Triazole
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Triazole (Htrz) refers to either one of a pair of isomeric chemical compounds with molecular formula C2H3N3, having a five-membered ring of two carbon atoms and three nitrogen atoms.
The two isomers are:
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[edit] Derivatives
The triazole antifungal drugs include fluconazole, isavuconazole, itraconazole, voriconazole, pramiconazole, and posaconazole.
The triazole plant protection fungicides include epoxiconazole, triadimenol, propiconazole, metconazole, cyproconazole, tebuconazole, flusilazole and paclobutrazol.
[edit] Importance in agriculture
Due to spreading resistance of plant pathogens towards fungicides of the strobilurin class,[1] control of fungi such as Septoria tritici or Gibberella zeae[2] relies heavily on triazoles.
[edit] Importance in chemical synthesis
The azide alkyne Huisgen cycloaddition is a mild and selective reaction that gives 1,2,3-triazoles as products. The reaction has been widely used in bioorthogonal chemistry and in organic synthesis. Triazoles are relatively stable functional groups and triazole linkages can be used in a variety of applications (for example, replacing the phosphate backbone of DNA.[3])
[edit] Related heterocycles
- Imidazole, an analog with two nonadjacent nitrogen atoms
- Pyrazole, an analog with two adjacent nitrogen atoms
- Tetrazole, an analog with four nitrogen atoms
[edit] External links
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[edit] References
- ^ Gisi U, Sierotzki H,Cook A, McCaffery A (2002): Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides. Pest Management Science 58: 859–867. [1]
- ^ Klix MB, Verreet J-A, Beyer M (2007): Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development. Crop Protection 26:683-690. [2]
- ^ Hiroyuki Isobe et al. (2008) Triazole-Linked Analogue of Deoxyribonucleic Acid (TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA, Org. Lett. 10 (17), pp 3729–3732.[3]
