From Wikipedia, the free encyclopedia
Chemical compound
Prochloraz
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Trade names | Abavit, Ascurit, Dibavit, Mirage, Octave, Omega, Prelude, Rival, Sporgon, Sportak, Sprint, Tenor
[1]
[2] |
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N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide
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CAS Number | |
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PubChem
CID | |
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ChemSpider | |
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UNII | |
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KEGG | |
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ChEBI | |
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ChEMBL | |
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CompTox Dashboard (
EPA) | |
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ECHA InfoCard |
100.060.885
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Formula | C15H16Cl3N3O2 |
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Molar mass | 376.66 g·mol−1 |
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3D model (
JSmol) | |
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CCCN(CCOC1=C(C=C(C=C1Cl)Cl)Cl)C(=O)N2C=CN=C2
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InChI=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 Key:XJABPYGRRIVUOG-UHFFFAOYSA-N
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Prochloraz, brand name Sportak, is an
imidazole
fungicide that was introduced in 1978
[3] and is widely used in
Europe,
Australia,
Asia, and
South America within
gardening and
agriculture to control the growth of
fungi.
[4]
[5] It is not registered for use in the
United States.
[5] 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.
[6] 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.
[5]
[2]
Like many imidazole and
triazole fungicides and
antifungal medications, prochloraz is not particularly selective in its actions.
[4]
[6] 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.
[4]
[6] In accordance, it has been shown to produce
reproductive
malformations in mice.
[4]
[6] As such, prochloraz is considered to be an
endocrine disruptor.
[4]
[6]
See also
References
-
^ Anonymous AC05372279 (1997).
Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments / Pharmaceuticals. United Nations Publications. pp. 576–.
ISBN
978-92-1-130219-6.[
permanent dead link]
- ^
a
b Milne GW (2 September 2005).
Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties. John Wiley & Sons. pp. 517–.
ISBN
978-0-471-73661-5.
-
^ Carlile B (28 September 2006).
"Chapter 3.7: Broad-spectrum systemic fungicides". Pesticide Selectivity, Health and the Environment. Cambridge University Press. pp. 81–.
ISBN
978-1-139-45756-9.
- ^
a
b
c
d
e Vinggaard AM, Hass U, Dalgaard M, Andersen HR, Bonefeld-Jørgensen E, Christiansen S, et al. (February 2006).
"Prochloraz: an imidazole fungicide with multiple mechanisms of action". International Journal of Andrology. 29 (1): 186–192.
doi:
10.1111/j.1365-2605.2005.00604.x.
PMID
16466539.
- ^
a
b
c Paranjape K, Gowariker V, Krishnamurthy VN, Gowariker S (22 December 2014).
"Prochloraz fungicide". The Pesticide Encyclopedia. CABI. pp. 406–.
ISBN
978-1-78064-014-3.
- ^
a
b
c
d
e Sanderson JT (21 March 2015).
"Disruptors of Androgen Action and Synthesis". In Darbre PD (ed.). Endocrine Disruption and Human Health. Elsevier Science. pp. 86–.
ISBN
978-0-12-801120-1.
External links
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Prochloraz in the Pesticide Properties DataBase (PPDB)
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ARTooltip Androgen receptor | Agonists | |
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SARMsTooltip Selective androgen receptor modulator | |
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Antagonists | |
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GPRC6A | |
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ERTooltip Estrogen receptor | Agonists |
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2-Hydroxyestradiol
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3α-Androstanediol
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3α,5α-Dihydrolevonorgestrel
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3β,5α-Dihydrolevonorgestrel
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3α-Hydroxytibolone
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3β-Hydroxytibolone
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3β-Androstanediol
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4-Androstenediol
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4-Androstenedione
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4-Fluoroestradiol
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4-Hydroxyestradiol
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4-Hydroxyestrone
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4-Methoxyestradiol
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4-Methoxyestrone
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5-Androstenediol
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7-Oxo-DHEA
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7α-Hydroxy-DHEA
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7α-Methylestradiol
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7β-Hydroxyepiandrosterone
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8,9-Dehydroestradiol
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8,9-Dehydroestrone
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8β-VE2
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10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
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11β-Chloromethylestradiol
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16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
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17α-Estradiol (
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17α-Dihydroequilin
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17α-Ethynyl-3α-androstanediol
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17α-Ethynyl-3β-androstanediol
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17β-Methyl-17α-dihydroequilenin
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RU-16117
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EGCG,
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agnuside,
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Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:
ERX-11
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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