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WO1999048367A1 - Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines - Google Patents

Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines Download PDF

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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
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WIPO (PCT)
Prior art keywords
alkyl
aryl
alkoxy
hetaryl
cycloalkyl
Prior art date
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PCT/EP1999/001909
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German (de)
English (en)
Inventor
Klaus Schelberger
Thomas Grote
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Original Assignee
Basf Aktiengesellschaft
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Filing date
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Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to EP99915684A priority Critical patent/EP1065930A1/fr
Priority to CA002323598A priority patent/CA2323598A1/fr
Priority to IL13816899A priority patent/IL138168A0/xx
Priority to BR9909001-5A priority patent/BR9909001A/pt
Priority to AU34168/99A priority patent/AU3416899A/en
Priority to JP2000537433A priority patent/JP2002507552A/ja
Publication of WO1999048367A1 publication Critical patent/WO1999048367A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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

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  • 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

L'invention concerne des mélanges fongicides contenant comme constituants actifs (a) des dérivés d'acide phénylacétique de la formule (I), dans laquelle les substituants et l'indice ont la signification indiquée dans la description, ainsi que leurs sels, et (b) au moins un composé des formules (II) à (IV) dans des quantités produisant un effet synergique.
PCT/EP1999/001909 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines WO1999048367A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP99915684A EP1065930A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines
CA002323598A CA2323598A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines
IL13816899A IL138168A0 (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
BR9909001-5A BR9909001A (pt) 1998-03-24 1999-03-22 Mistura para proteção de cultivo, e, processo para o controle de fungos prejudiciais
AU34168/99A AU3416899A (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurins
JP2000537433A JP2002507552A (ja) 1998-03-24 1999-03-22 トリス（オキシムエーテル）誘導体及び他のストロビルリンを基礎とする殺菌剤混合物

Applications Claiming Priority (2)

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

Publications (1)

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

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PCT/EP1999/001909 WO1999048367A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines

Country Status (12)

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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002049434A1 (fr) * 2000-12-18 2002-06-27 Basf Aktiengesellschaft Melanges fongicides a base de derives d'oxymethers
WO2002056685A3 (fr) * 2001-01-18 2002-09-12 Basf Ag Melanges fongicides
WO2004045283A3 (fr) * 2002-11-15 2004-07-29 Basf Ag Melanges fongicides servant a lutter contre des agents pathogenes du riz
WO2006066810A3 (fr) * 2004-12-20 2006-09-21 Basf Ag Procede pour lutter contre les mycoses chez les legumineuses

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 (fr) * 1993-03-26 1994-09-28 BASF Aktiengesellschaft Mélange fongicide
EP0648417A1 (fr) * 1993-09-24 1995-04-19 BASF Aktiengesellschaft Mélanges fongicides
JPH07330512A (ja) * 1994-06-07 1995-12-19 Sumitomo Chem Co Ltd 殺菌剤組成物
WO1997006679A1 (fr) * 1995-08-17 1997-02-27 Basf Aktiengesellschaft Melanges fongicides
WO1997011606A1 (fr) * 1995-09-25 1997-04-03 Basf Aktiengesellschaft Lutte contre des champignons nuisibles grace a l'association de la fenazaquine avec un principe actif inhibant la respiration au niveau du complexe cytochrome iii
WO1997015552A1 (fr) * 1995-10-23 1997-05-01 Basf Aktiengesellschaft Derives d'acide phenylacetique, procede et intermediaires utilises pour leur production et agents les contenant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0616771A1 (fr) * 1993-03-26 1994-09-28 BASF Aktiengesellschaft Mélange fongicide
EP0648417A1 (fr) * 1993-09-24 1995-04-19 BASF Aktiengesellschaft Mélanges fongicides
JPH07330512A (ja) * 1994-06-07 1995-12-19 Sumitomo Chem Co Ltd 殺菌剤組成物
WO1997006679A1 (fr) * 1995-08-17 1997-02-27 Basf Aktiengesellschaft Melanges fongicides
WO1997011606A1 (fr) * 1995-09-25 1997-04-03 Basf Aktiengesellschaft Lutte contre des champignons nuisibles grace a l'association de la fenazaquine avec un principe actif inhibant la respiration au niveau du complexe cytochrome iii
WO1997015552A1 (fr) * 1995-10-23 1997-05-01 Basf Aktiengesellschaft Derives d'acide phenylacetique, procede et intermediaires utilises pour leur production et agents les contenant

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 (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002049434A1 (fr) * 2000-12-18 2002-06-27 Basf Aktiengesellschaft Melanges fongicides a base de derives d'oxymethers
CN100345482C (zh) * 2000-12-18 2007-10-31 巴斯福股份公司 基于肟醚衍生物的杀真菌混合物
WO2002056685A3 (fr) * 2001-01-18 2002-09-12 Basf Ag Melanges fongicides
WO2004045283A3 (fr) * 2002-11-15 2004-07-29 Basf Ag Melanges fongicides servant a lutter contre des agents pathogenes du riz
EA007898B1 (ru) * 2002-11-15 2007-02-27 Басф Акциенгезельшафт Фунгицидные смеси
KR100706733B1 (ko) * 2002-11-15 2007-04-13 바스프 악티엔게젤샤프트 살진균성 혼합물
WO2006066810A3 (fr) * 2004-12-20 2006-09-21 Basf Ag Procede pour lutter contre les mycoses chez les legumineuses
EA012612B1 (ru) * 2004-12-20 2009-10-30 Басф Акциенгезельшафт Способ борьбы с грибковыми заболеваниями бобовых культур

Also Published As

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

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