Prochloraz | CAS#67747-09-5 | fungicide

MedKoo Cat#: 55850 | Name: Prochloraz

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Description:

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

Prochloraz is a broad-spectrum contact imidazol fungicide used against several diseases in wheat, barley and oleaginous plants but also for treatment of flower production. It is a fungicide known to have multiple effects on the endocrine system of vertebrates.

Chemical Structure

Prochloraz

CAS#67747-09-5

Theoretical Analysis

MedKoo Cat#: 55850

Name: Prochloraz

CAS#: 67747-09-5

Chemical Formula: C15H16Cl3N3O2

Exact Mass: 375.0308

Molecular Weight: 376.66

Elemental Analysis: C, 47.83; H, 4.28; Cl, 28.23; N, 11.16; O, 8.50

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
5g	USD 950.00	2 Weeks
10g	USD 1,650.00	2 Weeks

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Synonym

Prochloraz; Prelude; Prochloraz; Sporgon;

IUPAC/Chemical Name

1H-Imidazole-1-carboxamide, N-propyl-N-(2-(2,4,6-trichlorophenoxy)ethyl)-

InChi Key

TVLSRXXIMLFWEO-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H16Cl3N3O2/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h3,5,8-10H,2,4,6-7H2,1H3

SMILES Code

O=C(N1C=CN=C1)N(CCC)CCOC2=C(Cl)C=C(Cl)C=C2Cl

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Prochloraz is an imidazole antifungal. Prochloraz is as an estrogen receptor (ER) and androgen receptor (AR) antagonist and an aromatase inhibitor with IC50 values of 25 μM, 4 μM and 0.3 μM.

In vitro activity:

It was observed that prochloraz induced oxidative stress in cultured human adrenocortical H295R and hepatoma HepG2 cells at non-toxic concentrations. Further, this study used Comet assay to investigate the DNA damaging potential of prochloraz, and found that non-toxic concentrations of prochloraz induced DNA damage in HepG2 cells. These are novel findings, contradicting previous studies in the field of prochloraz and genotoxicity. Reference: Food Chem Toxicol. 2016 May;91:36-41. https://pubmed.ncbi.nlm.nih.gov/26945613/

In vivo activity:

Zebrafish were exposed to different concentrations of prochloraz (10-300 μg/L) until 60 days post hatch (dph), which includes the period of sexual differentiation. For the subsequent 40 days, fish were either held in clean water for depuration or under further continuous exposure. Histological investigations of the gonads revealed persistent effects on sexual differentiation. The sex ratio was skewed towards males and significantly more intersex individuals were found after exposure to prochloraz at 60 dph. Reference: Environ Sci Pollut Res Int. 2015 Nov;22(21):16417-22. https://pubmed.ncbi.nlm.nih.gov/25163568/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	79.65
	DMSO	140.0	371.69
	Ethanol	30.0	79.65
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.33

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 376.66 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

Formulation protocol:

1. Lundqvist J, Hellman B, Oskarsson A. Fungicide prochloraz induces oxidative stress and DNA damage in vitro. Food Chem Toxicol. 2016 May;91:36-41. doi: 10.1016/j.fct.2016.03.002. Epub 2016 Mar 2. PMID: 26945613. 2. Alpertunga B, Kara M, Abudayyak M, Oztas E, Ozden S, Ozhan G. Effects of prochloraz on DNA damage, lipid peroxidation and antioxidant system in vitro. Toxicol Mech Methods. 2014 May;24(4):268-75. doi: 10.3109/15376516.2014.881943. Epub 2014 Jan 27. PMID: 24401010. 3. Baumann L, Knörr S, Keiter S, Nagel T, Segner H, Braunbeck T. Prochloraz causes irreversible masculinization of zebrafish (Danio rerio). Environ Sci Pollut Res Int. 2015 Nov;22(21):16417-22. doi: 10.1007/s11356-014-3486-3. Epub 2014 Aug 28. PMID: 25163568. 4. Dmytriyeva O, Klementiev B, Berezin V, Bock E. Prenatal prochloraz treatment significantly increases pregnancy length and reduces offspring weight but does not affect social-olfactory memory in rats. Exp Toxicol Pathol. 2013 Jul;65(5):591-3. doi: 10.1016/j.etp.2012.06.001. Epub 2012 Jun 21. PMID: 22727564.

In vitro protocol:

In vivo protocol:

1. Baumann L, Knörr S, Keiter S, Nagel T, Segner H, Braunbeck T. Prochloraz causes irreversible masculinization of zebrafish (Danio rerio). Environ Sci Pollut Res Int. 2015 Nov;22(21):16417-22. doi: 10.1007/s11356-014-3486-3. Epub 2014 Aug 28. PMID: 25163568. 2. Dmytriyeva O, Klementiev B, Berezin V, Bock E. Prenatal prochloraz treatment significantly increases pregnancy length and reduces offspring weight but does not affect social-olfactory memory in rats. Exp Toxicol Pathol. 2013 Jul;65(5):591-3. doi: 10.1016/j.etp.2012.06.001. Epub 2012 Jun 21. PMID: 22727564.

1: Liu J, Wang S, Qin T, Li N, Niu Y, Li D, Yuan Y, Geng H, Xiong L, Liu D. Whole transcriptome analysis of Penicillium digitatum strains treatmented with prochloraz reveals their drug-resistant mechanisms. BMC Genomics. 2015 Oct 24;16:855. doi: 10.1186/s12864-015-2043-x. PubMed PMID: 26499483; PubMed Central PMCID: PMC4619488. 2: Alpertunga B, Kara M, Abudayyak M, Oztas E, Ozden S, Ozhan G. Effects of prochloraz on DNA damage, lipid peroxidation and antioxidant system in vitro. Toxicol Mech Methods. 2014 May;24(4):268-75. doi: 10.3109/15376516.2014.881943. Epub 2014 Jan 27. PubMed PMID: 24401010. 3: Baumann L, Knörr S, Keiter S, Nagel T, Segner H, Braunbeck T. Prochloraz causes irreversible masculinization of zebrafish (Danio rerio). Environ Sci Pollut Res Int. 2015 Nov;22(21):16417-22. doi: 10.1007/s11356-014-3486-3. Epub 2014 Aug 28. PubMed PMID: 25163568. 4: Lundqvist J, Hellman B, Oskarsson A. Fungicide prochloraz induces oxidative stress and DNA damage in vitro. Food Chem Toxicol. 2016 May;91:36-41. doi: 10.1016/j.fct.2016.03.002. Epub 2016 Mar 2. PubMed PMID: 26945613. 5: Zhang J, Zhao C, Liu Y, Cao L, Wu Y, Huang Q. Size-Dependent Effect of Prochloraz-Loaded mPEG-PLGA Micro- and Nanoparticles. J Nanosci Nanotechnol. 2016 Jun;16(6):6231-7. PubMed PMID: 27427695. 6: Dalhoff K, Gottardi M, Kretschmann A, Cedergreen N. What causes the difference in synergistic potentials of propiconazole and prochloraz toward pyrethroids in Daphnia magna? Aquat Toxicol. 2016 Mar;172:95-102. doi: 10.1016/j.aquatox.2015.12.007. Epub 2015 Dec 28. PubMed PMID: 26784738. 7: Liu J, Yuan Y, Wu Z, Li N, Chen Y, Qin T, Geng H, Xiong L, Liu D. A novel sterol regulatory element-binding protein gene (sreA) identified in penicillium digitatum is required for prochloraz resistance, full virulence and erg11 (cyp51) regulation. PLoS One. 2015 Feb 20;10(2):e0117115. doi: 10.1371/journal.pone.0117115. eCollection 2015. PubMed PMID: 25699519; PubMed Central PMCID: PMC4336317. 8: Wu Z, Wang S, Yuan Y, Zhang T, Liu J, Liu D. A novel major facilitator superfamily transporter in Penicillium digitatum (PdMFS2) is required for prochloraz resistance, conidiation and full virulence. Biotechnol Lett. 2016 Aug;38(8):1349-57. doi: 10.1007/s10529-016-2113-4. Epub 2016 May 5. PubMed PMID: 27146209. 9: Dang Y, Giesy JP, Wang J, Liu C. Dose-dependent compensation responses of the hypothalamic-pituitary-gonadal-liver axis of zebrafish exposed to the fungicide prochloraz. Aquat Toxicol. 2015 Mar;160:69-75. doi: 10.1016/j.aquatox.2015.01.003. Epub 2015 Jan 8. PubMed PMID: 25625521. 10: Halwachs S, Wassermann L, Lindner S, Zizzadoro C, Honscha W. Fungicide prochloraz and environmental pollutant dioxin induce the ABCG2 transporter in bovine mammary epithelial cells by the arylhydrocarbon receptor signaling pathway. Toxicol Sci. 2013 Feb;131(2):491-501. doi: 10.1093/toxsci/kfs304. Epub 2012 Oct 18. PubMed PMID: 23081912. 11: Xu L, Luan F, Liu H, Gao Y. Dispersive liquid-liquid microextraction combined with non-aqueous capillary electrophoresis for the determination of imazalil, prochloraz and thiabendazole in apples, cherry tomatoes and grape juice. J Sci Food Agric. 2015 Mar 15;95(4):745-51. doi: 10.1002/jsfa.6834. Epub 2014 Aug 13. PubMed PMID: 25048793. 12: Wang J, Yu J, Liu J, Yuan Y, Li N, He M, Qi T, Hui G, Xiong L, Liu D. Novel mutations in CYP51B from Penicillium digitatum involved in prochloraz resistance. J Microbiol. 2014 Sep;52(9):762-70. doi: 10.1007/s12275-014-4112-2. Epub 2014 Aug 2. PubMed PMID: 25085733. 13: Zhang W, He S, Liu Y, Geng Q, Ding G, Guo M, Deng Y, Zhu J, Li J, Cao Y. Preparation and characterization of novel functionalized prochloraz microcapsules using silica-alginate-elements as controlled release carrier materials. ACS Appl Mater Interfaces. 2014 Jul 23;6(14):11783-90. doi: 10.1021/am502541g. Epub 2014 Jul 7. PubMed PMID: 24964350. 14: Dmytriyeva O, Klementiev B, Berezin V, Bock E. Prenatal prochloraz treatment significantly increases pregnancy length and reduces offspring weight but does not affect social-olfactory memory in rats. Exp Toxicol Pathol. 2013 Jul;65(5):591-3. doi: 10.1016/j.etp.2012.06.001. Epub 2012 Jun 21. PubMed PMID: 22727564. 15: Kretschmann A, Gottardi M, Dalhoff K, Cedergreen N. The synergistic potential of the azole fungicides prochloraz and propiconazole toward a short α-cypermethrin pulse increases over time in Daphnia magna. Aquat Toxicol. 2015 May;162:94-101. doi: 10.1016/j.aquatox.2015.02.011. Epub 2015 Mar 5. PubMed PMID: 25797530. 16: Sanabria M, Pessin A, Zanutto MR, Perobelli JE, Guerra MT, Banzato TP, Borges Cdos S, Kempinas Wde G. Absence of effects on the rat sperm quality after subacute exposure to low doses of fungicide prochloraz. J Toxicol Environ Health A. 2015;78(8):481-91. doi: 10.1080/15287394.2015.1010463. PubMed PMID: 25849765. 17: Nielsen FK, Hansen CH, Fey JA, Hansen M, Halling-Sørensen B, Björklund E, Styrishave B. Mixture Effects of 3 Mechanistically Different Steroidogenic Disruptors (Prochloraz, Genistein, and Ketoconazole) in the H295R Cell Assay. Int J Toxicol. 2015 Nov-Dec;34(6):534-42. doi: 10.1177/1091581815599375. Epub 2015 Aug 12. PubMed PMID: 26268768. 18: Faria-Ramos I, Tavares PR, Farinha S, Neves-Maia J, Miranda IM, Silva RM, Estevinho LM, Pina-Vaz C, Rodrigues AG. Environmental azole fungicide, prochloraz, can induce cross-resistance to medical triazoles in Candida glabrata. FEMS Yeast Res. 2014 Nov;14(7):1119-23. doi: 10.1111/1567-1364.12193. Epub 2014 Aug 28. PubMed PMID: 25132632. 19: Faria-Ramos I, Farinha S, Neves-Maia J, Tavares PR, Miranda IM, Estevinho LM, Pina-Vaz C, Rodrigues AG. Development of cross-resistance by Aspergillus fumigatus to clinical azoles following exposure to prochloraz, an agricultural azole. BMC Microbiol. 2014 Jun 11;14:155. doi: 10.1186/1471-2180-14-155. PubMed PMID: 24920078; PubMed Central PMCID: PMC4061453. 20: Cizelj I, Glavan G, Božič J, Oven I, Mrak V, Narat M. Prochloraz and coumaphos induce different gene expression patterns in three developmental stages of the Carniolan honey bee (Apis mellifera carnica Pollmann). Pestic Biochem Physiol. 2016 Mar;128:68-75. doi: 10.1016/j.pestbp.2015.09.015. Epub 2015 Oct 9. PubMed PMID: 26969442.

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MedKoo CAT#: 528402

CAS#: 160665-99-6