抄録
Juvenile hormone (JH) is an important insect hormone that maintains the immature characters during development (a juvenilizing effect). The structure determination studies have been extensively implemented due to the biological importance of JH in insect physiology. Moreover, JH has attracted much attention as a prime lead molecule to develop a "third-generation pesticide", because JH is a natural hormone and its mimics would be advantageous in terms of the suppression of a drug-resistance. In fact, many JH analogs have been developed based on the structures of JH I (1), JH II (2), and JH III (3). We have recently achieved the structure determination of a novel JH from a stink bug, Plautia stali and are named it juvenile hormone III skipped bisepoxide (JHSB3). This is the first example of the JH isolated from heteropteran insects. Heteroptera includes many agricultural and medical pests. In this study, we explored structure activity relationship of JHSB3 toward development of heteropteran specific insecticides. Various analogs were synthesized and subjected to the juvenilizing activity test using last instar nymphs of P. stali. These results indicated that the ester carbonyl group together with two epoxides at C2,3 and C10,11 were proven to be the crucial functional groups for the juvenilizing activity. Among the analogs, we found highly potent analogs in which the C7 position of JHSB3 was saturated (0.1 μg/insect). The methoxy analogs where the epoxide moiety at C10,11 was substituted with a methoxy group exerted moderate juvenilizing activities. These results would be useful information to develop heterpoteran specific insecticides.
