新型含噁唑环结构的氰基丙烯酸酯类衍生物的合成及其生物活性研究
收稿日期: 2018-05-16
修回日期: 2018-06-27
网络出版日期: 2018-06-29
基金资助
国家自然科学基金（No.21372135）、江苏省"六大人才高峰"（No.2013-SWYY-013）、南通市科技计划（No.MS22015020）和江苏省大学生创新训练计划（No.201810304016Z）资助项目.
Synthesis and Biological Activity of New Cyanoacrylate Compounds Bearing Oxazole Moiety
Received date: 2018-05-16
Revised date: 2018-06-27
Online published: 2018-06-29
Supported by
Project supported by the National Natural Science Foundation of China (No. 21372135), the Research Foundation of the Six People Peak of Jiangsu Province (No. 2013-SWYY-013), and the Science and Technology Project Fund of Nantong City (No. MS22015020) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201810304016Z).
为了从氰基丙烯酸酯类衍生物中寻找新的活性化合物，通过活性基团拼接方法，设计合成了一系列新型含噁唑环结构的氰基丙烯酸酯化合物.初步的除草活性测试结果表明，大部分标题化合物具有较好的除草活性.在剂量为750 g/ha时，部分化合物对芥菜的除草活性可达80%~100%，对小藜的抑制率可达90%~100%，对酸模的除草活性可达80%~100%.2-氰基-3-甲硫基-3-{[4-（2-（4-氟苯基）噁唑-4-基）甲硫基]-苯甲基胺基}丙烯酸（2-甲氧基）乙酯（11a）和2-氰基-3-甲硫基-3-{[4-（2-（3，4-二氟苯基）噁唑-4-基）甲硫基]-苯甲基胺基}丙烯酸（2-甲氧基）乙酯（11e）对看麦娘的除草活性分别为70%和60%，对棒头草的抑制率分别为70%和60%.化合物11a对早熟禾的抑制率为70%.此外，化合物11a在150 g/ha剂量下对芥菜和酸模的抑制率均达40%.
周家华 , 戴红 , 钱宏炜 , 杜显超 , 茅心宇 , 石玉军 , 冯浩 , 石健 , 姚勇 . 新型含噁唑环结构的氰基丙烯酸酯类衍生物的合成及其生物活性研究[J]. 有机化学, 2018 , 38(8) : 2122 -2129 . DOI: 10.6023/cjoc201805036
In order to find novel cyanoacrylate derivatives possessing potent bioactivities, a series of novel cyanoacrylates bearing substituted oxazole unit were designed and prepared. The bioassay data indicated that most title compounds had satisfactory herbicidal activities. At the dosage of 750 g/ha, some compounds showed herbicidal activity against Brassica juncea with 80%~100%, Chenopodium serotinum L. with 90%~100%, and Rumex acetosa L. with 80%~100%. 2-Cyano-3-me-thylthio-3-{[4-(2-(4-fluorophenyl)oxazole-4-yl)methylthio]-benzylanimo}acrylic acid (2-methoxy)ethyl ester (11a) and 2-cyano-3-methylthio-3-{[4-(2-(3,4-difluorophenyl)oxazole-4-yl)methylthio]-benzylanimo}acrylic acid (2-methoxy)ethyl ester (11e) displayed herbicidal activity against Alopecurus aequalis Sobol with 70% and 60%, and Polypogon fugax Nees ex Steud with 70% and 60%. Compound 11a showed herbicidal activity against Poa acroleuca Steud with 70%. In addition, the inhibitory rates of compound 11a against Brassica juncea and Rumex acetosa L. were both 40% at the dosage of 150 g/ha.
Key words： cyanoacrylate; oxazole unit; preparation; biological activity
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