Design, Synthesis, and Bioassay of Novel Compounds of Isolongifolenone Oxime Derivatives

Abstract

A succession of new isolongifolenone oxime derivatives have been designed and synthesized. The structures of these compounds were identified by IR, 1H‐NMR, 13C‐NMR, mass spectra, and elemental analysis. The bioassays of antibacterial, antifungal, and insecticidal activity were carried out. The in vitro antibacterial and antifungal activities were evaluated by the disk diffusion method, and the minimum inhibitory concentration was determined by the microdilution method, while the insecticidal activity was tested by the spraying method or the straw impregnation method. The results of bioassays showed that compound 3f was more active in resisting all the tested bacterial and fungal organisms when compared to the standard drug amoxicillin at the lowest concentration of 31.3 μg/ml. Compound 4, synthesized by Beckmann rearrangement reaction of isolongifone oxime, exerted moderate insecticidal activity against soybean aphid. Furthermore, compound 3m exhibited more activity in killing armyworms than the standard drug flucycloxuron at the concentration of 0.5 mg/l.