Facile Synthesis of 5-Arylidene Thiohydantoin by Sequential Sulfonylation/Desulfination Reaction

Abstract

The sequential sulfonylation/desulfination reactions of 5-benzylthiohydantoin with excess arylsulfonyl chlorides in the presence of triethylamine have been developed to afford a wide range of 5-arylidene thiohydantoin derivatives in moderate to excellent yields. A plausible sulfonylation/desulfination mechanism was proposed. The bioassay showed that these compounds exhibit certain fungicidal activities with the 71.9% inhibition rate of 2K against B. cinerea, and 57.6% inhibition rate of 2m against A. solani, respectively.

Discovery of 5-(5,5-Dimethylbutenolide-3-ethylidene)-2-amino-imidazolinone Derivatives as Fungicidal Agents

“…cinerea and F . graminearum were evaluated using methods in the references [21,22,23] by the mycelium growth rate and spore germination tests [24,25]. The cultures were incubated at 25 ± 0.5 °C.…”

Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues

“…The preliminary fungicidal activities of compounds 5 – 6 against F. graminearum , R. solani , A. solani , S. sclerotiorum , and B. cinerea were evaluated using methods in the references [33,34,35,36,37] by the mycelium growth rate [38]. The culture was incubated at 25 ± 0.5 °C.…”

Synthesis and Activity of Novel Acylthiourea with Hydantoin

“…The preliminary fungicidal activities of compounds 7 – 9 against F. oxysporurm , A. solani , B. berengeriana , C. arachidcola and F. graminearum were evaluated using methods in the references [7,10] by the mycelium growth rate test [38]. The culture was incubated at 25 ± 0.5 ºC.…”

“…In addition, these derivatives are very useful building blocks for the synthesis of various heterocycles such as 5-arylidene derivatives of imidazoline-4-one, imidazothiazine, diazinone, and diazepinone [ 7 – 9 ]. In our laboratory, several types of hydantoin and thiohydantioin derivatives ( 1 , 2 , 3 ) were synthesized, and we showed that some of them exhibit good herbicidal, fungicidal and insecticidal activities [ 10 – 13 ]. Acylthioureas are the key structural motifs of numerous compounds that displayed a wide range of biological activity such as antimicrobial, antipathogenic, insecticidal, fungicidal, antitumor activities and influenza virus inhibitors [ 14 – 21 ].…”

“…We could not find acylthiourea derivatives containing hydantoin and thiohydantion heterocycles in references. Continuing effort of our ongoing project aimed at looking for novel biologically active hydantoin and thiohydantion heterocyclic compounds [ 10 – 13 ], herein, we report a new type of acylthiourea derivatives containing hydantoin and thiohydantion heterocycles ( Scheme 1 ) and their biological activities.…”