Synthesis and insecticidal activity of novel 4beta-halogenated benzoylamino podophyllotoxins against Pieris rapae Linnaeus

Chemical & Pharmaceutical Bulletin
Hui XuYan-Guang Wang

Abstract

Twelve new 4beta-halogenated benzoylamino compounds (7.1-7.12) of podophyllotoxin have been synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra as well as CHN elemental analysis. These compounds showed delayed insecticidal activity against 5th instar larvae of Pieris rapae Linnaeus in vivo, when tested by a leaf-dipping method at a concentration of 250ppm. By preliminary qualitative structure-activity relationship analysis, we found the following results: 1) Compounds 7.2, 7.5-7.9 were more potent than the nature parent product in the mortality after 15 d against P. rapae in vivo. Especially compounds 7.5 and 7.6 bearing meta- and para-chlorobenzene substituents respectively, were the most potent of these compounds; 2) Substitution on the benzene ring moiety of 4beta-benzoylamino podophyllotoxin (PPT) with Cl, Br, I at the para or at the meta position yielded compounds which were as potent or more potent than those containing the corresponding substituting group at the ortho position. 3) Substitution on the benzene ring moiety of 4beta-benzoylamino podophyllotoxin with I either at the ortho, meta or para position yielded less potent compounds (7.10-7.12) when compared with PPT.

References

Aug 1, 1970·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·H Stähelin
Oct 1, 1980·Chemical & Pharmaceutical Bulletin·T TakemotoH Taniyama
Dec 22, 1999·Journal of Agricultural and Food Chemistry·M MiyazawaY Ishikawa

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Citations

Aug 11, 2007·Natural Product Research·Ying-Qian LiuRong Gao
Dec 7, 2007·Chemical & Pharmaceutical Bulletin·Hui XuMin Lv
May 3, 2008·Chemical & Pharmaceutical Bulletin·Hui XuYong-Tang Zheng
Jul 15, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei-Hua ChengZhong-Mei Zou
Aug 11, 2004·Toxicon : Official Journal of the International Society on Toxinology·E S Garcia, P Azambuja

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