From Wikipedia, the free encyclopedia
Prochloraz Trade names Abavit, Ascurit, Dibavit, Mirage, Octave, Omega, Prelude, Rival, Sporgon, Sportak, Sprint, Tenor[ 1] [ 2]
N -propyl-N -[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide
CAS Number PubChem CID ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.060.885 Formula C 15 H 16 Cl 3 N 3 O 2 Molar mass 376.662 g/mol g·mol−1 3D model (JSmol )
CCCN(CCOC1=C(C=C(C=C1Cl)Cl)Cl)C(=O)N2C=CN=C2
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
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 [Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments / Pharmaceuticals ] ; Consolidated list of products whose consumption and/or sale have been banned, withdrawn, severely restricted or not approved by governments.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 . {{cite book }}
: CS1 maint: numeric names: authors list (link )
^ a b G. W. A. Milne (2 September 2005). Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties . John Wiley & Sons. pp. 517–. ISBN 978-0-471-73661-5 .
^ Bill Carlile (28 September 2006). 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, Laier P, Poulsen ME (2006). "Prochloraz: an imidazole fungicide with multiple mechanisms of action". Int. J. Androl . 29 (1): 186–92. doi :10.1111/j.1365-2605.2005.00604.x . PMID 16466539 .
^ a b c Kalyani Paranjape; Vasant Gowariker; V N Krishnamurthy; Sugha Gowariker (22 December 2014). The Pesticide Encyclopedia . CABI. pp. 406–. ISBN 978-1-78064-014-3 .
^ a b c d e Philippa D. Darbre (21 March 2015). Endocrine Disruption and Human Health . Elsevier Science. pp. 86–. ISBN 978-0-12-801120-1 .
External links
Prochloraz in the Pesticide Properties DataBase (PPDB)
AR Tooltip Androgen receptor
Agonists SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown