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有机化学 ›› 2005, Vol. 25 ›› Issue (08): 949-953. 上一篇    下一篇

研究论文

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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为了寻找高效低毒的原卟啉原氧化酶抑制剂(protox)类除草剂, 设计并合成了一系列1-[5-(1,3-二氧-4,5,6,7-四氢-1H-异吲哚-2-基)苯基]-3-取代脲类衍生物4a～4d和5a～5g. 化合物4a～4d经异氰酸酯法合成, 收率、纯度高; 化合物5a～5g利用固体光气一锅法合成, 反应时间短.所得化合物结构经1H NMR, IR, 质谱和元素分析表征. 初步生物活性测试表明: 化合物4c, 5a, 5b, 5c在有效成分75 g/hm2 剂量下对苘麻、马刺苋、凹头苋等双子叶杂草表现出90%以上的防效.

关键词: 原卟啉原氧化酶抑制剂, 除草活性, 1-[5-(1,3-二酮-4,5,6,7-四氢-1H-异吲哚-2-基)]-3-取代脲, 合成, 固体光气

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