Design and Syntheses of Novel Phthalazin-1(2H)-one Derivatives as Acetohydroxyacid Synthase Inhibitors

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• 作者：Yuan-Xiang Li ; Yan-Ping Luo ; Zhen Xi ; Congwei Niu ; Yan-Zhen He ; Guang-Fu Yang
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2006
• 出版时间：November 29, 2006
• 年：2006
• 卷：54
• 期：24
• 页码：9135 - 9139
• 全文大小：105K
• 年卷期：v.54,no.24(November 29, 2006)
• ISSN：1520-5118

文摘

A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives, 7a-7w, were designed via an ortho-substituent cyclization strategy to discover a new herbicidal leadstructure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenoneas a starting material. Determination of the K_i values against wild-type A. thaliana acetohydroxyacidsynthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzymeinhibition activity comparable to that of KIH-6127. The further preliminary bioassay data on weedsshowed that the synthesized compounds exhibited typical injury symptoms of AHAS-inhibitingherbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergencetreatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea,Amaranthus retroflexus, and Chenopodium album at an application rate of 150 g ai/ha. To ourknowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.