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A series of plumbagin derivatives (4a-4k) containing an amino acid moiety were synthesized under mild esterification conditions in excellent yields (35%-80%) and screened for their antifeedant activities in tobacco caterpillar (Spodoptera litura) and castor semilooper (Achaea janata) using a no-choice laboratory bioassay. The parent compound plumbagin lacked significant activity, but the analogues were effective in reducing feeding by two insect species. The introduction of an N-acetyl-l-amino acid side chain to the Michael adduct of plumbagin at the third position of the quinone moiety significantly increased antifeedant activity. Several of the analogues were also toxic or caused developmental abnormalities following topical administration.

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The vapor-phase toxicity of Derris scandens Benth.-derived constituents was evaluated against four stored-product pests ( Callosobruchus chinensis L., Sitophilus oryzae L., Rhyzopertha dominica L., and Tribolium castaneum H.) using fumigation bioassays and compared to those of commonly used insecticides. The structures of all constituents of were characterized by spectroscopic analyses [nuclear magnetic resonance (NMR) and mass spectrometry]. The sensitivity of the test insect to compounds varied with exposure time, concentration, and insect species. Over 100% mortality after 24 h was achieved with the compounds osajin (2), scandinone (5), sphaerobioside (8), and genistein (9) against all of the test insects, while laxifolin (3) and lupalbigenin (4) showed 100% mortality after 72 h against T. csataneum and R. dominica . Scandenone (1), scandenin A (6), and scandenin (7) were less effective. Among the insects, C. chinensis , S. oryzae , and R. dominica were more susceptible to the treatments, whereas T. castaneum was less susceptible. The results of fumigation tests indicated that compounds from D. scandens whole plant extract are potential candidates to control stored-product pests.

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