Structure–activity relationship of novel juvenile hormone, JHSB3, isolated from the stink bug, Plautia stali

The structure–activity relationship of JHSB3 isolated from the pentatomid bug, Plautia stali, was studied. Various synthetic analogs were synthesized and subjected to the juvenilizing activity tests using the last instar nymphs of P. stali. These studies indicated that the coexistence of the ester carbonyl group, two epoxides at C2,3 and C10,11 were proved to be crucial for the potent juvenilizing activity. Among the tested analogs, we found highly potent analogs in which the C6,7 double bond of JHSB3 was saturated (0.1 μg/insect). The methoxy analogs in which the epoxide moiety at C10,11 was substituted with a methoxy group exerted a moderate juvenilizing activity.