) EP2405743A1 (fr)
JP (1) JP2012520259A (fr)
KR (1) KR20110132445A (fr)
CN (1) CN102348378A (fr)
BR (1) BRPI1006352A2 (fr)
WO (1) WO2010103021A1 (fr)

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US9125411B2 (en) 2010-04-15 2015-09-08 Basf Se UV absorbers for reducing the E/Z isomerization of pesticides
US9087991B2 (en) 2011-02-01 2015-07-21 Basf Se Photovoltaic element
JP2013133405A (ja) * 2011-12-26 2013-07-08 Sumitomo Chemical Co Ltd 防虫用樹脂組成物、及びその利用
US9255180B2 (en) 2012-06-28 2016-02-09 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polyethers
US9469725B2 (en) 2012-06-28 2016-10-18 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymers
KR102057874B1 (ko) 2012-06-28 2019-12-20 존슨 앤드 존슨 컨수머 캄파니즈, 인코포레이티드 자외선 방사선-흡수 중합체를 함유하는 썬스크린 조성물
US20150164771A1 (en) 2013-12-18 2015-06-18 Johnson & Johnson Consumer Companies, Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
US10874603B2 (en) 2014-05-12 2020-12-29 Johnson & Johnson Consumer Inc. Sunscreen compositions containing a UV-absorbing polyglycerol and a non-UV-absorbing polyglycerol
WO2017157678A1 (fr) * 2016-03-17 2017-09-21 Basf Se Photodégradation réduite par dissolution conjointe de pyraclostrobine et d'absorbeur uv
US10596087B2 (en) 2016-10-05 2020-03-24 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymer composition
WO2019052898A1 (fr) * 2017-09-13 2019-03-21 Basf Se Nouvelles formulations agrochimiques
US20220017527A1 (en) * 2018-12-06 2022-01-20 Basf Se Novel procedure for the formation of 2h-benzotriazole bodies and congeners
CN110963975A (zh) * 2019-11-18 2020-04-07 南昌航空大学 一种苯并三唑衍生物和制备方法及作为杀菌剂的应用
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Also Published As

Publication number Publication date
WO2010103021A1 (fr) 2010-09-16
KR20110132445A (ko) 2011-12-07
CN102348378A (zh) 2012-02-08
BRPI1006352A2 (pt) 2015-08-25
US20120058974A1 (en) 2012-03-08
JP2012520259A (ja) 2012-09-06

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