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Design, synthesis and herbicidal activities of (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol derivatives
Industrial Crops and Products ( IF 5.6 ) Pub Date : 2018-12-03 , DOI: 10.1016/j.indcrop.2018.11.065
Daozhan Huang , Shouji Zhu , Hongyun Lan , Zhinan Lin , Xiaoshu Wang

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 multiflorum 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.



中文翻译:

(3 R, 4 R)-4,7,7-三甲基-6-氧杂双环[3.2.1]辛烷-3,4-二醇衍生物的设计,合成和除草活性

着重论述了(3 R,4 R)-4,7,7-三甲基-6-氧杂双环[3.2.1]辛烷-3,4-二醇(化合物2)衍生物的化学合成和作为绿色除草剂的潜力。这项工作。首先,合成了(3 R,4 R)-4,7,7-三甲基-6-氧杂双环[3.2.1]辛烷-3,4-二醇(化合物2)的酯和醚衍生物,并通过红外对其结构进行了表征光谱学,高分辨率质谱仪和质子核磁共振。然后,这些化合物对多花黑麦草的芽后除草活性(一年生黑麦草)和萝卜Raphanus sativus L.(萝卜)进行了评价。所有化合物均表现出显着的除草活性。这些化合物对一年生黑麦草和萝卜根和芽生长的IC 50范围为0.11-1.34 mmol L -1。酯和醚衍生物都显示出比化合物2强得多的除草活性。这些化合物中的一些显示出与市售除草剂草甘膦相当的除草活性。3b3c3d的除草活性黑麦草的抗性分别比草甘膦高272.7%,173.3%和241.7%。此外,比较酯衍生物和醚衍生物之间的除草活性,没有观察到很强的关系。结果表明这些化合物可能是环境可接受的除草剂。

更新日期:2018-12-03
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