Triazole refers to either one of a pair of
isomerIn chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
ic
chemical compoundA chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
s with molecular formula C
2H
3N
3, having a five-membered ring of two carbon atoms and three nitrogen atoms.
The two isomers are:
- 1,2,3-Triazole
1,2,3-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
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...
Derivatives
The triazole
antifungal drugAn antifungal medication is a medication used to treat fungal infections such as athlete's foot, ringworm, candidiasis , serious systemic infections such as cryptococcal meningitis, and others...
s include
fluconazoleFluconazole is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections. In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol. It is commonly marketed under the trade...
,
isavuconazoleIsavuconazole is a triazole antifungal. Its prodrug, Isavuconazonium sulfate is currently in Phase III clinical trials....
,
itraconazoleItraconazole , invented in 1984, is a triazole antifungal agent that is prescribed to patients with fungal infections. The drug may be given orally or intravenously.-Medical uses:...
,
voriconazoleVoriconazole is a triazole antifungal medication that is generally used to treat serious, invasive fungal infections. These are generally seen in patients who are immunocompromised, and include invasive candidiasis, invasive aspergillosis, and certain emerging fungal infections.-Invasive...
,
pramiconazolePramiconazole is a triazole antifungal undergoing research for the treatment of acute skin and mucosal fungal infections.It is developed by Barrier Therapeutics....
, and
posaconazolePosaconazole is a triazole antifungal drug.Posaconazole is marketed in the United States, the European Union, and in other countries by Schering-Plough under the trade name Noxafil...
.
The triazole plant protection fungicides include epoxiconazoleEpoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia . Epoxiconazole also limits the production of conidia...
, triadimenol, propiconazolePropiconazole is a triazole fungicide, also known as a DMI, or demethylation inhibiting fungicide due to its binding with and inhibiting the 14-alpha demethylase enzyme from demethylating a precursor to ergosterol. Without this demethylation step, the ergosterols are not incorporated into the...
, metconazole, cyproconazole, tebuconazoleTebuconazole is a triazole fungicide used agriculturally to treat plant pathogenic fungi.Though the U.S. Food and Drug Administration considers this fungicide to be safe for humans, it may still pose a risk...
, flusilazoleFlusilazole is an organosilicon fungicide invented by DuPont, which is used to control fungal infections on a variety of fruit and vegetable crops. It is moderately toxic to animals and has been shown to produce birth defects and embryotoxicity at high doses....
and paclobutrazolPaclobutrazol, PBZ is a plant growth retardant and triazole fungicide. It is a known opponent of the plant hormone gibberellin...
.
Importance in agriculture
Due to spreading resistance of plant pathogens towards fungicides of the strobilurin class , control of fungi such as
Septoria tritici or
Gibberella zeae relies heavily on triazoles.
Related heterocycles
- Imidazole
Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is a diazole and is classified as an alkaloid. Imidazole refers to the parent compound, whereas imidazoles are a class of heterocycles with similar ring structure, but varying substituents...
, an analog with two nonadjacent nitrogen atoms
- Pyrazole
Pyrazole refers both to the class of simple aromatic ring organic compounds of the heterocyclic diazole series characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions, and to the unsubstituted parent compound...
, an analog with two adjacent nitrogen atoms
- Tetrazole
Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen and one carbon atom . The simplest is tetrazole itself, CN4H2. They are unknown in nature...
, an analog with four nitrogen atoms
External links
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GFDL.
