title: Synthesis of some ester derivatives of 4'-demethoxyepipodophyllotoxin/2'-chloro-4'-demethoxyepipodophyllotoxin as insecticidal agents against oriental armyworm, Mythimna separata Walker.
abstract: Podophyllotoxin is a naturally occurring non-alkaloid toxin isolated from the roots and rhizomes of Podophyllum peltatum and P. hexandrum. In continuation of our program aimed at the discovery and development of natural product-based insecticides, two series of ester derivatives of 4'-demethoxyepipodophyllotoxin/2'-chloro-4'-demethoxyepipodophyllotoxin were prepared. The structures of the target compounds were well characterized by 1H NMR, IR, optical rotation and mp. The precise three-dimensional structural information of 8j was further determined by single-crystal X-ray diffraction. Their insecticidal activity was tested against Mythimna separata Walker. These compounds showed delayed insecticidal activity. Among all derivatives, some compounds showed more potent insecticidal activity than toosendanin against M. separata; especially compounds 8k and 9k exhibited the most potent activity with the final mortality rates of 71.4%. Their structure-activity relationships were discussed.
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China; School of Chemistry & Chemical Engineering, Ankang University, Ankang 725000, Shaanxi Province, China.
authors.forename: Jiulin
authors.initials: J
authors.lastname: Huang
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Ming
authors.initials: M
authors.lastname: Xu
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Shaochen
authors.initials: S
authors.lastname: Li
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
authors.forename: Jiani
authors.initials: J
authors.lastname: He
authors.affiliation: Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China; Shaanxi Key Laboratory of Natural Products & Chemical Biology, Northwest A&F University, Yangling 712100, Shaanxi Province, China. Electronic address: orgxuhui@nwsuaf.edu.cn.
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects*; D011034:Podophyllotoxin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D011035:Podophyllum / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D004952:Esters; D007306:Insecticides; D011034:Podophyllotoxin
keywords: 2′-Chloro-4′-demethoxyepipodophyllotoxin; 4′-Demethoxyepipodophyllotoxin; Insecticidal activity; Mythimna separata Walker; Podophyllotoxin