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MedKoo Cat#: 540118 | Name: Epoxiconazole

Description:

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

Epoxiconazole is a 14-α demethylase inhibitor that inhibits ergosterol synthesis and fungal cell wall formation. It may inhibit aromatase and act as an endocrine distrupter.

Chemical Structure

Epoxiconazole
Epoxiconazole
CAS#133855-98-8

Theoretical Analysis

MedKoo Cat#: 540118

Name: Epoxiconazole

CAS#: 133855-98-8

Chemical Formula: C17H13ClFN3O

Exact Mass: 329.0731

Molecular Weight: 329.75

Elemental Analysis: C, 61.92; H, 3.97; Cl, 10.75; F, 5.76; N, 12.74; O, 4.85

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Related CAS #
106325-08-0
Synonym
BAS 480F; BAS480F; BAS-480-F; EC 406 850 2; EC-406-850-2; EC4068502; Epoxiconazole; Epoxiconazol; OPUS; epoxyconazole
IUPAC/Chemical Name
1-[[(2S,3R)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole
InChi Key
ZMYFCFLJBGAQRS-IAGOWNOFSA-N
InChi Code
InChI=1S/C17H13ClFN3O/c18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h1-8,10-11,16H,9H2/t16-,17-/m1/s1
SMILES Code
FC1=CC=C([C@@]2(CN3N=CN=C3)O[C@@H]2C4=CC=CC=C4Cl)C=C1
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 329.75 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.

Recalculate based on batch purity %
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
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Ecotoxicol Environ Saf. 2014 Sep;107:71-6. doi: 10.1016/j.ecoenv.2014.02.013. Epub 2014 Jun 4. PubMed PMID: 24907454. 5: Xu C, Liu Q, Huan F, Qu J, Liu W, Gu A, Wang Y, Jiang Z. Changes in Gut Microbiota May Be Early Signs of Liver Toxicity Induced by Epoxiconazole in Rats. Chemotherapy. 2014;60(2):135-42. PubMed PMID: 25766299. 6: Rey Moreno MC, Fussell KC, Gröters S, Schneider S, Strauss V, Stinchcombe S, Fegert I, Veras M, van Ravenzwaay B. Epoxiconazole-induced degeneration in rat placenta and the effects of estradiol supplementation. Birth Defects Res B Dev Reprod Toxicol. 2013 Jun;98(3):208-21. doi: 10.1002/bdrb.21055. Epub 2013 Apr 29. PubMed PMID: 23749492. 7: Schneider S, Hofmann T, Stinchcombe S, Moreno MC, Fegert I, Strauss V, Gröters S, Fabian E, Thiaener J, Fussell KC, van Ravenzwaay B. Species differences in developmental toxicity of epoxiconazole and its relevance to humans. Birth Defects Res B Dev Reprod Toxicol. 2013 Jun;98(3):230-46. doi: 10.1002/bdrb.21058. Epub 2013 Apr 29. PubMed PMID: 23630118. 8: de Castro VL, Maia AH. Prenatal epoxiconazole exposure effects on rat postnatal development. Birth Defects Res B Dev Reprod Toxicol. 2012 Apr;95(2):123-9. doi: 10.1002/bdrb.20345. Epub 2011 Dec 2. PubMed PMID: 22140080. 9: Lichiheb N, Bedos C, Personne E, Benoit P, Bergheaud V, Fanucci O, Bouhlel J, Barriuso E. Measuring Leaf Penetration and Volatilization of Chlorothalonil and Epoxiconazole Applied on Wheat Leaves in a Laboratory-Scale Experiment. J Environ Qual. 2015 Nov;44(6):1782-90. doi: 10.2134/jeq2015.03.0165. PubMed PMID: 26641330. 10: Nélieu S, Delarue G, Ollivier E, Awad P, Fraillon F, Pelosi C. Evaluation of epoxiconazole bioavailability in soil to the earthworm Aporrectodea icterica. Environ Sci Pollut Res Int. 2016 Feb;23(4):2977-86. doi: 10.1007/s11356-015-5270-4. Epub 2015 Aug 29. PubMed PMID: 26315591. 11: Deweer C, Siah A, Sahmer K, Halama P. Evolution of Mycosphaerella graminicola resistance to epoxiconazole and pyrifenox in northern France. Commun Agric Appl Biol Sci. 2012;77(3):109-15. PubMed PMID: 23878964. 12: Ajigboye OO, Murchie E, Ray RV. Foliar application of isopyrazam and epoxiconazole improves photosystem II efficiency, biomass and yield in winter wheat. Pestic Biochem Physiol. 2014 Sep;114:52-60. doi: 10.1016/j.pestbp.2014.07.003. Epub 2014 Jul 17. PubMed PMID: 25175650. 13: Chambers JE, Greim H, Kendall RJ, Segner H, Sharpe RM, Van Der Kraak G. Human and ecological risk assessment of a crop protection chemical: a case study with the azole fungicide epoxiconazole. Crit Rev Toxicol. 2014 Feb;44(2):176-210. doi: 10.3109/10408444.2013.855163. Epub 2013 Nov 25. Review. PubMed PMID: 24274332. 14: Gutenberger A, Zeisler VV, Berghaus R, Auweter H, Schreiber L. Effects of poly- and monodisperse surfactants on 14C-epoxiconazole diffusion in isolated cuticles of Prunus laurocerasus. Pest Manag Sci. 2013 Apr;69(4):512-9. doi: 10.1002/ps.3402. Epub 2012 Oct 9. PubMed PMID: 23044821. 15: Liang H, Qiu J, Li L, Li W, Zhou Z, Liu F, Qiu L. Stereoselective dissipation of epoxiconazole in grape (Vitis vinifera cv. Kyoho) and soil under field conditions. Chemosphere. 2012 May;87(8):982-7. doi: 10.1016/j.chemosphere.2012.02.038. Epub 2012 Mar 11. PubMed PMID: 22414382. 16: Stinchcombe S, Schneider S, Fegert I, Rey Moreno MC, Strauss V, Gröters S, Fabian E, Fussell KC, Pigott GH, van Ravenzwaay B. Effects of estrogen coadministration on epoxiconazole toxicity in rats. Birth Defects Res B Dev Reprod Toxicol. 2013 Jun;98(3):247-59. doi: 10.1002/bdrb.21059. Epub 2013 May 29. PubMed PMID: 23720304. 17: Li Y, Zhang M, Li S, Lv R, Chen P, Liu R, Liang G, Yin L. The Use of the Nematode Caenorhabditis elegans to Evaluate the Adverse Effects of Epoxiconazole Exposure on Spermatogenesis. Int J Environ Res Public Health. 2016 Oct 8;13(10). pii: E993. PubMed PMID: 27740608; PubMed Central PMCID: PMC5086732. 18: Honorato Júnior J, Zambolim L, Aucique-Pérez CE, Resende RS, Rodrigues FA. Photosynthetic and antioxidative alterations in coffee leaves caused by epoxiconazole and pyraclostrobin sprays and Hemileia vastatrix infection. Pestic Biochem Physiol. 2015 Sep;123:31-9. doi: 10.1016/j.pestbp.2015.01.016. Epub 2015 Feb 11. PubMed PMID: 26267050. 19: Pan X, Dong F, Xu J, Liu X, Cheng Y, Chen Z, Liu N, Chen X, Tao Y, Zheng Y. Comparison of different cleanup procedures for oil crops based on the development of a trace analytical method for the determination of pyraclostrobin and epoxiconazole. J Sep Sci. 2014 Dec;37(24):3669-76. doi: 10.1002/jssc.201400596. Epub 2014 Nov 6. PubMed PMID: 25287054. 20: Zhang X, Luo F, Lou Z, Lu M, Chen Z. Simultaneous and enantioselective determination of cis-epoxiconazole and indoxacarb residues in various teas, tea infusion and soil samples by chiral high performance liquid chromatography coupled with tandem quadrupole-time-of-flight mass spectrometry. J Chromatogr A. 2014 Sep 12;1359:212-23. doi: 10.1016/j.chroma.2014.07.058. Epub 2014 Jul 24. PubMed PMID: 25108768.