Application of Sustainable Natural Bioresources in Agriculture: Iodine-Mediated Oxidative Cyclization for Metal-Free One-Pot Synthesis of N -Phenylpyrazole Sarisan Analogues as Insecticidal Agents

ACS Omega
Lailiang QuYong Guo

Abstract

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.

References

Sep 1, 1996·The Science of the Total Environment·D Koh, J Jeyaratnam
Jan 28, 1998·Annual Review of Entomology·T S DhadiallaD P Le
Mar 14, 2001·Anais Da Academia Brasileira De Ciências·D L MoreiraE F Guimarães
Nov 13, 2003·Journal of Agricultural and Food Chemistry·Pierluigi CaboniJohn E Casida
Jul 27, 2005·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Claus M PassreiterMurray B Isman
Mar 4, 2008·Biological & Pharmaceutical Bulletin·Chang-Seob SeoJong-Keun Son
Jun 15, 2012·Bioorganic & Medicinal Chemistry Letters·Ravindra B PathakH H Parekh
Jun 26, 2012·Journal of Agricultural and Food Chemistry·Yong GuoHui Xu
Sep 29, 2012·Science·David G Heckel
Feb 7, 2013·European Journal of Medicinal Chemistry·A M VijeshHoong Kun Fun
May 15, 2013·Bioorganic & Medicinal Chemistry·İrfan KocaYusuf Tutar
Nov 16, 2013·European Journal of Medicinal Chemistry·Kamal M DawoodPeter Metz
Nov 23, 2013·Journal of Agricultural and Food Chemistry·Yong GuoHui Xu
Jun 22, 2016·Bioorganic & Medicinal Chemistry Letters·Hong DaiHaibing He

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Methods Mentioned

BETA
gel column chromatography
NMR

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