Synthesis and insecticidal activities of novel derivatives of podophyllotoxin.
In order to find the biorational pesticides, eight novel 4beta-substituted phenoxyaniline derivatives of podophyllotoxin (4a-h) have been synthesized with significant stereoselectivity and improved yields by employing the BF(3).Et(2)O/NaI reagent system and evaluated for insecticidal activity against Pieris rapae as well as for their antifeedant effect against fifth instar larvae of P. rapae. The results showed that all these derivatives of PPT showed delayed insecticidal activity, which is different from the traditional neurotoxic insecticides. Among them, compounds possessing a 4beta-phenoxyaniline moiety substituted at para (CO(2)C(2)H(5), Cl, and OH) position exhibited greater insecticidal activity against P. rapae than podophyllotoxin. Also, the antifeedant activities showed that these compounds exhibited less potency than podophyllotoxin.
Liu
Ying-Qian
YQ
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, PR China.
Yang
Liu
L
Liu
Yanqing
Y
Di
Xudong
X
Xiao
Hang
H
Tian
Xuan
X
Gao
Rong
R
D000818:Animals; D005247:Feeding Behavior / Q000187:drug effects*; D005638:Fruit / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis / Q000494:pharmacology; D018653:Juniperus / Q000737:chemistry*; D007814:Larva / Q000187:drug effects; D007915:Lepidoptera / Q000187:drug effects*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D011034:Podophyllotoxin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology
D007306:Insecticides; D011034:Podophyllotoxin