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EP1365654A1 - Melanges fongicides constitues de benzophenones et de derives d'imidazole - Google Patents

Melanges fongicides constitues de benzophenones et de derives d'imidazole

Info

Publication number
EP1365654A1
EP1365654A1 EP02710801A EP02710801A EP1365654A1 EP 1365654 A1 EP1365654 A1 EP 1365654A1 EP 02710801 A EP02710801 A EP 02710801A EP 02710801 A EP02710801 A EP 02710801A EP 1365654 A1 EP1365654 A1 EP 1365654A1
Authority
EP
European Patent Office
Prior art keywords
formula
methyl
compounds
benzophenones
imidazole 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Withdrawn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
EP02710801A
Other languages
German (de)
English (en)
Inventor
Arne Ptock
Ingo Rose
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 EP1365654A1 publication Critical patent/EP1365654A1/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Withdrawn legal-status Critical Current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
    • A01N43/90—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 containing
  • R 1 represents chlorine, methyl, methoxy, acetoxy, pivaloyloxy or hydroxy
  • R 2 represents chlorine or methyl
  • R 3 represents hydrogen, halogen or methyl
  • R 4 represents C ⁇ -C 6 alkyl or benzyl, where the phenyl part of the benzyl radical can carry a halogen or methyl substituent, and
  • the invention also relates to methods for controlling harmful fungi with mixtures of the compounds I and II and agents conditioned in two parts.
  • the compounds of formula I, their preparation and their activity against harmful fungi are known from the literature (EP-A 727 141; EP-A 897 904; EP-A 899 255; ⁇ P-A 967 196).
  • the object of the present invention was to provide further particularly effective mixtures for combating harmful fungi and in particular for certain indications.
  • the present invention was based on the problem of mixtures which, with a reduced total amount of active compounds applied, have an improved activity against harmful fungi (synergistic mixtures).
  • 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, fruit, ornamental plants and vines.
  • mixtures containing compounds I in which R 2 is chlorine or methyl are preferred.
  • compounds I in which R 2 is methyl are preferred.
  • compounds I are preferred in which R 3 represents hydrogen, methyl, chlorine or bromine and particularly preferably hydrogen, chlorine or bromine.
  • R 4 is -C 4 -alkyl or benzyl, where the phenyl part of the benzyl radical can carry a halogen or methyl substituent.
  • R 4 is C 1 -C 4 -alkyl and preferably methyl.
  • R 1 , R 2 , R 3 and R 4 have the following meaning: R 1 methoxy, acetoxy or hydroxy; R 2 methyl; R 3 is hydrogen, chlorine or bromine; and R 4 -CC 4 alkyl.
  • Fungicidal mixtures which are preferred as component a) e ne of the compounds: 1-33, 1-35, 1-42, 1-44, 1-46, 1-60, or preferably 1-18, 1-28, 1- 37, and contain as component b) one of the compounds II.
  • the compounds II are able to form 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.
  • 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 branched or straight-chain chains) 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 residues), where the alkyl or aryl residues can carry further substituent
  • the ions of the elements of the first to eighth subgroups especially chromium, manganese, iron, cobalt, nickel, copper, zinc and, in addition, 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 valences which they can assume.
  • the quantitative ratio of the compounds I and II can be varied within wide ranges; the active compounds are preferably used in a weight ratio in the range from 1000: 1 to 1: 1, preferably 400: 1 to 10: 1 and particularly preferably 200: 1 to 50: 1.
  • the pure active ingredients I and II When preparing the mixtures, use is preferably made of the pure active ingredients I and II, to which further active ingredients can be admixed against harmful fungi or against other pests such as insects, arachnids or nematodes or else herbicidal or growth-regulating active ingredients or fertilizers.
  • 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 Deutero- mycetes from. Some of them are 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 application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 10 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.2 to 3.0 kg / ha, depending on the type of effect desired ,
  • the application rates for the compounds I are 0.005 to 6.5 kg / ha, preferably 0.08 to 3.0 kg / ha, in particular 0.12 to 2.0 kg / ha.
  • the application rates for the compounds II are accordingly 0.005 to 3.5 kg / ha, preferably 0.02 to 2 kg / ha, in particular 0.08 to 1.0 kg / ha.
  • 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 be prepared, 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, spreading 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 known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where 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), amines (e.g. ethanolamine , Dimethylformamide) and water;
  • 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 sulfite waste liquors and methyl cellulose.
  • the surface-active substances are the alkali metal, alkaline earth metal, ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polygly
  • 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, 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 soils 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 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. example
  • 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.
  • ⁇ 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.
  • Example of use 1 Protective activity against late blight on tomatoes caused by Phytophthora infestans
  • Leaves of potted plants of the "Large meat tomato St. Pierre" were treated with an aqueous suspension consisting of a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5 % Of emulsifier was sprayed on until dripping wet. The following day the leaves were infected with a cold aqueous zoospore suspension of Phytoph thora infes tans with a density of 0.25 x 10 6 spores / ml. The plants were then placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° C. After 6 days, the herb rot had developed so strongly on the untreated but infected control plants 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Mélanges fongicides qui contiennent (a) des benzophénones de formule (I), dans laquelle R<1> représente chlore, méthyle, méthoxy, acétoxy, pivaloyloxy ou hydroxy; R<2> représente chlore ou méthyle; R<3> représente hydrogène, halogène ou méthyle; et R<4> représente alkyle C1-C6 ou benzyle, la partie phényle du reste benzyle pouvant porter un halogène ou des substituants méthyle, et (b) des dérivés d'imidazole de formule (II), dans laquelle Y représente brome ou chlore, en quantité synergiquement active, procédé de lutte contre des champignons parasites à l'aide de mélanges des composés I et II et produits les contenant.
EP02710801A 2001-01-18 2002-01-17 Melanges fongicides constitues de benzophenones et de derives d'imidazole Withdrawn EP1365654A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10102282 2001-01-18
DE10102282 2001-01-18
PCT/EP2002/000413 WO2002056689A1 (fr) 2001-01-18 2002-01-17 Melanges fongicides constitues de benzophenones et de derives d'imidazole

Publications (1)

Publication Number Publication Date
EP1365654A1 true EP1365654A1 (fr) 2003-12-03

Family

ID=7671063

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02710801A Withdrawn EP1365654A1 (fr) 2001-01-18 2002-01-17 Melanges fongicides constitues de benzophenones et de derives d'imidazole

Country Status (5)

Country Link
US (1) US20040053984A1 (fr)
EP (1) EP1365654A1 (fr)
JP (1) JP4188688B2 (fr)
AR (1) AR032507A1 (fr)
WO (1) WO2002056689A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102348380B (zh) 2009-03-16 2013-10-23 巴斯夫欧洲公司 包含氟吡菌酰胺和苯菌酮的杀真菌组合物
US11686208B2 (en) 2020-02-06 2023-06-27 Rolls-Royce Corporation Abrasive coating for high-temperature mechanical systems

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5773663A (en) * 1996-05-01 1998-06-30 American Cyanamid Company Fungicidal methods, compounds and compositions containing benzophenones
CZ294096B6 (cs) * 1995-01-20 2004-10-13 Americanácyanamidácompany Benzofenonové sloučeninyŹ způsob jejich výrobyŹ fungicidní prostředky s jejich obsahem a způsob ochrany rostlin
NZ315634A (en) * 1995-08-10 1998-11-25 Bayer Ag Halobenzimidazoles and their use as microbicides
US20020072535A1 (en) * 1997-04-18 2002-06-13 Klaus Stenzel Fungicide active substance combinations
US6297236B1 (en) * 1998-04-06 2001-10-02 Bayer Aktiengesellschaft Fungicide active substance combinations
DE19716256A1 (de) * 1997-04-18 1998-10-22 Bayer Ag Fungizide Wirkstoffkombinationen
US5945567A (en) * 1997-08-20 1999-08-31 American Cyanamid Company Fungicidal 2-methoxybenzophenones
ES2172864T3 (es) * 1997-08-20 2002-10-01 Basf Ag 2-metoxibenzofenonas fungicidas.
DE69812805T2 (de) * 1997-08-20 2003-11-13 Basf Ag Fungizide 2,6,6'-Trimethylbenzophenone
US6242498B1 (en) * 1997-08-20 2001-06-05 Juergen Curtze Fungicidal 2,6,6′-trimethylbenzophenones
DE69912193T2 (de) * 1998-06-24 2004-07-29 Basf Ag Substituierte 2-Hydroxybenzophenone, ihre Herstellung, ihre Verwendung als fungizide und ihre fungizide Zusammensetzungen
US6346535B1 (en) * 1999-01-29 2002-02-12 American Cyanamid Company Fungicidal mixtures
US6127570A (en) * 1999-06-10 2000-10-03 American Cyanamid Company Fungicidal substituted 2-hydroxybenzophenones

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02056689A1 *

Also Published As

Publication number Publication date
WO2002056689A1 (fr) 2002-07-25
US20040053984A1 (en) 2004-03-18
JP4188688B2 (ja) 2008-11-26
AR032507A1 (es) 2003-11-12
JP2004523516A (ja) 2004-08-05

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