EP0820232A1 - Compositions fongicides synergiques constituees de derives de quinoleine et en inhibiteurs de cytochrome b/c - Google Patents

Compositions fongicides synergiques constituees de derives de quinoleine et en inhibiteurs de cytochrome b/c

Info

Publication number
EP0820232A1
EP0820232A1 EP96908131A EP96908131A EP0820232A1 EP 0820232 A1 EP0820232 A1 EP 0820232A1 EP 96908131 A EP96908131 A EP 96908131A EP 96908131 A EP96908131 A EP 96908131A EP 0820232 A1 EP0820232 A1 EP 0820232A1
Authority
EP
European Patent Office
Prior art keywords
alkoxy
alkyl
formula
hydroxy
alkylthio
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96908131A
Other languages
German (de)
English (en)
Inventor
Harald Köhle
Eberhard Ammermann
Herbert Bayer
Oliver Wagner
Franz Röhl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 SE filed Critical BASF SE
Publication of EP0820232A1 publication Critical patent/EP0820232A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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.

Landscapes

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

Abstract

L'invention concerne un procédé de lutte contre les champignons nuisibles qui se caractérise en ce que les champignons, leur espace vital ou des matériaux, des plantes, des graines, le sol, des surfaces ou des salles à protéger contre les champignons sont traités en même temps ou successivement, ensemble ou séparément, avec un principe actif (I) qui inhibe la respiration du complexe de cytochrome III et avec un principe actif de la formule (II), dans laquelle les indices et les substituants ont la signification suivante: m vaut un nombre entier de 1 à 6, les restes R pouvant être différents les uns des autres lorsque m est supérieur à 1; R désigne hydrogène, cyano, nitro, hydroxy, mercapto, amino, carboxyle, aminocarbonyle, aminothiocarbonyle, sulfo, aminosulfonyle, halogène, alkyle, hydroxyalkyle, alcoxyalkyle, alcoxy, alcoxyalcoxy, alkylthio, alkylamino, dialkylamino, alkylsulfonyle, alkylsulfoxyle, alkylsulfonyloxy, alkylcarbonyle, alkylcarbonyloxy, alkylcarbonylamino, alcoxycarbonyle, alcoxycarbonylamino, alkylaminocarbonyle, dialkylaminocarbonyle, alkylaminothiocarbonyle, dialkylaminothiocarbonyle, alkylaminosulfonyle, dialkylaminosulfonyle, alcényle, alcényloxy, alcénylcarbonyloxy, alkinyle et alkinyloxy, ces groupes pouvant être entièrement ou partiellement halogénés; cycloalkyle, aryle, arylalkyle, arylalcoxy, aryloxy, arylthio, arylcarbonyle, arylcarbonyloxy, hétéroaryle, hétéroarylalkyle, hétéroarylalcoxy, hétéroaryloxy, hétéroarylthio, hétéroarylcarbonyle et hétéroarylcarbonyloxy, ces groupes pouvant être partiellement ou entièrement halogénés et/ou pouvant porter un à trois restes parmi les restes suivants: cyano, nitro, hydroxy, alkyle, halogénure d'alkyle, alcoxy, halogénure d'alcoxy ou alkylthio; R1 désigne hydrogène, cyano, nitro, hydroxy, mercapto, amino, carboxyle, aminocarbonyle, aminothiocarbonyle, sulfo, aminosulfonyle, halogène, alkyle, hydroxyalkyle, alcoxyalkyle, alcoxy, alcoxyalcoxy, alkylthio, alkylamino, dialkylamino, alkylsulfonyle, alkylsulfoxyle, alkylsulfonyloxy, alkylcarbonyle, alkylcarbonyloxy, alkylcarbonylamino, alcoxycarbonyle, alcoxycarbonylamino, alkylaminocarbonyle, dialkylaminocarbonyle, alkylaminothiocarbonyle, dialkylaminothiocarbonyle, alkylaminosulfonyle, dialkylaminosulfonyle, alcényle, alcényloxy, alcénylcarbonyloxy, alkinyle et alkinyloxy, ces groupes pouvant être entièrement ou partiellement halogénés; cycloalkyle, aryle, arylalkyle, arylalcoxy, arylthio, arylcarbonyle, arylcarbonyloxy, hétéroaryle, hétéroarylalkyle, hétéroarylalcoxy, hétéroaryloxy, hétéroarylthio, hétéroarylcarbonyle et hétéroarylcarbonyloxy, ces groupes pouvant être partiellement ou entièrement halogénés et/ou pouvant porter un à trois restes parmi les restes suivants: cyano, nitro, hydroxy, alkyle, halogénure d'alkyle, alcoxy, alcoxy halogéné ou alkylthio. L'invention concerne également des mélanges appropriés de ces composés.
EP96908131A 1995-04-08 1996-03-25 Compositions fongicides synergiques constituees de derives de quinoleine et en inhibiteurs de cytochrome b/c Withdrawn EP0820232A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19513404 1995-04-08
DE19513404 1995-04-08
PCT/EP1996/001298 WO1996032015A1 (fr) 1995-04-08 1996-03-25 Compositions fongicides synergiques constituees de derives de quinoleine et en inhibiteurs de cytochrome b/c

Publications (1)

Publication Number Publication Date
EP0820232A1 true EP0820232A1 (fr) 1998-01-28

Family

ID=7759274

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96908131A Withdrawn EP0820232A1 (fr) 1995-04-08 1996-03-25 Compositions fongicides synergiques constituees de derives de quinoleine et en inhibiteurs de cytochrome b/c

Country Status (13)

Country Link
EP (1) EP0820232A1 (fr)
JP (1) JPH11503435A (fr)
KR (1) KR19980703696A (fr)
CN (1) CN1180995A (fr)
AR (1) AR001514A1 (fr)
AU (1) AU5148696A (fr)
BR (1) BR9604823A (fr)
CA (1) CA2215514A1 (fr)
HU (1) HUP9801630A2 (fr)
IL (1) IL117785A0 (fr)
NZ (1) NZ304327A (fr)
WO (1) WO1996032015A1 (fr)
ZA (1) ZA962709B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002505660A (ja) 1996-09-10 2002-02-19 ファルマシア・アンド・アップジョン・カンパニー 抗ウィルス剤としての８―ヒドロキシ―７―置換キノリン
DE19710760A1 (de) * 1997-03-14 1998-09-17 Basf Ag Fungizide Mischung
ES2248923T3 (es) * 1997-12-22 2006-03-16 PHARMACIA & UPJOHN COMPANY LLC 4-hydroxiquinolin-3-carboxamidas y hidrazidas como agentes antivirales.
DE10063046A1 (de) * 2000-12-18 2002-06-20 Basf Ag Fungizide Mischungen
JP4667384B2 (ja) 2003-10-07 2011-04-13 レノビス， インコーポレイテッド イオンチャネルリガンドとしてのアミド誘導体および薬学的組成物、ならびにこれらを使用する方法
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
EP2345643A1 (fr) 2009-12-29 2011-07-20 Polichem S.A. Nouveaux dérivés de 8-hydroxyquinoline-7-carboxamide et leurs utilisations
EP2345641A1 (fr) 2009-12-29 2011-07-20 Polichem S.A. Nouveaux dérivés de 8-hydroxyquinoline-7-carboxamide secondaire
CN110156678A (zh) * 2019-05-27 2019-08-23 兰州大学 一种2,8-双(三氟甲基)喹啉类4-位修饰的衍生物在防治植物病害中的用途
CN112608275A (zh) * 2020-12-29 2021-04-06 兰州大学 一种2,8-双(三氟甲基)-4-羟基喹啉衍生物在制备和防治农业病害中的用途

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3225169A1 (de) * 1982-07-06 1984-01-12 Basf Ag, 6700 Ludwigshafen Chinolinderivate, verfahren zu ihrer herstellung, diese enthaltende mikrobizide und ihre verwendung zur bekaempfung von pilzen
IL89029A (en) * 1988-01-29 1993-01-31 Lilly Co Eli Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them
DE4130298A1 (de) * 1991-09-12 1993-03-18 Basf Ag Fungizide mischungen
DE4321206A1 (de) * 1993-06-25 1995-01-05 Bayer Ag Fungizide Wirkstoffkombinationen
US5436248A (en) * 1993-07-02 1995-07-25 Ciba-Geigy Corporation Microbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9632015A1 *

Also Published As

Publication number Publication date
HUP9801630A2 (hu) 1998-11-30
WO1996032015A1 (fr) 1996-10-17
BR9604823A (pt) 1999-01-05
AU5148696A (en) 1996-10-30
MX9707537A (es) 1997-11-29
CA2215514A1 (fr) 1996-10-17
CN1180995A (zh) 1998-05-06
AR001514A1 (es) 1997-10-22
IL117785A0 (en) 1996-08-04
NZ304327A (en) 1999-02-25
ZA962709B (en) 1997-10-06
KR19980703696A (ko) 1998-12-05
JPH11503435A (ja) 1999-03-26

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