Abstract
2‐Methylthio‐5‐pyridinemethylene amine was prepared from 2‐chloro‐5‐methylpyridine. Ethoxyethyl 2‐cyano‐3,3‐dimethylthioacrylate was prepared from ethoxyethyl cyanoacetate, carbon disulfide, and dimethyl sulfate in 86.2% yield. Its reaction with 2‐methylthio‐5‐pyridinemethylene amine yielded (Z)‐ethoxyethyl 2‐cyano‐3‐methylthio‐3‐(2‐methylthio‐5‐pyridylmethylamino)acrylate. Ethoxyethyl (Z+E)‐2‐cyano‐3‐ethoxyacrylate was synthesized from ethoxyethyl 2‐cyanoacetate and triethyl or‐ thoacetate in 90.7% yield, and its reaction with 2‐ methylthio‐5‐pyridinemethylene amine yielded (Z)‐ethoxyethyl 2‐cyano‐3‐methyl‐3‐(2‐methylthio‐5‐pyri‐dylmethylamino)acrylate. The structures of all of the products were confirmed by ^1^H NMR, elemental analysis, IR, and mass spectroscopy. The herbicidal activities of the products were evaluated, and the results of bioassay showed that (Z)‐ethoxyethyl 2‐cyano‐3‐methyl‐3‐(2‐methylthio‐5‐pyridylmethylamino)acrylate exhibits good herbicidal activity on rape (Brassica napus) at a dose of 1.5 kg/ha. © 2003 Wiley Periodicals, Inc. 15:67–70, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/.hc10214