Synthesis and herbicidal evaluation of novel 3-[(alpha-hydroxy-substituted)benzylidene]pyrrolidine-2,4-diones.
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.
Zhu
Youquan
Y
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Zou
Xiaomao
X
Hu
Fangzhong
F
Yao
Changsheng
C
Liu
Bin
B
Yang
Huazheng
H
D015111:4-Hydroxyphenylpyruvate Dioxygenase / Q000037:antagonists & inhibitors; D001597:Benzylidene Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001937:Brassica / Q000254:growth & development; D004791:Enzyme Inhibitors; D006540:Herbicides / Q000138:chemical synthesis / Q000494:pharmacology; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D001597:Benzylidene Compounds; D004791:Enzyme Inhibitors; D006540:Herbicides; D011759:Pyrrolidines; D015111:4-Hydroxyphenylpyruvate Dioxygenase