Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

Shijie Zheng; Xiaomin Lin; Hanxiang Wu; Chen Zhao; Hanhong Xu

doi:10.1186/s13065-020-00673-7

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

BMC Chem. 2020 Mar 30;14(1):22. doi: 10.1186/s13065-020-00673-7. eCollection 2020 Dec.

Authors

Shijie Zheng^#^{1

2}, Xiaomin Lin^#^{1

2}, Hanxiang Wu^{1

2}, Chen Zhao^{1

2}, Hanhong Xu^{1

2}

Affiliations

¹ 1State Key Laboratory for Conservation and Utilization of Subtropical Argo-Bioresources, South China Agricultural University, Guangzhou, Guangdong China.
² 2Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou, 510642 China.

^# Contributed equally.

Abstract

Phloem systemicity is a desirable property for insecticides to control sucking insects. However, the development of phloem systemic insecticides is challenging. One possible strategy is to link existed insecticides with endogenous substances so that the resulting conjugates can be transported by specific transporters into the phloem. In this study, novel dipeptide promoieties were introduced into chlorantraniliprole, which is an efficient and broad-spectrum anthranilic diamide insecticide without phloem mobility. Twenty-two new dipeptide-chlorantraniliprole conjugates have been synthesized. Systemic tests showed that all conjugates exhibited phloem mobility in Ricinus communis. In particular, compound 4g with alanyl-alanine dipeptide fragment was able to accumulate in phloem sap (114.49 ± 11.10 μM) in the form of its hydrolysis product 5g. Results of bioassay showed that conjugates 4g and 5g were able to exhibit comparable insecticidal activity against Plutella xylostella L. and Spodoptera exigua compared to its parent compound chlorantraniliprole. This work demonstrated that the dipeptide structures were able to contribute to the improvement of the uptake and phloem mobility of chlorantraniliprole, and two phloem mobile conjugates with satisfactory in vivo insecticidal effect was obtained as new candidates for high-efficient insecticides.

Keywords: Chlorantraniliprole; Dipeptide; Insecticidal activity; Phloem-mobile pesticides.