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)

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• 2005
  • 2005-12-16 PE PE2005001498A patent/PE20060801A1/es not_active Application Discontinuation
  • 2005-12-21 EP EP05824381A patent/EP1830645A1/de not_active Withdrawn
  • 2005-12-21 CA CA002590311A patent/CA2590311A1/en not_active Abandoned
  • 2005-12-21 US US11/793,793 patent/US20090124599A1/en not_active Abandoned
  • 2005-12-21 MX MX2007006800A patent/MX2007006800A/es not_active Application Discontinuation
  • 2005-12-21 BR BRPI0519698-1A patent/BRPI0519698A2/pt not_active IP Right Cessation
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  • 2005-12-21 KR KR1020077016641A patent/KR20070093121A/ko not_active Application Discontinuation
  • 2005-12-21 WO PCT/EP2005/013780 patent/WO2006069699A1/de active Application Filing
  • 2005-12-21 CN CNA2005800446882A patent/CN101087523A/zh active Pending
  • 2005-12-22 AR ARP050105512A patent/AR052183A1/es unknown
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• 2007
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