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Molecules 2007, 12(12), 2589-2598; doi:10.3390/12122589
Article

Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors

1,* , 2
,
1
,
3
 and
4
1 Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, Hradec Králové, 500 05, Czech Republic 2 Department of Pharmacognosy, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, Hradec Králové, 500 05, Czech Republic 3 Department of Biology, Faculty of Education, University of Hradec Kralove, Víta Nejedlého 573 Hradec Králové, 500 03, Czech Republic 4 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská Dolina CH-2, 842 15 Bratislava, Slovak Republic
* Author to whom correspondence should be addressed.
Received: 27 November 2007 / Revised: 14 December 2007 / Accepted: 14 December 2007 / Published: 20 December 2007
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Abstract

The condensation of substituted pyrazine-2-carboxylic acid chlorides with ring-substituted anilines yielded five substituted pyrazine-2-carboxylic acid amides. Thesynthesis, and analytical, lipophilicity and biological data of the newly synthesizedcompounds are presented in this paper. The photosynthesis inhibition, antialgal activityand the effect of a series of pyrazine derivatives as abiotic elicitors on the accumulation offlavonoids in a callus culture of Ononis arvensis (L.) were investigated. The most activeinhibitor of the oxygen evolution rate in spinach chloroplasts was 6-chloro-pyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2, IC50 = 51.0 μmol·L-1). The highestreduction of chlorophyll content in Chlorella vulgaris was found for 5-tert-butyl-N-(4-chloro-3-methylphenyl)-pyrazine-2-carboxamide (3, IC50 = 44.0 μmol·L-1). The maximalflavonoid production (about 900%) was reached after a twelve-hour elicitation processwith 6-chloropyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2).
Keywords: synthesis of pyrazinecarboxamides; photosynthesis inhibiting and antialgal activity; rest-harrow; flavonoid production; culture in vitro; lipophilicity. synthesis of pyrazinecarboxamides; photosynthesis inhibiting and antialgal activity; rest-harrow; flavonoid production; culture in vitro; lipophilicity.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Doležal, M.; Tůmová, L.; Kešetovičová, D.; Tůma, J.; Kráľová, K. Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors. Molecules 2007, 12, 2589-2598.

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