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Synthesis and Insecticidal Activities of C Ring Modified Derivatives of Podophyllotoxin (Ⅰ)

Author: ZhangLei
Tutor: XuZuo
School: Northwest University of Science and Technology
Course: Botany
Keywords: podophyllotoxin sulfonamide antifeedant avtivity insecticidal activity structure-activity relationships
CLC: S482.3
Type: Master's thesis
Year: 2009
Downloads: 41
Quote: 2
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Abstract


It is a significant way to develop insecticidal agents form natural products. Podophyllotoxin is a important antitumor drug precursor as well as a promising leading compound for insecticidal agents. In order to make sure of the relationships between structure and insecticidal activities (SAR) of podophyllotoxin and to develop new insecticide, we designed and synthesized twelve derivatives of podophyllotoxin which bearing 4β- sulfonamide moiety. The Antifeedant activities and insecticidal activities of target compounds were evaluated against the third-instar larvae of Mythimna separata in vivo. The results showed as follows:1. Twelve 4β- sulfonamide podophyllotoxin analogues were prepared and their chemical structures were confirmed by MS, HRMS and 1HNMR. Among these compounds ten (E1—E9, E11) were reported first time.2. The antifeedant activitiy (during 24h and 48h) and insecticidal activity of twelve target compounds (E1—E12) against the 3rd-instar larvae of Mythimna separata were assayed by leaf-disk method at concentration of 1000μg ml-1. The antifeedant activitiy of all target compounds is lower than that of podopyllotoxin and toosedanin.3. As to insecticidal activity, showed that all these derivatives of podopyllotoxin showed delayed insecticidal activity, which is different from the traditional neurotoxic insecticides. Most of these derivatives have shown promising insecticidal activities. For instance, E1—E11 showed greater insecticidal activity against third instar larvae of Mythimna separata than podopyllotoxin and E9 (88.9%), E11 (92.6%) were more potent than Toosendanin, a commercial insecticide.4. Some preliminary qualitative structure–activity relationships: we found either introduce electron withdrawing groups or electron donating groups on the benzene ring of 4β-sulphonamido moiety will enhance the insecticidal activities; Compound which bearing a aliphatic sulphonamido moiety (E11) possessed superior insecticidal activities than those bearing a aromatic one (E1—E10, E12); introduce Cl at the para position on the benzene ring of 4β-sulphonamido moiety improved insecticidal activities to a great extent than other substitutes (e.g. p-Br, E7, 77.8%; p-Ome, E4, 77.8%; p-Et, E5, 74.1% etc.); With Br at the para position (E7) on the benzene of 4β-sulphonamido moiety is more active than that Br at the ortho position (E8) .

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