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
  • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
  • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
  • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
• • 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
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
• • 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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
  • A01N33/18—Nitro compounds
  • A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
  • A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
• • 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
  • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
  • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
  • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

• the invention is in the field of crop protection agents which can be used against undesired plant growth, in particular the combinations of herbicides.
• Glufosinate-ammonium is mainly used in the post-emergence process to combat weeds and weeds in plantation crops and on non-cultivated land, as well as by means of special application techniques also for inter-row control in agricultural Area crops such as corn, cotton and others used.
• the compound of formula (1) contains an asymmetric carbon atom.
• the L enantiomer is considered the biologically active isomer.
• glufosinate ammonium as well as that of its L-enantiomer can be significantly improved by surface-active substances, preferably by wetting agents from the series of alkyl polyglycol ether sulfates, for example in the form of their alkali metal or Ammonium salts, but also used as a magnesium salt, such as C 2 / C 14 - fatty alcohol diglycol ether sulfate sodium ( ® Genapol LRO, Hoechst); see EP-A-0476555, EP-A-0048436, EP-A-03361 51 or US-A-4,400, 196 and Proc. EWRS Symp.
• wetting agents from the series of alkyl polyglycol ether sulfates, for example in the form of their alkali metal or Ammonium salts, but also used as a magnesium salt, such as C 2 / C 14 - fatty alcohol diglycol ether sulfate sodium ( ® Genapol LRO, Hoechst);
• alkyl polyglycol ether sulfates are also suitable as penetration aids and activity enhancers for a number of other herbicides, including herbicides of the diphenyl ether type; see EP-A-0476555.
• glufosinate-ammonium or related active ingredients can be advantageously combined as penetration aids together with certain herbicides of the nitrodiphenyl ether type and anionic surfactants from the series of alkyl polyglycol ether sulfates and result in synergistic increases in activity.
• the invention thus relates to herbicidal compositions, characterized by an effective content of a combination of
• Z is a radical of the formula -OM, -NHCH (CH 3 ) CONHCH (CH 3 ) COOM or
• Formula (A) includes all stereoisomers and their mixtures, in particular the racemate and the biologically active enantiomer.
• Bialaphos or Bilanafos
• oxyfluorfen i.e. 2-chloro-1 - (3-ethoxy-4-nitro-phenoxy) -4-trif ⁇ uormethyl-benzene, the use of which as a single active ingredient with 100-1000 g a.i./ha in soy is known before and after emergence or on non-cultivated land;
• lactofen ie 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitro-benzoic acid 1 - (ethoxycarbonyl) ethyl ester; the active ingredient is usually used alone with 50 - 500 g ai / ha pre- and post-emergence in soybeans and cereals; b3) bifenox, ie methyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate; the active ingredient is usually used alone with an application rate of 50 to 1000 g ai / ha before and after emergence in cereals, rice and corn;
• fluoroglycofen-ethyl i.e. 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoic acid ethoxycarbonylmethyl ester; it is known to be used as a single active ingredient at a rate of 5 to 50 g ai / ha in the pre- and post-emergence in cereals and soybeans;
• Fomesafen i.e. N-methylsulfonyl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzamide; it is known to be used as a single active ingredient with 50 to 1000 g ai / ha pre- and post-emergence in soy or cereals.
• connections b1 to b6 are e.g. B. in "The Pesticide Manual” 9th Edition, British Crop Protection Council 1 991 and literature cited therein and known as herbicides of the protoporphyrinogen oxidase inhibitor type.
• the anionic surfactant (C) is, for example, a wetting agent from the group of the fatty alcohol polyglycol ether sulfates and their salts, preferably the C 10 -C 18 fatty alcohol polyglycol ether sulfates in the form of the alkali metal, alkaline earth metal or ammonium salts or the substituted ammonium salts;
• Substituted ammonium salts are, for example, primary, secondary, tertiary and quaternary ammonium salts with substituents from the group alkyl or hydroxyalkyl, preferably with 1 to 4 carbon atoms.
• C is preferably 1 2 -C 14 -fatty alcohol diethylenglykolethersulfat sodium salt (Genapol ® LRO, Hoechst AG).
• Genapol ® LRO diethylenglykolethersulfat sodium salt
• Biological examples of combinations of the herbicides are missing in US Pat. No. 5,324,708, as are indications of synergistic increases in activity for combinations of glufosinate-ammonium and oxyfluorfen.
• Research Disclosure 275 (1987), 1 54 discloses combining the activity spectrum of glufosinate ammonium with other herbicides to supplement the spectrum of action.
• the combination of glufosinate ammonium and oxyfluorfen for use in cotton is mentioned. There are no indications of synergistic increases in effectiveness for the combination of glufosinate ammonium and oxyfluorfen or for combinations with fatty alcohol polyglycol ether sulfates.
• the weight ratios A: B of the combined herbicides of type A and type B can therefore vary within wide limits and are generally between 100: 1 and 1: 5, preferably between 10: 1 and 1: 1.
• the following weight ratios A: B are preferred for the combination of type A herbicides, in particular glufosinate-ammonium (racemic): with oxyfluorfen 10: 1 to 2: 1, in particular 8: 1 to 3: 1. with lactofen 10: 1 to 2: 1, especially 8: 1 to 3: 1. with Bifenox 10: 1 to 2: 1, especially 8: 1 to 3: 1. with fluoroglycofen 100: 1 to 10: 1, in particular 50: 1 to 10: 1. with acifluorfen 10: 1 to 2: 1, in particular 8: 1 to 3: 1. with fomesafen 10: 1 to 2: 1, especially 8: 1 to 3: 1.
• the application rate of the respective herbicides in the combined application is substantially below the application rate for the individual application of the respective herbicide with the same herbicidal action.
• application rates of 100 to 600 g a.i./ha herbicide of type A, preferably glufosinate-ammonium, and from 50 to 150 g a.i./ha of nitrodiphenyl ethers such as oxyfluorfen and lactofen are preferred.
• the optimum application rate of the type C anionic surfactant depends on the application rate of the herbicides and is generally between 100 and 2000 g surfactant per hectare, based on the detergent substance (WAS), preferably 500 to 1500 g WAS / Ha.
• the weight ratio of herbicide A to surfactant C is accordingly preferably 1: 1 to 1:10, in particular 1: 2 to 1: 5.
• the agents according to the invention cover a wide range of chewing. They are suitable, for example, to combat annual and perennial Weeds such as Agropyron, Paspalum, Cynodon, Imperata, Pennisetum, Convolvulus, Cirsium, Rumex and others.
• the agents according to the invention can be used for the selective control of annual and perennial harmful plants in plantation crops such as oil palm, coconut palm, rubber tree, citrus, pineapple, cotton, coffee, cocoa and others. as well as in fruit and wine growing.
• the combinations according to the invention can be used in arable farming in the so-called “no till” or "zero tilP” process.
• they can also be used non-selectively on paths, squares, industrial plants, etc., in order to keep these areas free from undesired vegetation.
• the herbicidal compositions according to the invention are notable for a rapid onset and long-lasting herbicidal action.
• the rain resistance of the active substances in the combinations according to the invention is favorable.
• a particular advantage is that the effective doses of compounds of the formula (A) and (B) used in the combinations are so low that their soil effect is considerably reduced. This makes their use not only possible in sensitive crops, but groundwater contamination is practically avoided.
• the combination of active ingredients and wetting agents according to the invention enables a considerable reduction in the amount of active ingredients required.
• the invention therefore also relates to a process for combating undesirable plant growth, characterized in that one or more type A herbicides with one or more type B herbicides and an anionic type C surfactant are applied to the harmful plants, parts of plants thereof or the area under cultivation applied.
• the active compound combinations according to the invention can be present both as mixed formulations of the three components, if appropriate with further customary formulation auxiliaries, which are then used in the usual manner Diluted water can be used, or can be produced as so-called tank mixes by jointly diluting the separately formulated or partially separately formulated components with water.
• the compounds of type A and type B or their combinations, optionally together with the surfactant C can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified.
• general formulation options are: wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, Oil- or water-based dispersions, suspoemulsions, dusts (DP), mordants, granules for soil or litter application or water-dispersible granules (WG), ULV formulations, microcapsules or waxes.
• combinations with other pesticidally active substances such as other herbicides, fungicides or insecticides, and safeners, fertilizers and / or growth regulators can also be prepared, e.g. in the form of a finished formulation or as a tank mix.
• Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or also oleoylmethyltauric acid sodium.
• ionic or nonionic surfactants e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates
• Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more ionic or nonionic surfactants (emulsifiers).
• organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
• ionic or nonionic surfactants emulsifiers
• alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate
• nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid ester sorbetyl ester, polyoxyethylene fatty acid sorbetyl ester, polyoxyethylene acid sorboxyl ester, polyoxyethylene acid sorbetyl ester, polyoxyethylene acid sorbetyl ester, polyoxyethylene acid sorbetyl ester, polyoxyethylene acid sorbetyl ester, polyoxyethylene ethoxylate, polyoxyethylene ethoxylate.
• Dusts are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
• Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
• Water-dispersible granules are generally produced using processes such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical preparations generally contain 0.1 to 99 percent by weight, in particular 2 to 95 percent by weight, of active ingredients of types A and / or B, the following concentrations being customary depending on the type of formulation:
• the active substance concentration in wettable powders is e.g. about 10 to 95 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
• the active substance concentration can e.g. 5 to 80
• Dust-like formulations usually contain 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight of active ingredient.
• the active ingredient content depends on
• Granulating agents and fillers can be used.
• the a rule the
• the content of the water-dispersible granules is between 10 and 90
• the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreezes and solvents, fillers, dyes and carriers, defoamers, Evaporation inhibitors and agents that affect pH or viscosity.
• the formulations present in the commercial form are optionally diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
• Preparations in the form of dust, ground granules or granules for spreading, and sprayable solutions are usually no longer diluted with other inert substances before use.
• the active compounds can be applied to the plants, parts of plants, plant seeds or the area under cultivation (arable soil), preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.
• One possible application is the joint application of the active ingredients in the form of tank mixes, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray liquor obtained being applied.
• a common herbicidal formulation of the combination according to the invention of active ingredients A and B and surfactant C has the advantage of being easier to use because the amounts of the components have already been set in the correct ratio to one another.
• the auxiliaries in the formulation can be optimally coordinated with one another, while a tank mix of different formulations can result in undesired combinations of auxiliaries.
• most types of formulation are not suitable for a common formulation.
• Active substances of type A and surfactant C are hydrophilic and are usually formulated as a strongly salt-containing aqueous solution.
• Active ingredients B are largely insoluble in water and are usually formulated as emulsifiable concentrates or granules.
• the invention therefore also relates to a special mixed formulation which does not have the disadvantages mentioned above, and to the use thereof.
• the mixed formulation is an oil-in-water emulsion (EW), characterized by the content of a) 1 to 15% by weight of active ingredient of the type A mentioned
• suitable solvents are non-polar solvents, polar protic or aprotic dipolar solvents and mixtures thereof, the organic solvent forming an emulsified organic phase with the nitrodiphenyl ether herbicide in addition to the aqueous phase which contains the type A herbicide.
• Suitable solvents are aliphatic and aromatic hydrocarbons, such as. B. mineral oils or toluene, xylenes and naphthalene derivatives; halogenated aliphatic and aromatic hydrocarbons, such as methylene chloride or chlorobenzene; Ethers, such as diethyl ether, tetrahydrofuran (THF), dioxane,
• Alkylene glycol monoalkyl ethers and dialkyl ethers such.
• Ketones such as acetone and cyclohexanone
• Nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile
• Sulfoxides and sulfones such as dimethyl sulfoxide (DMSO) and sulfolane;
• Oils e.g. B. plant-based such as corn oil and rapeseed oil.
• alcohols such as the alkanols methanol, ethanol, n- and i-propanol, n-, i-, t- and 2-butanol can often be used.
• Preferred organic solvents are aromatic hydrocarbons, such as. B. toluene, xylenes and naphthalene derivatives.
• Suitable emulsifiers are ionic surfactants and nonionic surfactants, for example as ionic emulsifiers: alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate, phosphated
• Propylene oxide-ethylene oxide condensation products such as phosphated PO-EO
• Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
• Block copolymers alkyl polyethers, polyols such as polyvinyl alcohol,
• Sorbitan fatty acid esters polyoxyethylene sorbitan fatty acid esters or
• Emulsifier mixtures of modified polyvinyl alcohol for example ® Mowiol 3/83, ® Mowiol 4/88; Hoechst
• phosphated PO-EO block copolymer for example Hoe S 361 8, Hoechst
• dodecylbenzenesulfonate calcium and Fatty alcohol polyglycol ether e.g. B. the usual formulation aids already mentioned above; preferred tools are
• Antifreeze and evaporation inhibitors such as glycerin, e.g. B. in one
• Preservatives e.g. B. ® Mergal K9N (Riedel) or ® Cobate C, in the usual application concentrations for the particular used
• Defoamers e.g. B. silicone defoamers such as anti-foam emulsion SRE, in the usual application concentrations.
• Preferred mixed formulations are EW formulations, characterized by a) 5 to 1 2% by weight glufosinate ammonium, b) 1 to 4% by weight nitrodiphenyl ether, c) 5 to 1 2% by weight fatty alcohol polyglycol ether sulfate, d ) 3 to 20% by weight, preferably 3-15% by weight, in particular 5 to 10
• Mixed formulations are preferred which contain 6 to 1 8% by weight of a herbicide combination of glufosinate-ammonium (racemic) and oxyfluorfen or lactofen in a weight ratio A: B of 10: 1 to 2: 1 and 5 to 1 2% by weight C.
• the EW mixed formulations are characterized by good physical and chemical storage stability. The handling of the formulations is simplified compared to that of a tank mix. When using the mixed formulations, biological results are obtained which are comparable to those of one Tank mix from the separately formulated components do not lag behind, but usually surpass them.
• a dusting agent is obtained by mixing 10 parts by weight of an active ingredient combination according to the invention and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
• a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compounds A + B, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium mixes as a wetting and dispersing agent and grinds in a pin mill.
• a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active compounds A + B with 6 parts by weight of alkylphenol polyglycol ether ( ® Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Parts of paraffinic mineral oil (boiling range approx. 255 to 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
• An emulsifiable concentrate is obtained from 1 5 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
• a water-dispersible granulate is obtained by adding 75 parts by weight of active ingredients A + B,
• a water-dispersible granulate is also obtained by
• Polyvinyl alcohol produced by partial saponification of polyvinyl acetate with a viscosity of 3 cP, measured in a 4% strength aqueous solution at 20 ° C., and a degree of hydrolysis of 83 mole percent.
• Polyvinyl alcohol produced by partial saponification of polyvinyl acetate and having a viscosity of 4 cP, measured in a 4% strength aqueous solution at 20 ° C., and a degree of hydrolysis of 88 mole percent.
• Phenylsulfonate CA (Hoechst): C 12 alkyl benzenesulfonate calcium
• Antifoam emulsion SRE (Wacker): antifoam based on silicone oil Biological examples
• Various economically important weeds and grasses are grown under natural outdoor conditions. After certain development stages have been reached (expressed by the number of unfolded leaves or by the height), a tank mix of the respective herbicides with the surfactant C or a tank mix of the herbicide mixtures and the surfactant C are applied under standard conditions, i.e. H. with a plot sprayer with a water application rate of 300-400 liters of water per hectare. In the period of 1 to 3 weeks after application, the herbicidal activity of the active compounds or mixtures of active compounds is visually assessed on the basis of the treated plots in comparison to untreated control plots. Damage and development of all parts of the plant above ground are recorded.
• A1 glufosinate ammonium (rac.)
• C1 C 12 / C 14 fatty alcohol diethylene glycol ether sulfate Na ( ® Genapol LRO)
• ERISP Erigeron sp.

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• Life Sciences & Earth Sciences (AREA)
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• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1995
  • 1995-01-24 DE DE19501986A patent/DE19501986A1/de not_active Withdrawn
• 1996
  • 1996-01-10 KR KR1019970705014A patent/KR19980701620A/ko not_active Application Discontinuation
  • 1996-01-10 CN CN96191578A patent/CN1169099A/zh active Pending
  • 1996-01-10 JP JP8522577A patent/JPH10512575A/ja active Pending
  • 1996-01-10 BR BR9606986A patent/BR9606986A/pt not_active Application Discontinuation
  • 1996-01-10 WO PCT/EP1996/000072 patent/WO1996022692A1/de not_active Application Discontinuation
  • 1996-01-10 EP EP96900574A patent/EP0805627A1/de not_active Ceased
  • 1996-01-10 CZ CZ972278A patent/CZ227897A3/cs unknown
  • 1996-01-10 AU AU44375/96A patent/AU4437596A/en not_active Abandoned
  • 1996-01-10 HU HU9702457A patent/HUP9702457A3/hu unknown
  • 1996-01-10 CA CA002211200A patent/CA2211200A1/en not_active Abandoned
  • 1996-01-23 ZA ZA96502A patent/ZA96502B/xx unknown

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