Tetrafluorobenzyl Alcohol-Oriented Novel (S)-Enantiomeric Esters: Synthesis and Structure-Activity Relationship

Abstract

Background: Using constantly and widely chemistry insecticides has resulted in a selection burden and favored tolerance development in various insect species. Particularly, pyrethroids are the only one which can be used for net impregnation either ITNs or LLIN as yet, however, the excessive use of pyrethroids has led to many cases of insect resistance in worldwide. Therefore, it is urgent to develop novel insecticides fighting against this sort of resistance. Methods: Based on the preliminary studies, we explored a straightforward highly stereoselective method to achieve the novel chiral ester derivatives by using Oppolzer’s 10,2-camphorsultam as chiral controlling reagent. Results: A series of tetrafluorobenzyl alcohol oriented (S)-enantiomeric esters were designed and synthesized by the asymmetric synthesis. All the compounds exhibited moderate yields, and the original synthesized compounds have been evaluated for their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and D-trans-phenothrin, and some compounds presented excellent insecticidal activities. Conclusion: The bioassay illustrated that some of the compounds exhibit obviously insecticidal activities against Plutella xylostella, especially, the insecticidal activity of compound 5i was as good as commercial fenvalerate and D-trans-phenothrin, which can be used as a lead compound for further optimization.