Design,Synthesis and Insecticidal Evaluation of Anthranilic Diamides Containing Optically Pure Amino Acid Moiety |
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| Authors: | Shaa Zhou Sha Zhou Xuewen Hua Wei Wei Yongtao Xie Minggui Chen Xiangde Meng Ming Liu Lixia Xiong Na Yang Baolei Wang Zhengming Li |
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| Institution: | 1. State Key Laboratory of Elemento‐Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, No. 94, Weijin Road, Nankai District, Tianjin 300071, China;2. Shandong Yanhai Construction Resources Co. Ltd, Yantai, Shandong 264000, China;3. Tianjin SPHINX SCIENTIFIC LAB, Tianjin 300457, China |
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| Abstract: | Two series of N‐pyridylpyrazolecarboxamide derivatives were designed and synthesized by introducing D‐alanine acid esters and D‐serine acid esters into the skelecton of chlorantraniliprole. The obtained structures were characterized by 1H NMR, 13C NMR, elemental analysis and specific optical rotation analysis. Preliminary bioassays indicated that some compounds displayed excellent insecticidal activities against Mythimna separate and Plutella xylostella in comparison with chlorantraniliprole. In particular, IIq showed excellent insecticidal activity against Plutella xylostella with a mortality rate of 90% at 0.01 mg·L?1. A 3D‐QSAR (CoMSIA) study was performed in order to disclose the insecticidal structure‐activity relationship and indicate the future work. The CoMSIA study demonstrated that large substitutes and electron deficient groups at the 3‐position of pyrazole ring are favorable, the same as a small group near the ester groups of amino acid. |
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| Keywords: | ryanodine amino acid insecticidal activity |
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