Stereoselective synthesis and biological activities of diethyl (E)-{[4-cyano-5-[[(disubstitutedamino)methylene]amino]-3-(methylthio)- 1H-pyrazol-1-yl]substituited phenylmethyl}phosphonates

✍ Scribed by Lin-Xia Xiao; De-Qing Shi

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 136 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.97

✦ Synopsis

Abstract

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Diethyl {[5‐amino‐4‐cyano‐3‐(methylthio)‐1__H__‐pyrazol‐1‐yl]substitutedphenylmethyl}phosphonates 3 were efficiently synthesized via the condensation of [(1‐hydrazino)substitutedphenylmethyl]phosphonates 1 with 2‐[bis(methylthio)methylene]malononitrile 2. 3 reacted with triethyl orthoformate to afford diethyl (E)‐{[4‐cyano‐5‐[(ethoxymethylene)amino]‐3‐(methylthio)‐1__H__‐pyrazol‐1‐yl]substitutedphenylmethyl}phosphonates 4, which reacted with various secondary amines at room temperature to provide the target compounds 5 in good yields. Their structures were confirmed by ir, ^1^H and ^31^P NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassay indicated that compounds 5 possess potent herbicidal activity against the roots of dicotyledonous (oil rape) plants at the dosage of 100 mg/L, and compounds 5c and 5g exhibit 80.8% and 76.7% inhibitory activity against Colletotrichum gossypi at the concentration of 50 mg/L, respectively. Abstract end data: J. Heterocyclic Chem., 46, 555 (2009).