Design, Synthesis, and 3D-QSAR Analysis of Novel 1,3,4-Oxadiazol-2(3H)-ones as Protoporphyrinogen Oxidase Inhibitors

作者：Jiang, Li-Li; Ying Tan; Zhu, Xiao-Lei; Wang, Zhi-Fang; Yang Zuo; Qiong Chen; Zhen Xi^*; Yang, Guang-Fu

来源：Journal of Agricultural and Food Chemistry, 2010, 58(5): 2643-2651.

DOI：10.1021/jf9026298

• Protoporphyrinogen oxidase
• 1,3,4-oxadiazol-2(3H)-ones
• benzothiazole
• herbicide

Protoporphyrinogen oxidase (PPO, EC 1.3.3,4) has been identified as one of the most significant action targets for a large chemically diverse family of herbicides that exhibit some interesting characteristics, such as low use rate, low toxicity to mammals, and low environmental impact. As a continuation of research work on the development of new PPO inhibitors, some benzothiazole analogues of oxadiargyl, an important PPO-inhibiting commercial herbicide, were designed and synthesized by ring-closing of the substituents at the C-4 and C-5 positions. The bioassay results indicated that the series 8, 9, and 10 have good PPO inhibition activity with k(i) values ranging from 0.25 to 18.63 mu M. Most interestingly, 91, ethyl 2-((5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)sulfanyl) propanoate, was identified as the most promising candidate due to its high PPO inhibition effect (k(i) = 1.42 mu M) and broad spectrum postemergence herbicidal activity at the concentration of 37.5 g of ai/ha.

• 单位
  华中师范大学; 元素有机化学国家重点实验室; 南开大学