Synthesis, spectral studies, antimicrobial and insect antifeedant potent keto oxiranes

A series of ee (αS, βR) biphenyl keto oxiranes (biphenyl-4-yl[3-(substituted phenyl)oxiran-2-yl]methanones) have been synthesized by phase transfer catalysed epoxidation of biphenyl 2E-chalcones. The yields of oxiranes are more than 95%. The synthesized oxiranes have been characterized by IR, 1H, 13C and GC-MS spectra. The spectral data are correlated with Hammett substituent constants and Swain-Lupton parameters. From the regression analyses, the effect of substituent on the group frequencies has been predicted. The antimicrobial and insect antifeedant activities of all synthesized oxiranes have been evaluated.