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3-(2-Alkylsulfanyl-6-benzothiazolylaminomethyl)-2-benzoxazolethiones - Synthesis and Photosynthesis-Inhibiting Activity in Spinach Chloropasts
Molecules 1999, 4(4), 81-93; doi:10.3390/40400081
Article

Benzothiazole Derivatives. 48. Synthesis of 3-Alkoxycarbonylmethyl-6-bromo-2-benzothiazolones and 3-Alkoxycarbonylmethyl-6-nitro-2-benzothiazolones as Potential Plant Growth Regulators

1,* , 1 and 2
1 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina CH-2, SK- 842 15 Bratislava, Slovakia 2 Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska Dolina, SK - 842 15 Bratislava, Slovakia
* Author to whom correspondence should be addressed.
Received: 17 March 1998 / Accepted: 8 March 1999 / Published: 26 March 1999
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Abstract

3-Alkoxycarbonylmethyl-6-bromo- and 3-alkoxycarbonylmethyl-6-nitro-2-benzothiazolones were synthesized by reaction of alkylesters of halogenoacetic acids with 6-bromo-2-benzothiazolones and 6-nitro-2-benzothiazolones respectively. The compounds were tested for plant growth stimulating activity on wheat (Triticum aestivum). The bromo derivatives manifested 25.4 % average stimulating activity in comparison with the control. The stimulation activity of the nitro derivatives was not significant. Optimal structures of the compounds were obtained by a MMPI method, atomic charges and dipole moments were calculated by a semiempirical AM1 method. On the basis of molecular electrostatic potential it has been found that the biological activity of synthesized compounds depends on charge distribution in the molecules.
Keywords: 3-Alkoxycarbonylmethyl-6-bromo-2-benzothiazolones; 3-alkoxycarbonylmethyl- 6-nitro-2-benzothiazolones; plant growth regulators; AM1 calculations; lipophilicity 3-Alkoxycarbonylmethyl-6-bromo-2-benzothiazolones; 3-alkoxycarbonylmethyl- 6-nitro-2-benzothiazolones; plant growth regulators; AM1 calculations; lipophilicity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Loos, D.; Sidoova, E.; Sutoris, V. Benzothiazole Derivatives. 48. Synthesis of 3-Alkoxycarbonylmethyl-6-bromo-2-benzothiazolones and 3-Alkoxycarbonylmethyl-6-nitro-2-benzothiazolones as Potential Plant Growth Regulators. Molecules 1999, 4, 81-93.

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