Substituted N-phenylpyrazine-2-carboxamides, their synthesis and evaluation as herbicides and abiotic elicitors

Molecules. 2007 Dec 20;12(12):2589-98. doi: 10.3390/12122589.

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, IC(50) = 51.0 micromol.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, IC(50) = 44.0 micromol.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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / chemistry
  • Acetamides / pharmacology*
  • Chlorella vulgaris / drug effects
  • Chlorophyll / metabolism
  • Chloroplasts / drug effects
  • Flavonoids / metabolism
  • Herbicides / chemical synthesis*
  • Herbicides / chemistry
  • Herbicides / pharmacology*
  • Oxygen

Substances

  • Acetamides
  • Flavonoids
  • Herbicides
  • Chlorophyll
  • acetamide
  • Oxygen