High value-added application of rosin as a potential renewable source for the synthesis of acrylopimaric acid-based botanical herbicides
High value-added application of rosin as a potential renewable source for the synthesis of acrylopimaric acid-based botanical herbicides
复制标题
松香作为潜在可再生资源用于合成丙烯海松酸类植物除草剂的高附加值应用
DOI：
10.1016/j.indcrop.2015.10.032
复制
发表时间：
2015-12-30
影响因子：
5.9
通讯作者：
Xiao, Guomin
中科院分区：
文献类型：
--
作者：
Gao, Yanqing;Li, Lingli;Xiao, Guomin
Turning natural products into value-added herbicide preparation is an alternative to synthetic compounds for environmentally friendly weed management. In continuation of our research on rosin-based herbicidal agents, 33 acrylopimaric acid (APA) derivatives were synthesized, and were structurally characterized using proton nuclear magnetic resonance, elemental analysis, electrospray ionization mass spectra, melting point, infrared spectroscopy, and X-ray crystallography. In addition, the herbicidal activity of APA derivatives against Amaranthus retroflexus, Echinochloa crus-galli, and Brassica campestris L. were investigated. Among the AFA derivatives, the diacylthiourea compounds 3a-f showed significant post-emergence herbicidal activity against E. crus-galli. Moreover, compounds 3b d (with EC50 values of 13.191, 13.441, and 13.191 g ai/ha, respectively) displayed more promising herbicidal activity against E. crus-galli than sulfentrazone (a commercial herbicide with an EC50 value of 15.606 g ai/ha). In quantitative structure activity relationship (QSAR) study, optimal conformers and best multilinear regression analysis were performed using Gaussian and CODESSA software. The four descriptors correlating the molecular structures with their herbicidal activities were as follows: Total Charge, log MS, q(max)(N) and q(max)(C). The generated QSAR model had a correlation coefficient of 0.9625, a Fisher significance ratio of 185.96, and a squared standard error of the estimates of 0.0012. Preliminary studies on the structure activity relationship and QSAR showed that the higher electron density around the substituent groups on the nitrogen atoms of rosin-based backbone structure and smaller volume of spatial structure played a beneficial effect on the herbicidal activity. Thus, rosin is a promising source of a value-added product for crop protection. (C) 2015 Elsevier B.V. All rights reserved.
