化学学报 ›› 1960, Vol. 26 ›› Issue (1): 1-6.    下一篇

论文

三取代硫脲的合成

何炳林, 杨华铮, 方苏南   

  1. 南开大学化学系
  • 投稿日期:1959-05-03 发布日期:2013-06-03

THE SYNTHESIS OF TRISUBSTITUTED THIOUREAS

HO PING-LUM, YANG HUA-CHENG, FANG SU-NAN   

  1. Department of Chemistry, Nankai University
  • Received:1959-05-03 Published:2013-06-03

应用芳伯胺、二甲胺、二硫化碳及少量粉状氢氧化钠在乙醇溶液内反应,可制成多种三取代硫脲,其中3-(对氯苯基)-1,1-二甲基硫脲为优良的除莠剂,经试验证明其效力与3-(对氯苯基)-1,1-二甲基脲相仿,惟杀草所需时间要长些,但易溶于乙醇及其他价廉的有机溶剂.2-硝基苯胺、2,4-二硝基苯胺、2-羟基苯胺及2-氨基吡啶与二硫化碳及二甲胺作用均得不到硫脲衍生物,可能是由于苯环上的硝基或羟基与邻位的胺基生成五环或六环内络合物.2-氨基吡啶的结构与酰胺相似,氨基上的氢原子可与环上的氮进行互变异构作用也不生成硫脲.若在氨基邻位上有一较大的基团,则产率大受影响,这可能是由于“位阻”所致.

In 1951,Bucka and Todd[1] found that 3-(p-chlorophenyl)-1,1-dimethylurea (CMU) is an outstanding weed killer. It is highly toxic to many plants and possesses long-lasting herbicidal effect in the soil. In 1953,Sharp et al[2] found that 1,1-dimethyl-3-phenylurea is effective in eradicating deep-rooted perennial weeds in croplands. However,it persists in soil as a sterilant for a shorter period than 3-(p-chlorophenyl)-1,1-dimethylurea. Since the structure of 3-(p-chloro-phenyl)-1,1-dimethylurea is similar to that of CMU, the senior author synthesized and tested it in Nalco* in 1953 as a herbicide. It was found to be as effective to plants as 3-(p-chlorophenyI)-1,1-dimethylurea. However,it took a longer period for the herbicidal effect.