+

WO1999048370A1 - Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance - Google Patents

Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance Download PDF

Info

Publication number
WO1999048370A1
WO1999048370A1 PCT/EP1999/001917 EP9901917W WO9948370A1 WO 1999048370 A1 WO1999048370 A1 WO 1999048370A1 EP 9901917 W EP9901917 W EP 9901917W WO 9948370 A1 WO9948370 A1 WO 9948370A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkylamino
alkylaminothiocarbonyl
hetaryl
aryl
Prior art date
Application number
PCT/EP1999/001917
Other languages
German (de)
English (en)
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 JP2000537436A priority Critical patent/JP4458668B2/ja
Priority to IL13812599A priority patent/IL138125A0/xx
Priority to AU33317/99A priority patent/AU3331799A/en
Priority to EP99914531A priority patent/EP1065929A1/fr
Priority to CA002323593A priority patent/CA2323593A1/fr
Priority to BR9909045-7A priority patent/BR9909045A/pt
Publication of WO1999048370A1 publication Critical patent/WO1999048370A1/fr

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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/56—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles

Definitions

  • the present invention relates to fungicidal mixtures for combating harmful fungi which
  • R ⁇ R independently of one another was sers tof f and -CC alkyl
  • n 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
  • R 3 is hydrogen, cyano, -CC alkyl, -C ⁇ C 4 haloalkyl, C 3 -C ⁇ cycloalkyl;
  • R 4 , R 6 are independently hydrogen
  • Ci-Cg-haloalkyl Ci-Cg-alkylcarbonyl, C ⁇ -Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg- Alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-C ⁇ -alkylamino, di-Ci-C ß - alkylammo, Ci-Cg-alkylammocarbonyl, di-Ci-Cg-alkylammocarbonyl, Ci-Cg-alkylammothiocarbonyl, D ⁇ - C ⁇ -C 6 - alkylammothiocarbonyl, C -Cg alkenyl, C 2 -C 6 alkenyl - oxy, benzyl, benzyloxy, aryl, aryloxy, he
  • Ci-C ⁇ -Alkla ino di-Ci-Cg-alkylamino, C 2 -C 6 -alkenyloxy, C 3 -Cg-cycloalkyl, C 3 -C 6 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C ⁇ -C 4 -alkoxy, arylthio, aryl -CC 4 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC 4 -alkyl-thio, the cyclic radicals being partially or can be completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, ammocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl,
  • Ci-Cg-alkylsulfonyl Ci-Cg-alkylsulfoxyl, C 3 C 6 -cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci Cg-alkylthio, C] _- Cg-alkylamino, di-C] .
  • Ci-Cg-alkylamino-carbonyl di-Ci-Cg-alkylaminocarbonyl
  • Ci-Cg-alkylamino-thiocarbonyl di-Ci-Cg-alkylaminothiocarbonyl
  • C 3 -C ß- cycloalkyl C 3 - C_ -cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino , Carboxyl, Ammo ⁇ carbonyl, aminothiocarbonyl, halogen, Ci-C ß- alkyl, -C-C 6 -haloalkyl, -C-C 6 -alkylsulfonyl, C ⁇ -C 6 -alkyl sulfoxyl, C 3 -C 6 cycloalkyl, Ci -Cg-alkoxy, Ci-Cg-halo-alkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamin
  • A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or C ⁇ -Cg-alkyl; Represents 0 or 1;
  • R ' ' denotes hydrogen or Ci-C ⁇ -alkyl
  • the object of the present invention was to provide fungicidal mixtures which have a good fungicidal action which goes beyond the effectiveness of the mixture components alone, in particular against fungal diseases in rice.
  • EP 313,512 proposed common name: Acibenzolar (trade name: Bion®, Novartis)
  • probenazole (trade name Oryzamate®, Meiji Seika)
  • the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
  • the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example Ci-Cg-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dirnethylethyl , Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl , 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2 -Ethylbutyl
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloroethyl, trichloromethyl, fluoromethyl, difluoromethyl , Trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2 , 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl and pentafluoroethyl;
  • Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -Cg-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl , 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4th -Pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , l-methyl-3-buten
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, e.g. C -Cg-alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l- Methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l- Methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pent
  • Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclyllamino three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or ( Heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example 2-tetrahydrofranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazol-dinyl, 4 -isoxazolidinyl, 5 -isoxazolidinyl, 3 -isothiazolidinyl, 4-isothiazolidinyl
  • 1,3-dithian-2-yl 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3, -thiazin-2-yl, 4H-3, l-benzothiazin-2 -yl, 1, l-dioxo-2, 3,4,5-tetrahydrothien-2 -yl, 2H- 1, 4-benzothiazin-3 -yl, 2H- 1, 4 - Benzoxazin-3 -yl, 1,3-dihydro-oxazin-2-yl, 1, 3-dithian-2 -yl,
  • Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) are attached to the skeleton via a sulfonyl group (-SO 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
  • Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, also contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one
  • 5-membered heteroaryl containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms can contain atomic atoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl
  • 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or may contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1, 3-diene-1, 4-diyl group;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4 -Pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 10
  • 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta- 1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
  • Hetarylamino aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
  • R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
  • R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, optionally subst.
  • Aryl or hetaryl is.
  • R 5 for optionally subst.
  • Aryl or hetaryl is.
  • R 5 for optionally subst.
  • R 5 for optionally subst. Furyl, thienyl or pyrrolyl.
  • R 5 for optionally subst.
  • R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
  • R 5 is phenyl, which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, ammocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 -alkyl, C 1 -C 4 ⁇ haloalkyl, -C-C 4 alkoxy, -C-C 4 -haloalkoxy, C ⁇ -C 4 -alkylamino, di-C ⁇ -C - alkylamino, C ⁇ -C -alkylsulfonyl, C ⁇ -C-alkoxycarbonyl, C ⁇ -C -alkyl - Aminocarbonyl or Di-C ⁇ -C 4 alkylaminocarbonyl. 12
  • R 4 represents hydrogen, Ci-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -C -alkyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl.
  • R 4 is C 1 -C 6 -alkyl.
  • the compounds I contained in the mixtures according to the invention are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular against fungi from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.
  • Compound II is commercially available as a so-called resistance inducer (ie active ingredient immunizing against disease infestation), ie II does not have a direct fungicidal action, but instead induces resistance to harmful fungi in the treated plant.
  • Compound III is known as a fungicide. 13
  • the mixtures of the compounds I and at least one compound II to III can be used simultaneously, together or separately and are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes out. They are partly systemically effective and can therefore also be used as foliar and soil fungicides.
  • the mixtures according to the invention can be used with particular preference for controlling Py ⁇ cula ⁇ a oryzae.
  • the compounds I and at least one of the compounds II to III can be applied simultaneously, that is jointly or separately, or in succession, the sequence being 14 separate application generally has no effect on the success of the control.
  • the application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 kg / ha, depending on the type of effect desired .
  • the application rates for the compounds I are 0.01 to 2.5 kg / ha, preferably 0.05 to 2.5 kg / ha, in particular 0.1 to 1.0 kg / ha.
  • the application rates for the compounds II to III are accordingly 0.001 to 5 kg / ha, preferably 0.005 to 2 kg / ha, in particular 0.01 to 1.0 kg / ha.
  • application rates of mixture of 0.001 to 250 g / kg of seed preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg, are generally used.
  • the separate or joint application of the compounds I and at least one of the compounds II to III is carried out by spraying or dusting the seeds, the plants or the soil before or after the plants are sown or before or after the Emergence of plants.
  • the fungicidal synergistic mixtures according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing, dusting , Scattering or pouring can be applied.
  • the form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol), ketones (eg cyano 15 clohexanone), wet nurse (eg ethanolamm, dirnethylform amide) and water; Carriers such as natural gesture flour (eg kaolins, clays, talc, chalk) and synthetic starch flours (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignite sulfite waste liquors and methyl cellulose.
  • solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignm
  • Powder scattering and dusting agents can be prepared by mixing or grinding the compounds I and at least one of the compounds II to III or the mixture of the compounds I and at least one compound II to III with a solid carrier substance.
  • Granules e.g. coated granules, impregnated granules or homogeneous granules
  • a solid carrier usually produced by binding the active ingredient or ingredients to a solid carrier.
  • Mineral soils such as silica gel, silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers like ammonium sulfate,
  • Ammonium phosphate, ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to III or the mixture of 16 Veromditch I and at least one of the compounds II to III.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum).
  • the corresponding formulations are used in such a way that the harmful fungi, their habitat or the plants, seeds, soil, areas, materials or spaces to be kept free of them are mixed with a fungicidally effective amount of the mixture or of the compounds I and at least one of the compounds II to III for separate application.
  • the application can take place before or after the infestation by the harmful fungi.
  • V a mixture of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalm-1-sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite liquor and 7 parts by weight of powdered mixture, ground in a hammer mill Silica rule; A fine boil is obtained by finely distributing the mixture in water; VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dusting agent contains 3% by weight of active ingredient; 17
  • IX a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 88 parts by weight of a paraffinic mineral oil.
  • the active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
  • ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
  • the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
  • Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually
  • Example active ingredient conc. in ppm efficiency in% of unh. control

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (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)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (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 (III) dans des quantités produisant un effet synergique.
PCT/EP1999/001917 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance WO1999048370A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2000537436A JP4458668B2 (ja) 1998-03-24 1999-03-22 トリス（オキシムエーテル）誘導体及び抗誘導物質を基礎とする殺菌剤混合物
IL13812599A IL138125A0 (en) 1998-03-24 1999-03-22 Fungicidal mixtures based on tris (oxime ether) derivatives and resistance inducers
AU33317/99A AU3331799A (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
EP99914531A EP1065929A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance
CA002323593A CA2323593A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance
BR9909045-7A BR9909045A (pt) 1998-03-24 1999-03-22 Mistura para proteção de cultura, e, processo para controlar fungos nocivos

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19812761 1998-03-24
DE19812761.8 1998-03-24

Publications (1)

Publication Number Publication Date
WO1999048370A1 true WO1999048370A1 (fr) 1999-09-30

Family

ID=7862021

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/001917 WO1999048370A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance

Country Status (13)

Country Link
EP (1) EP1065929A1 (fr)
JP (1) JP4458668B2 (fr)
KR (1) KR100557366B1 (fr)
CN (1) CN1144523C (fr)
AR (1) AR018808A1 (fr)
AU (1) AU3331799A (fr)
BR (1) BR9909045A (fr)
CA (1) CA2323593A1 (fr)
CO (1) CO5080806A1 (fr)
IL (1) IL138125A0 (fr)
TW (1) TW520273B (fr)
WO (1) WO1999048370A1 (fr)
ZA (1) ZA200005090B (fr)

Cited By (3)

* 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
WO2005044002A2 (fr) 2003-11-07 2005-05-19 Basf Aktiengesellschaft Melanges contenant des strobilurines et des modulateurs de l'ethylene
WO2006066810A3 (fr) * 2004-12-20 2006-09-21 Basf Ag Procede pour lutter contre les mycoses chez les legumineuses

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10333373A1 (de) * 2003-07-23 2005-02-10 Bayer Ag Fungizide Wirkstoffkombinationen
CN106804158A (zh) * 2016-12-09 2017-06-09 河池市农业科学研究所 一种水稻稻瘟病防治方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07330512A (ja) * 1994-06-07 1995-12-19 Sumitomo Chem Co Ltd 殺菌剤組成物
WO1997001277A1 (fr) * 1995-06-29 1997-01-16 Novartis Ag Produits de protection des cultures
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
EP0779030A1 (fr) * 1995-12-11 1997-06-18 Novartis AG Compositions phytosanitaires

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07330512A (ja) * 1994-06-07 1995-12-19 Sumitomo Chem Co Ltd 殺菌剤組成物
WO1997001277A1 (fr) * 1995-06-29 1997-01-16 Novartis Ag Produits de protection des cultures
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
EP0779030A1 (fr) * 1995-12-11 1997-06-18 Novartis AG Compositions phytosanitaires

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
WO2005044002A2 (fr) 2003-11-07 2005-05-19 Basf Aktiengesellschaft Melanges contenant des strobilurines et des modulateurs de l'ethylene
WO2005044002A3 (fr) * 2003-11-07 2005-07-21 Basf Ag Melanges contenant des strobilurines et des modulateurs de l'ethylene
EA012044B1 (ru) * 2003-11-07 2009-08-28 Басф Се Смеси, содержащие стробилурины и модуляторы этилена
US8044084B2 (en) 2003-11-07 2011-10-25 Basf Se Mixture comprising strobilurins and ethylene modulators
KR101126807B1 (ko) 2003-11-07 2012-03-26 바스프 에스이 스트로빌루린 및 에틸렌 변조물질을 포함하는 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
CN1144523C (zh) 2004-04-07
TW520273B (en) 2003-02-11
CN1294490A (zh) 2001-05-09
AU3331799A (en) 1999-10-18
EP1065929A1 (fr) 2001-01-10
KR100557366B1 (ko) 2006-03-10
KR20010042146A (ko) 2001-05-25
IL138125A0 (en) 2001-10-31
CO5080806A1 (es) 2001-09-25
AR018808A1 (es) 2001-12-12
JP2002507555A (ja) 2002-03-12
BR9909045A (pt) 2000-12-05
CA2323593A1 (fr) 1999-09-30
ZA200005090B (en) 2001-10-26
JP4458668B2 (ja) 2010-04-28

Similar Documents

Publication Publication Date Title
EP1039805A2 (fr) Melanges fongicides a base de composes amide et de derives de pyridine
EP1039800A2 (fr) Melanges fongicides a base de composes amide et de derives de morpholine ou de piperidine
EP1065927A1 (fr) Melanges fongicides a base de derives d'oximether de diatomite et de fongicides de la rhizoctonie
EP1065929A1 (fr) Melanges fongicides a base de derives d'oximether de diatomite et d'inducteurs de resistance
AU737879B2 (en) Fungicidal mixtures based on tris (oxime ether) derivatives and rice fungicides
WO1999048367A1 (fr) Melanges fongicides a base de derives d'oximether de diatomite et d'autres strobilurines
WO1997035838A1 (fr) Amides d'acide carboxylique a action fongicide
EP1082010A1 (fr) Melanges fongicides a base de derives d'oximether de diatomite et d'autres fongicides
MXPA00009122A (en) Fungicide mixtures based on triple oxime ether derivatives and resistance inductors
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
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: 99804339.7

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: 1999914531

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 138125

Country of ref document: IL

WWE Wipo information: entry into national phase

Ref document number: 09623653

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 506835

Country of ref document: NZ

ENP Entry into the national phase

Ref document number: 2323593

Country of ref document: CA

Ref document number: 2323593

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PA/a/2000/009122

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 33317/99

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2000/05090

Country of ref document: ZA

Ref document number: 200005090

Country of ref document: ZA

WWE Wipo information: entry into national phase

Ref document number: 1020007010551

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: IN/PCT/2000/527/CHE

Country of ref document: IN

WWP Wipo information: published in national office

Ref document number: 1999914531

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1020007010551

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: 1999914531

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1020007010551

Country of ref document: KR

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载