Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group.

Guo-Shao Sun,Le Lin,Xin Xu,Jian-Jun Zhang,Shu-Hui Jin

doi:10.3390/molecules22060958

Abstract

Based on the structural framework of a pyriproxyfen metabolite, nineteen oxime ester derivatives were synthesized via reaction of the carboxylic acids with 4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde oxime. The corresponding structures were comprehensively characterized by 1H-nuclear magnetic resonance (NMR), 13C-NMR, and electrospray ionization high-resolution mass spectrometry (ESI-HRMS). All of the compounds were screened for their insecticidal activities against Plutella xylostella and Myzus persicae, and for their ovicidal activities against Helicoverpa armigera eggs. The results obtained show that most of the oxime ester derivatives displayed moderate to high insecticidal activities and ovicidal activities at a concentration of 600 μg/mL. In particular, the ovicidal activity of compounds 5j, 5o, 5p, 5q, and 5s was determined to be 100%. Importantly, some of the compounds presented even higher biological activities than the reference compound pyriproxyfen. For example, compound 5j displayed an insecticidal activity value of 87.5% against Myzus persicae, whereas the activity value of pyriproxyfen was 68.3% at a concentration of 600 μg/mL. Among the synthesized compounds 5j and 5s exhibited broad biological activity spectra.

Highlights

In the 1930s, various research groups reported that prontosil exhibits a suitable therapeutic effect in mice infected with different bacterial strands
The results were deemed abnormal with respect to the antibacterial activity of prontosil being absent in vitro [1]
The metabolite of prontosil, sulfanilamide, exhibited a strong antibacterial activity in vivo, indicating that the antibacterial activity of prontosil could mainly be attributed to this metabolite [1,2]

Summary

Introduction

In the 1930s, various research groups reported that prontosil exhibits a suitable therapeutic effect in mice infected with different bacterial strands. The results were deemed abnormal with respect to the antibacterial activity of prontosil being absent in vitro [1]. The metabolite of prontosil, sulfanilamide, exhibited a strong antibacterial activity in vivo, indicating that the antibacterial activity of prontosil could mainly be attributed to this metabolite [1,2]. Dozens of sulfonamide species have been developed and used for the treatment of bacterial diseases. The use of drug metabolites as lead compounds has become one of the new drug development approaches widely used in the pharmaceutical industry. Norastemizole (Figure 1), stemming from astemizole (Figure 1), was found to increase selectivity in the process of targeting receptors [3]

Methods

Results

Conclusion