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Benzothiazole Compounds. 44. Preparation and Growth Regulation Properties of 3-Substituted 2-Benzothiazolinones and Their 4-Chloro Derivatives

V. Sutoris, A. Gáplovský, V. Sekerka, and P. Ertl

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

 

Abstract: The reactions of (2-oxobenzothiazolin-3-yl)acetyl chloride and (4-chloro-2-oxobenzothiazolin-3-yl)acetyl chloride with phenol, methylphenols, dimethylphenols, and methoxyphenols in acetone in the presence of pyridine gave the corresponding 3-phenoxycarbonylmethyl-2-benzothiazolinones and their 4-chloro derivatives. The mentioned compounds have exhibited a growth stimulation effect of 6 to 60 %, at the concentration of 10-5 mol dm-3 upon the coleoptile of Triticum aestivum L. The UV and IR spectra of the synthesized compounds are presented. The structures and geometry of the basic compounds have been simulated by means of the quantum chemistry semiempirical method AM1. The calculations have proved the existence of two approximately equally stable conformers differing in the dihedral angles of the phenylcarbonyl group. The differences found in the geometry of molecules may be used for explanation of the different spectroscopic behaviour.

Full paper in Portable Document Format: 474a251.pdf

 

Chemical Papers 47 (4) 251–255 (1993)

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