Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-05-25
1997-08-12
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548113, 5483097, 5483101, 5483104, A01N 4352, C07D23510
Patent
active
056566492
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new substituted benzimidazoles, to a plurality of processes for their preparation, and to their use as pesticides.
It has been disclosed that certain phosphoric esters or carbamates, such as, for example, the compound O,S-dimethyl-thiolo-phosphoramide or the compound O-(2-isopropoxyphenyl) N-methyl-carbamate, have insecticidal properties (cf., for example, DE 1,210,835 or DE 1,108,202).
However, the level, or duration, of action of these previously known compounds is not entirely satisfactory in all fields of application, in particular in the case of certain insects or when low concentrations are applied.
New substituted benzimidazoles of the general formula (l) ##STR2## in which R.sup.1 represents hydrogen, alkyl, alkoxy or optionally substituted aryl, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl(--CONH.sub.2), alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylcarbonyloxy or (hetero)arylaminocarbonylaminocarbonyloxy, case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl or in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X.sup.1, X.sup.2, X.sup.3 or X.sup.4 represents halogenoalkyl, with the exception of the chloromethyl radical, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl or alkylsulphonyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl, or in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl,
The compounds of the formula (I) may optionally be present in the form of geometric and/or optical isomers or regioisomers or their isomer mixtures in varying composition, depending on the nature and number of the substituents. The invention claims the pure isomers and the isomer mixture.
Furthermore, it has been found that the new substituted benzimidazoles of the general formula (I) ##STR3## in which R.sup.1 represents hydrogen, alkyl, alkoxy or optionally substituted aryl, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero)aryl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylcarbonyloxy or (hetero)arylaminocarbonylaminocarbonyloxy, case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl or in each case optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X.sup.1, X.sup.2, X.sup.3 or X.sup.4 represents halogenoalkyl, with the exception of the chloromethyl radical, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl, halogenoalkylsulphonyl or alkylsulphonyl, optionally substituted, fused dioxyalkylene, or represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, in each case optionally substituted amino or aminocarbonyl, or in each case optionally substituted aryl, arylthio, arylsulphinyl, arylsulphonyl, arylsulphonyloxy, ar
REFERENCES:
patent: 3472865 (1969-10-01), Newbold et al.
patent: 3531495 (1970-09-01), Burton et al.
patent: 5306692 (1994-04-01), Barton et al.
Baasner Bernd
Bohm Stefan
Dehne Heinz-Wilhelm
Gorgens Ulrich
Lieb Folker
Bayer Aktiengesellschaft
Morris Patricia L.
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