Preparation and fungicidal activity of 5-substituted hydantoins and their 2-thio analogs

Abstract

5-(Arylmethylene)hydantoins (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) and 5-(arylmethylene)-2-thiohydantoins (20-37) have been synthesized by condensation of aromatic aldehydes with hydantoin (1) or 2-thiohydantoin (2) in the presence of ethanolamine. A number of 5-alkyl-and 5-(arylmethyl)hydantoins (40-48) and their 2-thio analogs (50-55) were synthesized from amino acids. All of these compounds were tested for pesticidal activity.

Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

“…Their 2-thioxo analogs, 2-thiohydantoins (2-thioxo-imidazolizin-4-one) also display significant biological activities and are employed as established drugs, fungicides or herbicides [5,6] . Both compounds are considered as useful intermediates in peptide synthesis and structure determination of polypeptides [7] .…”

Crystal Structure of 5-Phenyl-2-thioxo-4-imidazolidinone

“…1,2 These compounds are considered as useful intermediates in peptide synthesis and the structure determination of polypeptides. 3 Since the biological activities and physicochemical properties of the compounds are closely related to the electronic structure, conformation and intermolecular interactions, experimental data pertaining to these features are therefore very important.…”

Use of 2-(1-(4-Bromophenyl) Ethylidene)hydrazinecarbothioamide and 2-(5-Chloro-2-Oxoindolin-3-Ylidene)hydrazinecarbothioamide in the Syntheses of 2-Thiohydantoin, Pyrimidine Derivatives: Evaluation of Their Antimicrobial Activities.

“…Thiohydantoins are known for their uses as hypolipidemic [13] and antimutagenic [14]. In addition, thiohydantoin compounds are used as herbicides [15] and fungicides agents [16]. Recently, there has been interest in the search of new synthetic routes for the preparation of these type of compounds, via solution or solid state reactions [17][18][19].…”