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Synthesis and Insecticidal Activities of 2-Cl-4α-Ester Derivatives of Podophyllotoxin(I)

Author: LiuBin
Tutor: XuZuo
School: Northwest University of Science and Technology
Course: Botany
Keywords: podophyllotoxin derivatives synthesis insecticidal activity
CLC: S482.3
Type: Master's thesis
Year: 2009
Downloads: 21
Quote: 0
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Abstract


In order to make sure of the relationships between structure and insecticidal activity (SAR) of podophyllotoxin as well as to develop new insecticide from natural products, derivatives of podophyllotoxin which bearing 2-Cl substitute were designed and synthesized. The Antifeedant activity and insecticidal activity of target compounds were evaluated against the 3rd larvae of Mythimna separata. The results were as follows:1.Eight 2-Cl-4α-ester derivatives of podophyllotoxin analogues were prepared and Their chemical structure were confirmed by MS and 1HNMR. All of these nine compounds were reported first.2.The antifeedant activitiy during 24h and 48h and insecticidal activity of nine target compounds ( 3a-3h ) and two intermediates ( 1, 2 ) against the 3rd-instar larvae of Mythimna separata were assayed by leaf-disk method at concentration of 1000μg/ml. The antifeedant activitiy of all target compounds is lower than that of podopyllotoxin and toosedanin, this mean that introduce 2-Cl and 4-acly to podophyllotoxin can’t enhace podophyllotoxin’antifeedant activitiy.3.As to the insecticidal activity, we found that all target compounds is superier that of podophyllotoxin and toosedanin, a commercial insecticide derived from Melia azedarach. But the insecticidal activity of two intermediates ( 1, 2 ) is lower or comparative to podophyllotoxin.4.Through analysis of the relationships between structure and insecticidal activity we drowed some qualitative structure–activity relationships. These compounds contain short carbon chain( 3a, 75% ) shows more potent than that with long carbon chain. Among esters ( 3b、3c、3d、3g ) derived from aromatic acid which bearing electron donating groups on the benzene ring will enhance the insecticidal activity ( 3c ).

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CLC: > Agricultural Sciences > Plant Protection > Pesticide ( chemical control ) > Various pesticides > Pesticides
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