Fenarimol

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Fenarimol
Fenarimol.svg
Names
IUPAC name
(RS)-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
Properties
C17H12Cl2N2O
Molar mass 331.2
Appearance Colorless powder with aromatic odour
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−1 at 25 °C
Solubility 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, Ratte)[1]
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.[2]

Description[edit]

Fenarimol was developed by Eli Lilly & Company around 1971.[3]

Health Risk

Fenarimol can lead to increased growth of MCF7 breast cancer cells.[4] It has been found to be an endocrine disruptor, acting as a xenoestrogen and antiandrogen.[5]

Synthesis[edit]

Fenarimol is made by the reaction of a diarylketon with an organolithium derived by halogen-metal exchange.[2]

Fenarimolsynth

External links[edit]

  • Fenarimol in the Pesticide Properties DataBase (PPDB)

References[edit]

  1. ^ a b c d e EU-Data.
  2. ^ a b Clayden J, Greeves N, Warren S (2005). Organic chemistry (Reprinted (with corrections) ed.). Oxford [u.a.]: Oxford Univ. Press. p. 216. ISBN 978-0-19-850346-0. 
  3. ^ GB 1218623  "Substituted-5-pyrimidine compounds "
  4. ^ Vinggaard, Anne Marie; Breinholt, Vibeke; Larsen, John Christian (1 December 1999). "Screening of selected pesticides for oestrogen receptor activation in vitro". Food Additives and Contaminants. 16 (12): 533–542. PMID 10789375. doi:10.1080/026520399283678. 
  5. ^ Raun Andersen, Helle; Vinggaard, Anne Marie; Høj Rasmussen, Thomas; Gjermandsen, Irene Marianne; Cecilie Bonefeld-Jørgensen, Eva (2002). "Effects of Currently Used Pesticides in Assays for Estrogenicity, Androgenicity, and Aromatase Activity in Vitro". Toxicology and Applied Pharmacology. 179 (1): 1–12. ISSN 0041-008X. doi:10.1006/taap.2001.9347.