Prochloraz

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide

| image = Prochloraz.svg

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| tradename = Abavit, Ascurit, Dibavit, Mirage, Octave, Omega, Prelude, Rival, Sporgon, Sportak, Sprint, Tenor{{cite book| vauthors = ((Anonymous AC05372279)) |title=Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments / Pharmaceuticals|url=https://books.google.com/books?id=OtVZqdPHsm8C&pg=PA576|year=1997|publisher=United Nations Publications|isbn=978-92-1-130219-6|pages=576–}}{{Dead link|date=March 2023 |bot=InternetArchiveBot |fix-attempted=yes }}{{cite book| vauthors = Milne GW |title=Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties|url=https://books.google.com/books?id=oWdc2qcb3QsC&pg=PA517|date=2 September 2005|publisher=John Wiley & Sons|isbn=978-0-471-73661-5|pages=517–}}

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| CAS_number = 67747-09-5

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| PubChem = 73665

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| ChemSpiderID_Ref =

| ChemSpiderID = 159925

| UNII = 99SFL01YCL

| KEGG = C11182

| ChEBI = 8434

| ChEMBL = 522782

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| C=15 | H=16 | Cl=3 | N=3 | O=2

| SMILES = CCCN(CCOC1=C(C=C(C=C1Cl)Cl)Cl)C(=O)N2C=CN=C2

| StdInChI_Ref =

| StdInChI = 1S/C15H16Cl3N3O2/c1-10(2)21(15(22)20-4-3-19-9-20)5-6-23-14-12(17)7-11(16)8-13(14)18/h3-4,7-10H,5-6H2,1-2H3

| StdInChIKey_Ref =

| StdInChIKey = XJABPYGRRIVUOG-UHFFFAOYSA-N

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Prochloraz, brand name Sportak, is an imidazole fungicide that was introduced in 1978{{cite book| vauthors = Carlile B | chapter = Chapter 3.7: Broad-spectrum systemic fungicides |title=Pesticide Selectivity, Health and the Environment| chapter-url = https://books.google.com/books?id=DV_u4w_6RLAC&pg=PA81 |date=28 September 2006|publisher=Cambridge University Press|isbn=978-1-139-45756-9|pages=81–}} and is widely used in Europe, Australia, Asia, and South America within gardening and agriculture to control the growth of fungi.{{cite journal | vauthors = Vinggaard AM, Hass U, Dalgaard M, Andersen HR, Bonefeld-Jørgensen E, Christiansen S, Laier P, Poulsen ME | display-authors = 6 | title = Prochloraz: an imidazole fungicide with multiple mechanisms of action | journal = International Journal of Andrology | volume = 29 | issue = 1 | pages = 186–192 | date = February 2006 | pmid = 16466539 | doi = 10.1111/j.1365-2605.2005.00604.x | doi-access = free }}{{cite book| vauthors = Paranjape K, Gowariker V, Krishnamurthy VN, Gowariker S | chapter = Prochloraz fungicide |title=The Pesticide Encyclopedia| chapter-url = https://books.google.com/books?id=cnDHBgAAQBAJ&pg=PA406|date=22 December 2014|publisher=CABI|isbn=978-1-78064-014-3|pages=406–}} It is not registered for use in the United States.

Similarly to other azole fungicides, prochloraz is an inhibitor of the enzyme lanosterol 14α-demethylase (CYP51A1), which is necessary for the production of ergosterol – an essential component of the fungal cell membrane – from lanosterol.{{cite book | vauthors = Sanderson JT | chapter = Disruptors of Androgen Action and Synthesis | veditors = Darbre PD |title=Endocrine Disruption and Human Health | chapter-url = https://books.google.com/books?id=yOOcBAAAQBAJ&pg=PA86 |date=21 March 2015 |publisher=Elsevier Science |isbn=978-0-12-801120-1 |pages=86– }} The agent is a broad-spectrum, protective and curative fungicide, effective against Alternaria spp., Botrytis spp., Erysiphe spp., Helminthosporium spp., Fusarium spp., Pseudocerosporella spp., Pyrenophora spp., Rhynchosporium spp., and Septoria spp.

Like many imidazole and triazole fungicides and antifungal medications, prochloraz is not particularly selective in its actions. In addition to inhibition of lanosterol 14α-demethylase, prochloraz has also been found to act as an antagonist of the androgen and estrogen receptors, as an agonist of the aryl hydrocarbon receptor, and as an inhibitor of enzymes in the steroidogenesis pathway such as CYP17A1 and aromatase. In accordance, it has been shown to produce reproductive malformations in mice. As such, prochloraz is considered to be an endocrine disruptor.