Zhu Shouji, Xu Shichao, Jing Wang, Zhao Zhendong, Jiang Jianxin
Institute of Chemical Industry of Forest Products, CAF; Key and Open Laboratory on Forest Chemical Engineering, SFA , Nanjing 210042, China.
Research Institute of Forestry New Technology, CAF , Beijing 100091, China.
J Agric Food Chem. 2016 Dec 28;64(51):9702-9707. doi: 10.1021/acs.jafc.6b03977. Epub 2016 Dec 15.
p-Menth-3-en-1-amine, 4, and its Schiff base derivatives, 5a-l, were designed and synthesized. They were characterized by FT-IR, ESI-MS, HRMS, H NMR, and C NMR spectral analyses, and their pre-emergence herbicidal activities against ryegrass were evaluated. All of the compounds showed excellent herbicidal activity. The Schiff bases showed stronger herbicidal activities than the original amine 4. These compounds showed herbicidal activities comparable to that of glyphosate. The herbicidal activities of 5k and 5l against ryegrass shoot growth were 78.3 and 355.6% higher than that of glyphosate, respectively. Furthermore, the introduction of a chlorine or bromine atom into the Schiff base derivatives containing a furan or benzene ring was beneficial to increase the activity. However, the herbicidal activities were not clearly affected when the heteroatom of the five-membered heterocyclic Schiff base or the position of the substituent on pyridine Schiff base was altered.
对薄荷-3-烯-1-胺（4）及其席夫碱衍生物（5a - l）被设计并合成。通过傅里叶变换红外光谱（FT - IR）、电喷雾电离质谱（ESI - MS）、高分辨质谱（HRMS）、氢核磁共振（¹H NMR）和碳核磁共振（¹³C NMR）光谱分析对它们进行了表征，并评估了它们对黑麦草的苗前除草活性。所有化合物均表现出优异的除草活性。席夫碱显示出比原始胺4更强的除草活性。这些化合物表现出与草甘膦相当的除草活性。5k和5l对黑麦草地上部分生长的除草活性分别比草甘膦高78.3%和355.6%。此外，在含有呋喃或苯环的席夫碱衍生物中引入氯或溴原子有利于提高活性。然而，当五元杂环席夫碱的杂原子或吡啶席夫碱上取代基的位置改变时，除草活性没有受到明显影响。
