High Value Utilization of an Avermectin Fermentation Byproduct: Novel B2a Derivatives as Pesticide Candidates

Abstract

In an effort to develop novel molecules with suitable insecticidal activities, 23,24-alkene-avermectin B2a derivatives have been synthesized <i>via</i> a one-pot multistep reaction using avermectin B2a, a byproduct of avermectin fermentation, as a starting material. All products and intermediates were characterized by ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry. Bioassay results showed that the LC₅₀ values of compounds <b>4</b> and <b>9</b> against <i>Meloidogyne incognita</i> were 0.63 and 0.50 mg/L, respectively, similar to that of avermectin (0.46 mg/L). Importantly, the LC₅₀ values of compound <b>9</b> against <i>Tetranychus cinnabarinus</i> and <i>Mythimna separate</i> were 0.0067 and 0.047 mg/L, respectively, superior to that of avermectin. Through field experiments, it could be found that spraying 0.25% water-dispersible granules of compound <b>9</b> 345 g ha^-1 could effectively control <i>M. incognita</i> outbreaks, with an efficacy of 84.9%. Combined with toxicity experiments, it could be further inferred that compound <b>9</b> may be useful as a low-toxicity pesticide. In summary, we efficiently synthesized a new B2a derivative as a potential pesticide and offered an important way for improving the utilization efficiency of avermectin fermentation products. In doing so, the environmental pollution associated with fermentation byproducts may be greatly reduced, potentially enabling a sustainable avermectin fermentation process.