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

MedKoo CAT#: 461288

CAS#: 42874-03-3

Description: Oxyfluorfen is a herbicide of the nitrodiphenyl ether class. It is being used to control annual and perennial broad-leaved weeds and sedges in a variety of field crops.


Chemical Structure

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Oxyfluorfen
CAS# 42874-03-3

Theoretical Analysis

MedKoo Cat#: 461288
Name: Oxyfluorfen
CAS#: 42874-03-3
Chemical Formula: C15H11ClF3NO4
Exact Mass: 361.03
Molecular Weight: 361.701
Elemental Analysis: C, 49.81; H, 3.07; Cl, 9.80; F, 15.76; N, 3.87; O, 17.69

Price and Availability

Size Price Availability Quantity
100mg USD 260
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Synonym: Oxyfluorfen; Boxer; Galigan; Goldate; Koltar; RH-2915; RH 2915; RH2915; Zoomer;

IUPAC/Chemical Name: 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene

InChi Key: OQMBBFQZGJFLBU-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H11ClF3NO4/c1-2-23-14-8-10(4-5-12(14)20(21)22)24-13-6-3-9(7-11(13)16)15(17,18)19/h3-8H,2H2,1H3

SMILES Code: FC(C1=CC=C(OC2=CC=C([N+]([O-])=O)C(OCC)=C2)C(Cl)=C1)(F)F

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:
Biological target: Oxyfluorfen is a protoporphyrinogen oxidase inhibitor.
In vitro activity: TBD
In vivo activity: In this study, zebrafish was used as a model animal to evaluate OXY (oxyfluorfen)-induced liver toxicity. The study found that 0.25, 0.5, and 1 mg/L of OXY affected the early development of zebrafish and severely damaged the lipid and sugar metabolism in the liver of zebrafish larvae. Furthermore, a metabolic function disorder caused liver damage. OXY also caused inflammation by upregulating the inflammatory factors IL-6, IL-8, and TNF-α, and activated the apoptotic pathway to inhibit hepatocyte proliferation, resulting in zebrafish liver toxicity. Reference: Ecotoxicol Environ Saf. 2021 Dec 31;230:113140. https://pubmed.ncbi.nlm.nih.gov/34979306/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 276.47

Preparing Stock Solutions

The following data is based on the product molecular weight 361.70 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
Formulation protocol: Li Z, Guo J, Jia K, Zheng Z, Chen X, Bai Z, Yang Y, Chen B, Yuan W, Chen W, Yang J. Oxyfluorfen induces hepatotoxicity through lipo-sugar accumulation and inflammation in zebrafish (Danio rerio). Ecotoxicol Environ Saf. 2021 Dec 31;230:113140. doi: 10.1016/j.ecoenv.2021.113140. Epub ahead of print. PMID: 34979306.
In vitro protocol: TBD
In vivo protocol: Li Z, Guo J, Jia K, Zheng Z, Chen X, Bai Z, Yang Y, Chen B, Yuan W, Chen W, Yang J. Oxyfluorfen induces hepatotoxicity through lipo-sugar accumulation and inflammation in zebrafish (Danio rerio). Ecotoxicol Environ Saf. 2021 Dec 31;230:113140. doi: 10.1016/j.ecoenv.2021.113140. Epub ahead of print. PMID: 34979306.

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1: Chakraborty SK, Chakraborty S, Bhattacharyya A, Chowdhury A. Photolysis of oxyfluorfen in aqueous methanol. J Environ Sci Health B. 2013;48(11):919-26. doi: 10.1080/03601234.2013.816586. PubMed PMID: 23998303.

2: Janaki P, Sathya Priya R, Chinnusamy C. Field dissipation of oxyfluorfen in onion and its dynamics in soil under Indian tropical conditions. J Environ Sci Health B. 2013;48(11):941-7. doi: 10.1080/03601234.2013.816599. PubMed PMID: 23998306.

3: Kaur N, Bhullar MS. Harvest time residues of pendimethalin and oxyfluorfen in vegetables and soil in sugarcane-based intercropping systems. Environ Monit Assess. 2015 May;187(5):221. doi: 10.1007/s10661-015-4451-4. Epub 2015 Apr 2. PubMed PMID: 25832010.

4: Rodríguez-Morgado B, Gómez I, Parrado J, Tejada M. Behaviour of oxyfluorfen in soils amended with edaphic biostimulants/biofertilizers obtained from sewage sludge and chicken feathers. Effects on soil biological properties. Environ Sci Pollut Res Int. 2014 Sep;21(18):11027-35. doi: 10.1007/s11356-014-3040-3. Epub 2014 May 27. PubMed PMID: 24859703.

5: Mantzos N, Karakitsou A, Hela D, Patakioutas G, Leneti E, Konstantinou I. Persistence of oxyfluorfen in soil, runoff water, sediment and plants of a sunflower cultivation. Sci Total Environ. 2014 Feb 15;472:767-77. doi: 10.1016/j.scitotenv.2013.11.016. Epub 2013 Dec 10. PubMed PMID: 24333999.

6: Gómez I, Rodríguez-Morgado B, Parrado J, García C, Hernández T, Tejada M. Behavior of oxyfluorfen in soils amended with different sources of organic matter. Effects on soil biology. J Hazard Mater. 2014 May 30;273:207-14. doi: 10.1016/j.jhazmat.2014.03.051. Epub 2014 Apr 1. PubMed PMID: 24742665.

7: Phung TH, Jung S. Differential antioxidant defense and detoxification mechanisms in photodynamically stressed rice plants treated with the deregulators of porphyrin biosynthesis, 5-aminolevulinic acid and oxyfluorfen. Biochem Biophys Res Commun. 2015 Apr 3;459(2):346-51. doi: 10.1016/j.bbrc.2015.02.125. Epub 2015 Feb 28. PubMed PMID: 25735982.

8: Pham NT, Kim JG, Jung S. Differential Antioxidant Responses and Perturbed Porphyrin Biosynthesis after Exposure to Oxyfluorfen and Methyl Viologen in Oryza sativa. Int J Mol Sci. 2015 Jul 21;16(7):16529-44. doi: 10.3390/ijms160716529. PubMed PMID: 26197316; PubMed Central PMCID: PMC4519964.

9: Zhao H, Xu J, Dong F, Liu X, Wu Y, Wu X, Zheng Y. Characterization of a novel oxyfluorfen-degrading bacterial strain Chryseobacterium aquifrigidense and its biochemical degradation pathway. Appl Microbiol Biotechnol. 2016 Aug;100(15):6837-6845. doi: 10.1007/s00253-016-7504-x. Epub 2016 Apr 14. PubMed PMID: 27079576.

10: Phung TH, Jung S. Perturbed porphyrin biosynthesis contributes to differential herbicidal symptoms in photodynamically stressed rice (Oryza sativa) treated with 5-aminolevulinic acid and oxyfluorfen. Pestic Biochem Physiol. 2014 Nov;116:103-10. doi: 10.1016/j.pestbp.2014.10.002. Epub 2014 Oct 14. PubMed PMID: 25454526.

11: Saha A, Shabeer T P A, Banerjee K, Hingmire S, Bhaduri D, Jain NK, Utture S. Simultaneous analysis of herbicides pendimethalin, oxyfluorfen, imazethapyr and quizalofop-p-ethyl by LC-MS/MS and safety evaluation of their harvest time residues in peanut (Arachis hypogaea L.). J Food Sci Technol. 2015 Jul;52(7):4001-14. doi: 10.1007/s13197-014-1473-9. Epub 2014 Jul 14. PubMed PMID: 26139867; PubMed Central PMCID: PMC4486543.

12: Stagg NJ, LeBaron MJ, Eisenbrandt DL, Gollapudi BB, Klaunig JE. Assessment of possible carcinogenicity of oxyfluorfen to humans using mode of action analysis of rodent liver effects. Toxicol Sci. 2012 Aug;128(2):334-45. doi: 10.1093/toxsci/kfs157. Epub 2012 Apr 26. PubMed PMID: 22539621.

13: Sondhia S. Persistence and bioaccumulation of oxyfluorfen residues in onion. Environ Monit Assess. 2010 Mar;162(1-4):163-8. doi: 10.1007/s10661-009-0784-1. Epub 2009 Feb 24. PubMed PMID: 19238567.

14: Risco C, Rubí-Juárez H, Rodrigo S, López-Vizcaíno R, Saez C, Cañizares P, Barrera-Díaz C, Navarro V, Rodrigo MA. Removal of oxyfluorfen from spiked soils using electrokinetic soil flushing with the surrounding arrangements of electrodes. Sci Total Environ. 2016 Jul 15;559:94-102. doi: 10.1016/j.scitotenv.2016.03.174. Epub 2016 Apr 5. PubMed PMID: 27058128.

15: Huang B, Li J, Fang W, Liu P, Guo M, Yan D, Wang Q, Cao A. Effect of Soil Fumigation on Degradation of Pendimethalin and Oxyfluorfen in Laboratory and Ginger Field Studies. J Agric Food Chem. 2016 Nov 23;64(46):8710-8721. Epub 2016 Nov 9. PubMed PMID: 27787973.

16: Sheeba, Pratap Singh V, Kumar Srivastava P, Mohan Prasad S. Differential physiological and biochemical responses of two cyanobacteria Nostoc muscorum and Phormidium foveolarum against oxyfluorfen and UV-B radiation. Ecotoxicol Environ Saf. 2011 Oct;74(7):1981-93. doi: 10.1016/j.ecoenv.2011.07.006. Epub 2011 Jul 28. PubMed PMID: 21798597.

17: Yen JH, Sheu WS, Wang YS. Dissipation of the herbicide oxyfluorfen in subtropical soils and its potential to contaminate groundwater. Ecotoxicol Environ Saf. 2003 Feb;54(2):151-6. PubMed PMID: 12550092.

18: Warabi E, Usui K, Tanaka Y, Matsumoto H. Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial protoporphyrinogen oxidase. Pest Manag Sci. 2001 Aug;57(8):743-8. PubMed PMID: 11517729.

19: dos Santos EV, Sáez C, Martínez-Huitle CA, Cañizares P, Rodrigo MA. Removal of oxyfluorfen from ex-situ soil washing fluids using electrolysis with diamond anodes. J Environ Manage. 2016 Apr 15;171:260-6. doi: 10.1016/j.jenvman.2016.01.027. Epub 2016 Feb 1. PubMed PMID: 26846982.

20: Calderon MJ, De Luna E, Gomez JA, Hermosin MC. Herbicide monitoring in soil, runoff waters and sediments in an olive orchard. Sci Total Environ. 2016 Nov 1;569-570:416-422. doi: 10.1016/j.scitotenv.2016.06.126. Epub 2016 Jun 25. PubMed PMID: 27351146.