Fenarimol

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
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
3D model (JSmol)
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
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)[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).
Infobox references

History

Fenarimol was developed by Eli Lilly & 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]

Fenarimolsynth

References
  1. EU-Data.
  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 "
  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.
  • Fenarimol in the Pesticide Properties DataBase (PPDB)
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