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Fenarimol
Names
IUPAC name
(R /S )-2,4′-Dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol
Other names
α-(2-Chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.056.432
UNII
InChI=1S/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H
Key: NHOWDZOIZKMVAI-UHFFFAOYSA-N
InChI=1/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H
Key: NHOWDZOIZKMVAI-UHFFFAOYAN
Clc1ccc(cc1)C(O)(c2ccccc2Cl)c3cncnc3
Properties
C 17 H 12 Cl 2 N 2 O
Molar mass
331.20 g·mol−1
Appearance
Colorless powder with aromatic odor
Melting point
117 to 119 °C (243 to 246 °F; 390 to 392 K)[ 1]
Boiling point
240 °C (464 °F; 513 K) (decomposition)[ 1]
13.7 mg/L at 25 °C
Solubility in other solvents
Soluble in acetone, xylene and methanol[ 1]
Vapor pressure
65 μ Pa (25 °C)[ 1]
Hazards
Lethal dose or concentration (LD, LC):
>2000 mg·kg−1 (oral, Rat)[ 1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Fenarimol , sold under the tradenames Bloc , Rimidin and Rubigan , is a fungicide which acts against rusts , blackspot and mildew fungi. It is used on ornamental plants , trees, lawns , tomatoes, peppers, eggplants, cucumbers and melons . It is mainly used to control powdery mildew. It works by inhibiting the fungus's biosynthesis of important steroid molecules (via blockade of the CYP51 enzyme).[ 2]
Fenarimol was developed by Eli Lilly and Company around 1971.[ 3]
As of early 2018, derivatives of this compound are being researched in an open source manner for possible treatment of eumycetoma .[ 4]
Fenarimol is made by the reaction of 2,4'-dichlorobenzophenone with an organolithium pyrimidine made via bromine-lithium exchange.[ 2]
^ a b c d e EU-Data .
^ a b Clayden J, Greeves N, Warren S (2005). Organic chemistry (Reprinted (with corrections) ed.). Oxford [u.a.]: Oxford Univ. Press. pp. 216 . ISBN 978-0-19-850346-0 .
^ GB 1218623 "Substituted-5-pyrimidine compounds "
^ Reynolds, Todd B.; Lim, Wilson; Melse, Youri; Konings, Mickey; Phat Duong, Hung; Eadie, Kimberly; Laleu, Benoît; Perry, Benjamin; Todd, Matthew H.; Ioset, Jean-Robert; van de Sande, Wendy W. J. (2018). "Addressing the most neglected diseases through an open research model: The discovery of fenarimols as novel drug candidates for eumycetoma" . PLOS Neglected Tropical Diseases . 12 (4): e0006437. doi :10.1371/journal.pntd.0006437 . ISSN 1935-2735 . PMC 5940239 . PMID 29698504 .
Fenarimol 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