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
  • A01N37/52—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 groups, e.g. carboxylic acid amidines
• • 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
• R is hydrogen, halogen, C ⁇ -C4 alkyl, Ci - ⁇ - haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ -C 4 -haloalkoxy
• the invention relates to a method for controlling harmful fungi with mixtures of the compound I with at least one of the compounds II to XXIII and the use of the compound I with at least one of the compounds II to XXIII for the production of such mixtures and agents which contain these mixtures ,
• Fungicidal mixtures are known from EP-B 531,837, EP-A 645,091 and WO 97/06678 which contain one of the azoles II to XXIII as an active ingredient.
• the object of the present invention was to provide further means for combating harmful fungi and in particular for certain indications.
• the mixtures according to the invention act synergistically and are therefore particularly suitable for controlling harmful fungi and in particular powdery mildew in cereals, vegetables and vines.
• halogen represents fluorine, chlorine, bromine and iodine and in particular fluorine, chlorine and bromine.
• alkyl encompasses straight-chain and branched alkyl groups. These are preferably straight-chain or branched C 1 -C 4 -alkyl groups. Examples of alkyl groups are alkyl, in particular methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl.
• Haloalkyl stands for an alkyl group as defined above which is partially or completely halogenated with one or more halogen atoms, in particular fluorine and chlorine. There are preferably 1 to 3 halogen atoms, with the difluoromethane / - or the trifluoromethyl group being particularly preferred.
• alkyl group and haloalkyl group apply correspondingly to the alkyl and haloalkyl groups in alkoxy and haloalkoxy.
• the radical R in the formula I preferably represents a hydrogen atom.
• the mixtures according to the invention contain at least one compound of the formula II to XXIII as the azole derivative.
• Benzamide oxime derivative of the formula I is sufficient.
• Benzamide oxime derivative and azole are preferably used in a weight ratio in the range from 20: 1 to 1:20, in particular 10: 1 to 1 : 10 used. Because of the basic character of the nitrogen atoms contained in them, the azoles II-XXIII are able to form salts or adducts with inorganic or organic acids or with metal ions.
• inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid.
• organic acids are formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with straight-chain alkyl radicals) 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 which carry one or two phosphoric acid residues), where the Al yl or aryl residues can carry
• the ions of the elements of the first to eighth subgroups especially chromium, manganese, iron, cobalt, nickel, copper, zinc and, in addition, of the second main group, especially calcium and magnesium, of the third and fourth main group come as metal ions Aluminum, tin and lead are considered.
• the metals can, if appropriate, be present in various valencies to which they are assigned.
• Mixtures of the benzamide oxime derivative of the formula I with diniconazole are preferred. Mixtures of the benzamide oxime derivative of the formula I with epoxiconazole are preferred.
• Mixtures of the benzamide oxime derivative of the formula I with ipconazole are preferred. Mixtures of the benzamide oxime derivative of the formula I with triticonazole are preferred.
• the mixtures of the compounds I with at least one of the compounds II to XXIII or the compounds I and at least one of the compounds II to XXIII used simultaneously, together or separately are notable for an outstanding action against a broad spectrum of phytopathogenic fungi, in particular the class of Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes. They are partly systemically effective and can therefore also be used as leaf and soil fungicides.
• XXIII can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
• the application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 kg / ha, depending on the type of effect desired ,
• the application rates for the compounds I are 0.01 to 2.5 kg / ha, preferably 0.05 to 2.5 kg / ha, in particular 0.1 to 1.0 kg / ha.
• the application rates for the compounds II to XXIII are accordingly from 0.01 to 10 kg / ha, preferably 0.05 to 5 kg / ha, in particular 0.05 to 2.0 kg / ha.
• application rates of mixture of 0.001 to 250 g / kg of seed preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg, are generally used.
• the separate or joint application of the compounds I and at least one of the compounds II to XXIII or their mixtures of the compounds I and at least one of the compounds II to XXIII is carried out 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 fungicidal synergistic mixtures according to the invention or the compound I and at least one of the compounds II to XXIII can be used, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, Dusts, sprays or granules are prepared and applied by spraying, atomizing, dusting, scattering or pouring.
• the form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible.
• the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
• auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
• Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
• natural stone powder eg kaolins, clays, talc, chalk
• synthetic stone powder eg highly disperse silica, silicates
• Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
• alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives - aldehyde, condensation products of naphthalene or
• Naphthalenesulfonic acids with phenol and formaldehyde polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol, ethylene oxide condensate, ethoxyalkylene glycol ethylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxyethylene glycol, ethoxyalkylene glycol ethoxylate, ethoxyalkylene glycol ethoxylate, ethoxylated castor oil, ethoxylated castor oil -Sulfite waste or methyl cellulose into consideration.
• Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the compound I or II to XXIII or the mixture of the compounds I and at least one of the compounds II to XXIII with a solid carrier.
• Granules e.g. coating, impregnation or homogeneous granules
• a solid carrier e.g., a wax, a wax, or a wax.
• Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolo- serve as fillers or solid carriers.
• diatomaceous earth calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
• the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I or II to XXIII or the mixture of the compounds I and at least one of the compounds II to XXIII.
• the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum).
• the compounds I or II to XXIII, the mixtures or the corresponding formulations are used in such a way that the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free from them are mixed with a fungicidally effective amount of the mixture, or of the compounds I and at least one of the compounds II to XXIII treated separately.
• the application can take place before or after the infestation by the harmful fungi.
• V a mixture of 80% by weight ground in a hammer mill Parts of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite liquor and 7 parts by weight of powdered silica gel; a spray mixture is obtained by finely distributing the mixture in water; VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dust contains 3% by weight of active ingredient; VII.
• Active ingredients 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;
• IX a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 88 parts by weight -Share a paraffinic mineral oil.
• the active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
• the evaluation is carried out by determining the affected leaf areas in percent. These percentages are converted into efficiencies.
• the efficiency (W) is determined according to Abbot's formula as follows: ⁇
• ⁇ • corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal infection of the untreated (control) plants in%
• the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
• Example of use 1 Activity against powdery mildew caused by Erysiphe [syn. Blumeria.] Graminis forma specialis. tri tici
• Example of use 2 Curative activity against wheat brown rust caused by Puccinia recondi ta

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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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• 2003
  • 2003-04-02 US US10/509,797 patent/US20050148547A1/en not_active Abandoned
  • 2003-04-02 EP EP03722384A patent/EP1494531A1/de not_active Withdrawn
  • 2003-04-02 IL IL16405003A patent/IL164050A0/xx unknown
  • 2003-04-02 JP JP2003581587A patent/JP2005527568A/ja active Pending
  • 2003-04-02 MX MXPA04009018A patent/MXPA04009018A/es not_active Application Discontinuation
  • 2003-04-02 PL PL03371854A patent/PL371854A1/xx not_active Application Discontinuation
  • 2003-04-02 EA EA200401291A patent/EA200401291A1/ru unknown
  • 2003-04-02 BR BR0308830-8A patent/BR0308830A/pt not_active IP Right Cessation
  • 2003-04-02 WO PCT/EP2003/003432 patent/WO2003084330A1/de not_active Application Discontinuation
  • 2003-04-02 AU AU2003229594A patent/AU2003229594A1/en not_active Abandoned
  • 2003-04-02 CA CA002480701A patent/CA2480701A1/en not_active Abandoned
  • 2003-04-02 KR KR10-2004-7015762A patent/KR20040097274A/ko not_active Application Discontinuation
  • 2003-04-02 CN CNA038078627A patent/CN1646014A/zh active Pending
  • 2003-04-04 AR ARP030101192A patent/AR039263A1/es unknown
• 2004
  • 2004-11-04 ZA ZA200408921A patent/ZA200408921B/en unknown

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