EP1065927A1 - Fungicide mixtures based on triple oxime ether derivatives and rhizoctonia fungicides - Google Patents

Fungicide mixtures based on triple oxime ether derivatives and rhizoctonia fungicides

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Publication number
EP1065927A1
EP1065927A1 EP99914529A EP99914529A EP1065927A1 EP 1065927 A1 EP1065927 A1 EP 1065927A1 EP 99914529 A EP99914529 A EP 99914529A EP 99914529 A EP99914529 A EP 99914529A EP 1065927 A1 EP1065927 A1 EP 1065927A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkylamino
hetaryl
aryl
alkylaminocarbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99914529A
Other languages
German (de)
French (fr)
Inventor
Klaus Schelberger
Thomas Grote
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1065927A1 publication Critical patent/EP1065927A1/en
Withdrawn legal-status Critical Current

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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
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A01N37/24—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/32—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing >N—CO—N< or >N—CS—N< groups directly attached to a cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms

Definitions

  • the present invention relates to fungicidal mixtures for combating harmful fungi which
  • Y is oxygen or NR
  • R ⁇ R independently of one another hydrogen or C 1 -C 4 alkyl, ⁇
  • R 2 cyano, nitro, trifluoromethyl, halogen, -CC alkyl or -C 4 alkoxy;
  • 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, C 4 -alkyl, C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 4 , R 6 are independently hydrogen
  • radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothio 2 carbonyi, halogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -haloalkyl, -C-C 6 -alkylsulfonyl, C ⁇ -C 6 -alkylsulfoxyl, C ⁇ -C 6 -alkoxy, Cx-C ⁇ -hal
  • Ci-Cg-alkylaminocarbonyl di-Ci-Cg-alkylaminocarbonyl
  • Ci-Cg-alkylaminothio-carbonyl di-Ci-Cg-alkylaminothiocarbonyl
  • Ci-Cg-alkyl - sulfonyl -CC 6 alkyl sulfoxyl
  • Ci-Cg-alkoxy -C ⁇ C 6 -
  • R 7 is hydrogen or Ci-Cg-alkyl
  • R 8 denotes hydrogen or Ci-Cg-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.
  • 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 are obtained 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 influence 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, e.g. Ci-Cg-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, 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,
  • Halocrenalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, Trif luormethyl, 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;
  • Cvcloalkyl 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,
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -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
  • Heterocyclyl or heterocvclyloxy, heterocvclylthio and heterocvclylamino 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 one Sulfur atom or (heterocyclylamino) are attached to the skeleton via a nitrogen atom, such as, for example 2-tetrahydrofuran, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazole-dinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 3-iso
  • 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 bonded to the skeleton via a sulfonyl group (-S0 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyl-oxy and the corresponding carbonyl and sulfonyl radicals;
  • 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 and 1, 3, 4-triazol-2- 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 and may contain 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-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen - Or can contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group;
  • Material ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;
  • 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, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,
  • 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,
  • R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 . 12
  • R 3 is 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 4 represents hydrogen, Ci-Cg-alkyl, C 2 -C 6 alkenyl, C 2 -Cg alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
  • the compounds I contained in the mixtures according to the invention are notable for an excellent action against a broad spectrum of phytopathogenic fungi, in particular against fungi from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.
  • the compounds II to VII are commercially available as fungicides.
  • the mixtures of the compounds I and at least one compound II to VII 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 leaf and soil fungicides.
  • the mixtures according to the invention can be used particularly preferably for controlling Pyricularia oryzae.
  • the compounds I and at least one of the compounds II to VII can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
  • the application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 kg, depending on the type of effect desired /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.
  • the application rates for the compounds II to VII 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 VII 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 Raising the 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.
  • 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. 16
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where in the case of water as diluent other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines ( eg ethanolamine, dimethylformamide) and water;
  • Carriers such as natural stone powder (e.g.
  • kaolins, clays, talc, chalk) and synthetic stone powder e.g. highly disperse silica, silicates
  • Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic 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 - aldehyde, condensation products of naphthalene or
  • Naphthalenesulfonic acids with phenol and formaldehyde polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol - ethylene oxide condensates, ethoxylated alkoxylated alcohol, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxyethyl ether -Sulfite waste or methyl cellulose into consideration.
  • Powder broadcasting and dusting agents can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to VII or the mixture of the compounds I and at least one compound II to VII with a solid carrier substance.
  • Granules e.g. coating, impregnation or homogeneous granules
  • a solid carrier e.g., a wax, a wax, or a wax.
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolo- 17 mit, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolo- 17 mit, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable
  • 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 VII or the mixture of the compounds I and at least one of the compounds II to VII.
  • 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, soils, surfaces, 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 VII treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • Os cd -H SH cd (H 0 rH ⁇ . RH 'S ⁇ -H rH ⁇ O cd d
  • CD rH CD H ro -rl MH rd D d tu CD CQ 1 £ xi CD -H N
  • CD MH cd d CD CD tn MH ⁇ 0. *. MH a CD 1 ⁇ SH d. rH xl MH ⁇ U xi rd rH MH xl -rl. 4-J Xl CQ -HOQ u cd CD 4-J CQ rH MH CD CD 'S CQ cd u SH ⁇ tJ * SH SH SH
  • CD CQ SH tn Xl CD rH MH CD -H CD d CD CD d 'S SH CQ - -HH l -rl -H d rH dd ⁇ tn ⁇ ⁇ - ⁇ r dd -H 4-J 2 U -rl CD -HO CD -H cd tn CD rH - cd CQ CD iH o CD rd CD * * SS D ⁇ Q rH NP -u CM PM
  • 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.

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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 (VII) in a synergistically effective quantity.

Description

Fungizide Mischungen auf der Basis von Tripeloximetherderivaten und Rhizoctonia-FungizidenFungicidal mixtures based on triple oxime ether derivatives and Rhizoctonia fungicides
Beschreibungdescription
Die vorliegende Erfindung betrifft fungizide Mischungen zur Bekämpfung von Schadpilzen, dieThe present invention relates to fungicidal mixtures for combating harmful fungi which
a) Phenylessigsäurederivate der Formel Ia) Phenylacetic acid derivatives of the formula I.
:D ,: D,
in der die Substituenten und der Index die folgende Bedeutung haben:in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3 oder CHCH3 ;X STILL 3 , CHOCH 3 or CHCH 3 ;
Y Sauerstoff oder NR;Y is oxygen or NR;
R^R unabhängig voneinander Wasserstoff oder C1-C4-Alkyl,■ R ^ R independently of one another hydrogen or C 1 -C 4 alkyl, ■
R2 Cyano, Nitro, Trifluormethyl, Halogen, Cι-C-Alkyl oder Cι-C4-Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, -CC alkyl or -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-Halogenalkyl oder C3-C6-Cycloalkyl;R 3 is hydrogen, cyano, C 4 -alkyl, C 4 haloalkyl or C 3 -C 6 cycloalkyl;
R4,R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-Cι0-Alkenyl, C -Cιo-Alkinyl, Cι-Cι0-Alkylcarbonyl , C2-Cι0-Alkenyl- carbonyl, Cß-Cio-Alkinylcarbonyl oder Cι-Cιrj-Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothio- 2 carbonyi, Halogen, Ci-Cβ-Alkyl, Ci-Cβ-Halogenalkyl, Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, Cι-C6-Alkoxy, Cx-Cδ-Halogenalkoxy, Cι-C6-Alkoxycarbonyl , Cι-C6-Alkyl- thio, Ci-Cδ-Alkylamino, Di-Ci-Cδ-alkylamino, Cι-C6-Alkylaminocarbonyl, Di-Cι-C6-alkylaminocarbonyl,-C-Cιo-alkyl, C 3 -C 6 cycloalkyl, C 2 -Cι 0 -alkenyl, C -Cιo-alkynyl, Cι-Cι 0 -alkylcarbonyl, C 2 -Cι 0 -alkenylcarbonyl, C ß -Cio- Alkynylcarbonyl or -CC-alkyl sulfonyl, these radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothio 2 carbonyi, halogen, Ci-Cβ-alkyl, Ci-Cβ-haloalkyl, -C-C 6 -alkylsulfonyl, Cι-C 6 -alkylsulfoxyl, Cι-C 6 -alkoxy, Cx-C δ -haloalkoxy, Cι-C 6 - alkoxycarbonyl, Cι-C 6 -alkylthio, Ci-Cδ-alkylamino, di-Ci-C δ alkylamino, Cι-C 6 -alkylaminocarbonyl, di-Cι-C 6 alkylaminocarbonyl,
Ci-Cö-Alkylaminothiocarbonyl, Di-Cι-C6-alkylaminothio- carbonyl, C -C6-Alkenyl, C2-C6-Alkenyloxy, C3-C6-Cyclo- alkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Hetero- cyclyloxy, 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, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothio- carbonyi, Halogen, Ci-Cβ-Alkyl, Ci-Cβ-Halogenalkyl,Ci-Cö-alkylaminothiocarbonyl, di-Cι-C6-alkylaminothio-carbonyl, C -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl , Heterocyclicoxy, benzyl, 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, aminocarbonyl, aminothio-carbonyi, halogen, Ci-Cβ-alkyl, Ci-Cβ-haloalkyl,
Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, C3-C6-Cyclo- alkyl, Cι-C6-Alkoxy, Cι-C6-Halogenalkoxy, Ci-Cg-Alkyl - oxycarbonyl, Ci-Cβ-Alkylthio, Ci-Cg-Alkylamino, Di-C -Cβ-Alkylamino, Ci-Cß-Alkylaminocarbonyl , Di-Ci-Cö-Alkylaminocarbonyl, Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cδ-Alkylaminothiocarbonyl, C2-C6- Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C(=NOR7)-An-R8;Cι-C 6 alkylsulfonyl, Cι-C 6 alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Cι-C 6 -alkoxy, C 6 haloalkoxy, Ci-Cg-alkyl - oxycarbonyl, Ci-Cβ- Alkylthio, Ci-Cg-alkylamino, di-C -Cβ-alkylamino, Ci-C ß -alkylaminocarbonyl, di-Ci-C ö -alkylaminocarbonyl, Ci-Cg-alkylaminothio-carbonyl, di-Ci-C δ -alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl, Arylsulfonyl , Hetaryl, Hetaryl - carbonyi 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,Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetaryl-carbonyi or hetarylsulfonyl, 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,
Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cβ-Alkyl, Cι-C6-Halogenalkyl, Ci-Cδ-Alkylcarbonyl, Cι-C6-Alkyl- sulfonyl, Ci-Cβ-Alkylsulfoxyl, C3-C6-Cycloalkyl, Ci-Cß-Alkoxy, Ci-Cδ-Halogenalkoxy, Ci-Cδ-Alkyloxy- carbonyi, Cι-C6-Alkylthio, Cι-C6-Alkylamino, Di-Cι-C6-Aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cβ-alkyl, -C-C 6 -haloalkyl, Ci-C δ -alkylcarbonyl, Cι-C 6 -alkyl-sulfonyl, Ci-Cβ-alkylsulfoxyl, C 3 -C 6 cycloalkyl, Ci -C ß -alkoxy, Ci-C δ -haloalkoxy, Ci-Cδ-alkyloxy-carbonyi, Cι-C 6 -alkylthio, Cι-C 6 -alkylamino, di-Cι-C 6 -
Alkylamino, Ci-Cδ-Alkylaminocarbonyl, Di-Cι-C6-Alkyl- aminocarbonyl , Ci-Cö-Alkylaminothiocarbonyl, Di-Ci-Cδ- Alkylaminothiocarbonyl, C2-C6-Alkenyl , C2-Ce-Alkenyl- oxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C (=NOR7) -An-R8;Alkylamino, Ci-C δ- alkylaminocarbonyl, Di-Cι-C 6 alkyl aminocarbonyl, Ci-Cö-alkylaminothiocarbonyl, Di-Ci-C δ - alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C e alkenyl - oxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 7 ) -A n -R 8 ;
Wasserstoff,Hydrogen,
Ci-Cβ-Alkyl, C-C6-Alkenyl, C-C6-Alkinyl, wobei die Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, 3Ci-Cβ-alkyl, CC 6 -alkenyl, CC 6 -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, 3
Hydroxy, Mercapto,Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-Alkyl - sulfonyl, Cι-C6-Alkylsulfoxyl, Ci-Cg-Alkoxy, Cι~C6-Hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothio-carbonyl, di-Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-alkyl - sulfonyl, -CC 6 alkyl sulfoxyl, Ci-Cg-alkoxy, -C ~ C 6 -
Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-alkylamino, C2-C6-Alkenyloxy, C3-Cg-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-C1-C4-alkoxy, Arylthio, Aryl-Cι-C4-alkylthio, Hetaryl, Hetaryloxy,Haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, C 2 -C 6 -alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -C6-cycloalkyloxy, Heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, arylthio, aryl-Cι-C 4 -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,Hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC 4 -alkyl thio, 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,
Aminocarbonyl, Aminothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Cx-Cg-Alkylsulfonyl, Ci-Cg-Alkyl - sulfoxyl, C3Cg-Cycloalkyl, Cχ-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Cι~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-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetaryl - thio und C (=NOR7) -An-R8;Aminocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Cx-Cg-alkylsulfonyl, Ci-Cg-alkyl - sulfoxyl, C3Cg-cycloalkyl, Cχ-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg- Alkoxycarbonyl, Ci-Cg-alkylthio, Cι ~ Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkyl - aminothiocarbonyl, di-Ci Cg-alkylaminothiocarbonyl, C 2 -Cg alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetaryl-thio and C (= NOR 7 ) -A n -R 8 ;
C3-Cg-Cycloalkyl, C3 -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,C 3 -Cg cycloalkyl, C 3 -Cg 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, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkyl- sulfoxyl, C3-Cg-Cycloalkyl, Ci-Cg-Alkoxy, C -Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Cι~Cg-Nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci -Cg-alkoxy, C -Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Cι ~ 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;Alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkyl - aminothiocarbonyl, 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 Ci-Cg-Alkyl trägt; 4 n 0 oder 1 bedeutet;A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Cg-alkyl; 4 n represents 0 or 1;
R7 Wasserstoff oder Ci-Cg-Alkyl bedeutet undR 7 is 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
b) mindestens einem Fungizid ausgewählt aus Fungiziden der For meln II bis VIIb) at least one fungicide selected from fungicides of the formulas II to VII
Cl— ^ CH2 .Cl— ^ CH 2 .
NNCONH ^ : ID N NCONH ^: ID
OCH(CH- 3)'2OCH (CH- 3) '2
CONH ( ff \ \) ( ιτι>CONH (ff \ \) (ιτι >
( IV)(IV)
-OCF, (v) -OCF, (v)
NN
H3C H 3 C
(VI )(VI)
CONHChKChL 3)^2CONHChKChL 3) ^ 2
(VII)(VII)
Der vorliegenden Erfindung lag die Aufgabe zugrunde, fungizide Mischungen zur Verfügung zu stellen, die eine gute, über die Wirksamkeit der Mischungskomponenten allein hinausgehende fungizide 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 VII sind ebenfalls bekannt und in der Literatur beschrieben. Darüber hinaus sind sie unter den nachfolgend in Klammern genannten Handelsnamen kommerziell erhältlich: 6The fungicides of the formulas II to VII are also known and are described in the literature. They are also commercially available under the trade names below in brackets: 6
II: DE-A 27 32 257, Common name: Pencycuron (Handelsname: Monce- ren , Fa. Bayer);II: DE-A 27 32 257, common name: Pencycuron (trade name: Moncer, from Bayer);
III :JP 01/104,514, Common name: Flutolanil (Handelsname: Mon- cut®, Fa. Nihon Noyaku) ;III: JP 01 / 104.514, common name: Flutolanil (trade name: Mon- cut ®, Nihon Noyaku.);
IV: US 3,937,840, Common name: Mepronil (Handelsname: Basitac®, Fa. Kumiai) ;IV: US 3,937,840, common name: mepronil (trade name: Basitac ®, from Kumiai.);
V: Common name: Thifluzamid (Handelsname: Greatam , Fa. Monsanto) ;V: Common name: Thifluzamid (trade name: Greatam, Monsanto);
VI: GB-A 1,312,536, US 3,755,350; Common name: IprodioneVI: GB-A 1,312,536, US 3,755,350; Common name: Iprodione
(Handelsname: Rovral®, Fa. Rhone-Poulenc) ;(Trade name: Rovral ®, from Rhone-Poulenc.);
VII: AG Chem New Compound Review, Vol. 15 (1997), 50; Common name: Furametpyr (Handelsname: Limber®, Fa. Sumitomo) .VII: AG Chem New Compound Review, Vol. 15 (1997), 50; Common name: furametpyr (trade name: Limber ®, Sumitomo.).
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 all- gemeinen 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 are obtained 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 influence 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 (Konfigu- ration 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: 7In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups: 7
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-Dimethylethyl, 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-Dimethylbutyl, 1, 3-Dimethylbutyl, 2 , 2-Dimethylbutyl,Alkyl: straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-Cg-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, 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, 1, 1, 2-Trimethylpropyl, 1, 2 , 2-Trimethylpropyl, 1-Ethyl-l-methyl - propyl und 1- Ethyl-2-methylpropyl;2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl and 1-ethyl- 2-methylpropyl;
Halocrenalkyl ; 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 Chlor - methyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluor- methyl, Trif luormethyl, Chlorfluormethyl, Dichlorfluormethyl,Halocrenalkyl; straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, Trif luormethyl, chlorofluoromethyl, dichlorofluoromethyl,
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 ;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;
Cvcloalkyl : monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoff - ringgliedern, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl;Cvcloalkyl: 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,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,
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, 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- 8 butenyl, 1, 2-Dimethyl-l-butenyl, 1, 2-Dime hyl-2-butenyl,4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 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-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- 8 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,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-l-butenyl, 2 , 3-Dimethyl-2-butenyl , 2 , 3-Dimethyl-3- butenyl, 3, 3-Dimethyl-l-butenyl, 3 , 3-Dimethyl-2-butenyl,2, 3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3-dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3, 3-dimethyl-2-butenyl,
1-Ethyl-l-butenyl, l-Ethyl-2-butenyl, l-Ethyl-3-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,2-ethyl-1-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;1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
Alkinyl ; geradkettige oder verzweigte Alkinylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, z.B. C2-C6-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, for example C 2 -C 6 -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. Heterocvclyloxy, Heterocvclylthio und Hetero- cvclylamino; 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- furanyl, 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 heterocvclyloxy, heterocvclylthio and heterocvclylamino; 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 one Sulfur atom or (heterocyclylamino) are attached to the skeleton via a nitrogen atom, such as, for example 2-tetrahydrofuran, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazole-dinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 3-isothiazolidinyl, 5-isothiazolidinyl, 3 -pyrazolidinyl,
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, l,2,4-Thiadiazolidin-5-yl, 1, 2 , 4-Triazolidin-3-yl,4 -pyrazolidinyl, 5 -pyrazolidinyl, 2 -oxazolidinyl, 4 -oxazolidinyl, 5-oxazolidinyl, 2 -thiazolidinyl, 4 -thiazolidinyl, 5 -thiazolidinyl, 2 -imidazolidinyl, 4 -imidazolidinyl, 1,2,4-oxadiazolidine 3 -yl, 1,2,4 -oxadiazolidin-5 -yl, 1,2,4-thiadiazolidin-3-yl, l, 2,4-thiadiazolidin-5-yl, 1, 2, 4-triazolidin-3- yl,
1, 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- für- 4 -yl , 2 , 3 -Dihydro- f r- 5 -yl , 2,5 -Dihydro-für - 2 -yl , 2, 5 -Dihydro- für- 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, 91, 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- for- 4 -yl, 2, 3 -Dihydro- for r- 5 -yl, 2,5 -Dihydro-für - 2 -yl, 2, 5 -Dihydro - for- 3-yl, 2, 3 -dihydrothien-2 -yl, 2,3-dihydrothien-3-yl, 2, 3 -dihydrothien- 4 -yl, 2, 3 -dihydrothien- 5 -yl, 2nd , 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 , 9
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 -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 -Dihydroisopyrazol -5 -yl, 2, 3 -Dihydrooxazol -3-yl, 2, 3 -Dihydrooxazol- 4-yl, 2, 3 -Dihydro - 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,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 -dihydroisoxazol- 5-yl, 4, 5 -dihydroisoxazole -3 -yl, 4, 5 -dihydroisoxazole -4 -yl, 4, 5 -dihydroisoxazole -5 -yl, 2, 5-dihydroisothiazol-3- yl, 2, 5-dihydroisothiazole - 4 -yl, 2, 5 -dihydroisothiazole -5-yl, 2, 3 -dihydroisopyrazole -3-yl, 2, 3 -dihydroisopyrazole- 4 -yl, 2, 3 -dihydroisopyrazole -5- yl, 4, 5 -dihydroisopyrazole -3 -yl, 4, 5 -dihydroisopyrazole -4 -yl, 4, 5 -dihydroisopyrazole -5-yl, 2, 5 -dihydroisopyrazole -3 -yl, 2, 5 -dihydroisopyrazole- 4 - yl, 2, 5 -dihydroisopyrazole -5 -yl, 2, 3 -dihydrooxazol -3-yl, 2, 3 -dihydrooxazol- 4-yl, 2, 3 -dihydro - oxazol-5-yl, 4, 5 -dihydrooxazole - 3 -yl, 4, 5 -dihydrooxazole -4 -yl, 4, 5 -dihydrooxazol -5-yl, 2, 5 -dihydrooxazole -3 -yl, 2, 5 -dihydro - oxazol-4-yl, 2, 5 - Dihydrooxazole -5 -yl, 2, 3 -Dihydrothiazol-2 -yl, 2, 3 -Dihydrothiazol -4 -yl, 2, 3 -Dihydrothiazol-5-yl, 4,5-Dihydro- th iazol-2-yl, 4,5-dihydrothiazole -4 -yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazole -4 -yl, 2,5- Dihydro-thiazol-5-yl, 2,3-dihydroimidazole -2-yl, 2,3-dihydroimidazole -4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazole -2-yl, 4, 5 -dihydroimidazole -4 -yl, 4, 5 -dihydroimidazole -5 -yl, 2, 5 -dihydroimidazol-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-tetrahydro-pyrimidinyl, 2-tetrahydropyraz Tetrahydrotriazin-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 (-S02-) an das Gerüst gebunden sind, z.B. Phenyl, Naphthyl und Phenanthrenyl bzw. Phenyloxy, Naphthyloxy und Phenanthrenyl - oxy und die entsprechenden Carbonyi- 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 bonded to the skeleton via a sulfonyl group (-S0 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyl-oxy 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, additionally 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 10May contain sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom 10
(-S-), (Hetarylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Hetarylsulfonyl) über eine Sulfonylgruppe (-S0 -) an das Gerüst gebunden sind, z.B.(-S-), (hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group (-S0 -) are attached to the skeleton, 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, 4-Pyrazolyl, 5-Pyrazolyl, 2-Imidazolyl, 4-Imidazolyl, l,2,4-Triazol-3-yl und 1, 3 , 4-Triazol-2-yl;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 and 1, 3, 4-triazol-2- yl;
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 Stickstoffatome 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-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 and may contain 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, 2-0xazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-Imidazolyl, 4-Imidazolyl, 1, 2, 4-Oxadiazol- 3-yl, 1, 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;5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5- Thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazol-3-yl, 1, 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;
- benzokondensiertes 5-αliedriσes 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-condensed 5-αliedriσes heteroaryl, containing one to three nitrogen atoms or a nitrogen atom and / or an 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 a sulfur or oxygen atom or an oxygen - Or can contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can 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 Heteroaryl - gruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome bzw. ein bis drei Stickstoffatome als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlen- 115-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or 5-membered heteroaryl, bonded via nitrogen, 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 can contain as ring links, and in which two adjacent coal 11
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;Material ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;
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,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, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,
2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 2-Pyrazinyl, 1, 3, 5-Triazin-2-yl, 1, 2, 4-Triazin-3-yl und 1,2,4, 5-Tetrazin-3-yl;2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl, 1, 2, 4-triazin-3-yl and 1,2,4, 5-tetrazine 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-, Carbonyi- oder Sulfonyl - gruppen.or the corresponding oxy, thio, carbonyi 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 Ausdruck bringen, daß in den derart charakterisierten Gruppen die Wasserstoffatome zum Teil oder vollständig durch gleiche oder verschiedene Halogenatome wie vorstehend genannt ersetzt sein können.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. 12In addition, compounds I are preferred in which R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 . 12
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 Cyclo - propyl steht.Compounds I in which R 3 is cyclopropyl are furthermore preferred.
Des weiteren werden Verbindungen I bevorzugt, in denen R3 für CF3 steht.Furthermore, compounds I are preferred in which R 3 is CF 3 .
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 lso-Propyl steht.In addition, compounds I are preferred in which R 5 is isopropyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Cyclopropyl 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. 13Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl. 13
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, Aminocarbonyl, Aminothiocarbonyl, Halogen, C1-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy, Cι-C -Alkylamino, Di-Cι-C4- Alkylamino, Cι-C4-Alkylsulfonyl, Cι-C4-Alkoxycarbonyl, Cι~C -Alkyl - aminocarbonyl oder Di-Cι-C4-Alkylaminocarbonyl .In 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, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 alkyl, Cι- C 4 -haloalkyl, -C-C 4 -alkoxy, -C-C 4 -haloalkoxy, Cι-C -alkylamino, di-Cι-C 4 - alkylamino, Cι-C 4 -alkylsulfonyl, Cι-C 4 -alkoxycarbonyl, Cι ~ C alkyl - aminocarbonyl or di -CC 4 alkylaminocarbonyl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Wasserstoff, Ci-Cg-Alkyl, C2-C6-Alkenyl, C2 -Cg -Alkinyl , 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 -C 6 alkenyl, C 2 -Cg alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für Ci-Cg-Alkyl steht.Furthermore, compounds I are preferred in which R 4 is Ci-Cg-alkyl.
Weitere bevorzugte Verbindungen I sind der WO 97/15,552 zu entnehmen.Further preferred compounds I can be found in WO 97 / 15,552.
Die in den erfindungsgemäßen Mischungen enthaltenen Verbindungen I zeichnen sich durch eine hervorragende Wirkung gegen ein brei- tes 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 notable for 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, Gemüsepflanzen (z.B. Gurken, Bohnen, Tomaten, Kartoffeln und Kürbisgewächse), Gerste, Gras, Hafer, Bananen, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, 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 (e.g. cucumber, beans, tomatoes, potatoes and squashes), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye, soy , Wine, wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuk- kerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminthospori- um-Arten an Getreide und Reis, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudo- cercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis und Rasen, Phytophthora infestans an Kartoffeln 14 und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Ar- ten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosphaerella-Arten in Bananen sowie Fusarium- und Verticillium- Arten.They are particularly suitable for combating the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on squash plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizo species Rice and lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals and rice, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries, vegetables, ornamental plants and vines , Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice and lawn, Phytophthora infestans on potatoes 14 and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species in vegetables and fruit, Mycosphaerella species in bananas and Fusarium and Verticillium species.
Die Verbindungen II bis VII sind als Fungizide kommerziell erhältlich.The compounds II to VII are commercially available as fungicides.
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I und II bis VII 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 VII, 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 bis VII 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 eingesetzt werden.The mixtures of the compounds I and at least one compound II to VII 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 leaf 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 Kürbisgewächse), Gerste, Gras, Hafer, Bananen, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zucker- röhr sowie an einer Vielzahl von Samen.They are particularly important for combating a large number of fungi on various crops such as cotton, vegetables (e.g. cucumbers, beans, tomatoes, potatoes and squashes), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye, soy , Wine, wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe graminis (echter Mehltau) anThey are particularly suitable for combating the following phytopathogenic fungi: Erysiphe graminis (powdery mildew)
Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuk- kerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminthospori- um-Arten an Getreide und Reis, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudo- cercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis und Rasen, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Ar- ten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, 15Cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawn, Ustilago species on cereals and sugar cane (Venturia inae ) on apples, Helminthosporium species on cereals and rice, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on Rice and lawn, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species on vegetables and fruits, 15
Mycosphaerella-Arten in Bananen sowie Fusarium- und Verticillium- Arten.Mycosphaerella species in bananas as well as Fusarium and Verticillium species.
Besonders bevorzugt sind die erfindungsgemäßen Mischungen zur Be- kämpfung von Pyricularia oryzae einsetzbar.The mixtures according to the invention can be used particularly preferably for controlling Pyricularia oryzae.
Die Verbindungen I und mindestens eine der Verbindungen II bis VII können gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander aufgebracht werden, wobei die Reihenfolge bei ge- trennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compounds I and at least one of the compounds II to VII can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen, vor allem bei landwirtschaftlichen Kulturflächen, je nach Art des ge- wünschten 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, depending on the type of effect desired /Ha.
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 VII liegen entsprechend bei 0,001 bis 5 kg/ha, vorzugsweise 0,005 bis 2 kg/ha, insbesondere 0,01 bis 1,0 kg/ha.The application rates for the compounds II to VII 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 VII durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Aufla - fen 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 VII 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 Raising the plants.
Die erfindungsgemäßen fungiziden synergistischen Mischungen können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßri- gen, 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. 16The 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. 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. 16
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 Verdünnungs- mittel auch andere organische Lösungsmittel als Hilfslösungsmittel verwendet werden können. Als Hilfsstoffe kommen dafür im wesentlichen in Betracht: Lösungsmittel wie Aromaten (z.B. Xylol) , chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdöl - fraktionen) , Alkohole (z.B. Methanol, Butanol) , Ketone (z.B. Cy- clohexanon), Amine (z.B. Ethanolamin, Dimethylformamid) und Wasser; Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate) ; Emulgiermittel wie nichtio- nogene und anionische Emulgatoren (z.B. Polyoxyethylen-Fettalko- hol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Ligninsulfitablaugen und Methylcellulose.The formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where in the case of water as diluent other organic solvents can also be used as auxiliary solvents. The following are essentially considered as auxiliaries: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines ( eg ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolethern, Kondensationsprodukte von sulfoniertem Naphthalin und seinen Derivaten mit Form- aldehyd, Kondensationsprodukte des Naphthalins bzw. derThe alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic 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 - aldehyde, condensation products of naphthalene or
Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol- oder Tributylphenylpolyglycolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkohol - ethylenoxid- Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- alkylether oder Polyoxypropylen, Laurylalkoholpolyglycoletherace- tat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht .Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol - ethylene oxide condensates, ethoxylated alkoxylated alcohol, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxylacetyl ether, polyoxyethylene oxyethyl ether -Sulfite waste or methyl cellulose into consideration.
Pulver Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der Verbindungen I und mindestens einer der Verbindungen II bis VII oder der Mischung aus den Verbindungen I und mindestens einer Verbindung II bis VII mit einem festen Träger - Stoff hergestellt werden.Powder broadcasting and dusting agents can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to VII or the mixture of the compounds I and at least one compound II to VII with a solid carrier substance.
Granulate (z.B. Umhüllungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt.Granules (e.g. coating, impregnation or homogeneous granules) are usually produced by binding the active ingredient or ingredients to a solid carrier.
Als Füllstoffe bzw. feste Trägerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolo- 17 mit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolo- 17 mit, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal 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 VII bzw. der Mischung aus den Verbindungen I und mindestens einer der Verbindungen II bis VII. Die Wirkstoffe werden dabei in 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 VII or the mixture of the compounds I and at least one of the compounds II to VII. 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, Böden, Flächen, Materialien oder Räume mit einer fungizid wirksamen Menge der Mischung, bzw. der Verbindungen I und mindestens einer der Verbindungen II bis VII bei getrennter Ausbringung, behandelt.The corresponding formulations are used in such a way that the harmful fungi, their habitat or the plants, seeds, soils, surfaces, 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 VII treated separately.
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 enthalten, sind:Examples of such preparations that contain the active ingredients are:
I. eine Lösung 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 Ethylenoxid an 1 Mol Ölsäure-N-monoethanola- mid, 5 Gew. -Teilen Calciumsalz der Dodecylbenzolsulfon- säure, 5 Gew. -Teilen des Anlagerungsproduktes von 40 MolII. 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 of dodecylbenzenesulfonic acid, 5 parts by weight of the adduct of 40 mol
Ethylenoxid an 1 Mol Ricinusol; durch feines Verteilen der Lösung in Wasser erhält man eine Dispersion;Ethylene oxide on 1 mole of ricinusol; 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 Iso- butanol, 20 Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusol;III. 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 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of ricinusol;
IV. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 25 Gew. -Teilen Cyclohexanol, 65 Gew. -Teilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusol; i 1 e , P d 1 , , CD d ■ 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 with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole Castor oil; i 1 e, P d 1 ,, CD d ■
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> x> x
> P CQ P -H -u ε P PQ tn 5 in σ m σ m O tn σ in CO ro ^J* > P CQ P -H -u ε P PQ tn 5 in σ m σ m O tn σ in CO ro ^ J *
1919
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)] ermittelt und mit den beobachteten Wirkungsgraden verglichen.The expected efficacies of the active ingredient mixtures were calculated using the Colby formula [R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficiencies.
Colby Formel: E = x + y - x-y/100Colby formula: E = x + y - x-y / 100
E zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b x 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 bE expected efficiency, expressed in% of the untreated control, when using the mixture of active ingredients A and B in concentrations a and bx 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
Anwendungsbeispiele - Wirksamkeit gegen Pyricularia oryzae (pro- tektiv)Examples of use - effectiveness 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 ermittelt.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.
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 an- tagonistic 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 ingredients 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: CHThe following compound I 'was used as component a): CH
H3C. O^ " ^ NH 3 C. O ^ " ^ N
: i ' O-Ch: i ' O-Ch
CH. • N 3 CH. • N 3
H3C H 3 C
Die Ergebnisse der Versuche sind den nachstehenden Tabellen 1 und 2 zu entnehmen:The results of the tests are shown in Tables 1 and 2 below:
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 VII 2,0 0 0,5 03V connection VII 2.0 0 0.5 0
Tabelle 2:Table 2:
Bsp. erfindungsgemäße Mischung beobachteter berechneter (Konz. in ppm) Wirkungsgrad Wirkungsgrad *>For example, the mixture according to the invention of calculated calculated (conc. In ppm) efficiency efficiency *>
4 2 ppm I' + 2 ppm VII 35 % 20 %4 2 ppm I '+ 2 ppm VII 35% 20%
5 0,5 ppm I' + 0,5 ppm VII 20 % 0 % 5 0.5 ppm I '+ 0.5 ppm VII 20% 0%
*) 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

2121
Patentansprücheclaims
1. Fungizide Mischungen, enthaltend als aktive Komponenten1. Fungicidal mixtures containing as active components
a) Phenylessigsäurederivate der Formel Ia) Phenylacetic acid derivatives of the formula I.
( i : Frγ> ^ •:x(i: Fr γ > ^ • : x
00
'R 0 ' R 0
in der die Substituenten und der Index die folgende Bedeutung haben:in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3 oder CHCH3;X STILL 3 , CHOCH 3 or CHCH 3 ;
Y Sauerstoff oder NR;Y is oxygen or NR;
R^R unabhängig voneinander Wasserstoff oder Cι-C4-Alkyl;R ^ R independently of one another hydrogen or -CC 4 alkyl;
R2 Cyano, Nitro, Trifluormethyl, Halogen, Cι-C4-Alkyl oder Cι-C4-Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, C 1 -C 4 alkyl or C 1 -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-Halogenalkyl oder C3-C6-Cycloalkyl;R 3 is hydrogen, cyano, C 4 -alkyl, C 4 haloalkyl or C 3 -C 6 cycloalkyl;
R4,R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-Cι0-Alkenyl, c 2~Cιo-Alkinyl, Cι-Cιo-Alkylcarbonyl, C2-Cιrj-Alkenyl- carbonyl, C3-Cιo-Alkinylcarbonyl oder Cι-Cιo~Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgen¬ den Gruppen tragen können: Cyano, Nitro, Hydroxy, 22Cι-Cιo-alkyl, C 3 -C 6 cycloalkyl, C 2 -Cι 0 -alkenyl, c 2 ~ -Cιo-alkynyl, Cι-Cιo-alkylcarbonyl, C 2 -Cιrj-alkenylcarbonyl, C 3 -Cιo-alkynylcarbonyl or Cι-Cιo ~ alkyl sulfonyl, these radicals to be partially or fully halogenated or one to three of the following groups ¬ can carry: cyano, nitro, hydroxy, 22
Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkyl - thio, Ci-Cg-Alkylamino, Di-Cι-C6-alkylamino,Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Cι-C 6 -alkylsulfonyl, Cι-C 6 -alkylsulfoxyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkyl - thio, Ci-Cg-alkylamino, di-Cι-C 6 alkylamino,
Cι-C6-Alkylaminocarbonyl , Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl, Di-Ci-Cg-alkylaminothio- carbonyl, C -C6-Alkenyl, C -Cg-Alkenyloxy, C3-Cg-Cyclo- alkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Hetero- cyclyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio,C 1 -C 6 alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothio-carbonyl, C -C 6 -alkenyl, C -Cg-alkenyloxy, C 3 -Cg-cyclo alkyl, C 3 -C 6 -cycloalkyloxy, heterocyclyl, heterocyclicoxy, 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, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl, C3-C6-Cyclo- alkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyl - oxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-Alkylamino, C -Cg-Alkylaminocarbonyl ,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, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl , Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyl - oxycarbonyl, Ci -Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, C -Cg-alkylaminocarbonyl,
Di-Ci-Cg-Alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cg-Alkylaminothiocarbonyl, C -Cg- Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C(=NOR7) -An-R8;Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, Di-Ci-Cg-alkylaminothiocarbonyl, C -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy , Hetarylthio or C (= NOR 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl, Arylsulfonyl, Hetaryl, Hetaryl - carbonyi oder Hetarylsulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können:Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetaryl-carbonyi or hetarylsulfonyl, 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, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylcarbonyl, Ci-Cg-Alkyl - sulfonyl, Ci-Cg-Alkylsulfoxyl , C3-Cg-Cycloalkyl , Cχ-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxy- carbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg- Alkylamino, Ci-Cg-Alkylaminocarbonyl, Di-C -Cg-Alkyl- aminocarbonyl, Ci-Cg-Alkylaminothiocarbonyl, Di-Cχ-Cg- Alkylaminothiocarbonyl, C2-Cg-Alkenyl , C2-Cg-Alkenyl- oxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl,Cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylcarbonyl, Ci-Cg-alkyl-sulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Cχ-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg -Alkylaminocarbonyl, Di-C -Cg-alkyl aminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, Di-Cχ-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy Hetaryl
Hetaryloxy oder C (=NOR7) -An-R8;Hetaryloxy or C (= NOR 7 ) -A n -R 8 ;
Wasserstoff,Hydrogen,
Ci-Cg-Alkyl, C2-Cg-Alkenyl , C2-C6-Alkinyl, wobei dieCi-Cg-alkyl, C 2 -Cg alkenyl, C 2 -C 6 alkynyl, the
Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis 23 drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto,Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyi, Di-Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-Alkyl - sulfonyl, Ci-Cg-Alkylsulfoxyl, Ci-Cg-Alkoxy, Cι~C6- Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkyl hio, Ci-Cg-Alkylamino, Di-Ci-Cö-alkylamino, C2-Cg-Alkenyloxy, C3-Cg-Cycloalkyl, C3-Cg-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cι-C4-alkoxy,Hydrocarbon radicals of these groups can be partially or completely halogenated or one to 23 can carry three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothio-carbonyi, di- Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-alkyl-sulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Cι ~ C 6 - haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkyl hio, Ci-Cg- Alkylamino, di-Ci-Cö-alkylamino, C 2 -Cg-alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -Cg-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-Cι-C 4 -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:Arylthio, aryl -CC 4 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC 4 -alkyl-thio, 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, Aminocarbonyl, Aminothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cö-Alkylsulfonyl, Ci-Cg-Alkyl - sulfoxyl, C3Cg-Cycloalkyl, Ci-Cg-Alkoxy, Cι~Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-C ö alkylsulfonyl, Ci-Cg-alkyl-sulfoxyl, C 3 Cg-cycloalkyl, Ci -Cg-alkoxy, Cι ~ Cg-haloalkoxy, 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, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C (=N0R7)-An-R8;Alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkyl - aminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NO R 7 ) -A n -R 8 ;
C3-C -Cycloalkyl, C3-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, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkyl- sulfoxyl, C3-Cg-Cycloalkyl , Cχ-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Cι~Cg- Alkylamino, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-Alkyl - aminothiocarbonyl , Di-C-Cg-alkylaminothiocarbonyl , C2-Cg-Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy,C 3 -C cycloalkyl, C 3 -Cg 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, hydroxyl, mercapto, amino, Carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Cχ-Cg-alkoxy, Ci-Cg -Halogenalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Cι ~ Cg- alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkyl - aminothiocarbonyl, di-C-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy,
Aryl, Aryloxy, Hetaryl und Hetaryloxy;Aryl, aryloxy, hetaryl and hetaryloxy;
wobei 24in which 24
A für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cg-Alkyl trägt;A 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 Wasserstoff oder Ci-Cg-Alkyl bedeutet undR 7 is 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
b) mindestens eine Verbindung der Formeln II bis VIIb) at least one compound of the formulas II to VII
Cl / (/ ^ x) CH2 .. ^Cl / (/ ^ x ) CH 2 .. ^
NCONH {' N> ( ii ;NCONH {' N >(ii;
OCH(CH3 V)2.OCH (CH 3 V) 2.
COMNMH / (// % \) (m) COMNMH / (/ / % \) ( m )
( IV)(IV)
25 25th
CONH OCF, (V)CONH OCF, (V)
N' ^ wN ' ^ w
H3C H 3 C
(VI )(VI)
CONHCH(CI-L 3)/2CONHCH (CI-L 3) / 2
(VI I )(VI I)
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 VII in einem festen oder flüssigen Träger enthält.A 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 VII in a solid or liquid carrier.
3. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen,3. A method for combating harmful fungi, characterized in that the fungi, their habitat or the materials, plants, seeds to be protected against fungal attack,
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 VII gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander erfolgen kann. 26Soils, surfaces or rooms treated with a fungicidal mixture according to any one of claims 1 to 2, it being possible for compound I and at least one of compounds II to VII to be used simultaneously, together or separately, or in succession. 26
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 VII 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 VII according to Claim 1 treated.
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Publication number Priority date Publication date Assignee Title
JP2814678B2 (en) * 1990-03-29 1998-10-27 住友化学工業株式会社 Agricultural and horticultural sterilizing composition
EP0741970B1 (en) * 1993-12-02 2002-04-24 Sumitomo Chemical Company Limited Bactericidal composition
JP3470399B2 (en) * 1994-07-14 2003-11-25 住友化学工業株式会社 Fungicide composition
ATE172360T1 (en) * 1994-07-21 1998-11-15 Basf Ag METHOD FOR CONTROLLING HARMFUL FUNGI
JP3558405B2 (en) * 1995-04-20 2004-08-25 三井化学株式会社 Insecticidal fungicidal composition
TW401275B (en) * 1995-09-25 2000-08-11 Basf Ag Compositions and methods of controlling harmful fungi
FR2739529B1 (en) * 1995-10-05 1997-10-31 Rhone Poulenc Agrochimie FUNGICIDAL COMPOSITION COMPRISING A STROBILURIN-LIKE COMPOUND
DE19539324A1 (en) * 1995-10-23 1997-04-24 Basf Ag Phenylacetic acid derivatives, processes and intermediates for their preparation and compositions containing them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9948365A1 *

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CA2323661A1 (en) 1999-09-30
IL138167A0 (en) 2001-10-31
TW565431B (en) 2003-12-11
ID27443A (en) 2001-04-12
CN1294491A (en) 2001-05-09
AU3331599A (en) 1999-10-18
KR100557364B1 (en) 2006-03-10
JP2002507550A (en) 2002-03-12
WO1999048365A1 (en) 1999-09-30
BR9908996A (en) 2000-12-12
KR20010042147A (en) 2001-05-25
CO5050292A1 (en) 2001-06-27

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