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;
	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)[1]
Boiling point	240 °C (464 °F; 513 K) (decomposition)[1]
Solubility in water	13.7 mg·L−1 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):
LD50 (median dose)	>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

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

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

References

1 2 3 4 5 EU-Data.
1 2 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.
↑ GB 1218623 "Substituted-5-pyrimidine compounds "
↑ 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. doi:10.1080/026520399283678. PMID 10789375.
↑ 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. doi:10.1006/taap.2001.9347. ISSN 0041-008X. PMID 11884232.

External links

Fenarimol in the Pesticide Properties DataBase (PPDB)

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

[clayden-2] 1 2 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. doi:10.1080/026520399283678. PMID 10789375.

[Raun_AndersenVinggaard2002-5] 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. doi:10.1006/taap.2001.9347. ISSN 0041-008X. PMID 11884232.