SYNTHESIS AND BIOLOGICAL ACTIVITIES OF NEW CHIRAL IMIDAZOLINONE DERIVATIVES

摘要

New optically active 2-thio-4-imidazolinones 3 with a chiral carbon at position-3 were synthesized from isothiocyanates 2, which were obtained from aza-Wittig reactions of vinyliminophosphoranes 1 with CS2, with easily accessible chiral (S)- or (R)-amino acid methyl ester hydrochlorides. 2-Methylthio-4H-imidazolin-4-ones 4 were obtained by the S-alkylation of compounds 3 in the presence of K2CO3 causing partial racemization of the enantiomeric pure products. These compoundswere identified by MS, IR, 1HNMR, 13CNMRspectroscopy, and elemental analysis. The structures of enantiomers 3c and 3d were also confirmed by X-ray diffraction analysis. The results of preliminary bioassay indicated that compounds 4 exhibited growth inhibition of barnyard grass and cole root and stalk, and fungicidal activities against Fusarium oxysporium, Rhizoctonia solani, Gibberella zeae, Dothiorella gregaria, and Colletotrichum gossypii. Supplemental materials are available for this article. Go to the publisher’s online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.