title: Solution-phase parallel syntheses of herbicidal 1-phenyl-2,4,5- imidazolidinetriones and 2-thioxo-4,5-imidazolidinediones.
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.
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd., Shenyang, China. libin1@sinochem.com
authors.forename: Bin
authors.initials: B
authors.lastname: Li
authors.forename: Ying
authors.initials: Y
authors.lastname: Man
authors.forename: Li-Ping
authors.initials: LP
authors.lastname: Bai
authors.forename: Hai-Ying
authors.initials: HY
authors.lastname: Ji
authors.forename: Xue-Geng
authors.initials: XG
authors.lastname: Shi
authors.forename: Dong-Liang
authors.initials: DL
authors.lastname: Cui
mesh_terms: D002712:Chlorides / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D010070:Oxalates / Q000138:chemical synthesis / Q000737:chemistry; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D002712:Chlorides; D006540:Herbicides; D048289:Imidazolidines; D010070:Oxalates; D013890:Thiourea; C092266:oxalyl chloride