Solution-Phase Parallel Syntheses of Herbicidal 1-Phenyl-2,4,5- Imidazolidinetriones and 2-Thioxo-4,5-Imidazolidinediones

Title:Solution-Phase Parallel Syntheses of Herbicidal 1-Phenyl-2,4,5- Imidazolidinetriones and 2-Thioxo-4,5-Imidazolidinediones

Volume: 16 Issue: 1

Author(s): Bin Li, Ying Man, Li-Ping Bai, Hai-Ying Ji and Xue-Geng Shi

Affiliation:

Keywords: Carbodiimide, herbicide, imidazolidinetrione, protoporphyrinogen oxidase, solution-phase parallel synthesis, 2- thioxo-4, 5-imidazolidinedione, 1-Phenyl-2, 4, 5-Imidazolidinetriones, Abutilon theophrasti, Oxalyl chloride.

Abstract: In order to find new herbicidally active compounds, a fifteen-member library, focusing on the variation of 3- position substituents of 2,4,5-imidazolidine-trione or 2-thioxo-4,5-imidazolidinedione, was designed and prepared in parallel by the reaction of various ureas or thioureas with oxalyl chloride using solution-phase technology. An interesting and, to the best of our knowledge, unprecedented finding is that a by-product of 1-phenyl-3-propylcarbodiimide was formed during the addition of oxalyl chloride into the solution of 1-phenyl-3-propylthiourea in the presence of triethylamine in dichloromethane. It has been shown that the herbicidal activity of 2,4,5-imidazolidinetriones is about the same as that of their analogous 2-thioxo-4,5-imidazolidinediones. Compound with propyl or isopropyl group at the 3- position of 2,4,5-imidazolidinetrione ring demonstrated good herbicidal activity. The most active compound, 1-(2-fluoro- 4-chloro-5-propargyloxy)-phenyl-3-propyl-2-thioxo-4,5-imidazolidinedione, gave 95% control of the growth of velvetleaf at 200 g/ha in the post-emergence test.

Cite this article as:

Li Bin, Man Ying, Bai Li-Ping, Ji Hai-Ying and Shi Xue-Geng, Solution-Phase Parallel Syntheses of Herbicidal 1-Phenyl-2,4,5- Imidazolidinetriones and 2-Thioxo-4,5-Imidazolidinediones, Combinatorial Chemistry & High Throughput Screening 2013; 16 (1) . https://dx.doi.org/10.2174/1386207311316010010