Semisynthesis of N-acyl homoserinelactone derivatives and the antifeedant activity against Mythimna separata

Abstract

Seven homoserine-lactone (HL) acylated derivatives (HL1-HL7) were synthesized to determine the differences in antifeedant affects. The differences between these derivatives and tutin against Mythimna separata were tested. The structural assignments of these semisynthetic compounds were examined based on their infrared radiaion (IR), electrospray ionization mass spectrometry (ESIMS), and ¹H- and ¹³C-nuclear magnetic resonance (¹³C-NMR) spectral data. Compound HL1 (N-(4-nitrobenzoyl)-homoserinelactone) is the optimized insecticidal agent among these compounds. In addition, the antifeedant activities between homoserinelactone and 7-hydroxycoumarin, tutin derivatives with the same acidylated substitutions were compared, which could help design and synthesize stronger novel botanical insecticides.

Keywords:

• Homoserinelactone
• tutin
• 7-hydroxycoumarin
• semisynthesis
• antifeedant activity

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 30872032). We really appreciate Professor Ron Mitchell from Western Kentucky University for language revision assistance.