| 19954223 |
Jiang LL, Tan Y, Zhu XL, Wang ZF, Zuo Y, Chen Q, Xi Z, Yang GF: Design, synthesis, and 3D-QSAR analysis of novel 1,3,4-oxadiazol-2 (3H)-ones as protoporphyrinogen oxidase inhibitors. J Agric Food Chem. 2010 Mar 10;58(5):2643-51.
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 microM. Most interestingly, 9l, 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 microM) and broad spectrum postemergence herbicidal activity at the concentration of 37.5 g of ai/ha. |
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