Synthesis and Insecticidal Activity of Novel 4β-Halogenated Benzoylamino Podophyllotoxins against Pieris rapae LINNAEUS

概要

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Twelve new 4β-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 250 ppm. 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 15d against P. rapae in vivo. Especially compounds 7.5 and 7.6 bearing metaand para-chlorobenzene substituents respectively, were the most potent of these compounds; 2) Substitution on the benzene ring moiety of 4β-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 4β-benzoylamino podophyllotoxin with I either at the ortho, meta or para position yielded less potent compounds (7.10 -7.12) when compared with PPT.
公益社団法人日本薬学会の論文
2002-03-01