Fenarimol

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
CAS Number	60168-88-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:83686;
ChemSpider	39394;
ECHA InfoCard	100.056.432
PubChem CID	43226;
UNII	O088GU930Q ;
CompTox Dashboard (EPA)	DTXSID2032390 ;
	InChI 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;
	SMILES Clc1ccc(cc1)C(O)(c2ccccc2Cl)c3cncnc3;
Properties
Chemical formula	C17H12Cl2N2O
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)
Boiling point	240 °C (464 °F; 513 K) (decomposition)
Solubility in water	13.7 mg/L at 25 °C
Solubility in other solvents	Soluble in acetone, xylene and methanol
Vapor pressure	65 μ Pa (25 °C)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>2000 mg·kg−1 (oral, Rat)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

History

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]

Synthesis

Fenarimol is made by the reaction of 2,4'-dichlorobenzophenone with an organolithium pyrimidine made via bromine-lithium exchange.^[2]

References

^ ^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.

External links

Fenarimol in the Pesticide Properties DataBase (PPDB)

[EU-1] EU-Data.

[clayden-2] 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.

[3] GB 1218623 "Substituted-5-pyrimidine compounds "

[ReynoldsLim2018-4] 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.

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