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WO2007031487A2 - Melanges fongicides a base de triazoles - Google Patents

Melanges fongicides a base de triazoles Download PDF

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Publication number
WO2007031487A2
WO2007031487A2 PCT/EP2006/066226 EP2006066226W WO2007031487A2 WO 2007031487 A2 WO2007031487 A2 WO 2007031487A2 EP 2006066226 W EP2006066226 W EP 2006066226W WO 2007031487 A2 WO2007031487 A2 WO 2007031487A2
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WO
WIPO (PCT)
Prior art keywords
formula
compound
mixtures
weight
acid
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.)
Ceased
Application number
PCT/EP2006/066226
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German (de)
English (en)
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WO2007031487A3 (fr
Inventor
Martin Semar
Dieter Strobel
Jens Bruns
Reinhard Stierl
Frank Werner
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BASF SE
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BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Application filed by BASF SE filed Critical BASF SE
Publication of WO2007031487A2 publication Critical patent/WO2007031487A2/fr
Anticipated expiration legal-status Critical
Publication of WO2007031487A3 publication Critical patent/WO2007031487A3/fr
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to fungicidal mixtures containing
  • the invention relates to a method for controlling harmful fungi with mixtures of the compound I with the compound II and the use of the compound I with the compound II for the preparation of such mixtures and compositions containing these mixtures.
  • Epoxiconazole of the formula I and its use as a crop protection agent is described in EP-B 0 196 038.
  • the present inventions were mixtures as an object that show an improved action against harmful fungi, especially for certain indications with reduced total amount of applied drugs.
  • the compounds I and II are able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid.
  • suitable organic acids are formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and naphthyl carry one or two phosphoric acid radicals), wherein the alkyl or alkan
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others in consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • the mixtures of the compound I and of an active compound II, or the simultaneous joint or separate use of the compound I and of an active compound II draw- Their excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Peronosporomycetes (syn. Oomycetes) and Basidiomycetes. Some of them are systemically effective and can be used in crop protection as pickling, foliar and soil fungicides.
  • Bipolaris and Drechslera species on maize, cereals, rice and turf e.g. D.maydis on corn • Blumeria graminis (powdery mildew) on cereals,
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Drechslera species Pyrenophora species on maize, cereals, rice and turf, e.g. D.teres to barley or D. tritici-repentis to wheat • Esca to grapevine, caused by Phaeoacremonium chlamydosporium, Ph.
  • Peronospora species on cabbage and bulbous plants such as P. brassicae on cabbage or P. destructor on onion
  • Phytophthora species on various plants e.g. P.capsici on paprika
  • Pseudocercosporella herpotrichoides on cereals Pseudoperonospora on various plants, e.g. P. cubensis on cucumber or P. humili on hops
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P.graminis on cereals, or P. asparagi on asparagus • Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S.atumuatum,
  • Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beet, vegetables and various plants such as e.g. R.solani on turnips and various plants,
  • Rhynchosporium secalis on barley, rye and triticale • Sclerotinia species on oilseed rape and sunflowers
  • Venturia species scab
  • apples and pears like. e.g. V. inaequalis to apple.
  • the mixtures of compound I and of an active compound II are particularly suitable for controlling harmful fungi from the class of the Peronosporomycetes (syn. ten), such as Peronospora species, Phytophthora species, Plasmopara viticola and Pseudoperonospora species, in particular the corresponding ones mentioned above.
  • the mixtures of compounds I and II are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureosidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophlum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderm spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • Compound I is used by treating the fungi or the plants, seeds, materials or soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • 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.
  • the pure active ingredients I and II are preferably used, to which other active substances can be added against harmful fungi or against other pests such as insects, spider animals or nematodes or else herbicidal or growth-regulating active substances or fertilizers.
  • mixtures of compound I and the 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 100: 1 to 1: 100, preferably 20: 1 to 1:20, in particular 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, especially in agricultural crops, depending on the nature of the compound and the desired effect at 5 g / ha to 2000 g / ha, preferably 20 to 900 g / ha, in particular 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 accordingly generally from 1 to 2000 g / ha, preferably from 10 to 1500 g / ha, in particular from 40 to 1000 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 of controlling harmful fungi is by the separate or combined application of compound I and active compound II or a mixture of compound I and active compound II by spraying or dusting the seeds, plants or soils before or after sowing the plants or before or after the 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:
  • solvents eg Solvesso products, xylene
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • acetates Glycol diacetate
  • glycols dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • - Carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite 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 octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivative
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredients.
  • the active compounds are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a compound according to the invention 10 parts by weight of a compound according to the invention are mixed 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 an active ingredient content of 10% by weight.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • a compound according to the invention 15 parts by weight of a compound according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 15% by weight.
  • a compound according to the invention 25 parts by weight of a compound according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added to 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.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine Wirkstoffsuspension sion. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • 50 parts by weight of a compound according to the invention are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • a compound of the invention 75 parts by weight of a compound of the invention are added with addition of 25 Parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of a compound according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • 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 Compounds I and II with separate application, treated.
  • the application can be made before or after the attack by the harmful fungi.
  • 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 dimethyl sulfoxide and the emulsifier Uniperol ® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Uniperol ® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the efficiency (W) is calculated according to the formula of Abbot as follows:
  • ⁇ corresponds to the fungal infestation of the treated plants in% and ⁇ corresponds to the fungal infestation of the untreated (control) plants in%
  • ⁇ 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 active ingredients were formulated separately as stock solution with a concentration of
  • the active ingredient epoxiconazole was used as a commercial formulation.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance 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. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation. The measured parameters were consistent with the growth of drug-free
  • Control variant and the fungus-free and drug-free blank to calculate the relative growth in% of the pathogens in the individual drugs.
  • the visually determined values for the percentage of affected leaf area were first averaged, then converted into efficiencies as% of the untreated control. Efficiency 0 is the same infestation as in the untreated control, efficiency 100 is 0% infestation.
  • the expected efficiencies for drug combinations were calculated according to the Colby formula (Colby, SR (Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds, ⁇ 5, pp. 20-22, 1967) and compared with the observed efficiencies.

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

Abstract

L'invention concerne des mélanges fongicides constitués (1) d'époxiconazole de formule (I) ou de ses sels ou produits d'addition et (2) d'azoxystrobine de formule (II) dans des quantités garantissant un effet synergique, un procédé de lutte contre des champignons parasites à l'aide de mélanges constitués d'un composé (I) et d'au moins un principe actif (II), l'utilisation d'un composé (I) avec des principes actifs (II) pour produire des mélanges de ce type ainsi que des agents contenant lesdits mélanges.
PCT/EP2006/066226 2005-09-14 2006-09-11 Melanges fongicides a base de triazoles Ceased WO2007031487A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005044036 2005-09-14
DE102005044036.3 2005-09-14

Publications (2)

Publication Number Publication Date
WO2007031487A2 true WO2007031487A2 (fr) 2007-03-22
WO2007031487A3 WO2007031487A3 (fr) 2008-05-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/066226 Ceased WO2007031487A2 (fr) 2005-09-14 2006-09-11 Melanges fongicides a base de triazoles

Country Status (2)

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AR (1) AR057127A1 (fr)
WO (1) WO2007031487A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102150658A (zh) * 2010-12-06 2011-08-17 北京颖新泰康国际贸易有限公司 一种杀菌剂组合物和制剂及其应用

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MERCER, P. C. ET AL: "Evaluation of a range of strobilurin and triazole fungicide spray programs on Claire winter wheat in Northern Ireland in 2000" XP002472266 gefunden im STN Database accession no. 2002:740804 & TESTS OF AGROCHEMICALS AND CULTIVARS , 22, 16-17 CODEN: TACUDC; ISSN: 0951-4309, 2001, *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TANACS, LAJOS ET AL: "Effect of herbicide and fungicide treatments on the gluten content, gluten spread and falling number of the grain yield of winter wheat varieties" XP002472268 gefunden im STN Database accession no. 2002:269300 & NOVENYTERMELES , 50(4), 407-417 CODEN: NOVEAK; ISSN: 0546-8191, 2001, *
ELCOCK ET AL.: "Potential for the development of reduced sensitivity to DMI fungicides in current control practices for Mycosphaerella graminicola in winter wheat in the UK" THE BCPC CONFERENCE-PESTS & DISEASES, 2000, Seiten 407-414, XP008089475 *
IOOS ET AL.: "Effets de fongicides sur les agents de la fusariose des épis et les mycotoxines associées. Bilan de trois années d'expérimentation en conditions de contamination naturelle menées par les Services de la Protection des Végétaux" PHYTOMA, 2003, Seiten 14-21, XP008089527 *
ROLSTON ET AL.: "Tolerance of AR1 Neotyphodium Endophyte to fungicides used in perennial ryegrass seed production" NEW ZEALAND PLANT PROTECTION, Bd. 55, 2002, Seiten 322-326, XP008089558 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102150658A (zh) * 2010-12-06 2011-08-17 北京颖新泰康国际贸易有限公司 一种杀菌剂组合物和制剂及其应用

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Publication number Publication date
WO2007031487A3 (fr) 2008-05-15
AR057127A1 (es) 2007-11-14

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