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

Dusan Loos 1,* email, Eva Sidoova 1  and Viktor Sutoris 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

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MDPI and ACS Style

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.

AMA Style

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(4):81-93.

Chicago/Turabian Style

Loos, Dusan; Sidoova, Eva; Sutoris, Viktor. 1999. "Benzothiazole Derivatives. 48. Synthesis of 3-Alkoxycarbonylmethyl-6-bromo-2-benzothiazolones and 3-Alkoxycarbonylmethyl-6-nitro-2-benzothiazolones as Potential Plant Growth Regulators." Molecules 4, no. 4: 81-93.

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