EP1830645A1 - Fungicidal mixtures - Google Patents

Fungicidal mixtures

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Publication number
EP1830645A1
EP1830645A1 EP05824381A EP05824381A EP1830645A1 EP 1830645 A1 EP1830645 A1 EP 1830645A1 EP 05824381 A EP05824381 A EP 05824381A EP 05824381 A EP05824381 A EP 05824381A EP 1830645 A1 EP1830645 A1 EP 1830645A1
Authority
EP
European Patent Office
Prior art keywords
active
compound
compounds
methyl
mixtures
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Withdrawn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
EP05824381A
Other languages
German (de)
French (fr)
Inventor
Markus Gewehr
Reinhard Stierl
Matthias NIEDENBRÜCK
Udo HÜNGER
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
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1830645A1 publication Critical patent/EP1830645A1/en
Withdrawn legal-status Critical Current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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids

Definitions

  • the present invention relates to fungicidal mixtures containing as active components
  • Fenpiclonil fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph,
  • D together with the nitrogen atom forms a pyrrolidine, piperidine or azepin ring, which rings are unsubstituted or substituted by one or two methyl groups or by an ethyl, propyl or butyl group; and L is methyl, fluorine or chlorine;
  • the invention relates to a method for controlling harmful fungi with mixtures of the compound I with active compounds II and the use of the compound I with active compounds II for the preparation of such mixtures and compositions containing these mixtures.
  • the active compounds II mentioned above as component 2 their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available. Fluazinam, S-chloro-N-tS-chloro- ⁇ , -dinitro ⁇ -rifluoro-methyl-phenyl-S-rifluoromethyl) -pyridine-amine (The Pecticide Manual, Ed. The British Crop Protection Council, 10th edition (1995 ), P. 474);
  • 2,5 (or 2,6) -dimethylmorpholine and "alkyf” may also be octyl, decyl, tetradecyl or hexadecyl, and wherein the cis / trans ratio is 1: 1;
  • Tridemorph 2,6-dimethyl-4-tridecylmorpholine (DE 11 64 152), fenpropidine, (RS) -I- [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (DE 27 52 096)
  • ⁇ -Chloro- ⁇ -phenyl-T-heterocyclylamino-triazolopyrimidines of the formula HA are generally known from US Pat. No. 5,593,996.
  • the present invention was based on mixtures which show an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of applied active substances.
  • the mixtures of the compound I and of an active compound II, or the simultaneous joint or separate use of the compound I and an active compound II are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes , Oomycetes and Basidiomycetes. They are in part systemically effective and can be used in crop protection as foliar and soil fungicides.
  • fungi Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphae- rotheca fuliginea on cucurbits, Podosphaera leucot ⁇ cha on apples, Uncinula necator on vines, Puccinia A ⁇ en on cereals, Rhizoctonia species Cotton, Rice and Turf, Ustilago A anen on cereals and sugarcane, Venturia inaequalis on apples, Bipolaris and Drechslera species on cereals, rice and turf, Septo ⁇ a A ⁇ en on wheat, Botrytis cinerea on strawberries, vegetables, ornamental plants and vines, Mycos - phaerella-A ⁇ en on bananas, peanuts and cereals, Pseudocercosporella herpotri- choides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on
  • mixtures of compound I and of an active compound II are particularly suitable for controlling harmful fungi from the class Oomycetes.
  • the compound I and active compounds 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.
  • L is fluorine and D has one of the following meanings: - (CHz) 4 -; -CH 2 -CH (CHs) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CHS) -CH 2 -CH (CHS) -CH 2 -J-CH (CHS) -CH 2 -CH 2 -CH (CHS) -; -CH 2 CH (CH 3 ) -CH 2 -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2
  • the pure active ingredients which can be added as needed further active ingredients against harmful fungi or other pests such as insects, spider animals or nematodes, or herbicidal or growth-regulating agents or fertilizers as further active components.
  • mixtures of compound I with an active ingredient II are used. Under certain circumstances, however, mixtures of compound I with two or optionally several active components may be advantageous.
  • the compound I and the active compound II are usually employed in a weight ratio of from 100: 1 to 1: 100, preferably from 20: 1 to 1:20, in particular from 10: 1 to 1:10.
  • the further active components are added to compound I in a ratio of from 20: 1 to 1:20.
  • the application rates of the mixtures according to the invention are from 5 g / ha to 2000 g / ha, preferably from 50 to 900 g / ha, in particular from 50 to 750 g / ha.
  • the application rates for the compound I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha.
  • the application rates for the active compound II are correspondingly generally 1 to 2000 g / ha, preferably 10 to 900 g / ha, in particular 40 to 500 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 combined application of the compound I and the active compound II or the mixtures of the compound I and the active ingredient II by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
  • the mixtures according to the invention or the compound I and the active compound II can be converted into the customary 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 ingredient with solvents and / or carriers, if desired using 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 may also be used, - carriers 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 (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, chalk
  • 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, 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 meal, 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 ingredients.
  • the active ingredients are employed in egg 'ner purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • 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 according to the invention are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • the active compounds 20 parts by weight 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
  • 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 added to 30 parts by weight of water by means of an emulsifying machine (e.g., Ultraturax) and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients 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 active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing 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.
  • Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • I dusts (DP, DS) 5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.
  • J Granules 0.5 parts by weight of the active ingredients 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 0.5 wt .-% active ingredient content.
  • 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 active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water.
  • the active compounds can be used as such, in the form of their formulations or the use 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 be applied.
  • the forms of application are based entirely on the application purposes; In any case, they should ensure the finest possible 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 adding 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.
  • 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- never 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 applied by mixing the harmful fungi, the plants, seeds, soils, areas, materials or spaces to be kept free of them with a fungicidally effective amount of the mixture or of the compounds I and II when applied separately.
  • the application can be made 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 ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.
  • the active ingredient fluazinam was used as a commercially available formulation and prediluted with water to the stock solution concentration of 10,000 ppm.
  • 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.
  • the active ingredient Fluazinam was used as a commercial formulation and diluted with water to the specified conc.
  • the measured parameters were compared with the growth of the drug-free control variant and the fungus-free and active substance-free blank to determine the relative growth in% of the pathogens in the individual active ingredients.
  • 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 that of the untreated control plants; at an efficiency of 100, the treated plants have no infestation.
  • the expected efficiencies for drug combinations were determined according to the Colby formula (Colby, SR (Calculating synergistic and antagonistic responses of herbicidal combinations), Weeds, 15, pp. 20-22, 1967) and compared with the observed efficiencies.
  • the stock solutions were mixed according to the ratio, pipetted into a microtiter plate (MTP) and diluted with an aqueous fungus nutrient medium based on malt to the stated active compound concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. Using an absorption photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below. Five days later, the leaves were infected with an aqueous sporangia suspension of Phytophthora infestans. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° 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%.

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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

The invention relates to fungicidal mixtures which comprise as the active components 1) the strobilurin derivative of formula (I), and 2) at least one active substance (II) which is selected from the group including heterocyclic compounds, in a synergistically effective amount. The invention also relates to a method for controlling parasitic fungi with mixtures of compound (I) that comprise active substances (II) and to the use of compound (I) with active substances (II) for producing such mixtures, and to agents that comprise these mixtures.

Description

Fungizide MischungenFungicidal mixtures
Beschreibungdescription
Die vorliegende Erfindung betrifft fungizide Mischungen, enthaltend als aktive KomponentenThe present invention relates to fungicidal mixtures containing as active components
1) das Strobilurinderivat der Formel I,1) the strobilurin derivative of the formula I,
und and
2) mindestens einen Wirkstoff Il ausgewählt aus der Gruppe heterocylischer Verbindungen:2) at least one active ingredient II selected from the group of heterocyclic compounds:
Fluazinam, Pyrifenox,Fluazinam, pyrifenox,
Bupirimate, Cyprodinil, Fenarimol, Ferimzone, Mepanipyrim, Nuarimol, Pyri- methanil,Bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil,
Triforine,triforine,
Fenpiclonil, Fludioxonil, Aldimorph, Dodemorph, Fenpropimorph, Tridemorph,Fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph,
Fenpropidin,fenpropidin,
Iprodione, Procymidone, Vinclozolin,Iprodione, procymidone, vinclozolin,
Famoxadone, Fenamidone, Octhilinone, Probenazole,Famoxadone, Fenamidone, Octhilinone, Probenazole,
5-Chlor-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trif luor-phenyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin,5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine,
Anilazin, Diclomezine, Pyroquilon, Proquinazid, Tricyclazole,Anilazine, diclomezine, pyroquilone, proquinazide, tricyclazole,
2-Butoxy-6-iodo-3-propyl-chromen-4-on,2-butoxy-6-iodo-3-propyl-chromen-4-one,
Acibenzolar-S-methyl, Captafol, Captan, Dazomet, Folpet, Fenoxanil, Quin- oxyfen, 3-(3-Brom-6-fluor-2-methyl-indol-1 -sulfonyl)-[1 ,2,4]triazol-1 -sulfonsäure- dimethylamid und δ-Chlor-β-phenyl-Z-heterocyclylamino-triazolopyrimidine der Formel H-A, in derAcibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole 1-sulfonodimethylamide and 6-chloro-β-phenyl-Z-heterocyclylamino-triazolopyrimidines of the formula HA, in the
D zusammen mit dem Stickstoffatom einen Pyrrolidin-, Piperidin- oder Aze- pinring bildet, welche Ringe unsubstituiert sind oder durch eine oder zwei Methyl gruppen oder durch eine Ethyl, Propyl oder Butylgruppe substituiert sind; und L Methyl, Fluor oder Chlor bedeutet;D together with the nitrogen atom forms a pyrrolidine, piperidine or azepin ring, which rings are unsubstituted or substituted by one or two methyl groups or by an ethyl, propyl or butyl group; and L is methyl, fluorine or chlorine;
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
Außerdem betrifft die Erfindung ein Verfahren zur Bekämpfung von Schadpilzen mit Mischungen der Verbindung I mit Wirkstoffen Il und die Verwendung der Verbindung I mit Wirkstoffen Il zur Herstellung derartiger Mischungen sowie Mittel, die diese Mischungen enthalten.Moreover, the invention relates to a method for controlling harmful fungi with mixtures of the compound I with active compounds II and the use of the compound I with active compounds II for the preparation of such mixtures and compositions containing these mixtures.
Das als Komponente 1 voranstehend bezeichnete Strobilurinderivat der Formel I, 2-{2- [3-(4-Chlorphenyl)-1-methyl-allylidenaminooxymethyl]-phenyl}-3-methoxy-acrylsäure- methylester, dessen Herstellung und dessen Wirkung gegen Schadpilze ist aus der Literatur bekannt (EP-A 936 213, common name: Enestroburin).The Strobilurinderivat of formula I, 2- {2- [3- (4-chlorophenyl) -1-methyl-allylidenaminooxymethyl] -phenyl} -3-methoxy-acrylic acid methyl ester, referred to as the component 1 above, its preparation and its action against harmful fungi is known from the literature (EP-A 936 213, common name: Enestroburin).
Die voranstehend als Komponente 2 genannten Wirkstoffe II, ihre Herstellung und ihre Wirkung gegen Schadpilze sind allgemein bekannt (vgl.: http://www.hclrss.demon.co.uk/index.html); sie sind kommerziell erhältlich. Fluazinam, S-Chlor-N-tS-chlor^.ö-dinitro^-^rifluoromethyOphenyO-S-^rifluormethyl)^- pyridin-amin (The Pecticide Manual, Hrsg. The British Crop Protection Council, 10. Aufl. (1995), S. 474);The active compounds II mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available. Fluazinam, S-chloro-N-tS-chloro-α, -dinitro ^ -rifluoro-methyl-phenyl-S-rifluoromethyl) -pyridine-amine (The Pecticide Manual, Ed. The British Crop Protection Council, 10th edition (1995 ), P. 474);
Pyrifenox, 1-(2,4-Dichlorphenyl)-2-(3-pyridinyl)ethanon-O-methyloxim (EP-A 49 854) Bupirimate, 5-Butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl-dimethylsulfamat (GB 14 00 710), Cyprodinil, (4-Cyclopropyl-6-methyl-pyrimidin-2-yl)-phenyl-amin (EP-A 310 550);Pyrifenox, 1- (2,4-dichlorophenyl) -2- (3-pyridinyl) ethanone O-methyloxime (EP-A 49 854) Bupirimate, 5-butyl-2- (ethylamino) -6-methyl-4-pyrimidinyl dimethyl sulfamate (GB 14 00 710), cyprodinil, (4-cyclopropyl-6-methyl-pyrimidin-2-yl) -phenyl-amine (EP-A 310,550);
Fenarimol, α-(2-Chlorphenyl)-σ-(4-chlorphenyl)-5-pyrimidinmethanol (GB 12 18 623), Ferimzone, (Z)-2'-Methylacetophenon 4,6-dimethylpyrimidin-2-ylhydrazon; Mepanipyrim, (4-Methyl-6-prop-1-inyl-pyrimidin-2-yl)-phenyl-amin (EP-A 224 339); Nuarimol, α-(2-Chlorphenyl)-σ-(4-fluorphenyl)-5-pyrimidinmethanol (GB 12 18 623); Pyrimethanil, 4,6-Dimethyl-pyrimidin-2-yl)-phenyl-amin (DD-A 151 404); Triforine, Λ/,Λ/'-{Piperazine-1 ^-diylbisKtrichlormethyOmethylenftdiformamid (DEFenarimol, α- (2-chlorophenyl) -σ- (4-chlorophenyl) -5-pyrimidinemethanol (GB 12 18 623), ferimzone, (Z) -2'-methylacetophenone 4,6-dimethylpyrimidin-2-ylhydrazone; Mepanipyrim, (4-methyl-6-prop-1-ynyl-pyrimidin-2-yl) -phenyl-amine (EP-A 224 339); Nuarimol, α- (2-chlorophenyl) -σ- (4-fluorophenyl) -5-pyrimidinemethanol (GB 12 18 623); Pyrimethanil, 4,6-dimethyl-pyrimidin-2-yl) -phenyl-amine (DD-A 151 404); Triforine, Λ /, Λ / '- {piperazine-1 ^ -diylbis-trichloromethylmethylene tetdiformamide (DE
19 01 421);19 01 421);
Fenpiclonil, 4-(2,3-Dichlor-phenyl)-1H-pyrrol-3~carbonitril (Proc. 1988 Br. Crop Prot.Fenpiclonil, 4- (2,3-dichlorophenyl) -1H-pyrrole-3-carbonitrile (Proc. 1988 Br. Crop Prot.
Conf. - Pests Dis., Bd. 1, S. 65); Fludioxonil, 4-(2,2-Difluor-benzo[1 ,3]dioxol-4-yl)-1 H-pyrrol-3-carbonitril (The PecticideConf. - Pests Dis., Vol. 1, p. 65); Fludioxonil, 4- (2,2-Difluoro-benzo [1,3-dioxol-4-yl] -1H-pyrrole-3-carbonitrile (The Pecticide
Manual, Hrsg. The British Crop Protection Council, 10. Aufl. (1995), S. 482);Manual, ed. The British Crop Protection Council, 10th Ed. (1995), p. 482);
Aldimorph, 4-Alkyl-2,5(oder 2,6)-dimethylmorpholine, enthaltend 65-75% 2,6-Dimethyl- morpholine und 25-35% 2,5-Dimethylmorpholine, wobei mehr als 85% 4-Dodecyl-Aldimorph, 4-alkyl-2,5 (or 2,6) -dimethylmorpholines containing 65-75% 2,6-dimethyl-morpholines and 25-35% 2,5-dimethylmorpholines, wherein more than 85% of 4-dodecyl-
2,5(oder 2,6)-dimethylmorpholin ist und „Alkyf" auch Octyl, Decyl, Tetradecyl oder He- xadecyl sein kann und wobei das cis/trans Verhältnis 1 :1 ist;2,5 (or 2,6) -dimethylmorpholine and "alkyf" may also be octyl, decyl, tetradecyl or hexadecyl, and wherein the cis / trans ratio is 1: 1;
Dodemorph, 4-Cyclododecyl-2,6-dimethylmorpholin (DE 1198125),Dodemorph, 4-cyclododecyl-2,6-dimethylmorpholine (DE 1198125),
Fenpropimorph, (f?S)-c/s-4-[3-(4-te/t-Butylphenyl)-2-methylpropyl]-2,6-dimethyl- morpholin (DE 27 52 096),Fenpropimorph, (f? S) -c / s-4- [3- (4-tert.-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE 27 52 096),
Tridemorph, 2,6-Dimethyl-4-tridecylmorpholin (DE 11 64 152), Fenpropidin, (RS)-I -[3-(4-tert-Butylphenyl)-2-methylpropyl]piperidin (DE 27 52 096)Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE 11 64 152), fenpropidine, (RS) -I- [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (DE 27 52 096)
Iprodion, 3-(3,5-Dichlor-phenyl)-2,4-dioxo-imidazolidin-1-carbonsäureisopropylamidIprodione, 3- (3,5-dichloro-phenyl) -2,4-dioxo-imidazolidine-1-carboxylic acid isopropylamide
(GB 13 12 536);(GB 13 12 536);
Procymidon, Λ/-(3,5-Dichlorphenyl)-1 ,2-dimethylcyclopropan-i ,2-dicarboximid (USProcymidone, Λ / - (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-i, 2-dicarboximide (US Pat
3 903 090); Vinclozolin, 3-(3,5-Dichlor-phenyl)-5-methyl-5-vinyl-oxazolidin-2,4-dion (DE-OS3,903,090); Vinclozoline, 3- (3,5-dichloro-phenyl) -5-methyl-5-vinyl-oxazolidine-2,4-dione (DE-OS
22 07 576);22 07 576);
Famoxadon, (RS)-3-Anilino-5-methyl-5-(4-phenoxyphenyl)-1 ,3-oxazolidin-2,4-dion ;Famoxadone, (RS) -3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione;
Fenamidon, (S)-I -Anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-on ;Fenamidone, (S) -1 -anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one;
Octhilinone, Probenazole, 3-Allyloxy-1 ,2-benzothiazol 1 ,1-dioxid [CAS RN 27605-76-1];Octhilinone, Probenazole, 3-allyloxy-1,2-benzothiazole 1,1-dioxide [CAS RN 27605-76-1];
Anilazin, 4,6-Dichlor-Λ/-(2-chlorphenyl)-1 ,3,5-triazin-2-amin (US 2 720 480);Anilazine, 4,6-dichloro-Λ / - (2-chlorophenyl) -1, 3,5-triazin-2-amine (US 2,720,480);
Diclomezine, 6-(3,5-Dichlorphenyl-p-tolyl)pyridazin-3(2/-/)-on;Diclomezine, 6- (3,5-dichlorophenyl-p-tolyl) pyridazine-3 (2 / - /) - on;
Pyroquilon, 1,2,5,6-Tetrahydropyrrolo[3,2,1-//]chinolin-4-on (GB 13 94 373);Pyroquilone, 1,2,5,6-tetrahydropyrrolo [3,2,1 -] quinolin-4-one (GB 13 94 373);
Proquinazid, 6-Jodo-2-propoxy-3-propylquinazoIin-4(3H)-on (WO 97/48684); Tricyclazole, 5-Methyl-1 ,2,4-triazolo[3,4-/b]benzothiazol (GB 14 19 121);Proquinazide, 6-iodo-2-propoxy-3-propylquinazoline-4 (3H) -one (WO 97/48684); Tricyclazoles, 5-methyl-1,2,4-triazolo [3,4- / b] benzothiazole (GB 14 19 121);
Acibenzolar-S-methyl, Benzo[1,2,3]thiadiazol-7-carbothionsäuremethylester;Acibenzolar-S-methyl, benzo [1,2,3] thiadiazole-7-carbothionic acid methyl ester;
Captafol, Λ/-(1 ,1 ,2,2-Tetrachloroethylthio)cyclohex-4-en-1 ,2-dicarboximid;Captafol, Λ / - (1,1,2,2-tetrachloroethylthio) cyclohex-4-ene-1,2-dicarboximide;
Captan, 2-Trichlormethylsulfanyl-3a,4,7,7a-tetrahydro-isoindol-1 ,3-dion (USCaptan, 2-trichloromethylsulfanyl-3a, 4,7,7a-tetrahydroisoindole-1,3-dione (US Pat
2 553 770); Dazomet, 3,5-Dimethyl-1 ,3,5-thiadiazinan-2-thion;2 553 770); Dazomet, 3,5-dimethyl-1,3,5-thiadiazinan-2-thione;
Folpet, 2-Trichlormethylsulfanyl-isoindol-1 ,3-dion (US 2 553 770);Folpet, 2-trichloromethylsulfanylisoindole-1,3-dione (US 2,553,770);
Fenoxanil, A/-(1-Cyano-1 ,2-dimethylpropyl)-2-(2,4-dichlorphenoxy)propanamid (EP-AFenoxanil, A / - (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propanamide (EP-A
262 393);262 393);
Quinoxyfen, 5,7-Dichlor-4-(4-fluor-phenoxy)-chinolin (US 5 240 940); Die Verbindungen ohne common name, ihre Herstellung und ihre fungizide Wirkung sind ebenfalls bekannt:Quinoxyfen, 5,7-dichloro-4- (4-fluoro-phenoxy) -quinoline (US 5,240,940); The compounds without common name, their preparation and their fungicidal action are also known:
5-Chlor-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluor-phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyri- midin, (WO 98/46608), 2-Butoxy-6-iodo-3-propyl-chromen-4-on (WO 03/14103);5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine , (WO 98/46608), 2-butoxy-6-iodo-3-propyl-chromen-4-one (WO 03/14103);
3-(3-Brom-6-fluor-2-methyl-indol-1 -sulfonyl)-[1 ,2,4]triazol-1 -sulfonsäuredimethylamid, (WO 03/053145),3- (3-bromo-6-fluoro-2-methyl-indol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide, (WO 03/053145),
δ-Chlor-β-phenyl-T-heterocyclylamino-triazolopyrimidine der Formel H-A sind allgemein bekannt aus US 5 593 996. δ-Chloro-β-phenyl-T-heterocyclylamino-triazolopyrimidines of the formula HA are generally known from US Pat. No. 5,593,996.
Im Hinblick auf eine Senkung der Aufwandmengen und eine Verbreiterung des Wirkungsspektrums der bekannten Verbindungen lagen der vorliegenden Erfindungen Mischungen als Aufgabe zugrunde, die bei verringerter Gesamtmenge an ausgebrach- ten Wirkstoffen eine verbesserte Wirkung gegen Schadpilze, insbesondere für bestimmte Indikationen, zeigen.With regard to a reduction of the application rates and a widening of the spectrum of action of the known compounds, the present invention was based on mixtures which show an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of applied active substances.
Demgemäss wurden die eingangs definierten Mischungen gefunden. Es wurde außerdem gefunden, dass sich bei gleichzeitiger gemeinsamer oder getrennter Anwendung der Verbindung I und eines Wirkstoffs Il oder bei Anwendung der Verbindung I und eines Wirkstoffs Il nacheinander Schadpilze besser bekämpfen lassen als mit den Einzelverbindungen (synergistische Mischungen). Die Verbindung I lässt sich als Synergist für eine Vielzahl verschiedener Wirkstoffe verwenden. Durch gleichzeitige gemeinsame oder getrennte Anwendung der Verbindung I mit einem Wirkstoff Il wird die fun- gizide Wirksamkeit in überadditivem Maße erhöht.Accordingly, the mixtures defined above were found. It has also been found that, with simultaneous simultaneous or separate application of the compound I and of an active compound II or, when using the compound I and an active compound II, harmful fungi can be controlled better successively than with the individual compounds (synergistic mixtures). Compound I can be used as a synergist for a variety of different agents. By simultaneous joint or separate application of the compound I with an active compound II, the fungicidal activity is increased to a superadditive extent.
Die Mischungen der Verbindung I und eines Wirkstoffs II, bzw. die gleichzeitige gemeinsame oder getrennte Verwendung der Verbindung I und eines Wirkstoffs Il zeichnen sich aus durch eine hervorragende Wirksamkeit gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Deutero- myceten, Oomyceten und Basidiomyceten. Sie sind zum Teil systemisch wirksam und können im Pflanzenschutz als Blatt- und Bodenfungizide eingesetzt werden.The mixtures of the compound I and of an active compound II, or the simultaneous joint or separate use of the compound I and an active compound II are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes , Oomycetes and Basidiomycetes. They are in part systemically effective and can be used in crop protection as foliar and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an ver- schiedenen Kulturpflanzen wie Bananen, Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen und Kürbisse), Gerste, Gras, Hafer, Kaffee, Kartoffeln, Mais, Obstpflanzen, Reis, Roggen, Soja, Tomaten, Wein, Weizen, Zierpflanzen, Zuckerrohr und einer Vielzahl von Samen.They are of particular importance for the control of a large number of fungi on various crops such as bananas, cotton, vegetables (eg cucumbers, beans and pumpkins), barley, grass, oats, coffee, potatoes, corn, fruit plants. Rice, rye, soy, tomatoes, wine, wheat, ornamental plants, sugar cane and a variety of seeds.
Vorteilhaft eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Blumeria graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphae- rotheca fuliginea an Kürbisgewächsen, Podosphaera leucotήcha an Äpfeln, Uncinula necator an Reben, Puccinia-Aάen an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Aήen an Getreide und Zuckerrohr, Venturia inaequalis an Äpfeln, Bipolaris- und Drechslera-Arten an Getreide, Reis und Rasen, Septoήa-Aήen an Weizen, Botrytis cinerea an Erdbeeren, Gemüse, Zierpflanzen und Reben, Mycos- phaerella-AΛen an Bananen, Erdnüssen und Getreide, Pseudocercosporella herpotri- choides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Pseudoperonospora-Aήen an Kürbisgewächsen und Hopfen, Plasmopara viticola an Reben, Altemaria-Arten an Gemüse und Obst sowie Fusarium- und Verticillium-Aύen.Advantageously, they are suitable for controlling the following phytopathogenic fungi: Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphae- rotheca fuliginea on cucurbits, Podosphaera leucotήcha on apples, Uncinula necator on vines, Puccinia Aάen on cereals, Rhizoctonia species Cotton, Rice and Turf, Ustilago A anen on cereals and sugarcane, Venturia inaequalis on apples, Bipolaris and Drechslera species on cereals, rice and turf, Septoήa Aήen on wheat, Botrytis cinerea on strawberries, vegetables, ornamental plants and vines, Mycos - phaerella-AΛen on bananas, peanuts and cereals, Pseudocercosporella herpotri- choides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Pseudoperonospora A anen on cucurbits and hops, Plasmopara viticola on vines, Altemaria species on vegetables and fruits as well as Fusarium and Verticillium Aύen.
Die Mischungen der Verbindung I und eines Wirkstoffs Il eignen sich insbesondere zur Bekämpfung von Schadpilzen aus der Klasse der Oomyceten.The mixtures of compound I and of an active compound II are particularly suitable for controlling harmful fungi from the class Oomycetes.
Die Verbindung I und Wirkstoffe Il können gleichzeitig gemeinsam oder getrennt oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compound I and active compounds 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.
Sofern die erfindungsgemäßen Mischungen Verbindungen der Formel U-A betreffen, kommen dafür insbesondere die in der folgenden Tabelle zusammengestellten Verbindungen der Formel H-A in Frage, in denen die Gruppen D und L die folgenden Bedeutungen haben:If the mixtures according to the invention relate to compounds of the formula U-A, the compounds of the formula H-A listed in the following table are particularly suitable for this purpose, in which the groups D and L have the following meanings:
Tabelle 1Table 1
Mischungen, enthaltend Verbindungen der Formel H-A, in denen L Methyl bedeutet und D eine der folgenden Bedeutungen hat:Mixtures containing compounds of the formula H-A, in which L is methyl and D has one of the following meanings:
-(CHz)4-; -CH2-CH(CHs)-CH2-CH2-; -CH(CH3)-CH(CH3)-CH2-CH2-; -CH(CH3)-CH2-CH(CH3)-CH2-; -(CH2)S-; -CH(CHS)-CH2-CH2-CH2-CH2-; -CH(CHS)-CH2-CH2-CH(CH3)-; -CH2-CH2-CH(CH3)-CH2-CH2-; -CH(CH3)-CH(CH3)-CH2-CH2-CH2s -CH(CH3)-CH2-CH(CH3)-CH2-CH2-; -CH(CHS)-CH2-CH2-CH(CHS)-CH2-; -CH(CHS)-CH2-CH2-CH2-CH(CH3)-; -CH(CH2CHS)-CH2-CH2-CH2-CH2-; -CH-CH(CH2CHS)-CH2-CH2-CH2-; -CH2-CH2-CH(CH2CHS)-CH2-CH2-; -CH2-CH2-CH(CH2CH2CHS)-CH2-CH2-; -CH2-CH2-CH(C[CH3]S)-CH2-CH2- und -(CH2)6- stellen einen bevorzugten Gegenstand der Erfindung dar.- (CHz) 4 -; -CH 2 -CH (CHs) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH 3 ) -CH 2 -CH (CH 3 ) -CH 2 -; - (CH 2 ) S-; -CH (CHS) -CH 2 -CH 2 -CH 2 -CH 2 -; -CH (CH 2 S ) -CH 2 -CH 2 -CH (CH 3 ) -; -CH 2 -CH 2 -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -CH 2 s -CH (CH 3 ) -CH 2 -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH S ) -CH 2 -CH 2 -CH (CH S ) -CH 2 -; -CH (CH S ) -CH 2 -CH 2 -CH 2 -CH (CH 3 ) -; -CH (CH 2 CH S ) -CH 2 -CH 2 -CH 2 -CH 2 -; -CH-CH (CH 2 CH S ) -CH 2 -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 2 CH S ) -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 2 CH 2 CH S ) -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (C [CH 3 ] S ) -CH 2 -CH 2 - and - (CH 2 ) 6 - represent a preferred subject of the invention.
Daneben sind auch Mishcungen mit Verbindungen derFormel H-A bevorzugt, in denen L Fluor bedeutet und D eine der folgenden Bedeutungen hat: -(CHz)4-; -CH2-CH(CHs)-CH2-CH2-; -CH(CH3)-CH(CH3)-CH2-CH2-; -CH(CHS)-CH2-CH(CHS)-CH2-J -CH(CHS)-CH2-CH2-CH(CHS)-; -CH2CH (CH3)-CH2-CH2-CH2-; -CH2-CH2-CH (CH3)-CH2-CH2-; -CH(CH3)-CH(CH3)-CH2-CH2-CH2-; -CH(CHS)-CH2-CH(CHS)-CH2-CH2-; -CH(CHS)-CH2-CH2-CH(CHS)-CH2-; -CH(CHS)-CH2-CH2-CH2-CH(CH3)-; -CH(CH2CHS)-CH2-CH2-CH2-CH2-; -CH-CH(CH2CHS)-CH2-CH2-CH2-; -CH2-CH2-CH(CH2CHS)-CH2-CH2-; -CH2-CH2-CH(CH2CH2CHS)-CH2-CH2- und -CH2-CH2-CH(C[CH3]S)-CH2-CH2-. Daneben sind auch Mischungen mit Verbindungen der Formel H-A bevorzugt, in denen L Chlor bedeutet und D eine der folgenden Bedeutungen hat:In addition, mixtures with compounds of the formula HA are preferred in which L is fluorine and D has one of the following meanings: - (CHz) 4 -; -CH 2 -CH (CHs) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CHS) -CH 2 -CH (CHS) -CH 2 -J-CH (CHS) -CH 2 -CH 2 -CH (CHS) -; -CH 2 CH (CH 3 ) -CH 2 -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 3 ) -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -CH 2 -; -CH (CH 2 S ) -CH 2 -CH (CH S ) -CH 2 -CH 2 -; -CH (CH S ) -CH 2 -CH 2 -CH (CH S ) -CH 2 -; -CH (CH S ) -CH 2 -CH 2 -CH 2 -CH (CH 3 ) -; -CH (CH 2 CH S ) -CH 2 -CH 2 -CH 2 -CH 2 -; -CH-CH (CH 2 CH S ) -CH 2 -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 2 CH S ) -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 2 CH 2 CH S ) -CH 2 -CH 2 - and -CH 2 -CH 2 -CH (C [CH 3 ] S ) -CH 2 -CH 2 -. In addition, mixtures with compounds of the formula HA are preferred in which L is chlorine and D has one of the following meanings:
-CH(CH3)-CH(CH3)-CH2-CH2-; -CH2-CH(CHa)-CH2-CH2-; -CH(CH3)-CH2-CH(CH3)-CH2-; -CH(CHS)-CH2-CH2-CH(CH3)-; -CH2CH(CH3)-CH2-CH2-CH2-; -CH(CH3)-CH(CH3)-CH2-CH2-CH2-; -CH(CH3)-CH2-CH2-CH(CH3)-CH2-; -CH(CH3)-CH2-CH2-CH2-CH(CH3)-; -CH(CH2CHS)-CH2-CH2-CH2-CH2-; -CH-CH(CH2CHS)-CH2-CH2-CH2-; -CH2-CH2-CH(CH2CHS)-CH2-CH2-; -CH2-CH2-CH(CH2CH2CH3)-CH2-CH2- und -CH2-CH2-CH(C[CH3]S)-CH2-CH2-.-CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -; -CH 2 -CH (CHa) -CH 2 -CH 2 -; -CH (CH 3) -CH 2 -CH (CH 3) -CH 2; -CH (CH 2 S ) -CH 2 -CH 2 -CH (CH 3 ) -; -CH 2 CH (CH 3 ) -CH 2 -CH 2 -CH 2 -; -CH (CH 3 ) -CH (CH 3 ) -CH 2 -CH 2 -CH 2 -; -CH (CH 3 ) -CH 2 -CH 2 -CH (CH 3 ) -CH 2 -; -CH (CH 3 ) -CH 2 -CH 2 -CH 2 -CH (CH 3 ) -; -CH (CH 2 CHS) -CH 2 -CH 2 -CH 2 -CH 2 -; -CH-CH (CH 2 CH S ) -CH 2 -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 2 CHS) -CH 2 -CH 2 -; -CH 2 -CH 2 -CH (CH 2 CH 2 CH 3 ) -CH 2 -CH 2 - and -CH 2 -CH 2 -CH (C [CH 3 ] S ) -CH 2 -CH 2 -.
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe ein, denen man je nach Bedarf weitere Wirkstoffe gegen Schadpilze oder andere Schädlinge wie Insekten, Spinntiere oder Nematoden, oder auch herbizide oder wachstumsregulierende Wirkstoffe oder Düngemittel als weitere Aktivkomponenten beimischen kann.Preference is given to providing the mixtures, the pure active ingredients, which can be added as needed further active ingredients against harmful fungi or other pests such as insects, spider animals or nematodes, or herbicidal or growth-regulating agents or fertilizers as further active components.
Üblicherweise kommen Mischungen der Verbindung I mit einem Wirkstoff Il zur Anwendung. Unter Umständen können jedoch Mischungen der Verbindung I mit zwei oder ggf. mehreren Aktivkomponenten vorteilhaft sein.Usually, mixtures of compound I with an active ingredient II are used. Under certain circumstances, however, mixtures of compound I with two or optionally several active components may be advantageous.
Als weitere Aktivkomponenten im voranstehenden Sinne kommen besonders die eingangs genannten Wirkstoffe Il und insbesondere die voranstehend genannten bevorzugten Wirkstoffe in Frage.As further active components in the above sense, especially the above-mentioned active compounds II and in particular the above-mentioned preferred active ingredients in question.
Die Verbindung I und der Wirkstoff Il werden üblicherweise in einem Gewichtsverhält- nis von 100:1 bis 1 :100, vorzugsweise 20:1 bis 1 :20, insbesondere 10:1 bis 1 :10 angewandt.The compound I and the active compound II are usually employed in a weight ratio of from 100: 1 to 1: 100, preferably from 20: 1 to 1:20, in particular from 10: 1 to 1:10.
Die weiteren Aktivkomponenten werden gewünschtenfalls im Verhältnis von 20:1 bis 1 :20 zu der Verbindung I zugemischt.If desired, the further active components are added to compound I in a ratio of from 20: 1 to 1:20.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen je nach Art der Verbindung und des gewünschten Effekts bei 5 g/ha bis 2000 g/ha, vorzugsweise 50 bis 900 g/ha, insbesondere 50 bis 750 g/ha.Depending on the nature of the compound and the desired effect, the application rates of the mixtures according to the invention are from 5 g / ha to 2000 g / ha, preferably from 50 to 900 g / ha, in particular from 50 to 750 g / ha.
Die Aufwandmengen für die Verbindung I liegen entsprechend in der Regel bei 1 bis 1000 g/ha, vorzugsweise 10 bis 900 g/ha, insbesondere 20 bis 750 g/ha.The application rates for the compound I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha.
Die Aufwandmengen für den Wirkstoff Il liegen entsprechend in der Regel bei 1 bis 2000 g/ha, vorzugsweise 10 bis 900 g/ha, insbesondere 40 bis 500 g/ha. Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 1 bis 1000 g/100 kg Saatgut, vorzugsweise 1 bis 750 g/100 kg, insbesondere 5 bis 500 g/100 kg verwendet.The application rates for the active compound II are correspondingly generally 1 to 2000 g / ha, preferably 10 to 900 g / ha, in particular 40 to 500 g / ha. In seed treatment, 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.
Das Verfahren zur Bekämpfung von Schadpilzen erfolgt durch die getrennte oder gemeinsame Applikation der Verbindung I und des Wirkstoffs Il oder der Mischungen aus der Verbindung I und des Wirkstoffs Il durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.The method for controlling harmful fungi is carried out by the separate or combined application of the compound I and the active compound II or the mixtures of the compound I and the active ingredient II by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
Die erfindungsgemäßen Mischungen, bzw. die Verbindung I und der Wirkstoff Il können in die üblichen Formulierungen überführt werden, z.B. Lösungen, Emulsionen, Suspensionen, Stäube, Pulver, Pasten und Granulate. Die Anwendungsform richtet sich nach dem jeweiligen Verwendungszweck; sie soll in jedem Fall eine feine und gleichmäßige Verteilung der erfindungsgemäßen Verbindung gewährleisten.The mixtures according to the invention or the compound I and the active compound II can be converted into the customary 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.
Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/oder Trägerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln. Als Lösungsmittel / Hilfsstoffe kom- men dafür im wesentlichen in Betracht:The formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially:
- Wasser, aromatische Lösungsmittel (z.B. Solvesso Produkte, XyIoI), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol, Pentanol, Benzylalkohol), Keto- ne (z.B. Cyclohexanon, gamma-Butryolacton), Pyrrolidone (NMP, NOP), Acetate (Glykoldiacetat), Glykole, Dimethylfettsäureamide, Fettsäuren und Fettsäureester. Grundsätzlich können auch Lösungsmittelgemische verwendet werden, - Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); E- mulgiermittel wie nichtionogene und anionische Emulgatoren (z.B. Polyoxyethylen- Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin- Sulfitablaugen und Methylcellulose.- 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. In principle, solvent mixtures may also be used, - carriers 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 (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsul- fonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Dibutylnaphthalinsulfonsäure, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Fettalkoholsulfate, Fettsäuren und sulfa- tierte Fettalkoholglykolether zum Einsatz, ferner Kondensationsprodukte von sulfonier- tem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphtalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethy- lenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenol, Alkylphe- nolpolyglykolether, Tributylphenylpolyglykolether, Tristerylphenylpolyglykolether, Alkyl- arylpolyetheralkohole, Alkohol- und Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpoly- glykoletheracetal, Sorbitester, Ligninsulfitablaugen und Methylcellulose in Betracht.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, tributylphenyl polyglycol ethers, tristerylphenyl polyglycol ethers, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated Castor oil, polyoxyethylene alkyl, ethoxylated polyoxypropylene, Laurylalkoholpoly- glycol ether acetal, sorbitol esters, Ligninsulfitablaugen and methyl cellulose into consideration.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldis- persionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kero- sin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Toluol, Xy- lol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Cyclohexanon, Isophoron, stark polare Lösungsmittel, z.B. Dimethylsulfoxid, N-Methylpyrrolidon oder Wasser in Betracht.For the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, there are 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.
Pulver-, Streu- und Stäubmittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden, wie Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nussschalenmehl, Cellulosepulver und andere feste Trägerstoffe.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 meal, cellulose powder and other solid carriers.
Die Formulierungen enthalten im allgemeinen zwischen 0,01 und 95 Gew.-%, vorzugs- weise zwischen 0,1 und 90 Gew.-% der Wirkstoffe. Die Wirkstoffe werden dabei in ei- ' ner Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt.The formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredients. The active ingredients are employed in egg 'ner purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
Für die Saatgutbehandlung ergeben die betreffenden Formulierungen nach zwei- bis zehnfacher Verdünnung Wirkstoffkonzentrationen von 0,01 bis 60 Gew.-%, bevorzugt 0,1 bis 40 Gew.-% in den fertig verwendbaren Zubereitungen.For seed treatment, 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.
Beispiele für erfindungsgemäße Formulierungen sind: 1. Produkte zur Verdünnung in WasserExamples of formulations according to the invention are: 1. Products for dilution in water
A Wasserlösliche Konzentrate (SL, LS)A Water-soluble concentrates (SL, LS)
10 Gew.-Teile der Wirkstoffe werden mit 90 Gew.-Teilen Wasser oder einem wasserlöslichen Lösungsmittel gelöst. Alternativ werden Netzmittel oder andere Hilfsmittel zugefügt. Bei der Verdünnung in Wasser löst sich der Wirkstoff. Man erhält auf diese Weise eine Formulierung mit 10 Gew.-% Wirkstoffgehalt. B Dispergierbare Konzentrate (DC)10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content. B Dispersible Concentrates (DC)
20 Gew.-Teile der Wirkstoffe werden in 70 Gew.-Teilen Cyclohexanon unter Zusatz von 10 Gew.-Teilen eines Dispergiermittels z.B. Polyvinylpyrrolidon gelöst. Bei Ver- dünnung in Wasser ergibt sich eine Dispersion. Der Wirkstoffgehalt beträgt 20 Gew.-%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
C Emulgierbare Konzentrate (EC)C Emulsifiable Concentrates (EC)
15 Gew.-Teile der Wirkstoffe werden in 75 Gew.-Teilen XyIoI unter Zusatz von Ca- Dodecylbenzolsulfonat und Ricinusölethoxylat (jeweils 5 Gew.-Teile) gelöst. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat 15 Gew.-% Wirkstoffgehalt.15 parts by weight of the active compounds 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 15% by weight active ingredient content.
D Emulsionen (EW, EO, ES)D emulsions (EW, EO, ES)
25 Gew.-Teile der Wirkstoffe werden in 35 Gew.-Teile XyIoI unter Zusatz von Ca- Dodecylbenzolsulfonat und Ricinusölethoxylat (jeweils 5 Gew.-Teile) gelöst. Diese Mischung wird mittels einer Emulgiermaschine (z.B. Ultraturax) in 30 Gew. Teile Wasser gegeben und zu einer homogenen Emulsion gebracht. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat einen Wirkstoffgehalt von 25 Gew.-%.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 added to 30 parts by weight of water by means of an emulsifying machine (e.g., Ultraturax) and made into a homogeneous emulsion. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.
E Suspensionen (SC, OD, FS)E suspensions (SC, OD, FS)
20 Gew.-Teile der Wirkstoffe werden unter Zusatz von 10 Gew.-Teilen Dispergier- und Netzmitteln und 70 Gew.-Teilen Wasser oder einem organischen Lösungsmittel in einer Rührwerkskugelmühle zu einer feinen Wirkstoffsuspension zerkleinert. Bei der Verdünnung in Wasser ergibt sich eine stabile Suspension des Wirkstoffs. Der Wirk- stoffgehalt in der Formulierung beträgt 20 Gew.-% .20 parts by weight of the active ingredients 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 active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight.
F Wasserdispergierbare und wasserlösliche Granulate (WG, SG) 50 Gew.-Teile der Wirkstoffe werden unter Zusatz von 50 Gew-Teilen Dispergier- und Netzmitteln fein gemahlen und mittels technischer Geräte (z.B. Extrusion, Sprühturm, Wirbelschicht) als wasserdispergierbare oder wasserlösliche Granulate hergestellt. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. Die Formulierung hat einen Wirkstoffgehalt von 50 Gew.-%.F Water-dispersible and water-soluble granules (WG, SG) 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing 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.
G Wasserdispergierbare und wasserlösliche Pulver (WP, SP, SS, WS) 75 Gew.-Teile der Wirkstoffe werden unter Zusatz von 25 Gew.-Teilen Dispergier- und Netzmitteln sowie Kieselsäuregel in einer Rotor-Strator Mühle vermählen. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. Der Wirkstoffgehalt der Formulierung beträgt 75 Gew.-%. . H GelformulierungenG Water-dispersible and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight. , H gel formulations
In einer Kugelmühle werden 20 Gew. -Teile der Wirkstoffe, 10 Gew.-Teile Dispergiermittel, 1Gew.-Teil Geliermittel und 70 Gew.-Teile Wasser oder eines organischen Lösungsmittels zu einer feinen Suspension vermählen. Bei der Verdünnung mit Wasser ergibt sich eine stabile Suspension mit 20 Gew.-% Wirkstoffgehalt.In a ball mill, 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content.
2. Produkte für die Direktapplikation2. Products for direct application
I Stäube (DP, DS) 5 Gew.-Teile der Wirkstoffe werden fein gemahlen und mit 95 Gew.-Teiien feinteiligem Kaolin innig vermischt. Man erhält dadurch ein Stäubemittel mit 5 Gew.-% Wirkstoffgehalt.I dusts (DP, DS) 5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.
J Granulate (GR1 FG, GG, MG) 0,5 Gew-Teile der Wirkstoffe werden fein gemahlen und mit 99,5 Gewichtsteilen Trägerstoffe verbunden. Gängige Verfahren sind dabei die Extrusion, die Sprühtrocknung oder die Wirbelschicht. Man erhält dadurch ein Granulat für die Direktapplikation mit 0,5 Gew.-% Wirkstoffgehalt.J Granules (GR 1 FG, GG, MG) 0.5 parts by weight of the active ingredients 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 0.5 wt .-% active ingredient content.
K ULV- Lösungen (UL)K ULV solutions (UL)
10 Gew.-Teile der Wirkstoffe werden in 90 Gew.-Teilen eines organischen Lösungsmittel z.B. XyIoI gelöst. Dadurch erhält man ein Produkt für die Direktapplikation mit 10 Gew.-% Wirkstoffgehalt.10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent, e.g. XyIoI solved. This gives a product for direct application with 10 wt .-% active ingredient content.
Für die Saatgutbehandlung werden üblicherweise wasserlösliche Konzentrate (LS), Suspensionen (FS), Stäube (DS), wasserdispergierbare und wasserlösliche Pulver (WS, SS), Emulsionen (ES), emulgierbare Konzentrate (EC) und Gelformulierungen (GF) verwendet. Diese Formulierungen können auf das Saatgut unverdünnt oder, bevorzugt, verdünnt angewendet werden. Die Anwendung kann vor der Aussaat erfolgen.For seed treatment, water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF) are usually used. These formulations can be applied to the seed undiluted or, preferably, diluted. The application can be done before sowing.
Bevorzugt werden FS Formulierungen für die Saatgutbehandlung verwendet. Üblicherweise enthalten solche Formulierungen 1 bis 800 g/l Wirkstoff, 1 bis 200 g/l Tenside, 0 bis 200 g/l Frostschutzmittel, 0 bis 400 g/l Bindemittel, 0 bis 200 g/l Farbstoffe und Lösungsmittel, vorzugsweise Wasser.Preference is given to using FS formulations for seed treatment. Typically, such formulations contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubmitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich ganz nach den Ver- wendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The active compounds can be used as such, in the form of their formulations or the use 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 be applied. The forms of application are based entirely on the application purposes; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netz- baren Pulvern (Spritzpulver, Öldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermitttel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und even- tuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water. For the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare from active substance wetting, adhesion, dispersing or emulsifying agents and any solvents or oil concentrates which are suitable for dilution with water.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10%, vorzugsweise zwischen 0,01 und 1%.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%.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.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.
Zu den Wirkstoffen können Öle verschiedenen Typs, Netzmittel, Adjuvants, Herbizide, Fungizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel können zu den erfindungsgemäßen Mitteln im Gewichtsverhältnis 1 :100 bis 100:1 , bevorzugt 1:10 bis 10:1 zugemischt werden.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.
Als Adjuvants in diesem Sinne kommen insbesondere in Frage: organisch modifizierte Polysiloxane, z.B. Break Thru S 240®; Alkoholalkoxylate, z. B. Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® und Lutensol ON 30®; EO-PO-Blockpolymerisate, z. B. Pluro- nie RPE 2035® und Genapol B®; Alkoholethoxylate, z. B. Lutensol XP 80®; und Natri- umdioctylsulfosuccinat, z. B. Leophen RA®.As 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- never RPE 2035 and Genapol ® B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
Die Verbindungen I und II, bzw. die Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer fungizid wirksamen Menge der Mischung, bzw. der Verbindungen I und Il bei getrennter Ausbringung, behandelt. Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen. Die fungizide Wirkung der Verbindung und der Mischungen ließ sich durch folgende Versuche zeigen:The compounds I and II, or the mixtures or the corresponding formulations, are applied by mixing the harmful fungi, the plants, seeds, soils, areas, materials or spaces to be kept free of them with a fungicidally effective amount of the mixture or of the compounds I and II when applied separately. The application can be made 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:
Wirkstoffaufbereitungdrug treatment
Für die Mikrotittertests wurden die Wirkstoffe getrennt als Stammlösung formuliert mit einer Konzentration von 10.000 ppm in DMSO. Der Wirkstoff Fluazinam wurde als handelsübliche Formulierung verwendet und mit Wasser auf die Stammlösungskonzentration von 10.000 ppm vorverdünnt.For the microtiter tests, the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO. The active ingredient fluazinam was used as a commercially available formulation and prediluted with water to the stock solution concentration of 10,000 ppm.
Die Wirkstoffe wurden getrennt oder gemeinsam als eine Stammlösung aufbereitet mit 25 mg Wirkstoff, welcher mit einem Gemisch aus Aceton und/oder DMSO und dem Emulgator Uniperol® EL (Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) im Volumen-Verhältnis Lösungsmittel-Emulgator von 99 zu 1 ad 10 ml aufgefüllt wurde. Anschließend wurde ad 100 ml mit Wasser aufgefüllt. Diese Stammlösung wurde mit dem beschriebenen Lösungsmittel-Emulgator-Wasser Gemisch zu der unten angegeben Wirkstoffkonzentration verdünnt. Der Wirkstoff Fluazinam wurde als handelsübliche Formulierung verwendet und mit Wasser auf die angegebenen Konz. verdünnt.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. The active ingredient Fluazinam was used as a commercial formulation and diluted with water to the specified conc.
Auswertungevaluation
In den Mikrotittertests wurden die gemessenen Parameter mit dem Wachstum der wirkstofffreien Kontrollvariante und dem pilz- und wirkstofffreien Leerwert verrechnet, um das relative Wachstum in % der Pathogene in den einzelnen Wirkstoffen zu ermitteln.In the microtiter tests, the measured parameters were compared with the growth of the drug-free control variant and the fungus-free and active substance-free blank to determine the relative growth in% of the pathogens in the individual active ingredients.
In den Gewächshausversuchen wurden die visuell ermittelten Werte für den Prozentanteil befallener Blattflächen in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet:In the greenhouse experiments, the visually determined values for the percentage of affected leaf areas were converted into efficiencies as% of the untreated control:
Der Wirkungsgrad (W) wird nach der Formel von Abbot wie folgt berechnet:The efficiency (W) is calculated according to the formula of Abbot as follows:
W = (1 - σ/jff) - 100W = (1 - σ / jff) - 100
a entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in %a corresponds to the fungal infestation of the treated plants in% and ß corresponds to the fungal infestation of the untreated (control) plants in%
Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 weisen die behandelten Pflanzen keinen Befall auf. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby- Formel (Colby, S. R. (Calculating synergistic and antagonistic responses of herbicide Combinations", Weeds, 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen.With an efficiency of 0, the infestation of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants have no infestation. The expected efficiencies for drug combinations were determined according to the Colby formula (Colby, SR (Calculating synergistic and antagonistic responses of herbicidal combinations), Weeds, 15, pp. 20-22, 1967) and compared with the observed efficiencies.
Colby Formel:Colby formula:
E = x + y - x-y/100E = x + y - x-y / 100
E zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b x der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs A in der Konzentration a y der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration bE expected efficiency, expressed as% of untreated control, using the mixture of active substances A and B at concentrations a and bx the efficiency expressed as% of untreated control, when using active substance A at the concentration ay the efficiency, expressed as% of untreated control, when using active substance B in concentration b
Anwendungsbeispiel 1 - Aktivität gegen den Verursacher der Grauschimmel Botrytis ci- nerea im Mikrotitter-TestUse Example 1 Activity Against the Causative Agent of Gray Mold Botrytis cinerea in the Microtiter Test
Die Stammlösungen wurden dem Verhältnis entsprechend gemischt, in eine Mikrotit- terplatte (MTP) pipettiert und mit einem wäßrigen Pilznährmedium auf Malzbasis auf die angegebene Wirkstoffkonzentration verdünnt. Anschließend erfolgte die Zugabe einer wäßrigen Sporensuspension von Botrytis cinerea. Die Platten wurden in einer wasserdampf-gesättigten Kammer bei Temperaturen von 18°C aufgestellt. Mit einem Absorptionsphotometer wurden die MTPs am 7. Tag nach der Inokulation bei 405 nm vermessen.The stock solutions were mixed according to the ratio, pipetted into a microtiter plate (MTP) and diluted with an aqueous fungus nutrient medium based on malt to the stated active compound concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. Using an absorption photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
Die gemessenen Parameter wurden mit dem Wachstum der wirkstofffreien Kontrollvariante und dem pilz- und wirkstofffreien Leerwert verrechnet, um das relative Wachstum in % der Pathogene in den einzelnen Wirkstoffen zu ermitteln.The measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
Anwendungsbeispiel 2 - Aktivität gegen die Krautfäule an Tomaten verursacht durch Phy- tophthora infestans bei protektiver BehandlungUse Example 2 - Activity against tomato late blight caused by Phytophthora infestans in protective treatment
Blätter von getopften Tomatenpflanzen wurden mit einer wäßriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. 5 Tage später wurden die Blätter mit einer wäßrigen Sporangienaufschwemmung von Phytophthora infestans infiziert. Anschließend wurden die Pflanzen in einer wasserdampf-gesättigten Kammer bei Temperaturen zwischen 18 und 20°C aufgestellt. Nach 6 Tagen hatte sich die Krautfäule auf den unbehandelten, jedoch infizierten Kontrollpflanzen so stark entwickelt, daß der Befall visuell in % ermittelt werden konnte.Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below. Five days later, the leaves were infected with an aqueous sporangia suspension of Phytophthora infestans. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° 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%.
Aus den Ergebnissen der Versuche geht hervor, dass die erfindungsgemäßen Mi- schungen aufgrund des Synergismus erheblich besser wirksam sind, als nach der CoI- by-Formel vorausberechnet. The results of the experiments show that the mixtures according to the invention are considerably more effective due to the synergism than predicted according to the CoI by formula.

Claims

Patentansprüche claims
1. Fungizide Mischungen zur Bekämpfung von pflanzenpathogenen Schadpilzen, enthaltend zwei aktive Komponenten:1. Fungicidal mixtures for controlling phytopathogenic harmful fungi containing two active components:
1) das Strobilurinderivat der Formel I,1) the strobilurin derivative of the formula I,
und and
2) mindestens einen Wirkstoff Il ausgewählt aus der Gruppe heterocyclischer2) at least one active ingredient II selected from the group of heterocyclic
Verbindungen:Links:
Fluazinam, Pyrifenox,Fluazinam, pyrifenox,
Bupirimate, Cyprodinil, Fenarimol, Ferimzone, Mepanipyrim, Nuarimol, Py- rimethanil,Bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil,
Triforine,triforine,
Fenpiclonil, Fludioxonil,Fenpiclonil, fludioxonil,
Aldimorph, Dodemorph, Fenpropimorph, Tridemorph,Aldimorph, dodemorph, fenpropimorph, tridemorph,
Fenpropidin, Iprodione, Procymidone, Vinclozolin,Fenpropidin, iprodione, procymidone, vinclozolin,
Famoxadone, Fenamidone, Octhilinone, Probenazole,Famoxadone, Fenamidone, Octhilinone, Probenazole,
5-Chlor-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluor-phenyI)-[1 ,2,4]tri- azolo[1 ,5-a]pyrimidin,5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluoro-phenyl) - [1,2,4] triazolo [1,5-a] pyrimidine .
Anilazin, Diclomezine, Pyroquilon, Proquinazid, Tricyclazole, 2-Butoxy-6-iodo-3-propyl-chromen-4-on,Anilazine, diclomezine, pyroquilone, proquinazide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one,
Acibenzolar-S-methyl, Captafol, Captan, Dazomet, Folpet, Fenoxanil, Quin- oxyfen,Acibenzolar-S-methyl, Captafol, Captan, Dazomet, Folpet, Fenoxanil, Quinoxyfen,
3-(3-Brom-6-fIuor-2-methyl-indol-1 -sulfonyl)-[1 ,2,4]triazol-1 -sulfonsäure- dimethylamid, δ-Chlor-β-phenyl-T-heterocyclylamino-triazolopyrimidine der Formel H-A,3- (3-Bromo-6-fluoro-2-methyl-indol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide, δ-chloro-β-phenyl-T-heterocyclylamino-triazolopyrimidines the formula HA,
. ii-A in der, ii-A in the
D zusammen mit dem Stickstoffatom einen Pyrrolidin-, Piperidin- oder Azepinring bildet, welche Ringe unsubstituiert sind oder durch eine oder zwei Methyl gruppen oder durch eine Ethyl, Propyl oder Butyl- gruppe substituiert sind; undD together with the nitrogen atom forms a pyrrolidine, piperidine or azepine ring, which rings are unsubstituted or substituted by one or two methyl groups or by an ethyl, propyl or butyl group; and
L Methyl, Fluor oder Chlor bedeutet;L is methyl, fluorine or chlorine;
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
2. Fungizide Mischungen gemäß Anspruch 1 , enthaltend die Verbindung der Formel I und einen Wirkstoff Il in einem Gewichtsverhältnis von 100:1 bis 1 :100.2. Fungicidal mixtures according to claim 1, containing the compound of formula I and an active ingredient II in a weight ratio of 100: 1 to 1: 100.
3. Mittel, enthaltend einen flüssigen oder festen Trägerstoff und eine Mischung gemäß Ansprüchen 1 oder 2.3. A composition containing a liquid or solid carrier and a mixture according to claims 1 or 2.
4. Verfahren zur Bekämpfung von pflanzenpathogenen Schadpilzen, dadurch gekennzeichnet, dass man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Pflanzen, den Boden oder Saatgüter mit einer wirksamen Menge der Verbindung I und eines Wirkstoffs Il gemäß Anspruch 1 behandelt.4. A method for controlling phytopathogenic harmful fungi, which comprises treating the fungi, their habitat or the plants to be protected against fungal attack, the soil or seeds with an effective amount of the compound I and an active compound II according to claim 1.
5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, dass man die Verbindungen I und Il gemäß Anspruch 1 gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander ausbringt.5. The method according to claim 4, characterized in that the compounds I and II according to claim 1 at the same time, and jointly or separately, or successively auszustingt.
6. Verfahren nach Ansprüchen 4 oder 5, dadurch gekennzeichnet, dass man die6. Process according to claims 4 or 5, characterized in that the
Verbindungen I und Il gemäß Anspruch 1 oder die Mischung gemäß Ansprüchen 1 oder 2 in einer Menge von 5 g/ha bis 2000 g/ha aufwendet.Compounds I and II according to claim 1 or the mixture according to claims 1 or 2 in an amount of 5 g / ha to 2000 g / ha.
7. Verfahren nach Ansprüchen 4 oder 5, dadurch gekennzeichnet, dass man die Verbindungen I und Il gemäß Anspruch 1 oder die Mischung gemäß Ansprüchen7. The method according to claims 4 or 5, characterized in that the compounds I and II according to claim 1 or the mixture according to claims
1 oder 2 in einer Menge von 1 bis 1000 g/100 kg Saatgut anwendet.1 or 2 in an amount of 1 to 1000 g / 100 kg seed applies.
8. Saatgut, enthaltend die Mischung gemäß Ansprüchen 1 oder 2 in einer Menge von 1 bis 1000 g/100 kg.8. Seed containing the mixture according to claims 1 or 2 in an amount of 1 to 1000 g / 100 kg.
9. Verwendung der Verbindungen I und Il gemäß Anspruch 1 zur Herstellung eines zur Bekämpfung von Schadpilzen geeigneten Mittels. 9. Use of the compounds I and II according to claim 1 for the preparation of a suitable agent for controlling harmful fungi.
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EP1424479A1 (en) 2002-11-28 2004-06-02 STMicroelectronics S.r.l. Electronic device architecture for determining the angular position of an engine shaft in internal combustion engines

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