WO2007071656A1 - Procede pour lutter contre les attaques de rouille chez les legumineuses - Google Patents

Procede pour lutter contre les attaques de rouille chez les legumineuses Download PDF

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Publication number
WO2007071656A1
WO2007071656A1 PCT/EP2006/069864 EP2006069864W WO2007071656A1 WO 2007071656 A1 WO2007071656 A1 WO 2007071656A1 EP 2006069864 W EP2006069864 W EP 2006069864W WO 2007071656 A1 WO2007071656 A1 WO 2007071656A1
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WO
WIPO (PCT)
Prior art keywords
methyl
pyrazolylcarbonsäureanilid
active ingredient
fluorine
hydrogen
Prior art date
Application number
PCT/EP2006/069864
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German (de)
English (en)
Inventor
Jochen Dietz
Siegfried Strathmann
Thomas Grote
Reinhard Stierl
Original Assignee
Basf Aktiengesellschaft
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Filing date
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Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2007071656A1 publication Critical patent/WO2007071656A1/fr

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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the invention relates to a method for controlling rust attack in legumes.
  • R 1 is hydrogen, halogen, methyl or C 1 -C 2 -haloalkyl
  • R 2 is hydrogen, fluorine, chlorine or methyl
  • R 4 is hydrogen, fluorine, chlorine, methyl or C 1 -C 2 -haloalkyl
  • the pyrazolylcarboxylic anilides I are e.g. from EP-A 589 301, WO 03/70705, WO 2004/103975, WO 2005/34628 and WO 2006/092213 or can be prepared in the manner described therein.
  • C 1 -C 2 -haloalkyl represents a partially or completely halogenated C 1 -C 2 -alkyl radical, where the halogen atom (s) is / are in particular fluorine and / or chlorine, ie, for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl , Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoro-ethyl, 2-bromo-2,2
  • R 1 is methyl or C 1 -C 2 -haloalkyl, in particular methyl or halomethyl, particularly preferably methyl, CHF 2 or CF 3 ;
  • R 2 is hydrogen or fluorine, in particular hydrogen
  • R 3 is fluorine, chlorine or methyl, in particular fluorine or chlorine; most preferably chlorine;
  • R 4 is hydrogen, fluorine or chlorine, in particular hydrogen or chlorine.
  • a significant increase in activity in the process according to the invention is achieved by the combined use of a Heterocyclylcarbonklareanilids I with at least one active ingredient II from the following group in synergistically effective amounts:
  • Azoles such as bromoconazole, cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochlorazole, prothioconazole, tebuconazole, tetraconazole,
  • Triadimefon Triadimenol
  • Triticonazole Triadimefonazole
  • Acylalanines such as benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl,
  • Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil, dicarboximides such as iprodione, procymidone, vinclozolin,
  • Heterocyclic compounds such as benomyl, boscalid, carbendazim, carboxin, oxycarboxin, fuberidazole, picobenzamide, penthiopyrad, proquinazide, thiabendazole, thiophanate-methyl, phenylpyrroles such as fenpiclonil or fludioxonil,
  • fungicides such as benthiavalicarb, cyflufenamid, fosetyl, fosetyl-aluminum, phosphorous acid or its salts, iprovalicarb, metrafenone and 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6 trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine,
  • strobilurins such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluoxazirbin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrinbin, trifloxystrobin, (2-chloro-5- [1 - (3-methyl-benzyloxyimino) -ethyl ] benzyl) - carbamic acid methyl ester, (2-chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester and 2-ortho - [(2,5-dimethylphenyl oxymethylene ) phenyl] -3-methoxy-methyl acrylate; Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • the invention therefore also relates to fungicidal mixtures for controlling rust fungi, containing as active components A) a Pyrazolylcarbonklaanilid I, and
  • the pyrazolylcarboxylic acid anilide I and the active compound II 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.
  • the control of harmful fungi takes place by application of the pyrazolylcarboxylic acid anilides I by seed treatment, spraying or dusting of the plants or the soil before or after sowing of the plants, or before or after emergence of the plants.
  • the control of rust diseases in legumes is advantageously carried out by the application of an aqueous treatment of a formulation containing a Pyrazolylcarbonklaanilid I on the above-ground parts of plants, especially the leaves, or, as prophylaxis due to the high systemic effect, by seed or soil treatment done.
  • the compounds I and II are usually employed in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, in particular 10: 1 to 1:10.
  • the Pyrazolylcarbonklaanilids I can be used in the process according to the invention advantageously together with other active ingredients IM, in addition to the active ingredients II also with herbicides, insecticides, growth regulators, other fungicides or with fertilizers.
  • Particularly suitable as these further mixing partners IM are: imazethapyr, imazamox, imazapyr, imazapic, or dimethenamid-p;
  • Fipronil Imidacloprid, Acetamipird, Nitenpyram, Carbofuran, Carbosulfan, Benfurabarb, Thiacloprid, Clothianidin, MTI 446 and CGA 293343.
  • the compounds I and IM are usually used in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, in particular 10: 1 to 1:10 applied.
  • pyrazolylcarboxylic anilides I in soybeans has led to a significant increase in yield.
  • the application of the pyrazolylcarboxylic anilides I can thus also be carried out for the purpose of increasing the yield.
  • the increase in yield in combination with the excellent effect of pyrazolylcarboxylic acid Nilides I against rust diseases in legumes makes the process according to the invention valuable for the farmer. Excellent results can be achieved by using a Pyrazolylcarbonklaanilids I in combination with an active ingredient II.
  • the pyrazolylcarboxylic anilides I and the above-described mixtures of I and II are also suitable for controlling the above-mentioned. Diseases.
  • the pyrazolylcarboxylic anilides I or the mixtures of I and II are used by treating the fungi or the plants, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active compounds.
  • the application can take place both before and after the infection of the materials or plants by the fungi.
  • the treatment preferably takes place before the infection.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • drug amounts of 1 to 1500 g of Pyrazolylcarbonklaanilid I, preferably 10 to 500 g, per 100 kilograms of seed.
  • the application rates of the mixtures according to the invention are, depending on the nature of the active compound II and the desired effect at 10 g / ha to 2500 g / ha, preferably 50 to 2000 g / ha, in particular 100 to 1500 g / ha.
  • the application rates for the pyrazolylcarboxylic acid anilide I are accordingly generally from 1 to 1000 g / ha, preferably from 10 to 750 g / ha, in particular from 20 to 500 g / ha.
  • the application rates for the active compound II are accordingly generally 1 to 1500 g / ha, preferably 10 to 1250 g / ha, in particular 20 to 1000 g / ha.
  • application rates of mixture of 1 to 2000 g / 100 kg of seed preferably 1 to 1500 g / 100 kg, in particular 5 to 1000 g / 100 kg, are generally used.
  • the compounds may be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; 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, e.g. by stretching the active compound with solvents and / or excipients, if desired with use of emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • 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 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, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin
  • 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, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene glycol octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphen
  • 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 e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree 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 sulphate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a compound according to the invention 20 parts by weight of a compound according to the invention 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 gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • a compound according to the invention 15 parts by weight of a compound according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 15% by weight.
  • a compound according to the invention 25 parts by weight of a compound according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine Wirkstoffsuspension sion. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • 50 parts by weight of a compound according to the invention 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.
  • 0.5 parts by weight of a compound according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
  • 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 (wettable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the 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, possibly also just immediately 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.
  • the active compounds were prepared separately or together as a stock solution with 25 mg Pyrazolylcarbonklaanilid I, which with a mixture of acetone and / or dimethyl sulfoxide (DMSO) and the emulsifier Wettol ® EM 31 (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in Volume ratio of solvent-emulsifier of 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 concentration of active substance indicated below.
  • DMSO dimethyl sulfoxide
  • Wettol ® EM 31 wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Seeds of soybean BRS 133 were treated with 1000 g of a pyrazolecarboxylic acid anilide I / 100 kg of seed, formulated as SC with 250 g of active ingredient per liter, as wet-sponges, then seeded in pots and cultivated in a greenhouse at ca. 22 ° C. 3 weeks after sowing, the plants were inoculated with soybean rust, for 24 hours at 100% rel. Humidity incubated and then cultivated again in the greenhouse. At the time of inoculation, the first pair of leaves and a follow-up blade were developed. 1 1 days after the inoculation, the infestation of the leaves was evaluated.
  • a stock solution of 10,000 ppm was prepared.
  • the stock solution was diluted with water to the concentrations to be tested.
  • the concentrations used are in g a.i. given per 100 kg of seed.
  • 1 ml of the respective solution was pipetted into vermiculite soybean seedlings. Seven days after application of the treatments, the soybean plants were inoculated with a spore suspension of Phakopsora pachyrhizi. After an incubation period of 14 days, the first pair of leaves were scored (% infected leaf area).
  • a stock solution of 10,000 ppm was prepared.
  • the stock solution was diluted with water to the concentrations to be tested. The concentrations used are given in grams per 100 kg of seed. 1 ml of the respective solution was pipetted into vermiculite soybeans. 14 days after sowing or after application of the treatments, the soybean plants were inoculated with a spore suspension of Phakopsora pachyrhizi. After an incubation period of 14 days, the first pair of leaves were scored (% infected leaf area). While the leaf area of the untreated plants was 83% infected, the leaves of those plants whose seeds had been treated with 250 g of compound No. Ia.24 per 100 kg of seed had no infestation.

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

Abstract

L'invention concerne un procédé servant à lutter contre les attaques de rouille chez les légumineuses en utilisant des anilides d'acide pyrazolylcarboxylique de formule (I), dans laquelle R<SUP>1</SUP> représente H, halogène, CH<SUB>3</SUB> ou halogénure d'alkyle C<SUB>1</SUB>-C<SUB>2</SUB>, R<SUP>2</SUP> représente H, F, Cl ou CH<SUB>3</SUB>, R<SUP>3</SUP> représente F, Cl, CH<SUB>3</SUB>, halogénure d'alkyle C<SUB>1</SUB>-C<SUB>2</SUB>, -CH=N-OR<SUP>5</SUP> ou -C(CH<SUB>3</SUB>)=N-OR<SUP>5</SUP>, R<SUP>4</SUP> représente H, F, Cl, CH<SUB>3</SUB> ou halogénure d'alkyle C<SUB>1</SUB>-C<SUB>2</SUB> et R<SUP>5</SUP> représente H, CH<SUB>3</SUB> ou C<SUB>2</SUB>H<SUB>5</SUB>. L'invention concerne également des mélanges d'anilides d'acide pyrazolylcarboxylique de formule (I) avec un agent fongicide II sélectionné dans le groupe des azoles, acylalanines, dérivés d'amine, anilinopyrimidines, dicarboximides, dithiocarbamates, composés hétérocycliques, phénylpyrroles, amides de l'acide cinnamique et analogues, ou avec d'autres agents conformément à la description. L'invention concerne enfin des produits et semences contenant ces mélanges.
PCT/EP2006/069864 2005-12-20 2006-12-18 Procede pour lutter contre les attaques de rouille chez les legumineuses WO2007071656A1 (fr)

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EP05027939.7 2005-12-20
EP05027939 2005-12-20

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Cited By (9)

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WO2008014905A2 (fr) * 2006-08-03 2008-02-07 Bayer Cropscience Ag 3-difluorométhyl-pyrazolylcarboxanilide
EP2020854A1 (fr) * 2006-05-03 2009-02-11 Basf Se Utilisation de biphenylamides d'acide arylcarboxylique pour le traitement de semences
WO2009098223A2 (fr) * 2008-02-05 2009-08-13 Basf Se Composition phytosanitaire
WO2009098218A2 (fr) * 2008-02-05 2009-08-13 Basf Se Composition phytosanitaire
WO2010025832A1 (fr) * 2008-09-03 2010-03-11 Bayer Cropscience Ag Utilisation de compositions de composés fongicides pour lutter contre certaines rouilles
WO2011069893A1 (fr) 2009-12-08 2011-06-16 Basf Se Mélanges pesticides
CN103391925A (zh) * 2010-11-15 2013-11-13 拜耳知识产权有限责任公司 5-卤代吡唑甲酰胺
US8748342B2 (en) 2009-12-08 2014-06-10 Basf Se Pesticidal mixtures
CN103907609A (zh) * 2013-01-06 2014-07-09 江苏丰登农药有限公司 一种含氟唑菌酰胺和醚菌酯的杀菌组合物及其应用

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WO1999009013A1 (fr) * 1997-08-15 1999-02-25 Basf Aktiengesellschaft Fluorpyrazole-biphenylamides fongicides
JPH11335364A (ja) * 1998-05-22 1999-12-07 Mitsui Chem Inc 新規な酸アニリド誘導体およびこれを有効成分とする植物病害防除剤
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US9049859B2 (en) 2009-12-08 2015-06-09 Basf Se Pesticidal mixtures
EA022245B1 (ru) * 2009-12-08 2015-11-30 Басф Се Пестицидные смеси
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CN103391925A (zh) * 2010-11-15 2013-11-13 拜耳知识产权有限责任公司 5-卤代吡唑甲酰胺
US9375004B2 (en) 2010-11-15 2016-06-28 Bayer Intellectual Property Gmbh 5-halogenopyrazolecarboxamides
CN103391925B (zh) * 2010-11-15 2017-06-06 拜耳知识产权有限责任公司 5‑卤代吡唑甲酰胺
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