145:
108:
175:
186:
864:
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".
141:: 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.
922:
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".
413:
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.
240:
Triazoles are compounds with a vast spectrum of applications, varying from materials (polymers), agricultural chemicals, pharmaceuticals, photoactive chemicals and dyes.
144:
167:, 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
544:
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".
249:
Cyclohexylethyltriazol was briefly used as an alternative to
Cardiazol (Metrazol) in convulsive shock therapy treatment of mental illnesses during the 1940s.
68:
Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. However, triazoles are also useful in
1692:
976:
676:
593:
228:). Of those two, only the Einhorn-Brunner reaction is regioselective. Recent research has focused on grinding and microwave irradiation as
762:
Gisi, U.; Sierotzki, H.; Cook, A.; McCaffery, A. (2002). "Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides".
406:
138:
174:
185:
1736:
1459:
1026:
832:"Control of potato early blight with triazole fungicide using preventive and curative spraying, or a forecasting system"
76:. Lastly, the many free lone pairs in triazoles make them useful as coordination compounds, although not typically as
1709:
343:
Due to spreading resistance of plant pathogens towards fungicides of the strobilurin class, control of fungi such as
894:
1527:
1497:
969:
462:
457:
1392:
409:
is a mild and selective reaction that gives 1,2,3-triazoles as products. The reaction has been widely used in
225:
204:
Most techniques for producing 1,2,4-triazoles use the free energy of water, either by dehydrating a mixture of
159:, copper(I) salts select for the formation of 1,4-disubstituted 1,2,3-triazoles. One such catalyst is CuBr(PPh
1697:
1627:
530:
410:
69:
577:
1664:
1311:
526:
Development of homogeneous palladium catalytic systems for selected transformations of terminal acetylenes
386:
622:
42:
836:
355:
relies heavily on triazoles. Food, like store bought potatoes, contain retardants such as triazole or
962:
524:
1454:
1270:
804:
798:
Klix, M.B.; Verreet, J.-A.; Beyer, M. (2007). "Comparison of the declining triazole sensitivity of
213:
77:
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1741:
1617:
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356:
321:
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505:
46:
1622:
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933:
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844:
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772:
764:
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702:
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345:
1204:
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317:
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156:
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1703:
1634:
1577:
1547:
1532:
1300:
1189:
726:
199:
182:
Conversely, ruthenium catalysts (RuAAC) select for 1,5-disubstituted 1,2,3-triazoles.
152:
In order to selectively prepare a desired isomer, metal catalysts are employed. In the
133:
1,2,3-Triazoles, also known as vicinal triazoles, are usually prepared following (3+2)
128:
97:
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There are four triazole isomers, which are conventionally divided into two pairs of
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1219:
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1052:
993:
989:
802:
and increased sensitivity achieved by advances in triazole fungicide development".
329:
309:
286:
282:
274:
270:
72:, because the large number of nitrogen atoms causes triazoles to react similar to
816:
100:, an interstitial carbon separates out one nitrogen atom. Each category has two
45:
featuring a five-membered ring of two carbon atoms and three nitrogen atoms with
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65:, depending on the positioning of the nitrogen atoms within the ring.
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184:
173:
143:
106:
652:. Chemistry of Heterocyclic Compounds. Vol. 39. Wiley-Blackwell.
246:
is used in chemical photography as a restrainer and fog suppressant.
62:
776:
620:
1022:
668:
217:
205:
73:
895:"Growth Regulators for Containerized Herbaceous Perennial Plants"
137:
protocols. A common technique for unsubstituted triazoles is the
958:
104:
that differ by which nitrogen has a hydrogen bonded to it.
463:
Synthesis of 1,2,4-triazoles (overview of recent methods)
458:
Synthesis of 1,2,3-triazoles (overview of recent methods)
692:
Potts, K.T. (1961). "The
Chemistry of 1,2,4-Triazoles".
483:"Arylation of Click Triazoles with Diaryliodonium Salts"
148:
Thermal addition gives a mixture of 1,4 and 1,5 isomers
257:
Many triazoles have antifungal effects: the triazole
722:"Click Chemistry: 1,2,3-Triazoles as Pharmacophores"
1520:
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1156:
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1021:
1010:
1001:
720:Agalave, S.G.; Maujan, S.R.; Pore, V.S. (2011).
119:There are several methods to prepare triazoles.
96:, the three nitrogen atoms are adjacent; in the
425:, an analog with two nonadjacent nitrogen atoms
615:
613:
139:Huisgen azide-alkyne 1,3-dipolar cycloaddition
970:
8:
443:, substituted analogues that can be used as
431:, an analog with two adjacent nitrogen atoms
154:copper-catalysed azide-alkyne cycloaddition
1450:
1318:
1034:
1018:
1007:
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963:
955:
848:
738:
499:
473:
580:Vol. 28. Netherlands: Springer.
7:
437:, an analog with four nitrogen atoms
407:azide alkyne Huisgen cycloaddition
25:
904:. Ball Publishing. pp. 14–60
481:Virant, M.; Košmrlj, J. (2019).
401:Importance in chemical synthesis
61:. Triazoles exhibit substantial
1460:thymidylate synthase inhibitors
850:10.4067/S0718-16202009000200013
665:Advances in Triazole Chemistry
1:
189:1,5 isomer from a Ru catalyst
178:1,4 isomer from a Cu catalyst
817:10.1016/j.cropro.2006.06.006
671:(Elsevier). pp. 21–27.
830:Mantecón, Jorge D. (2009).
291:plant-protection fungicides
1758:
893:Latimer, Joyce G. (2022).
197:
126:
29:
1687:
1528:bromochlorosalicylanilide
1498:Aminoacyl tRNA synthetase
586:10.1007/978-3-642-29429-7
253:Importance in agriculture
648:Temple, Carroll (2009).
226:Einhorn-Brunner reaction
30:Not to be confused with
572:Košmrlj, Janez (2012).
531:University of Ljubljana
501:10.1021/acs.joc.9b02197
411:bioorthogonal chemistry
387:plant growth retardants
70:bioorthogonal chemistry
1312:Squalene monooxygenase
1149:Systemic: ketoconazole
740:10.1002/asia.201100432
663:Farooq, Tahir (2021).
635:10.1002/anie.196305651
559:10.1002/ejoc.201403100
190:
179:
171:reaction conditions.
149:
111:
1737:Simple aromatic rings
1340:Systemic: terbinafine
880:10.1002/ps.2780210402
623:Angew. Chem. Int. Ed.
578:Top. Organomet. Chem.
523:Virant, Miha (2019).
188:
177:
147:
110:
43:heterocyclic compound
1628:Whitfield's ointment
1455:Pyrimidine analogues
1271:Polyene antimycotics
417:Related heterocycles
707:10.1021/cr60210a001
494:(21): 14030–14044.
214:Pellizzari reaction
1714:Never to phase III
1618:tribromometacresol
1588:sodium thiosulfate
1583:selenium disulfide
1479:Mitotic inhibitors
547:Eur. J. Org. Chem.
191:
180:
150:
112:
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1723:
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1442:
1441:
1393:β-glucan synthase
1387:
1386:
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1365:
1265:
1264:
938:10.1021/ol801230k
932:(17): 3729–3732.
733:(10): 2696–2718.
678:978-0-12-817113-4
595:978-3-642-29428-0
553:(36): 8167–8181.
47:molecular formula
27:Chemical compound
16:(Redirected from
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1623:undecylenic acid
1573:potassium iodide
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441:Triazolium salts
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346:Septoria tritici
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259:antifungal drugs
222:alkyl hydrazines
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1704:Clinical trials
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1027:lanosterol 14α-
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650:1,2,4-Triazoles
647:
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642:
629:(10): 565–632.
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574:Click Triazoles
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395:brassinosteroid
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352:Gibberella zeae
318:prothioconazole
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232:substitutes.
202:
196:
194:1,2,4-Triazoles
166:
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123:1,2,3-Triazoles
117:
98:1,2,4-triazoles
94:1,2,3-triazoles
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874:(4): 241–252.
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843:(2): 291–296.
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811:(4): 683–690.
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777:10.1002/ps.565
771:(9): 859–867.
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727:Chem. Asian J.
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452:External links
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397:biosynthesis.
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200:1,2,4-Triazole
198:Main article:
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129:1,2,3-Triazole
127:Main article:
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1215:oteseconazole
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1205:isavuconazole
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1167:efinaconazole
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1133:sertaconazole
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1088:fenticonazole
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1058:chlormidazole
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364:paclobutrazol
362:In addition,
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338:paclobutrazol
335:
331:
327:
326:cyproconazole
323:
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315:
314:propiconazole
311:
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300:
296:
295:epoxiconazole
292:
289:and triazole
288:
284:
280:
279:pramiconazole
276:
272:
268:
267:isavuconazole
264:
260:
252:
250:
247:
245:
244:Benzotriazole
241:
235:
233:
231:
227:
223:
219:
215:
211:
207:
201:
193:
187:
183:
176:
172:
170:
158:
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146:
142:
140:
136:
135:cycloaddition
130:
122:
120:
114:
109:
105:
103:
99:
95:
91:
83:
81:
79:
75:
71:
66:
64:
48:
44:
40:
33:
19:
1660:tea tree oil
1645:lemon myrtle
1558:ethylparaben
1488:griseofulvin
1349:Benzylamines
1238:ravuconazole
1233:albaconazole
1225:voriconazole
1220:posaconazole
1210:itraconazole
1200:hexaconazole
1157:
1118:neticonazole
1108:luliconazole
1103:ketoconazole
1093:flutrimazole
1078:eberconazole
1068:clotrimazole
1053:butoconazole
929:
924:
917:
906:. Retrieved
901:
888:
871:
868:Pestic. Sci.
866:
859:
840:
835:
825:
808:
803:
799:
793:
768:
763:
757:
730:
725:
715:
698:
693:
687:
664:
658:
649:
643:
626:
621:
573:
567:
550:
545:
539:
525:
518:
491:
486:
476:
404:
391:Brassinazole
385:are used as
361:
350:
344:
342:
330:tebuconazole
310:myclobutanil
287:posaconazole
283:ravuconazole
275:voriconazole
271:itraconazole
256:
248:
242:
239:
236:Applications
203:
181:
168:
151:
132:
118:
87:
67:
38:
36:
1700:from market
1679:pentamidine
1640:lemon grass
1598:taurolidine
1568:polynoxylin
1469:flucytosine
1413:caspofungin
1337:terbinafine
1323:Allylamines
1185:fluconazole
1177:terconazole
1172:fluconazole
1143:tioconazole
1138:sulconazole
1128:oxiconazole
1123:omoconazole
1098:isoconazole
1073:croconazole
1031:inhibitors)
1029:demethylase
986:Antifungals
902:GrowerTalks
383:triadimefon
375: [
368:uniconazole
357:tetcyclacis
334:flusilazole
322:metconazole
302: [
299:triadimenol
263:fluconazole
115:Preparation
1731:Categories
1669:atovaquone
1650:orange oil
1613:tolnaftate
1608:tolciclate
1593:sulbentine
1563:haloprogin
1543:ciclopirox
1508:tavaborole
1500:inhibitors
1486:Systemic:
1467:Systemic:
1428:rezafungin
1423:micafungin
1418:cilofungin
1402:Systemic:
1396:inhibitors
1379:amorolfine
1358:butenafine
1315:inhibitors
1299:Systemic:
1276:ergosterol
1183:Systemic:
1113:miconazole
1063:climbazole
1048:bifonazole
1039:Imidazoles
1015:inhibitors
1012:Ergosterol
926:Org. Lett.
908:2022-04-06
695:Chem. Rev.
469:References
447:precursors
372:flutriafol
210:hydrazides
92:. In the
1742:Triazoles
1710:Phase III
1698:Withdrawn
1655:patchouli
1603:ticlatone
1506:Topical:
1377:Topical:
1356:Topical:
1332:naftifine
1330:Topical:
1303:, hamycin
1291:natamycin
1284:Topical:
1257:abafungin
1255:Topical:
1248:Thiazoles
1231:Unknown:
1165:Topical:
1158:Triazoles
1083:econazole
1046:Topical:
669:The Devil
604:199490788
435:Tetrazole
423:Imidazole
393:inhibits
102:tautomers
90:tautomers
84:Isomerism
63:isomerism
18:Triazoles
1553:dimazole
1296:nystatin
1278:binding)
1004:membrane
946:18656947
785:12233175
749:21954075
510:31553192
429:Pyrazole
293:include
261:include
39:triazole
32:Thiazole
1674:dapsone
1286:hamycin
529:(PhD).
230:greener
157:(CuAAC)
1693:WHO-EM
1521:Others
1371:Others
1023:Azoles
944:
783:
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675:
602:
592:
508:
381:, and
285:, and
218:imides
206:amides
74:azides
1002:Wall/
898:(PDF)
600:S2CID
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224:(the
216:) or
212:(the
41:is a
992:and
942:PMID
781:PMID
745:PMID
673:ISBN
590:ISBN
551:2014
506:PMID
405:The
340:.
336:and
220:and
208:and
169:neat
1665:PCP
994:J02
990:D01
934:doi
876:doi
845:doi
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735:doi
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555:doi
496:doi
445:NHC
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