Stereoselective Synthesis and Biological Activities of Diethyl (E)-{4-Cyano-5-(disubstitutedamino)methyleneamino-3-(methylthio)-1H -pyrazol-1-ylsubstituited phenylmethyl}phosphonates

摘要

Diethyl (1.5-amino-4-cyano-3-(methylthio)-1H-pyrazol-1-ylsubstitutedphenylmethy l}phosphonates 3 were efficiently synthesized via the condensation of (1-hydrazino)substitutedphenylmethylphosphonates.1 with 2-bis(methylihio)methylenemalononitrile 2. 3 reacted with triethyl orthoformate to afford diethyl (E)-{4-cyano-5-(ethoxymethylene)amino-3-(methylthio)-1H-pyrazol-l-yl substitutedphenylmethylphosphonates 4, which reacted with various secondary arnines at room temperature to provide the target compounds 5 in good yields. Their structures were confirmed by ir, H-1 and P-31 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.