Design, Synthesis, Biological Evaluation and SARs of Anthranilic Diamide Derivatives Containing Pyrrole Moieties
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doi: 10.1007/s40242-020-0237-5
Article
Design, Synthesis, Biological Evaluation and SARs of Anthranilic Diamide Derivatives Containing Pyrrole Moieties ZHAO Yangyang, LI Huangong, SUN Pengwei, GAO Li, ZHOU Sha, XIONG Lixia, YANG Na, LI Yuxin* and LI Zhengming * State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China Abstract In order to find a new variety of ryanodine receptor(RyR) regulator with greater biological activity, a series of anthranilic diamide derivatives possessing pyrrole structure was designed and synthesized in this study. The pyrrole derivatives were evaluated for their insecticidal activity against Mythimna separata and Plutella xylostella. As indicated by the preliminary biological activities, compounds 12h―12j and 12l―12n exhibited a remarkable insecticidal activity against M. separata at 0.25 mg/L. Compared to control chlorantraniliprole, compound 12j exhibited more excellent insecticidal activity at 0.1 mg/L. Meanwhile, compounds 12c, 12h, 12i, 12j, 12l, and 12m were selected to test the insecticidal activity against P. xylostella, which led to the desirable insecticidal activity at 1×10 –3 mg/L. Notably, compound 12l demonstrated 47% insecticidal activity at 5×10–6 mg/L over the control. In addition, the biological mechanism of action of compound 12j was investigated by means of insect electrophysiology experiment. Keywords Ryanodine receptors(RyRs) activator; Pyrrole; Anthranilic diamide; Insecticidal activity; Mechanism of action
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Introduction
Insect pests have posed a serious threat to the security of crop production. Not only could they cause a substantial amount of economic losses, they can also jeopardize food security for both households and the whole country[1,2]. To ensure the sufficient supply of high-quality food, many agrochemicals have already been widely applied to carrying out pest control[3]. Over the course of search for novel pesticides, plenty of researches have been conducted to find out that the anthranilic diamides compounds classed into ryanodine receptor(RyR) modulators are effective in regulating the release of calcium ion. Subsequently, it was discovered that chlorantraniliprole was a compound capable of high insecticidal activity against lepi-
Fig.1
dopteran pests. In 2008, it was put on the market by DuPont[4]. In order to improve the agrochemical properties of chlorantraniliprole, some studies have been carried out recently to achieve structural modification. At present, there have been a few variety of commercial diamide insecticide compounds launched successively, for example, cyantraniliprole, tetrachlorantraniliprole and cyclaniliprole, as shown in Fig.1(A), which illustrates a broad spectrum of biological activities in the control over various insects[5,6]. Thus, it has opened up a new possibility for the commercialized synthesis of anthranilic diamides. It is already known that biologically active pyrroles and the compounds structurally related to them are naturally
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