Fenarimol | CAS#60168-88-9 | fungicide

MedKoo Cat#: 461332 | Name: Fenarimol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fenarimol is a pyrimidine-type fungicide that exhibits potent inhibitory activity against BR biosynthesis.

Chemical Structure

Fenarimol

CAS#60168-88-9

Theoretical Analysis

MedKoo Cat#: 461332

Name: Fenarimol

CAS#: 60168-88-9

Chemical Formula: C17H12Cl2N2O

Exact Mass: 330.0327

Molecular Weight: 331.19

Elemental Analysis: C, 61.65; H, 3.65; Cl, 21.41; N, 8.46; O, 4.83

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 450.00	2 Weeks

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Related CAS #

No Data

Synonym

Fenarimol; Rimidin; Rubigan;

IUPAC/Chemical Name

(2-chlorophenyl)(4-chlorophenyl)(pyrimidin-5-yl)methanol

InChi Key

NHOWDZOIZKMVAI-UHFFFAOYSA-N

InChi Code

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

SMILES Code

ClC1=CC=C(C=C1)C(C2=CN=CN=C2)(O)C3=CC=CC=C3Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 331.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Oh K, Matsumoto T, Yamagami A, Hoshi T, Nakano T, Yoshizawa Y. Fenarimol, a Pyrimidine-Type Fungicide, Inhibits Brassinosteroid Biosynthesis. Int J Mol Sci. 2015 Jul 29;16(8):17273-88. doi: 10.3390/ijms160817273. PubMed PMID: 26230686; PubMed Central PMCID: PMC4581192. 2: Park M, Han J, Ko JJ, Lee WS, Yoon TK, Lee K, Bae J. Maternal exposure to fenarimol promotes reproductive performance in mouse offspring. Toxicol Lett. 2011 Sep 10;205(3):241-9. doi: 10.1016/j.toxlet.2011.05.1040. Epub 2011 Jun 22. PubMed PMID: 21722721. 3: Parodi DA, Sjarif J, Chen Y, Allard P. Reproductive toxicity and meiotic dysfunction following exposure to the pesticides Maneb, Diazinon and Fenarimol. Toxicol Res (Camb). 2015 May;4(3):645-654. PubMed PMID: 25984295; PubMed Central PMCID: PMC4433152. 4: Keenan M, Chaplin JH, Alexander PW, Abbott MJ, Best WM, Khong A, Botero A, Perez C, Cornwall S, Thompson RA, White KL, Shackleford DM, Koltun M, Chiu FC, Morizzi J, Ryan E, Campbell M, von Geldern TW, Scandale I, Chatelain E, Charman SA. Two analogues of fenarimol show curative activity in an experimental model of Chagas disease. J Med Chem. 2013 Dec 27;56(24):10158-70. doi: 10.1021/jm401610c. Epub 2013 Dec 4. PubMed PMID: 24304150; PubMed Central PMCID: PMC3884847. 5: Keenan M, Alexander PW, Diao H, Best WM, Khong A, Kerfoot M, Thompson RC, White KL, Shackleford DM, Ryan E, Gregg AD, Charman SA, von Geldern TW, Scandale I, Chatelain E. Design, structure-activity relationship and in vivo efficacy of piperazine analogues of fenarimol as inhibitors of Trypanosoma cruzi. Bioorg Med Chem. 2013 Apr 1;21(7):1756-63. doi: 10.1016/j.bmc.2013.01.050. Epub 2013 Jan 31. PubMed PMID: 23462713. 6: Watermann BT, Albanis TA, Dagnac T, Gnass K, Ole Kusk K, Sakkas VA, Wollenberger L. Effects of methyltestosterone, letrozole, triphenyltin and fenarimol on histology of reproductive organs of the copepod Acartia tonsa. Chemosphere. 2013 Jul;92(5):544-54. doi: 10.1016/j.chemosphere.2013.03.053. Epub 2013 May 9. PubMed PMID: 23664474. 7: Khan S, Bhatia T, Trivedi P, Satyanarayana GN, Mandrah K, Saxena PN, Mudiam MK, Roy SK. Selective solid-phase extraction using molecularly imprinted polymer as a sorbent for the analysis of fenarimol in food samples. Food Chem. 2016 May 15;199:870-5. doi: 10.1016/j.foodchem.2015.12.091. Epub 2015 Dec 29. PubMed PMID: 26776046. 8: De Waard MA, Van Nistelrooy JG. Induction of fenarimol-efflux activity in Aspergillus nidulans by fungicides inhibiting sterol biosynthesis. J Gen Microbiol. 1981 Oct;126(2):483-9. PubMed PMID: 7040601. 9: Zhang H, Wang X, Zhuang S, Qian M, Jiang K, Wang X, Xu H, Qi P, Wang Q. Enantioselective separation and simultaneous determination of fenarimol and nuarimol in fruits, vegetables, and soil by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2012 Oct;404(6-7):1983-91. doi: 10.1007/s00216-012-6325-8. Epub 2012 Sep 6. PubMed PMID: 22955670. 10: Hirsch KS, Adams ER, Hoffman DG, Markham JK, Owen NV. Studies to elucidate the mechanism of fenarimol-induced infertility in male rats. Toxicol Appl Pharmacol. 1986 Dec;86(3):391-9. PubMed PMID: 3787632. 11: Keenan M, Abbott MJ, Alexander PW, Armstrong T, Best WM, Berven B, Botero A, Chaplin JH, Charman SA, Chatelain E, von Geldern TW, Kerfoot M, Khong A, Nguyen T, McManus JD, Morizzi J, Ryan E, Scandale I, Thompson RA, Wang SZ, White KL. Analogues of fenarimol are potent inhibitors of Trypanosoma cruzi and are efficacious in a murine model of Chagas disease. J Med Chem. 2012 May 10;55(9):4189-204. doi: 10.1021/jm2015809. Epub 2012 Apr 27. PubMed PMID: 22536986. 12: de Castro VL, de Mello MA, Diniz C, Morita L, Zucchi T, Poli P. Neurodevelopmental effects of perinatal fenarimol exposure on rats. Reprod Toxicol. 2007 Jan;23(1):98-105. Epub 2006 Sep 12. PubMed PMID: 17070007. 13: Vinggaard AM, Jacobsen H, Metzdorff SB, Andersen HR, Nellemann C. Antiandrogenic effects in short-term in vivo studies of the fungicide fenarimol. Toxicology. 2005 Feb 1;207(1):21-34. PubMed PMID: 15590119. 14: Zeiman E, Greenblatt CL, Elgavish S, Khozin-Goldberg I, Golenser J. Mode of action of fenarimol against Leishmania spp. J Parasitol. 2008 Feb;94(1):280-6. doi: 10.1645/GE-1259.1. PubMed PMID: 18372651. 15: de Castro VL, de Mello MA, Poli P, Zucchi TM. Prenatal and perinatal fenarimol-induced genotoxicity in leukocytes of in vivo treated rats. Mutat Res. 2005 May 2;583(1):95-104. PubMed PMID: 15866470. 16: Andersen HR, Bonefeld-Jørgensen EC, Nielsen F, Jarfeldt K, Jayatissa MN, Vinggaard AM. Estrogenic effects in vitro and in vivo of the fungicide fenarimol. Toxicol Lett. 2006 May 25;163(2):142-52. Epub 2005 Dec 1. PubMed PMID: 16324804. 17: Poli P, de Mello MA, Buschini A, de Castro VL, Restivo FM, Rossi C, Zucchi TM. Evaluation of the genotoxicity induced by the fungicide fenarimol in mammalian and plant cells by use of the single-cell gel electrophoresis assay. Mutat Res. 2003 Sep 9;540(1):57-66. PubMed PMID: 12972058. 18: Hirsch KS, Weaver DE, Black LJ, Falcone JF, MacLusky NJ. Inhibition of central nervous system aromatase activity: a mechanism for fenarimol-induced infertility in the male rat. Toxicol Appl Pharmacol. 1987 Nov;91(2):235-45. PubMed PMID: 3672523. 19: Palut D, Ludwicki JK, Wiadrowska B. The effect of fenarimol on marker enzymes in rat liver in two-stages model of hepatocarcinogenesis. Rocz Panstw Zakl Hig. 1997;48(3):205-16. PubMed PMID: 9400092. 20: Jacobson T, Sundelin B. Reproductive effects of the endocrine disruptor fenarimol on a Baltic amphipod Monoporeia affinis. Environ Toxicol Chem. 2006 Apr;25(4):1126-31. PubMed PMID: 16629152.