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Synthesis and herbicidal evaluation of novel 3-[(alpha-hydroxy-substituted)benzylidene]pyrrolidine-2,4-diones
Youquan Zhu1, Xiaomao Zou, Fangzhong Hu
1State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Abstract:
A series of 3-[(alpha-hydroxy-substituted) benzylidene]pyrrolidine-2,4-dione derivatives were synthesized as candidate herbicides by reacting different aroyl acetates with N-substituted glycine esters. The new compounds were identified by 1H NMR spectroscopy and elemental analyses. Their herbicidal activities were evaluated. Some compounds exhibited excellent herbicidal activities at a dose of 187.5 g/ha. A suitable electron-donating substituent at the 2- and/or 4-position of the phenyl ring was essential for high herbicidal activity, a result that has not been reported before. It was also found that the title compound's structure-activity relationships were different from those of other similar kinds of earlier compounds, a result that may depend on the enol structure difference.
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