Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties
Received date: 2014-12-15
Revised date: 2015-03-14
Online published: 2015-03-19
Supported by
Project supported by the National Natural Science Foundation of China (No. 20772068).
Two series of 2-cyanoacrylates containing 4-(6-chloropyridin-3-yl)methoxy-benzylamine moieties were synthesized as herbicides using 2-cyano-3-(pyridine-3-yl)aminoacrylates as precursor compound. The structures were confirmed by 1H NMR, 13C NMR, Elemental Analysis or High-Resolution Mass spectrometry (HRMS). The herbicidal activity tests showed that most of the target compounds had good inhibition towards dicotyledonous weeds. Compounds 13e and 13g showed 100% herbicidal activity at the dose of 375g/ha against rape, and compound 13e showed 100% herbicidal activity against rape even at the dose of 187.5 g/ha. From the structure-activity relationship study, it can be primarily concluded that both the contributions of the electronic and steric effects of the phenyl group are very important to the herbicidal activity.
Wu Shanshan , Miao Wenke , Wang Tingting , Fang Jianxin . Synthesis and Herbicidal Activities of 2-Cyanoacrylates with 4-(6-Chloropyridin-3-yl)methoxy-benzylamine Moieties[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1484 -1492 . DOI: 10.6023/cjoc201412025
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