WO1999048367A1 - Fungicide mixtures based on triple oxime ether derivatives and other strobilurins - Google Patents

Fungicide mixtures based on triple oxime ether derivatives and other strobilurins Download PDF

Info

Publication number
WO1999048367A1
WO1999048367A1 PCT/EP1999/001909 EP9901909W WO9948367A1 WO 1999048367 A1 WO1999048367 A1 WO 1999048367A1 EP 9901909 W EP9901909 W EP 9901909W WO 9948367 A1 WO9948367 A1 WO 9948367A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
aryl
alkoxy
hetaryl
cycloalkyl
Prior art date
Application number
PCT/EP1999/001909
Other languages
German (de)
French (fr)
Inventor
Klaus Schelberger
Thomas Grote
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to JP2000537433A priority Critical patent/JP2002507552A/en
Priority to CA002323598A priority patent/CA2323598A1/en
Priority to AU34168/99A priority patent/AU3416899A/en
Priority to EP99915684A priority patent/EP1065930A1/en
Priority to BR9909001-5A priority patent/BR9909001A/en
Priority to IL13816899A priority patent/IL138168A0/en
Publication of WO1999048367A1 publication Critical patent/WO1999048367A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • 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
    • A01N25/30—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 characterised by the surfactants

Definitions

  • the present invention relates to fungicidal mixtures for combating harmful fungi which
  • R jR independently of one another hydrogen and -CC 4 alkyl
  • n 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
  • R 3 is hydrogen, cyano, -CC alkyl, -C-haloalkyl, C 3 -C 5 cycloalkyl;
  • R 4 , R 6 are independently hydrogen
  • 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, ammo, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg -Alkyl, C] .- Cg-haloalkyl, -C-C 6 alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C -Cg-cycloalkyl, Cx-Cg-alkoxy, C ⁇ -C 6 -haloalkoxy, Ci-Cg-alkyl oxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylammo, D 1 -C 8 -Cg-alkylammo, C 1 -C 6 -alkylammocarbony
  • D ⁇ -C ⁇ -Cg-alkylammocarbonyl, C ⁇ -Cg-alkylammoth ⁇ o- carbonyl, di-Ci-Cg-alkylmothiocarbonyl, 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 ;
  • Cyano Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, C ⁇ -C 6 -Halogenalkyl, C ⁇ -C 6 -Alkylcarbonyl, Ci-Cg-Alkyl- sulfonyl, Ci-Cg- Alkylsulfoxyl, C -C 6 cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxy-carbonyl, C ⁇ -Cg-alkylthio, Ci-Cg-alkylammo, D ⁇ -C ⁇ -Cg-alkylammo, Ci -Cg-alkylammocarbonyl, D ⁇ -C ⁇ -Cg-alkyl - ammocarbonyl, Ci-Cg-alkylammothiocarbonyl, D ⁇ -C ⁇ -C
  • Ci-Cg-Alkyl C 2 -Cg-Alkenyl, C 2 -Cg-Alkmyl, whereby the
  • Hydrocarbon radicals of these groups can be partially or completely halogenated or one to 3 can carry three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothio-carbonyl, di- Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, C ⁇ -Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, Di-Ci-Cg-alkylamino, C 2 -Cg-alkenyloxy, C -Cg-cycl
  • Cyano Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Haloalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl, C 3 Cg-Cycloalkyl, Ci-Cg- Alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-
  • Alkyla ino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylamino-thiocarbonyl, di-C-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C ( NOR 7 ) -A n -R 8 ;
  • n 0 or 1
  • 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, in particular against rice fungal diseases.
  • fungicides of the formulas II to V are also known and described in the literature. In addition, they may be commercially available under the trade names given below in brackets:
  • EP-A 253,313 common name: Kresoxim-methyl (trade name B ⁇ o®, from BASF)
  • EP 398,692 proposed common name: Metommostrobm (development code SSF-126, Shionogi);
  • the compounds I can be produced as E / Z isomer mixtures which, for example, the individual compounds can be separated by crystallization or chromatography in the usual way.
  • 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,
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 6 carbon atoms, wherein the hydrogen atoms constantly may be substituted as mentioned above by halogen atoms in these groups to be partially or fully ⁇ such as C ⁇ -C 2 -haloalkyl such as chloro ⁇ methyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoroethyl,
  • 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; 7
  • Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, e.g. C -Cg alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1- Methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,
  • 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,
  • Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclyllamino three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles, which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or .
  • 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 -), for example Phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyl - oxy and the corresponding carbonyl and sulfonyl radicals;
  • Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl aromatic mono- or polycyclic radicals which in addition to carbon ring members additionally one to four
  • Hetarylsulfonyl are attached to the skeleton via a sulfonyl group (-S0 2 -), for example
  • 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 -Isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyi, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-0xazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 10
  • 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or 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;
  • 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, 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-etrazi-3 -yl;
  • 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,
  • Hetarylammo aromatic mono- or polycyclic radicals which, in addition to carbon members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
  • R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
  • R 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 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
  • R 5 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, ammocarbonyl, ammothiocarbonyl, halogen, C 1 -C 4 alkyl, C 1 -C 4 Haloalkyl, -C-C alkoxy, -C-C -halalkalkoxy, C -C -alkylamino, di-C ⁇ -C - alkylamino, C ⁇ -C -alkylsulfonyl, C ⁇ -C -alkoxycarbonyl, C ⁇ -C -alkyl- aminocarbonyl or di- -CC alkylaminocarbonyl.
  • R 4 represents hydrogen, Ci-Cg-alkyl, C 2 -Cg -alkenyl, C 2 -C -alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
  • R 4 is Ci-Cg-alkyl
  • the compounds I contained in the mixtures according to the invention are distinguished by an outstanding action against a broad spectrum of phytopathogenic fungi, in particular against 13
  • the compounds II to V are commercially available as fungicides.
  • the pure active compounds I and II to V where th further active ingredients against harmful fungi or against other pests, such as Insek ⁇ , arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers.
  • the mixtures of the compounds I and at least one compound II to V 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. Some of them are systemically effective and can therefore also be used as leaf and soil fungicides. 14
  • Botrytis cmera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudo-cercosporella herpot ⁇ choides on wheat and barley, Py ⁇ cularia oryzae on rice and lawn, Phytophthora festans on potatoes and tomatoes, Plasmopara viticoperonosa on vines, Pseudo - in hops and cucumbers, Alternaria species in vegetables and fruits, Mycosp aerella species in bananas and Fusarium and Verticillium species.
  • the mixtures according to the invention can be used particularly preferably for controlling Py ⁇ cularia oryzae.
  • the compounds I and at least one of the compounds II to V 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 control success.
  • the application rates of the inventive mixtures are, in particular in agricultural crop surfaces, depending on the nature of the effect desired ge ⁇ from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 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.
  • the application rates for the compounds II to V are accordingly 0.001 to 5 kg / ha, preferably 0.005 to 2 kg / ha, ms - particularly 0.01 to 1.0 kg / ha. 15
  • 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 V is carried out by spraying or dusting the seeds, the plants or the soil before or after the plants have been sown or before or after the Emergence of plants.
  • the fungicidal synergistic mixtures according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing , Dusting, scattering or pouring.
  • the form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where in the case of water as diluent other organic solvents can also be used as auxiliary solvents.
  • solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine , Dimethylformamide) and water;
  • Carriers such as natural stone powder (e.g.
  • kaolins, clays, talc, chalk) and synthetic stone powder e.g. highly disperse silica, silicates
  • Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • the surface-active substances are the alkali, alkaline earth, and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl and fatty alcohol sulfates, and salts of sulfated hexa -, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or,. the 16
  • 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 sprinklers and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to V or the mixture of the compounds I and at least one compound II to V with a solid carrier.
  • Granules e.g. coating, impregnation or homogeneous granules
  • a solid carrier e.g., a wax, a wax, or a wax.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers such as ammonium sulfate, ammonium phosphate, ammonium
  • the formulations generally contain from 0.1 to 95 wt .-%, preferably 0.5 to 90 wt .-% of one of the compounds I and min ⁇ least one of the compounds II to V or the mixture of the compounds I and at least one of the compounds II to V.
  • 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 IV for separate application.
  • the application can take place before or after infestation by the harmful fungi. 17
  • V a mixture, ground in a hammer mill, of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powder Silica gel; by fei ⁇ nes distributing the mixture in water gives a spray mixture; VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dust contains 3% by weight of active ingredient;
  • a stable aqueous dispersion of 40 parts by weight of the active ingredients, 10 parts by weight of the sodium salt of a phenol-sulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which is further diluted can be;
  • IX a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid urine 18 substance-formaldehyde condensates and 88 parts by weight of a paraffinic mineral oil.
  • the active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
  • ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
  • the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
  • Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

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 (V) in a synergistically effective quantity.

Description

Fungizide Mischungen auf der Basis von Tripeloximether-Derivaten und anderen StrobilurinenFungicidal mixtures based on triple oxime ether derivatives and other strobilurins
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.
CD
Figure imgf000003_0001
CD
Figure imgf000003_0001
OO
•R o • R o
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 , CHCH3 ;X STILL 3 , CHOCH 3 , CHCH 3 ;
0, NR0, NO
R jR unabhängig voneinander Wasserstoff und Cι-C4-Alkyl;R jR independently of one another hydrogen and -CC 4 alkyl;
R2 Cyano, Nitro, Trifluormethyl , Halogen, Cι-C -Alkyl und C]_-C -Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, -CC alkyl and C] _- C alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Cyano, Cι-C ~Alkyl , Cι-C -Halogenalkyl , C3-C5-Cycloalkyl ;R 3 is hydrogen, cyano, -CC alkyl, -C-haloalkyl, C 3 -C 5 cycloalkyl;
R4,R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-Cκ)-Alkenyl, C -Cιo-Alkinyl, Cι-Cιo-Alkylcarbonyl, C2-Cι0-Alkenyl- carbonyl , C3-Cιo-Alkinylcarbonyl oder Cι-Cιo-Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, 2-C-Cιo-alkyl, C 3 -C 6 cycloalkyl, C 2 -Cκ) alkenyl, C -Cιo-alkynyl, Cι-Cιo-alkylcarbonyl, C 2 -Cι 0 -alkenylcarbonyl, C 3 -Cιo-alkynylcarbonyl or -CC-alkyl sulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, 2
Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, Cχ-Cg-Halogenalkyl , Cι-C6-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl , Cι-C6-Alkoxy, Cι-C6-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkyl- thio, Ci-Cg-Alkylammo, Dι-Cι-Cg-alkylammo,Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, Cχ-Cg-Halogenalkyl, Cι-C 6 -Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl, Cι-C 6 -alkoxy, Cι-C 6 -haloalkoxy , Ci-Cg-alkoxycarbonyl, Ci-Cg-alkyl-thio, Ci-Cg-alkylammo, Dι-Cι-Cg-alkylammo,
Ci-Cg-Alkylammocarbonyl , Di-Ci-Cg-alkylammocarbonyl , Ci-Cg-Alkylammothiocarbonyl , Dι-Cι-Cg-alkylammothιo- carbonyl, C -C6-Alkenyl, C -C6-Alkenyloxy, C -Cg-Cyclo- alkyl, C -Cs-Cycloalkyloxy, Heterocyclyl , Hetero- cyclyloxy, Benzyl, Benzyloxy, Aryl , Aryloxy, Arylthio,Ci-Cg-alkylammocarbonyl, di-Ci-Cg-alkylammocarbonyl, Ci-Cg-alkylammothiocarbonyl, Dι-Cι-Cg-alkylammothιo- carbonyl, C -C 6 -alkenyl, C -C 6 -alkenyloxy, C -Cg-cyclo- alkyl, C -Cs-cycloalkyloxy, heterocyclyl, heterocyclicoxy, benzyl, benzyloxy, aryl, aryloxy, arylthio,
Hetaryl, Hetaryloxy und Hetarylthio, wobei die cycli- schen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, C].-Cg-Halogenalkyl, Cι-C6-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl , C -Cg-Cyclo- alkyl, Cx-Cg-Alkoxy, Cι-C6-Halogenalkoxy, Ci-Cg-Alkyl - oxycarbonyl, Cι-Cg-Alkylthιo, Cι-C6-Alkylammo, Dι-Cι-Cg-Alkylammo, Ci-Cg-Alkylammocarbonyl ,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, ammo, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg -Alkyl, C] .- Cg-haloalkyl, -C-C 6 alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C -Cg-cycloalkyl, Cx-Cg-alkoxy, Cι-C 6 -haloalkoxy, Ci-Cg-alkyl oxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylammo, D 1 -C 8 -Cg-alkylammo, C 1 -C 6 -alkylammocarbonyl,
Dι-Cι-Cg-Alkylammocarbonyl , Cι-Cg-Alkylammothιo- carbonyl, Di-Ci-Cg-Alkyla mothiocarbonyl , C2-C6- Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C (=NOR7) -An-R8;Dι-Cι-Cg-alkylammocarbonyl, Cι-Cg-alkylammothιo- carbonyl, di-Ci-Cg-alkylmothiocarbonyl, 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 - carbonyl oder Hetarylsulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können:Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups:
Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl , Cι-C6-Halogenalkyl, Cι-C6-Alkylcarbonyl , Ci-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , C -C6-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxy- carbonyl, Cι-Cg-Alkylthιo, Ci-Cg-Alkylammo, Dι-Cι-Cg- Alkylammo, Ci-Cg-Alkylammocarbonyl , Dι-Cι-Cg-Alkyl - ammocarbonyl, Ci-Cg-Alkylammothiocarbonyl , Dι-Cι-Cg- Alkylam othiocarbonyl, C2-Cg-Alkenyl, C2-Cg-Alkenyl - oxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl,Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, Cι-C 6 -Halogenalkyl, Cι-C 6 -Alkylcarbonyl, Ci-Cg-Alkyl- sulfonyl, Ci-Cg- Alkylsulfoxyl, C -C 6 cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxy-carbonyl, Cι-Cg-alkylthio, Ci-Cg-alkylammo, Dι-Cι-Cg-alkylammo, Ci -Cg-alkylammocarbonyl, Dι-Cι-Cg-alkyl - ammocarbonyl, Ci-Cg-alkylammothiocarbonyl, Dι-Cι-Cg-alkylam othiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyl - oxy, 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-Cg-Alkmyl , wobei dieCi-Cg-Alkyl, C 2 -Cg-Alkenyl, C 2 -Cg-Alkmyl, whereby the
Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis 3 drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Ammothiocarbonyl, Halogen, Ci-Cg-Alkylaminocarbonyl , Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , Ci-Cg-Alkoxy, Cχ-Cg- Halogenalkoxy, Ci-Cg-Alkoxycarbonyl , Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-alkylamino, C2-Cg-Alkenyloxy, C -Cg-Cycloalkyl, C3-Cg-Cycloalkyloxy, Heterocyclyl , Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cι-C -alkoxy,Hydrocarbon radicals of these groups can be partially or completely halogenated or one to 3 can carry three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothio-carbonyl, di- Ci-Cg-alkylaminothiocarbonyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Cχ-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, Di-Ci-Cg-alkylamino, C 2 -Cg-alkenyloxy, C -Cg-cycloalkyl, C 3 -Cg-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl -CC -alkoxy,
Arylthio, Aryl-Cι-C -alkylthio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C -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 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC -alkoxy, hetarylthio, hetaryl -CC-C 4 -alkyl - thio, where the cyclic radicals in turn can be partially or completely halogenated and / or one can carry up to three of the following groups:
Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Ammothiocarbonyl , Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl, C3Cg-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Haloalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl, C 3 Cg-Cycloalkyl, Ci-Cg- Alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-
Alkyla ino, 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, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C (=NOR7) -An-R8;Alkyla ino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylamino-thiocarbonyl, di-C-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 7 ) -A n -R 8 ;
C3 -Cg-Cycloalkyl , C3 -Cg -Cycloalkenyl , Heterocyclyl, 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, Amino - carbonyl, Aminothiocarbonyl , Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkyl- sulfoxyl, C3-Cg-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogen- alkoxy, 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 -Cg-Alkenyl , C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;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, amino-carbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy, Ci -Cg-haloalkoxy, Ci-Cg-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 -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
wobei für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cg-Alkyl trägt;in which 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 einem Fungizid ausgewählt aus Fungiziden der Formeln II bis Vb) at least one fungicide selected from fungicides of the formulas II to V
^^ N' 'N^^ N '' N
(II)(II)
O' O'
Figure imgf000006_0001
O ' o '
Figure imgf000006_0001
CN ,OMeCN, OMe
CH302CCH 3 0 2 C
; ιιi )
Figure imgf000006_0002
; ιιi)
Figure imgf000006_0002
-^ ^^- ^ ^^
(IV)(IV)
O' O '
CH3NH .OMeCH 3 NH .OMe
N'N '
O (V)O (V)
.0..0.
*CH,
Figure imgf000007_0001
 * CH,
Figure imgf000007_0001
Der vorliegenden Erfindung lag die Aufgabe zugrunde, fungizide Mischungen zur Verfugung zu stellen, die eine gute, über die Wirksamkeit der Mischungskomponenten allem hinausgehende fungi- zide Wirkung, insbesondere gegen Pilzerkrankungen 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, in particular against rice fungal diseases.
Diese Aufgabe wird erf dungsgemäß durch die Mischungen gemäß Anspruch 1 gelost.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).
D e Fungizide der Formeln II bis V sind ebenfalls bekannt und in der Literatur beschrieben. Darüber hinaus sind sie ggf. unter den nachfolgend m Klammern genannten Handelsnamen kommerziell erhältlich:The fungicides of the formulas II to V are also known and described in the literature. In addition, they may be commercially available under the trade names given below in brackets:
II: Common name: Azoxystrobm (Handelsname: Amistar®, Fa. Zeneca)II: Common name: Azoxystrobm (trade name: Amistar®, Zeneca)
III: EP- A 253,313, Common name: Kresoxim-methyl (Handelsname Bπo®, Fa. BASF)III: EP-A 253,313, common name: Kresoxim-methyl (trade name Bπo®, from BASF)
IV: EP 398,692, vorgeschlagener Common name: Metommostrobm (Entwicklungscode SSF-126, Fa. Shionogi);IV: EP 398,692, proposed common name: Metommostrobm (development code SSF-126, Shionogi);
V: EP 398,692, CAS RN 162535-21-9, SSF 129, Entwicklungspro¬ dukt der Fa. Shionogi Co., Ltd.)V: EP 398.692, CAS RN 162535-21-9, SSF 129, Entwicklungspro ¬ domestic product of the company Shionogi & Co., Ltd.).
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 m die Einzelverbmdungen 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, the individual compounds can be separated by crystallization or chromatography in the usual way.
Sofern bei der Synthese Isomerengemisehe anfallen, ist im allgemeinen jedoch eine Trennung nicht unbedingt erforderlich, da sich die einzelnen Isomere teilweise wahrend der Aufbereitung für 6 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 the synthesis of isomers occurs in the synthesis, a separation is generally not absolutely necessary, since the individual isomers are partially separated during processing 6 can convert the application into one another (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 (Konfiguration bezogen auf die -OCH3 bzw. die -CH3 -Gruppe im Verhältnis zur -CO2R1 Gruppe) .With regard to the C = X double bond, the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
In Bezug auf die -C (R3) =N0CH2- Doppelbindung werden hinsichtlich ihrer Wirksamkeit die cis-Isomere der Verbindungen I bevorzugt (Konfiguration bezogen auf den Rest R3 im Verhältnis zur -OCH2- Gruppe) .With regard to the -C (R 3 ) = NOCH 2 double bond, the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
Bei der eingangs angegebenen Definitionen der Verbindungen I wurden Sammelbegriffe verwendet, die allgemein repräsentativ für die folgenden Gruppen stehen:In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:
Halogen: Fluor, Chlor, Brom und Jod;Halogen: fluorine, chlorine, bromine and iodine;
Alkyl : geradkettige oder verzweigte Alkylgruppen mit 1 bis 4, 6 oder 10 Kohlenstoffatomen, z.B. Ci-Cg-Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl , Butyl, 1-Methyl-propyl , 2-Methylpropyl , 1,1-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;
Halogenalkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder voll¬ ständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. Cι-C2-Halogenalkyl wie Chlor¬ methyl, Dichlormethyl, Trichlormethyl , Fluormethyl, Difluor- methyl, Trifluormethyl , Chlorfluormethyl, Dichlorfluor ethyl,Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms, wherein the hydrogen atoms constantly may be substituted as mentioned above by halogen atoms in these groups to be partially or fully ¬ such as Cι-C 2 -haloalkyl such as chloro ¬ methyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoroethyl,
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; 7Chlorodifluoromethyl, 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; 7
Cycloalkyl: monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoff - ringgliedern, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl;Cycloalkyl: monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Alkenyl: geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 oder 10 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C -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, e.g. C -Cg alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1- Methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,
4-Pentenyl, 1-Methyl-l-butenyl , 2-Methyl-l-butenyl , 3 -Methyl-1- 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-1-pentenyl , 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, l-Methyl-2-pentenyl , 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl , l-Methyl-3-pentenyl , 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl , 4-Methyl-3-pentenyl , l-Methyl-4-pentenyl, 2-Methyl-4-pentenyl , 3-Methyl-4-pentenyl , 4-Methyl-4-pentenyl, 1, l-Dimethyl-2-butenyl , 1 , l-Di-methyl-3- butenyl, 1, 2-Dimethyl-l-butenyl , 1, 2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, 1, 3-Dimethyl-l-butenyl , 1, 3-Dimethyl-2- butenyl, 1, 3-Dimethyl-3-butenyl , 2 , 2-Dimethyl-3-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-butenyl, 1, 2-dimethyl-l- butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3- butenyl, 2, 2-dimethyl-3-butenyl,
2 , 3-Dimethyl-l-butenyl, 2 , 3-Dimethyl-2-butenyl , 2 , 3-Dimethyl-3- butenyl, 3 , 3-Dimethyl-l-butenyl , 3 , 3-Dirnethyl-2-butenyl , 1-Ethyl-l-butenyl, l-Ethyl-2-butenyl , l-Ethyl-3-butenyl , 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl , 2-Ethyl-3 -butenyl , 1, l,2-Trimethyl-2-propenyl, 1- Ethyl-l-methyl-2-propenyl, l-Ethyl-2-methyl-l-propenyl und l-Ethyl-2-methyl-2-propenyl;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-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 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 be- liebigen Position, z.B. C2-Cg-Alkinyl wie Ethinyl, 2-Propinyl, 2-Butinyl, 3-Butinyl, l-Methyl-2-propinyl , 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2-butinyl , l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 1, l-Dimethyl-2-propinyl , l-Ethyl-2-propinyl , 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, l-Methyl-2-pentinyl , l-Methyl-3-pentinyl, l-Methyl-4-pentinyl , 2-Methyl-3-pentinyl , 2-Methyl-4-pentinyl, 3-Methyl-4-pentinyl , 4-Methyl-2-pentinyl , 1, l-Dimethyl-2-butinyl, 1 , l-Dimethyl-3-butinyl , 1 , 2-Dimethyl- 3-butinyl, 2 , 2-Dimethyl-3-butinyl , l-Ethyl-2-butinyl , 1-Ethyl- 3-butinyl, 2-Ethyl-3-butinyl und l-Ethyl-l-methyl-2-propinyl ; 8Alkynyl: 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 -propinyl; 8th
Heterocyclyl bzw. Heterocyclyloxy, Heterocyclylthio und Hetero- cyclylamino: drei- bis sechsgliedrige, gesättigte oder partiell ungesättigte mono- oder polycyclische Heterocyclen, die ein bis drei Hereroatome ausgewählt aus einer Gruppe bestehend aus Sauer - Stoff, Stickstoff und Schwefel enthalten, und welche direkt bzw. (Heterocyclyloxy) über ein Sauerstoffatom oder (Heterocyclylthio) über ein Schwefelatom oder (Heterocyclyla ino) über ein Stickstoffatom an das Gerüst gebunden sind, wie z.B. 2 -Tetrahydro- furanyl, Oxiranyl, 3 -Tetrahydrof ranyl , 2 -Tetrahydrothienyl, _ 3 -Tetrahydrothienyl, 2 -Pyrrolidinyl, 3 -Pyrrolidinyl, 3-Isoxazol- dinyl, 4 -Isoxazolidinyl, 5 - Isoxazolidinyl, 3 -Isothiazolidinyl, 4 -Isothiazolidinyl, 5 -Isothiazolidinyl, 3 -Pyrazolidinyl, 4 -Pyrazolidinyl, 5 - Pyrazolidinyl, 2 -Oxazolidinyl, 4 -Oxazolidinyl, 5 -Oxazolidinyl , 2 -Thiazolidinyl , 4 -Thiazolidinyl , 5-Thia- zolidinyl, 2 - Imidazolidinyl , 4 -I idazolidinyl , 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 , 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-fur-4-yl, 2 , 3 -Dihydro-fur-5 -yl , 2 , 5 -Dihydro-fur-2 -yl, 2,5-Dihydro-fur-3-yl, 2 , 3 -Dihydrothien-2 -yl , 2,3-Dihydro- thien-3-yl, 2 , 3 -Dihydrothien-4 -yl , 2 , 3 -Dihydrothien- 5 -yl, 2 , 5 -Dihydrothien-2 -yl, 2 , 5 -Dihydrothien- 3 -yl , 2,3-Dihydro- pyrrol-2-yl, 2 , 3 -Dihydropyrrol -3 -yl , 2 , 3 -Dihydropyrrol -4 -yl , 2, 3 -Dihydropyrrol- 5 -yl, 2 , 5 -Dihydropyrrol -2 -yl, 2,5-Dihydro- pyrrol-3 -yl , 2,3 -Dihydroisoxazol -3 -yl, 2 , 3 -Dihydroisoxazol -4 -yl, 2 , 3 -Dihydroisoxazol -5 -yl, 4 , 5 -Dihydroisoxazol - 3 -yl, 4 , 5 -Dihydro¬ isoxazol -4 -yl , 4 , 5 -Dihydroisoxazol -5 -yl , 2 , 5 -Dihydroisothia- zol -3 -yl, 2,5 -Dihydroisothiazol -4 -yl , 2,5 -Dihydroisothiazol -5 -yl, 2 , 3 -Dihydroisopyrazol -3 -yl, 2 , 3 -Dihydroisopyrazol -4 -yl , 2,3-Dihy- droisopyrazol -5 -yl , 4 , 5 -Dihydroisopyrazol - 3 -yl , 4 , 5 -Dihydroisopyrazol -4 -yl , 4 , 5 -Dihydroisopyrazol -5 -yl, 2 , 5 -Dihydroisopyra¬ zol -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 -Dihydrothiazol -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 ,Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclyllamino: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles, which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or . (Heterocyclyloxy) via an oxygen atom or (Heterocyclylthio) via a sulfur atom or (Heterocyclyla ino) via a nitrogen atom are bound to the skeleton, such as 2-tetrahydrofuran, oxiranyl, 3-tetrahydrofranyl, 2-tetrahydrothienyl, _ 3 - Tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoledinyl, 4 -isoxazolidinyl, 5-isoxazolidinyl, 3 -isothiazolidinyl, 4 -isothiazolidinyl, 5 -isothiazolidinyl, 3 -pyrazolidinyl, 4 -pyrazolidinyl, 5 - pyrazolidinyl Oxazolidinyl, 4 -oxazolidinyl, 5 -oxazolidinyl, 2 -thiazolidinyl, 4 -thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4 -I idazolidinyl, 1,2,4-oxadiazolidin-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-fur-4-yl, 2,3-dihydro-fur-5-yl, 2,5-dihydro-fur-2-yl, 2,5-dihydro-fur-3-yl, 2, 3 -dihydrothien-2 -yl, 2,3-dihydrothien-3-yl, 2, 3 -dihydrothien-4 -yl, 2, 3 -dihydrothien-5 -yl, 2, 5 -dihydrothien-2 - yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrole-2-yl, 2,3-dihydropyrrole -3-yl, 2,3-dihydropyrrole -4-yl, 2,3-dihydropyrrole- 5 -yl, 2, 5 -dihydropyrrole -2 -yl, 2,5-dihydropyrrole-3 -yl, 2,3 -dihydroisoxazole -3 -yl, 2, 3 -dihydroisoxazole -4 -yl, 2, 3 - Dihydroisoxazole -5 -yl, 4, 5 -Dihydroisoxazol - 3 -yl, 4, 5 -Dihydro ¬ isoxazol -4 -yl, 4, 5 -Dihydroisoxazol -5 -yl, 2, 5 -Dihydroisothia- zol -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 -Dihydroisopyrazol - 3 -yl, 4, 5 -Dihydroisopyrazol -4 -yl, 4, 5 -Dihydroisopyrazole -5 -yl, 2, 5 -Dihydroisopyra ¬ zol -3 -yl, 2, 5 -Dihydroisopyrazol -4 -yl, 2, 5 -Dihydroisopyrazol -5 -yl, 2, 3 -Dihydrooxazol-3 -yl, 2 , 3-dihydrooxazole -4 -yl, 2,3-dihydro-oxazol-5-yl, 4,5 -dihydrooxazole -3 -yl, 4,5 -dihydrooxazole -4 -yl, 4,5 -dihydrooxazole -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 -dihydrothiazole - 5 -yl, 4,5-dihydro-thiazole -2 -yl, 4, 5 -dihydrothiazole -4 -yl, 4, 5 -dihydrothiazole -5 -yl, 2, 5 -dihydrothiazole -2 -yl, 2, 5 -dihydrothiazole -4 -yl, 2, 5 -dihydrothiazole -5 -yl, 2,3 -dihydroimidazol-2 -yl, 2, 3 -dihydroimidazole -4 -yl, 2, 3 -dihydroimidazole -5 -yl, 4, 5 -dihydroimidazole -2 -yl, 4, 5 -dihydroimidazole -4 -yl, 4, 5 -dihydroimidazole -5 -yl, 2, 5 -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- 9 pyrimidinyl , 2 -Tetrahydropyrazinyl , 1,3,5 -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 ,4 - piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydro- 9 pyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-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-benzothiazine-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 (-S0 -) an das Gerüst gebunden sind, z.B. Phenyl , Naphthyl und Phenanthrenyl bzw. Phenyloxy, Naphthyloxy und Phenanthrenyl - oxy und die entsprechenden Carbonyl- und Sulfonylreste;Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) are bonded to the skeleton via a sulfonyl group (-S0 -), 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 vierHetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which in addition to carbon ring members additionally one to four
Stickstoffatome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom oder ein Sauerstoff- oder ein Schwefelatom enthalten können und welche direkt bzw. (Hetaryloxy) über ein Sauerstoffatom (-0-) oder (Hetarylthio) ein Schwefelatom (-S-), (Hetarylcarbonyl) über eine Carbonylgruppe (-CO-) oderNitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-), (Hetarylcarbonyl) via a carbonyl group (-CO-) or
(Hetarylsulfonyl) über eine Sulfonylgruppe (-S02-) an das Gerüst gebunden sind, z.B.(Hetarylsulfonyl) are attached to the skeleton via a sulfonyl group (-S0 2 -), for example
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-Isoxazolyl, 3-Isothiazolyl , 4-Isothiazolyl, 5-Isothiazolyl, 3-Pyrazolyi, 4-Pyrazolyl, 5-Pyrazolyl, 2-0xazolyl, 4-0xazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 105-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-pyrazolyi, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-0xazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 10
5-Thiazolyl, 2-Imidazolyl , 4-Imidazolyl , 1, 2 , 4-Oxadiazol- 3-yl, 1,2, 4-Oxadiazol-5-yl, 1, 2 , 4-Thiadiazol-3-yl , l,2,4-Thiadiazol-5-yl, 1, 2 , 4-Triazol-3-yl , 1,3, 4-Oxadiazol-2-yl, 1,3, 4-Thiadiazol-2-yl , l,3,4-Triazol-2-yl;5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazol-3-yl, 1,2, 4-oxadiazol-5-yl, 1, 2, 4-thiadiazol-3-yl, l, 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-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome oder ein Stickstoffatom und/oder ein Sauerstoff- oder Schwefelatom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder ein Schwefelatom als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglieder oder ein Stickstoff- und ein benach- bartes Kohlenstoffringglied durch eine Buta-1, 3-dien- 1, 4-diylgruppe verbrückt sein können;Benzo-fused 5-membered heteroaryl, containing one to three nitrogen atoms or one nitrogen atom and / or one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or 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 Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome bzw. ein bis drei Stickstoffatome als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlen- Stoffringglieder oder ein Stickstoff- und ein benachbartes5-membered heteroaryl bonded via nitrogen, containing one to four nitrogen atoms, or benzo-fused 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 as ring members may contain, and in which two adjacent carbon ring members or a nitrogen and an adjacent
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;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 , 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- etrazi - 3 -yl ;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 and 1,2,4,5-etrazi-3 -yl;
benzokondensiertes 6-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome: 6 -Ring Heteroarylgruppen in welchen zwei benachbarte Kohlenstoffringglieder durch eine Buta- 1, 3 -dien-1, 4 -diylgruppe verbrückt sein können, z.B. Chinolin, Isochinolin, Chinazolin und Chinoxalin,benzo-fused 6-membered heteroaryl containing one to four nitrogen atoms: 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta- 1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
bzw. die entsprechenden Oxy-, Thio-, Carbonyl- oder Sulfonyl- gruppen. 11or the corresponding oxy, thio, carbonyl or sulfonyl groups. 11
Hetarylammo: aromatische mono- oder polycyclische Reste, welche neben Kohlenstoffrmggliedern zusatzlich ein bis vier Stickstoff - atome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom enthalten können und welche über e n Stickstoff - atom an das Gerüst gebunden sind.Hetarylammo: aromatic mono- or polycyclic radicals which, in addition to carbon members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
Die Angabe "partiell oder vollständig halogeniert" soll zum Aus¬ druck bringen, daß in den derart charakterisierten Gruppen die Wasserstoffatome zum Teil oder vollständig durch gleiche oder verschiedene Halogenatome wie vorstehend genannt ersetzt sein könne .The specification should be "partially or fully halogenated" to bring pressure from ¬ that in groups characterized thus, the hydrogen atoms can be replaced entirely as mentioned above, by identical or different halogen atoms or in part.
Im Hinblick auf ihre biologische Wirkung sind Verbindungen der Formel I bevorzugt, m 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, m denen R1 für Methyl steht.Equally preferred are compounds of the formula I in which R 1 is methyl.
Daneben werden Verbindungen I bevorzugt, m denen R3 für Wasser - stoff, Cyano, Cyclopropyl, Methyl, Ethyl, 1 -Methylethyl oder CF3 steht.In addition, compounds I are preferred in which R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
Außerdem werden Verbindungen I bevorzugt, m denen R3 für Methyl steht .In addition, compounds I are preferred in which R 3 is methyl.
Daneben werden Verbindungen I bevorzugt, m denen R3 für Cyano steht.In addition, compounds I are preferred in which R 3 is cyano.
Weiterhin werden Verbindungen I bevorzugt, denen R3 für Cyclo- propyl steht.Compounds I are furthermore preferred, in which R 3 represents cyclopropyl.
Des weiteren werden Verbindungen I bevorzugt, m denen R3 für CF3 steht.Furthermore, compounds I are preferred in which R 3 is CF 3 .
Des weiteren werden Verbindungen I bevorzugt, m denen R5 für Wasserstoff, Cyclopropyl, Methyl, Ethyl, iso- Propyl, ggf. subst. Aryl oder Hetaryl steht.Furthermore, preference is given to compounds I in which R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, optionally subst. Aryl or hetaryl is.
Außerdem werden Verbindungen I bevorzugt, m denen R5 für Methyl steht.In addition, compounds I are preferred in which R 5 is methyl.
Des weiteren werden Verbindungen I bevorzugt, m denen R5 für Ethyl steht.Furthermore, compounds I are preferred in which R 5 is ethyl.
Außerdem werden Verbindungen I bevorzugt, m denen R5 für Iso -Propyl steht. 12In addition, compounds I are preferred in which R 5 is isopropyl. 12
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 CF steht.In addition, compounds I are preferred in which R 5 is CF.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Aryl oder Hetaryl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Aryl or hetaryl is.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Pyridyl, Pyrimidyl, Pyrazinyl, Pyridazinyl oder Triazinyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Furyl, Thienyl oder Pyrrolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Furyl, thienyl or pyrrolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Oxazolyl, Thiazolyl, Isoxazolyl, Isothiazolyl , Pyrazolyl oder Imidazolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Oxdiazolyl, Thiadiazolyl oder Triazolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Phenyl steht, welches unsubstituiert ist oder ein oder zwei der folgenden Gruppen trägt: Nitro, Cyano, Hydroxy, Amino, Ammocarbonyl , Ammothiocarbonyl, Halogen, Cι-C -Alkyl, Cι-C -Halogenalkyl, Cι-C -Alkoxy, Cι-C -Halogenalkoxy, C -C -Alkylamino, Di-Cι-C - Alkylamino, Cι~C -Alkylsulfonyl , Cι-C -Alkoxycarbonyl , Cι-C -Alkyl- aminocarbonyl oder Di-Cι-C -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, ammocarbonyl, ammothiocarbonyl, halogen, C 1 -C 4 alkyl, C 1 -C 4 Haloalkyl, -C-C alkoxy, -C-C -halalkalkoxy, C -C -alkylamino, di-Cι-C - alkylamino, Cι-C -alkylsulfonyl, Cι-C -alkoxycarbonyl, Cι-C -alkyl- aminocarbonyl or di- -CC alkylaminocarbonyl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Wasserstoff, Ci-Cg-Alkyl, C2-Cg -Alkenyl, C2 -C -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 -Cg -alkenyl, C 2 -C -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 13The compounds I contained in the mixtures according to the invention are distinguished by an outstanding action against a broad spectrum of phytopathogenic fungi, in particular against 13
Pilze aus den Klassen der Ascomyceten, Deuteromyceten, Phycomyce- ten und Basisiomyceten aus.Mushrooms from the classes of Ascomycetes, Deuteromycetes, Phycomycetes and Basisiomycetes.
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. 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) 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, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudocercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Arten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosphaerella-Arten in Ba- nanen 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, Helminthospori - um species on cereals, 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, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species on vegetables and fruit, Mycosphaerella species in Ba nanen and Fusarium and Verticillium species.
Die Verbindungen II bis V sind als Fungizide kommerziell erhältlich.The compounds II to V are commercially available as fungicides.
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I und II bis V ein, denen man weitere Wirkstoffe gegen Schadpilze oder gegen andere Schädlinge wie Insek¬ ten, Spinntiere oder Nematoden oder auch herbizide oder Wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann .Preferably employed in the preparation of the mixtures the pure active compounds I and II to V, where th further active ingredients against harmful fungi or against other pests, such as Insek ¬, arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers.
Die Mischungen aus den Verbindungen I und mindestens einer Verbindung II bis V 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, Phyco- myceten und Deuteromyceten aus. Sie sind z.T. systemisch wirksam und können daher auch als Blatt- und Bodenfungizide eingesetzt werden. 14The mixtures of the compounds I and at least one compound II to V 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. Some of them are systemically effective and can therefore also be used as leaf and soil fungicides. 14
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, Obstpflan- zen, Reis, Roggen, Soja, Wem, Weizen, Zierpflanzen, Zuckerrohr sowie an einer Vielzahl von Samen.They are particularly important for combating a large number of mushrooms on various crops such as cotton, vegetables (eg cucumber, beans, tomatoes, potatoes and squashes), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye , Soy, who, wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe grammis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuligmea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncmula necator an Reben, Puccmia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, üstilago-Arten an Getreide und Zuk- kerrohr, Venturia maequalis (Schorf) an Äpfeln, Helm thospori- um-Arten an Getreide und Reis, Septoπa nodorum an Weizen,They are particularly suitable for combating the following phytopathogenic fungi: Erysiphe grammis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuligmea on pumpkin plants, Podosphaera leucotricha on apples, Uncmula necator on vines, Puccmia cotton on cereals, Rhizo species Rice and lawn, üstilago species on cereals and sugar cane, Venturia maequalis (scab) on apples, Helm thosporium species on cereals and rice, Septoπa nodorum on wheat,
Botrytis cmera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudo- cercosporella herpotπchoides an Weizen und Gerste, Pyπcularia oryzae an Reis und Rasen, Phytophthora festans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Ar - ten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosp aerella-Arten m Bananen sowie Fusarium- und Verticillium- Arten.Botrytis cmera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudo-cercosporella herpotπchoides on wheat and barley, Pyπcularia oryzae on rice and lawn, Phytophthora festans on potatoes and tomatoes, Plasmopara viticoperonosa on vines, Pseudo - in hops and cucumbers, Alternaria species in vegetables and fruits, Mycosp aerella species in bananas and Fusarium and Verticillium species.
Besonders bevorzugt sind die erf dungsgemaßen Mischungen zur Bekämpfung von Pyπcularia oryzae einsetzbar.The mixtures according to the invention can be used particularly preferably for controlling Pyπcularia oryzae.
Die Verbindungen I und mindestens eine der Verbindungen II bis V können gleichzeitig, und zwar gemeinsam oder getrennt, oder nach- einander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungs - erfolg hat.The compounds I and at least one of the compounds II to V 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 control success.
Die Aufwandmengen der erfmdungsgemaßen Mischungen liegen, vor allem bei landwirtschaftlichen Kulturflachen, j e 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 inventive mixtures are, in particular in agricultural crop surfaces, depending on the nature of the effect desired ge ¬ from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 kg /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 V liegen entsprechend bei 0,001 bis 5 kg/ha, vorzugsweise 0,005 bis 2 kg/ha, ms - besondere 0,01 bis 1,0 kg/ha. 15The application rates for the compounds II to V are accordingly 0.001 to 5 kg / ha, preferably 0.005 to 2 kg / ha, ms - particularly 0.01 to 1.0 kg / ha. 15
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 V durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.If pathogenic harmful fungi are to be combated for plants, the separate or joint application of the compounds I and at least one of the compounds II to V is carried out by spraying or dusting the seeds, the plants or the soil before or after the plants have been sown or before or after the Emergence of plants.
Die erfindungsgemäßen fungiziden synergistischen Mischungen können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen 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.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.
Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/oder Trä- gerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdünnungsmittel auch andere organische Lösungsmittel als Hilfslösungsmittel verwendet werden können. Als HilfsStoffe kommen dafür im wesentlichen in Betracht: Lösungsmittel wie Aromaten (z.B. Xylol) , chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol) , Ketone (z.B. Cy- 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 auxiliary substances: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine , Dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
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-, Laurylet er- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolethern, Kondensationspro - dukte von sulfoniertem Naphthalin und seinen Derivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bz,v. der 16The surface-active substances are the alkali, alkaline earth, and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl and fatty alcohol sulfates, and salts of sulfated hexa -, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or,. the 16
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 V oder der Mischung aus den Verbindungen I und mindestens einer Verbindung II bis V mit einem festen Trägerstoff hergestellt werden.Powder sprinklers and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to V or the mixture of the compounds I and at least one compound II to V with a solid carrier.
Granulate (z.B. Umhüllungs-, Imprägnierungs- oder Homogen - granulate) 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, Dolomit, 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 soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% einer der Verbindungen I und min¬ destens einer der Verbindungen II bis V bzw. der Mischung aus den Verbindungen I und mindestens einer der Verbindungen II bis V. Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100 %, vorzugsweise 95 % bis 100 % (nach NMR- oder HPLC-Spektrum) einge- setzt.The formulations generally contain from 0.1 to 95 wt .-%, preferably 0.5 to 90 wt .-% of one of the compounds I and min ¬ least one of the compounds II to V or the mixture of the compounds I and at least one of the compounds II to V. 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 IV 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 IV for separate application.
Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen. 17The application can take place before or after infestation by the harmful fungi. 17
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-monoethanolamid, 5 Gew. -Teilen Calciumsalz der Dodecylbenzolsulfonsäure, 5II. A mixture of 20 parts by weight of the active ingredients, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid , 5th
Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl; durch feines Verteilen der Lösung in Wasser erhält man eine Dispersion;Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil; a dispersion is obtained by finely distributing the solution in water;
III. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 40 Gew. -Teilen Cyclohexanon, 30 Gew. -Teilen Isobutanol, 20III. an aqueous dispersion of 20 parts by weight of the active ingredients, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20
Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl;Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil;
IV. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 25 Gew. -Teilen Cyclohexanol , 65 Gew. -Teilen einer Mine- ralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl;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 1 mole of castor oil;
V. eine in einer Hammermühle vermahlene Mischung aus 80 Gew.- Teilen der Wirkstoffe, 3 Gew. -Teilen des Natriumsalzes der Diisobutylnaphthalin-1-sulfonsäure, 10 Gew. -Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfitablauge und 7 Gew. -Teilen pulverförmigem Kieselsäuregei ; durch fei¬ nes Verteilen der Mischung in Wasser erhält man eine Spritzbrühe; VI. eine innige Mischung aus 3 Gew. -Teilen der Wirkstoffe und 97 Gew. -Teilen feinteiligem Kaolin; dieses Stäubemittel enthält 3 Gew.-% Wirkstoff;V. a mixture, ground in a hammer mill, of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powder Silica gel; by fei ¬ nes distributing the mixture in water gives a spray mixture; VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dust contains 3% by weight of active ingredient;
VII. eine innige Mischung aus 30 Gew. -Teilen der Wirkstoffe, 92 Gew. -Teilen pulverförmigem Kieselsäuregel und 8 Gew. -Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde; diese Aufbereitung gibt dem Wirkstoff eine gute Haftfähigkeit;VII. An intimate mixture of 30 parts by weight of the active ingredients, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel; this preparation gives the active ingredient good adhesion;
VIII. eine stabile wäßrige Dispersion aus 40 Gew. -Teilen der Wirkstoffe, 10 Gew. -Teilen des Natriumsalzes eines Phenol - sulfonsäure-Harnstoff-Formaldehyd-Kondensates, 2 Gew. -Teilen Kieselgel und 48 Gew. -Teilen Wasser, die weiter verdünnt werden kann;VIII. A stable aqueous dispersion of 40 parts by weight of the active ingredients, 10 parts by weight of the sodium salt of a phenol-sulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which is further diluted can be;
IX. eine stabile ölige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 2 Gew. -Teilen des Calciumsalzes der Dodecylbenzol - sulfonsäure, 8 Gew. -Teilen Fettalkohol-polyglykolether, 20 Gew. -Teilen des Natriumsalzes eines Phenolsulfonsäure-Harn- 18 stoff-Formaldehydkondensates und 88 Gew. -Teilen eines paraffinischen Mineralöls.IX. a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid urine 18 substance-formaldehyde condensates and 88 parts by weight of a paraffinic mineral oil.
Die synergistische Wirkung der erfmdungsgemaßen Mischungen läßt sich durch die folgenden Versuche zeigen:The synergistic effect of the mixtures according to the invention can be demonstrated by the following experiments:
Die Wirkstoffe werden getrennt oder gemeinsam als 10 %ige Emulsion in einem Gemisch aus 63 Gew.-% Cyclohexanon und 27 Gew.-% Emulgator aufbereitet und entsprechend der gewünschten Konzentra- tion mit Wasser verdünnt.The active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
Die Auswertung erfolgt durch Feststellung der befallenen Blatt - flächen in Prozent. Diese Prozent-Werte werden in Wirkungsgrade umgerechnet. Der Wirkungsgrad (W) wird nach der Formel von Abbot wie folgt bestimmt:The evaluation is carried out by determining the affected leaf areas in percent. These percentages are converted into efficiencies. Efficiency (W) is determined using Abbot's formula as follows:
W = (1 - α) -100/ßW = (1 - α) -100 / ß
α entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in %α corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 wiesen die behandelten Pflanzen keinen Befall auf.With an efficiency of 0, the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
Die zu erwartenden Wirkungsgrade der Wirkstoffmischungen wurden nach der Colby Formel [R.S. Colby, Weeds 15., 20-22 (1967)] ermit¬ telt und mit den beobachteten Wirkungsgraden verglichen.The expected efficacies of active compound mixtures were [15 RS Colby, Weeds, 20-22 (1967)] according to the Colby formula ermit ¬ telt and compared with the observed efficacies.
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
Anwendungsbeispiel 1 - Wirksamkeit gegen Pyricularia oryzae (protektiv) 19Example of use 1 - Activity against Pyricularia oryzae (protective) 19
Blätter von in Töpfen gewachsenen Reiskeimlingen der Sorte "Tai- Nong 67" wurden mit wäßriger Wirkstoffaufbereitung, die mit einer Stammlösung aus 10 % Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wurde, bis zur Tropfnässe besprüht. Am folgenden Tag wurden die Pflanzen mit einer wäßrigen Sporensuspension von Pyricularia oryzae inokuliert. Anschließend wurden die Versuchspflanzen in Klimakammern bei 22 - 24° C und 95 - 99 % relativer Luftfeuchtigkeit für 6 Tage aufgestellt. Dann wurde das Ausmaß der Befallsentwicklung auf den Blättern visuell ermitteltLeaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually
Die visuell ermittelten Werte für den Prozentanteil befallener Blattflächen wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel (Colby, S. R. (Calculating synergistic and anta- gonistic responses of herbicide Combinations" , Weeds, 15, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen.The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The expected efficacies for combinations of active substances were determined using the Colby formula (Colby, S.R. (Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies.
Als Komponente a) wurde folgende Verbindung I' eingesetzt:The following compound I 'was used as component a):
H3C-H 3 C-
/O-CH, / O-CH,
Figure imgf000021_0001
Figure imgf000021_0001
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. KontrolleFor example, active ingredient conc in ppm efficiency in% of unhindered control
IV ohne (100 % Befall) 0IV without (100% infestation) 0
2V Verbindung I' 2,0 20 0,5 02V connection I '2.0 20 0.5 0
3V Verbindung II 0,5 20 (common name: Azo- xystrobin)3V connection II 0.5 20 (common name: Azoxystrobin)
4V Verbindung III 2,0 04V connection III 2.0 0
(common name: Kre- 0,5 0 soxim-methyl)
Figure imgf000021_0002
20(common name: Kre- 0.5 0 soxim-methyl)
Figure imgf000021_0002
20th
Tabelle 2Table 2
Bsp. erfindungsgemäße Mischung beobachteter berechneter (Konz. in ppm) Wirkungsgrad Wirkungsgrad*For example, the mixture of calculated calculated (conc. In ppm) efficiency according to the invention efficiency *
5 0,5 ppm 1 + 0,5 ppm II 40 205 0.5 ppm 1 + 0.5 ppm II 40 20
6 2 ppm 1 + 2 ppm III 80 206 2 ppm 1 + 2 ppm III 80 20
7 0,5 ppm 1 + 0,5 ppm III 20 0
Figure imgf000022_0001
berechnet nach der Colby-Formel7 0.5 ppm 1 + 0.5 ppm III 20 0
Figure imgf000022_0001
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

21Patentansprüche 21 patent claims
1 . Mischungen für den Pf lanzenschutz , enthaltend als aktive Kom- ponenten1 . Mixtures for plant protection, containing as active components
a) Phenyless igsäurederivate der Formel Ia) Phenylacetic acid derivatives of the formula I.
(I)(I)
Figure imgf000023_0001
Figure imgf000023_0001
m der die Substituenten und der Index die folgende Be- deutung haben:m where the substituents and the index have the following meaning:
X NOCH3, CHOCH3, CHCH3 ;X STILL 3 , CHOCH 3 , CHCH 3 ;
Y 0, NRY 0, NO
R^R unabhängig voneinander Wasserstoff und Cι~C -Alkyl;R ^ R independently of one another hydrogen and Cι ~ C alkyl;
R2 Cyano, Nitro, Trifluormethyl , Halogen, Cι~C -Alkyl und Cι-C -Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, -C ~ alkyl and -C -C alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Cyano, Cι-C -Alkyl, Cι-C -Halogen- alkyl, C3-C6-Cycloalkyl;R 3 is hydrogen, cyano, -CC alkyl, -C -C halogen alkyl, C 3 -C 6 cycloalkyl;
R4,R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
Cι-Cιo-Alkyl, C -C6-Cycloalkyl, C2-Cιo-Alkenyl , C -Cιo-Alkmyl, Cι-Cιo-Alkylcarbonyl ,-C-Cιo-alkyl, C -C 6 -cycloalkyl, C 2 -Cιo-alkenyl, C -Cιo-alkmyl, Cι-Cιo-alkylcarbonyl,
C2-Cιo-Alkenylcarbonyl , C3-C o-Alkmylcarbonyl oder Cι-Cιo-Alkylsulfonyl , wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen kon- nen: Cyano, Nitro, Hydroxy, Mercapto, Ammo,C 2 -Co-alkenylcarbonyl, C 3 -C o-alkmylcarbonyl or Cι-Cιo-alkylsulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, Ammo,
Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, 22Carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, 22
Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl , Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Cι~Cg-Alkoxy- carbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-alkylamino ,Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Cι ~ Cg-alkoxy-carbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg- alkylamino,
Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-alkylamino- carbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C -Cg-Alkenyl , C2-Cg-Alkenyloxy, C3-Cg-Cycloalkyl , C3-Cg-Cycloalky- _ loxy, Heterocyclyl, Heterocyclyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cyclischen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro,Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylamino-carbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C -Cg-alkenyl, C 2 -Cg-alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -Cg-Cycloalky- _ loxy, heterocyclyl, heterocyclyloxy, 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, Ammocarbonyl , Aminothiocarbonyl , Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl , Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl, C3-Cg-Cycloalkyl , Ci-Cg-Alkoxy , Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxycarbonyl , Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-Alkyl - amino, Ci-Cg-Alkylaminocarbonyl , Di-Ci-Cg-Alkyl- aminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-Ci-Cg-Alkylaminothiocarbonyl , C -Cg-Alkenyl , C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy,Hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy , Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl, 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 oder C(=NOR7) -An-R8;Arylthio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl, Arylsulfonyl , Hetaryl, Het- arylcarbonyl oder Hetarylsulfonyl , wobei dieseAryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, these being
Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Ammocarbonyl , Aminothiocarbonyl , Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl,Radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
Ci-Cg-Alkylcarbonyl , Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl, C -Cg-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxycarbonyl , Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-Alkyl - amino, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-Alkyl- aminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-Ci-Cg-Alkylaminothiocarbonyl , C -Cg-Alkenyl , C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C (=NOR7) -An-R8;Ci-Cg-alkylcarbonyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C-Cg-cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cg-alkylthio, Ci Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C -Cg-alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 7 ) -A n -R 8 ;
Wasserstoff , 23Hydrogen, 23
Ci-Cg-Alkyl, C2-Cg-Alkenyl, C -Cg-Alkmyl, wobei die Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto, Am o, Carboxyl,Ci-Cg-alkyl, C 2 -Cg-alkenyl, C -Cg-alkmyl, where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, Am o Carboxyl
Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkylammocarbonyl , Dι-Cι-Cg-alkylammo- carbonyl , Ci-Cg-Alkylammothiocarbonyl , Dι-Cι-Cg-alkylammothiocarbonyl, Ci-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , Ci-Cg-Alkoxy, Cι~Cg-Ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkylammocarbonyl, Dι-Cι-Cg-alkylammocarbonyl, Ci-Cg-alkylammothiocarbonyl, Dι-Cι-Cg-alkylammothiocarbonyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Cι ~ Cg-
Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Cι~Cg-Alkyl- thio, Cι~C -Alkylammo, Dι-Cι-Cg-alkylammo, C2-Cg-Alkenyloxy, C3-Cg-Cycloalkyl, C3-Cg-Cycloalky- loxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryl - oxy, Aryl-Cι~C4-alkoxy, Arylthio, Aryl-Cι~C -alkyl - thio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C -alkoxy, Hetarylthio, Hetaryl-Cι-C -alkylthιo, wobei die cyclischen Reste ihrerseits partiell oder vollständig halogeniert sein können und/oder em bis drei der folgenden Gruppen tragen können: Cyano, Nitro,Haloalkoxy, Ci-Cg-alkoxycarbonyl, Cι ~ Cg-alkyl-thio, Cι ~ C -alkylammo, Dι-Cι-Cg-alkylammo, C 2 -Cg-alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -Cg-cycloalky - loxy, heterocyclyl, heterocyclyloxy, aryl, aryl - oxy, aryl-Cι ~ C 4 -alkoxy, arylthio, aryl-Cι ~ C -alkyl - thio, hetaryl, hetaryloxy, hetaryl-Cι-C -alkoxy, hetarylthio, hetaryl- -CC alkylthio, where the cyclic radicals can in turn be partially or completely halogenated and / or can carry up to three of the following groups: cyano, nitro,
Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkylsulfoxyl , C3Cg-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Haloalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cg-Alkylsulfoxyl, C 3 Cg-Cycloalkyl, Ci-Cg-Alkoxy, Ci Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-
Alkylammo, Dι-Cι-Cg-alkylammo, Ci-Cg-Alkylammo- carbonyl , Dι-Cι-Cg-alkylammocarbonyl , Ci-Cg-Alkyl- ammothiocarbonyl , Dι-Cι-Cg-alkylammothιocarbonyl , C2-Cg-Alkenyl, C -Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy,Alkylammo, Dι-Cι-Cg-alkylammo, Ci-Cg-alkylammocarbonyl, Dι-Cι-Cg-alkylammocarbonyl, Ci-Cg-alkyl ammothiocarbonyl, Dι-Cι-Cg-alkylammothιocarbonyl, C 2 -Cg-alkenyl, C -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy,
Hetarylthio und C (=N0R7) -An-R8 ;Hetarylthio and C (= N0R 7 ) -A n -R 8 ;
C3-Cg-Cycloalkyl, C3 -C -Cycloalkenyl , Heterocyclyl, Aryl, Hetaryl, wobei die cyclischen Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen kön¬ nen: Cyano, Nitro, Hydroxy, Mercapto, Ammo, Carboxyl, Ammocarbonyl, Ammothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkyl - sulfonyl, Ci-Cg-Alkylsulfoxyl , C3-Cg-Cycloalkyl , C3 -CG-cycloalkyl, C 3 -C cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or NEN carry one to three of the following groups Kgs ¬: cyano, nitro, hydroxy, mercapto, Ammo, carboxyl, ammocarbonyl, ammothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkyl-sulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl,
Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkoxy- carbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylammo, Dι-Cι-Cg-alkylammo , Ci-Cg-Alkylammocarbonyl , Dι-Cι-Cg-alkylammocarbonyl , Cι-Cg-Alkylammothιo- carbonyl, Dι-Cι-Cg-alkylammothιocarbonyl, 24Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxy-carbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylammo, Dι-Cι-Cg-alkylammo, Ci-Cg-alkylammocarbonyl, Dι-Cι- Cg-alkylammocarbonyl, Cι-Cg-alkylammothιocarbonyl, Dι-Cι-Cg-alkylammothιocarbonyl, 24
C -Cg-Alkenyl , C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;C -Cg alkenyl, C 2 -Cg alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
wobeiin which
für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cg-Alkyl trägt;represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Cg-alkyl;
n 0 oder 1 bedeutet ;n represents 0 or 1;
R7 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
mindestens eine Verbindung der Formeln II bis Vat least one compound of the formulas II to V
I II )I II)
Figure imgf000026_0001
OMe
Figure imgf000026_0001
OMe
Figure imgf000026_0002
: ιιi)
Figure imgf000026_0002
: ιιi)
!iv)! iv)
OMeOMe
Figure imgf000027_0001
Figure imgf000027_0001
(V)(V)
Figure imgf000027_0002
Figure imgf000027_0002
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
Fungizide Mischung nach Anspruch 1, welche m zwei Teilen konditioniert ist, wobei der eine Teil die Verbindung I in einem festen oder flussigen Trager enthalt und der andere Teil mindestens eine der Verbindungen II bis V einem festen oder flüssigen Trager enthalt.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 at least one of the compounds II to V containing a solid or liquid carrier.
Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schutzenden Materialien, Pflanzen, Samen, Boden, Flachen 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 V gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander erfolgen kann.Process for combating harmful fungi, characterized in that the fungi, their habitat or the materials, plants, seeds, soil, areas or spaces to be protected against fungal attack are treated with a fungicidal mixture according to one of Claims 1 to 2, the application of the Compound I and at least one of the compounds II to V can be carried out simultaneously, that is together or separately, or in succession.
Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Boden, Flachen, Materialien oder Räume mit 0,005 bis 1 kg/ha einer Verbindung I gemäß Anspruch 1 behandelt.Process according to Claim 3, characterized in that the harmful fungi, their habitat or the plants, seeds, soil, areas, materials or spaces to be kept free by them are treated with 0.005 to 1 kg / ha of a compound I according to Claim 1.
Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Boden, Flachen, Materialien oder 26A method according to claim 3, characterized in that the harmful fungi, their habitat or the plants, seeds, soil, surfaces, materials or 26
Räume mit 0.01 bis 1 kg/ha mindestens einer der Verbindungen II bis V gemäß Anspruch 1 behandelt. Spaces treated with 0.01 to 1 kg / ha of at least one of the compounds II to V according to claim 1.
PCT/EP1999/001909 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins WO1999048367A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2000537433A JP2002507552A (en) 1998-03-24 1999-03-22 Tris (oxime ether) derivative and other strobilurin based fungicide mixtures
CA002323598A CA2323598A1 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
AU34168/99A AU3416899A (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
EP99915684A EP1065930A1 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
BR9909001-5A BR9909001A (en) 1998-03-24 1999-03-22 Mixture for crop protection, and, process for the control of harmful fungi
IL13816899A IL138168A0 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19812764.2 1998-03-24
DE19812764 1998-03-24

Publications (1)

Publication Number Publication Date
WO1999048367A1 true WO1999048367A1 (en) 1999-09-30

Family

ID=7862023

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/001909 WO1999048367A1 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins

Country Status (12)

Country Link
EP (1) EP1065930A1 (en)
JP (1) JP2002507552A (en)
KR (1) KR100557363B1 (en)
CN (1) CN1149924C (en)
AU (1) AU3416899A (en)
BR (1) BR9909001A (en)
CA (1) CA2323598A1 (en)
CO (1) CO5090844A1 (en)
ID (1) ID26019A (en)
IL (1) IL138168A0 (en)
TW (1) TW548078B (en)
WO (1) WO1999048367A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002049434A1 (en) * 2000-12-18 2002-06-27 Basf Aktiengesellschaft Fungicide mixtures based on oxime ether derivatives
WO2002056685A2 (en) * 2001-01-18 2002-07-25 Basf Aktiengesellschaft Fungicidal mixtures
WO2004045283A2 (en) * 2002-11-15 2004-06-03 Basf Aktiengesellschaft Fungicidal mixtures for controlling rice pathogens
WO2006066810A2 (en) * 2004-12-20 2006-06-29 Basf Aktiengesellschaft Method for controlling mycoses in leguminous plants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0422401D0 (en) * 2004-10-08 2004-11-10 Syngenta Participations Ag Fungicidal compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0616771A1 (en) * 1993-03-26 1994-09-28 BASF Aktiengesellschaft Fungicidal mixture
EP0648417A1 (en) * 1993-09-24 1995-04-19 BASF Aktiengesellschaft Fungicidal mixtures
JPH07330512A (en) * 1994-06-07 1995-12-19 Sumitomo Chem Co Ltd Fungicidal composition
WO1997006679A1 (en) * 1995-08-17 1997-02-27 Basf Aktiengesellschaft Fungicidal mixtures
WO1997011606A1 (en) * 1995-09-25 1997-04-03 Basf Aktiengesellschaft Combatting parasitic fungi with a combination of an active agent inhibiting respiration in the cytochrome complex iii and of fenazaquine
WO1997015552A1 (en) * 1995-10-23 1997-05-01 Basf Aktiengesellschaft Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0616771A1 (en) * 1993-03-26 1994-09-28 BASF Aktiengesellschaft Fungicidal mixture
EP0648417A1 (en) * 1993-09-24 1995-04-19 BASF Aktiengesellschaft Fungicidal mixtures
JPH07330512A (en) * 1994-06-07 1995-12-19 Sumitomo Chem Co Ltd Fungicidal composition
WO1997006679A1 (en) * 1995-08-17 1997-02-27 Basf Aktiengesellschaft Fungicidal mixtures
WO1997011606A1 (en) * 1995-09-25 1997-04-03 Basf Aktiengesellschaft Combatting parasitic fungi with a combination of an active agent inhibiting respiration in the cytochrome complex iii and of fenazaquine
WO1997015552A1 (en) * 1995-10-23 1997-05-01 Basf Aktiengesellschaft Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 096, no. 004 30 April 1996 (1996-04-30) *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002049434A1 (en) * 2000-12-18 2002-06-27 Basf Aktiengesellschaft Fungicide mixtures based on oxime ether derivatives
CN100345482C (en) * 2000-12-18 2007-10-31 巴斯福股份公司 Fangicide mixtures based on oxime ether derivatives
WO2002056685A2 (en) * 2001-01-18 2002-07-25 Basf Aktiengesellschaft Fungicidal mixtures
WO2002056685A3 (en) * 2001-01-18 2002-09-12 Basf Ag Fungicidal mixtures
WO2004045283A2 (en) * 2002-11-15 2004-06-03 Basf Aktiengesellschaft Fungicidal mixtures for controlling rice pathogens
WO2004045283A3 (en) * 2002-11-15 2004-07-29 Basf Ag Fungicidal mixtures for controlling rice pathogens
EA007898B1 (en) * 2002-11-15 2007-02-27 Басф Акциенгезельшафт Fungicidal mixtures
KR100706733B1 (en) * 2002-11-15 2007-04-13 바스프 악티엔게젤샤프트 Fungicidal Mixtures
WO2006066810A2 (en) * 2004-12-20 2006-06-29 Basf Aktiengesellschaft Method for controlling mycoses in leguminous plants
WO2006066810A3 (en) * 2004-12-20 2006-09-21 Basf Ag Method for controlling mycoses in leguminous plants
EA012612B1 (en) * 2004-12-20 2009-10-30 Басф Акциенгезельшафт Method for controlling mycosis in leguminous plants

Also Published As

Publication number Publication date
IL138168A0 (en) 2001-10-31
JP2002507552A (en) 2002-03-12
KR100557363B1 (en) 2006-03-10
KR20010042148A (en) 2001-05-25
CA2323598A1 (en) 1999-09-30
CN1294487A (en) 2001-05-09
CN1149924C (en) 2004-05-19
ID26019A (en) 2000-11-16
AU3416899A (en) 1999-10-18
BR9909001A (en) 2000-11-28
TW548078B (en) 2003-08-21
EP1065930A1 (en) 2001-01-10
CO5090844A1 (en) 2001-10-30

Similar Documents

Publication Publication Date Title
EP1039807A1 (en) Fungicide mixtures based on pyridine amides and chlorothalonil
EP1039800B1 (en) Fungicide mixtures based on pyridine carboxamide compounds
WO1999048365A1 (en) Fungicide mixtures based on triple oxime ether derivatives and rhizoctonia fungicides
WO1999048367A1 (en) Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
WO1999048368A1 (en) Fungicide mixtures based on triple oxime ether derivatives and rice fungicides
WO1999048370A1 (en) Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
WO1999048369A1 (en) Fungicide mixtures based on triple oxime ether derivatives and additional fungicides
EP1139749A1 (en) Fungicide mixtures which are based on derivatives of morpholine or piperidine and derivatives of oxime ether
MXPA00008479A (en) Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
MXPA00008748A (en) Fungicide mixtures based on triple oxime ether derivatives and rice fungicides
MXPA00009122A (en) Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
WO2002049434A9 (en) Fungicide mixtures based on oxime ether derivatives
MXPA00008486A (en) Fungicide mixtures based on triple oxime ether derivatives and rhizoctonia fungicides
MXPA00008720A (en) Fungicide mixtures based on triple oxime ether derivatives and additional fungicides

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 99804315.X

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AL AU BG BR BY CA CN CZ GE HU ID IL IN JP KR KZ LT LV MK MX NO NZ PL RO RU SG SI SK TR UA US ZA

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1999915684

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 138168

Country of ref document: IL

Ref document number: PA/a/2000/008479

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 506725

Country of ref document: NZ

WWE Wipo information: entry into national phase

Ref document number: 09623682

Country of ref document: US

ENP Entry into the national phase

Ref document number: 2323598

Country of ref document: CA

Ref document number: 2323598

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 34168/99

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 200005089

Country of ref document: ZA

WWE Wipo information: entry into national phase

Ref document number: 1020007010554

Country of ref document: KR

Ref document number: 1020007010553

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: IN/PCT/2000/514/CHE

Country of ref document: IN

WWP Wipo information: published in national office

Ref document number: 1999915684

Country of ref document: EP

WWR Wipo information: refused in national office

Ref document number: 1020007010554

Country of ref document: KR

WWW Wipo information: withdrawn in national office

Ref document number: 1020007010554

Country of ref document: KR

WWP Wipo information: published in national office

Ref document number: 1020007010553

Country of ref document: KR

NENP Non-entry into the national phase

Ref country code: CA

WWW Wipo information: withdrawn in national office

Ref document number: 1999915684

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1020007010553

Country of ref document: KR