Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-04-24
1996-12-17
Haley, Jacqueline
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483021, 5483097, 504276, A61K 31415, A01N 4352, C07D23510
Patent
active
055853951
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP 93/02947 filed Oct. 25, 1993.
The invention relates to new substituted benzimidazoles, to a number of processes for their preparation and to their use as pest control agents.
It is known that certain phosphoric acid esters or carbamates, such as, for example, the compound O,S-dimethyl-thiolo-phosphoramide or the compound N-methyl-O-(2-isopropoxyphenyl)carbamate have insecticidal properties (cf. e.g. DE 12 10 835 and DE 11 08 202, respectively).
The level and/or duration of action of these previously known compounds, however, in particular in the case of certain insects or at low application concentrations, is not completely satisfactory in all areas of application.
New substituted benzimidazoles have been found of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen, alkyl, halogenoalkyl, cycloalkyl or optionally substituted aryl, substituted aryl, case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, dioxyalkylene which is optionally substituted and may be fused on, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, 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 with at least one of the substituents X.sup.1, X.sup.2, X.sup.3 and X.sup.4 being different from hydrogen, 1-(N,N-dimethylaminosulphonyl)-2-trifluoromethyl-4-nitro-6-trifluoromethyl -benzimidazole, 1-(N,N-diethylaminosulphonyl)-2-trifluoromethyl-4-nitro-6-trifluoromethyl- benzimidazole and 1-[N,N-bis-(n-propyl)-aminosulphonyl]-2-trifluoromethyl-4-nitro-6-trifluor omethylbenzimidazole.
Depending on the nature and number of the substituents, the compounds of the formula (I) may optionally be present as geometrical and/or optical isomers or regioisomers, or mixtures of these isomers in varying composition. Both the pure isomers and the isomer mixtures are claimed according to the invention.
It has also been found that the new substituted benzimidazoles of the general formula (I) ##STR3## in which R.sup.1 represents hydrogen, alkyl, halogenoalkyl, cycloalkyl or optionally substituted aryl, substituted aryl, case represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, dioxyalkylene which is optionally substituted and may be fused on, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, 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 with at least one of the substituents X.sup.1, X.sup.2, X.sup.3 and X.sup.4 being different from hydrogen, 1-(N,N-dimethylaminosulphonyl)-2-trifluoromethyl-4-nitro-6-trifluoromethyl -benzimidazole, 1-(N,N-diethylaminosulphonyl)-2-trifluoromethyl-4-nitro-6-trifluoromethyl- benzimidazole and 1-[N,N-bis-(n-propyl)-aminosulphonyl]-2-trifluoromethyl-4-nitro-6-trifluor omethylbenzimidazole, are obtained if 1H-benzimidazoles of the formula (II) ##STR4## in which R.sup.3, X.sup.1, X.sup.2, X.sup.3 and X.sup.4 have the meaning given above are reacted with halogenosulphonamides of the formula (III) ##STR5## in which Hal represents halogen and reaction auxiliary.
Finally it has been found that the new substituted benzimidazoles of the general formula (I) have a good activity against pests.
Surprisingly, the substituted benzimidazoles of the general formula (I) according to the invention display a considerably improved insecticidal activity, in comparison to the phosphoric acid esters or carbamates known from the prior art, such as, for example, the compound O,S-dimethyl-thiolo-phosphoramide or the compound N-methyl-O-(2-isopropoxyphenyl)carbamate, which in terms of their
REFERENCES:
patent: 3823154 (1974-07-01), Corbett et al.
patent: 3980784 (1976-09-01), Peterson
patent: 4622323 (1986-11-01), Giraudon et al.
CA 66:28771p (8)1967.
Baasner Bernd
Erdelen Christoph
G orgens Ulrich
Lieb Folker
Lunkenheimer Winfried
Bayer Aktiengesellschaft
Haley Jacqueline
Stockton Laura L.
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