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Fenarimol

From Wikipedia, the free encyclopedia
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 InfoCard100.056.432Edit this at Wikidata
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 mass331.20 g·mol−1
AppearanceColorless powder with aromatic odor
Melting point117 to 119 °C (243 to 246 °F; 390 to 392 K)[1]
Boiling point240 °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 pressure65 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Fenarimol, sold under the tradenamesBloc,Rimidin andRubigan, is afungicide which acts againstrusts,blackspot andmildew fungi. It is used onornamental plants, trees,lawns, tomatoes, peppers, eggplants,cucumbers and melons. It is mainly used to control powdery mildew. It works by inhibiting the fungus'sbiosynthesis of importantsteroid molecules (via blockade of theCYP51 enzyme).[2]

History

[edit]

Fenarimol was developed byEli Lilly and Company around 1971.[3]

As of early 2018, derivatives of this compound are being researched in anopen source manner for possible treatment ofeumycetoma.[4]

Synthesis

[edit]

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

Fenarimolsynth

References

[edit]
  1. ^abcdeEU-Data.
  2. ^abClayden 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.

External links

[edit]
  • Fenarimol in the Pesticide Properties DataBase (PPDB)
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