EP1003726A1 - Nitrophenyle-sulfonyle-imidazoles et leur utilisation pour lutter contre des parasites vegetaux et animaux - Google Patents

Nitrophenyle-sulfonyle-imidazoles et leur utilisation pour lutter contre des parasites vegetaux et animaux

Info

Publication number
EP1003726A1
EP1003726A1 EP98941320A EP98941320A EP1003726A1 EP 1003726 A1 EP1003726 A1 EP 1003726A1 EP 98941320 A EP98941320 A EP 98941320A EP 98941320 A EP98941320 A EP 98941320A EP 1003726 A1 EP1003726 A1 EP 1003726A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
alkyl
spp
atoms
phenyl
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Withdrawn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
EP98941320A
Other languages
German (de)
English (en)
Inventor
Lutz Assmann
Klaus Stenzel
Christoph Erdelen
Martin Kugler
Peter Wachtler
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.)
Bayer CropScience AG
Original Assignee
Bayer AG
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
Priority claimed from DE19829740A external-priority patent/DE19829740A1/de
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1003726A1 publication Critical patent/EP1003726A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Definitions

  • R 3 has the meaning given above and
  • R 1 and R 2 together with the carbon atoms to which they are attached, preferably represent a benzene ring which is linked by double bonds
  • the compounds of formula (II) can exist in the following two tautomeric forms.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Uromyces species such as Uromyces appendiculatus
  • the active compounds according to the invention are also suitable for combating animal pests, in particular insects, arachnids and nematodes, which are useful in agriculture, in forestry, in horticulture, in the protection of stocks and materials and in the hygiene sector or in veterinary medicine, with good plant tolerance and favorable warm-blood toxicity Range occur.
  • the substances are effective against normally sensitive and resistant species and against pests in all or individual stages of development.
  • the animal pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for Seed, as well as ULV cold and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for Seed, as well as ULV cold and warm mist formulations.
  • the active compounds according to the invention can also be mixed with known fungicides, bactericides, acaricides, nematicides or
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofen carb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M,
  • Bacillus thuringiensis 4-bromo-2- (4-chloro-phenyl) - 1 - (ethoxymethyl) -5- (trifluoromethy ⁇ ) - lH-pyrrole-3-carbonitrile, bendiocarb, ben Divisionacarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromine A, bufencarb, buprofezin, butocarboxim, butylpyridaben,
  • Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathione, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos,
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Solvent 47 parts by weight of acetone emulsifier: 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Solvent 7 parts by weight of dimethylformamide emulsifier. 1 part by weight of alkylaryl polyglycol ether
  • Active ingredients according to the invention are added to an agar which is produced using malt extract in concentrations of 0.1 mg / 1 to 5000 mg / 1. After the agar has solidified, it is contaminated with pure cultures of test organisms. After two weeks of storage at 27 ° C and 60 to 70% relative humidity, the minimum inhibitory concentration (MIC value) is determined. The MIC value indicates the lowest concentration of active ingredient at which no growth occurs due to the microbe species used.
  • MIC value Minimum inhibitory concentration

Landscapes

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

Abstract

L'invention concerne de nouveaux nitrophényle-sulfonyle-imidazoles de la formule (I) dans laquelle X, R<1>, R<2> et R<3> ont les significations mentionnées dans la description. L'invention concerne également un procédé permettant de préparer de nouvelles substances, ainsi que leur utilisation pour lutter contre des parasites végétaux et animaux.
EP98941320A 1997-07-24 1998-07-13 Nitrophenyle-sulfonyle-imidazoles et leur utilisation pour lutter contre des parasites vegetaux et animaux Withdrawn EP1003726A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19731781 1997-07-24
DE19731781 1997-07-24
DE19829740 1998-07-03
DE19829740A DE19829740A1 (de) 1997-07-24 1998-07-03 Nitrophenyl-sulfonyl-imidazole
PCT/EP1998/004326 WO1999005116A1 (fr) 1997-07-24 1998-07-13 Nitrophenyle-sulfonyle-imidazoles et leur utilisation pour lutter contre des parasites vegetaux et animaux

Publications (1)

Publication Number Publication Date
EP1003726A1 true EP1003726A1 (fr) 2000-05-31

Family

ID=26038530

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98941320A Withdrawn EP1003726A1 (fr) 1997-07-24 1998-07-13 Nitrophenyle-sulfonyle-imidazoles et leur utilisation pour lutter contre des parasites vegetaux et animaux

Country Status (7)

Country Link
US (3) US6262100B1 (fr)
EP (1) EP1003726A1 (fr)
JP (1) JP2001510828A (fr)
CN (1) CN1264367A (fr)
AU (1) AU8974598A (fr)
PL (1) PL338191A1 (fr)
WO (1) WO1999005116A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10005278A1 (de) * 2000-02-07 2001-08-09 Bayer Ag Verfahren zur Herstellung von Sulfonyl-imidazol-Derivaten
DE10063116A1 (de) * 2000-12-18 2002-06-20 Bayer Ag Azinylsulfonylimidazole
US20110224252A1 (en) * 2007-10-26 2011-09-15 Syngenta Crop Protection, Inc. Novel imidazole derivatives
EP2053045A1 (fr) 2007-10-26 2009-04-29 Syngenta Participations AG Nouveaux dérivés d'imidazole
EP2053044A1 (fr) * 2007-10-26 2009-04-29 Syngenta Participations AG Nouveaux dérivés d'imidazole
EP2053046A1 (fr) * 2007-10-26 2009-04-29 Syngeta Participations AG Nouveaux dérivés d'imidazole

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1154722A (en) 1965-07-08 1969-06-11 Boots Pure Drug Co Ltd 2,4,5-Tribromoimidazole Derivatives and Compositions thereof
DE3605714A1 (de) 1986-02-22 1987-08-27 Bayer Ag Mikrobizide mittel
EP0284277A1 (fr) 1987-03-21 1988-09-28 AgrEvo UK Limited Fongicides de cyanoimidazole
JPH03246206A (ja) * 1990-02-21 1991-11-01 Sumitomo Chem Co Ltd トリハロイミダゾール誘導体を有効成分とするゴキブリ用殺虫剤
JPH0429974A (ja) 1990-02-22 1992-01-31 Sumitomo Chem Co Ltd トリハロイミダゾ−ル誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤
DE19609060A1 (de) 1995-08-10 1997-02-13 Bayer Ag Halogenbenzimidazole
IL122944A (en) * 1995-08-10 2001-11-25 Bayer Ag Halogenobenzimidazoles, their preparation and microbicidal compositions containing them
US5817823A (en) * 1997-04-17 1998-10-06 Sepracor Inc. Method for synthesizing 2-substituted imidazoles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9905116A1 *

Also Published As

Publication number Publication date
CN1264367A (zh) 2000-08-23
WO1999005116A1 (fr) 1999-02-04
US6486191B2 (en) 2002-11-26
US6350770B1 (en) 2002-02-26
JP2001510828A (ja) 2001-08-07
US20020094936A1 (en) 2002-07-18
PL338191A1 (en) 2000-10-09
AU8974598A (en) 1999-02-16
US20020022728A1 (en) 2002-02-21
US6262100B1 (en) 2001-07-17

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