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Benzothiazole compounds 23. Synthesis, structure, and growth-regulating activity of 2-alkoxycarbonylmethylthio-3-alkylbenzothiazolium salts

V. Sutoris, A. Gáplovský, R. Sohlerová, and V. Sekerka

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, CS-842 15 Bratislava


Abstract: 2-Alkoxycarbonylmethylthio-3-alkylbenzothiazolium salts have been pre- pared by treatment of 3-alkyl-2-benzothiazolinethiones with esters of bromoacetic acid and their structures were proved by evaluation of  1H NMR spectra. It was found that besides 2-alkoxycarbonylmethylthio-3-alkyIben- zothiazolium salts as the main product also 2-alkoxycarbonylmethylthio- benzothiazole, 2-alkylthiobenzothiazole, and 2-alkylthio-3-alkoxycarbo- nylmethylbenzothiazolium bromide were formed, indicating the formation of sulfonium salts as intermediates. The course of the reaction was studied by IR spectroscopy, isotachophoresis as well as by liquid and gas chromatography. 2-Methoxycarbonylmethylthio-3-methylbenzothiazolium bromide was found to show high growth-stimulating activity (ast = +7.5 x 10-11 mol dm-3.

Full paper in Portable Document Format: 394a491.pdf


Chemical Papers 39 (4) 491–501 (1985)

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