Fenarimol

Last updated
Fenarimol
Fenarimol.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless 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 solventsSoluble 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).

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]

Contents

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]

Fenarimolsynth.svg

Related Research Articles

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Pyrimidine is an aromatic, heterocyclic, organic compound similar to pyridine. One of the three diazines, it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine and pyridazine.

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<span class="mw-page-title-main">Matthew Todd (chemist)</span> British chemist (born 1973)

Matthew Houghton Todd is a British chemist and the Professor and Chair of Drug Discovery of the School of Pharmacy at University College London. He is the founder of Open Source Malaria (OSM) and his research focuses on drug discovery and development for this disease. Recently, he has expanded to other areas, particularly neglected diseases such as tuberculosis and mycetoma in the Open Source Tuberculosis (OSTB) and Open Source Mycetoma (MycetOS) project, through a collaboration with the Drugs for Neglected Diseases Initiative and Erasmus MC. In addition, he has some research activity in catalysis and methodology.

References

  1. 1 2 3 4 5 EU-Data.
  2. 1 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.