Chinese Journal of Organic Chemistry >
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).
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
Zhou Jiahua , Dai Hong , Qian Hongwei , Du Xianchao , Mao Xinyu , Shi Yujun , Feng Hao , Shi Jian , Yao Yong . Synthesis and Biological Activity of New Cyanoacrylate Compounds Bearing Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, 2018 , 38(8) : 2122 -2129 . DOI: 10.6023/cjoc201805036
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