WO2005053404A1 - Melanges fongicides a base de derives de benzamidoxime - Google Patents

Melanges fongicides a base de derives de benzamidoxime Download PDF

Info

Publication number
WO2005053404A1
WO2005053404A1 PCT/EP2003/013183 EP0313183W WO2005053404A1 WO 2005053404 A1 WO2005053404 A1 WO 2005053404A1 EP 0313183 W EP0313183 W EP 0313183W WO 2005053404 A1 WO2005053404 A1 WO 2005053404A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
iii
weight
parts
compound
Prior art date
Application number
PCT/EP2003/013183
Other languages
German (de)
English (en)
Inventor
Eberhard Ammermann
Reinhard Stierl
Ulrich Schöfl
Siegfried Strathmann
Klaus Schelberger
Maria Scherer
Egon Haden
Original Assignee
Basf Aktiengesellschaft
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
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU2003289891A priority Critical patent/AU2003289891A1/en
Priority to PCT/EP2003/013183 priority patent/WO2005053404A1/fr
Publication of WO2005053404A1 publication Critical patent/WO2005053404A1/fr

Links

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

Definitions

  • the present invention relates to
  • R is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy
  • the invention also relates to a process for combating harmful fungi with mixtures of the compound I with at least one of the compounds II to III and the use of the compound I with at least one of the compounds II to III for the production of such mixtures and agents which contain these mixtures.
  • 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 such as 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. Preferably 1 to 3 halogen atoms are present, the difluoromethane / - or the trifluoromethyl group being particularly preferred.
  • halogen atoms in particular fluorine and chlorine.
  • 1 to 3 halogen atoms are present, the difluoromethane / - or the trifluoromethyl group being particularly preferred.
  • 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 III.
  • Benzamide oxime derivative and ciprodinil or proquinazide are preferably used in a weight ratio in the range from 20: 1 to 1:20, in particular 10: 1 to 1:10.
  • the mixtures of the compounds I with at least one of the compounds II to III or the compounds I and at least one of the compounds II to III used simultaneously, together or separately are notable for an outstanding action against a broad spectrum of phytopathogenic fungi the class of Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes. They are partly systemically effective and can therefore also be used as leaf and soil fungicides.
  • the mixtures according to the invention can particularly preferably be used to control powdery mildew fungi in cereal, vine and vegetable crops and in ornamental plants.
  • the compound I and at least one of the compounds II to III 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 control success.
  • the application rates of the mixtures according to the invention 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 III 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 the 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 compounds I and at least one of the compounds II to III or their mixtures of the compounds I and at least one of the compounds are administered separately or together Compounds II to III by spraying or dusting the seeds, plants or soils 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 III 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, scattering agents or granules are prepared and used by spraying, atomizing, dusting, scattering or pouring.
  • the form of application depends on the intended use; in any case, it should ensure as fine and uniform a distribution of the mixture according to the invention as possible.
  • 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, and in the case of water as 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), a ine (e.g.
  • Ethanolamine, dimethylformamide) and water such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfit
  • Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compound I or II to III or the mixture of the compounds I and at least one of the compounds II to III with a solid carrier.
  • Granules e.g. coated, impregnated or homogeneous granules
  • a solid carrier e.g., a maltitol
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers 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.
  • mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers such as ammonium sulfate, ammonium phosphate, ammonium
  • 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 III or the mixture of the compounds I and at least one of the compounds II to III.
  • 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 III, 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 by them are mixed with a fungicidally effective amount of the mixture, or the compounds I and at least one of the compounds II to III treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • V a mixture of 80 parts by weight 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 lignosulfonic acid from a sulfite blue acid and 7 parts by weight, ground in a hammer mill.
  • 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 of a paraffinic mineral oil.
  • the synergistic effect of the mixtures according to the invention can be demonstrated by the following experiments:
  • 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.
  • ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack 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.
  • Leaves of "Kanzler" wheat seedlings grown in pots were sprayed to runoff point in aqueous suspension in the combination of active ingredients specified below.
  • the suspension or emulsion was prepared from a stock solution with 10% active ingredient in a mixture consisting of 70% cyclohexanone, 20% wetting agent and 10% emulsifier. 24 hours after the spray coating has dried on, spores of powdery mildew (Erysiphe [syn. Blumeria] graminisforma specialis. Tritic) stäubt.
  • the test plants were then placed in the greenhouse at a temperature between 20 and 24 ° C and 60 to 90% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area.
  • the active substances were prepared separately or together as a stock solution with 0.25% by weight of active substance in acetone or
  • DMSO methyl methoxylated methylcellulose
  • emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the suspension or emulsion was prepared as described above. 20 hours after the spray coating had dried on, the plants were inoculated with an aqueous spore suspension of cucumber powdery mildew (Sphaerotheca fuliginea). The plants were then cultivated in a greenhouse at temperatures between 20 and 24 ° C. and 60 to 80% relative atmospheric humidity for 7 days. The extent of mildew development was then determined visually in% of the cotyledon area. The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control.
  • Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%.
  • the expected efficacies for combinations of active substances were determined using the Colby formula (Colby, SR (Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies.

Landscapes

  • 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

Mélanges fongicides renfermant, comme composants actifs, (1) un dérivé de benzamidoxime de formule (I), dans laquelle le substituant et l'indice peuvent avoir les significations suivantes : R : hydrogène, halogène, alkyle en C1-C4, halogénoalkyle en C1-C4, alcoxy en C1-C4 ou halogéno-alcoxy en C1-C4, n = 1, 2 ou 3, et (2) un cyprodinile de formule (II), ou (3) un proquinazide de formule (III), en une quantité efficace au point de vue synergique..
PCT/EP2003/013183 2003-11-24 2003-11-24 Melanges fongicides a base de derives de benzamidoxime WO2005053404A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003289891A AU2003289891A1 (en) 2003-11-24 2003-11-24 Fungicide mixtures based on benzamidoxime derivatives
PCT/EP2003/013183 WO2005053404A1 (fr) 2003-11-24 2003-11-24 Melanges fongicides a base de derives de benzamidoxime

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2003/013183 WO2005053404A1 (fr) 2003-11-24 2003-11-24 Melanges fongicides a base de derives de benzamidoxime

Publications (1)

Publication Number Publication Date
WO2005053404A1 true WO2005053404A1 (fr) 2005-06-16

Family

ID=34639221

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/013183 WO2005053404A1 (fr) 2003-11-24 2003-11-24 Melanges fongicides a base de derives de benzamidoxime

Country Status (2)

Country Link
AU (1) AU2003289891A1 (fr)
WO (1) WO2005053404A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997040685A1 (fr) * 1996-04-26 1997-11-06 Basf Aktiengesellschaft Melanges fongicides
EP1077028A1 (fr) * 1998-04-30 2001-02-21 Nippon Soda Co., Ltd. Composition bactericide pour l'agriculture et l'horticulture
WO2003084329A1 (fr) * 2002-04-05 2003-10-16 Basf Aktiengesellschaft Melanges fongicides a base de derives de benzamidoxime et d'un derive de strobilurine
DE10252657A1 (de) * 2002-11-11 2004-05-27 Basf Ag Fungizide Mischungen auf der Basis von Benzamidoxim-Derivaten

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997040685A1 (fr) * 1996-04-26 1997-11-06 Basf Aktiengesellschaft Melanges fongicides
EP1077028A1 (fr) * 1998-04-30 2001-02-21 Nippon Soda Co., Ltd. Composition bactericide pour l'agriculture et l'horticulture
WO2003084329A1 (fr) * 2002-04-05 2003-10-16 Basf Aktiengesellschaft Melanges fongicides a base de derives de benzamidoxime et d'un derive de strobilurine
DE10252657A1 (de) * 2002-11-11 2004-05-27 Basf Ag Fungizide Mischungen auf der Basis von Benzamidoxim-Derivaten

Also Published As

Publication number Publication date
AU2003289891A1 (en) 2005-06-24

Similar Documents

Publication Publication Date Title
EP1201126B1 (fr) Mélanges fongicides à base de composés pyridine carboxamide
EP1039805B1 (fr) Melanges fongicides a base de composes amide
EP1039800B1 (fr) Melanges fongicides a base de composes pyridine carboxamide
EP1494531A1 (fr) Melanges fongicides a base de derives de benzamidoxime et d'azoles
EP1039806B1 (fr) Melanges fongicides a base d'amides de pyridine et de fenarimol
EP1041883B1 (fr) Melanges fongicides a base d'amides de pyridine et de derives de morpholine ou de piperidine
EP1521526B3 (fr) Melanges fongicides a base de dithianon
EP1214881B1 (fr) Mélanges fongicides à base de composés amides
WO1997015189A1 (fr) Melanges fongicides d'esters d'acide carboxylique d'oxime-ether avec des fongicides renfermant du cuivre
EP1365652A1 (fr) Melanges fongicides contenant des benzophenones et des n-biphenylnicotinamides
WO2004000019A1 (fr) Melanges fongicides a base de derives de benzamidoxime, de benzophenones et d'un azol
EP1526772B1 (fr) Melanges fongicides
EP1524904A1 (fr) Melanges fongicides
EP0892603B1 (fr) Melanges fungicides
DE10252657A1 (de) Fungizide Mischungen auf der Basis von Benzamidoxim-Derivaten
EP1524906B1 (fr) Melanges fongicides
WO2005053404A1 (fr) Melanges fongicides a base de derives de benzamidoxime
WO2002062140A1 (fr) Compositions fongicides contenant un derive de la benzophenone et un derive d'ether d'oxime
WO2004008857A1 (fr) Melanges fongicides
EP1139749A1 (fr) Melanges fongicides a base de derives de morpholine ou de piperidine et de derives d'ether-oxime
WO2002049434A1 (fr) Melanges fongicides a base de derives d'oxymethers
WO2002056685A2 (fr) Melanges fongicides
EP1355531A1 (fr) Melanges fongicides
WO2004091294A2 (fr) Melanges fongicides
WO2004091298A1 (fr) Melanges fongicides

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PG PH PL PT RO RU SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP