Synthesis and Properties of Novel Imidazolone Derivatives Containing a Sulfur Atom

Abstract

Novel 5-(2-chlorophenylmethylidene)-2-thio-4-imidazolinones 3 and 2-Alkythio-5-(2-chlorophenylmethylidene)-4H-imidazolin-4-ones 4 have been synthesized via a tandem aza-Wittig reaction to develop more imidazolinones that may possess biological activities. The target compounds were identified by GC-MS, IR, and ¹H NMR spectroscopies, and element analysis, and, in the case of 4k , its structure was established by single crystal X-ray diffraction. They showed not only fungicidal activities against Gibberella zeae, Cercospora beticola, Fusarium oxysporium, Rhizoctonia solani, and Botryosphaeria berengeriana, but also growth inhibition of Barnyard grass and Cole root and stalk.

Keywords:

• aza-Wittig reaction
• crystal structure
• fungicidal activities
• herbicidal activities
• Imidazolinone derivatives
• vinyliminophosphorane

Acknowledgments

The authors acknowledge financial support by the National Science Foundation of China (Grant No. 20102001), New Century Excellent Talents in Universities of Henan Province (Grant No. 2005HANCET-17), and the Scientific Research Fund of Zhejiang Provincial Education Department (Grant No. 20051292).