Abstract
Cartap hydrochloride, 1, 3-bis (carbamoylthio)-2-N, N-dimethylaminopropane hydrochloride (I), an insecticide, hydrolyzes to 1, 3-dimercapto-2-N, N-dimethylaminopropane (II) which are oxidized to nereistoxin, 4-N, N-dimethylamino-1, 2-dithiolane (III). The hydrolysis was a base-catalyzed pseudo-first-order reaction, of which the rate constants were measured by a pH stat method and polarography in pH 4-12 at 0°and 25°. For example, the half-life (t1/2) at pH 7 was 10 min at 25°. III was so stable that no degradation was observed after 24 hr at 100°in pH 1-4 and that t1/2 at pH 7 was to be 2.4 years at 25°. However the disulfide (III) hydrolyzes to 2-N, N-dimethylamino-3-mercaptopropanesulfenic acid (IV) at pOH 1.1 with t1/2 2.2 hr at 100°. The isomer of I, 2, 3-bis (carbamoylthio)-N, N-dimethylpropylamine hydrochloride (VII), hydrolyzes 10 times as rapid as I.
