Synthesis and Insecticidal Activity of Fire Ant Venom Alkaloid-Based 2-Methyl-6-alkyl-Δ1,6-piperideines |
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| Authors: | Xiaoqing Wu Guangyu Wang Guangxin Xu Li Chen |
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| Institution: | 1.State Key Laboratory of Integrated Management of Pest Insects and Rodents, Institute of Zoology, Chinese Academy of Sciences, Beijing 100101, China;2.School of Life Sciences, Institute of Life Science and Green Development, Hebei University, Baoding 071002, China; (G.W.); (G.X.) |
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| Abstract: | 2,6-dialkylpiperideines found in the venom of Solenopsis (Hymenoptera, Formicidae) fire ants are a range of compounds possessing various biological activities. A series of racemic 2-methyl-6-alkyl-Δ1,6-piperideines were synthesized for chemical confirmation of the natural products found in fire ant venom, and the evaluation of their biological activity. Synthetic Δ1,6-piperideines and the natural compounds in the cis-alkaloid fraction of Solenopsis invicta had identical mass spectra and retention times. Their insecticidal activities against the third-instar larvae of cotton bollworm (Helicoverpa armigera) were evaluated by using injection and topical application methods. All three compounds exhibited no lethal effect at concentrations of 0.05–0.4 mol/L by topical treatment, but moderate lethal effect at 0.4 mol/L through injection treatment. Compound 6a showed significantly higher activity than the natural insecticide nicotine. The differences in activity among compounds 6b, 6c and nicotine were not significant. The elongation of the carbon chain at the 6-position of the piperideine ring appears to decrease insecticidal activity. |
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| Keywords: | piperideine venom Solenopsis invicta biological activity contact toxicity injection toxicity |
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