EP1353558A2 - Melanges fongicides - Google Patents

Melanges fongicides

Info

Publication number
EP1353558A2
EP1353558A2 EP02715416A EP02715416A EP1353558A2 EP 1353558 A2 EP1353558 A2 EP 1353558A2 EP 02715416 A EP02715416 A EP 02715416A EP 02715416 A EP02715416 A EP 02715416A EP 1353558 A2 EP1353558 A2 EP 1353558A2
Authority
EP
European Patent Office
Prior art keywords
formula
phenylacetic acid
halogen
compounds
derivatives
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Withdrawn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
EP02715416A
Other languages
German (de)
English (en)
Inventor
Thomas Grote
Arne Ptock
Eberhard Ammermann
Reinhard Stierl
Gisela Lorenz
Siegfried Strathmann
Maria Scherer
Klaus Schelberger
Egon Haden
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
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 SE filed Critical BASF SE
Publication of EP1353558A2 publication Critical patent/EP1353558A2/fr
Withdrawn legal-status Critical Current

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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to fungicidal mixtures comprising
  • R 1 and R 2 are halogen and phenyl, which may be substituted by halogen or -CC alkyl, or
  • R 4 di- (-C 4 alkyl) amino or
  • Isoxazol-4-yl which can carry two -CC alkyl radicals mean
  • the invention relates to methods for controlling harmful fungi with mixtures of the compounds I and II (Ila to III) and the use of the compounds I and the compounds II for the preparation of such mixtures.
  • the present invention was based on mixtures which, with a reduced total amount of active compounds applied, have an improved activity against harmful fungi (synergistic mixtures).
  • Formula I in particular represents imidazole derivatives of the formula I in which R 1 is halogen, in particular chlorine and R 2 is tolyl, in particular p-tolyl. Equally preferred are compounds of the formula I in which R 4 is dimethylamino.
  • the compound of the formula Ia (common name: cyazofamid) is particularly preferred. It is known from EP-A 298 196.
  • Halogen stands for fluorine, chlorine, bromine and iodine.
  • Compounds of the formula Ib in which X represents bromine (Ib.l) or chlorine (Ib.2) are particularly preferred.
  • the two-component mixtures containing an idazole derivative I and a phenylacetic acid derivative II are preferred.
  • mixtures of the compound Ia with a phenylacetic acid derivative from the group of the formulas Ila to Ile are particularly preferred.
  • the compounds I and II are capable of forming salts or adducts with inorganic or organic acids or with metal ions.
  • inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids for example formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and glycolic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, p-toluenesulfonic acid, salicylic acid, p-Aminosalizyl- acid, 2-phenoxybenzoic, 2 -Acetoxybenzoic acid in question.
  • acetic acid trifluoroacetic acid, trichloroacetic acid and propionic acid and glycolic acid
  • lactic acid succinic acid, citric acid
  • benzoic acid cinnamic acid, oxalic acid, p-toluenesulfonic acid, salicylic acid, p-Aminosalizyl- acid, 2-phenoxybenzoic, 2 -Acetoxybenzoic acid in question.
  • the ions of the elements chromium, manganese, iron, cobalt, nickel, copper, zinc, calcium, magnesium, aluminum, tin and lead are particularly suitable as metal ions.
  • the metals can, if appropriate, be present in various valences which they can assume.
  • the mixtures of the compounds I and II or the compounds I and II used simultaneously, together or separately, are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes out. They are partly systemically effective and can therefore also be used as leaf and soil fungicides.
  • the compounds I and II 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 compounds I and II are usually used in a weight ratio of 20: 1 to 1: 200, in particular 10: 1 to 1: 100, preferably 5: 1 to 1:50.
  • 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 0.1 to 3.0 kg / ha, depending on the type of effect desired ,
  • the application rates for the compounds I are 0.01 to 1 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • the application rates for the compounds II are accordingly from 0.01 to 1 kg / ha, preferably 0.02 to 0.5 kg / ha, in particular 0.05 to 0.3 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 compounds I and II or the mixtures of the compounds I and II are applied separately or together by spraying or dusting the seeds, the plants or the soil before or after the plants are sown or before or after the plants emerge.
  • the fungicidal synergistic mixtures according to the invention or the compounds I and II can, for example, in the form of di ⁇ sprayable solutions, powders and suspensions or in the form prepared from high-proof aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents or granules 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 manner known per se, e.g. by adding solvents and / or carriers. Inert additives such as emulsifiers or dispersants are usually added to the formulations.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin-,
  • Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compounds I or II or the mixture of the compounds I and II 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 soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, 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 pro 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 or of the mixture of the compounds I and II.
  • the active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum) is used.
  • the compounds I or II, 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 of them are mixed with a fungicidally effective amount of the mixture, or of compounds I and II treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • the active ingredients were 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 was carried out by determining the infected
  • ⁇ 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.
  • the expected efficacies of the active ingredient mixtures were determined using the Colby formula [RS Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficiencies.
  • Leaves of potted plants of the "large meat tomato St. Pierre" were sprayed to runoff point with an aqueous suspension which was prepared from a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5% emulsifier. The following day, the leaves were infected with a cold aqueous zoo spore suspension of Phytophthora infestans with a density of 0.25 x 10 6 spores / ml. The plants were then placed in a steam-saturated chamber at temperatures between 18 and 20 ° C. After 6 days, the blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.

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

L'invention concerne des mélanges fongicides contenant A) des dérivés d'imidazole de formule (I) dans laquelle R<1> et R<2> désignent halogène et phényle, qui peut être substitué par halogène ou alkyle, ou bien R<1> et R<2> forment avec la double liaison C=C de pontage un groupe 3,4-difluorométhylène dioxyphényl; R<3> signifie cyano ou halogène ; et R<4> désigne di-(alkyle C1-C4) amino ou isoxazol-4-yle, lequel peut porter deux restes alkyle C1-C4; et B) au moins un dérivé d'acide phénylacétique II sélectionné dans le groupe des formules (IIa) à (IIe), en quantité synergiquement active. La présente invention porte également sur des procédés pour lutter contre des champignons nocifs au moyen de mélanges des composés I et II (IIa à IIe) et sur des agents les contenant.
EP02715416A 2001-01-16 2002-01-12 Melanges fongicides Withdrawn EP1353558A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10101921 2001-01-16
DE10101921 2001-01-16
PCT/EP2002/000237 WO2002054870A2 (fr) 2001-01-16 2002-01-12 Mélanges fongicides

Publications (1)

Publication Number Publication Date
EP1353558A2 true EP1353558A2 (fr) 2003-10-22

Family

ID=7670835

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02715416A Withdrawn EP1353558A2 (fr) 2001-01-16 2002-01-12 Melanges fongicides

Country Status (5)

Country Link
US (1) US20040029944A1 (fr)
EP (1) EP1353558A2 (fr)
JP (1) JP2004525880A (fr)
BR (1) BR0206451A (fr)
WO (1) WO2002054870A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL219699B1 (pl) 2002-03-21 2015-06-30 Basf Ag Mieszanina grzybobójcza zawierająca protiokonazol i prochloraz, sposób zwalczania szkodliwych grzybów i środek grzybobójczy
JP4431495B2 (ja) * 2002-07-17 2010-03-17 ビーエーエスエフ ソシエタス・ヨーロピア ジチアノンに基づく殺菌混合物
UA80509C2 (en) * 2004-03-30 2007-09-25 Basf Ag Fungicidal mixture, means, method for control, sowing material and use of compounds
CA2589646A1 (fr) * 2004-12-20 2006-06-29 Basf Aktiengesellschaft Procede pour lutter contre les mycoses chez les legumineuses
CN103918658B (zh) * 2014-04-24 2015-08-12 深圳诺普信农化股份有限公司 一种含有氰霜唑的复配杀菌组合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PH11991042549B1 (fr) * 1990-06-05 2000-12-04
SK15898A3 (en) * 1995-08-10 1998-06-03 Bayer Ag Halobenzimidazoles and their use as microbicides
DE19539324A1 (de) * 1995-10-23 1997-04-24 Basf Ag Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
DE19716256A1 (de) * 1997-04-18 1998-10-22 Bayer Ag Fungizide Wirkstoffkombinationen
US20020072535A1 (en) * 1997-04-18 2002-06-13 Klaus Stenzel Fungicide active substance combinations
CN1330238C (zh) * 1997-04-25 2007-08-08 石原产业株式会社 防治有害生物的组合物和用该组合物防治有害生物的方法
UA70327C2 (uk) * 1998-06-08 2004-10-15 Баєр Акціенгезельшафт Спосіб боротьби з фітопатогенними хворобами сільськогосподарських рослин та фунгіцидна композиція

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02054870A2 *

Also Published As

Publication number Publication date
US20040029944A1 (en) 2004-02-12
JP2004525880A (ja) 2004-08-26
WO2002054870A2 (fr) 2002-07-18
BR0206451A (pt) 2003-12-30
WO2002054870A3 (fr) 2002-12-12

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RIN1 Information on inventor provided before grant (corrected)

Inventor name: HADEN, EGON

Inventor name: SCHELBERGER, KLAUS

Inventor name: SCHERER, MARIA

Inventor name: STRATHMANN, SIEGFRIED

Inventor name: LORENZ, GISELA

Inventor name: STIERL, REINHARD

Inventor name: AMMERMANN, EBERHARD

Inventor name: PTOCK, ARNE

Inventor name: GROTE, THOMAS

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