Structural modification of (3E)-4,8-dimethyl-1,3,7-nontriene enhances its ability to kill Plutella xylostella insect pests.

Abstract

Plant secondary metabolites and their modified derivatives play an important role in the discovery and development of novel insecticides. The natural plant product (3E)-4,8-dimethyl-1,3,7-nontriene (DMNT) has been proven to be able to effectively repel and kill the lepidopteran insect pest Plutella xylostella. In this study, four oxygenated derivatives of DMNT were synthesized by allylic hydroxylation and subsequent etherification or esterification. Bioassays on P. xylostella larvae showed that the compounds DMNT-OCH3 (2), DMNT-OCy (3) and DMNT-OAc (4) were more toxic to the larvae than DMNT alone. The most pronounced effect was observed for compound 2, which showed a 22.23% increase in lethality at a concentration of 0.25 μm. Moreover, the peritrophic matrix (PM) barrier in the insect midgut was more severely damaged by compounds 2, 3 and 4 than by DMNT. The median lethal concentration (LC50 , 48 h) of compounds 2, 3 and 4 on P. xylostella was determined to be 0.98, 1.13 and 1.11 mg mL-1 , respectively, which is much lower than the commercial insecticides eucalyptol (2.89 mg mL-1 ) and thymol (2.45 mg mL-1 ). These results suggested that oxygenated DMNT derivatives offer a significantly improved killing effect over DMNT on P. xylostella. This work has provided a basis for further design, structural modification and development of DMNT as botanical insecticides. © 2023 Society of Chemical Industry.