134:
97:
164:
175:
853:
Rademacher, W.; Fritsch, H.; Graebe, J.E.; Sauter, H.; Jung, J. (1987). "Tetcyclacis and triazole-type plant growth retardants: Their influence on the biosynthesis of gibberellins and other metabolic processes".
130:: a azide and an alkyne react at high temperature to form a ring. However, the Huisgen strategy produces a mixture of isomers (typically 1,4- and 1,5-disubstituted) when used to produce substituted triazoles.
911:
Isobe, H.; Fujino, T.; Yamazaki, N.; Guillot-Nieckowski, M.; Nakamura, E. (2008). "Triazole-Linked
Analogue of Deoxyribonucleic Acid (DNA): Design, Synthesis, and Double-Strand Formation with Natural DNA".
402:
and in organic synthesis. Triazoles are relatively stable functional groups and triazole linkages can be used in a variety of applications, e.g. replacing the phosphate backbone of DNA.
229:
Triazoles are compounds with a vast spectrum of applications, varying from materials (polymers), agricultural chemicals, pharmaceuticals, photoactive chemicals and dyes.
133:
156:, which is relatively stable towards oxidation even at elevated temperatures and can produce triazoles with a broad range of substituents either in solvent or under
533:
Bolje, A.; Urankar, D.; Košmrlj, J. (2014). "Synthesis and NMR Analysis of 1,4-Disubstituted 1,2,3-Triazoles
Tethered to Pyridine, Pyrimidine, and Pyrazine Rings".
238:
Cyclohexylethyltriazol was briefly used as an alternative to
Cardiazol (Metrazol) in convulsive shock therapy treatment of mental illnesses during the 1940s.
57:
Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. However, triazoles are also useful in
1681:
965:
665:
582:
217:). Of those two, only the Einhorn-Brunner reaction is regioselective. Recent research has focused on grinding and microwave irradiation as
751:
Gisi, U.; Sierotzki, H.; Cook, A.; McCaffery, A. (2002). "Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides".
395:
127:
163:
174:
1725:
1448:
1015:
821:"Control of potato early blight with triazole fungicide using preventive and curative spraying, or a forecasting system"
65:. Lastly, the many free lone pairs in triazoles make them useful as coordination compounds, although not typically as
1698:
332:
Due to spreading resistance of plant pathogens towards fungicides of the strobilurin class, control of fungi such as
883:
1516:
1486:
958:
451:
446:
1381:
398:
is a mild and selective reaction that gives 1,2,3-triazoles as products. The reaction has been widely used in
214:
193:
Most techniques for producing 1,2,4-triazoles use the free energy of water, either by dehydrating a mixture of
148:, copper(I) salts select for the formation of 1,4-disubstituted 1,2,3-triazoles. One such catalyst is CuBr(PPh
1686:
1616:
519:
399:
58:
566:
1653:
1300:
515:
Development of homogeneous palladium catalytic systems for selected transformations of terminal acetylenes
375:
611:
31:
825:
344:
relies heavily on triazoles. Food, like store bought potatoes, contain retardants such as triazole or
951:
513:
1443:
1259:
793:
787:
Klix, M.B.; Verreet, J.-A.; Beyer, M. (2007). "Comparison of the declining triazole sensitivity of
202:
66:
856:
379:
1730:
1606:
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1571:
588:
535:
433:
345:
310:
287:
360:
1467:
930:
769:
733:
661:
578:
494:
35:
1611:
1561:
922:
864:
833:
801:
761:
753:
723:
691:
619:
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543:
484:
334:
1193:
1183:
429:
383:
340:
306:
247:
218:
145:
142:
1692:
1623:
1566:
1536:
1521:
1289:
1178:
715:
188:
171:
Conversely, ruthenium catalysts (RuAAC) select for 1,5-disubstituted 1,2,3-triazoles.
141:
In order to selectively prepare a desired isomer, metal catalysts are employed. In the
122:
1,2,3-Triazoles, also known as vicinal triazoles, are usually prepared following (3+2)
117:
86:
82:
1719:
1526:
1422:
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1155:
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352:
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77:
There are four triazole isomers, which are conventionally divided into two pairs of
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1056:
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982:
978:
791:
and increased sensitivity achieved by advances in triazole fungicide development".
318:
298:
275:
271:
263:
259:
61:, because the large number of nitrogen atoms causes triazoles to react similar to
805:
89:, an interstitial carbon separates out one nitrogen atom. Each category has two
34:
featuring a five-membered ring of two carbon atoms and three nitrogen atoms with
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90:
78:
20:
695:
54:, depending on the positioning of the nitrogen atoms within the ring.
1662:
1274:
926:
173:
162:
132:
95:
641:. Chemistry of Heterocyclic Compounds. Vol. 39. Wiley-Blackwell.
235:
is used in chemical photography as a restrainer and fog suppressant.
51:
765:
609:
1011:
657:
206:
194:
62:
884:"Growth Regulators for Containerized Herbaceous Perennial Plants"
126:
protocols. A common technique for unsubstituted triazoles is the
947:
93:
that differ by which nitrogen has a hydrogen bonded to it.
452:
Synthesis of 1,2,4-triazoles (overview of recent methods)
447:
Synthesis of 1,2,3-triazoles (overview of recent methods)
681:
Potts, K.T. (1961). "The
Chemistry of 1,2,4-Triazoles".
472:"Arylation of Click Triazoles with Diaryliodonium Salts"
137:
Thermal addition gives a mixture of 1,4 and 1,5 isomers
246:
Many triazoles have antifungal effects: the triazole
711:"Click Chemistry: 1,2,3-Triazoles as Pharmacophores"
1509:
1485:
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1442:
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1235:
1145:
1026:
1010:
999:
990:
709:Agalave, S.G.; Maujan, S.R.; Pore, V.S. (2011).
108:There are several methods to prepare triazoles.
85:, the three nitrogen atoms are adjacent; in the
414:, an analog with two nonadjacent nitrogen atoms
604:
602:
128:Huisgen azide-alkyne 1,3-dipolar cycloaddition
959:
8:
432:, substituted analogues that can be used as
420:, an analog with two adjacent nitrogen atoms
143:copper-catalysed azide-alkyne cycloaddition
1439:
1307:
1023:
1007:
996:
966:
952:
944:
837:
727:
488:
462:
569:Vol. 28. Netherlands: Springer.
7:
426:, an analog with four nitrogen atoms
396:azide alkyne Huisgen cycloaddition
14:
893:. Ball Publishing. pp. 14–60
470:Virant, M.; Košmrlj, J. (2019).
390:Importance in chemical synthesis
50:. Triazoles exhibit substantial
1449:thymidylate synthase inhibitors
839:10.4067/S0718-16202009000200013
654:Advances in Triazole Chemistry
1:
178:1,5 isomer from a Ru catalyst
167:1,4 isomer from a Cu catalyst
806:10.1016/j.cropro.2006.06.006
660:(Elsevier). pp. 21–27.
819:Mantecón, Jorge D. (2009).
280:plant-protection fungicides
1747:
882:Latimer, Joyce G. (2022).
186:
115:
18:
1676:
1517:bromochlorosalicylanilide
1487:Aminoacyl tRNA synthetase
575:10.1007/978-3-642-29429-7
242:Importance in agriculture
637:Temple, Carroll (2009).
215:Einhorn-Brunner reaction
19:Not to be confused with
561:Košmrlj, Janez (2012).
520:University of Ljubljana
490:10.1021/acs.joc.9b02197
400:bioorthogonal chemistry
376:plant growth retardants
59:bioorthogonal chemistry
1301:Squalene monooxygenase
1138:Systemic: ketoconazole
729:10.1002/asia.201100432
652:Farooq, Tahir (2021).
624:10.1002/anie.196305651
548:10.1002/ejoc.201403100
179:
168:
160:reaction conditions.
138:
100:
1726:Simple aromatic rings
1329:Systemic: terbinafine
869:10.1002/ps.2780210402
612:Angew. Chem. Int. Ed.
567:Top. Organomet. Chem.
512:Virant, Miha (2019).
177:
166:
136:
99:
32:heterocyclic compound
1617:Whitfield's ointment
1444:Pyrimidine analogues
1260:Polyene antimycotics
406:Related heterocycles
696:10.1021/cr60210a001
483:(21): 14030–14044.
203:Pellizzari reaction
1703:Never to phase III
1607:tribromometacresol
1577:sodium thiosulfate
1572:selenium disulfide
1468:Mitotic inhibitors
536:Eur. J. Org. Chem.
180:
169:
139:
101:
1713:
1712:
1505:
1504:
1431:
1430:
1382:β-glucan synthase
1376:
1375:
1355:
1354:
1254:
1253:
927:10.1021/ol801230k
921:(17): 3729–3732.
722:(10): 2696–2718.
667:978-0-12-817113-4
584:978-3-642-29428-0
542:(36): 8167–8181.
36:molecular formula
16:Chemical compound
1738:
1612:undecylenic acid
1562:potassium iodide
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1308:
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1008:
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841:
826:Cienc. Inv. Agr.
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777:
754:Pest Manag. Sci.
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742:
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492:
467:
430:Triazolium salts
369:
335:Septoria tritici
296:
248:antifungal drugs
211:alkyl hydrazines
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1741:
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1693:Clinical trials
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1303:
1295:
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1250:
1231:
1184:fosravuconazole
1141:
1017:
1016:lanosterol 14α-
1003:
992:
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972:
942:
910:
909:
905:
896:
894:
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789:Gibberella zeae
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639:1,2,4-Triazoles
636:
635:
631:
618:(10): 565–632.
608:
607:
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563:Click Triazoles
560:
559:
555:
532:
531:
527:
511:
510:
506:
469:
468:
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460:
443:
408:
392:
384:brassinosteroid
363:
341:Gibberella zeae
307:prothioconazole
290:
244:
227:
221:substitutes.
191:
185:
183:1,2,4-Triazoles
155:
151:
120:
114:
112:1,2,3-Triazoles
106:
87:1,2,4-triazoles
83:1,2,3-triazoles
75:
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1624:citronella oil
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1567:salicylic acid
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1559:
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1539:
1537:crystal violet
1534:
1529:
1524:
1522:chlorophetanol
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1290:amphotericin B
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1179:fosfluconazole
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963:
956:
948:
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903:
874:
863:(4): 241–252.
845:
832:(2): 291–296.
811:
800:(4): 683–690.
779:
766:10.1002/ps.565
760:(9): 859–867.
743:
716:Chem. Asian J.
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441:External links
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386:biosynthesis.
243:
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189:1,2,4-Triazole
187:Main article:
184:
181:
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118:1,2,3-Triazole
116:Main article:
113:
110:
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67:haptic ligands
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1423:ibrexafungerp
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1397:anidulafungin
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1204:oteseconazole
1202:
1200:
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1194:isavuconazole
1192:
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1187:
1185:
1182:
1180:
1177:
1175:
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1164:
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1157:
1156:efinaconazole
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1152:
1150:
1148:
1144:
1137:
1136:
1133:
1130:
1128:
1125:
1123:
1122:sertaconazole
1120:
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1100:
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1077:fenticonazole
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1073:
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1055:
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1050:
1048:
1047:chlormidazole
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690:(2): 87–127.
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353:paclobutrazol
351:In addition,
349:
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343:
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337:
336:
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328:
327:paclobutrazol
324:
320:
316:
315:cyproconazole
312:
308:
304:
303:propiconazole
300:
294:
289:
285:
284:epoxiconazole
281:
278:and triazole
277:
273:
269:
268:pramiconazole
265:
261:
257:
256:isavuconazole
253:
249:
241:
239:
236:
234:
233:Benzotriazole
230:
224:
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196:
190:
182:
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165:
161:
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131:
129:
125:
124:cycloaddition
119:
111:
109:
103:
98:
94:
92:
88:
84:
80:
72:
70:
68:
64:
60:
55:
53:
37:
33:
29:
22:
1649:tea tree oil
1634:lemon myrtle
1547:ethylparaben
1477:griseofulvin
1338:Benzylamines
1227:ravuconazole
1222:albaconazole
1214:voriconazole
1209:posaconazole
1199:itraconazole
1189:hexaconazole
1146:
1107:neticonazole
1097:luliconazole
1092:ketoconazole
1082:flutrimazole
1067:eberconazole
1057:clotrimazole
1042:butoconazole
918:
913:
906:
895:. Retrieved
890:
877:
860:
857:Pestic. Sci.
855:
848:
829:
824:
814:
797:
792:
788:
782:
757:
752:
746:
719:
714:
704:
687:
682:
676:
653:
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632:
615:
610:
562:
556:
539:
534:
528:
514:
507:
480:
475:
465:
393:
380:Brassinazole
374:are used as
350:
339:
333:
331:
319:tebuconazole
299:myclobutanil
276:posaconazole
272:ravuconazole
264:voriconazole
260:itraconazole
245:
237:
231:
228:
225:Applications
192:
170:
157:
140:
121:
107:
76:
56:
27:
25:
1689:from market
1668:pentamidine
1629:lemon grass
1587:taurolidine
1557:polynoxylin
1458:flucytosine
1402:caspofungin
1326:terbinafine
1312:Allylamines
1174:fluconazole
1166:terconazole
1161:fluconazole
1132:tioconazole
1127:sulconazole
1117:oxiconazole
1112:omoconazole
1087:isoconazole
1062:croconazole
1020:inhibitors)
1018:demethylase
975:Antifungals
891:GrowerTalks
372:triadimefon
364: [
357:uniconazole
346:tetcyclacis
323:flusilazole
311:metconazole
291: [
288:triadimenol
252:fluconazole
104:Preparation
1720:Categories
1658:atovaquone
1639:orange oil
1602:tolnaftate
1597:tolciclate
1582:sulbentine
1552:haloprogin
1532:ciclopirox
1497:tavaborole
1489:inhibitors
1475:Systemic:
1456:Systemic:
1417:rezafungin
1412:micafungin
1407:cilofungin
1391:Systemic:
1385:inhibitors
1368:amorolfine
1347:butenafine
1304:inhibitors
1288:Systemic:
1265:ergosterol
1172:Systemic:
1102:miconazole
1052:climbazole
1037:bifonazole
1028:Imidazoles
1004:inhibitors
1001:Ergosterol
915:Org. Lett.
897:2022-04-06
684:Chem. Rev.
458:References
436:precursors
361:flutriafol
199:hydrazides
81:. In the
1731:Triazoles
1699:Phase III
1687:Withdrawn
1644:patchouli
1592:ticlatone
1495:Topical:
1366:Topical:
1345:Topical:
1321:naftifine
1319:Topical:
1292:, hamycin
1280:natamycin
1273:Topical:
1246:abafungin
1244:Topical:
1237:Thiazoles
1220:Unknown:
1154:Topical:
1147:Triazoles
1072:econazole
1035:Topical:
658:The Devil
593:199490788
424:Tetrazole
412:Imidazole
382:inhibits
91:tautomers
79:tautomers
73:Isomerism
52:isomerism
1542:dimazole
1285:nystatin
1267:binding)
993:membrane
935:18656947
774:12233175
738:21954075
499:31553192
418:Pyrazole
282:include
250:include
28:triazole
21:Thiazole
1663:dapsone
1275:hamycin
518:(PhD).
219:greener
146:(CuAAC)
1682:WHO-EM
1510:Others
1360:Others
1012:Azoles
933:
772:
736:
664:
591:
581:
497:
370:, and
274:, and
207:imides
195:amides
63:azides
991:Wall/
887:(PDF)
589:S2CID
368:]
295:]
213:(the
205:) or
201:(the
30:is a
981:and
931:PMID
770:PMID
734:PMID
662:ISBN
579:ISBN
540:2014
495:PMID
394:The
329:.
325:and
209:and
197:and
158:neat
1654:PCP
983:J02
979:D01
923:doi
865:doi
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762:doi
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692:doi
620:doi
571:doi
544:doi
485:doi
434:NHC
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