Methylene group modifications of the N-(isothiazol-5-yl)phenylacetamides. Synthesis and insecticidal activity
1999
Samaritoni, J.G. | Babcock, J.M. | Schlenz, M.L. | Johnson, G.W.
It has been shown that oxidation at the alpha-carbon of N-(4-chloro-3-methyl-5-isothiazolyl)-2-[p-[(alpha, alpha,alpha-trifluoro-p-tolyl)oxy]phenyl]acetamide (1) is conveniently brought about using dimethylformamide dimethylacetal to give N-(4-chloro-3-methyl -5-isothiazolyl)-beta-(dimethylamino)-p-[(alpha, alpha,alpha-trifluoro-p-tolyl)oxy]atropamide (2), which has served as a common starting point for a variety of functional group transformations. These transformations were found to proceed in moderate to good yields to give derivatives of 1 that retained much of the efficacy associated with the parent amide and have allowed for an expansion of the SAR to be developed. Examples of enamines, enols, enol (thio)- ethers, oximes, and hydrazones were prepared. In particular, the enamines derived from low molecular weight amines and amino acids were most active as broad-spectrum insecticides and were found to be even more active than 1 on root-knot nematode.
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