EP0900014A1 - Melanges fungicides - Google Patents

Melanges fungicides

Info

Publication number
EP0900014A1
EP0900014A1 EP97921704A EP97921704A EP0900014A1 EP 0900014 A1 EP0900014 A1 EP 0900014A1 EP 97921704 A EP97921704 A EP 97921704A EP 97921704 A EP97921704 A EP 97921704A EP 0900014 A1 EP0900014 A1 EP 0900014A1
Authority
EP
European Patent Office
Prior art keywords
dithiocarbamate
compound
alkyl
iii
zinc
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Withdrawn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
EP97921704A
Other languages
German (de)
English (en)
Inventor
Ruth Müller
Herbert Bayer
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Klaus Schelberger
Maria Scherer
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 EP0900014A1 publication Critical patent/EP0900014A1/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Withdrawn legal-status Critical Current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
    • 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 a fungicidal mixture, which
  • X is oxygen or amino (NH);
  • Y is CH or N
  • Z is oxygen, sulfur, amino (NH) or C 1 -C 4 alkylamino (N -C 1 -C 4 alkyl);
  • the invention relates to methods for controlling harmful fungi with mixtures of the compounds I, II and / or III and the use of the compounds I, II and III for the production of such mixtures.
  • dithiocarbamates II (Ila: common name: Mancozeb, US-A 3,379,610; llb: common name: Maneb, US-A 2,504,404; IIc: former common name: Metiram, US-A 3,248,400; Ild: common name: Zineb, US-A 2,457,674), their preparation and their action against harmful fungi.
  • 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).
  • the present invention relates to mixtures of compounds I and II or I and III and mixtures which contain a compound I, a compound II and a compound III.
  • the general formula I is particularly representative of oxime ethers in which X is oxygen and Y is CH or X is amino and Y is N,
  • the E / Z isomer mixture or the E isomer is preferably used, the E isomer being particularly preferred.
  • the compounds I can be used both as isomer mixtures and as pure isomers in the mixtures according to the invention.
  • compounds I are particularly preferred in which the terminal oxime ether grouping of the side chain is in the cis configuration (OCH 3 group to ZR ').
  • the compounds I and III 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 iodine-hydrogen, 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 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 acids or sulfonic acids with straight-chain acids) 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 with 1 to 20 carbon atoms), Arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two phosphoric acid radicals), where the alkyl
  • the ions of the elements of the second main group in particular calcium and magnesium
  • the third and fourth main group in particular aluminum, tin and lead
  • the first to eighth subgroups come in particular as metal ions Consideration.
  • the metal ions of the elements of the subgroups of the fourth period are particularly preferred.
  • the metals can be present in the various valences that they have.
  • the mixtures of the compounds I, II and III or the simultaneous joint or separate use of the compounds I, II and III are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. They are partly systemically effective and can therefore also be used as leaf and soil fungicides.
  • the compounds I, II and / or III can be applied at the same time together 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 200: 1 to 0.1: 1, preferably 100: 1 to 1: 1, in particular 50: 1 to 5: 1 (II: I).
  • the compounds I and III are usually used in a weight ratio of 10: 1 to 0.1: 1, preferably 5: 1 to 0.2: 1, in particular 3: 1 to 1: 3 (III: I).
  • the application rates of the mixtures according to the invention are in general from 0.005 to 0.5 kg / ha, preferably 0.01 to 0.5 kg / ha, in particular 0.01 to 0.3 kg / Ha.
  • the application rates for the compounds II are generally 0.1 to 10 kg / ha, preferably 0.5 to 5 kg / ha, in particular 1 to 4 kg / ha.
  • the application rates for the compounds III are generally 0.005 to 0.8 kg / ha, preferably 0.01 to 0.5 kg / ha, in particular 0.05 to 0.3 kg / ha.
  • application rates of the mixture of 0.001 to 100 g / kg of seed preferably 0.01 to 50 g / kg, in particular 0.01 to 10 g / kg, are generally used.
  • the compounds I and II or III or the mixtures of the compounds I, II and III are applied separately or together 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 compounds I, II and 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, Spreading agents 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 be as fine and ensure uniform distribution of the mixture according to the invention.
  • 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 spreading and dusts can be prepared by mixing or grinding the compounds I, II and / or III together or the mixture of the compounds I, II and III 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, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics serve as fillers or solid carriers, for example. 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.
  • 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 the compounds I and II or III or the mixture of the compounds I, II and III.
  • the active ingredients are in a purity of 90% to 100%, ⁇ preferably 95% to 100% (according to the NMR or HPLC spectrum).
  • the compounds I, II and / or III or the mixtures or the corresponding formulations are used by adding a fungicidally effective amount of the harmful fungi, the plants, seeds, soil, surfaces, materials or spaces to be kept free of them Mixture, or the compounds I, II and / or III treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • the fungicidal activity of the compound and the mixtures can be demonstrated by the following tests:
  • the active ingredients are separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and
  • Emulphor® EL Emulphor® EL, emulsifier based on ethoxylated fatty alcohols
  • the evaluation is carried out by determining the affected leaf areas in percent. These percentages were converted into efficiencies.
  • the expected efficacies of the active ingredient mixtures are calculated according to the Colby formula [R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficiencies.
  • E expected efficiency expressed in% of the untreated control, when using the mixture of active ingredients A, B and C in concentrations a, b and c
  • ⁇ corresponds to the fungal attack of the treated plants in%
  • the infection of the treated plants corresponds to that of the untreated control plants; with an efficiency of 100, the treated plants are not infected.
  • Leaves of potted plants of the "large meat tomato" type were sprayed to runoff point with an aqueous suspension which was prepared from a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier. The following day, the leaves were infected with an aqueous suspension of zoospores from phytophthora infestans. The plants were then placed in a water vapor-saturated chamber at temperatures between 16 and 18 ° 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%.
  • Leaves of potted vines of the "Müller-Thurgau" variety were inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
  • the vines were then placed in a steam-saturated chamber at 22-24 ° C for 48 hours. They were then removed from the chambers and, after drying, were sprayed to runoff point with aqueous preparation of active compound, which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. After the spray coating had dried on, the plants were further cultivated for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a humid climatic chamber for 16 hours in order to accelerate the outbreak of sporangium carriers. The extent of the development of the infestation on the undersides of the leaves was then determined visually.

Abstract

L'invention concerne des mélanges fungicides contenant dans des quantités garantissant un effet synergique: a) un éther d'oxime de la formule (I) dans laquelle les substituants ont la notation suivante: X désigne oxygène ou amino (NH); Y désigne CH ou N; Z désigne oxygène, soufre, amino (NH) ou alkylamino C1-C4(N-alkyle C1-C4); R' désigne alkyle C1-C6, halogénure d'alkyle C1-C6, alcényle C3-C6, halogénure d'alcényle C2-C6, alcynyle C3-C6, halogénure d'alcynyle C3-C6, cycloalkyle C3-C6-méthyle, ou benzyle, qui peut être halogéné partiellement ou entièrement et/ou peut porter entre un et trois des restes suivants: cyano, alkyle C1-C4, halogénure d'alkyle C1-C4, alcoxy C1-C4, halogénure d'alcoxy C1-C4 et alkylthio C1-C4; et b) un dithiocarbamate (II) sélectionné dans le groupe éthylène bisdithiocarbamate manganeux (complexe zinc) (IIa), éthylène bisdithiocarbamate manganeux (IIb), éthylène bisdithiocarbamate d'ammoniacate de zinc (IIc) et éthylène bisdithiocarbamate d'ammoniacate de zinc (IId), et/ou c) 1-(2-cyano-2-méthoxyiminoacétyl)-3-éthylurée (III) H3CCH2-NHCONH-CO-C(CN)=NOCH3.
EP97921704A 1996-04-26 1997-04-23 Melanges fungicides Withdrawn EP0900014A1 (fr)

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
DE19616685 1996-04-26
DE19616683 1996-04-26
DE19616685 1996-04-26
DE19616683 1996-04-26
DE19617072 1996-04-29
DE19617072 1996-04-29
DE19635514 1996-09-02
DE19635517 1996-09-02
DE19635509 1996-09-02
DE19635509 1996-09-02
DE19635517 1996-09-02
DE19635514 1996-09-02
PCT/EP1997/002046 WO1997040677A1 (fr) 1996-04-26 1997-04-23 Melanges fungicides

Publications (1)

Publication Number Publication Date
EP0900014A1 true EP0900014A1 (fr) 1999-03-10

Family

ID=27545042

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97921704A Withdrawn EP0900014A1 (fr) 1996-04-26 1997-04-23 Melanges fungicides

Country Status (6)

Country Link
US (1) US6114378A (fr)
EP (1) EP0900014A1 (fr)
JP (1) JP2000509060A (fr)
AU (1) AU2768297A (fr)
CO (1) CO4761016A1 (fr)
WO (1) WO1997040677A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011161945A1 (fr) * 2010-06-24 2011-12-29 クミアイ化学工業株式会社 Dérivé alcoxyimino et agent antiparasitaire

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2457674A (en) * 1944-12-02 1948-12-28 Rohm & Haas Fungicidal compositions
US2504404A (en) * 1946-06-12 1950-04-18 Du Pont Manganous ethylene bis-dithiocarbamate and fungicidal compositions containing same
BE617407A (fr) * 1961-05-09
US3957847A (en) * 1974-03-21 1976-05-18 E. I. Du Pont De Nemours And Company 2-cyano-2-hydroxyiminoacetamides as plant disease control agents
TW321586B (fr) * 1993-09-24 1997-12-01 Basf Ag
TW340033B (en) * 1993-09-24 1998-09-11 Basf Ag Fungicidal mixtures
EP0741970B1 (fr) * 1993-12-02 2002-04-24 Sumitomo Chemical Company Limited Composition bactericide
RU2165411C2 (ru) * 1994-02-04 2001-04-20 Басф Акциенгезельшафт Производные фенилуксусной кислоты, промежуточные продукты для их получения и содержащие их средства
CN1046706C (zh) * 1994-02-04 1999-11-24 巴斯福股份公司 苯乙酸衍生物,它们的制备和有关的中间体,以及含有它们的组合物
DE4420277A1 (de) * 1994-06-10 1995-12-14 Basf Ag Fungizide Mischungen
DE4420279A1 (de) * 1994-06-10 1995-12-14 Basf Ag Fungizide Mischungen
UA54395C2 (uk) * 1995-06-16 2003-03-17 Баєр Акціенгезельшафт Фітобактерициднa композиція, спосіб контролю та запобігання хворобам рослин, матеріал для розмноження рослин
DE19528651A1 (de) * 1995-08-04 1997-02-06 Basf Ag Hydroximsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel
ATE185678T1 (de) * 1995-08-17 1999-11-15 Basf Ag Fungizide mischungen eines oximethercarbonsäureamids mit cymoxan il
JP3883575B2 (ja) * 1995-08-17 2007-02-21 ビーエーエスエフ アクチェンゲゼルシャフト 殺菌剤混合物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9740677A1 *

Also Published As

Publication number Publication date
WO1997040677A1 (fr) 1997-11-06
CO4761016A1 (es) 1999-04-27
AU2768297A (en) 1997-11-19
JP2000509060A (ja) 2000-07-18
US6114378A (en) 2000-09-05

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