In view of potential agricultural
activity of sarisan (isolated
from many plants or easily synthesized from sesamol, another biorenewable
natural product) analogues, many research studies on the application
of these biorenewable and abundant natural resources have been proceeded.
A series of novel sarisan analogues containing N-phenylpyrazole
were synthesized and evaluated for their insecticidal activity against
a crop-threatening insect pest, Mythimna separata Walker. Meanwhile, an iodine-mediated oxidative intramolecular C–N
bond formation methodology has been established for the one-pot synthesis
of these N-phenylpyrazole-containing sarisan analogues.
This practical one-pot methodology is metal-free and requires no separation
of the less stable intermediate hydrazones. In addition, it was found
that compounds 8l–r exhibited more promising insecticidal
activity with the final mortality rates (FMRs) >62.1%, when compared
with the positive control toosendanin. Especially, compound 8r with 2-fluoro-4-bromophenyl showed the most potent insecticidal
activity, the FMR of which was 79.3%. On the basis of this, some interesting
results of structure–activity relationships were also discussed.