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Synthesis and Herbicidal Activity of 2-Cyano-3-substituted-pyridinemethylaminoacrylates

Author:
Wang, Qingmin, Sun, Huikai, Cao, Huanyan, Cheng, Muru, Huang, Runqiu
Source:
Journal of agricultural and food chemistry 2003 v.51 no.17 pp. 5030-5035
ISSN:
0021-8561
Subject:
electron transfer, herbicidal properties, herbicides, nuclear magnetic resonance spectroscopy, photosystem II, China
Abstract:
Two series of 2-cyano-3-substituted-pyridinemethylaminoacrylates, namely 12 new (Z)-2-cyano-3-methylthio-3-substituted-pyridinemethaneaminoacrylates and 10 new (Z)-2-cyano-3-alkyl-3-substituted-pyridinemethaneaminoacrylates, were synthesized as herbicidal inhibitors of photosystem II (PSII) electron transport. All of these compounds were confirmed by 1H NMR, elemental, IR, and mass spectrum analyses. Their herbicidal activities were evaluated. Some compounds exhibited excellent herbicidal activities, even at a dose of 75 g/ha. A suitable substituent at the 2-position of the pyridine ring and the well-fit group at the 3-position of acrylate were essential for high herbicidal activity. 2-Cyanoacrylates containing a substituted pyridine ring provide higher herbicidal activities than parent compounds containing phenyl. These PSII inhibitor herbicides are safe to corn, which is a major crop in China.
Agid:
322117