Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 159-166.DOI: 10.6023/cjoc201408006 Previous Articles     Next Articles



张浩a, 李奇博a, 刘克昌a, 刘瑞全a, 李青阳a, 汪清民b, 刘尚钟a   

  1. a 中国农业大学理学院应用化学系 北京 100193;
    b 南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2014-05-12 修回日期:2014-08-01 发布日期:2014-09-16
  • 通讯作者: 汪清民, 刘尚钟
  • 基金资助:

    辽宁省自然科学基金(No. 20102126)资助项目.

Synthesis and Herbicidal Activity of N-(4-Chloro-2-fluoro-5- substituted phenyl)isoindole-1,3-dione Derivatives

Zhang Haoa, Li Qiboa, Liu Kechanga, Liu Ruiquana, Li Qingyanga, Wang Qingminb, Liu Shangzhonga   

  1. a Department of Applied chemistry, College of Science, China Agricultural University, Beijing 100193;
    b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
  • Received:2014-05-12 Revised:2014-08-01 Published:2014-09-16
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

In order to find new herbicidal leading compounds, a series of N-(4-chloro-2-fluoro-5-substituted phenyl)-isoindole-1,3-dione derivatives (6a6f, 7a7k) were designed and synthesized via the strategy of linking active sub-structures which are chlorophthalim and phenoxy carboxylic ester. The target compounds were synthesized from starting material 2-chloro-4-fluoro-5-nitrophenol in four steps, and their structures were confirmed by 1H NMR, 13C NMR and HRMS. The preliminary bioassay results indicated that most compounds exhibited excellent herbicidal activities at 1500 g/ha in both pre- and post-emergence treatments against Abutilon theophrasti and Amaranthus retroflexus. On the basis of advanced screening tests, compound 6d exhibited 100% inhibitory effect against Abutilon theophrasti and Amaranthus retroflexus at 750 g/ha, compounds 7a and 7i were much more effective against Abutilon theophrasti than commercial acifluorfen with 80%~86% inhibitory activity at 22.5 g/ha.

Key words: protoporphyrinogen oxidase inhibitor, N-phenyl isoindole-1,3-dione, phenoxy carboxylic ester, herbicidal activity