EP0923291A1 - Agents pour lutter contre les champignons nuisibles - Google Patents

Agents pour lutter contre les champignons nuisibles

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Publication number
EP0923291A1
EP0923291A1 EP97944801A EP97944801A EP0923291A1 EP 0923291 A1 EP0923291 A1 EP 0923291A1 EP 97944801 A EP97944801 A EP 97944801A EP 97944801 A EP97944801 A EP 97944801A EP 0923291 A1 EP0923291 A1 EP 0923291A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
methyl
compound
stands
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.)
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Application number
EP97944801A
Other languages
German (de)
English (en)
Inventor
Ruth Müller
Herbert Bayer
Hubert Sauter
Karl Eicken
Frank Wetterich
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Maria Scherer
Klaus Schelberger
Bernd Müller
Joachim Leyendecker
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Priority claimed from DE19634771A external-priority patent/DE19634771A1/de
Application filed by BASF SE filed Critical BASF SE
Publication of EP0923291A1 publication Critical patent/EP0923291A1/fr
Withdrawn legal-status Critical Current

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the present invention relates to agents for combating harmful fungi and in particular to fungicidal mixtures of certain carbamates or oxime ethers and valinamides.
  • the invention also relates to a method for controlling harmful fungi using these agents.
  • R 11 , R 12 , R 13 , R 14 , R 15 , m and n have different meanings and X represents an oxygen or ammonium group
  • X represents an oxygen or ammonium group
  • the preparation and use of which for controlling harmful fungi or animal pests is known from WO-A- 96/01256 known.
  • Corresponding t ⁇ azole derivatives are described in OA-96/01258.
  • X represents 0 or NH
  • Y represents CH, CHO or NO
  • Z represents 0, S, NH or, for example, N-alkyl
  • R a , R b and R c can have a number of different meanings.
  • DE-A-195 31 814 describes valinamide derivatives of the formula IIIc
  • R x and RV have different meanings and the two optically active centers are in (S) and (R) configuration.
  • R x and R ⁇ have different meanings, together with at least one further active ingredient, selected from dichlofluanide, tolylfluanid, chlorothalonil, propineb, thiram, mancozeb, dyrene, copper oxychloride, captan, dimetomorph, dithianon, phtan, cymoxanil, propamocarb , Fosetyl, Metalaxyl, Oxadixyl, Fluzzinam, Methoxyacrylaten, Methoximinoacetaten, Furalaxyl, Azolen, such as Triadimenol, Bitertanol, Triadimefon and Tebuconazol, Etidiazol and Pencycuron, contain.
  • at least one further active ingredient selected from dichlofluanide, tolylfluanid, chlorothalonil, propineb, thiram, mancozeb, dyrene, copper oxychloride, captan
  • the present invention was based on the object of providing novel active compound combinations for better combating harmful fungi.
  • mixtures should be made available which are distinguished by a synergistic effect, so that a reduction in the application rates for the active ingredients used is made possible.
  • X represents CH or N
  • radicals R a and R b independently of one another represent a hydrogen atom, a halogen atom, a C ⁇ -C 4 alkyl or -CC 4 ⁇ haloalkyl group;
  • R ' is C ⁇ -C 6 -alkyl, C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -CG-haloalkynyl,
  • C -Cg-cycloalkyl-methyl or benzyl which can be partially or completely halogenated and / or can carry one to three radicals, which are selected from cyano, C ⁇ -C 4 ⁇ alkyl, -C-C 4 haloalkyl, C ! -C 4 alkoxy, -C-C 4 -haloalkoxy and -C-C 4 alkylthio; and
  • X ' represents O or NH
  • Y is CH or N
  • R 1 represents C 3 -C 4 alkyl
  • R 2 is naphthyl or phenyl, the phenyl radical in the 4-position by a halogen atom, a C 1 -C 4 alkyl or
  • compositions according to the invention contain, as compounds of the formula I, in particular carbamates of the formula wherein
  • X ', Y, Z and R' have the meanings given above.
  • a combined application in the sense of the present invention comprises the simultaneous or sequential application of the compounds according to the invention in any order.
  • the connections can be made jointly or separately.
  • the above-mentioned object is also achieved by providing a method for combating harmful fungi, which is characterized in that the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free of them with an effective amount of an agent treated according to the above definition.
  • halogen represents fluorine, chlorine, bromine, iodine, preferably fluorine, chlorine or bromine.
  • C 1 -C 4 -alkyl radicals are saturated, straight-chain or branched hydrocarbon radicals having 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl.
  • C 1 -C 4 -haloalkyl radicals are saturated, straight-chain or branched hydrocarbon chains with 1 to 4 carbon atoms as defined above, where in these groups the hydrogen atoms can be partially or completely replaced by halogen atoms, such as e.g.
  • C ⁇ -Cg-alkyl radicals are saturated, straight-chain or branched hydrocarbon radicals having 1 to 6 carbon atoms, such as the above-mentioned examples of C 1 -C 4 -alkyl, and pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpenty1, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl and
  • C 1 -C 2 -alkyl radicals are straight-chain or branched, saturated carbon chains with 1 to 20 carbon atoms.
  • Ci-C ß -alkyl radicals as defined above and longer-chain alkyl radicals such as unbranched heptyl, octyl, nonyl, decyl, undecyl, lauryl, tridecyl, myristyl, pentadecyl, palmityl, heptadecyl, stearyl, nonadecyl and arachinyl , as well as the one or more branched analogues thereof.
  • Ci-Cg-haloalkyl radicals are saturated, straight-chain or branched hydrocarbon chains with 1 to 6 carbon atoms as defined above, it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms, such as, for example, the above-mentioned examples for C 1 ⁇ C 4- haloalkyl, and 1-fluoro- or 1-chloropentyl and 1-fluoro- or 1-chlorohexyl.
  • C 2 -Cg alkenyl radicals are unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position, such as, for example, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-wench hy1-2-propenyl,
  • C 2 -CG-haloalkenyl are straight-chain or branched carbon radicals having 2 to 6 carbon atoms and a double bond in any position, as defined above, wherein the hydrogen atoms are replaced partially or completely by halogen atoms such as 1-fluoro- or 1-chloroethenyl; 1-fluoro or 1-chloro-1-propenyl, 1-fluoro or 1-chloro-2-propenyl; 3-fluoro or 3-chloro-2-propenyl, or 2, 3, 3-trichloro-2-propenyl.
  • halogen atoms such as 1-fluoro- or 1-chloroethenyl; 1-fluoro or 1-chloro-1-propenyl, 1-fluoro or 1-chloro-2-propenyl; 3-fluoro or 3-chloro-2-propenyl, or 2, 3, 3-trichloro-2-propenyl.
  • C 3 -C 6 alkynyl radicals are straight-chain or branched hydrocarbon groups with 3 to 6 carbon atoms and a triple bond in any position, such as 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l -Methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3rd -Methyl-1-butynyl, 1, 1-Dirnethy1-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl -2-pent
  • C 3 -C 6 -haloalkynyl radicals are straight-chain or branched hydrocarbon groups with 3 to 6 carbon atoms and a triple bond in any position according to the above definition, the hydrogen atoms being partially or completely replaced by halogen atoms, such as 3-fluorine or 3- Chloro-l-propynyl, 1-fluoro or 1-chloro-2-propynyl.
  • C 3 -C 6 cycloalkyl groups include monocyclic alkyl groups having 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • C ⁇ -C 4 alkoxy groups are straight-chain or branched alkyl radicals having 1 to 4 carbon atoms as defined above, which are bonded to the molecule via an oxygen atom, such as methoxy, ethoxy, 1- or 2-propoxy and 1-butoxy.
  • C ⁇ -C 4 -haloalkoxy groups are straight-chain or branched alkoxy groups as defined above with 1 to 4 carbon atoms, in which the hydrogen atoms can be partially or completely replaced by halogen atoms, such as chloromethoxy, fluoromethoxy, 2-fluoro- or 2-chloroethoxy, 3 -Fluoro- or 3-chloropropoxy or 4-fluoro- or 4-chlorobutoxy.
  • halogen atoms such as chloromethoxy, fluoromethoxy, 2-fluoro- or 2-chloroethoxy, 3 -Fluoro- or 3-chloropropoxy or 4-fluoro- or 4-chlorobutoxy.
  • C 1 -C 4 -alkylthio radicals are straight-chain or branched alkyl radicals having 1 to 4 carbon atoms as defined above, which are bonded to the molecule via a sulfur atom, such as, for example, methylthio, ethylthio, 1- or 2-propylthio and 1-butylthio.
  • Preferred fungicidal agents contain oxime ethers of the formula IA or IB
  • R ' represents Ci-Cg-alkyl, -C-C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -Cg cycloalkylmethyl, benzyl or ring-halogenated benzyl.
  • Particularly preferred compounds of the formulas IA and IB are those whose Z-R 'radicals have the meanings given in Table I below.
  • IA.3, IB.3 0-CH 2 CH 2 CH 2 CH3
  • Examples of particularly preferred compounds are IA.2 and IA.4.
  • either the pure E or Z isomers or E / Z isomer mixtures can be present.
  • the E / Z isomer mixture or the E isomer is preferably used in each case, the E isomer of the oxime ethers being particularly preferred.
  • oxime ethers with the following E / Z configuration in the side chain are preferred:
  • oxime ethers of the formula I contained in the agents according to the invention and their preparation are per se from the older one
  • Oxime ethers of the formula I can then be prepared, for example, by reacting a benzyl derivative of the formula IV
  • L 1 represents a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate and triflate,
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine) in accordance with the methods described in Houben-Weyl, 4th edition, vol. E 14b, p. 370f and Houben -Weyl, vol. 10/1, p. 1189f.
  • a base for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine
  • the required hydroxyimine V is obtained, for example, by reacting an appropriate dihydroxyimine VI
  • nucleophilically substituted reagent H 3 CL 2 wherein L 2 stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate and triflate.
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base (for example potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine) in accordance with the methods described in Houben-Weyl, vol. E 14b, p. 307f, p. 370f and p . 385f; Houben-Weyl, 4th edition, vol. 10/4, pp. 55f, p. 180f and p. 217f; Houben-Weyl, vol. E 5, p. 780f.
  • a base for example potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine
  • the compounds of formula VI are known (DE-A-26 21 102) or can be prepared by known methods.
  • X has the meanings given above and at least one of the radicals R a and R b does not represent a hydrogen atom, and z. B. is selected from halogen and -CC 4 ⁇ alkyl.
  • carbamates used according to the invention are known per se. Their preparation is described, for example, in WO-A-96/01256 and WO-A-96/01258, which are hereby expressly incorporated by reference. Compounds IC.l to IC 52 listed in Table II below can be mentioned as examples of preferred carbamates.
  • the compounds IC.12, IC.23, IC.32 and IC.38, in particular IC.32 and IC.38, are particularly preferred.
  • a first preferred group of valiamide derivatives are compounds of the formula II '
  • R 1 is as defined above and X is halogen, -CC 4 alkyl or -CC 4 alkoxy.
  • valinamide derivatives are compounds of the formula II ′′
  • R 1 has the meanings given above.
  • Compounds of this type and their preparation are described for example in DE-A-43 21 897 and WO-A-96/07638, to which express reference is hereby made.
  • R 2 is ⁇ -naphthyl, ⁇ -naphthyl and phenyl, the phenyl radical in the 4-position being substituted by chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 alkoxy.
  • Valina ide which can be used according to the invention are summarized in Table III below.
  • compounds of the formula II are used in which the amino acid part is formed from alkoxycarbonyl-L-valine (S configuration) and the phenethylamine part or the naphthylethylamine part has the R configuration.
  • Such compounds can be represented by the general formula Ha
  • R 1 and R 2 have the meanings given for the compounds of the formula II.
  • the isomerically pure compounds of the formula Ha can be prepared in a manner known per se, starting from the corresponding L-valine-based carbamoylcarboxylic acids VII.
  • the compounds Ha are obtained by the processes described below, using a carbamoylcarboxylic acid VII with an amine VIII (the literature references "Houben-Weyl” refer to: Houben-Weyl, Methods of Organic Chemistry, 4th edition, Thieme Verlag, Stuttgart):
  • the carbamoylcarboxylic acids VII are known or can be prepared by known methods, especially starting from the amino acid L-valine (cf. "Houben-Weyl", volume 15/1, pp. 46-305, especially pp. 117-125) . 5
  • Amines VIII are also known or can easily be obtained (cf. Organikum, VEB German Publishing House of Sciences, 15th edition, Berlin, 1977, pp. 610 ff .; "Houben-Weyl", volume 15/1, p. 648 -665; Indian J. Chem. 10, p. 366 (1972); J. Am. Chem. Soc. 10 58, p. 1808-1811 (1936)).
  • the R-isomer can be separated from racemates of amines VIII in a manner known per se, for example by fractional crystallization with optically active tartaric acid or preferably by means of enzyme-catalyzed esterification and subsequent saponification (cf. for example WO-A-95/08636). .
  • This process is preferably carried out by first converting the carbamoylcarboxylic acids VII into carboxy-activated derivatives, especially acyl cyanides or anhydrides (cf. Tetrahedron Letters, Volume 18, pp. 1595-1598 (1973), or " Houben-Weyl ", volume 15/1, pp. 28-32). These derivatives are then reacted with the A in VI in the presence of bases.
  • carboxy-activated acyl cyanides e.g. the reaction of carbamoylcarboxylic acids VII with diethyl cyanophosphate, especially in an inert solvent such as tetrahydrofuran or toluene.
  • carboxy-activated anhydrides the reaction of carbamoylcarboxylic acid VII with carbonic acid chlorides, such as isobutyl chloroformate, in the presence of bases and, if appropriate, in an inert solvent, such as toluene or tetrahydrofuran, is preferred.
  • carbonic acid chlorides such as isobutyl chloroformate
  • reaction of the amines VIII with the carboxy-activated carbamoylcarboxylic acids VII is preferably carried out in a solvent such as dichloromethane, tetrahydrofuran or toluene.
  • the amines VIII can also serve as bases, usually being recovered from the crude product.
  • the carbamoylcarboxylic acid VII, the A in VIII, the reagent suitable for producing the carboxy-activated derivative of carbamoylcarboxylic acid VII and the base are reacted in a one-pot process, if appropriate in an inert solvent and the crude product is then worked up in a manner known per se for the isolation of the carboxylcarboxamide Ha.
  • the compounds of the formula I and II are capable of forming salts or adducts with inorganic or organic acids or with metal ions, which can likewise be used according to the invention.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, 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 or sulfonic acid acids (sulfonic acid acids) branched alkyl radicals with 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 residues), where
  • 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, and also the first to eighth subgroup, in particular chromium, manganese, iron, cobalt, nickel, copper, come as metal ions. Zinc and others into 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 and II or the simultaneous, joint or separate, use of the compounds I and II are distinguished by an excellent activity against broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can therefore also be used as leaf and soil fungicides.
  • the compounds I and II are usually used in a weight ratio of 10: 1 to 0.1: 1, preferably 5: 1 to 0.2: 1, in particular 5: 1 to 1: 1.
  • At least one compound of formula IA or IB with at least one compound of formula II such as. B.
  • At least one compound of formula IC with at least one compound of formula II such as. B.
  • the application rates of the mixtures according to the invention are from 0.01 to 3 kg / ha, preferably 0.1 to 1.5 kg / ha, in particular 0.1 to 1.0 kg / ha.
  • the application rates for the compounds I are 0.01 to 0.5 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.4 kg / ha.
  • the application rates for the compounds II are accordingly from 0.01 to 0.5 kg / ha, preferably 0.05 to 0.5 kg / ha, in particular 0.05 to 0.4 kg / ha.
  • application rates of the mixture of from 0.001 to 50 g / kg of seed preferably 0.01 to 10 g / kg, in particular 0.01 to 8 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 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 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.
  • the surface-active substances are the alkali metal, alkaline earth metal and 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 5-octylphenol ether, ethoxylated isooctyl, octyl or nonyl phenyl, alkyl phenol or tribol glycol,
  • 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. coated, impregnated or homogeneous granules
  • a solid carrier e.g., a wax
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolo-
  • 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 grain 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 grain 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
  • the compounds I or II or the mixtures or the corresponding formulations are used by the fungi, the plants, seeds, soils, 40 areas, materials or spaces to be kept free of them with a fungicidally active
  • the application can take place before or after the infestation by the harmful fungi.
  • the active ingredients were separated or together as a 10% emulsion in a mixture of cyclohexanone and emulsifier (such as Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and Emulphor® EL (Emulan ® EL, emulsifier based on ethoxylated fatty alcohols)) and diluted with water to the desired concentration.
  • cyclohexanone and emulsifier such as Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and Emulphor® EL (Emulan ® EL, emulsifier based on ethoxylated fatty alcohols)
  • ⁇ corresponds to the fungal attack of the treated plants in%
  • ß corresponds to the fungal infection of the untreated (control) plants in%
  • Example 1 Activity against Phytophthora infestans on tomatoes
  • Leaves of potted plants of the variety Large meat tomatoes 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 steam-saturated chamber at temperatures between 16 and 18 ° C. After six days, the blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • Leaves of pot vines of the Müller Thurgau variety 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 plants were placed in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
  • the vines were then left in a chamber saturated with water vapor for 48 hours and then in a greenhouse at temperatures between 20 and 5 days and set up at 30 ° C. After this time, the plants were again placed in a moist chamber for 16 h in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually.

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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)

Abstract

L'invention concerne des agents pour lutter contre les champignons nuisibles, contenant dans un support solide ou liquide a) au moins un composé de la formule (I) dans laquelle M1 et M2 possèdent des notations différentes, et b) au moins un valinamide de la formule (II) dans laquelle R1 désigne alkyle C¿3?-C4 et R?2¿ représente naphtyle ou phényle, le reste phényle étant substitué en position 4 par un atome d'halogène, un groupe alkyle C¿1?-C4 ou alcoxy C1-C4. L'invention concerne également un procédé pour lutter contre les champignons nuisibles à l'aide de ces agents.
EP97944801A 1996-08-28 1997-08-27 Agents pour lutter contre les champignons nuisibles Withdrawn EP0923291A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19634771A DE19634771A1 (de) 1996-08-28 1996-08-28 Mittel zur Bekämpfung von Schadpilzen
DE19634771 1996-08-28
DE19636752 1996-09-10
DE19636752 1996-09-10
PCT/EP1997/004679 WO1998008386A1 (fr) 1996-08-28 1997-08-27 Agents pour lutter contre les champignons nuisibles

Publications (1)

Publication Number Publication Date
EP0923291A1 true EP0923291A1 (fr) 1999-06-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP97944801A Withdrawn EP0923291A1 (fr) 1996-08-28 1997-08-27 Agents pour lutter contre les champignons nuisibles

Country Status (15)

Country Link
US (1) US6156778A (fr)
EP (1) EP0923291A1 (fr)
JP (1) JP2000516944A (fr)
KR (1) KR20000035947A (fr)
CN (1) CN1228676A (fr)
AR (1) AR009461A1 (fr)
AU (1) AU716351B2 (fr)
BR (1) BR9711266A (fr)
CA (1) CA2264533A1 (fr)
CO (1) CO4870748A1 (fr)
IL (1) IL128440A0 (fr)
NZ (1) NZ334367A (fr)
PL (1) PL331889A1 (fr)
TW (1) TW438575B (fr)
WO (1) WO1998008386A1 (fr)

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Publication number Priority date Publication date Assignee Title
DE4304172A1 (de) * 1993-02-12 1994-08-25 Bayer Ag Fungizide Wirkstoffkombinationen
ATE250341T1 (de) * 1998-05-04 2003-10-15 Basf Ag Fungizide mischungen
UA70327C2 (uk) * 1998-06-08 2004-10-15 Баєр Акціенгезельшафт Спосіб боротьби з фітопатогенними хворобами сільськогосподарських рослин та фунгіцидна композиція
ATE385693T1 (de) * 2004-04-21 2008-03-15 Basf Ag Fungizide mischungen
CN104945293B (zh) * 2015-06-18 2017-04-12 南开大学 一种含硫氨基酸酰胺氨基甲酸酯衍生物及应用

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DE2621102A1 (de) * 1976-05-10 1977-11-24 Schering Ag Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
DE3915755A1 (de) * 1989-05-13 1990-11-29 Bayer Ag Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung
DE4304172A1 (de) * 1993-02-12 1994-08-25 Bayer Ag Fungizide Wirkstoffkombinationen
DE4321897A1 (de) * 1993-07-01 1995-01-12 Hoechst Schering Agrevo Gmbh Substituierte Aminosäureamid-Derivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und ihre Verwendung
FI101413B (fi) * 1993-07-05 1998-06-15 Ari Veli Olavi Loeytty Jätelämmön hyödyntämismenetelmä esim. voimalaitoksissa
DE4332738A1 (de) * 1993-09-25 1995-03-30 Basf Ag Racematspaltung primärer und sekundärer Amine durch Enzym-katalysierte Acylierung
JP3307396B2 (ja) * 1994-02-04 2002-07-24 ビーエーエスエフ アクチェンゲゼルシャフト フェニル酢酸誘導体、これを製造するための方法および中間生成物、並びにこれを含有する薬剤
DE4423612A1 (de) * 1994-07-06 1996-01-11 Basf Ag 2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung
DE4423613A1 (de) * 1994-07-06 1996-01-11 Basf Ag 2-[1',2',4'-Triazol-3'yloxymethylen]-anilide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4431467A1 (de) * 1994-09-03 1996-03-07 Basf Ag Caramoylcarbonsäureamide
DE19531814A1 (de) * 1995-08-30 1997-03-06 Basf Ag Carbamoylcarbonsäureamide
DE19528651A1 (de) * 1995-08-04 1997-02-06 Basf Ag Hydroximsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel
TW328945B (en) * 1995-08-30 1998-04-01 Basf Ag Carbamoylcarboxamides

Non-Patent Citations (1)

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Title
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Also Published As

Publication number Publication date
KR20000035947A (ko) 2000-06-26
WO1998008386A1 (fr) 1998-03-05
CA2264533A1 (fr) 1998-03-05
US6156778A (en) 2000-12-05
PL331889A1 (en) 1999-08-16
JP2000516944A (ja) 2000-12-19
BR9711266A (pt) 1999-08-17
AU716351B2 (en) 2000-02-24
CO4870748A1 (es) 1999-12-27
IL128440A0 (en) 2000-01-31
AU4618897A (en) 1998-03-19
TW438575B (en) 2001-06-07
NZ334367A (en) 2000-11-24
AR009461A1 (es) 2000-04-26
CN1228676A (zh) 1999-09-15

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