Design, synthesis and insecticidal activities of novel 1-substituted-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives

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• 作者：Zhi-Bing Wu^a ; Xiang Zhou^a ; Yi-Qiang Ye^a ; Pei-Yi Wang^a ; Song Yang^a ; ^b ; ^{jhzx.msm@gmail.com}
• 关键词：5-(Trifluoromethyl)-1H-pyrazole-4-carboxamide ; Insecticidal activities ; Chlorantraniliprole ; Ryanodine receptors
• 刊名：Chinese Chemical Letters
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：28
• 期：1
• 页码：121-125
• 全文大小：711 K
• 卷排序：28

文摘

A series of novel 5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives (6a–6n, 7a, 7b, and 8a-8f) were synthesised by placing the amide bond at the 4-position of the pyrazole ring. These derivatives differed from the structure of chlorantraniliprole analogues with the amide bond at the 5-position of the pyrazole ring. Preliminary bioassay results revealed that a few title compounds exhibited good insecticidal activities against lepidopteran pests, such as Plutella xylostella, Mythimna separate, Heliothis armigera, and Ostrinia nubilalis. Some title compounds also elicited broad-spectrum insecticidal activities against dipterous insects including Culex pipiens pallens after altering the amide position. Similar to pyrazole-5-carboxamide analogues, compounds 6b and 6e showed 100% insecticidal activity against P. xylostella, C. pipiens pallens, and M. separate at concentrations of 200, 2, and 200 μg/mL, respectively. This finding suggested that 5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives are potential alternative insecticides for management of agriculture pests.