Carbamate series of juvenoids: Variation of the O-alkyl substituent

Article abstract of DOI:10.1002/hlca.19940770218

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).