WO1999048370A1 - Fungicide mixtures based on triple oxime ether derivatives and resistance inductors - Google Patents

Fungicide mixtures based on triple oxime ether derivatives and resistance inductors Download PDF

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Publication number
WO1999048370A1
WO1999048370A1 PCT/EP1999/001917 EP9901917W WO9948370A1 WO 1999048370 A1 WO1999048370 A1 WO 1999048370A1 EP 9901917 W EP9901917 W EP 9901917W WO 9948370 A1 WO9948370 A1 WO 9948370A1
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WIPO (PCT)
Prior art keywords
alkyl
alkylamino
alkylaminothiocarbonyl
hetaryl
aryl
Prior art date
Application number
PCT/EP1999/001917
Other languages
German (de)
French (fr)
Inventor
Klaus Schelberger
Thomas Grote
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Original Assignee
Basf Aktiengesellschaft
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Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to JP2000537436A priority Critical patent/JP4458668B2/en
Priority to CA002323593A priority patent/CA2323593A1/en
Priority to AU33317/99A priority patent/AU3331799A/en
Priority to IL13812599A priority patent/IL138125A0/en
Priority to EP99914531A priority patent/EP1065929A1/en
Priority to BR9909045-7A priority patent/BR9909045A/en
Publication of WO1999048370A1 publication Critical patent/WO1999048370A1/en

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    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/56—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles

Definitions

  • the present invention relates to fungicidal mixtures for combating harmful fungi which
  • R ⁇ R independently of one another was sers tof f and -CC alkyl
  • n 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
  • R 3 is hydrogen, cyano, -CC alkyl, -C ⁇ C 4 haloalkyl, C 3 -C ⁇ cycloalkyl;
  • R 4 , R 6 are independently hydrogen
  • Ci-Cg-haloalkyl Ci-Cg-alkylcarbonyl, C ⁇ -Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg- Alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-C ⁇ -alkylamino, di-Ci-C ß - alkylammo, Ci-Cg-alkylammocarbonyl, di-Ci-Cg-alkylammocarbonyl, Ci-Cg-alkylammothiocarbonyl, D ⁇ - C ⁇ -C 6 - alkylammothiocarbonyl, C -Cg alkenyl, C 2 -C 6 alkenyl - oxy, benzyl, benzyloxy, aryl, aryloxy, he
  • Ci-C ⁇ -Alkla ino di-Ci-Cg-alkylamino, C 2 -C 6 -alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -C 6 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C ⁇ -C 4 -alkoxy, arylthio, aryl -CC 4 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC 4 -alkyl-thio, the cyclic radicals being partially or can be completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl,
  • Ci-Cg-alkylsulfonyl Ci-Cg-alkylsulfoxyl, C 3 C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci Cg-alkylthio, C] _- Cg-alkylamino, di-C] .
  • Ci-Cg-alkylamino-carbonyl di-Ci-Cg-alkylaminocarbonyl
  • Ci-Cg-alkylamino-thiocarbonyl di-Ci-Cg-alkylaminothiocarbonyl
  • C 3 -C ß- cycloalkyl C 3 - C_ -cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino , Carboxyl, Ammo ⁇ carbonyl, aminothiocarbonyl, halogen, Ci-C ß- alkyl, -C-C 6 -haloalkyl, -C-C 6 -alkylsulfonyl, C ⁇ -C 6 -alkyl sulfoxyl, C 3 -C 6 cycloalkyl, Ci -Cg-alkoxy, Ci-Cg-halo-alkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamin
  • A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or C ⁇ -Cg-alkyl; Represents 0 or 1;
  • R ' ' denotes hydrogen or Ci-C ⁇ -alkyl
  • the object of the present invention was to provide fungicidal mixtures which have a good fungicidal action which goes beyond the effectiveness of the mixture components alone, in particular against fungal diseases in rice.
  • EP 313,512 proposed common name: Acibenzolar (trade name: Bion®, Novartis)
  • probenazole (trade name Oryzamate®, Meiji Seika)
  • the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
  • the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example Ci-Cg-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dirnethylethyl , Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl , 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2 -Ethylbutyl
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloroethyl, trichloromethyl, fluoromethyl, difluoromethyl , Trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2 , 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl and pentafluoroethyl;
  • Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -Cg-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl , 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4th -Pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , l-methyl-3-buten
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, e.g. C -Cg-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l- Methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l- Methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pent
  • Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclyllamino three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or ( Heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example 2-tetrahydrofranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazol-dinyl, 4 -isoxazolidinyl, 5 -isoxazolidinyl, 3 -isothiazolidinyl, 4-isothiazolidinyl
  • 1,3-dithian-2-yl 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3, -thiazin-2-yl, 4H-3, l-benzothiazin-2 -yl, 1, l-dioxo-2, 3,4,5-tetrahydrothien-2 -yl, 2H- 1, 4-benzothiazin-3 -yl, 2H- 1, 4 - Benzoxazin-3 -yl, 1,3-dihydro-oxazin-2-yl, 1, 3-dithian-2 -yl,
  • Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) are attached to the skeleton via a sulfonyl group (-SO 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
  • Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, also contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one
  • 5-membered heteroaryl containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms can contain atomic atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl
  • 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or may contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1, 3-diene-1, 4-diyl group;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4 -Pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 10
  • 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta- 1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
  • Hetarylamino aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
  • R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
  • R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, optionally subst.
  • Aryl or hetaryl is.
  • R 5 for optionally subst.
  • Aryl or hetaryl is.
  • R 5 for optionally subst.
  • R 5 for optionally subst. Furyl, thienyl or pyrrolyl.
  • R 5 for optionally subst.
  • R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
  • R 5 is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, ammocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 ⁇ haloalkyl, -C-C 4 alkoxy, -C-C 4 -haloalkoxy, C ⁇ -C 4 -alkylamino, di-C ⁇ -C - alkylamino, C ⁇ -C -alkylsulfonyl, C ⁇ -C-alkoxycarbonyl, C ⁇ -C -alkyl - Aminocarbonyl or Di-C ⁇ -C 4 alkylaminocarbonyl. 12
  • R 4 represents hydrogen, Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -C -alkyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
  • R 4 is C 1 -C 6 -alkyl.
  • the compounds I contained in the mixtures according to the invention are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular against fungi from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.
  • Compound II is commercially available as a so-called resistance inducer (ie active ingredient immunizing against disease infestation), ie II does not have a direct fungicidal action, but instead induces resistance to harmful fungi in the treated plant.
  • Compound III is known as a fungicide. 13
  • the mixtures of the compounds I and at least one compound II to III can be used simultaneously, together or separately and 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 foliar and soil fungicides.
  • the mixtures according to the invention can be used with particular preference for controlling Py ⁇ cula ⁇ a oryzae.
  • the compounds 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 being 14 separate application generally has no effect on the success of the control.
  • 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 0.5 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 0.001 to 5 kg / ha, preferably 0.005 to 2 kg / ha, in particular 0.01 to 1.0 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 separate or joint application of the compounds I and at least one of the compounds II to III is carried out by spraying or dusting the seeds, the plants or the soil before or after the plants are sown or before or after the Emergence of plants.
  • the fungicidal synergistic mixtures according to the invention 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, scattering agents or granules and by spraying, atomizing, dusting , Scattering or pouring can be applied.
  • 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, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol), ketones (eg cyano 15 clohexanone), wet nurse (eg ethanolamm, dirnethylform amide) and water; Carriers such as natural gesture flour (eg kaolins, clays, talc, chalk) and synthetic starch flours (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignite sulfite waste liquors and methyl cellulose.
  • solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignm
  • Powder scattering and dusting agents can be prepared by mixing or grinding the compounds I and at least one of the compounds II to III or the mixture of the compounds I and at least one compound II to III with a solid carrier substance.
  • Granules e.g. coated granules, impregnated granules or homogeneous granules
  • a solid carrier usually produced by binding the active ingredient or ingredients to a solid carrier.
  • Mineral soils such as silica gel, silica, 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 like ammonium sulfate,
  • Ammonium phosphate, ammonium nitrate, ureas and vegetable products such as corn 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 and at least one of the compounds II to III or the mixture of 16 Veromditch 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 corresponding formulations are used in such a way that the harmful fungi, their habitat or the plants, seeds, soil, areas, materials or spaces to be kept free of them are mixed with a fungicidally effective amount of the mixture or of the compounds I and at least one of the compounds II to III for separate application.
  • 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 diisobutylnaphthalm-1-sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite liquor and 7 parts by weight of powdered mixture, ground in a hammer mill Silica rule; A fine boil is obtained by finely distributing the mixture in water; VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient; 17
  • IX a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic 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 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.
  • Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually
  • Example active ingredient conc. in ppm efficiency in% of unh. control

Abstract

The invention relates to fungicide mixtures comprised as active components a) phenylacetic acid derivatives of formula (I) in which the substituents and the index have the meanings cited in the description, and the salts thereof, and b) at least one compound of formulas (II) to (III) in a synergistically effective quantity.

Description

Fungizide Mischungen auf der Basis von Tripeloximether-Derivaten und ResistenzinduktorenFungicidal mixtures based on triple oxime ether derivatives and resistance inducers
Die vorliegende Erfindung betrifft fungizide Mischungen zur Bekämpfung von Schadpilzen, dieThe present invention relates to fungicidal mixtures for combating harmful fungi which
a) Phenylessigsauredeπvate der Formel Ia) Phenylacetic acid derivatives of the formula I.
:D: D
Figure imgf000003_0001
Figure imgf000003_0001
m der die Substituenten und der Index die folgende Bedeutung haben:m where the substituents and the index have the following meaning:
X NOCH3, CHOCH3, CHCH3;X STILL 3 , CHOCH 3 , CHCH 3 ;
Y O, NRY O, NO
R^ R unabhängig voneinander Was sers tof f und Cι-C -Alkyl ;R ^ R independently of one another Was sers tof f and -CC alkyl;
Cyano, Nitro, Tπfluor ethyl , Halogen, Cι.-C. -Alkyl und C ~C -Alkoxy;Cyano, nitro, Tπfluor ethyl, halogen, Cι . -C. -Alkyl and C ~ C -alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Cyano, Cι-C -Alkyl, Cι~C4-Halogenalkyl , C3-Cδ-Cycloalkyl ;R 3 is hydrogen, cyano, -CC alkyl, -C ~ C 4 haloalkyl, C 3 -C δ cycloalkyl;
R4 , R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
Cι-C10-Alkyl, C3-C5-Cycloalkyl , C2-Cι0-Alkenyl ,-CC 10 alkyl, C 3 -C 5 cycloalkyl, C 2 -C 0 -alkenyl,
C2-Cιo-Alkmyl , Cι-Cιo-Alkylcarbonyl , C2-Cιo-Alkenyl - carbonyl , C3-Cιo-Alkιnylcarbonyl oder Cι-Cιn-Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig halogemert sein können oder einen bis drei der folgen- den Gruppen tragen können: Cyano, Nitro, Hydroxy,C 2 -Co-alkmyl, Cι-Cιo-alkylcarbonyl, C 2 -Cιo-alkenyl-carbonyl, C 3 -Cιo-alkιnylcarbonyl or Cι-Cιn-alkylsulfonyl, where these residues can be partially or completely halogenated or one to three of the following groups: cyano, nitro, hydroxy,
Mercapto, Ammo, Carboxyl, Ammocarbonyl , Ammothio- carbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cß-Halogenalkyl , 2Mercapto, ammo, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-C ß -haloalkyl, 2
Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl , Cx-Cg-Alkoxy, Ci-Cδ-Halogenalkoxy, Cι-C6-Alkoxycarbonyl, Ci-Ce-Alkyl- thio, Ci-Cg-Alkylammo, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylammocarbonyl , Di-Ci-Cg-alkylammocarbonyl , Ci-Cg-Alkylaminothiocarbonyl, Dι-Cι-C6-alkylammothιo- carbonyl, C -C6-Alkenyl, C2-C3-Alkenyloxy, C3-C6-Cyclo- alkyl, C3-C6-Cycloalkyloxy, Heterocyclyl , Hetero- cyclyloxy, Benzyl, Benzyloxy, Aryl , Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cycli- sehen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl , Ammothio- carbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl , Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, C3-C6-Cyclo- alkyl, Ci-Cς-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyl- oxycarbonyl, Ci-Cβ-Alkylthio, Ci-Cg-Alkylammo, Di-Ci-Cg-Alkylammo , Ci-Cö-Alkylam ocarbonyl , Di-Ci-Cg-Alkylammocarbonyl , Cι-C6-Alkylammothιo- carbonyl, Di-Ci-Cg-Alkylammothiocarbonyl , C2-C6-C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, Cx-Cg-alkoxy, Ci-C δ -haloalkoxy, Cι-C 6 -alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Cg-alkylammo, di- Ci-Cg-alkylamino, Ci-Cg-alkylammocarbonyl, di-Ci-Cg-alkylammocarbonyl, Ci-Cg-alkylaminothiocarbonyl, Dι-Cι-C 6 -alkylammothιo- carbonyl, C -C 6 -alkenyl, C 2 -C 3 - Alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl, heterocyclicloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, the cyclic groups in turn being partial or can be completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, ammo, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Cι-C 6 -Alkylsulfonyl, Cι-C 6 alkylsulfoxyl, C 3 -C 6 cycloalkyl, Ci-Cς alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cβ-alkylthio, Ci-Cg -Alkylammo, Di-Ci-Cg-Alkylammo, Ci-Cö-Alkylam ocarbonyl, Di-Ci-C g-alkylammocarbonyl, -CC 6 -alkylammothio-carbonyl, di-Ci-Cg-alkylammothiocarbonyl, C 2 -C 6 -
Alkenyl, C -C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C (=NOR7 ) -An-R8 ;Alkenyl, C -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl , Arylsulfonyl , Hetaryl, Hetaryl - carbonyl oder Hetarylsulfonyl , wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl , Halogen, Ci-Cg-Alkyl,Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, ammo, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen , Ci-Cg-alkyl,
Ci-Cg-Halogenalkyl, Ci-Cg-Alkylcarbonyl , Cχ-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , C3-C6-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxy- carbonyl, Ci-Cg-Alkylthio, Ci-Cδ-Alkylamino, Di-Ci-Cß- Alkylammo, Ci-Cg-Alkylammocarbonyl , Di-Ci-Cg-Alkyl- ammocarbonyl , Ci-Cg-Alkylammothiocarbonyl , Dι-Cι-C6- Alkylammothiocarbonyl, C -Cg-Alkenyl , C2-C6-Alkenyl - oxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C (=NOR7) -An-R8 ;Ci-Cg-haloalkyl, Ci-Cg-alkylcarbonyl, Cχ-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg- Alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-C δ -alkylamino, di-Ci-C ß - alkylammo, Ci-Cg-alkylammocarbonyl, di-Ci-Cg-alkylammocarbonyl, Ci-Cg-alkylammothiocarbonyl, Dι- Cι-C 6 - alkylammothiocarbonyl, C -Cg alkenyl, C 2 -C 6 alkenyl - oxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 7 ) -A n -R 8 ;
Wasserstoff ,Hydrogen,
Ci-Cg-Alkyl, C -C6-Alkenyl, C -C6-Alkmyl , wobei die Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, 3Ci-Cg-alkyl, C -C 6 alkenyl, C -C 6 alkyl, where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, ammo , Carboxyl, ammocarbonyl, 3
A inothiocarbonyl, Halogen, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cg-alkylaminothiocarbonyl , C]_-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , Ci-Cs-Alkoxy, Cι~Cg- Halogenalkoxy, Ci-Cg-Alkoxycarbonyl , Ci-Cg-Alkylthio,A inothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C] _- Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl , Ci-Cs-alkoxy, Cι ~ Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio,
Ci-Cδ-Alkyla ino, Di-Ci-Cg-alkylamino, C2-C6-Alkenyloxy, C3-Cg-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl , Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cι-C4-alkoxy, Arylthio, Aryl-Cι-C4-alkylthio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C4-alkoxy, Hetarylthio, Hetaryl-Cι-C4-alkyl - thio, wobei die cyclischen Reste ihrerseits partiell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Aminothiocarbonyl, Ci-Cg-Alkyl,Ci-C δ -Alkla ino, di-Ci-Cg-alkylamino, C 2 -C 6 -alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -C 6 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-Cι -C 4 -alkoxy, arylthio, aryl -CC 4 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC 4 -alkyl-thio, the cyclic radicals being partially or can be completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl,
Cι_-C3-Halogenalkyl, Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkyl- sulfoxyl, C3C6-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl , Ci-Cg-Alkylthio, C]_-Cg- Alkylamino, Di-C].-Cg-alkylamino, Ci-Cg-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkyl- aminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C -C6-Alkenyl , C -Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C (=NOR7) -An-R8; C 1 -C 3 haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci Cg-alkylthio, C] _- Cg-alkylamino, di-C] . -Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylamino-thiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C -C 6 -alkenyl, C -Cg-alkenyloxy, Benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 7 ) -A n -R8 ;
C3 -Cß-Cycloalkyl, C3 - C_ -Cycloalkenyl , Heterocyclyl, Aryl, Hetaryl, wobei die cyclischen Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammo¬ carbonyl, Aminothiocarbonyl, Halogen, Ci-Cß-Alkyl, Cι-C6-Halogenalkyl, Cι-C6-Alkylsulfonyl , Cι-C6-Alkyl- sulfoxyl, C3-C6-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl , Ci-Cg-Alkylthio, Ci-Cg- Alkylamino, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkyl- aminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C2-Cg-Alkenyl , C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;C 3 -C ß- cycloalkyl, C 3 - C_ -cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino , Carboxyl, Ammo ¬ carbonyl, aminothiocarbonyl, halogen, Ci-C ß- alkyl, -C-C 6 -haloalkyl, -C-C 6 -alkylsulfonyl, Cι-C 6 -alkyl sulfoxyl, C 3 -C 6 cycloalkyl, Ci -Cg-alkoxy, Ci-Cg-halo-alkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci -Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, Di-Ci-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
wobeiin which
A für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Cχ-Cg-Alkyl trägt; 0 oder 1 bedeutet;A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Cχ-Cg-alkyl; Represents 0 or 1;
R'' Wasserstof f oder Ci-Cβ-Alkyl bedeutet undR ' ' denotes hydrogen or Ci-Cβ-alkyl and
R8 Was s ers tof f oder Ci-Cg-Alkyl bedeutet ,R 8 What s ers tof f or Ci-Cg-alkyl means
sowi e deren Sal ze ,and their salts,
undand
b) mindestens einem Fungizid ausgewählt aus Fungiziden der Formeln II bis IIIb) at least one fungicide selected from fungicides of the formulas II to III
^^
: ID: ID
Figure imgf000006_0001
Figure imgf000006_0001
:ιn)
Figure imgf000006_0002
: ιn)
Figure imgf000006_0002
OCH2CH=CH2 OCH 2 CH = CH 2
Der vorliegenden Erfindung lag die Aufgabe zugrunde, fungizide Mischungen zur Verfügung zu stellen, die eine gute, über die Wirksamkeit der Mischungskomponenten allein hinausgehende fungi- zide Wirkung, insbesondere gegen Pilzerkrankungen in Reis zeigen.The object of the present invention was to provide fungicidal mixtures which have a good fungicidal action which goes beyond the effectiveness of the mixture components alone, in particular against fungal diseases in rice.
Diese Aufgabe wird erfindungsgemäß durch die Mischungen gemäß Anspruch 1 gelöst.This object is achieved according to the invention by the mixtures according to claim 1.
Die Verbindungen der Formel I sind an sich bekannt und in der Literatur beschrieben (WO 97/15552) .The compounds of formula I are known per se and are described in the literature (WO 97/15552).
Die Fungizide der Formeln II bis III sind ebenfalls bekannt und in der Literatur beschrieben. Darüber hinaus sind sie unter den nachfolgend in Klammern genannten Handelsnamen kommerziell erhältlich: 5The fungicides of the formulas II to III are also known and are described in the literature. They are also commercially available under the trade names below in brackets: 5
II: EP 313,512, vorgeschlagener Common name: Acibenzolar (Han- delsname:Bion® , Fa. Novartis)II: EP 313,512, proposed common name: Acibenzolar (trade name: Bion®, Novartis)
III: Common name: Probenazol (Handelsname Oryzamate®, Fa. Meiji Seika)III: Common name: probenazole (trade name Oryzamate®, Meiji Seika)
Die Verbindungen I können bei der Herstellung aufgrund ihrer C=C und C=N Doppelbindungen als E/Z-Isomerengemische anfallen, die z.B. durch Kristallisation oder Chromatographie in üblicher Weise in die Einzelverbindungen getrennt werden können.Due to their C = C and C = N double bonds, the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
Sofern bei der Synthese Isomerengemische anfallen, ist im allgemeinen jedoch eine Trennung nicht unbedingt erforderlich, da sich die einzelnen Isomere teilweise während der Aufbereitung für die Anwendung oder bei der Anwendung (z.B. unter Licht-, Säureoder Baseneinwirkung) ineinander umwandeln können. Entsprechende Umwandlungen können auch nach der Anwendung, beispielsweise bei der Behandlung von Pflanzen in der behandelten Pflanze oder im zu bekämpfenden Schadpilz oder tierischen Schädling erfolgen.If isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
In Bezug auf die C=X Doppelbindung werden hinsichtlich ihrer Wirksamkeit die E-Isomere der Verbindungen I bevorzugt (Konfiguration bezogen auf die -OCH3 bzw. die -CH3 -Gruppe im Verhältnis zur -CO2R1 Gruppe) .With regard to the C = X double bond, the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
In Bezug auf die -C (R3) =NOCH2- Doppelbindung werden hinsichtlich ihrer Wirksamkeit die cis-Isomere der Verbindungen I bevorzugt (Konfiguration bezogen auf den Rest R3 im Verhältnis zur -OCH2- Gruppe) .With regard to the -C (R 3 ) = NOCH 2 double bond, the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
Bei der eingangs angegebenen Definitionen der Verbindungen I wurden Sammelbegriffe verwendet, die allgemein repräsentativ für die folgenden Gruppen stehen:In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:
Halogen: Fluor, Chlor, Brom und Jod;Halogen: fluorine, chlorine, bromine and iodine;
Alkyl : geradkettige oder verzweigte Alkylgruppen mit 1 bis 4, 6 oder 10 Kohlenstoffatomen, z.B. Ci-Cg-Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methyl-propyl , 2-Methylpropyl , 1, 1-Dirnethylethyl, Pentyl, 1-Methylbutyl , 2-Methylbutyl , 3-Methylbutyl, 2 , 2-Di-methylpropyl , 1-Ethylpropyl , Hexyl , 1, 1-Dimethylpropyl , 1 , 2-Dimethylpropyl , 1-Methylpentyl , 2-Methyl- pentyl , 3-Methylpentyl , 4-Methylpentyl , 1, 1-Dimethylbutyl, 1,2-Dirnethylbutyl, 1 , 3-Dimethylbutyl , 2 , 2-Dimethylbutyl , 2, 3-Dimethylbutyl, 3 , 3-Dimethylbutyl , 1-Ethylbutyl , 2-Ethylbutyl , 6Alkyl: straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example Ci-Cg-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dirnethylethyl , Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl , 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2 -Ethylbutyl, 6
1, 1, 2-Trimethylpropyl, 1 , 2 , 2-Trimethylpropyl , 1-Ethyl-l-methyl - propyl und 1- Ethyl-2-methylpropyl;1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl and 1-ethyl-2-methylpropyl;
Halogenalkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. Cι-C2-Halogenalkyl wie Chlormethyl, Dichlor ethyl, Trichlormethyl , Fluormethyl, Difluor- methyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 1-Fluorethyl, 2-Fluorethyl, 2 , 2-Difluorethyl, 2, 2, 2-Trifluorethyl, 2-Chlor-2-fluorethyl , 2-Chlor-2 , 2-difluorethyl, 2, 2-Dichlor-2-fluorethyl, 2 , 2 , 2-Trichlorethyl und Penta- fluorethyl ;Haloalkyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloroethyl, trichloromethyl, fluoromethyl, difluoromethyl , Trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2 , 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl and pentafluoroethyl;
Cycloalkyl : monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoff - ringgliedern, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl ;Cycloalkyl: monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Alkenyl : geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 oder 10 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-Cg-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-l-propenyl, 2-Methyl-l-propenyl, l-Methyl-2-propenyl , 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1-Methyl-l-butenyl, 2-Methyl-l-butenyl, 3-Methyl-l- butenyl, l-Methyl-2-butenyl , 2-Methyl-2-butenyl , 3-Methyl-2- butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl , 3-Methyl-3- butenyl, 1, l-Dimethyl-2-propenyl, 1, 2-Dimethyl-l-propenyl, 1, 2-Dimethyl-2-propenyl, 1-Ethyl-l-propenyl , l-Ethyl-2-propenyl , 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl,Alkenyl: straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -Cg-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl , 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4th -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, l-dimethyl-2-propenyl, 1, 2-dimethyl-l-propenyl, 1, 2-dimethyl -2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,
1-Methyl-l-pentenyl, 2-Methyl-l-pentenyl, 3-Methyl-l-pentenyl , 4-Methyl-l-pentenyl, l-Methyl-2-pentenyl , 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl , l-Methyl-3-pentenyl , 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl , 4-Methyl-3-pentenyl, l-Methyl-4-pentenyl, 2-Methyl-4-pentenyl , 3-Methyl-4-pentenyl , 4-Methyl-4-pentenyl, 1, l-Dimethyl-2-butenyl , 1, l-Di-methyl-3- butenyl, 1 , 2-Dimethyl-l-butenyl , 1, 2-Dimethyl-2-butenyl, 1, 2-Dimethyl-3-butenyl, 1, 3-Dimethyl-l-butenyl , 1 , 3-Dimethyl-2- butenyl, 1 , 3-Dimethyl-3-butenyl , 2 , 2-Dimethyl-3-butenyl, 2, 3-Dimethyl-l-butenyl, 2 , 3-Dimethyl-2-butenyl , 2 , 3-Dimethyl-3- butenyl, 3 , 3-Dimethyl-l-butenyl, 3 , 3-Dimethyl-2-butenyl, 1-Ethyl-l-butenyl, l-Ethyl-2-butenyl , l-Ethyl-3-butenyl , 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl , 2-Ethyl-3-butenyl , 1, 1, 2-Trimethyl-2-propenyl, 1- Ethyl-l-methyl-2-propenyl , l-Ethyl-2-methyl-l-propenyl und l-Ethyl-2-methyl-2-propenyl ; 71-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3- Methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl- 4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, l-dimethyl-2-butenyl, 1, l-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-l-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl- l-propenyl and l-ethyl-2-methyl-2-propenyl; 7
Alkinyl : geradkettige oder verzweigte Alkinylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, z.B. C -Cg-Alkinyl wie Ethinyl, 2-Propinyl, 2-Butinyl, 3-Butinyl, l-Methyl-2-propinyl , 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2-butinyl , l-Methyl-3-butinyl , 2-Methyl-3-butinyl, 1, l-Dimethyl-2-propinyl , l-Ethyl-2-propinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, l-Methyl-2-pentinyl , l-Methyl-3-pentinyl, l-Methyl-4-pentinyl , 2-Methyl-3-pentinyl , 2-Methyl-4-pentinyl, 3-Methyl-4-pentinyl , 4-Methyl-2-pentinyl , 1, l-Dimethyl-2-butinyl, 1 , l-Dimethyl-3-butinyl , 1 , 2-Dimethyl- 3-butinyl, 2 , 2-Dimethyl-3-butinyl , l-Ethyl-2-butinyl , 1-Ethyl- 3-butinyl, 2-Ethyl-3-butinyl und l-Ethyl-l-methyl-2-propinyl ;Alkynyl: straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, e.g. C -Cg-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l- Methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l- Methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl- 2-pentynyl, 1, l-dimethyl-2-butynyl, 1, l-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2, 2-dimethyl-3-butynyl, l-ethyl-2- butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l-methyl-2-propynyl;
Heterocyclyl bzw. Heterocyclyloxy, Heterocyclylthio und Hetero- cyclylamino: drei- bis sechsgliedrige, gesättigte oder partiell ungesättigte mono- oder polycyclische Heterocyclen, die ein bis drei Hereroatome ausgewählt aus einer Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel enthalten, und welche direkt bzw. (Heterocyclyloxy) über ein Sauerstoffatom oder (Heterocyclylthio) über ein Schwefelatom oder (Heterocyclylamino) über ein Stickstoffatom an das Gerüst gebunden sind, wie z.B. 2 -Tetrahydro- f ranyl , Oxiranyl, 3 -Tetrahydrofuranyl, 2 -Tetrahydrothienyl, 3 -Tetrahydrothienyl, 2 - Pyrrolidinyl , 3 - Pyrrolidinyl, 3-Isoxazol- dinyl, 4 -Isoxazolidinyl, 5 -Isoxazolidinyl , 3 -Isothiazolidinyl, 4 -Isothiazolidinyl , 5 - Isothiazolidinyl , 3 - Pyrazolidinyl ,Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclyllamino: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or ( Heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example 2-tetrahydrofranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazol-dinyl, 4 -isoxazolidinyl, 5 -isoxazolidinyl, 3 -isothiazolidinyl, 4-isothiazolidinyl , 5 - isothiazolidinyl, 3 - pyrazolidinyl,
4 - Pyrazolidinyl, 5 -Pyrazolidinyl , 2 -Oxazolidinyl , 4 -Oxazolidinyl , 5 -Oxazolidinyl, 2 -Thiazolidinyl , 4 -Thiazolidinyl , 5-Thia- zolidinyl, 2 - Imidazolidinyl , 4 -Imidazolidinyl , 1,2,4-Oxa- diazolidin-3 -yl, 1,2,4 -Oxadiazolidin- 5 -yl , 1,2,4 -Thiadiazolidin- 3-yl, 1, 2, 4 -Thiadiazolidin- 5 -yl, 1 , 2 , 4 -Triazolidin-3 -yl , l,3,4-Oxadiazolidin-2-yl, 1 , 3 , 4 -Thiadiazolidin-2 -yl , 1,3,4-Tri- azolidin-2 -yl, 2 , 3 -Dihydrofur-2 -yl , 2 , 3 -Dihydrofur-3 -yl , 2, 3-Dihydro-fur-4-yl, 2, 3 -Dihydro-fur- 5 -yl , 2, 5 -Dihydro-fur-2 -yl , 2, 5-Dihydro-fur-3-yl, 2 , 3 -Dihydrothien-2 -yl , 2,3-Dihydro- thien-3-yl, 2 , 3 -Dihydrothien-4 -yl , 2 , 3 -Dihydrothien- 5 -yl , 2,5-Dihydrothien-2-yl, 2 , 5 -Dihydrothien- 3 -yl , 2,3-Dihydro- pyrrol-2-yl, 2 , 3 -Dihydropyrrol - 3 -yl , 2 , 3 -Dihydropyrrol -4 -yl , 2 , 3 -Dihydropyrrol -5 -yl, 2 , 5 -Dihydropyrrol - 2 -yl , 2, 5 -Dihydropyrrol - 3 -yl , 2,3 -Dihydroisoxazol - 3 -yl , 2,3 -Dihydroisoxazol -4 -yl , 2, 3 -Dihydroisoxazol -5 -yl, 4 , 5 -Dihydroisoxazol - 3 -yl , 4, 5 -Dihydroisoxazol -4 -yl, 4 , 5 -Dihydroisoxazol -5 -yl , 2 , 5 -Dihydroisothia- zol -3 -yl, 2,5 -Dihydroisothiazol -4 -yl , 2,5 -Dihydroisothiazol - 5 -yl, 2 , 3 -Dihydroisopyrazol-3 -yl , 2,3 -Dihydroisopyrazol -4 -yl , 2,3 -Dihy- droisopyrazol-5 -yl, 4 , 5 -Dihydroisopyrazol - 3 -yl, 4 , 5 -Dihydroiso- pyrazol -4 -yl, 4 , 5 -Dihydroisopyrazol - 5 -yl , 2 , 5 -Dihydroisopyrazol - 3 -yl , 2,5 -Dihydroisopyrazol - 4 -yl , 2,5 -Dihydroisopyrazol - 5 -yl , 2, 3 -Dihydrooxazol-3 -yl , 2 , 3 -Dihydrooxazol -4 -yl , 2,3-Dihydro- 8 oxazol-5-yl, 4 , 5 -Dihydrooxazol - 3 -yl , 4 , 5 -Dihydrooxazol -4 -yl , 4 , 5 -Dihydrooxazol -5 -yl , 2 , 5 -Dihydrooxazol - 3 -yl , 2,5-Dihydro- oxazol-4-yl, 2 , 5 -Dihydrooxazol -5 -yl, 2 , 3 -Dihydrothiazol -2 -yl, 2 , 3 -Dihydrothiazol-4 -yl , 2 , 3 -Dihydrothiazol - 5 -yl , 4,5-Dihydro- thiazol-2-yl, 4 , 5 -Dihydrothiazol -4 -yl , 4 , 5 -Dihydrothiazol - 5 -yl , 2 , 5 -Dihydrothiazol -2 -yl , 2 , 5 -Dihydrothiazol -4 -yl, 2,5-Dihydro- thiazol - 5 -yl , 2,3 -Dihydroimidazol -2 -yl , 2,3 -Dihydroimidazol -4 -yl , 2 , 3 -Dihydroimidazol -5 -yl, 4 , 5 -Dihydroimidazol - 2 -yl, 4 , 5 -Dihydroimidazol -4 -yl , 4, 5 -Dihydroimidazol -5 -yl, 2 , 5 -Dihydroimidazol - 2-yl, 2 , 5 -Dihydroimidazol -4 -yl, 2 , 5 -Dihydroimidazol -5 -yl , 2 -Morpholinyl , 3 -Morpholinyl, 2 - Piperidinyl , 3 -Piperidinyl , 4 -Piperidinyl, 3 -Tetrahydropyridazinyl , 4 -Tetrahydropyridazinyl, 2 -Tetrahydropyrimidinyl, 4 -Tetrahydropyrimidinyl , 5 -Tetrahydro- pyrimidinyl, 2 -Tetrahydropyrazinyl , 1,3,5 -Tetrahydrotriazin-2 -yl, 1, 2 , 4 -Tetrahydrotriazin-3 -yl, 1, 3 -Dihydrooxazin-2 -yl ,4 - pyrazolidinyl, 5 -pyrazolidinyl, 2 -oxazolidinyl, 4 -oxazolidinyl, 5 -oxazolidinyl, 2 -thiazolidinyl, 4 -thiazolidinyl, 5-thiazolidinyl, 2 - imidazolidinyl, 4 -imidazolidinyl, 1,2,4-oxa- diazolidin-3 -yl, 1,2,4 -oxadiazolidin- 5 -yl, 1,2,4 -thiadiazolidin- 3-yl, 1, 2, 4 -thiadiazolidin- 5 -yl, 1, 2, 4 -triazolidin 3 -yl, l, 3,4-oxadiazolidin-2-yl, 1, 3, 4 -thiadiazolidin-2 -yl, 1,3,4-triazolidin-2 -yl, 2, 3 -dihydrofur-2 - yl, 2,3-dihydrofur-3-yl, 2,3-dihydro-fur-4-yl, 2,3-dihydro-fur-5-yl, 2,5-dihydro-fur-2-yl, 2, 5-dihydro-fur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydro-thien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5 - yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydro-pyrrol-2-yl, 2,3-dihydropyrrole - 3-yl, 2,3-dihydropyrrole - 4 -yl, 2, 3 -dihydropyrrole -5 -yl, 2, 5 -dihydropyrrole - 2 -yl, 2, 5 -dihydropyrrole - 3 -yl, 2,3 -dihydroisoxazole - 3 -yl, 2,3 -dihydroisoxazole - 4 -yl, 2,3-dihydroisoxazole -5 -yl, 4, 5 -dihydroisoxazole - 3 -yl, 4, 5 -dihydroisoxazole -4 -yl, 4, 5 -dihydroisoxazole -5 -yl, 2, 5 -dihydroisothiazole -3 -yl, 2.5 -Dihydroisothiazole -4 -yl, 2,5 -Dihydroisothiazol-5 -yl, 2, 3 -Dihydroisopyrazol-3 -yl, 2,3 -Dihydroisopyrazol -4 -yl, 2,3 -Dihydroisopyrazol-5 -yl, 4 , 5 -Dihydroisopyrazol - 3 -yl, 4, 5 -Dihydroisopyrazol - 4 -yl, 4, 5 -Dihydroisopyrazol - 5 -yl, 2, 5 -Dihydroisopyrazol - 3 -yl, 2,5 -Dihydroisopyrazol - 4 -yl , 2,5-dihydroisopyrazole - 5 -yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazole -4-yl, 2,3-dihydro- 8 oxazol-5-yl, 4,5-dihydrooxazole -3 -yl, 4,5-dihydrooxazole -4-yl, 4,5-dihydrooxazole -5-yl, 2,5-dihydrooxazole-3-yl, 2,5 -Dihydro-oxazol-4-yl, 2, 5 -dihydrooxazole -5 -yl, 2, 3 -dihydrothiazole -2 -yl, 2, 3 -dihydrothiazol-4 -yl, 2, 3 -dihydrothiazole - 5 -yl, 4 , 5-Dihydro-thiazol-2-yl, 4, 5 -dihydrothiazol -4 -yl, 4, 5 -dihydrothiazol-5 -yl, 2, 5 -dihydrothiazole -2 -yl, 2, 5 -dihydrothiazole -4 -yl , 2,5-dihydro-thiazole - 5 -yl, 2,3-dihydroimidazole -2-yl, 2,3-dihydroimidazole -4-yl, 2,3-dihydroimidazole -5-yl, 4,5-dihydroimidazole - 2 -yl, 4, 5 -dihydroimidazole -4 -yl, 4, 5 -dihydroimidazole -5 -yl, 2, 5 -dihydroimidazole - 2-yl, 2, 5 -dihydroimidazole -4 -yl, 2, 5 -dihydroimidazole -5 -yl, 2 -morpholinyl, 3 -morpholinyl, 2 -piperidinyl, 3 -piperidinyl, 4 -piperidinyl, 3 -tetrahydropyridazinyl, 4 -tetrahydropyridazinyl, 2 -tetrahydropyrimidinyl, 4 -tetrahydropyrimidinyl, 5 -tetrahydropyrimidinyl, 2 -tetrahydrop , 3.5 tetra hydrotriazin-2 -yl, 1, 2, 4-tetrahydrotriazin-3 -yl, 1, 3 -dihydrooxazin-2 -yl,
1, 3 -Dithian-2 -yl, 2 -Tetrahydropyranyl , 1 , 3 -Dioxolan-2 -yl , 3,4,5,6 -Tetrahydropyridin-2 -yl, 4H- 1, 3 -Thiazin-2 -yl, 4H-3 , l-Benzothiazin-2 -yl , 1, l-Dioxo-2 ,3,4,5- tetrahydrothien-2 -yl, 2H- 1, 4 -Benzothiazin-3 -yl, 2H- 1 , 4 -Benzoxazin-3 -yl , 1,3-Dihydro- oxazin-2-yl, 1 , 3 -Dithian-2 -yl ,1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3, -thiazin-2-yl, 4H-3, l-benzothiazin-2 -yl, 1, l-dioxo-2, 3,4,5-tetrahydrothien-2 -yl, 2H- 1, 4-benzothiazin-3 -yl, 2H- 1, 4 - Benzoxazin-3 -yl, 1,3-dihydro-oxazin-2-yl, 1, 3-dithian-2 -yl,
Aryl bzw. Aryloxy, Arylthio, Arylcarbonyl und Arylsulfonyl : aromatische mono- oder polycyclische Kohlenwasserstoffreste welche direkt bzw. (Aryloxy) über ein Sauerstoffatom (-0-) oder (Arylthio) ein Schwefelatom (-S-), (Arylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Arylsulfonyl) über eine Sulfonyl - gruppe (-SO2-) an das Gerüst gebunden sind, z.B. Phenyl, Naphthyl und Phenanthrenyl bzw. Phenyloxy, Naphthyloxy und Phenanthrenyl- oxy und die entsprechenden Carbonyl- und Sulfonylreste;Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) are attached to the skeleton via a sulfonyl group (-SO 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
Hetaryl bzw. Hetaryloxy, Hetarylthio, Hetarylcarbonyl und Hetarylsulfonyl : aromatische mono- oder polycyclische Reste welche neben Kohlenstoffringgliedern zusätzlich ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Sauer- stoff- oder ein Schwefelatom oder ein Sauerstoff- oder einHetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, also contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one
Schwefelatom enthalten können und welche direkt bzw. (Hetaryloxy) über ein Sauerstoffatom (-0-) oder (Hetarylthio) ein Schwefelatom (-S-), (Hetarylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Hetarylsulfonyl) über eine Sulfonylgruppe (-S02-) an das Gerüst gebunden sind, z.B.Can contain sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-), (hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group ( -S0 2 -) are bound to the scaffold, e.g.
5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoff - atome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoff - atomen ein bis drei Stickstoffatome als Ringglieder enthalten können, z.B. 2-Pyrrolyl, 3-Pyrrolyl, 3-Pyrazolyl,5-membered heteroaryl containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,
4-Pyrazolyl, 5-Pyrazolyl, 2-Imidazolyl , 4-Imidazolyl , l,2,4-Triazol-3-yl und 1 , 3 , 4-Triazol-2-yl ; 94-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, l, 2,4-triazol-3-yl and 1, 3, 4-triazol-2-yl; 9
5-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoff - atome oder ein bis drei Stickstoffatome und ein Schwefeloder Sauerstoffatom oder ein Sauerstoff oder ein Schwefel - atom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoff - atomen ein bis vier Stickstoffatome oder ein bis drei Stick- stoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder Schwefelatom als Ringglieder enthalten können, z.B. 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 2-Pyrrolyl, 3-Pyrrolyl, 3-Isoxazolyl, 4-Isoxazolyl, 5-Isoxazolyl, 3-Isothiazolyl , 4-Isothiazolyl , 5-Isothiazolyl , 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-Imidazolyl , 4-Imidazolyl , 1 , 2 , 4-Oxadiazol- 3-yl, l,2,4-Oxadiazol-5-yl, 1 , 2 , 4-Thiadiazol-3-yl , l,2,4-Thiadiazol-5-yl, 1, 2 , 4-Triazol-3-yl ,5-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms can contain atomic atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazole 3-yl, l, 2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3- yl,
1,3, 4-Oxadiazol-2-yl, 1,3, 4-Thiadiazol-2-yl , 1,3, 4-Triazol-2-yl ;1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl;
benzokondensiertes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome oder ein Stickstoffatom und/oder ein Sauerstoff- oder Schwefelatom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder ein Schwefelatom als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglieder oder ein Stickstoff- und ein benachbartes Kohlenstoffringglied durch eine Buta-1 , 3-dien- 1 , 4-diylgruppe verbrückt sein können;Benzo-fused 5-membered heteroaryl, containing one to three nitrogen atoms or one nitrogen atom and / or one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or may contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1, 3-diene-1, 4-diyl group;
über Stickstoff gebundenes 5-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome, oder über Stickstoff gebundenes benzokondensiertes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stick - stoffatome bzw. ein bis drei Stickstoffatome als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlen¬ stoffringglieder oder ein Stickstoff- und ein benachbartes Kohlenstoffringglied durch eine Buta-1 , 3-dien- 1, 4-diylgruppe verbrückt sein können, wobei diese Ringe über eines der Stickstoffringglieder an das Gerüst gebunden sind;5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or 5-membered heteroaryl bonded via nitrogen-bonded benzo-condensed, containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms may contain as ring members, and in which two adjacent carbon ¬ carbon ring members or one nitrogen and one adjacent carbon ring member by a buta-1, 3-dien-1, 4-diyl group may be bridged, where these rings one of the nitrogen ring members to the scaffold are bound;
6-gliedriges Heteroaryl, enthaltend ein bis drei bzw. ein bis vier Stickstoffatome: 6-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis drei bzw. ein bis vier Stickstoff - atome als Ringglieder enthalten können, z.B. 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 3-Pyridazinyl , 4-Pyridazinyl , 2-Pyrimidinyl, 4-Pyrimidinyl , 5-Pyrimidinyl , 2-Pyrazinyl, 106-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4 -Pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 10
1 , 3 , 5-Triazin-2 -yl , 1 , 2 , 4-Triazin-3 -yl und 1 , 2 , 4 , 5 - Tetrazin - 3 - yl ;1, 3, 5-triazin-2 -yl, 1, 2, 4-triazin-3 -yl and 1, 2, 4, 5 - tetrazin-3-yl;
benzokondensiertes 6-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome: 6 -Ring Heteroarylgruppen in welchen zwei benachbarte Kohlenstoffringglieder durch eine Buta- 1, 3 -dien-1, 4 -diylgruppe verbrückt sein können, z.B. Chinolin, Isochinolin, Chinazolin und Chinoxalin,benzo-fused 6-membered heteroaryl containing one to four nitrogen atoms: 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta- 1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
bzw. die entsprechenden Oxy-, Thio-, Carbonyl- oder Sulfonyl- gruppen.or the corresponding oxy, thio, carbonyl or sulfonyl groups.
Hetarylamino: aromatische mono- oder polycyclische Reste, welche neben Kohlenstoffringgliedern zusätzlich ein bis vier Stickstoff - atome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom enthalten können und welche über ein Stickstoff - atom an das Gerüst gebunden sind.Hetarylamino: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
Die Angabe "partiell oder vollständig halogeniert" soll zum Aus - druck bringen, daß in den derart charakterisierten Gruppen die Wasserstoffatome zum Teil oder vollständig durch gleiche oder verschiedene Halogenatome wie vorstehend genannt ersetzt sein könne .The expression "partially or fully halogenated" is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above.
Im Hinblick auf ihre biologische Wirkung sind Verbindungen der Formel I bevorzugt, in denen m für 0 steht.With regard to their biological action, preference is given to compounds of the formula I in which m is 0.
Gleichermaßen bevorzugt sind Verbindungen der Formel I, in denen R1 für Methyl steht.Likewise preferred are compounds of formula I in which R 1 is methyl.
Daneben werden Verbindungen I bevorzugt, in denen R3 für Wasserstoff, Cyano, Cyclopropyl, Methyl, Ethyl, 1 -Methylethyl oder CF3 steht.In addition, compounds I are preferred in which R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
Außerdem werden Verbindungen I bevorzugt, in denen R3 für Methyl steht .In addition, compounds I are preferred in which R 3 is methyl.
Daneben werden Verbindungen I bevorzugt, in denen R3 für Cyano steht.In addition, compounds I are preferred in which R 3 is cyano.
Weiterhin werden Verbindungen I bevorzugt, in denen R3 für Cyclopropyl steht.Furthermore, compounds I are preferred in which R 3 is cyclopropyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R3 für CF3 steht. 11Furthermore, compounds I are preferred in which R 3 is CF 3 . 11
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für Wasserstoff, Cyclopropyl, Methyl, Ethyl, iso-Propyl, ggf. subst. Aryl oder Hetaryl steht.Furthermore, compounds I are preferred in which R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, optionally subst. Aryl or hetaryl is.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Methyl steht.In addition, compounds I are preferred in which R 5 is methyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für Ethyl steht.Furthermore, compounds I are preferred in which R 5 is ethyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Iso-Propyl steht.In addition, compounds I are preferred in which R 5 is isopropyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Cyclo- propyl steht.In addition, compounds I are preferred in which R 5 is cyclopropyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für CF3 steht .In addition, compounds I are preferred in which R 5 is CF 3 .
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Aryl oder Hetaryl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Aryl or hetaryl is.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Pyridyl, Pyrimidyl, Pyrazinyl, Pyridazinyl oder Triazinyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Furyl , Thienyl oder Pyrrolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Furyl, thienyl or pyrrolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Oxazolyl, Thiazolyl, Isoxazolyl, Isothiazolyl , Pyrazolyl oder Imidazolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Oxdiazolyl, Thiadiazolyl oder Triazolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Phenyl steht, welches unsubstituiert ist oder ein oder zwei der folgenden Gruppen trägt: Nitro, Cyano, Hydroxy, Amino, Ammocarbonyl , Aminothiocarbonyl, Halogen, Cι-C4-Alkyl, Cι-C4~Halogenalkyl , Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy, Cι-C4-Alkylamino, Di-Cι-C - Alkylamino, Cι-C -Alkylsulfonyl , Cι-C -Alkoxycarbonyl , Cι~C -Alkyl- aminocarbonyl oder Di-Cι-C4-Alkylaminocarbonyl . 12In addition, compounds I are preferred in which R 5 is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, ammocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 ~ haloalkyl, -C-C 4 alkoxy, -C-C 4 -haloalkoxy, Cι-C 4 -alkylamino, di-Cι-C - alkylamino, Cι-C -alkylsulfonyl, Cι-C-alkoxycarbonyl, Cι-C -alkyl - Aminocarbonyl or Di-Cι-C 4 alkylaminocarbonyl. 12
Außerdem werden Verbindungen I bevorzugt, denen R4 für Wasserstoff, Ci-Cg-Alkyl, C2-Cg-Alkenyl, C2 -C -Alk yl , Allyl, Arylalkyl, Hetarylalkyl, Aryloxyalkyl , Hetaryloxyalkyl , Aryl oder Hetaryl steht.In addition, compounds I are preferred in which R 4 represents hydrogen, Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -C -alkyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
Des weiteren werden Verbindungen I bevorzugt, m denen R4 für Ci-Cg-Alkyl steht.Furthermore, compounds I are preferred in which R 4 is C 1 -C 6 -alkyl.
Weitere bevorzugte Verbindungen I sind der WO 97/15,552 zu ent- nehmen.Further preferred compounds I can be found in WO 97 / 15,552.
Die m den erfmdungsgemaßen Mischungen enthaltenen Verbindungen I zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere gegen Pilze aus den Klassen der Ascomyceten, Deuteromyceten, Phycomyce- ten und Basidiomyceten aus.The compounds I contained in the mixtures according to the invention are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular against fungi from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemuse- pflanzen (z.B. Gurken, Bohnen, Tomaten, Kartoffeln und Kurbisgewachse) , Gerste, Gras, Hafer, Bananen, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wem, Weizen, Zierpflanzen, Zuckerrohr sowie an einer Vielzahl von Samen.They are particularly important for combating a large number of fungi on various crops such as cotton, vegetable plants (eg cucumber, beans, tomatoes, potatoes and pumpkin wax), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye , Soy, who, wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe grammis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fulig ea an Kurbisgewachsen, Podosphaera leucotπcha an Äpfeln, Uncmula necator an Reben, Puccmia-Arten an Getreide, Rhizoctoma-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuk- kerrohr, Venturia maequalis (Schorf) an Äpfeln, Helmmthospori - um-Arten an Getreide und Reis, Septoπa nodorum an Weizen, Botrytis cmera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudo- cercosporella herpotπchoides an Weizen und Gerste, Pyricularia oryzae an Reis und Rasen, Phytophthora mfestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Ar- ten m Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosphaerella-Arten Bananen sowie Fusaπum- und Verticillium- Arten.They are particularly suitable for combating the following phytopathogenic fungi: Erysiphe grammis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fulig ea on pumpkin plants, Podosphaera leucotπcha on apples, Uncmula necator on vines, Puccmia species on cereals, Rhizooma species , Rice and lawn, Ustilago species on cereals and sugar cane, Venturia maequalis (scab) on apples, Helmmthospori - um species on cereals and rice, Septoπa nodorum on wheat, Botrytis cmera (gray mold) on strawberries, vegetables, ornamental plants and Vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotπchoides on wheat and barley, Pyricularia oryzae on rice and lawn, Phytophthora mfestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species on hops and cucumbers, Alternaria species on vegetables and fruit, Mycosphaerella species bananas and Fusaπum and Verticillium species.
Die Verbindung II ist als sogenannter Resistenzinduktor (d.h. gegen Krankheitsbefall immunisierender Wirkstoff) kommerziell erhältlich, d.h. II bringt keine direkte fungizide Wirkung, sondern induziert m der behandelten Pflanze eine Resistent gegen Schadpilze. Verbindung III ist als Fungizid bekannt. 13Compound II is commercially available as a so-called resistance inducer (ie active ingredient immunizing against disease infestation), ie II does not have a direct fungicidal action, but instead induces resistance to harmful fungi in the treated plant. Compound III is known as a fungicide. 13
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I und II bis III ein, denen man weitere Wirkstoffe gegen Schadpilze oder gegen andere Schädlinge wie Insekten, Spinntiere oder Nematoden oder auch herbizide oder Wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann.When preparing the mixtures, preference is given to using the pure active ingredients I and II to III, 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.
Die Mischungen aus den Verbindungen I und mindestens einer Verbindung II b s III können gleichzeitig, gemeinsam oder getrennt angewandt werden und zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Basidiomyceten, Phy- comyceten und Deuteromyceten aus. Sie sind z.T. systemisch wirksam und können daher auch als Blatt- und Bodenfungizide emge- setzt werden.The mixtures of the compounds I and at least one compound II to III can be used simultaneously, together or separately and 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 foliar and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen, Tomaten, Kartoffeln und Kurbisge- wachse), Gerste, Gras, Hafer, Bananen, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wem, Weizen, Zierpflanzen, Zuckerrohr sowie an einer Vielzahl von Samen.They are particularly important for combating a large number of fungi on various crops such as cotton, vegetables (eg cucumber, beans, tomatoes, potatoes and pumpkin waxes), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye , Soy, who, wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe grammis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuligmea an Kurbisgewachsen, Podosphaera leucotπcha an Äpfeln, Uncmula necator an Reben, Puccmia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuk- kerrohr, Ventuπa maequalis (Schorf) an Äpfeln, Helmmthospoπ um-Arten an Getreide und Reis, Septoπa nodorum an Weizen, Botrytis cmera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudo- cercosporella herpotrichoides an Weizen und Gerste, Pyπculaπa oryzae an Reis und Rasen, Phytophthora mfestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Ar- ten Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosphaerella-Arten m Bananen sowie Fusaπu - und Verticillium- Arten.They are particularly suitable for combating the following phytopathogenic fungi: Erysiphe grammis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuligmea on vine plants, Podosphaera leucotπcha on apples, Uncmula necator on vines, Puccmia species on cereals, Rhizo species Rice and lawn, Ustilago species on cereals and sugar cane, Ventuπa maequalis (scab) on apples, Helmmthospoπ um species on cereals and rice, Septoπa nodorum on wheat, Botrytis cmera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudo-cercosporella herpotrichoides on wheat and barley, Pyπculaπa oryzae on rice and lawn, Phytophthora mfestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species on hops and cucumber, Alternaria species on vegetables and fruit Mycosphaerella species in bananas as well as Fusaπu and Verticillium species.
Besonders bevorzugt sind die erfmdungsgemaßen Mischungen zur Bekämpfung von Pyπculaπa oryzae einsetzbar.The mixtures according to the invention can be used with particular preference for controlling Pyπculaπa oryzae.
Die Verbindungen I und mindestens eine der Verbindungen II bis III können gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander aufgebracht werden, wobei die Reihenfolge bei ge- 14 trennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compounds 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 being 14 separate application generally has no effect on the success of the control.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen, vor allem bei landwirtschaftlichen Kulturflächen, je nach Art des gewünschten Effekts bei 0,01 bis 8 kg/ha, vorzugsweise 0,1 bis 5 kg/ha, insbesondere 0,5 bis 3,0 kg/ha.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 0.5 to 3.0 kg / ha, depending on the type of effect desired .
Die Aufwandmengen liegen dabei für die Verbindungen I bei 0,01 bis 2,5 kg/ha, vorzugsweise 0,05 bis 2,5 kg/ha, insbesondere 0,1 bis 1,0 kg/ha.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.
Die Aufwandmengen für die Verbindungen II bis III liegen entsprechend bei 0,001 bis 5 kg/ha, vorzugsweise 0,005 bis 2 kg/ha, ins - besondere 0,01 bis 1,0 kg/ha.The application rates for the compounds II to III are accordingly 0.001 to 5 kg / ha, preferably 0.005 to 2 kg / ha, in particular 0.01 to 1.0 kg / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,001 bis 250 g/kg Saatgut, vorzugsweise 0,01 bis 100 g/kg, insbesondere 0,01 bis 50 g/kg verwendet.In the case of seed treatment, 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.
Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind, erfolgt die getrennte oder gemeinsame Applikation der Verbindungen I und mindestens einer der Verbindungen II bis III durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.If pathogenic harmful fungi are to be combated for plants, the separate or joint application of the compounds I and at least one of the compounds II to III is carried out by spraying or dusting the seeds, the plants or the soil before or after the plants are sown or before or after the Emergence of plants.
Die erfindungsgemäßen fungiziden synergistischen Mischungen können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendungszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten.The fungicidal synergistic mixtures according to the invention 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, scattering agents or granules and by spraying, atomizing, dusting , Scattering or pouring can be applied. 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.
Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/oder Trägerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdünnungsmittel auch andere organische Lösungsmittel als Hilfslösungsmittel verwendet werden können. Als Hilfsstoffe kommen dafür im we- sentlichen in Betracht: Lösungsmittel wie Aromaten (z.B. Xylol) , chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol) , Ketone (z.B. Cy- 15 clohexanon) , Amme (z.B. Ethanolamm, Dirnethylform-amid) und Wasser; Tragerstoffe wie naturliche Geste smehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gestemsmehle (z.B. hochdisperse Kieselsaure, Silikate) ; Emulgiermittel wie nichtio- nogene und anionische Emulgatoren (z.B. Polyoxyethylen-Fettalko- hol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignmsulfitablaugen und Methylcellulose.The formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents. The following are essentially considered as auxiliaries: solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol), ketones (eg cyano 15 clohexanone), wet nurse (eg ethanolamm, dirnethylform amide) and water; Carriers such as natural gesture flour (eg kaolins, clays, talc, chalk) and synthetic starch flours (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignite sulfite waste liquors and methyl cellulose.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsauren, z.B. Lignm-,The alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignm,
Phenol-, Naphthalin- und Dibutylnaphthalmsulfonsaure, sowie von Fettsauren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolethern, Kondensationspro - dukte von sulfoniertem Naphthalin und seinen Derivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalmsulfonsauren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol- oder Tributylphenylpolyglycolether, Alkylarylpolyetheralkohole, Isotπdecylalkohol, Fettalkohol - ethylenoxid- Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- alkylether oder Polyoxypropylen, Laurylalkoholpolyglycoletherace- tat, Sorbitester, Lignm-Sulfitablaugen oder Methylcellulose m Betracht.Phenolic, naphthalene and dibutylnaphthalene sulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives, Condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotπdecyl alcohol, polyalkylene alcohol, polyethylenethoxy alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, - tat, sorbitol ester, lignm sulfite liquor or methyl cellulose.
Pulver Streu- und Staubemittel können durch Mischen oder gemeinsames Vermählen der Verbindungen I und mindestens einer der Verbindungen II bis III oder der Mischung aus den Verbindungen I und mindestens einer Verbindung II bis III mit einem festen Trager - Stoff hergestellt werden.Powder scattering and dusting agents can be prepared by mixing or grinding the compounds I and at least one of the compounds II to III or the mixture of the compounds I and at least one compound II to III with a solid carrier substance.
Granulate (z.B. Umhullungs-, Impragnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Tragerstoff hergestellt.Granules (e.g. coated granules, impregnated granules or homogeneous granules) are usually produced by binding the active ingredient or ingredients to a solid carrier.
Als Füllstoffe bzw. feste Tragerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsauren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Loß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat,Mineral soils such as silica gel, silica, 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 like ammonium sulfate,
Ammoniumphosphat, .Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Tragerstoffe.Ammonium phosphate, ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% einer der Verbindungen I und mindestens einer der Verbindungen II bis III bzw. der Mischung aus 16 den Veromdungen I und mindestens einer der Verbindungen II bis III. Die Wirkstoffe werden dabei m einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR- oder HPLC-Spektrum) eingesetzt.The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to III or the mixture of 16 Veromdungen 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).
Die Anwendung der entsprechenden Formulierungen erfolgt so, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Boden, Flachen, Materialien oder Räume mit einer fungizid wirksamen Menge der Mischung, bzw. der Verbindungen I und mindestens einer der Verbindungen II bis III bei getrennter Ausbringung, behandelt.The corresponding formulations are used in such a way that the harmful fungi, their habitat or the plants, seeds, soil, areas, materials or spaces to be kept free of them are mixed with a fungicidally effective amount of the mixture or of the compounds I and at least one of the compounds II to III for separate application.
Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen.The application can take place before or after the infestation by the harmful fungi.
Beispiele für solche Zubereitungen, welche die Wirkstoffe enthal ten, sind:Examples of such preparations that contain the active ingredients are:
I. eine Losung aus 90 Gew. -Teilen der Wirkstoffe und 10 Gew.- Teilen N-Methylpyrrolidon, die zur Anwendung in Form kleinster Tropfen geeignet ist;I. a solution of 90 parts by weight of the active ingredients and 10 parts by weight of N-methylpyrrolidone, which is suitable for use in the form of tiny drops;
II. eine Mischung aus 20 Gew. -Teilen der Wirkstoffe, 80 Gew.- Teilen Xylol, 10 Gew. -Teilen des Anlagerungsproduktes von 8 bis 10 Mol Et ylenoxid an 1 Mol Olsaure-N-monoethanolamid, 5 Gew. -Teilen Calciumsalz der Dodecylbenzolsulfonsaure, 5II. A mixture of 20 parts by weight of the active ingredients, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt Dodecylbenzenesulfonic acid, 5
Gew. -Teilen des .Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricmusol; durch feines Verteilen der Losung m Wasser erhalt man eine Dispersion;Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of ricmusol; a dispersion is obtained by finely distributing the solution in water;
III. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 40 Gew. -Teilen Cyclohexanon, 30 Gew. -Teilen Isobutanol, 20III. an aqueous dispersion of 20 parts by weight of the active ingredients, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20
Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricmusol;Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of ricmusol;
IV. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 25 Gew. -Teilen Cyclohexanol , 65 Gew. -Teilen einer Mme- ralolfraktion vom Siedepunkt 210 bis 280°C und 10 Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricmusol;IV. An aqueous dispersion of 20 parts by weight of the active ingredients, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide 1 mole of ricmusol;
V. eine m einer Hammermuhle vermahlene Mischung aus 80 Gew.- Teilen der Wirkstoffe, 3 Gew. -Teilen des Natriumsalzes der Dιιsobutylnaphthalm-1-sulfonsaure, 10 Gew. -Teilen des Natriumsalzes einer Lignmsulfonsaure aus einer Sulfitablauge und 7 Gew. -Teilen pulverformigem Kieselsauregel ; durch feines Verteilen der Mischung m Wasser erhalt man eine Spπtzbruhe; VI. eine innige Mischung aus 3 Gew. -Teilen der Wirkstoffe und 97 Gew. -Teilen feinteiligem Kaolin; dieses Staubemittel enthalt 3 Gew.-% Wirkstoff; 17V. a mixture of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalm-1-sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite liquor and 7 parts by weight of powdered mixture, ground in a hammer mill Silica rule; A fine boil is obtained by finely distributing the mixture in water; VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient; 17
VII. eine innige Mischung aus 30 Gew. -Teilen der Wirkstoffe, 92 Gew. -Teilen pulverförmigem Kieselsäuregel und 8 Gew. -Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde; diese Aufbereitung gibt dem Wirkstoff eine gute Haftfähigkeit;VII. An intimate mixture of 30 parts by weight of the active ingredients, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel; this preparation gives the active ingredient good adhesion;
VIII. eine stabile wäßrige Dispersion aus 40 Gew. -Teilen der Wirkstoffe, 10 Gew. -Teilen des Natriumsalzes eines Phenolsulfonsäure-Harnstoff-Formaldehyd-Kondensates , 2 Gew. -Teilen Kieselgel und 48 Gew. -Teilen Wasser, die weiter ver- dünnt werden kann;VIII. A stable aqueous dispersion of 40 parts by weight of the active ingredients, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which further dilutes can be;
IX. eine stabile ölige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 2 Gew. -Teilen des Calciumsalzes der Dodecylbenzol - sulfonsaure, 8 Gew. -Teilen Fettalkohol-polyglykolether, 20 Gew. -Teilen des Natriumsalzes eines Phenolsulfonsäure-Harn- stoff-Formaldehydkondensates und 88 Gew. -Teilen eines paraffinischen Mineralöls.IX. a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic 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.
Die synergistische Wirkung der erfindungsgemäßen Mischungen läßt sich durch die folgenden Versuche zeigen:The synergistic effect of the mixtures according to the invention can be demonstrated by the following experiments:
Die Wirkstoffe werden getrennt oder gemeinsam als 10%ige Emulsion in einem Gemisch aus 63 Gew.-% Cyclohexanon und 27 Gew.-% Emulga- tor aufbereitet und entsprechend der gewünschten Konzentration mit Wasser verdünnt.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.
Die Auswertung erfolgt durch Feststellung der befallenen Blattflächen in Prozent. Diese Prozent-Werte werden in Wirkungsgrade umgerechnet. Der Wirkungsgrad (W) wird nach der Formel von Abbot wie folgt bestimmt:The evaluation is carried out by determining the affected leaf areas in percent. These percentages are converted into efficiencies. Efficiency (W) is determined using Abbot's formula as follows:
= (1 - α) -100/ß= (1 - α) -100 / ß
α entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in %α corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 wiesen die behandelten Pflanzen keinen Befall auf.With an efficiency of 0, 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.
Die zu erwartenden Wirkungsgrade der Wirkstoffmischungen wurden nach der Colby Formel [R.S. Colby, Weeds 15., 20-22 (1967)] ermit-. telt und mit den beobachteten Wirkungsgraden verglichen. 18The 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. 18th
Colby Formel: E = x + y - x-y/100Colby formula: E = x + y - x-y / 100
zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs A in der Konzentration a y der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration bexpected efficiency, expressed in% of the untreated control, when using the mixture of active ingredients A and B in concentrations a and b the efficiency, expressed in% of the untreated control, when using active ingredient A in concentration ay the efficiency, expressed in% of the untreated control when using the active ingredient B in the concentration b
Anwendungsbeispiel 1 Wirksamkeit gegen Pyricularia oryzae (protektiv)Example of use 1 Activity against Pyricularia oryzae (protective)
Blätter von in Töpfen gewachsenen Reiskeimlingen der Sorte "Tai- Nong 67" wurden mit wäßriger Wirkstoffaufbereitung, die mit einer Stammlösung aus 10 % Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wurde, bis zur Tropfnässe besprüht. Am folgenden Tag wurden die Pflanzen mit einer wäßrigen Sporensuspension von Pyricularia oryzae inokuliert. Anschließend wurden die Versuchspflanzen in Klimakammern bei 22 - 24° C und 95 - 99 % relativer Luftfeuchtigkeit für 6 Tage aufgestellt. Dann wurde das Ausmaß der Befallsentwicklung auf den Blättern visuell ermitteltLeaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually
Die visuell ermittelten Werte für den Prozentanteil befallener Blattflächen wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel (Colby, S. R. (Calculating synergistic and anta- gonistic responses of herbicide Combinations" , Weeds , 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen.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, S.R. (Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies.
Als Komponente a) wurde folgende Verbindung I' eingesetzt:The following compound I 'was used as component a):
H3C.H 3 C.
O' O '
^O-CH, ^ O-CH,
C 3 C 3
Figure imgf000020_0001
Figure imgf000020_0001
Die Ergebnisse der Versuche sind den nachstehenden Tabellen 1 und 2 zu entnehmen: 19The results of the tests are shown in Tables 1 and 2 below: 19
Tabelle 1:Table 1:
Bsp. Wirkstoff Konz . in ppm Wirkungsgrad in % der unbeh. KontrolleExample active ingredient conc. in ppm efficiency in% of unh. control
IV ohne (100 % Befall) 0IV without (100% infestation) 0
2V Verbindung I' 2,0 20 0,5 02V connection I '2.0 20 0.5 0
3V Verbindung II 2,0 0 0,5 03V connection II 2.0 0 0.5 0
4V Verbindung III 2,0 0 0,5 0
Figure imgf000021_0001
4V connection III 2.0 0 0.5 0
Figure imgf000021_0001
Tabelle 2:Table 2:
Bsp. erfindungsgemäße Mischung beobachteter berechneter (Konz . in ppm) Wirkungsgrad Wirkungsgrad*For example, the mixture of calculated calculated (conc. In ppm) efficiency according to the invention efficiency *
5 2 ppm I ' + 2 ppm II 40 205 2 ppm I '+ 2 ppm II 40 20
6 0,5 ppm I' + 0,5 ppm II 20 06 0.5 ppm I '+ 0.5 ppm II 20 0
7 2 ppm I ' + 2 ppm III 50 207 2 ppm I '+ 2 ppm III 50 20
8 0,5 ppm I' + 0,5 ppm III 25 0
Figure imgf000021_0002
8 0.5 ppm I '+ 0.5 ppm III 25 0
Figure imgf000021_0002
* berechnet nach der Colby-Formel* calculated according to the Colby formula
Aus den Ergebnissen der Versuche geht hervor, daß der beobachtete Wirkungsgrad in allen Mischungsverhältnissen höher ist als der nach der Colby-Formel vorausberechnete Wirkungsgrad. The results of the tests show that the observed efficiency in all mixing ratios is higher than the efficiency calculated according to the Colby formula.

Claims

2020th
Patentansprücheclaims
1. Mischungen für den Pflanzenschutz, enthaltend als aktive Kom- ponenten1. Mixtures for crop protection, containing as active components
a) Phenylessigsäurederivate der Formel Ia) Phenylacetic acid derivatives of the formula I.
:D: D
Figure imgf000022_0001
Figure imgf000022_0001
in der die Substituenten und der Index die folgende Be- deutung haben:in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3, CHCH3;X STILL 3 , CHOCH 3 , CHCH 3 ;
Y 0, NRY 0, NO
R^R unabhängig voneinander Wasserstoff und Cι-C4-Alkyl;R ^ R independently of one another hydrogen and -CC 4 alkyl;
R2 Cyano, Nitro, Trifluormethyl, Halogen, Cι-C -Alkyl und Cι~C4-Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, -CC alkyl and -C ~ C 4 alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Cyano, Cι-C4-Alkyl, Cι-C4-Halogen- alkyl, C3-C5-Cycloalkyl;R 3 is hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 halogen alkyl, C 3 -C 5 cycloalkyl;
R4,R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
CJ-Cio-Alkyl , C3-Cg-Cycloalkyl, C2-Cιo-Alkenyl , C2-Cι0-Alkinyl, Cι-Cι0-Alkylcarbonyl ,CJ-Cio-alkyl, C 3 -Cg-cycloalkyl, C 2 -Cιo-alkenyl, C 2 -Cι 0 -alkynyl, Cι-Cι 0 -alkylcarbonyl,
C2-Cιo-Alkenylcarbonyl , C -Cιo-Alkinylcarbonyl oder Cι-Cιo-Alkylsulfonyl , wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen kön- nen: Cyano, Nitro, Hydroxy, Mercapto, .Amino,C 2 -C 10 -alkenylcarbonyl, C -C 10 -alkynylcarbonyl or C 1 -C 8 -alkylsulfonyl, where these radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, .amino ,
Carboxyl, Ammocarbonyl , Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, 21Carboxyl, ammocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, 21
Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl , Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxy- carbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Cι~Cg-alkylamino,Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Cι ~ Cg- alkylamino,
Ci-Cg-Alkylaminocarbonyl , Di-Ci-Cg-alkylamino- carbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C2-Cg-Alkenyl , C2-Cg-Alkenyloxy, C3-Cg-Cycloalkyl, C3-Cg-Cycloalky- loxy, Heterocyclyl, Heterocyclyloxy, Benzyl,Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylamino-carbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyloxy, C 3 -Cg-cycloalkyl , C 3 -Cg-cycloalky- loxy, heterocyclyl, heterocyclyloxy, benzyl,
Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cyclischen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro,Benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro,
Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl , Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl, C3-Cg-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxycarbonyl ,Hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy , Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl,
Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-Alkyl - amino, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-Alkyl- .aminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-Ci-Cg-Alkylaminothiocarbonyl , C2-Cg-Alkenyl , C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy,Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkyl- .aminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg Alkylaminothiocarbonyl, C 2 -Cg alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,
Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C(=NOR7) -An-R8;Arylthio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl, Arylsulfonyl , Hetaryl, Het- arylcarbonyl oder Hetarylsulfonyl , wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl ,Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, halogen , Ci-Cg-alkyl, Ci-Cg-haloalkyl,
Ci-Cg-Alkylcarbonyl , Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl, C3-C5-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxycarbonyl , Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg- Alkylamino, Ci-Cg-Alkylaminocarbonyl ,Ci-Cg-alkylcarbonyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -C 5 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl,
Di-Ci-Cg-Alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyl , Di-Ci-Cg-Alkylaminothiocarbonyl , C2-Cg-Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy,, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C(=NOR7)-An-R8; 22 Wasserstoff,Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, Di-Ci-Cg-alkylaminothiocarbonyl, C 2 -Cg alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy ,, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 7 ) -A n -R 8 ; 22 hydrogen,
Ci-Cg-Alkyl, C2-Cg-Alkenyl, C2-Cg-Alkinyl, wobei die Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Aminothiocarbonyl, Halogen, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-alkylamino- carbonyl, Ci-Cg-Alkylaminothiocarbonyl ,Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -Cg-alkynyl, where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino , Carboxyl, ammocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylamino-carbonyl, Ci-Cg-alkylaminothiocarbonyl,
Di-Ci-Cg-alkylaminothiocarbonyl , Ci-Cg-Alkyl - sulfonyl, Ci-Cg-Alkylsulfoxyl , Ci-Cg-Alkoxy, Cι~Cg- Halogenalkoxy, Ci-Cg-Alkoxycarbonyl , Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-alkylamino, C2-Cg-Alkenyloxy, C3-Cg-Cycloalkyl , C3-Cg-Cycloalky- loxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cι-C4-alkoxy, Arylthio, Aryl-Cι-C4-alkyl- thio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C4-alkoxy, Hetarylthio, Hetaryl-Cι-C4-alkylthio, wobei die cy- clischen Reste ihrerseits partiell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, .Amino, Carboxyl, Ami\ocarbonyl, Aminothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl ,Di-Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-alkyl-sulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Cι ~ Cg- haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg- Alkylamino, di-Ci-Cg-alkylamino, C 2 -Cg-alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -Cg-cycloalky-loxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-Cι-C 4 -alkoxy, Arylthio, aryl -CC 4 -alkyl thio, hetaryl, hetaryloxy, hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC 4 -alkylthio, where the cyclic radicals in turn can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, .amino, carboxyl, ami \ ocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci -Cg alkyl sulfoxyl,
C3Cg-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylamino- carbonyl , Di-Ci-Cg-alkylaminocarbonyl , Cι~Cg-Alkyl- aminothiocarbonyl, Di-Ci-Cg-alkylaminothiocarbonyl ,C 3 Cg-cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino carbonyl, di-Ci-Cg-alkylaminocarbonyl, Cι ~ Cg-alkyl aminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl,
C2-Cg-Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C(=NOR7) -An-R8;C 2 -Cg alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 7 ) -A n -R 8 ;
C3-Cg-Cycloalkyl, C3 -Cg-Cycloalkenyl , Heterocyclyl,C 3 -Cg cycloalkyl, C 3 -Cg cycloalkenyl, heterocyclyl,
Aryl, Hetaryl, wobei die cyclischen Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , C -Cg-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxy- carbonyl, Ci-Cg-Alkylthio , Ci-Cg-Alkylamino, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylaminocarbonyl ,Aryl, hetaryl, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C -Cg-cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl,
Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-C -Cg-alkylaminothiocarbonyl , 23Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-C-Cg-alkylaminothiocarbonyl, 23
C -Cg-Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;C -Cg alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
wobeiin which
für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cg-Alkyl trägt;represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Cg-alkyl;
n 0 oder 1 bedeutet;n represents 0 or 1;
R7 Wasserstof f oder Ci-Cg-Alkyl bedeutet undR 7 represents hydrogen or Ci-Cg-alkyl and
R8 Wasserstoff oder Ci-Cg-Alkyl bedeutet,R 8 denotes hydrogen or Ci-Cg-alkyl,
sowie deren Salze,and their salts,
undand
mindestens eine Verbindung der Formeln II bis IIIat least one compound of the formulas II to III
(II)(II)
Figure imgf000025_0001
Figure imgf000025_0001
; IID
Figure imgf000025_0002
; IID
Figure imgf000025_0002
OCH2CH=CH2 OCH 2 CH = CH 2
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
Fungizide Mischung nach Anspruch 1, welche in zwei Teilen konditioniert ist, wobei der eine Teil die Verbindung I in einem festen oder flüssigen Träger enthält und der andere Teil mindestens eine der Verbindungen II bis III in einem festen oder flüssigen Träger enthält. 24A fungicidal mixture as claimed in claim 1 which is conditioned in two parts, one part containing the compound I in a solid or liquid carrier and the other part containing at least one of the compounds II to III in a solid or liquid carrier. 24
3. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Böden, Flächen oder Räume mit einer fungiziden Mischung gemäß einem der .Ansprüche 1 bis 2 behandelt, wobei die Anwendung der Verbindung I und mindestens einer der Verbindungen II bis III gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander erfolgen kann.3. A method for combating harmful fungi, characterized in that the fungi, their habitat or the materials, plants, seeds, soils, areas or spaces to be protected against fungal attack are treated with a fungicidal mixture according to one of the. Claims 1 to 2, wherein the compound I and at least one of the compounds II to III can be used simultaneously, that is jointly or separately, or in succession.
4. Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit 0,005 bis 1 kg/ha einer Verbindung I gemäß Anspruch 1 behandelt.4. The method according to claim 3, characterized in that treating the harmful fungi, their habitat or the plants, seeds, soils, surfaces, materials or spaces to be kept free by them with 0.005 to 1 kg / ha of a compound I according to claim 1.
5. Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit 0.01 bis 1 kg/ha mindestens einer der Verbindungen II bis IV gemäß Anspruch 1 behandelt. 5. The method according to claim 3, characterized in that the harmful fungi, their habitat or the plants, seeds, soils, surfaces, materials or spaces to be kept free of them with 0.01 to 1 kg / ha of at least one of the compounds II to IV according to claim 1 treated.
PCT/EP1999/001917 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and resistance inductors WO1999048370A1 (en)

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JP2000537436A JP4458668B2 (en) 1998-03-24 1999-03-22 Bactericidal mixture based on tris (oxime ether) derivatives and anti-inducing substances
CA002323593A CA2323593A1 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
AU33317/99A AU3331799A (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
IL13812599A IL138125A0 (en) 1998-03-24 1999-03-22 Fungicidal mixtures based on tris (oxime ether) derivatives and resistance inducers
EP99914531A EP1065929A1 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
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WO2005044002A2 (en) 2003-11-07 2005-05-19 Basf Aktiengesellschaft Mixtures comprising strobilurins and ethylene modulators
WO2006066810A2 (en) * 2004-12-20 2006-06-29 Basf Aktiengesellschaft Method for controlling mycoses in leguminous plants

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Cited By (9)

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Publication number Priority date Publication date Assignee Title
WO2002049434A1 (en) * 2000-12-18 2002-06-27 Basf Aktiengesellschaft Fungicide mixtures based on oxime ether derivatives
WO2005044002A2 (en) 2003-11-07 2005-05-19 Basf Aktiengesellschaft Mixtures comprising strobilurins and ethylene modulators
WO2005044002A3 (en) * 2003-11-07 2005-07-21 Basf Ag Mixtures comprising strobilurins and ethylene modulators
EA012044B1 (en) * 2003-11-07 2009-08-28 Басф Се Mixtures comprising strobilurins and ethylene modulators
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KR101126807B1 (en) 2003-11-07 2012-03-26 바스프 에스이 Mixtures comprising strobilurins and ethylene modulators
WO2006066810A2 (en) * 2004-12-20 2006-06-29 Basf Aktiengesellschaft Method for controlling mycoses in leguminous plants
WO2006066810A3 (en) * 2004-12-20 2006-09-21 Basf Ag Method for controlling mycoses in leguminous plants
EA012612B1 (en) * 2004-12-20 2009-10-30 Басф Акциенгезельшафт Method for controlling mycosis in leguminous plants

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