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WO1996032015A1 - Synergistic fungicide compositions made of quinoline derivatives and cytochrom b/c inhibitors - Google Patents

Synergistic fungicide compositions made of quinoline derivatives and cytochrom b/c inhibitors Download PDF

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Publication number
WO1996032015A1
WO1996032015A1 PCT/EP1996/001298 EP9601298W WO9632015A1 WO 1996032015 A1 WO1996032015 A1 WO 1996032015A1 EP 9601298 W EP9601298 W EP 9601298W WO 9632015 A1 WO9632015 A1 WO 9632015A1
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WIPO (PCT)
Prior art keywords
alkoxy
alkyl
formula
hydroxy
alkylthio
Prior art date
Application number
PCT/EP1996/001298
Other languages
German (de)
French (fr)
Inventor
Harald Köhle
Eberhard Ammermann
Herbert Bayer
Oliver Wagner
Franz Röhl
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 EP96908131A priority Critical patent/EP0820232A1/en
Priority to AU51486/96A priority patent/AU5148696A/en
Priority to KR1019970707096A priority patent/KR19980703696A/en
Priority to NZ304327A priority patent/NZ304327A/en
Priority to BR9604823A priority patent/BR9604823A/en
Priority to JP8530672A priority patent/JPH11503435A/en
Publication of WO1996032015A1 publication Critical patent/WO1996032015A1/en
Priority to MXPA/A/1997/007537A priority patent/MXPA97007537A/en

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action

Definitions

  • the present invention relates to a method for controlling harmful fungi and to suitable synergistic mixtures which, in addition to an active ingredient IA or IB which inhibits respiration on the cytochrome complex III, contains an active ingredient of the formula II.
  • m is an integer from 1 to 6, where the radicals R can be different if m is greater than 1;
  • Aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroaryl-C 1 -C 6 alkyl, heteroaryl-C 1 -C 6 alkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, where these groups can be partially or completely halogenated and / or can be halogenated can carry one to three of the following radicals: cyano, nitro, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or
  • R 1 is hydrogen, cyano, nitro, hydroxy, mercapto, amino,
  • C 3 -C 6 cycloalkyl aryl, aryl-C 1 -C 6 alkyl, aryl-C 1 -C 6 alkoxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroaryl-C 1 -C 6 -alkyl, heteroaryl- C 1 -C 6 alkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, where these groups can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, nitro, hydroxy, C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio.
  • Examples of such active ingredients are compounds of the formula IA or IB
  • Bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
  • C 1 -C 4 haloalkyl C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio
  • Y C- or -N-
  • EP-A 472 224 EP-A 472 300, EP-A 474 042 EP-A 475 158,
  • EP-A 532 022 EP-A 532 126, EP-A 532 127 EP-A 535 980,
  • EP-A 582 902 EP-A 582 925, EP-A 583 806, EP-A 584 625,
  • the method according to the invention is probably based on the fact that the fungus uses a secondary pathway of alternative breathing when inhibiting breathing on the cytochrome complex III, so that there is no complete killing. This would mean that the active ingredients of the formula II are suitable for inhibiting alternative breathing.
  • the combination of the inhibition of both breathing via the cytochrome complex III and the alternative breathing could be responsible for the fact that the fungus is completely killed.
  • a more effective control of the harmful fungus is achieved by the combination of corresponding active ingredients according to the invention, since the combination of the active ingredients IA or IB and II reduces them
  • EP-A 515 901 EP-A 585 751
  • Hetarylethenylene generally and in particular correspond to the meanings described in the following publications:
  • EP-A 280 185, EP-A 378 755, EP-A 398 692, EP-A 402 246,
  • EP-A 474 042 EP-A 475 158, EP-A 477 631, EP-A 487 409,
  • EP-A 242 081 EP-A 256 667, EP-A 260 794, EP-A 278 595,
  • EP-A 280 185, EP-A 463 488, EP-A 501 901, EP-A 513 580,
  • EP-A 389 901 EP-A 409 369, EP-A 464 381, EP-A 471 261,
  • R a is hydrogen or C 1 -C 4 alkyl
  • R b is hydrogen, halogen or C 1 -C 4 alkyl
  • R 1 is hydrogen
  • R c is hydrogen, nitro, sulfoxyl, halogen, C 1 -C 4 alkyl,
  • R d is hydrogen;
  • R e is hydrogen, nitro or halogen;
  • R f is hydrogen, hydroxy, carboxyl, halogen, C 1 -C 4 alkyl,
  • Compounds IA or IB and II are distinguished by an excellent action against a broad spectrum, in particular of phytopathogenic fungi. They are partly systemically effective (i.e. when used for crop protection, they can be absorbed by the treated plant without loss of activity and possibly transported in the plant) and can therefore also be used as leaf and soil fungicides.
  • the compounds IA or IB and II can be applied simultaneously together or separately or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
  • the compounds IA or IB and II are usually in one
  • the application rates of the mixtures according to the invention are 0.015 to 10 kg / ha, preferably 0.1 to 7 kg / ha, in particular 0.2 to 3 kg / ha.
  • the application rates for the compounds IA and IB are 0.005 to 3 kg / ha, preferably 0.02 to 2 kg / ha, in particular 0.05 to 1 kg / ha.
  • the application rates for the compounds II are generally 0.05 to 10 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.2 to 2 kg / ha.
  • the joint or separate application of the compounds IA or IB and II or the mixtures of the compounds IA or IB and II is carried out by spraying or dusting the seeds, the plants or the soil before or after the Sowing the plants or before or after the plants germinate.
  • the fungicidal synersistic mixtures according to the invention or the compounds IA or IB and II can be used, 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, spreading agents or processed granules and applied 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 manner known per se, e.g. by adding solvents and / or carriers. Inert additives such as emulsifiers or dispersants are usually added to the formulations.
  • Phenolic, naphthalene and dibutylnaphthalenesulfonic acid as well as from Fatty acid, alkyl and alkyl aryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or
  • Granules e.g. coating, impregnation or homogeneous granules
  • a solid carrier e.g., a granule, a granule, a granule, a granule, a granule, a granule, a granule, a granule, a granule, a granule, a granules.
  • Mineral earths 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 and other solid carriers.
  • mineral earths 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 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds IA or IB or II or the hybrid of the compounds IA or IB and II.
  • the active compounds are used in a purity of 90% to 100%, preferably 95% to 100% (according to 1 H-NMR or HPLC spectrum).
  • the compounds IA or IB and II or the mixtures or the corresponding formulations are used by the harmful fungi, their habitat or the materials, plants, seeds, soils, areas or spaces to be protected against fungal attack with a fungicidally effective amount of the mixture or the compounds IA or IB and II treated separately. Thieves action can take place before or after the infestation by the harmful fungi.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Quinoline Compounds (AREA)

Abstract

A process for controlling harmful fungi is characterised in that the fungi, their biotope or materials, plants, seeds, ground, surfaces or rooms to be protected against fungi are treated separately or together, simultaneously or successively with an active substance (I) that inhibits the respiration of cytochrom complex III and with an active substance of formula (II), in which the indices and substituents have the following meanings: m is an integer from 1 to 6, whereas the rests R may differ from each other when m is larger than 1; R stands for hydrogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, sulfo, aminosulphonyl, halogen, alkyl, haydroxyalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, alkylthio, alkylamino, dialkylamino, alkylsuphonyl, alkylsulphoxyl, alkylsulphonyloxy, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonylamino, alkoxycarbonyl, alkoxycarbonylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, alkylaminosulphonyl, dialkylaminosulphonyl, alkenyl, alkenyloxy, alkenylcarbonyloxy, alkinyl and alkinyloxy, whereas these groups may be partially or completely halogenated; cycloalkyl, aryl arylalkyl, arylalkoxy, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroarylalkyl, heteroarylalkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, whereas these groups may be partially or completely halogenated and/or bear one to three of the following rests; cyano, nitro, hydroxy, alkyl, alkyl halide, alkoxy, alkoxy halide or alkylthio; R1 stands for hydrogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbornyl, sulfo, aminosulphonyl, halogen, alkyl, hydroxyalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, alkylthio, alkylamino, dialkylamino, alkylsulphonyl, alkylsulphoxyl, alkylsulphonyloxy, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonylamino, alkoxycarbonyl, alkoxycarbonylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, alkylaminosulphonyl, dialkylaminosulphonyl, alkenyl, alkenyloxy, alkenylcarbonyloxy, alkinyl and alkinyloxy, whereas these groups may be partially or completely halogenated; cycloalkyl, aryl, arylalkyl, arylalkoxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroarylalkyl, heteroarylalkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, whereas these groups may be partially or completely halogenated and/or bear one to three of the following rests: cyano, nitro, hydroxy, alkyl, alkyl halide, alkoxy, alkoxy halide or alkylthio. Also disclosed are appropriate mixtures therefor.

Description

SYNEGISTISCHE FUNGIZIDE ZUSAMMENSETZUNGEN AUS CHINOLINDERIVATEN UND CYTOCHROM b/c-INHIBITORS  SYNEGISTIC FUNGICIDAL COMPOSITIONS OF CHINOLINE DERIVATIVES AND CYTOCHROM b / c INHIBITORS
Beschreibung  description
Die vorliegende Erfindung betrifft ein Verfahren zur Bekämpfung von Schadpilzen sowie dafür geeignete synergistische Mischungen, welche neben einem Wirkstoff IA bzw. IB, der die Atmung am Cytochrom Komplex III hemmt, einem Wirkstoff der Formel II enthält. The present invention relates to a method for controlling harmful fungi and to suitable synergistic mixtures which, in addition to an active ingredient IA or IB which inhibits respiration on the cytochrome complex III, contains an active ingredient of the formula II.
Figure imgf000003_0001
in der der Index und die Substituenten die folgende Bedeutung haben: m eine ganze Zahl von 1 bis 6, wobei die Reste R verschieden sein können, wenn m größer als 1 ist;
Figure imgf000003_0001
in which the index and the substituents have the following meaning: m is an integer from 1 to 6, where the radicals R can be different if m is greater than 1;
R Wasserstoff, Cyano, Nitro, Hydroxy, Merkapto, Amino, R hydrogen, cyano, nitro, hydroxy, mercapto, amino,
Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Sulfo (SO3H), Aminosulfonyl, Halogen, Carboxyl, aminocarbonyl, aminothiocarbonyl, sulfo (SO 3 H), aminosulfonyl, halogen,
C1-C6-Alkyl, Hydroxy-C1-C6-alkyl, C1-C6-Alkoxy-C1-C6-alkyl,C 1 -C 6 alkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl,
C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C6-alkoxy, C1-C6-Alkylthio,C 1 -C 6 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio,
C1-C6-Alkylamino, Di- C1-C6-Alkylamino, C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C1-C6-Alkylsulfonyloxy, C1-C6-Alkylcarbonyl, C1-C6-Alkylcarbonyloxy, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonyl, C1-C6-Alkoxycarbonylamino, C1-C6-Alkylaminocarbonyl, Di-C1-C6-Alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-Alkylaminothiocarbonyl, C1-C6-Alkylaminosulfonyl, Di-C1-C6-Alkylaminosulfonyl, C2-C6-Alkenyl,C 1 -C 6 alkylamino, di- C 1 -C 6 alkylamino, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkylaminocarbonyl, di-C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 1 -C 6 alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, C 2 -C 6 alkenyl,
C2-C6-Alkenyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6-Alkinyl und C2-C6-Alkinyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können; C3-C6-Cycloalkyl, Aryl, Aryl-C1-C6-alkyl, Aryl- C1-C6-alkoxy,C 2 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyloxy, C 2 -C 6 alkynyl and C 2 -C 6 alkynyloxy, where these groups can be partially or completely halogenated; C 3 -C 6 cycloalkyl, aryl, aryl-C 1 -C 6 alkyl, aryl C 1 -C 6 alkoxy,
Aryloxy, Arylthio, Arylcarbonyl, Arylcarbonyloxy, Heteroaryl, Heteroaryl-C1-C6-alkyl, Heteroaryl-C1-C6-alkoxy, Heteroaryloxy, Heteroarylthio, Heteroarylcarbonyl und Heteroarylcarbonyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, C1-C4-Alkyl, C1-C4 -Halogenalkyl , C1-C4-Alkoxy, C1-C4-Halogenalkoxy oderAryloxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroaryl-C 1 -C 6 alkyl, heteroaryl-C 1 -C 6 alkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, where these groups can be partially or completely halogenated and / or can be halogenated can carry one to three of the following radicals: cyano, nitro, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or
C1-C4 -Alkylthio ; C 1 -C 4 alkylthio;
R1 Wasserstoff, Cyano, Nitro, Hydroxy, Merkapto, Amino, R 1 is hydrogen, cyano, nitro, hydroxy, mercapto, amino,
Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Sulfo (SO3H), Aminosulfonyl. Halogen, Carboxyl, aminocarbonyl, aminothiocarbonyl, sulfo (SO 3 H), aminosulfonyl. Halogen,
C1-C6-Alkyl, Hydroxy-C1-C6-alkyl, C1-C6-Alkoxy-C1-C6-alkyl,C 1 -C 6 alkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl,
C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C6-alkoxy, C1-C6-Alkylthio,C 1 -C 6 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylthio,
C1-C6-Alkylamino, Di-C1-C6-Alkylamino, C1-C6-Alkylsulfonyl,C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 1 -C 6 alkylsulfonyl,
C1-C6-Alkylsulfoxyl, C1-C6 -Alkylsulfonyloxy, C1-C6-Alkylcarbonyl, C1-C6-Alkylcarbonyloxy, C1-C6-Alkylcarbonylamino.C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonylamino.
C1-C6-Alkoxycarbonyl, C1-C6-Alkoxycarbonylamino, C1-C6-Alkylaminocarbonyl, Di-C1-C6-Alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-Alkylaminothiocarbonyl, C1-C6-Alkylaminosulfonyl, Di-C1-C6-Alkylaminosulfonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6-Alkinyl und C2-C6-Alkinyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können; C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkylaminocarbonyl, di-C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di-C 1 -C 6 - Alkylaminothiocarbonyl, C 1 -C 6 alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyloxy, C 2 -C 6 - Alkynyl and C 2 -C 6 -alkynyloxy, where these groups can be partially or completely halogenated;
C3-C6-Cycloalkyl, Aryl, Aryl-C1-C6-alkyl, Aryl-C1-C6-alkoxy, Arylthio, Arylcarbonyl, Arylcarbonyloxy, Heteroaryl, Heteroaryl-C1-C6-alkyl, Heteroaryl- C1-C6-alkoxy, Heteroaryloxy, Heteroarylthio, Heteroarylcarbonyl und Heteroarylcarbonyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkylthio. Es ist aus der Literatur bekannt, daß Wirkstoffe, die den Cytochrom bei Komplex (Cytochrom Kompex III) hemmen, als Fungizide eingesetzt werden können [vgl. U. Brandt, U. Haase, H. Schägger, G. von Jagow: "Spezifität und Wirkmechanismus der Strobilurine", Dechema-Monographie Bd. 129, 27-38, VCH Verlagsgesellschaft C 3 -C 6 cycloalkyl, aryl, aryl-C 1 -C 6 alkyl, aryl-C 1 -C 6 alkoxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroaryl-C 1 -C 6 -alkyl, heteroaryl- C 1 -C 6 alkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, where these groups can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, nitro, hydroxy, C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio. It is known from the literature that active ingredients which inhibit the cytochrome in complex (cytochrome Kompex III) can be used as fungicides [cf. U. Brandt, U. Haase, H. Schägger, G. von Jagow: "Specificity and Mechanism of Action of Strobilurins", Dechema-Monographie Vol. 129, 27-38, VCH Verlagsgesellschaft
Weinheim, 1993; J.M. Clough: Natural Product Reports, 1993, 565-574; F. Röhl, H. Sauter: Biochem. Soc. Trans. 22, 635 Weinheim, 1993; J.M. Clough: Natural Product Reports, 1993, 565-574; F. Röhl, H. Sauter: Biochem. Soc. Trans. 22, 635
(1993)1.  (1993) 1
Beispiele für solche Wirkstoffe sind Verbindungen der Formel IA oder IB Examples of such active ingredients are compounds of the formula IA or IB
Figure imgf000005_0001
Figure imgf000005_0001
in denen .... für eine Doppel- oder Einfachbindung steht und der Index und die Substituenten die folgende Bedeutung haben: R' -C[CO2CH3]=CHOCH3, -C [CO2CH3] =NOCH3, -C [CONHCH3] =NOCH3, in which .... stands for a double or single bond and the index and the substituents have the following meaning: R '-C [CO 2 CH 3 ] = CHOCH 3 , -C [CO 2 CH 3 ] = NOCH 3 , -C [CONHCH 3 ] = STILL 3 ,
-C[CO2CH3] =CHCH3, -C [CO2CH3] =CHCH2CH3, -C [COCH3] =NOCH3, -C [CO 2 CH 3 ] = CHCH 3 , -C [CO 2 CH 3 ] = CHCH 2 CH 3 , -C [COCH 3 ] = NOCH 3 ,
-C[COCH2CH3]=NOCH3, -N(OCH3) -CO2CH3, -N(CH3) -CO2CH3, -C [COCH 2 CH 3 ] = NOCH 3 , -N (OCH 3 ) -CO 2 CH 3 , -N (CH 3 ) -CO 2 CH 3 ,
-N(CH2CH3)-CO2CH3, R" ein C-organischer Rest, welcher direkt oder über eine Oxy-, Mercapto-, Amino-, oder Alkylaminogruppe gebunden ist, oder zusammen mit einer Gruppe X und dem Ring Q bzw. T, an den sie gebunden sind, ein ggf. subst. bicyclisches, partiell oder vollständig ungesättigtes System, welches neben Kohlenstoffringgliedern Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, -N (CH 2 CH 3 ) -CO 2 CH 3 , R "is a C-organic radical which is bonded directly or via an oxy, mercapto, amino or alkylamino group, or together with a group X and the ring Q or T, to which they are bound, an optionally subst. Bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
Rx -OC[CO2CH3]=CHOCH3, -OC [CO2CH3] =CHCH3, -OC [CO2CH3] =CHCH2CH3, -SC[CO2CH3]=CHOCH3, -SC [CO2CH3] =CHCH3, -SC [CO2CH3] =CHCH2CH3,R x -OC [CO 2 CH 3 ] = CHOCH 3 , -OC [CO 2 CH 3 ] = CHCH 3 , -OC [CO 2 CH 3 ] = CHCH 2 CH 3 , -SC [CO 2 CH 3 ] = CHOCH 3 , -SC [CO 2 CH 3 ] = CHCH 3 , -SC [CO 2 CH 3 ] = CHCH 2 CH 3 ,
-N (CH3) C [CO2CH3] =CHOCH3, -N (CH3) C [CO2CH3] =NOCH3, -N (CH 3 ) C [CO 2 CH 3 ] = CHOCH 3 , -N (CH 3 ) C [CO 2 CH 3 ] = NOCH 3 ,
-CH2C [CO2CH3] =CHOCH3, -CH2C [CO2CH3] =NOCH3, -CH 2 C [CO 2 CH 3 ] = CHOCH 3 , -CH 2 C [CO 2 CH 3 ] = NOCH 3 ,
-CH2C [CONHCH3] =NOCH3, Ry Sauerstoff, Schwefel, =CH- oder =N-, n 0, 1, 2 oder 3, wobei die Reste X verschieden sein können, wenn n > 1 ist; X Cyano, Nitro, Halogen, C1-C4-Alkyl, C1-C4-Halogenylkyl, -CH 2 C [CONHCH 3 ] = NOCH 3 , R y oxygen, sulfur, = CH- or = N-, n 0, 1, 2 or 3, where the radicals X can be different if n>1; X cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenylkyl,
C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio oder für den Fall, daß n > 1 ist, eine an zwei benachbarte C-Atome des Phenylrings gebundene C3-C5-Alkylen-, C3-C5-Alkenylen-, Oxy-C2-C4-alkylen-, Oxy-C1-C3-alkylenoxy-, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or, if n> 1, a C 3 -C 5 bonded to two adjacent C atoms of the phenyl ring Alkylene, C 3 -C 5 alkenylene, oxy-C 2 -C 4 alkylene, oxy-C 1 -C 3 alkyleneoxy,
Oxy-C2-C4-alkenylen-, Oxy-C2-C4-alkenylenoxy- oder Butadiendiylgruppe, wobei diese Ketten ihrerseits ein bis drei der folgenden Reste tragen können: Halogen, C1-C4-Alkyl, Oxy-C 2 -C 4 -alkenylene, oxy-C 2 -C 4 -alkenyleneoxy or butadienediyl group, these chains in turn one to three of the can carry the following radicals: halogen, C 1 -C 4 alkyl,
C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkylthio, Y =C- oder -N-, Q Phenyl, Pyrrolyl, Thienyl, Furyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Thiadiazolyl, Triazolyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio, Y = C- or -N-, Q phenyl, pyrrolyl, thienyl, furyl, Pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl,
Pyridinyl, 2-Pyridonyl, Pyrimidinyl und Triazinyl, T Phenyl, Oxazolyl, Thiazolyl, Thiadiazolyl, Oxadiazolyl,  Pyridinyl, 2-pyridonyl, pyrimidinyl and triazinyl, T phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl,
Pyridinyl, Pyrimidinyl und Triazinyl.  Pyridinyl, pyrimidinyl and triazinyl.
Derartige Wirkstoffe I (bzw. IA und IB) sind beispielsweise in den folgenden Schriften beschrieben: Such active ingredients I (or IA and IB) are described, for example, in the following documents:
EP-A 178 826, EP-A 203 606, EP-A 203 608 EP-A 206 523, EP-A 178 826, EP-A 203 606, EP-A 203 608 EP-A 206 523,
EP-A 212 859, EP-A 226 917, EP-A 229 974 EP-A 242 070,  EP-A 212 859, EP-A 226 917, EP-A 229 974 EP-A 242 070,
EP-A 242 081, EP-A 243 012, EP-A 243 014 EP-A 251 082,  EP-A 242 081, EP-A 243 012, EP-A 243 014 EP-A 251 082,
EP-A 253 213, EP-A 254 426, EP-A 256 667 EP-A 260 794, EP-A 253 213, EP-A 254 426, EP-A 256 667 EP-A 260 794,
EP-A 260 832, EP-A 267 734, EP-A 273 572 EP-A 274 825,  EP-A 260 832, EP-A 267 734, EP-A 273 572 EP-A 274 825,
EP-A 278 595, EP-A 280 185, EP-A 291 196 EP-A 299 694,  EP-A 278 595, EP-A 280 185, EP-A 291 196 EP-A 299 694,
EP-A 307 101, EP-A 307 103, EP-A 310 954 EP-A 312 221,  EP-A 307 101, EP-A 307 103, EP-A 310 954 EP-A 312 221,
EP-A 312 243, EP-A 329 011, EP-A 331 966 EP-A 335 519,  EP-A 312 243, EP-A 329 011, EP-A 331 966 EP-A 335 519,
EP-A 336 211, EP-A 337 211, EP-A 341 845 EP-A 350 691, EP-A 336 211, EP-A 337 211, EP-A 341 845 EP-A 350 691,
EP-A 354 571, EP-A 363 818, EP-A 370 629 EP-A 373 775,  EP-A 354 571, EP-A 363 818, EP-A 370 629 EP-A 373 775,
EP-A 374 811, EP-A 378 308, EP-A 378 755 EP-A 379 098,  EP-A 374 811, EP-A 378 308, EP-A 378 755 EP-A 379 098,
EP-A 382 375, EP-A 383 117, EP-A 384 211 EP-A 385 224,  EP-A 382 375, EP-A 383 117, EP-A 384 211 EP-A 385 224,
EP-A 385 357, EP-A 386 561, EP-A 386 681 EP-A 389 901,  EP-A 385 357, EP-A 386 561, EP-A 386 681 EP-A 389 901,
EP-A 391 451, EP-A 393 428, EP-A 393 861 EP-A 398 692, EP-A 391 451, EP-A 393 428, EP-A 393 861 EP-A 398 692,
EP-A 400 417, EP-A 402 246, EP-A 405 782 EP-A 407 873,  EP-A 400 417, EP-A 402 246, EP-A 405 782 EP-A 407 873,
EP-A 409 369, EP-A 414 153, EP-A 416 746 EP-A 420 091,  EP-A 409 369, EP-A 414 153, EP-A 416 746 EP-A 420 091,
EP-A 422 597, EP-A 426 460, EP-A 429 968 EP-A 430 471,  EP-A 422 597, EP-A 426 460, EP-A 429 968 EP-A 430 471,
EP-A 433 233, EP-A 433 899, EP-A 439 785 EP-A 459 285,  EP-A 433 233, EP-A 433 899, EP-A 439 785 EP-A 459 285,
EP-A 460 575, EP-A 463 488, EP-A 463 513 EP-A 464 381, EP-A 460 575, EP-A 463 488, EP-A 463 513 EP-A 464 381,
EP-A 468 684, EP-A 468 695, EP-A 468 775 EP-A 471 261,  EP-A 468 684, EP-A 468 695, EP-A 468 775 EP-A 471 261,
EP-A 472 224, EP-A 472 300, EP-A 474 042 EP-A 475 158,  EP-A 472 224, EP-A 472 300, EP-A 474 042 EP-A 475 158,
EP-A 477 631, EP-A 480 795, EP-A 483 851 EP-A 483 985,  EP-A 477 631, EP-A 480 795, EP-A 483 851 EP-A 483 985,
EP-A 487 409, EP-A 493 711, EP-A 498 188 EP-A 498 396,  EP-A 487 409, EP-A 493 711, EP-A 498 188 EP-A 498 396,
EP-A 499 823, EP-A 503 436, EP-A 508 901 EP-A 509 857, EP-A 499 823, EP-A 503 436, EP-A 508 901 EP-A 509 857,
EP-A 513 580, EP-A 515 901, EP-A 517 301 EP-A 528 245,  EP-A 513 580, EP-A 515 901, EP-A 517 301 EP-A 528 245,
EP-A 532 022, EP-A 532 126, EP-A 532 127 EP-A 535 980,  EP-A 532 022, EP-A 532 126, EP-A 532 127 EP-A 535 980,
EP-A 538 097, EP-A 544 587, EP-A 546 387 EP-A 548 650,  EP-A 538 097, EP-A 544 587, EP-A 546 387 EP-A 548 650,
EP-A 564 928, EP-A 566 455, EP-A 567 828 EP-A 571 326,  EP-A 564 928, EP-A 566 455, EP-A 567 828 EP-A 571 326,
EP-A 579 071, EP-A 579 124, EP-A 579 908 , EP-A 581 095, EP-A 579 071, EP-A 579 124, EP-A 579 908, EP-A 581 095,
EP-A 582 902, EP-A 582 925, EP-A 583 806 , EP-A 584 625,  EP-A 582 902, EP-A 582 925, EP-A 583 806, EP-A 584 625,
EP-A 585 751, EP-A 590 610, EP-A 596 254 WO-A 90/07, 493,WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A 92/21,653, WO-A 93/07,116, WO-A 93/08,180, WO-A 93/08,183, WO-A 93/15,046, WO-A 93/16,986, WO-A 94/00,436, WO-A 94/05,626, WO-A 94/08,948, WO-A 94/08,968, WO-A 94/10,159, WO-A 94/11,334, JP-A 02/121,970, JP-A 04/182,461, JP-A 05/201,946, EP-A 585 751, EP-A 590 610, EP-A 596 254 WO-A 90/07, 493, WO-A 92 / 13,830, WO-A 92 / 18,487, WO-A 92 / 18,494, WO-A 92 / 21,653, WO-A 93 / 07,116, WO-A 93 / 08,180 , WO-A 93 / 08,183, WO-A 93 / 15,046, WO-A 93 / 16,986, WO-A 94 / 00,436, WO-A 94 / 05,626, WO-A 94 / 08,948, WO-A 94 / 08,968, WO-A 94 / 10,159, WO-A 94 / 11,334, JP-A 02 / 121,970, JP-A 04 / 182,461, JP-A 05 / 201,946,
JP-A 05/201,980, JP-A 05/255,012, JP-A 05/294,948, JP-A 05 / 201,980, JP-A 05 / 255,012, JP-A 05 / 294,948,
JP-A 06/025,133, JP-A 06/025,142, JP-A 06/056,756, JP-A 06 / 025,133, JP-A 06 / 025,142, JP-A 06 / 056,756,
FR-A 2 670 781, FR-A 2 670 781,
GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 2 249 092. GB-A 2 253 624, GB-A 2 255 092, GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 2 249 092.GB-A 2 253 624, GB-A 2 255 092,
DE-A 39 05 911, DE Pat. Anm. 43 05 502.8,  DE-A 39 05 911, DE Pat. Note 43 05 502.8,
DE Pat. Anm. 43 10 143.7, DE Pat. Anm. 43 18 397.2, DE Pat. Anm. 43 34 709.6, DE Pat. Anm. 44 03 446.6, DE Pat. Anm. 44 03 447.4, DE Pat. Anm. 44 03 448.2, DE Pat. Anm. 44 10 424.3, DE Pat. Anm. 44 21 180.5, DE Pat. Anm. 44 21 182.1, DE Pat. Anm. 44 15 483.6, DE Pat. Anm. 44 23 615.8, DE Pat. Anm. 44 23 612.3 und DE Pat. Anm. 44 41 674.1.  DE Pat. Note 43 10 143.7, DE Pat. Note 43 18 397.2, DE Pat. Note 43 34 709.6, DE Pat. Note 44 03 446.6, DE Pat. Note 44 03 447.4, DE Pat. Note 44 03 448.2, DE Pat. Note 44 10 424.3, DE Pat. Note 44 21 180.5, DE Pat. Note 44 21 182.1, DE Pat. Note 44 15 483.6, DE Pat. Note 44 23 615.8, DE Pat. Note 44 23 612.3 and DE Pat. Note 44 41 674.1.
Bei der Anwendung dieser Wirkstoffe zeigt sich jedoch, daß ihre Wirkung nur vorübergehend ist, d.h. bereits nach einiger Zeit tritt erneuter Wachstum des Pilzes auf. However, the use of these active substances shows that their effect is only temporary, i.e. after a while the fungus grows again.
Des weiteren sind aus der Literatur Verbindungen II mit fungizider Wirkung bekannt [vgl. Monatshefte für Chemie, 125, 51 f. und 723 f. (1994); Farm Chemicals Handbook Vol. 79 (1993); The Agrochemicals Handbook, 2. Ed., Royal Society of Chemistry (1987)]. Die Herstellung dieser Verbindungen ist außerdem in Houben-Weyl, Vol. E7a, 290-491 beschrieben. Der vorliegenden Erfindung lag die Aufgabe zugrunde, die Nachteile bei der Anwendung der Verbindungen IA bzw. IB zu beheben. Demgemäß wurde gefunden, daß sich Schadpilze grundsätzlich besser, bekämpfen lassen, wenn man neben einem Wirkstoff IA bzw. IB, der die Atmung am Cytochrom Komplex III hemmt, einen weiteren Wirkstoff der Formel II anwendet. Furthermore, compounds II with fungicidal activity are known from the literature [cf. Monthly magazines for chemistry, 125, 51 f. and 723 f. (1994); Farm Chemicals Handbook Vol. 79 (1993); The Agrochemicals Handbook, 2nd Ed., Royal Society of Chemistry (1987)]. The preparation of these compounds is also described in Houben-Weyl, Vol. E7a, 290-491. The present invention was based on the object of eliminating the disadvantages when using the compounds IA and IB. Accordingly, it was found that harmful fungi can in principle be controlled better if, in addition to an active ingredient IA or IB, which inhibits respiration on the cytochrome complex III, another active ingredient of the formula II is used.
Das erfindungsgemäße Verfahren beruht wahrscheinlich darauf, daß der Pilz bei Hemmung der Atmung am Cytochrom Komplex III einen Nebenweg der alternativen Atmung benutzt, so daß keine völlige Abtötung auftritt. Das würde bedeuten, daß die Wirkstoffe der Formel II geeignet sind, eine alternative Atmung zu hemmen. Die Kombination der Hemmung sowohl der Atmung über den Cytochrom Komplex III als auch der alternativen Atmung könnte dafür verantwortlich sein, daß der Pilz vollständig abgetötet wird. Durch die erfindungsgemäße Kombination entsprechender Wirkstoffe wird eine effektivere Bekämpfung des Schadpilzes erreicht, da durch die Kombination der Wirkstoffe IA bzw. IB und II geringereThe method according to the invention is probably based on the fact that the fungus uses a secondary pathway of alternative breathing when inhibiting breathing on the cytochrome complex III, so that there is no complete killing. This would mean that the active ingredients of the formula II are suitable for inhibiting alternative breathing. The combination of the inhibition of both breathing via the cytochrome complex III and the alternative breathing could be responsible for the fact that the fungus is completely killed. A more effective control of the harmful fungus is achieved by the combination of corresponding active ingredients according to the invention, since the combination of the active ingredients IA or IB and II reduces them
Aufwandmengen an den Einzelwirkstoffen erforderlich sind (Synergismus). Application rates of the individual active ingredients are required (synergism).
Zur Hemmung der Atmung am Cytochrom Komplex III eignen sich im erfinderischen Verfahren grundsätzlich alle in den eingangs genannten Schriften beschriebenen Wirkstoffe, wobei insbesondere die in den dort gegebengen Beispielen genannten Verbindungen in Betracht zu ziehen sind. Von besonderer Bedeutung sind dabei Verbindungen IA und IB, in denen R" für eine der folgenden Gruppen steht: ggf. subst. Aryloxy, ggf. subst. Hetaryloxy, ggf. subst. Aryloxymethylen, ggf. subst. Hetaryloxymethylen, ggf. subst. Arylethenylen, ggf. subst. Hetarylethenylen, oder eine Gruppe In principle, all active substances described in the publications cited at the outset are suitable for inhibiting breathing on the cytochrome complex III, the compounds mentioned in the examples given there in particular being considered. Of particular importance are compounds IA and IB in which R "stands for one of the following groups: optionally substituted aryloxy, optionally substituted hetaryloxy, optionally substituted aryloxymethylene, optionally substituted hetaryloxymethylene, optionally substituted arylethenylene , optionally subst. hetarylethenylene, or a group
RαRβC=NOCH2- oder RγON=CRδCRε=NOCH2 wobei die Reste Rα, Rβ Rγ, Rδ und Rε im allgemeinen und im besonderen die in den folgenden Schriften beschriebenen Bedeutungen haben: R α R β C = NOCH 2 - or R γ ON = CR δ CR ε = NOCH 2, where the radicals R α , R β R γ , R δ and R ε have in general and in particular the meanings described in the following documents :
EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575,
EP-A 463 488, EP-A 472 300, EP-A 498 188, EP-A 498 396,  EP-A 463 488, EP-A 472 300, EP-A 498 188, EP-A 498 396,
EP-A 515 901, EP-A 585 751, EP-A 515 901, EP-A 585 751,
WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18.494, WO-A 90 / 07,493, WO-A 92 / 13,830, WO-A 92 / 18,487, WO-A 92 / 18,494,
WO-A 93/15,046, WO-A 93/16,986, WO-A 94/08,948, WO-A 94/08.968.WO-A 93 / 15,046, WO-A 93 / 16,986, WO-A 94 / 08,948, WO-A 94 / 08.968.
JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948, JP-A 05 / 201,946, JP-A 05 / 255,012, JP-A 05 / 294,948,
JP-A 06/025,133, JP-A 06/025,142,  JP-A 06 / 025,133, JP-A 06 / 025,142,
DE Pat. Anm. 44 03 447.., DE Pat. Anm. 44 03 448.., DE Pat. Anm.DE Pat. Note 44 03 447 .., DE Pat. Note 44 03 448 .., DE Pat. Note
44 21 180.5 und DE Pat. Anm. 44 21 182.1; besonders bevorzugte Reste "ggf. subst . Aryloxy, ggf . subst . 44 21 180.5 and DE Pat. Note 44 21 182.1; particularly preferred radicals "optionally substituted aryloxy, optionally substituted.
Hetaryloxy" entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Bedeutungen: Hetaryloxy "generally and in particular correspond to the meanings described in the following documents:
EP-A 178 826, EP-A 242 070, EP-A 242 081, EP-A 253 213, EP-A 178 826, EP-A 242 070, EP-A 242 081, EP-A 253 213,
EP-A 254 426, EP-A 256 667, EP-A 260 794, EP-A 280 185,  EP-A 254 426, EP-A 256 667, EP-A 260 794, EP-A 280 185,
EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861,  EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861,
EP-A 398 692, EP-A 405 782, EP-A 430 471, EP-A 468 684, EP-A 398 692, EP-A 405 782, EP-A 430 471, EP-A 468 684,
EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188,  EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188,
EP-A 513 580, EP-A 515 901,  EP-A 513 580, EP-A 515 901,
WO-A 93/15,046, WO-A 94/10,159,  WO-A 93 / 15,046, WO-A 94 / 10,159,
GB-A 2 253 624,  GB-A 2 253 624,
JP-A 04/182,461 und JP-A 04 / 182,461 and
DE Pat. Anm. 44 23 612.3; Besonders bevorzugte Reste "ggf . subst . Aryloxymethylen, ggf . subst. Hetaryloxymethylen" entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Bedeutungen: DE Pat. Note 44 23 612.3; Particularly preferred radicals "optionally substituted aryloxymethylene, optionally substituted hetaryloxymethylene" generally and in particular correspond to the meanings described in the following documents:
EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426, EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426,
EP-A 278 595, EP-A 280 185, EP-A 299 694, EP-A 335 519, EP-A 278 595, EP-A 280 185, EP-A 299 694, EP-A 335 519,
EP-A 350 691, EP-A 363 818, EP-A 373 775, EP-A 378 308, EP-A 350 691, EP-A 363 818, EP-A 373 775, EP-A 378 308,
EP-A 385 224, EP-A 386 561, EP-A 398 692, EP-A 400 417, EP-A 385 224, EP-A 386 561, EP-A 398 692, EP-A 400 417,
EP-A 407 873, EP-A 472 224, EP-A 477 631, EP-A 498 188, EP-A 407 873, EP-A 472 224, EP-A 477 631, EP-A 498 188,
EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124,
WO-A 93/08,180, WO-A 93/15,046, WO-A 94/00,436, WO-A 93 / 08,180, WO-A 93 / 15,046, WO-A 94 / 00,436,
JP-A 04/182,461, JP-A 04 / 182,461,
DE Anm. Nr. 43 05 502.., DE Anm. Nr. 44 10 424.. und DE note no. 43 05 502 .., DE note no. 44 10 424 .. and
DE Pat. Anm. 44 15 483.6; besonders bevorzugte Reste "ggf . subs t . Arylethenylen, ggf. DE Pat. Note 44 15 483.6; particularly preferred residues ", if appropriate, subs. arylethenylene, if appropriate
subst . Hetarylethenylen" entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Bedeutungen: subst. Hetarylethenylene "generally and in particular correspond to the meanings described in the following publications:
EP-A 178 826, EP-A 203 606, EP-A 253 213, EP-A 254 426, EP-A 178 826, EP-A 203 606, EP-A 253 213, EP-A 254 426,
EP-A 280 185, EP-A 378 755, EP-A 398 692, EP-A 402 246, EP-A 280 185, EP-A 378 755, EP-A 398 692, EP-A 402 246,
EP-A 474 042, EP-A 475 158, EP-A 477 631, EP-A 487 409, EP-A 474 042, EP-A 475 158, EP-A 477 631, EP-A 487 409,
EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901,
EP-A 528 245, EP-A 544 587, EP-A 528 245, EP-A 544 587,
WO-A 93/15,046, WO-A 94/11,334,  WO-A 93 / 15,046, WO-A 94 / 11,334,
FR-A 2 670 781 und DE Pat. Anm. 44 23 615.8; besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -C[CO2CH3]=CHOCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: FR-A 2 670 781 and DE Pat. Note 44 23 615.8; Particularly preferred active compounds of the formula IA, in which R 'represents -C [CO 2 CH 3 ] = CHOCH 3 , generally and in particular correspond to the compounds described in the following documents:
EP-A 178 826, EP-A 203 606, EP-A 226 917, EP-A 242 070, EP-A 178 826, EP-A 203 606, EP-A 226 917, EP-A 242 070,
EP-A 242 081, EP-A 256 667, EP-A 260 794, EP-A 278 595,  EP-A 242 081, EP-A 256 667, EP-A 260 794, EP-A 278 595,
EP-A 299 694, EP-A 307 103, EP-A 335 519, EP-A 341 845, EP-A 299 694, EP-A 307 103, EP-A 335 519, EP-A 341 845,
EP-A 350 691, EP-A 370 629, EP-A 373 775, EP-A 378 308,  EP-A 350 691, EP-A 370 629, EP-A 373 775, EP-A 378 308,
EP-A 378 755, EP-A 382 375, EP-A 385 224, EP-A 386 561,  EP-A 378 755, EP-A 382 375, EP-A 385 224, EP-A 386 561,
EP-A 393 861, EP-A 402 246, EP-A 405 782, EP-A 407 873,  EP-A 393 861, EP-A 402 246, EP-A 405 782, EP-A 407 873,
EP-A 414 153, EP-A 426 460, EP-A 430 471, EP-A 463 488,  EP-A 414 153, EP-A 426 460, EP-A 430 471, EP-A 463 488,
EP-A 468 695, EP-A 472 224, EP-A 474 042, EP-A 475 158, EP-A 468 695, EP-A 472 224, EP-A 474 042, EP-A 475 158,
EP-A 483 985, EP-A 487 409, EP-A 515 901, EP-A 528 245,  EP-A 483 985, EP-A 487 409, EP-A 515 901, EP-A 528 245,
EP-A 544 587, EP-A 544 587,
WO-A 90/07,493, WO-A 92/18,487, WO-A 92/18,494, WO-A 93/08,180, WO-A 93/16,986, WO-A 94/00,463, WO-A 94/08,948, WO-A 94/08,968, WO-A 94/10,159, WO-A 94/11,334,  WO-A 90 / 07,493, WO-A 92 / 18,487, WO-A 92 / 18,494, WO-A 93 / 08,180, WO-A 93 / 16,986, WO-A 94 / 00,463, WO-A 94 / 08,948, WO -A 94 / 08,968, WO-A 94 / 10,159, WO-A 94 / 11,334,
FR-A 2 670 781 , FR-A 2 670 781,
JP-A 06/025,133, DE Anm. Nr. 44 03 447.., DE Anm. Nr. 44 10 424.. und DE Pat. Anm.JP-A 06 / 025,133, DE Note No. 44 03 447 .., DE Note No. 44 10 424 .. and DE Pat. Note
44 21 180.5; besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -C [CO2CH3] =NOCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: 44 21 180.5; Particularly preferred active compounds of the formula IA, in which R 'represents -C [CO 2 CH 3 ] = NOCH 3 , correspond in general and in particular to the compounds described in the following documents:
EP-A 253 213, EP-A 254 426, EP-A 299 694, EP-A 363 818, EP-A 253 213, EP-A 254 426, EP-A 299 694, EP-A 363 818,
EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 400 417, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 400 417,
EP-A 407 873, EP-A 460 575, EP-A 463 488, EP-A 468 684, EP-A 407 873, EP-A 460 575, EP-A 463 488, EP-A 468 684,
EP-A 472 300, EP-A 515 901, EP-A 472 300, EP-A 515 901,
WO-A 94/00,436, WO-A 94/08,948, WO-A 94/10,159, WO-A 94/11,334, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948,  WO-A 94 / 00,436, WO-A 94 / 08,948, WO-A 94 / 10,159, WO-A 94 / 11,334, JP-A 05 / 201,946, JP-A 05 / 255,012, JP-A 05 / 294,948,
DE Anm. Nr. 44 03 447.., DE Anm. Nr. 44 10 424.. und DE note no. 44 03 447 .., DE note no. 44 10 424 .. and
DE Pat. Anm. 44 21 180.5; besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -C[CONHCH3] =NOCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: DE Pat. Note 44 21 180.5; Particularly preferred active compounds of the formula IA, in which R 'is -C [CONHCH 3 ] = NOCH 3 , correspond in general and in particular to the compounds described in the following documents:
EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901. EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901.
EP-A 579 124, EP-A 585 751,  EP-A 579 124, EP-A 585 751,
WO-A 92/13,830, WO-A 93/08,180, WO-A 94/08,948, WO-A 94/10,159, WO-A 92 / 13,830, WO-A 93 / 08,180, WO-A 94 / 08,948, WO-A 94 / 10,159,
WO-A 94/11,334, WO-A 94 / 11,334,
GB-A 2 253 624, GB-A 2 253 624,
JP-A 04/182,461, JP-A 05/201,946, JP-A 05/255,012,  JP-A 04 / 182,461, JP-A 05 / 201,946, JP-A 05 / 255,012,
JP-A 05/294,948,  JP-A 05 / 294,948,
DE Anm. Nr. 43 05 502.., DE Anm. Nr. 44 03 448.., DE Anm. Nr. 44 DE Note No. 43 05 502 .., DE Note No. 44 03 448 .., DE Note No. 44
10 424.., DE Pat. Anm. Nr. 44 23 615.8 und DE Pat. Anm. 44 21 182.1; besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -C[CO2CH3]=CHCH3 oder -C [CO2CH3] =CHCH2CH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften be- schriebenen Verbindungen: 10 424 .., DE Pat. Note No. 44 23 615.8 and DE Pat. Note 44 21 182.1; Particularly preferred active compounds of the formula IA, in which R 'represents -C [CO 2 CH 3 ] = CHCH 3 or -C [CO 2 CH 3 ] = CHCH 2 CH 3 , correspond in general and in particular to those in the following documents described connections:
EP-A 280 185, EP-A 463 488, EP-A 501 901, EP-A 513 580, EP-A 280 185, EP-A 463 488, EP-A 501 901, EP-A 513 580,
EP-A 515 901, EP-A 515 901,
DE Anm. Nr. 44 03 447.., DE Anm. Nr. 44 10 424.., DE Pat. Anm. Nr. 44 21 180.5 und DE Pat. Anm. Nr. 44 15 483.6; besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -C[COCH3] =NOCH3 oder -C [COCH2CH3] =NOCH3 steht, entsprechen im allgemeinen und im besonderen den in der EP-A 498 188 beschriebenen Verbindungen; besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -N(OCH3)CO2CH3, -N(CH3)-CO2CH3 oder -N(CH2CH3)-CO2CH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: EP-A 498 396, WO-A 93/15,046, JP-A 06/025,142, JP-A 06/056,756. DE Pat. Anm. 44 23 612.3 und DE Pat. Anm. 44 41 674,1; DE Note No. 44 03 447 .., DE Note No. 44 10 424 .., DE Pat. Note No. 44 21 180.5 and DE Pat. Note No. 44 15 483.6; Particularly preferred active ingredients of the formula IA, in which R 'is -C [COCH 3 ] = NOCH 3 or -C [COCH 2 CH 3 ] = NOCH 3 , correspond in general and in particular to those described in EP-A 498 188 Links; particularly preferred active ingredients of the formula IA, in which R 'for -N (OCH 3 ) CO 2 CH 3 , -N (CH 3 ) -CO 2 CH 3 or -N (CH 2 CH 3 ) -CO 2 CH 3 correspond in general and in particular to those described in the following documents Compounds: EP-A 498 396, WO-A 93 / 15,046, JP-A 06 / 025,142, JP-A 06 / 056,756. DE Pat. Note 44 23 612.3 and DE Pat. Note 44 41 674.1;
Besonders bevorzugte Wirkstoffe der Formel IB, in denen Rx für -OC[CO2CH3] =CHOCH3, -OC [CO2CH3] =CHCH3, -OC[CO2CH3] =CHCH2CH3, Particularly preferred active compounds of the formula IB in which R x for -OC [CO 2 CH 3 ] = CHOCH 3 , -OC [CO 2 CH 3 ] = CHCH 3 , -OC [CO 2 CH 3 ] = CHCH 2 CH 3 ,
-SC[CO2CH3]=CHOCH3, -SC [CO2CH3] =CHCH3, -SC [CO2CH3] =CHCH2CH3, -SC [CO 2 CH 3 ] = CHOCH 3 , -SC [CO 2 CH 3 ] = CHCH 3 , -SC [CO 2 CH 3 ] = CHCH 2 CH 3 ,
-N(CH3)C[CO2CH3] =CHOCH3, -N (CH3) C [CO2CH3] =NOCH3, -N (CH 3 ) C [CO 2 CH 3 ] = CHOCH 3 , -N (CH 3 ) C [CO 2 CH 3 ] = NOCH 3 ,
-CH2C[CO2CH3]=CHOCH3, -CH2C[CO2CH3] =NOCH3 oder -CH2C[CONHCH3] =NOCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: -CH 2 C [CO 2 CH 3 ] = CHOCH 3 , -CH 2 C [CO 2 CH 3 ] = NOCH 3 or -CH 2 C [CONHCH 3 ] = NOCH 3 , generally and in particular correspond to those in the the following writings:
EP-A 212 859, EP-A 331 966, EP-A 383 117, EP-A 384 211, EP-A 212 859, EP-A 331 966, EP-A 383 117, EP-A 384 211,
EP-A 389 901, EP-A 409 369, EP-A 464 381, EP-A 471 261,  EP-A 389 901, EP-A 409 369, EP-A 464 381, EP-A 471 261,
EP-A 503 436, EP-A 546 387, EP-A 548 650, EP-A 579 908 und  EP-A 503 436, EP-A 546 387, EP-A 548 650, EP-A 579 908 and
EP-A 584 625. EP-A 584 625.
Beispiele für insbesondere geeignete Wirkstoffe I sind in den folgenden Tabellen zusammengestellt. Examples of particularly suitable active ingredients I are compiled in the following tables.
Tabelle 1.1A Table 1.1A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het)aryl- gruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHOCH 3 , n is 0, R "is optionally substituted. (Het) aryl-oxymethylene, the optionally subst. (het) aryl group has the following meaning
Figure imgf000011_0001
Tabelle 1. 1B
Figure imgf000011_0001
Table 1.1B
Verbindungen der Formel IA, in denen R' für -C(CO2CH3) =CHOCH3 steht, Q Phenyl bedeutet, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat Compounds of the formula IA, in which R 'is -C (CO 2 CH 3 ) = CHOCH 3 , Q is phenyl, n is 0, R "is optionally substituted (het) aryloxy, where the optionally subst. (het) aryl group has the following meaning
Figure imgf000012_0001
Figure imgf000012_0001
Tabelle 1.1C Verbindungen der Formel IA, in denen R' für -C (CO2CH3 ) =CHOCH3 steht, Q Phenyl bedeutet, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-ethenylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat Table 1.1C Compounds of the formula IA, in which R 'is -C (CO 2 CH 3 ) = CHOCH 3 , Q is phenyl, n is 0, R "is optionally substituted (het) aryl-ethenylene , where the optionally substituted (het) aryl group has the following meaning
Figure imgf000012_0002
Figure imgf000012_0002
Tabelle 1.1D  Table 1.1D
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRαRβ steht, wobei Rα und Rβ die folgende Bedeutung haben Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHOCH 3 , n is 0, R "is CH 2 ON = CR α R β , where R α and R β have the following meaning
Figure imgf000012_0003
Figure imgf000012_0003
Tabelle 1.1E  Table 1.1E
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRYCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung haben Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHOCH 3 , n is 0, R "is CH 2 ON = CRYCR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000013_0003
Figure imgf000013_0003
Tabelle 1.2A  Table 1.2A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally subst.
(Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat  (Het) aryl-oxymethylene, where the subst. (Het) aryl group has the following meaning
Figure imgf000013_0001
Figure imgf000013_0001
Tabelle 1.2B  Table 1.2B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally subst.
(Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat  (Het) aryl-oxy, where the subst. (Het) aryl group has the following meaning
Figure imgf000013_0002
Figure imgf000013_0002
Tabelle 1.2C  Table 1.2C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=NOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRαRβ steht, wobei Rα und Rβ die folgende Bedeutung haben
Figure imgf000014_0001
Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CR α R β , where R α and R β have the following meaning
Figure imgf000014_0001
Tabelle 1.2D  Table 1.2D
Verbindungen der Formel IA, in denen Q Phenyl bedeutet , R' für -C {CO2CH3 ) =NOCH3 steht , n den Wert 0 hat , R" für CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung haben Compounds of the formula IA where Q is phenyl, R 'is -C {CO 2 CH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000014_0002
Figure imgf000014_0002
Tabelle 1.3A  Table 1.3A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het)arylgruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl-oxymethylene, the subst. (Het) aryl group has the following meaning
Figure imgf000014_0003
Figure imgf000015_0001
Figure imgf000014_0003
Figure imgf000015_0001
Tabelle 1.3B  Table 1.3B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryloxy, the optionally subst. (Het) aryl group has the following meaning
Figure imgf000015_0002
Figure imgf000015_0002
Tabelle 1.3C  Table 1.3C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-ethenylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl-ethenylene, the optionally subst. (Het) aryl group has the following meaning
Figure imgf000015_0004
Figure imgf000015_0004
Tabelle 1.3D  Table 1.3D
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRαRβ steht, wobei Rα und Rβ die folgende Bedeutung haben Compounds of the formula IA in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CR α R β , where R α and R β have the following meaning
Figure imgf000015_0003
Tabelle 1. 3E
Figure imgf000015_0003
Table 1. 3E
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung haben Compounds of the formula IA in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000016_0002
Figure imgf000016_0002
Tabelle 1.4A Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHCH3 steht, n den Wert 0 hat, R" für ggf. subst. Table 1.4A Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHCH 3 , n is 0, R "is optionally subst.
(Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat  (Het) aryl-oxymethylene, where the subst. (Het) aryl group has the following meaning
Figure imgf000016_0001
Figure imgf000016_0001
Tabelle 1.4B  Table 1.4B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHCH3 steht, n den Wert 0 hat, R" für ggf. subst. Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHCH 3 , n is 0, R "is optionally subst.
(Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat
Figure imgf000017_0003
(Het) aryl-oxy, where the subst. (Het) aryl group has the following meaning
Figure imgf000017_0003
Tabelle 1 . 4C  Table 1 . 4C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHCH3 steht, n den Wert 0 hat, R" für CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung haben Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHCH 3 , n is 0, R "is CH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000017_0002
Figure imgf000017_0002
Tabelle 1.5A  Table 1.5A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHCH2CH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het)arylgruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHCH 2 CH 3 , n is 0, R "is optionally substituted (het) aryl-oxymethylene, where the optionally substituted (het) aryl group has the following meaning
Figure imgf000017_0001
Figure imgf000017_0001
Tabelle 1.5B  Table 1.5B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C (CO2CH3 ) =CHCH2CH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat
Figure imgf000018_0003
Compounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHCH 2 CH 3 , n is 0, R "is optionally substituted (het) aryloxy, where the optionally substituted (het) aryl group has the following meaning
Figure imgf000018_0003
Tabelle 1. 5C  Table 1.5C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CO2CH3)=CHCH2CH3 steht, n den Wert 0 hat, R" für Compounds of the formula IA where Q is phenyl, R 'is -C (CO 2 CH 3 ) = CHCH 2 CH 3 , n is 0, R "is
CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung haben CH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000018_0002
Figure imgf000018_0002
Tabelle 1.6A Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. Table 1.6A Compounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 3 ) = NOCH 3 , n is 0, R "is optionally subst.
(Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat  (Het) aryl-oxymethylene, where the subst. (Het) aryl group has the following meaning
Tabelle 1.6B  Table 1.6B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. Compounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 3 ) = NOCH 3 , n is 0, R "is optionally subst.
(Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat
Figure imgf000019_0004
(Het) aryl-oxy, where the subst. (Het) aryl group has the following meaning
Figure imgf000019_0004
Tabelle 1.7A  Table 1.7A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH2CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl-oxymethylene, the optionally subst. (het) aryl group has the following meaning
Figure imgf000019_0003
Figure imgf000019_0003
Tabelle 1.7B Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH2CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat Table 1.7B Compounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryloxy , where the optionally substituted (het) aryl group has the following meaning
Figure imgf000019_0001
Figure imgf000019_0001
Tabelle 1.8A  Table 1.8A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -N(OCH3)-CO2CH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het)aryl-oxymethylen steht, wobei die ggf. subst. (Het)aryll- gruppe die folgende Bedeutung hat Compounds of the formula IA, in which Q is phenyl, R 'is -N (OCH 3 ) -CO 2 CH 3 , n is 0, R "is optionally substituted. (Het) aryl-oxymethylene, the if necessary subst. (Het) aryll group has the following meaning
Figure imgf000019_0002
Figure imgf000020_0002
Figure imgf000019_0002
Figure imgf000020_0002
Tabelle 1.8B  Table 1.8B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -N(OCH3)-CO2CH3 steht, n den Wert 0 hat, R" für CH2ON=CRαRβ steht, wobei Rα und Rβ die folgende Bedeutung haben
Figure imgf000020_0003
Compounds of the formula IA, in which Q is phenyl, R 'is -N (OCH 3 ) -CO 2 CH 3 , n is 0, R "is CH 2 ON = CR α R β , where R α and Rβ have the following meaning
Figure imgf000020_0003
Im Hinblick auf ihre Verwendung in den erfindungsgemäßen  With regard to their use in the invention
Mischungen sind besonders Verbindungen der Formel II.1 bevorzugt,  Mixtures are particularly preferred compounds of the formula II.1,
Figure imgf000020_0001
Figure imgf000020_0001
in denen die Substituenten die folgende Bedeutung haben:  in which the substituents have the following meaning:
Ra Wasserstoff oder C1-C4-Alkyl; R a is hydrogen or C 1 -C 4 alkyl;
Rb Wasserstoff, Halogen oder C1-C4-Alkyl; R b is hydrogen, halogen or C 1 -C 4 alkyl;
R1 Wasserstoff; R 1 is hydrogen;
Rc Wasserstoff, Nitro, Sulfoxyl, Halogen, C1-C4-Alkyl, R c is hydrogen, nitro, sulfoxyl, halogen, C 1 -C 4 alkyl,
C1-C4-Alkylcarbonyl oder C1-C4-Alkylcarbonyloxy; C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkylcarbonyloxy;
Rd Wasserstoff; Re Wasserstoff, Nitro oder Halogen; R d is hydrogen; R e is hydrogen, nitro or halogen;
Rf Wasserstoff, Hydroxy, Carboxyl, Halogen, C1-C4-Alkyl, R f is hydrogen, hydroxy, carboxyl, halogen, C 1 -C 4 alkyl,
C1-C4-Alkoxy, C1-C4-Alkylcarbonyl, C1-C4-Alkylcarbonyloxy und C2-C4-Alkenylcarbonyloxy. C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkylcarbonyloxy and C 2 -C 4 alkenylcarbonyloxy.
Bevorzugt sind ferner Verbindungen II.1, bei denen mindestens einer der Reste R1 bzw. Ra bis Rf für Hydroxy steht. Besonders bevorzugt sind Verbindungen II.1, bei denen Rf Hydroxy bedeutet. Also preferred are compounds II.1 in which at least one of the radicals R 1 or R a to R f is hydroxy. Compounds II.1 in which R f is hydroxy are particularly preferred.
Beispiele für insbesondere geeignete Wirkstoffe der Formel II sind in der folgenden Tabelle zusammengestellt: Examples of particularly suitable active ingredients of the formula II are listed in the following table:
Figure imgf000022_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000023_0001
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe IA bzw. IB und II ein, denen man je nach Bedarf weitere Wirkstoffe gegen Schädlinge (z.B. Insekten, Spinntiere oder Nematoden) oder Schadpilze oder auch herbizide oder In the preparation of the mixtures, preference is given to using the pure active ingredients IA or IB and II, to which, depending on the need, further active ingredients against pests (e.g. insects, arachnids or nematodes) or harmful fungi or else herbicidal or
wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann. growth-regulating agents or fertilizers.
Die Mischungen der Verbindungen IA bzw. IB und II bzw. die gleichzeitige gemeinsame oder getrennte Verwendung der The mixtures of the compounds IA or IB and II or the simultaneous joint or separate use of the
Verbindungen IA bzw. IB und II zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum insbesondere von pflanzenpathogenen Pilzen aus. Sie sind z.T. systemisch wirksam (d.h. sie können bei der Anwendung zum Pflanzenschutz ohne Wirkungsverlust von der behandelten Pflanze aufgenommen und ggf. in der Pflanze transportiert werden) und können daher auch als Blatt- und Bodenfungizide eingesetzt werden.  Compounds IA or IB and II are distinguished by an excellent action against a broad spectrum, in particular of phytopathogenic fungi. They are partly systemically effective (i.e. when used for crop protection, they can be absorbed by the treated plant without loss of activity and possibly transported in the plant) and can therefore also be used as leaf and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen und Kürbisgewächse), Gerste, Gras, Hafer, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zuckerrohr und einer Vielzahl von Samen. They are particularly important for combating a large number of fungi on various crops such as cotton, vegetables (e.g. cucumber, beans and squashes), barley, grass, oats, 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, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle und Rasen, Dstilago-Arten an Getreide und Zuckerrohr, Venturia inaequalis 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, Puccinia species on cereals, Rhizoctonia species on cotton and lawn, Dstil on cereals and sugar cane, Venturia inaequalis
(Schorf) an Äpfeln, Helminthosporium-Arten an Getreide, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren und Reben, Cercospora arachidicola an Ernüssen, Pseudo- cercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Alternaria-Arten an Gemüse und Obst sowie Fusarium- und Verticillium-Arten.  (Scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries and vines, Cercospora arachidicola on nuts, Pseudo-cercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, phytophthora infestans and tomatoes, Plasmopara viticola on vines, Alternaria species on vegetables and fruit, and Fusarium and Verticillium species.
Sie sind außerdem im Materialschutz (z.B. Holzschutz) anwendbar, beispielsweise gegen Paecilomyces variotii. They can also be used in material protection (e.g. wood protection), for example against Paecilomyces variotii.
Die Verbindungen IA bzw. IB und II können gleichzeitig gemeinsam oder getrennt oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat. Die Verbindungen IA bzw. IB und II werden üblicherweise in einemThe compounds IA or IB and II can be applied simultaneously together or separately or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures. The compounds IA or IB and II are usually in one
Gewichtsverhältnis von 5 : 10 bis 1 : 50, vorzugsweise 2 : 1 bisWeight ratio of 5:10 to 1:50, preferably 2: 1 to
1 : 20, insbesondere 1 : 1 bis 1 : 10 (1:11) angewendet. Die Aufwandmengen der erfindungsgemäßen Mischungen liegen je nach der Art des gewünschten Effektes bei 0,015 bis 10 kg/ha, vorzugsweise 0,1 bis 7 kg/ha, insbesondere 0,2 bis 3 kg/ha. 1:20, in particular 1: 1 to 1:10 (1:11) applied. Depending on the type of effect desired, the application rates of the mixtures according to the invention are 0.015 to 10 kg / ha, preferably 0.1 to 7 kg / ha, in particular 0.2 to 3 kg / ha.
Die Aufwandmengen liegen dabei für die Verbindungen IA und IB bei 0,005 bis 3 kg/ha, vorzugsweise 0,02 bis 2 kg/ha, insbesondere 0,05 bis 1 kg/ha. The application rates for the compounds IA and IB are 0.005 to 3 kg / ha, preferably 0.02 to 2 kg / ha, in particular 0.05 to 1 kg / ha.
Die Aufwandmengen für die Verbindungen II liegen im allgemeinen bei 0,05 bis 10 kg/ha, vorzugsweise 0,1 bis 5 kg/ha, insbesondere 0,2 bis 2 kg/ha. The application rates for the compounds II are generally 0.05 to 10 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.2 to 2 kg / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,001 bis 0,1 g/kg Saatgut, vorzugsweise 0,002 bis 0,05 g/kg Saatgut, insbesondere 0,005 bis 0,5 g/kg Saatgut verwendet. In the case of seed treatment, application rates of mixture of 0.001 to 0.1 g / kg of seed, preferably 0.002 to 0.05 g / kg of seed, in particular 0.005 to 0.5 g / kg of seed, are generally used.
Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind erfolgt die gemeinsame oder getrennte Applikation der Verbindungen IA bzw. IB und II oder der Mischungen aus den Verbindungen IA bzw. IB und II durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Keimen der Pflanzen. If pathogenic harmful fungi are to be combated for plants, the joint or separate application of the compounds IA or IB and II or the mixtures of the compounds IA or IB and II is carried out by spraying or dusting the seeds, the plants or the soil before or after the Sowing the plants or before or after the plants germinate.
Die erfindungsgemäßen fungiziden synersistischen Mischungen bzw. die Verbindungen IA bzw. IB und II können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Ganulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendugszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten. Die Formulierungen werden in an sich bekannter Weise hergestellt, z.B. durch Zugabe von Lösungsmitteln und/oder Trägerstoffen. Den Formulierungen werden üblicherweise inerte Zusatzstoffe wie Emulgiermittel oder Dispergiermittel beigemischt. Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali- und Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, The fungicidal synersistic mixtures according to the invention or the compounds IA or IB and II can be used, 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, spreading agents or processed granules and applied 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 manner known per se, e.g. by adding solvents and / or carriers. Inert additives such as emulsifiers or dispersants are usually added to the formulations. The alkali, alkaline earth and ammonium salts of aromatic sulfonic acids, e.g. Lignin-,
Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäure, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolether, Kondensationsprodukte von sulfoniertem Naphthalin und seinen Derivaten mit Form- aldehyd, Kondensationsprodukte des Naphthalins bzw. der Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acid, alkyl and alkyl aryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or
Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol oder Tributylphenylpolyglycolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkyl- ether oder Polyoxypropylen, Laurylalkoholpolyglycoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht. Pulver, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der Verbindungen IA bzw. IB und II oder der Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil or methylalkylene ether ethylene, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether, polyalkylene ethylenedilyl ether Powders, materials for spreading and dusts can be obtained by mixing or grinding the compounds IA or IB and II or the
Mischungen aus den Verbindungen IA bzw. IB und II mit einem festen Trägerstoff hergestellt werden. Granulate (z.B. Umhüllungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt. Mixtures of the compounds IA or IB and II are prepared with a solid carrier. 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, Kalzium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe. Mineral earths 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 and other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% einer der Verbindungen IA bzw. IB oder II oder der Mischling aus den Verbindungen IA bzw. IB und II. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach 1H-NMR- oder HPLC-Spectrum) eingesetzt. Die Verbindungen IA bzw. IB und II bzw. die Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, ihren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Böden, Flächen oder Räume mit einer fungizid wirksamen Menge der Mischung bzw. der Verbindungen IA bzw. IB und II bei getrennter Ausbringung, behandelt. Die Be handlung kann vor oder nach dem Befall durch die Schadpilze erfolgen. The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds IA or IB or II or the hybrid of the compounds IA or IB and II. The active compounds are used in a purity of 90% to 100%, preferably 95% to 100% (according to 1 H-NMR or HPLC spectrum). The compounds IA or IB and II or the mixtures or the corresponding formulations are used by the harmful fungi, their habitat or the materials, plants, seeds, soils, areas or spaces to be protected against fungal attack with a fungicidally effective amount of the mixture or the compounds IA or IB and II treated separately. Thieves action can take place before or after the infestation by the harmful fungi.
Die synergistische Wirkung der erfindungsgemäßen Mischungen ließ sich durch die folgenden Versuche zeigen:  The following experiments demonstrated the synergistic effect of the mixtures according to the invention:
Laborversuche: Laboratory tests:
Sporenkeimungstest: Spore germination test:
Suspensionen von Pilzsporen (Botrytis cinerea, 106 Sporen / ml) in Mikrotiterplatten wurden nach Zusatz von Testlösung 24 h bei 18ºC inkubiert. Nach 48h bzw. 72h wurde die Keimung unter dem Makro- skop durch Schätzung des Wachstums im Vergleich mit unbehandelten Kontrollen bewertet. Suspensions of fungal spores (Botrytis cinerea, 10 6 spores / ml) in microtiter plates were incubated at 18 ° C for 24 hours after the addition of test solution. After 48h and 72h, germination was assessed under the macro scope by estimating the growth in comparison with untreated controls.
Die Bewertung erfolgte in % im Verhältnis zur unbehandelten Kontrolle. The evaluation was made in% in relation to the untreated control.
Figure imgf000027_0001
Figure imgf000027_0001
a % Wirkung der Verbindung II  a% effect of compound II
b % Wirkung der Mischung von II mit 1 ppm der Verbindung I.2A-1 c % nach Colby berechneter Erwartungswert  b% Effect of the mixture of II with 1 ppm of the compound I.2A-1 c% expected value calculated according to Colby

Claims

Patentansprüche claims
1. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Boden, Flächen oder Räume gleichzeitig gemeinsam oder getrennt, oder nacheinander mit einem Wirkstoff I behandelt, der die Atmung am Cytochrom Komplex III hemmt und einem Wirkstoff der Formel II 1. A method 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 simultaneously or separately, or in succession with an active ingredient I which the Breathing on cytochrome complex III inhibits and an active ingredient of formula II
Figure imgf000028_0001
Figure imgf000028_0001
behandelt, in der der Index und die Substituenten die folgende Bedeutung haben: m eine ganze Zahl von 1 bis 6, wobei die Reste R verschieden sein können, wenn m größer als 1 ist;  treated in which the index and the substituents have the following meaning: m is an integer from 1 to 6, where the radicals R can be different if m is greater than 1;
R Wasserstoff, Cyano, Nitro, Hydroxy, Merkapto, Amino,  R hydrogen, cyano, nitro, hydroxy, mercapto, amino,
Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Sulfo, Aminosulfonyl, Halogen,  Carboxyl, aminocarbonyl, aminothiocarbonyl, sulfo, aminosulfonyl, halogen,
C1-C6-Alkyl, Hydroxy-C1-C6-alkyl, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C6-alkoxy,C 1 -C 6 alkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy- C 1 -C 6 alkoxy,
C1-C6-Alkylthio, C1-C6-Alkylamino, Di-C1-C6-Alkylamino,C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino,
C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C1-C6-Alkylsulfonyloxy, C1-C6-Alkylcarbonyl, C1-C6-Alkylcarbonyloxy, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkoxycarbonyl,
C1-C6-Alkoxycarbonylamino, C1-C6-Alkylaminocarbonyl, Di- C1-C6-Alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di- C1-C6-Alkylaminothiocarbonyl, C1-C6-Alkylaminosulfonyl, Di-C1-C6-Alkylaminosulfonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6-Alkinyl und C2-C6-Alkinyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können; C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkylaminocarbonyl, di- C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di- C 1 -C 6 alkylaminothiocarbonyl, C 1 -C 6 - Alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyloxy, C 2 -C 6 alkynyl and C 2 -C 6 - Alkynyloxy, where these groups can be partially or completely halogenated;
C3-C6-Cycloalkyl, Aryl, Aryl-C1-C6-alkyl, C 3 -C 6 cycloalkyl, aryl, aryl-C 1 -C 6 alkyl,
Aryl-C1-C6-alkoxy, Aryloxy, Arylthio, Arylcarbonyl, Arylcarbonyloxy, Heteroaryl, Heteroaryl-C1-C6-alkyl, Heteroaryl- C1-C6-alkoxy, Heteroaryloxy, Heteroarylthio, Heteroarylcarbonyl und Heteroarylcarbonyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen kön nen: Cyano, Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkylthio; R1 Wasserstoff, Cyano, Nitro, Hydroxy, Merkapto, Amino, Aryl-C 1 -C 6 -alkoxy, aryloxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroaryl-C 1 -C 6 -alkyl, heteroaryl- C 1 -C 6 -alkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, these being Groups can be partially or completely halogenated and / or can carry one to three of the following radicals Nene: cyano, nitro, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio; R 1 is hydrogen, cyano, nitro, hydroxy, mercapto, amino,
Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Sulfo, Aminosulfonyl, Halogen,  Carboxyl, aminocarbonyl, aminothiocarbonyl, sulfo, aminosulfonyl, halogen,
C1-C6-Alkyl, Hydroxy-C1-C6-alkyl, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C6-alkoxy,C 1 -C 6 alkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy- C 1 -C 6 alkoxy,
C1-C6-Alkylthio, C1-C6-Alkylamino, Di-C1-C6-Alkylamino,C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino,
C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C1-C6 -Alkylsulfonyloxy, C1-C6-Alkylcarbonyl, C1-C6-Alkylcarbonyloxy,C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy,
C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonyl, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkoxycarbonyl,
C1-C6-Alkoxycarbonylamino, C1-C6-Alkylaminocarbonyl, Di-C1-C6-Alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-Alkylaminothiocarbonyl, C1-C6-Alkylaminosulfonyl, Di-C1-C6-Alkylaminosulfonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6-Alkinyl und C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkylaminocarbonyl, di-C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 1 -C 6 - Alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyloxy, C 2 -C 6 alkynyl and
C2-C6-Alkinyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können; C 2 -C 6 alkynyloxy, where these groups can be partially or completely halogenated;
C3-C6-Cycloalkyl, Aryl, Aryl-C1-C6-alkyl, C 3 -C 6 cycloalkyl, aryl, aryl-C 1 -C 6 alkyl,
Aryl-C1-C6-alkoxy, Arylthio, Arylcarbonyl, Arylcarbonyloxy, Heteroaryl, Heteroaryl-C1-C6-alkyl, Heteroaryl-C1-C6-alkoxy, Heteroaryloxy, Heteroarylthio, Heteroarylcarbonyl und Heteroarylcarbonyloxy, wobei diese Gruppen partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkylthio. Aryl-C 1 -C 6 -alkoxy, arylthio, arylcarbonyl, arylcarbonyloxy, heteroaryl, heteroaryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkoxy, heteroaryloxy, heteroarylthio, heteroarylcarbonyl and heteroarylcarbonyloxy, these groups being partial or can be completely halogenated and / or can carry one to three of the following radicals: cyano, nitro, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 - C 4 haloalkoxy or C 1 -C 4 alkylthio.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man zur Hemmung der Atmung am Cytochrom Komplex III einen Wirkstoff der Formel IA oder IB 2. The method according to claim 1, characterized in that to inhibit breathing on the cytochrome complex III, an active ingredient of the formula IA or IB
Figure imgf000029_0001
verwendet, in denen .... für eine Doppel- oder Einfachbindung steht und der Index und die Substituenten die folgende Bedeutung haben: R' -C[CO2CH3]=CHOCH3, -C[CO2CH3]=NOCH3, -C[CONHCH3]=NOCH3,
Figure imgf000029_0001
used in which .... stands for a double or single bond and the index and the substituents have the following meaning: R '-C [CO 2 CH 3 ] = CHOCH 3 , -C [CO 2 CH 3 ] = NOCH 3 , -C [CONHCH 3 ] = STILL 3 ,
-C[CO2CH3]=CHCH3, -C[CO2CH3]=CHCH2CH3, -C[COCH3]=NOCH3, -C[COCH2CH3]=NOCH3, -N (OCH3)-CO2CH3, -N(CH3)-CO2CH3, -C [CO 2 CH 3 ] = CHCH 3 , -C [CO 2 CH 3 ] = CHCH 2 CH 3 , -C [COCH 3 ] = NOCH 3 , -C [COCH 2 CH 3 ] = NOCH 3 , -N (OCH 3 ) -CO 2 CH 3 , -N (CH 3 ) -CO 2 CH 3 ,
-N(CH2CH3)-CO2CH3, R" ein C-organischer Rest, welcher direkt oder über eine-N (CH 2 CH 3 ) -CO 2 CH 3 , R "is a C-organic radical which is directly or via a
Oxy-, Mercapto-, Amino-, oder Alkylaminogruppe gebunden ist, oder zusammen mit einer Gruppe X und dem Ring Q bzw. T, an den sie gebunden sind, ein ggf. subst. bicyclisches, partiell oder vollständig ungesättigtes System, welches neben Kohlenstoffringgliedern Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann, Rx -OC[CO2CH3]=CHOCH3, -OC [CO2CH3] =CHCH3, Oxy, mercapto, amino, or alkylamino group is bound, or together with a group X and the ring Q or T to which they are bound, an optionally subst. bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen, R x -OC [CO 2 CH 3 ] = CHOCH 3 , -OC [CO 2 CH 3 ] = CHCH 3 ,
-OC[CO2CH3]=CHCH2CH3, -SC[CO2CH3]=CHOCH3, -OC [CO 2 CH 3 ] = CHCH 2 CH 3 , -SC [CO 2 CH 3 ] = CHOCH 3 ,
-SC[CO2CH3]=CHCH3, -SC[CO2CH3]=CHCH2CH3, -SC [CO 2 CH 3 ] = CHCH 3 , -SC [CO 2 CH 3 ] = CHCH 2 CH 3 ,
-N(CH3)C[CO2CH3] =CHOCH3, -N(CH3)C[CO2CH3]=NOCH3, -N (CH 3 ) C [CO 2 CH 3 ] = CHOCH 3 , -N (CH 3 ) C [CO 2 CH 3 ] = NOCH 3 ,
-CH2C[CO2CH3] =CHOCH3, -CH2C [CO2CH3] =NOCH3, -CH 2 C [CO 2 CH 3 ] = CHOCH 3 , -CH 2 C [CO 2 CH 3 ] = NOCH 3 ,
-CH2C [CONHCH3] =NOCH3, -CH 2 C [CONHCH 3 ] = STILL 3 ,
Ry Sauerstoff, Schwefel, =CH- oder =N-, n 0, 1, 2 oder 3, wobei die Reste X verschieden sein können, wenn n > 1 ist; R y is oxygen, sulfur, = CH- or = N-, n 0, 1, 2 or 3, where the radicals X can be different if n>1;
X Cyano, Nitro, Halogen, C1-C4-Alkyl, C1-C4-Halogenylkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio oder für den Fall, daß n > 1 ist, eine an zwei benachbarte C- Atome des Phenylrings gebundene C3-C5-Alkylen-, X cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 halylyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or in the event that n is> 1, a C 3 -C 5 alkylene- bonded to two adjacent C atoms of the phenyl ring,
C3-C5-Alkenylen-, Oxy-C2-C4-alkylen- , Oxy-C1-C3-alkylenoxy- , Oxy-C2-C4-alkenylen- , Oxy-C2-C4-alkenylenoxy- oder Butadiendiylgruppe, wobei diese Ketten ihrerseits ein bis drei der folgenden Reste tragen können: Halogen, C 3 -C 5 alkenylene, oxy-C 2 -C 4 alkylene, oxy-C 1 -C 3 alkyleneoxy, oxy-C 2 -C 4 alkenylene, oxy-C 2 -C 4 - alkenyleneoxy or butadienediyl group, these chains in turn being able to carry one to three of the following radicals: halogen,
C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy,
C1-C4-Halogenalkoxy oder C1-C4-Alkylthio, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio,
Y -C- oder -N-, Q Phenyl, Pyrrolyl, Thienyl, Furyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, 2-Pyridonyl, Pyrimidinyl und Triazinyl, T Phenyl, Oxazolyl, Thiazolyl, Thiadiazolyl, Oxadiazolyl, Pyridinyl, Pyrimidinyl und Triazinyl. Y -C- or -N-, Q phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl and triazinyl, T phenyl, oxazolyl, thiazolyl, thiadiazolyl, pyridiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl, oxadiazolyl.
3. Zur Bekämpfung von Schadpilzen geeignete synergistische 3. Suitable for combating harmful fungi synergistic
Mischung, enthaltend einen festen oder flüssigen Trägerstoff, einen Wirkstoff der Formel IA gemäß Anspruch 2 und eine synergistische Menge eines Wirkstoffs der Formel II gemäß Anspruch 1.  Mixture comprising a solid or liquid carrier, an active ingredient of the formula IA according to claim 2 and a synergistic amount of an active ingredient of the formula II according to claim 1.
4. Zur Bekämpfung von Schadpilzen geeignete synergistische 4. Suitable for combating harmful fungi synergistic
Mischung, enthaltend einen festen oder flüssigen Trägerstoff, einen Wirkstoff der Formel IB gemäß Anspruch 2 und eine synergistische Menge eines Wirkstoffs der Formel II gemäß Anspruch 1.  Mixture comprising a solid or liquid carrier, an active ingredient of the formula IB according to claim 2 and a synergistic amount of an active ingredient of the formula II according to claim 1.
5. Verwendung der Verbindungen IA oder IB gemäß Anspruch 2 zur Herstellung eines zur Bekämpfung von Schadpilzen geeigneten Mittels gemäß Anspruch 3 oder 4. 5. Use of the compounds IA or IB according to claim 2 for the preparation of a suitable agent for controlling harmful fungi according to claim 3 or 4.
6. Verwendung der Verbindungen II gemäß Anspruch 1 zur Herstellung eines zur Bekämpfung von Schadpilzen geeigneten Mittels gemäß Anspruch 3 oder 4. 6. Use of the compounds II according to claim 1 for the preparation of a suitable agent for controlling harmful fungi according to claim 3 or 4.
7. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man zur Hemmung der Atmung am Cytochrom Komplex III einen Wirkstoff der Formel IA gemäß Anspruch 2 verwendet. 7. The method according to claim 1, characterized in that an active ingredient of the formula IA according to claim 2 is used to inhibit breathing on the cytochrome complex III.
8. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man zur Hemmung der Atmung am Cytochrom Komplex III einen Wirkstoff der Formel IB gemäß Anspruch 2 verwendet. 8. The method according to claim 1, characterized in that an active ingredient of the formula IB according to claim 2 is used to inhibit breathing on the cytochrome complex III.
9. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Boden, Flächen oder Räume gleichzeitig gemeinsam oder getrennt, oder nacheinander mit einem Wirkstoff behandelt, der die Atmung am Cytochrom Komplex III hemmt und mit einem weiteren Wirkstoff behandelt, der die alternative Atmung hemmt. 9. A method of 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 simultaneously or separately, or in succession with an active ingredient which respiratory inhibits on cytochrome complex III and treated with another active ingredient that inhibits alternative breathing.
PCT/EP1996/001298 1995-04-08 1996-03-25 Synergistic fungicide compositions made of quinoline derivatives and cytochrom b/c inhibitors WO1996032015A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP96908131A EP0820232A1 (en) 1995-04-08 1996-03-25 Synergistic fungicide compositions made of quinoline derivatives and cytochrom b/c inhibitors
AU51486/96A AU5148696A (en) 1995-04-08 1996-03-25 Synergistic fungicide compositions made of quinoline derivat ives and cytochrom b/c inhibitors
KR1019970707096A KR19980703696A (en) 1995-04-08 1996-03-25 Synergistic Fungicide Compositions Prepared with Quinoline Derivatives and Cytochrome B / C Inhibitors
NZ304327A NZ304327A (en) 1995-04-08 1996-03-25 Synergistic fungicidal compositions containing a quinoline derivative and a cytochrom b/c inhibitor
BR9604823A BR9604823A (en) 1995-04-08 1996-03-25 Process to control harmful funggs and fungal pests synergistic mixture suitable to control fungal pests and use of compounds
JP8530672A JPH11503435A (en) 1995-04-08 1996-03-25 How to control harmful fungi
MXPA/A/1997/007537A MXPA97007537A (en) 1995-04-08 1997-10-01 Procedure to combat fungi noci

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DE19513404.4 1995-04-08
DE19513404 1995-04-08

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AR (1) AR001514A1 (en)
AU (1) AU5148696A (en)
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CA (1) CA2215514A1 (en)
HU (1) HUP9801630A2 (en)
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998041094A1 (en) * 1997-03-14 1998-09-24 Basf Aktiengesellschaft Fungicide mixture
US6093732A (en) * 1997-12-22 2000-07-25 Pharmacia & Upjohn Company 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
US6252080B1 (en) 1996-09-10 2001-06-26 Pharmacia & Upjohn Company 8-hydroxy-7-substituted quinolines as anti-viral agents
WO2002049438A3 (en) * 2000-12-18 2003-08-21 Basf Ag Carbamate-based fungicidal mixtures
US7432281B2 (en) 2003-10-07 2008-10-07 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US7576099B2 (en) 2005-02-28 2009-08-18 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
WO2011080266A1 (en) 2009-12-29 2011-07-07 Polichem S.A. New secondary 8-hydroxyquinoline-7-carboxamide derivatives.
WO2011080264A1 (en) 2009-12-29 2011-07-07 Polichem S.A. New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof
CN112608275A (en) * 2020-12-29 2021-04-06 兰州大学 Application of 2, 8-bis (trifluoromethyl) -4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110156678A (en) * 2019-05-27 2019-08-23 兰州大学 Use of a derivative modified at the 4-position of 2,8-bis(trifluoromethyl)quinolines in the prevention and treatment of plant diseases

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098486A1 (en) * 1982-07-06 1984-01-18 BASF Aktiengesellschaft Quinoline derivatives, method for their preparation, microbicides containing them, and their use in combating fungi
EP0531837A1 (en) * 1991-09-12 1993-03-17 BASF Aktiengesellschaft Fungicidal mixtures
US5240940A (en) * 1988-01-29 1993-08-31 Dowelanco Quinoline and cinnoline fungicide compositions
EP0630570A2 (en) * 1993-06-25 1994-12-28 Bayer Ag Fungicidal combinations of active agents
DE4422776A1 (en) * 1993-07-02 1995-01-12 Ciba Geigy Ag microbicides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098486A1 (en) * 1982-07-06 1984-01-18 BASF Aktiengesellschaft Quinoline derivatives, method for their preparation, microbicides containing them, and their use in combating fungi
US5240940A (en) * 1988-01-29 1993-08-31 Dowelanco Quinoline and cinnoline fungicide compositions
EP0531837A1 (en) * 1991-09-12 1993-03-17 BASF Aktiengesellschaft Fungicidal mixtures
EP0630570A2 (en) * 1993-06-25 1994-12-28 Bayer Ag Fungicidal combinations of active agents
DE4422776A1 (en) * 1993-07-02 1995-01-12 Ciba Geigy Ag microbicides

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 88, no. 9, 27 February 1978, Columbus, Ohio, US; abstract no. 59278s, H. BERMANN, H. LYR, E. KLUGE & G. RITTER: "Studies on the mode of action of tridemorph." page 122; column 2; XP002009733 *
H. LYR & C. POLTER (EDS.): "Systemfungiz., Int. Symp. 1974", 1975, AKAD.-VERLAG, BERLIN (DDR) *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6252080B1 (en) 1996-09-10 2001-06-26 Pharmacia & Upjohn Company 8-hydroxy-7-substituted quinolines as anti-viral agents
US6310211B1 (en) 1996-09-10 2001-10-30 Pharmacia & Upjohn Company 8-hydroxy-7-substituted quinolines as anti-viral agents
US6500842B1 (en) 1996-09-10 2002-12-31 Pharmacia & Upjohn Company 8-hydroxy-7-substituted quinolines as anti-viral agents
WO1998041094A1 (en) * 1997-03-14 1998-09-24 Basf Aktiengesellschaft Fungicide mixture
US6093732A (en) * 1997-12-22 2000-07-25 Pharmacia & Upjohn Company 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents
US7368414B2 (en) 2000-12-18 2008-05-06 Basf Aktiengesellschaft Fungicidal mixtures
WO2002049438A3 (en) * 2000-12-18 2003-08-21 Basf Ag Carbamate-based fungicidal mixtures
US7432281B2 (en) 2003-10-07 2008-10-07 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
US7576099B2 (en) 2005-02-28 2009-08-18 Renovis, Inc. Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same
WO2011080266A1 (en) 2009-12-29 2011-07-07 Polichem S.A. New secondary 8-hydroxyquinoline-7-carboxamide derivatives.
WO2011080264A1 (en) 2009-12-29 2011-07-07 Polichem S.A. New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof
EP2345641A1 (en) 2009-12-29 2011-07-20 Polichem S.A. New secondary 8-hydroxyquinoline-7-carboxamide derivatives
EP2345643A1 (en) 2009-12-29 2011-07-20 Polichem S.A. New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof
CN112608275A (en) * 2020-12-29 2021-04-06 兰州大学 Application of 2, 8-bis (trifluoromethyl) -4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases

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IL117785A0 (en) 1996-08-04
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HUP9801630A2 (en) 1998-11-30
KR19980703696A (en) 1998-12-05
ZA962709B (en) 1997-10-06
CN1180995A (en) 1998-05-06
AR001514A1 (en) 1997-10-22
EP0820232A1 (en) 1998-01-28
AU5148696A (en) 1996-10-30
CA2215514A1 (en) 1996-10-17

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