Synthesis and Chemistry of Agrochemicals III - ACS Publications

D. G. Kuhn, V. M. Kamhi, J. A. Furch, R. E. Diehl, S. H. Trotto,. G. T. Lowen, and T. J. Babcock. American Cyanamid Company, Agricultural Research Div...
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Chapter 26

Insecticidal Pyrroles Arylpyrrolecarbonitriles Incorporating a Trifluoromethyl Group

Downloaded by STANFORD UNIV GREEN LIBR on June 22, 2012 | http://pubs.acs.org Publication Date: September 22, 1992 | doi: 10.1021/bk-1992-0504.ch026

D. G. Kuhn, V. M. Kamhi, J. A. Furch, R. E. Diehl, S. H. Trotto, G. T. Lowen, and T. J. Babcock American Cyanamid Company, Agricultural Research Division, P.O. Box 400, Princeton, NJ 08543-0400

A series of new arylpyrrolecarbonitriles containing a trifluoromethyl group has been prepared. These compounds, based on a naturally occurring compound dioxapyrrolomycin, have broad spectrum insecticidal activity. This reports details the preparation of these compounds utilizing a new cycloaddition reaction. Preliminary structure-activity comparisons are also presented. A variety of natural products have served as potential insect control agents or as "leads" for the development of synthesis programs aimed at producing structurally less complex molecules with equal or improved biological activity. Recently, we detailed our work on the discovery of a new series of dihalopyrroles