EP1816914A1 - Procede pour renforcer l'efficacite de l'ethaboxam - Google Patents

Procede pour renforcer l'efficacite de l'ethaboxam

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Publication number
EP1816914A1
EP1816914A1 EP05811186A EP05811186A EP1816914A1 EP 1816914 A1 EP1816914 A1 EP 1816914A1 EP 05811186 A EP05811186 A EP 05811186A EP 05811186 A EP05811186 A EP 05811186A EP 1816914 A1 EP1816914 A1 EP 1816914A1
Authority
EP
European Patent Office
Prior art keywords
ethaboxam
active
methyl
plants
phenyl
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Withdrawn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
EP05811186A
Other languages
German (de)
English (en)
Inventor
Jordi Tormo I Blasco
Maria Scherer
Reinhard Stierl
Siegfried Strathmann
Matthias NIEDENBRÜCK
Horst Dieter Brix
Markus Gewehr
Christine Beck
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
Priority to EP10171025A priority Critical patent/EP2255633A1/fr
Priority to EP09176984A priority patent/EP2206432A3/fr
Priority to EP10171032A priority patent/EP2255635A1/fr
Priority to PL08154087T priority patent/PL1949788T3/pl
Priority to EP10171029A priority patent/EP2255634A1/fr
Priority to EP10171034A priority patent/EP2255636A1/fr
Priority to EP10171018A priority patent/EP2255631A1/fr
Priority to EP10171023A priority patent/EP2255632A1/fr
Priority to EP08154087A priority patent/EP1949788B1/fr
Publication of EP1816914A1 publication Critical patent/EP1816914A1/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Withdrawn legal-status Critical Current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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to a method for enhancing the fungicidal Wirk ⁇ efficiency of
  • the active compound I simultaneously or separately with at least one active compound II from the group: b) dithiocarbamates such as Maneb, Mancozeb, Metam or Metiram, sulfenic acid derivatives such as captan or folpet, strobilurin derivatives such as kresoxim-methyl or pyraclostrobin, cinnamamides and analogues such Dimethomorph or Flumorph, or
  • [1,2,4] triazolo [1,5-a] pyrimidine is administered in synergistically effective amounts by spraying or dusting the seeds, plants or soils before or after sowing the plants or before or after emergence of the plants , where no polyoxyalkylene alkyl ethers are used as adjuvants.
  • the invention relates to novel synergistic mixtures of ethaboxam with active ingredients from group b1) and to compositions containing these mixtures and to the use of compound I with active compounds from group b1) for the preparation of such mixtures.
  • ethaboxam of the formula I, / V- (cyano-2-thienylmethyl) -4-ethyl-2- (ethylamino) -5-thiazolecarboxamide, whose preparation and its action against harmful fungi are described above as component a), are known from the literature ( EP-A 639 574).
  • the active substances mentioned above as component b), their preparation and their action against harmful fungi are likewise generally known (cf. also: http://www.hclrss.demon.co.uk/index.html):
  • Metiram zinc ammonium ethylenebis (dithiocarbamate) (U.S. 3,248,400);
  • Mefenoxam methyl N- (methoxyacetyl) -N- (2,6-xylyl) -D-alaninate (WO 96/01559);
  • Famoxadone (RS) -3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione;
  • Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
  • WO 01/84930 discloses formulations of ethaboxam containing polyoxyalkylene alkyl ethers which, in addition to ethaboxam, may contain a further active compound from group b).
  • the use of the polyoxyalkylene alkyl ethers described increases the fungicidal activity of ethaboxam.
  • the object of the present invention was to increase the fungicidal activity of ethaboxam, irrespective of the use of certain formulation auxiliaries.
  • the mixtures of ethaboxam and at least one active compound from group b) or the simultaneous joint or separate use of ethaboxam and at least one active compound from group b) are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. They can be used in crop protection as foliar, pickling and soil fungicides.
  • the combinations of ethaboxam and at least one active substance of group b) are also suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • Ethaboxam and active ingredients from group b) can be applied simultaneously together or separately or in succession, the sequence in the case of separate application generally having no effect on the control result.
  • Preferred in the process according to the invention are the combinations of ethaboxam with one of the compounds dithianone and dimethomorph.
  • a particularly preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and strobilurins such as kresoxime-methyl or, in particular, pyraclostrobin.
  • a further preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2, 4] triazolo [1,5-a] pyrimidine (Formula 11-1).
  • a further preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and zoxamide. Preference is given to the preparation of the mixtures, the pure active ingredients I and II, which as needed further active ingredients IM against harmful fungi or other pests such as insects, spider animals or nematodes, or herbicidal or wax ⁇ tumsregulierende agents or fertilizers as further active components - able to see.
  • fungicides selected from the following group c) are suitable:
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph,
  • Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prochloroconazole, simeconazole, tebuconazole, tetraconazole , Triadimefon, triadimol, triflumizole, triticonazole,
  • Dicarboximides such as iprodione, myclozoline, vinclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamate, Thiram, Ziram, Zineb,
  • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxaldine, oxycarboxine, cyazofamide, dazomet, dithianone, famoxadone, fenamidone,
  • Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthalic-isopropyl,
  • Phenylpyrroles such as fenpiclonil or fludioxonil
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chloroboronyl, cyflufenamid, cymoxanil, diclomethine, diclocymet, diethofencarb, edfenphos, fenhexamide, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, Iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, protamocarb, phosphorous acid, phthalide, toloclofos-methyl, quintozene, zoxamide,
  • Strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid,
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • mixtures of ethaboxam with an active ingredient II from group b) are used.
  • a particularly strong fungicidal activity exhibits mixtures of ethaboxam with two active compounds II and III.
  • Suitable active compounds II are preferably those mentioned in group b), as further active compounds III, in addition to the active compounds of group b), in particular phosphorous acid H 3 PO 3 , their alkali metal or alkaline earth salts or derivatives releasing them, are preferred Ethylphosphonat (common name: Fosethyl) and ethyl phosphonate aluminum (common name: Fosethyl-Al), or Kupfer ⁇ fungicides such as Bordeaux broth, copper acetate, copper oxychloride or basic copper sulfate in question.
  • a particularly preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and fluazinam with another active ingredient III.
  • Another particularly preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and pyraclostrobin with another active substance III.
  • Another particularly preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and dithianone with another active ingredient III.
  • Another particularly preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam and dimethomorph with another active substance III.
  • Another particularly preferred embodiment of the mixtures according to the invention relates to the combination of ethaboxam with the compound of formula 11-1 and an active compound III from group c).
  • Ethaboxam and the active compound II are usually used in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:50, in particular 10: 1 to 1:20 applied.
  • the combination of ethaboxam with the compound of the formula 11-1 is preferably present in a weight ratio of 20: 1 to 1:20, in particular 10: 1 to 1:10.
  • active compounds III are added to ethaboxam preferably in a ratio of 20: 1 to 1:20.
  • Phosphoric acid and copper fungicides can also be added advantageously in significantly higher amounts.
  • ne- the active compounds 1: 11: 111 preferably in ratios of 100: 1: 2000 to 100: 1: 5 to 1: 100: 0.05 to 1: 100: 20 before.
  • the application rates of the mixtures according to the invention are from 5 g / ha to 2000 g / ha, preferably from 50 to 1750 g / ha, in particular from 50 to 1500 g / ha.
  • the application rates for ethaboxam are generally from 1 to 750 g / ha, preferably from 10 to 500 g / ha, in particular from 20 to 250 g / ha.
  • the application rates for an active ingredient II are generally in accordance with 1 to 2000 g / ha, preferably 10 to 1500 g / ha, in particular 40 to 1200 g / ha.
  • the application rates are usually 5 g / ha to 1000 g / ha, preferably 50 to 900 g / ha, in particular 40 to 750 g / ha.
  • application rates of mixture of 1 to 1000 g / 100 kg of seed preferably 1 to 750 g / 100 kg, in particular 5 to 500 g / 100 kg, are generally used.
  • the method for controlling harmful fungi is carried out by the separate or joint application of ethaboxam and at least one active compound from group b) or the mixtures of ethaboxam and at least one active compound from group b) by spraying or dusting the seeds, the Plants or soils before or after sowing of the plants or before or after emergence of Pflan ⁇ zen, wherein in the case of the active ingredients II, which do not belong to the group b1, no polyoxyalkylenalkylether be used as an adjuvant.
  • the mixtures according to the invention can be converted into the customary formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • customary formulations e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • polyoxyalkylene alkyl ethers are also suitable as adjuvants.
  • the application form depends on the respective intended use; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially: - water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), Acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • Excipients such as ground natural minerals (e.g., kaolins, clays, talc, calks) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • ground natural minerals e.g., kaolins, clays, talc, calks
  • ground synthetic minerals e.g., fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivative
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, for example ammonium sulfate Ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as milled flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers,
  • Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
  • Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
  • suitable binders are EO / PO block copolymer surfactants, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethyleneamines, polyethylene amides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethanes, polyvinyl acetates, Tylose and Copolymers of these polymers.
  • a suitable gelling agent is, for example, carrageenan (Satiagel®).
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredients.
  • the active compounds are employed in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • 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 active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
  • formulations are: 1. Products for dilution in water
  • the active compounds 20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water results in a dispersion.
  • the active ingredient content is 20% by weight.
  • Emulsions EW, EO, ES
  • the active compounds 25 parts by weight of the active compounds 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 introduced by means of an emulsifier (Ultraturax) into 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • Suspensions 20 parts by weight of the active compounds are comminuted to a fine suspension of active substance in an agitating ball mill with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example 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 formulation has an active ingredient content of 50% by weight.
  • the active ingredients 75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content is 75 wt .-%.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • FS formulations for seed treatment Preference is given to using FS formulations for seed treatment.
  • such formulations contain 1 to 800 g / l of active ingredient, 1 to 200 g / l of surfactants, 0 to 200 g / l of antifreeze, 0 to 400 g / l of binder, 0 to 200 g / l of dyes and solvents, preferably water.
  • the active compounds can be used as such, in the form of their formulations or the application forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, Scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water.
  • the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
  • wetter tackifier
  • dispersant or emulsifier it is also possible to prepare from effective substance wetting agents, adhesives, dispersants or emulsifiers and any concentrates which are solvent or oil, 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 active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B. Pluro- nic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
  • organically modified polysiloxanes eg Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluro
  • the compounds I and II or the mixtures or the corresponding formulations are used by mixing the harmful fungi, the plants, seeds, soils, surfaces, materials or spaces to be kept free of them with a fungicidally effective amount of the mixture, or of compounds I and II when separately applied.
  • the application can take place before or after the attack by the harmful fungi.
  • the fungicidal activity of the compound and of the mixtures was demonstrated by the following experiments:
  • the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the active compounds pyraclostrobin, famoxadone, fluazinam and zoxamide were used as commercially available formulations.
  • the efficiency (W) is calculated according to the formula of Abbot as follows:
  • a corresponds to the fungal infestation of the treated plants in% and ß corresponds to the fungal infestation of the untreated (control) plants in%
  • the infestation of the treated plants corresponds to those of the untreated control plants; at an efficiency of 100, the treated plants have no infestation.
  • Leaves of pot fry were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
  • the plants were placed in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous zoospore suspension of Plasmopara viticola. Thereafter, the first vines wur ⁇ for 48 hours in a water vapor-saturated chamber at 24 0 C and then for 5 days in a greenhouse at 20 to 30 0 C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak. Then, the extent of the infestation development on the leaf undersides was visually determined.
  • Leaves of potted vines were sprayed to drip point with aqueous suspension in the active ingredient concentration given below.
  • the plants were set up to dry the spray coating for 3 days in the greenhouse.
  • the leaves were then inoculated with an aqueous zoospore suspension of Plasmopara viticola.
  • the vines were first set up for 48 hours in a water vapor-saturated chamber at 24 ° C and then for 5 days in the greenhouse at temperatures between 20 and 3O 0 C. After this time, the plants were again placed in a moist chamber for 16 hours to accelerate the sporangiopathy. Then the extent of infestation on the undersides of the leaves was visually determined.
  • Leaves of potted tomato plants were sprayed to drip point in the concentration of active compound indicated below.
  • the plants were placed for 3 days at about 20 0 C in a greenhouse and then the Blät ⁇ ter were inoculated with an aqueous Sporangienaufschwemmung of Phytophthora infestans. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 18 and 2O 0 C. After 6 days, the late blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.
  • the active compounds epoxiconazole, famoxadone, fluazinam and zoxamide were used as customary commercial formulations and prediluted with water as the stock solution of 10,000 ppm.
  • the stock solutions were mixed according to the respective ratio, pipetted into a microtiter plate (MTP) and diluted with an aqueous fungal nutrient medium to Malzba ⁇ sis to the specified drug concentration. This was followed by the addition of an aqueous spore suspension of the relevant pathogen.
  • MTP microtiter plate
  • the plates were manufactured ⁇ in a water vapor-saturated chamber at temperatures of 18 0 C provides. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the active substance-free control variant and the fungus-free and active substance-free blank value in order to determine the relative growth in% of the pathogens in the individual active substances.

Abstract

La présente invention concerne un procédé pour renforcer l'efficacité fongicide de a) l'éthaboxam de formule (I), se caractérisant en ce que le principe actif I est appliqué simultanément séparément ou communément avec au moins un principe actif II faisant partie du groupe b) qui comprend: les dithiocarbamates tels que maneb, mancozeb, metam ou metiram, des dérivés d'acide sulfénique tels que captane ou folpet, des dérivés de strobilurine tels que krésoxim-méthyle ou pyraclostrobine, des dérivés d'acide cinnamique et des analogues tels que diméthomorphe ou flumorphe, ou dithianone, famoxadone, cymoxanil, fluazinam, zoxamide, mefenoxam ou chlorothalonil, N-(2-{4-[3-(4-chlor-phényl)-prop-2-inyloxy]-3-méthoxy-phényl}-éthyl)-2-méthansulfonylamino-3-méthyl-butyramide, N-(2-{4-[3-(4-chlor-phényl)-prop-2-inyloxy]-3-méthoxy-phényl}-éthyl)-2-éthansulfonylamino-3-méthyl-butyramide ou 5-chlor-7-(4-méthyl-pipéridin-1-yl)-6-(2,4,6-trifluorphényl)-[1,2,4]triazolo[1,5-a]pyrimidine; en des quantités synergiquement actives, par pulvérisation ou saupoudrage des semences, des végétaux ou du sol, avant ou après l'ensemencement des végétaux, ou avant ou après la sortie de terre des végétaux. Selon l'invention, aucun alkyléther de polyoxyalkylène n'est utilisé comme adjuvant. L'invention a également pour objet de nouveaux mélanges synergiques d'éthaboxam et des agents qui contiennent ces mélanges ainsi que l'utilisation d'éthaboxam pour préparer ces mélanges.
EP05811186A 2004-11-25 2005-11-23 Procede pour renforcer l'efficacite de l'ethaboxam Withdrawn EP1816914A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP10171025A EP2255633A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP09176984A EP2206432A3 (fr) 2004-11-25 2005-11-23 Procédé pour accroître l'activité de l'éthaboxam
EP10171032A EP2255635A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
PL08154087T PL1949788T3 (pl) 2004-11-25 2005-11-23 Sposób wzmacniania skuteczności etaboksamu
EP10171029A EP2255634A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171034A EP2255636A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171018A EP2255631A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171023A EP2255632A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP08154087A EP1949788B1 (fr) 2004-11-25 2005-11-23 Procédé pour renforcer l'efficacité de l'ethaboxam

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102004057070 2004-11-25
DE102004058585 2004-12-03
PCT/EP2005/012528 WO2006056417A1 (fr) 2004-11-25 2005-11-23 Procede pour renforcer l'efficacite de l'ethaboxam

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EP08154087A Division EP1949788B1 (fr) 2004-11-25 2005-11-23 Procédé pour renforcer l'efficacité de l'ethaboxam

Publications (1)

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EP1816914A1 true EP1816914A1 (fr) 2007-08-15

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Application Number Title Priority Date Filing Date
EP10171023A Withdrawn EP2255632A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP08154087A Active EP1949788B1 (fr) 2004-11-25 2005-11-23 Procédé pour renforcer l'efficacité de l'ethaboxam
EP10171018A Withdrawn EP2255631A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171029A Withdrawn EP2255634A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171034A Withdrawn EP2255636A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP09176984A Withdrawn EP2206432A3 (fr) 2004-11-25 2005-11-23 Procédé pour accroître l'activité de l'éthaboxam
EP05811186A Withdrawn EP1816914A1 (fr) 2004-11-25 2005-11-23 Procede pour renforcer l'efficacite de l'ethaboxam
EP10171025A Withdrawn EP2255633A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171032A Withdrawn EP2255635A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam

Family Applications Before (6)

Application Number Title Priority Date Filing Date
EP10171023A Withdrawn EP2255632A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP08154087A Active EP1949788B1 (fr) 2004-11-25 2005-11-23 Procédé pour renforcer l'efficacité de l'ethaboxam
EP10171018A Withdrawn EP2255631A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171029A Withdrawn EP2255634A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171034A Withdrawn EP2255636A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP09176984A Withdrawn EP2206432A3 (fr) 2004-11-25 2005-11-23 Procédé pour accroître l'activité de l'éthaboxam

Family Applications After (2)

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EP10171025A Withdrawn EP2255633A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam
EP10171032A Withdrawn EP2255635A1 (fr) 2004-11-25 2005-11-23 Procédé pour augmenter l'activité de l'éthaboxam

Country Status (21)

Country Link
US (1) US20080200334A1 (fr)
EP (9) EP2255632A1 (fr)
JP (1) JP2008521761A (fr)
KR (1) KR20070086584A (fr)
CN (2) CN101743987A (fr)
AR (1) AR051777A1 (fr)
AT (1) ATE463162T1 (fr)
AU (1) AU2005308946A1 (fr)
BR (1) BRPI0518585A2 (fr)
CA (1) CA2586441A1 (fr)
CR (1) CR9145A (fr)
DE (1) DE502005009390D1 (fr)
ES (1) ES2342633T3 (fr)
IN (1) IN2007KO01845A (fr)
MX (1) MX2007005510A (fr)
PE (1) PE20060796A1 (fr)
PL (1) PL1949788T3 (fr)
TW (1) TW200631501A (fr)
UY (1) UY29229A1 (fr)
WO (1) WO2006056417A1 (fr)
ZA (1) ZA200704386B (fr)

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JP5359223B2 (ja) 2008-11-25 2013-12-04 住友化学株式会社 植物病害防除用組成物及び植物病害の防除方法
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Publication number Publication date
EP2206432A3 (fr) 2010-10-27
BRPI0518585A2 (pt) 2008-11-25
EP2255631A1 (fr) 2010-12-01
EP2255633A1 (fr) 2010-12-01
EP2206432A2 (fr) 2010-07-14
AU2005308946A1 (en) 2006-06-01
DE502005009390D1 (de) 2010-05-20
CN101743987A (zh) 2010-06-23
CR9145A (es) 2007-11-23
UY29229A1 (es) 2006-06-30
EP2255634A1 (fr) 2010-12-01
CN101065017A (zh) 2007-10-31
EP1949788A1 (fr) 2008-07-30
PE20060796A1 (es) 2006-09-29
JP2008521761A (ja) 2008-06-26
EP1949788B1 (fr) 2010-04-07
MX2007005510A (es) 2007-07-20
ES2342633T3 (es) 2010-07-09
EP2255635A1 (fr) 2010-12-01
EP2255632A1 (fr) 2010-12-01
ZA200704386B (en) 2008-10-29
PL1949788T3 (pl) 2010-09-30
US20080200334A1 (en) 2008-08-21
TW200631501A (en) 2006-09-16
CN100591207C (zh) 2010-02-24
ATE463162T1 (de) 2010-04-15
EP2255636A1 (fr) 2010-12-01
CA2586441A1 (fr) 2006-06-01
AR051777A1 (es) 2007-02-07
WO2006056417A1 (fr) 2006-06-01
KR20070086584A (ko) 2007-08-27
IN2007KO01845A (fr) 2007-08-10

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