文献类型：期刊文献

英文题名：Structural Modification of Turpentine with Natural Chiral Preservation and Low-Risk Application Prospects in Crop Protection

作者：Gao, Yanqing[1] Hao, Jin[1] Li, Jian[2] Song, Zhanqian[3] Shang, Shibin[3]

第一作者：Gao, Yanqing

通信作者：Li, J[1]

机构：[1]Northwest A&F Univ, Coll Plant Protect, 3 Taicheng Rd, Yangling 712100, Shaanxi, Peoples R China;[2]Northwest A&F Univ, Coll Forestry, 3 Taicheng Rd, Yangling 712100, Shaanxi, Peoples R China;[3]Chinese Acad Forestry, Inst Chem Ind Forest Prod, 16 Suojin Wucun, Nanjing 210042, Jiangsu, Peoples R China

年份：2019

卷号：4

期号：4

起止页码：6392-6398

外文期刊名：ACS OMEGA

收录：;Scopus(收录号：2-s2.0-85064129269);WOS:【SCI-EXPANDED(收录号:WOS:000466552500034)】；

基金：This work was supported by the National Key R&D Program of China (grant number 2018YFD0600402), the National Natural Science Foundation of China (grant number 31870555), and the Young Talent Cultivation Plan of Northwest A& F University (grant number 2452018031).

语种：英文

摘要：For the purpose of chiral pesticide development, the natural chiral structure of turpentine should be applied rationally. Two series of amide derivatives were prepared to study the effect of chiral center retention on the fungicidal activity. The investigation of fungicidal activity against three pathogenic microbes was carried out extensively. Some satisfactory conclusions were obtained from the activity evaluation. Above all, compounds (5'a-l) derived from cis-myrtlecanic acid (a chiral compound obtained from beta-pinene) exhibited better activity than compounds (5a-l) derived from dehydrocumic acid (achiral compound obtained from beta-pinene). The overall effect was good, and it was remarkable that compounds 5'd (substitute with N-(4-(trifluoromethyl)phenyl), 5'e (substitute with N-(4-fluorophenyl)), and 5'f (substitute with N-(4-chlorophenyl)) demonstrated extremely excellent activity, with EC50 values of 1.604, 1.822, and 2.296 mu g/mL against Valsa mali. The above three compounds also showed a good control effect against V. mali in vitro on an apple branch. Treatment with 5'd, 5'e, and 5'f against V. mali resulted in significantly influenced physiological and biochemical indices, as well as markedly reduced pectinase activity in comparison with untreated controls. The preliminary structure-activity relationship (SAR) was summarized, showing that compounds obtained with chiral centers, a halogen atom, and small steric hindrance showed better performance. At the same time, the quantitative structure-activity relationship (QSAR) model (R-2 = 0.9288, F = 62.01, S-2 = 0.0138) was obtained, and two most important structural features were maximum net atomic charge for a F atom and shadow indices. Guided by this study, the highly efficient, low-toxicity, and environmentally friendly fungicide can be prepared through reasonable modification of terpene.