Triazol

Triazol (Htrz) je izomerno hemijsko jedinjenje sa molekulskom formulom C₂H₃N₃, koje sadrži petočlani prsten sa dva atoma ugljenika i tri atoma azota.

Dva izomera su:

Derivati

Triazolni antifungalni lekovi su flukonazol, izavukonazol, itrakonazol, vorikonazol, pramikonazol, ravukonazol, i posakonazol.

Triazolni fungicidi za biljnu zaštitu su epoksikonazol, triadimenol, propikonazol, metkonazol, ciprokonazol, tebukonazol, fluzilazol i paklobutrazol.

Benzotriazol se koristi u izradi fotografija.

Poljoprivredni značaj

Usled širenja otpornosti biljnih patogena na fungicide iz strobilurinske klase,^[1] kontrola gljiva kao što su Septoria tritici ili Gibberella zeae^[2] je u znatnoj meri zasnovana na primeni triazola.

Značaj u hemijkoj sintezi

Cikloadicija azidnih alkina je blaga i selektivna reakcija kojom se formiraju 1,2,3-triazoli. Reakcija nalazi široku primenu u bioortogonalnoj hemiji i u organskoj sintezi. Triazoli su relativno stabilne funkcionalne grupe, te triazolne veze imaju brojne primene (npr. kao zamena za fosfatnu osnovu DNK.^[3])

Srodna heterociklična jedinjenja

Imidazol, analog sa dva nesusedna atoma azota
Pirazol, analog sa dva susedna atoma azota
Tetrazol, analog sa četiri atoma azota

Reference

^ 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. Gisi, Ulrich; Sierotzki, Helge; Cook, Alison; McCaffery, Alan (2002). „Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides”. Pest Management Science. 58 (9): 859—867. PMID 12233175. doi:10.1002/ps.565. . [1]
^ Klix, Melanie B.; Verreet, Joseph-Alexander; Beyer, Marco (2007). „Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development”. Crop Protection. 26 (4): 683—690. doi:10.1016/j.cropro.2006.06.006.
^ 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.Isobe, Hiroyuki; Fujino, Tomoko; Yamazaki, Naomi; Guillot-Nieckowski, Marine; Nakamura, Eiichi (2008). „Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA”. Organic Letters. 10 (17): 3729—3732. PMID 18656947. doi:10.1021/ol801230k.

Spoljašnje veze

Synthesis of 1,2,3-triazoles (overview of recent methods)

[1] 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. Gisi, Ulrich; Sierotzki, Helge; Cook, Alison; McCaffery, Alan (2002). „Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides”. Pest Management Science. 58 (9): 859—867. PMID 12233175. doi:10.1002/ps.565. . [1]

[2] Klix, Melanie B.; Verreet, Joseph-Alexander; Beyer, Marco (2007). „Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development”. Crop Protection. 26 (4): 683—690. doi:10.1016/j.cropro.2006.06.006.

[3] 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.Isobe, Hiroyuki; Fujino, Tomoko; Yamazaki, Naomi; Guillot-Nieckowski, Marine; Nakamura, Eiichi (2008). „Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA”. Organic Letters. 10 (17): 3729—3732. PMID 18656947. doi:10.1021/ol801230k.

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