The condensations of thiourea, N-allylthiourea, N, N'-diallylthiourea and ethylenethiourea with 1, 4-dichlorobutyne in absolute ethanol gave 2-butyne-1, 4-bis (isothiuronium chloride), 2-butyne-1, 4-bis (N-allylisothiuronium chloride), 2-butyne-1, 4-bis (N, N'-diallylisothiuronium chloride), and 2-butyne-1, 4-bis (ethyleneisothiuronium chloride), respectively. Similar condensations could be effected using 1-chloro-2-butyne-4-ol to give 1-hydroxy-2-butyne-4-(isothiuronium chloride) and 1-hydroxy-2-butyne-4-(ethyleneisothiuronium chloride). These stable, crystalline products have been found to exert some inhibitory action on fungi, yeasts and mycobacterium. It was noteworthy to find that, unlike the common S-alkylisothioureas, some of the free bases of this series mentioned above could be readily isolated from their hydrochlorides by treatment with aqueous sodium carbonate.
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