Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-09-13
1998-03-10
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483021, 5483097, A01N 4352, C07D23510
Patent
active
057261997
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel substituted N-aryl- and N-alkylsulfonylaminals, to processes for their preparation and their use as agents for combating pests.
It is known that certain imidazoles and pyrroles such as, for example, 2,4-bis-trifluoromethyl-3-bromo-2-(4-chlorophenyl)-pyrrole have insecticidal properties (cf. e.g. JP 6 293 279 and EP 0 481 182).
However, the activity of these previously known compounds is not completely satisfactory in all areas of application, especially at low application rates and concentrations.
Novel N-aryl- and N-alkylsulfonylaminals have been found of the formula (I) ##STR2## in which R.sup.1 represents hydrogen, represents optionally substituted alkyl or represents optionally substituted aryl, substituted alkyl or represent optionally substituted aryl, and ##STR3## in which R.sup.4 represents fluoroalkyl and case represent hydrogen, halogen, cyano or nitro, or represent in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, represent optionally substituted, fused-on dioxyalkylene, represent hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl or cycloalkyloxycarbonyl, represent in each case optionally substituted amino or aminocarbonyl, or represent in each case optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulfonyl, or ##STR4## in which Ar represents optionally substituted phenyl, pyridyl or naphthyl and hydrogen, optionally substituted alkyl, cyano, nitro or halogen, represent optionally substituted alkylthio, represent optionally substituted alkylsulfinyl or represent optionally substituted alkylsulfonyl, or ##STR5## in which Ar has the meaning given above, substituted aryl, or nitro, represents optionally substituted alkylthio, represents optionally substituted alkylsulfinyl or represents optionally substituted alkylsulfonyl, or cyano, and ##STR6## in which X.sup.1, X.sup.2, X.sup.3 and R.sup.4 have the meaning given above.
The inclusion of the various meanings of the group A results in the following principal structures (Ia), (Ib), (Ic) and (Id): ##STR7## in which Ar, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1, X.sup.2, X.sup.3, X.sup.4, Y.sup.1, Y.sup.2, Y.sup.3, Z.sup.1 and Z.sup.2 have the meanings given above.
The compounds of the formula (I) may if appropriate, depending on the nature and number of the substituents, be present as geometrical and/or optical isomers or regioisomers or their isomer mixtures in differing composition. Both the pure isomers and the isomer mixtures are claimed according to the invention.
In particular, the compounds of the formula (Ia) may be present as isomers, depending on which of the two nitrogen atoms in the imidazole ring carries the substituent.
The compounds of the formula (Ic) may be present as isomers in respect of the position of the substituents in positions 4 and 5.
Furthermore, it has been found that the novel substituted N-aryl- and N-alkylsulfonylaminals of the formula (I) are obtained by reacting heterocycles of the formula (VI) ##STR8## in which R.sup.1, R.sup.2 and R.sup.3 have the meanings given above and reaction auxiliary.
Finally it has been found that the novel substituted N-aryl- and N-alkylsulfonylaminals of the formula (I) possess good activity against pests.
Surprisingly, the substituted N-aryl- and N-alkylsulfonylaminals of the formula (I) according to the invention display a considerably better activity against animal pests than the previously known compounds which are closest to them in terms of their constitution.
A general definition of the substituted N-aryl- and N-alkylsulfonylaminals according to the invention is given by the formula (I). branched alkyl having 1 to 8 carbon atoms or represents phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms, in each case straight-chain or branched h
REFERENCES:
patent: 5310747 (1994-05-01), Enomoto et al.
patent: 5510364 (1996-04-01), Lunkenheimer et al III
Cram & Hammond, "Organic Chemistry", McGraw-Hill Books NY, (1964) 2nd Ed, pp. 565-567.
Baasner Bernd
Erdelen Christoph
Hagemann Hermann
Heil Markus
Lieb Folker
Bayer Aktiengesellschaft
Morris Patricia L.
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