New insecticidal amides from petroleum ether extract of dried Piper nigrum L. whole fruits

Abstract

The petroleum ether extract of dried ground whole fruits of Piper nigrum L. afforded 20 compounds (1-20) including two new insecticidal amides named as pipnoohine (1), and pipyahyine (2), seven reported for the first time from this plant (12, 13, 15-17, 19, 20), and eleven known compounds (3-11, 14, 18). The structure of 1 has been elucidated as (2E,4E,12Z)-N-(4-methylpentyl)octadeca-2, 4,12-trienamide and that of 2 as (2E,4E,11E)-12-(benzo[1,3]dioxol-5-yl)-N-(3- methylbutyl)dodeca-2,4,11-trien-amide through extensive ID-, 2D-NMR spectral studies and chemical reactions. The known compounds have been identified through comparison of their spectral data with those reported in literature. 1 and 2 exhibited toxicity at 35.0 and 30.0 ppm respectively against fourth instar larvae of Aedes aegypti L. by WHO method. © 2004 Pharmaceutical Society of Japan.