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1,2,4-Triazole

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  • 1,2,4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms.
  • 1,2,4-Triazole is a basic aromatic heterocycle. 1,2,4-Triazole derivatives find use in a wide variety of applications, most notably as antifungals such as fluconazole and itraconazole.
  • 1,2,4-Triazoles can be prepared using the Einhorn-Brunner reaction or the Pellizzari reaction.
  • 1,2,4-Triazole, triazole alanine, triazole acetic acid, triazole pyruvic acid and triazole lactic acid are the common metabolites derived from triazole-containing fungicides that act by inhibiting sterol synthesis.
  • 1,2,4-Triazole, triazole alanine and triazole acetic acid are the commonly used names for IUPAC nomenclatures 1H-1,2,4-triazole, 1,2,4-triazolyl-3-alanine, and 1H-1,2,4-triazol-l-ylacetic acid ,respectively.
  • These three metabolites commonly occur as plant or soil metabolites and are collectively known as the “triazole derivative metabolites”.
  • Triazole alanine and triazole acetic acid residues are primarily associated with plant commodities, while 1,2,4-triazole is mainly associated with animal commodities, lesser amounts of this compound being found in plant commodities.
  • The toxicological database for 1,2,4-triazole was sufficient for the evaluation of this compound, while the toxicological databases for triazole alanine and triazole acetic acid were more limited.
  • The inhibition of Salmonella typhimurium by 1,2,4-triazole appears to be mediated through an effect on L-cysteine biosynthesis.
  • 0-Acetylserine sulfhydrylase A, the final enzyme in the L-cysteine biosynthetic pathway, was found to catalyze a reaction between 0-acetyl-L-serine and 1,2,4triazole, giving 1,2,4-triazole-1-alanine as a product.
  • In wild type S. typhimurium grown on 4 mM I,2,4-triazole, 97% of the total 0-acetyl-L-serine synthesized in uivo is incorporated into 1,2,4-triazole-lalanine.
  • 1,2,4-Triazole also significantly lowers the levels of several of the enzymes necessary for sulfate reduction.
  • In vitro studies, using purified preparations of 0-acetylserine sulfhydrylase A, revealed greater losses of triazolylase activity than sulfhydrylase activity in the enzymes from both cysK mutants.
  • Resistance to 1,2,4-triazole apparently can arise from mutations leading to a preferential loss of triazolylase activity or from mutations which diminish both activities to the extent that high concentrations of 0-acetyl-L-serine and sulfide accumulate behind the sulfhydrylase reaction.

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