Synthesis and fungicidal activity of fluorine-containing chlorothalonil derivatives

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• 作者：Aiying Guan ; Changling Liu ; ^{liuchangling@vip.163.com" class="auth_mail} ; Guang Huang ; Huichao Li ; Shulin Hao ; Ying Xu ; Yong Xie ; Zhinian Li
• 关键词：Fluorine-containing chlorothalonil derivatives ; IDM ; Synthesis ; Fungicidal activity
• 刊名：Journal of Fluorine Chemistry
• 出版年：April, 2014
• 年：2014
• 卷：160
• 期：Complete
• 页码：82-87
• 全文大小：549 K

文摘

Fourteen new fluorine-containing chlorothalonil derivatives were synthesized by using intermediate derivatization method (IDM) in order to discover novel antifungal compounds for controlling corn rust. The structures of synthesized compounds were confirmed by ¹H NMR, ¹³C NMR, ¹⁹F NMR, elemental analysis, HRMS and X-ray. The bioassay results indicated that compound 2,4,5-trichloro-6-(2,6-dichloro-4-[trifluoromethyl]phenylamino)isophthalonitrile (3j, Rⁿ is 2,6-Cl2-4-CF₃) had the optimal structure with best fungicidal activity against corn rust (98%, 70% controls) at 25 and 6.25 mg/L concentration, respectively, much better than chlorothalonil and fluazinam, highlighting the importance of trifluoromethyl group on 4-position of benzene ring. The structure-activity relationship of the synthesized compounds was discussed as well.