Synthesis and bioactivity studies of sex pheromone analogs of the diamond back moth, Plutella xylostella

BACKGROUND: Diamondback moth, Plutella xylostella L., is a very important pest of cruciferous vegetables causing excessive economic losses worldwide. Bioactivities of halo-, diazo-, and cyclopropane acetates of P. xylostella sex pheromone have been evaluated using electrophysiology and enzyme inhibition assays. RESULTS: A total of 23 sex pheromone analogs of P. xylostella were designed and synthesized and the result shows that (11Z)-hexadec-11-en-1-yl 2,2,2-trifluoroacetate, (11Z)-hexadec-11-en-1-yl 2,2,3,3,3-pentafluoropropanoate, and (11Z)-hexadec-11-en-1-yl trifluoromethanesulfonate elicited potential inhibitory effects at all doses tested in the electrophysiology and enzyme inhibition assays. Interference of locating the sex pheromone source was found strongest when these three analogs were mixed with the sex pheromone at a 10:1 ratio. In addition, field test showed that the rate of mating disruption was over 90% when (11Z)-hexadec-11-en-1-yl 2,2,2-trifluoroacetate or (11Z)-hexadec-11-en-1-yl 2,2,3,3,3-pentafluoropropanoate was mixed with the sex pheromone at a 10:1 ratio. CONCLUSION: Two sex pheromone antagonists were screen out by electrophysiology, enzyme inhibition assays, wind tunnel and field tests. We believe that these antagonists could be used to establish a novel eco-friendly measure to control P. xylostella and provide evidence for clarifying the specific functions and molecular mechanisms of sex pheromone antagonists. © 2018 Society of Chemical Industry.