Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-10-03
1999-07-20
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514380, 548243, 548247, 548249, 5483021, 5483047, A01N 4380, C07D41312
Patent
active
059256630
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel benzimidazole derivatives, to a process for their preparation and to their use as microbicides in crop protection and in the protection of materials.
It is already known that certain benzimidazole derivatives have fungicidal properties (cf. DE-A 4 139 950 and EP-A 0 517 476). Thus, for example nzimidazole and zole can be used for controlling fungi. The activity of these compounds is good, but in some cases leaves something to be desired at low application rates.
This invention, accordingly, provides novel benzimidazole derivatives of the formula ##STR2## in which X.sup.1, X.sup.2, X.sup.3 and X.sup.4 independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, optionally substituted cycloalkyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl, represent ##STR3## in which R.sup.3 and R.sup.4 independently of one another each represent hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted arylsulphonyl, optionally substituted arylaminocarbonyl or optionally substituted arylmethylsulphonyl or to represent an optionally alkyl-substituted heterocyclic ring which may contain an additional oxygen atom or an aklylimino group, substituted heterocyclyl and an azo group or heterocyclyl radical, or or heterocyclyl radical, or group is linked to the aryl or heterocyclyl radical, or chain having 3 or 4 members wherein one or two (non-adjacent) carbon atoms may be replaced by oxygen atoms, ##STR4## R.sup.6 represents alkyl, halogenoalkyl or optionally halogen- and/or halogenoalkyl-substituted benzyl, --, --CO--, --SO.sub.2 --, --CO--O-- or --SO--O-- where in the case of the last two groups the carbon atom or the sulphur atom is linked to the nitrogen atom of the imidazole ring,
Furthermore, it was found that benzimidazole derivatives of the formula (I) and acid addition salts and metal salt complexes thereof are obtained when cyanobenzimidazoles of the formula ##STR5## in which X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each as defined above presence of a diluent, and the resulting benzimidazoles of the formula ##STR6## in which R.sup.2, Y, X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each as defined above the presence of a diluent, or presence of a diluent, and an acid or a metal salt is, if appropriate, added to the resulting compounds of the formula (I).
Finally, it was found that the benzimidazole derivatives of the formula (I) and acid addition salts and metal salt complexes thereof have very good microbicidal properties and can be used in crop protection and in the protection of materials.
Surprisingly, the compounds according to the invention have better fungicidal activity than enzimidazole and azole, which are compounds of the prior art of a similar structure and of the same direction of action.
A general definition of the compounds according to the invention is given by the formula (I). preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain or branched halogenoalkoxy having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylthio having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylthio having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphinyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphinyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, straight-ch
REFERENCES:
patent: 5656649 (1997-08-01), Lunkenheimer et al.
Assmann Lutz
Kugler Martin
Marhold Albrecht
Stenzel Klaus
Bayer Aktiengesellschaft
Morris Patricia L.
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