Design, synthesis and herbicidal activities of (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol derivatives

作者：Huang, Daozhan; Zhu, Shouji^*; Lan, Hongyun; Lin, Zhinan; Wang, Xiaoshu

来源：Industrial Crops and Products, 2019, 129: 24-34.

DOI：10.1016/j.indcrop.2018.11.065

• Ester derivatives
• Ether derivatives
• Botanical herbicides
• Herbicidal activity
• (3R, 4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1] octane-3,4-diol

The chemosynthesis and potential as green herbicides of the derivatives of (3R,4R)-4,7,7-trimethyl-6-oxabicyclo [3.2.1]octane-3,4-diol (compound 2) were emphatically addressed in this work. First, the ester and ether derivatives of (3R,4R)-4,7,7-trimethyl-6- oxabicyclo[3.2.1]octane-3,4-diol (compound 2) were synthesized and structurally characterized by infrared spectroscopy, high-resolution mass spectrometer, and proton nuclear magnetic resonance. Then, the post-emergence herbicidal activities of these compounds against Lolium multi-florum Lam. (annual ryegrass) and Raphanus sativus L. (radish) were evaluated. All the compounds exhibited remarkable herbicidal activity. The IC50 of these compounds against the root and shoot growths of annual ryegrass and radish were in the range of 0.11-1.34 mmol L-1. Both the ester and ether derivatives displayed much stronger herbicidal activities than compound 2. Some of these compounds showed comparable herbicidal activities to the commercial herbicide glyphosate. The herbicidal activities of 3b, 3c, and 3d against ryegrass shoot growths were 272.7%, 173.3%, and 241.7% higher than that of glyphosate, respectively. Furthermore, comparing the herbicidal activities between the ester derivatives and the ether derivatives, no strong relationship was observed. The results indicated that these compounds could be environmentally acceptable herbicides.

• 出版日期2019-3
• 单位广西民族大学; 广西大学; 韩山师范学院