Carbamate Series of Juvenoids: Variation of the <i>O</i>‐alkyl substituent

Abstract

Abstract By changing the O ‐alkyl substituents of the carbamate moiety of alkyl N ‐{2‐{4‐[(2‐oxocyclohexyl)methyl]phenoxy}ethyl}carbamates and subsequent transformation of the oxo group in the cyclohexyl substituent, the juvenoids 1–20 were synthesized ( Scheme ). The methyl ( 1–4 ), propyl ( 9–12 ), isopropyl ( 13–16 ), and prop‐2‐ynylcarbamates ( 17–20 ) were subjected to biological screening on several non‐related insect species ( Tenebrio molitor, Galleria mellonella, Dysdercus cingulatus , and Pyrrhocoris apterus ). Some of the juvenoids showed high biological activity and excellent selectivity with respect to target insect species ( Table 2 ).