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Citation: WANG Ying, YANG Feng-Ling, LIU Zhao-Jie. Syntheses and Bioactivities of Imidazolinone Schiff Bases[J]. Chinese Journal of Applied Chemistry, ;2004, 21(11): 1105-1108. shu

Syntheses and Bioactivities of Imidazolinone Schiff Bases

1.
College of Chemistry, Central China Normal University, Wuhan 430079

Corresponding author: LIU Zhao-Jie,
Received Date: 1 December 2003
Available Online: 19 April 2004
Fund Project: 科技部国家"九五"重点攻关项目(975630205) (975630205)

Ten novel Schiff bases of imidazolinone were synthesized. Vinyliminophosphorane reacted with carbon disulfide and hydrazine hydrate via tandem aza-Witting reactions to give 3-amino-2-thio-4-imidazolidinones 4. In the presence of potassium carbonate, iodomethane reacted with 3-amino-2-thio-4-imidazolidinones 4 to give 3-amino-5-benzylidene-2-methylthio-imidazolin-4-one 5, which condensed with arylaldehydes to give 3-benzylimino-2-methylthio-5-benzylidene imidazolin-4-one 6. The structures of compounds 6 were confirmed by elemental analysis, ¹H NMR, IR and MS. The preliminary biological tests show that most of compounds 6 have good herbicidal activities to monocotyledon Barnyard grass and dicotyledon Cole. Compound 6h, 2-methylthio-5-benzylidene-3-(3'-chloro-benzyl)-imino-imidazoli-4-one exhibits 100% inhibition against Cole root and stalk, Barnyard grass root in 100 mg/L.
- Schiff base,
- imidazolinone,
- tandem aza-Wittig reaction,
- synthesis,
- herbicidal activity
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