Design, Synthesis, and Structure–Activity Relationship of New Pyrimidinamine Derivatives Containing an Aryloxy Pyridine Moiety

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• 作者：Aiying GuanChangling Liu ; Wei Chen ; Fan Yang ; Yong Xie ; Jinbo Zhang ; Zhinian Li ; Mingan Wang
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2017
• 出版时间：February 15, 2017
• 年：2017
• 卷：65
• 期：6
• 页码：1272-1280
• 全文大小：450K
• ISSN：1520-5118

文摘

The pyrimidinamine diflumetorim is an ideal template for the discovery of agrochemical lead compounds due to its unique mode of action, novel chemical structure, and lack of reported resistance. To develop a new pyrimidinamine fungicide effective against cucumber downy mildew (CDM), a series of new pyrimidinamine derivatives containing an aryloxy pyridine moiety were designed and synthesized by employing the recently reported intermediate derivatization method (IDM). The structures of all compounds were identified by ¹H NMR, elemental analyses, HRMS, and X-ray diffraction. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against CDM. Compound 9 gave the best activity (EC₅₀ = 0.19 mg/L), which is significantly better than the commercial fungicides diflumetorim, flumorph, and cyazofamid. The relationship between structure and fungicidal activity of the synthesized pyrimidinamines was explored. The study showed that compound 9 is a promising fungicide candidate for further development.