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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (08): 949-953. Previous Articles     Next Articles

Original Articles

1-[5-(1,3-二氧-4,5,6,7-四氢-1H-异吲哚-2-基)苯基]-3-取代脲衍生物的合成与除草活性研究

黄明智*，程辟，黄可龙，任叶果
雷满香，马扬光，徐满才*   

  1. (1中南大学化学化工学院 长沙410083)
    (2湖南化工研究院 长沙 410007 )
    (3湖南师范大学化学化工学院 长沙 410081 )
  • 收稿日期:2004-11-24 修回日期:2005-02-28 发布日期:2005-07-30
  • 通讯作者: 黄明智

Synthesis and Herbicidal Activity of 1-[5-(1,3-Dioxo-4,5,6,7-tetra- hydro-1H-isoindol-2-yl)phenyl]-3-substituted Urea Derivatives

HUANG Ming-Zhi*,CHENG Pi,HUANG Ke-Long,REN Ye-Guo
LEI Man-Xiang,MA Yang-Guang,XU Man-Cai*   

  1. (1 College of Chemistry and Chemical Engineering, Central South University, Changsha 410083)
    (2 Hunan Research Institute of Chemical Industry, Changsha 410007)
    (3 College of Chemistry and Chemical Engineering, Hunan Normal Univer-sity, Changsha 410081)
  • Received:2004-11-24 Revised:2005-02-28 Published:2005-07-30
  • Contact: XU Man-Cai

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In order to discover novel herbicides inhibiting protoporphyrinogen oxidase (protox) with high activity and low toxicity, a series of 1-(5-(1,3-dioxo-4,5,6,7- tetrahydro-1H-isoindol-2-yl)phenyl)-3-substi- tuted urea derivatives 4a～4d and 5a～5g were designed and synthesized. Compounds 4a～4d were prepared by the reaction of substituted phenyl amine with aryl isocyanate in high purity and yield, and 5a～5g were obtained by the reaction of substituted phenyl amine with triphosgene and alkyl amine in one pot for a short time. Their structures were confirmed by 1H NMR, IR, MS spectra and elemental analyses. The primary bioassay results showed that compounds 4c, 5a, 5b and 5c exhibited control efficacy of more than 90% against Abutilon avicennae, Portulaca oleracea, and Amaranthus spinosus at 75 g/hm2.

Key words: protox inhibitor, triphosgene, herbicidal activity, synthesis, 1-[5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2-yl)-phenyl]-3-substituted urea