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Quinoxyfen

PubChem CID
3391107
Structure
Quinoxyfen_small.png
Quinoxyfen_3D_Structure.png
Molecular Formula
Synonyms
  • Quinoxyfen
  • 124495-18-7
  • 5,7-dichloro-4-(4-fluorophenoxy)quinoline
  • Quinoline, 5,7-dichloro-4-(4-fluorophenoxy)-
  • DE 795
Molecular Weight
308.1 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-09-08
  • Modify:
    2025-01-18
Description
Quinoxyfen is a member of the class of quinolines carrying two chloro substituents at positions 5 and 7 together with a 4-fluorophenoxy substituent at position 4. A fungicide used mainly to control powdery mildew in cereals. It has a role as an antifungal agrochemical. It is an aromatic ether, a member of quinolines, an organochlorine compound and a member of monofluorobenzenes.
Quinoxyfen is a fungicide used mainly to control Erysiphe graminis - powdery mildew in cereals. It functions systemically with protective properties, translocates and inhibits appressoria development stopping infections.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Quinoxyfen.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,7-dichloro-4-(4-fluorophenoxy)quinoline
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H8Cl2FNO/c16-9-7-12(17)15-13(8-9)19-6-5-14(15)20-11-3-1-10(18)2-4-11/h1-8H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

WRPIRSINYZBGPK-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC(=CC=C1OC2=C3C(=CC(=CC3=NC=C2)Cl)Cl)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H8Cl2FNO
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

203063-70-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5,7-dichloro-4-(4-fluorophenoxy)quinoline
  • quinoxyfen

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
308.1 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
306.9966974 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
306.9966974 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
22.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
325
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Color / Form

Crystals from heptane
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1389
Off-white solid

3.2.2 Melting Point

105-106 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1389
MP: 100-106 °C /Technical/
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

3.2.3 Flash Point

> 199 °F (>93 °C) (Closed cup) /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf

3.2.4 Solubility

In acetone 116, dichloromethane 589, ethyl acetate 179, methanol 21.5, n-octanol 37.9, toluene 272, hexane 9.64, xylene 200 (all in g/L, 20 °C)
Meister, R.T., Sine, C; Crop Protection Handbook Volume 94. Meister Media Worldwide, Willoughby, OH 2008, p. D 383
In water, 0.128 (pH 5); 0.047 (pH 7); 0.036 (pH 9) (all in g/L, 20 °C)
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
In water, 116 ug/L at 20 °C (pH 6.45)
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

3.2.5 Density

1.56
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

3.2.6 Vapor Pressure

1.50X10-7 mm Hg at 25 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

3.2.7 LogP

log Kow = 4.66 (pH approximately 6.6, 20 °C)
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

3.2.8 Stability / Shelf Life

In dark at 25 °C, stable to hydrolysis at pH 7 and 9; DT50 75 days (pH 4). Degraded more rapidly in light.
MacBean C, ed. Quinoxyfen (124495-18-7). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.

3.2.9 Decomposition

Decomposition products depend upon temperature, air supply and the presence of other materials. Decomposition products can include but are not limited to: chlorine, carbon monoxide, carbon dioxide, and nitrogen oxides. /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf

3.2.10 Ionization Efficiency

Ionization mode
Positive
logIE
3.97
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)

3.2.11 Dissociation Constants

pKa = 3.56, weak base
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

3.2.12 Kovats Retention Index

Semi-standard non-polar
2347 , 2353 , 2326.8

3.3 Chemical Classes

3.3.1 Pesticides

Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Active substance -> EU Pesticides database: Not approved
Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pesticide (Quinoxyfen) -> USDA PDB

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
View All
NIST Number
366494
Library
Main library
Total Peaks
159
m/z Top Peak
237
m/z 2nd Highest
272
m/z 3rd Highest
307
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2 of 4
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NIST Number
378658
Library
Replicate library
Total Peaks
224
m/z Top Peak
237
m/z 2nd Highest
272
m/z 3rd Highest
307
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4.1.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks
308.0039 100
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2 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

308.0038 100

272.0271 17.67

196.9793 8.68

228.9691 8.36

213.982 5.94

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4.1.3 LC-MS

1 of 49
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
12.804 min
Precursor m/z
308.004
Precursor Adduct
[M+H]+
Top 5 Peaks

308.0055 999

310.002 827

309.008 191

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License
CC BY
2 of 49
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
12.818 min
Precursor m/z
308.004
Precursor Adduct
[M+H]+
Top 5 Peaks

308.0045 999

310.0012 838

309.0072 197

272.0264 10

196.9779 5

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License
CC BY

4.1.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
308.004
Instrument
Maxis HD qTOF
Ionization Mode
positive
Top 5 Peaks

308.005341 100

196.979996 37.44

213.982788 25.88

162.010956 17.31

272.028442 11.85

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2 of 3
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MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
308.004
Instrument
Q-Exactive Plus Orbitrap Res 14k
Ionization Mode
positive
Top 5 Peaks

308.004730 100

272.028534 9.02

196.978638 8.16

213.980606 3.92

228.970123 2.92

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6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Fungicide
Pesticide active substances -> Fungicides
Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

7.2 Agrochemical Transformations

Quinoxyfen has known environmental transformation products that include 3-hydroxy-quinoxyfen.
S78 | SLUPESTTPS | Pesticides and TPs from SLU, Sweden | DOI:10.5281/zenodo.4687924
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

7.3 EU Pesticides Data

Active Substance
quinoxyfen
Status
Not approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/09/2004 Expiration: 27/12/2018
Legislation
04/60/EC, Reg. (EU) 2016/2016, Reg. (EU) 2018/1914, Reg. (EU) No 540/2011, Reg.(EU)2018/524
ADI
0.2 mg/kg bw/day [Directive 2004/60/EC]
AOEL
0.14 mg/kg bw/day [Directive 2004/60/EC]

7.4 USDA Pesticide Data Program

8 Pharmacology and Biochemistry

8.1 Absorption, Distribution and Excretion

The jugular-vein cannulated rats (five males and five females per group) were killed at 48 hr after dosing. The bile-duct cannulated rats (three males per group) were killed at 24 hr after dosing. Blood samples were taken from the jugular cannula at 0.25, 0.5, 0.75, 1, 1.5, 3, 6, 12, 24 and 48 hr. Urine, feces and bile were collected regularly throughout the study. Peak plasma radioactivity (Cmax) was detected at approximately 0.5 hr (2-3 ug equiv./g) at 10 mg/kg bw and approximately 1.5 hr (80-90 mg equiv./g) at 500 mg/kg bw. ... There were no significant differences between the repeat-dose and single-dose groups. The elimination of radioactivity from blood followed a similar pattern. The area-under-the-curve (AUC) of the plasma versus time graph for the elimination of radiolabel in plasma (0-48 hr) was 22.3, 27.3 and 922 ug equiv. hr/g in males and 30.4, 29.6 and 963 ug equiv. hr/g in females after treatments with a single radiolabelled dose, a single radiolabelled dose after repeated dosing and 500 mg/kg bw (14)C-quinoxyfen respectively.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.370 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
By 24 hr after dosing, 68-85% of the administered radioactivity had been recovered in the feces and urine, indicating rapid elimination from the body. After 48 hr, 90-96% of the administered (14)C-quinoline ring-labelled quinoxyfen was recovered in the urine, feces, cage wash and tissues. The feces represented the major route of elimination as 68-78% of the administered dose was eliminated via this route in 48 hr, while 13-20% was eliminated in the urine. Urinary half-lives ranged from 6 to 10 hr. The tissues and carcass accounted for 1-7%, contents of the gastrointestinal tract for < 3% and final cage wash for < 1% of the administered dose. There were no sex differences in the distribution of radiolabel. Repeated administration of quinoxyfen did not affect the distribution of the radio-labelled dose.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.370 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
The distribution of radiolabel in organs and tissues (percentage of administered dose/g tissue) 48 hr after treatment with a single dose of quinoline ring-labelled quinoxyfen at 10 mg/kg bw showed that the highest amounts of radiolabel were present in perirenal fat (0.12 in males and 0.35 females) > ovaries (0.07) > liver (0.027 in males and 0.045 in females) and kidneys (0.014 in males and 0.033 in females). Significant levels were found in the skin. Similar amounts were obtained after repeated dosing and a similar pattern after the higher dose of 500 mg/kg bw. There were no data on tissue levels at times approximating to the plasma Cmax.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.371 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
Comparison of the relative concentrations in bile and urine of intact and bile-duct cannulated rats indicated that enterohepatic recirculation is extensive with quinoxyfen at a dose of 10 mg/kg bw. In bile-duct cannulated rats, there was a marked difference in the amount of radiolabel in the feces of rats at 10 mg/kg bw (14.3%) compared with those at 500 mg/kg bw (57.3%) and in the amount of radiolabel in the bile of rats at 10 mg/kg bw (54.4%) compared with those at 500 mg/kg bw (21.4%). These findings indicated that absorption of quinoxyfen at a dose of 500 mg/kg bw dose was saturated.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.371 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
For more Absorption, Distribution and Excretion (Complete) data for Quinoxyfen (7 total), please visit the HSDB record page.

8.2 Metabolism / Metabolites

Groups of 5 Fischer 344 rats/sex were given a single 10 or 500 mg/kg oral dose of quinoline ring-labeled (14)C- quinoxyfen (XDE-795, >99% radiochemically pure, specific active 28.5 mCi/mmole), or 14 daily oral doses of 10 mg/kg of non-radiolabelled quinoxyfen (XDE-795, 99% pure) followed by a single 10 mg/kg oral dose of (14)C- quinoxyfen. Additional groups of 3 male bile duct cannulated rats received a single dose of 10 or 500 mg/kg quinoline ring-labelled (14)C- quinoxyfen and were sacrificed 24 hrs later. One rat/sex/group received 10 mg/kg of either phenyl ring (98.5% radiochemically pure, specific active 27.8 mCi/mmole) or quinoline ring-labelled (14)C- quinoxyfen for metabolite analysis. ... Major metabolites identified in the urine were derived from cleavage of the diaryl-ether linkage quinoxyfen resulting in the formation of acid-labile conjugates of 4-fluorophenol (4-FP) and 5, 7-dichloro-4-hydroxyquinoline (DCHQ), and lesser quantities of free DCHQ and 4-FP. Glucuronide and/or sulfate conjugates of two isomers of fluorophenyl ring-hydroxy- quinoxyfen were detected in the bile. Parent quinoxyfen and free forms of the same two isomers of fluorophenyl ring-hydroxy- quinoxyfen as seen in the bile were detected in feces. No substantive differences in the metabolism and disposition of quinoxyfen between sexes or single and repeated administration.
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Quinoxyfen (124495-18-7) p.9 (November 9, 1993). Available from, as of May 25, 2011: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm
HPLC separation of pooled 0-12 hr urine samples from the preliminary study in rats given phenyl-ring-labelled (14)C-quinoxyfen produced eight peaks that were designated P1-P7 and P10. Peak P5 was the major urinary fraction in the unhydrolyzed urine sample (80% and 77.4% in the male and female respectively) followed by P3 (7.9% and 9.5%), P1 (4.2% and 4.7%) and P6 (3.1% and 3.0%). The remaining peaks contained less than 3% of the urinary radiolabel. Acid hydrolysis of the urine produced a significant change in the HPLC profile. The major fraction in unhydrolyzed urine was reduced to only 2.4% of the urine fraction; instead, P8 (not detectable in the unhydrolyzed sample) was the major fraction (73.6%). This suggested that P5 might be a conjugate of P8. The P8 fraction was found to co-elute with the standard for 4-fluorophenol. The remaining minor peaks after acid hydrolysis were P3 (11.7%), P9 (7.1%) and P1 (5.2%), but these metabolites were not identified. The standards used were 4-fluorophenol, 2-hydroxy-quinoxyfen and parent quinoxyfen. Parent quinoxyfen and 2-hydroxy-quinoxyfen retention times did not correspond to that of any of the HPLC urinary fractions. Fecal metabolites from phenyl-(14)C quinoxyfen showed a similar pattern to those from quinoline-(14)C quinoxyfen.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.373 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
HPLC separation of pooled urine samples from groups receiving quinoline-(14)C quinoxyfen ... before and after acid hydrolysis produced up to 16 radiolabelled peaks that were designated Q1-Q16. In male rats receiving a single dose at 10 mg/kg bw, eight peaks were identified in unhydrolyzed urine: Q3, Q4, Q7, Q8, Q9, Q11, Q12 and Q13. In females rats receiving a single dose at 10 mg/kg bw, four additional peaks were detected: Q2, Q5, Q10 and Q15 (repeated-dose only). For the males and females at 500 mg/kg bw, the peaks in the radiochromatogram of pooled 0-12 hr urine samples were Q7, Q8, Q9, Q10 (female only), Q11, Q12 and Q13. The major peaks were Q11 (13-33%), Q8 (13-24%), Q9 (9-24%), Q12 (10-18%), Q13 (6-15%), Q7 (4-11%) and Q4 (< 13%). The only clearly identified urinary metabolite was 5,7 dichloro-4-hydroxyquinoline (DCHQ), which was found to co-elute with peak Q13. Acid hydrolysis resulted in a two- to four-times increase in Q13 (24-65%). In the males rats receiving a single dose at 10 mg/kg bw, increases were observed in peaks Q3, Q6 and Q14, while peaks Q1 and Q2 were increased after acid hydrolysis. In rats receiving a single dose at 500 mg/kg bw, peak Q14 was increased in males. Concomitantly, peaks Q4, Q5, Q7, Q8 and Q10 were observed to disappear from the respective radiochromatograms, while Q3 and Q9 were markedly reduced. Enzyme hydrolysis did not affect the metabolite profile.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.372 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
HPLC separation of bile samples (taken at various time-points, 0-24 hr) from male rats receiving quinoline ring-labelled quinoxyfen at 10 mg/kg bw or 500 mg/kg bw produced six peaks (B2-B7). Peaks B6 and B7 constituted 20-66% and 26-59% of biliary excretion at various time-points. For the 10 mg/kg bw rats, the amount of radiolabel in the peaks at various time-points were B2 6-15%; B5 4-15%; B3 and B4 < 5%. Only peaks B6 and B7 were detected in the samples from rats at 500 mg/kg bw, but this was attributed to the higher detection limits required by the investigating laboratory. Additional peaks B1, B8, B9 and B10 were detected after enzyme hydrolysis. Peak B7 was noted to disappear with the appearance of peak B10 (approximately 25%) suggesting that B7 is the glucuronide or sulfatase of B10. Acid hydrolysis of the bile samples from rats at 10 or 500 mg/kg bw resulted in an increase in B6 by 20% of the biliary radioactivity compared with the control. Peaks B1, B8 and B9 appeared in the sample from rats at 10 mg/kg bw, but were not detected at 500 mg/kg bw. B10 eluted with quinoxyfen, but MS showed that the key ions were 16 mass units greater than the corresponding fragment ions from quinoxyfen. It was concluded that two metabolites associated with peak B10 were isomers of fluorophenyl-ring hydroxylated quinoxyfen.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.373 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
For more Metabolism/Metabolites (Complete) data for Quinoxyfen (7 total), please visit the HSDB record page.

8.3 Biological Half-Life

The jugular-vein cannulated rats (five males and five females per group) were killed at 48 hr after dosing. The bile-duct cannulated rats (three males per group) were killed at 24 hr after dosing. Blood samples were taken from the jugular cannula at 0.25, 0.5, 0.75, 1, 1.5, 3, 6, 12, 24 and 48 hr. Urine, feces and bile were collected regularly throughout the study. ... The elimination of plasma radioactivity followed a biphasic pattern with half-lives for the rapid and slow phases for the dose at 10 mg/kg bw of < 1 hr and 15-19 hr respectively, and 2-3 hr and 18-22 hr for the dose at 500 mg/kg bw. There were no significant differences between the repeat-dose and single-dose groups. ...
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.370 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html

8.4 Transformations

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
For quinoxyfen (USEPA/OPP Pesticide Code: 055459) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
National Pesticide Information Retrieval System's USEPA/OPP Chemical Ingredients Database on Quinoxyfen (124495-18-7). Available from, as of May 23, 2011: https://npirspublic.ceris.purdue.edu/ppis/
Agricultural fungicide
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1389
This is a man-made compound that is used as a pesticide.

9.1.1 Use Classification

Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

9.2 Methods of Manufacturing

Quinoxyfen is produced by reaction of 4,5,7-trichloroquinoline with p-fluorophenol in the presence of 4-dimethylaminopyridine as catalyst in refluxing xylene.
Muller F et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2011). New York, NY: John Wiley & Sons; Fungicides, Agricultural. Online Posting Date: January 15, 2010

9.3 Formulations / Preparations

Soluble concentrate
Mester, R.T.,Sine, C. (eds.) Crop Protection Handbook Volume 97. Meisterpro. Willoughby,OH. 2011, p. 605
Quinoxyfen Technical (Dow Agrosciences, LLC) Quinoxyfen 99.1%
Purdue University; National Pesticide Information Retrieval System, Quinoxyfen PC Code 55459. Available from, as of June 7, 2011: https://npirspublic.ceris.purdue.edu/ppis/
Quinoxyfen Manufacturing Use Concentrate (Dow Agrosciences, LLC) Quinoxyfen 53.5%
Purdue University; National Pesticide Information Retrieval System, Quinoxyfen PC Code 55459. Available from, as of June 7, 2011: https://npirspublic.ceris.purdue.edu/ppis/
Quintec (Dow Agrosciences, LLC) Quinoxyfen 22.58%
Purdue University; National Pesticide Information Retrieval System, Quinoxyfen PC Code 55459. Available from, as of June 7, 2011: https://npirspublic.ceris.purdue.edu/ppis/

9.4 General Manufacturing Information

The WHO Recommended Classification of Pesticides by Hazard identifies quinoxyfen as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.
WHO (2010) The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2009, International Programme on Chemical Safety, p.45

10 Identification

10.1 Analytic Laboratory Methods

Adequate enforcement methodology (gas chromatography with mass-selective detection (GC-MSD)) is available to enforce the tolerance expression.
74 FR 14742 (4/1/2009)
Residue analysis in plant, animal and soil matrices by GC with mass selective detection. Analysis in drinking water by HPLC with UV detection.
MacBean C, ed. Quinoxyfen (124495-18-7). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 3
View All
Pictogram(s)
Irritant
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 212 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Skin Sens. 1 (100%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

Skin sensitisation - category 1

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 1

11.2 Fire Fighting

11.2.1 Fire Fighting Procedures

Wear positive-pressure self-contained breathing apparatus (SCBA) and protective fire fighting clothing (includes fire fighting helmet, coat, trousers, boots, and gloves). If protective equipment is not available or not used, fight fire from a protective location or safe distance. /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf
Keep people away. Isolate fire and deny unnecessary entry. Consider feasibility of a controlled burn to minimize environment damage. foam fire extinguishing system is preferred because uncontrolled water can spread possible contamination. Burning liquids may be moved by flushing with water to protect personnel and minimize property damage. /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf
Extinguishing media: Water fog or fine spray, carbon dioxide, dry chemical, or foam. General purpose synthetic foams (including AFFF type) or protein foams are preferred if available. Alcohol resistant foams (ATC type) may function. /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf

11.3 Accidental Release Measures

11.3.1 Cleanup Methods

Prevent from entering into soil, ditches, sewers, waterways, and/or groundwater.
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf
Large spills: Dike area to contain spill.
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf
Do not contaminate water when cleaning equipment or disposing of equipment washwaters.
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf

11.3.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Wastes resulting from the sue of this product must be disposed of on site or at an approved waste disposal facility.
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
Do not dump into any sewers, on the ground, or into any body of water. For unused and uncontaminated product, the preferred options include sending to a licensed, permitted: reclaimer or incinerator or other thermal destruction device. If wastes and/or containers cannot be disposed of according to the product label directions, disposal of this material must be in accordance with your local or area regulatory authorities.
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

11.3.3 Preventive Measures

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Quintec Fungicide/
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
This product is toxic to fish and aquatic invertebrates. Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the mean high water mark. Do not apply when weather conditions favor runoff or drift from the target areas. /Quintec Fungicide/
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). If not such instructions for wasables exist, use detergent and hot water. Keep and was PPE separately from other laundry. /Quintec Fungicide/
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove contaminated clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Remove personal protective equipment (PPE) immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Quintec Fungicide/
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
For more Preventive Measures (Complete) data for Quinoxyfen (7 total), please visit the HSDB record page.

11.4 Handling and Storage

11.4.1 Storage Conditions

Avoid freezing. Store in original container only.
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
Keep out of reach of children. Store in a dry place, 0-30 °C. use only with adequate ventilation. Protect from heat. Store in original container. /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf

11.5 Exposure Control and Personal Protection

11.5.1 Allowable Tolerances

Tolerances are established for residues of the fungicide quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline in or on the following raw agricultural commodities:
Commodity
Artichoke, globe
Parts per million
1.4
Commodity
Fruit, stone, group 12
Parts per million
0.70
Commodity
Hop, dried cones
Parts per million
3.0
Commodity
Gourd, edible
Parts per million
0.20
Commodity
Grape
Parts per million
0.60
Commodity
Lettuce, head
Parts per million
7.0
Commodity
Lettuce, leaf
Parts per million
19
Commodity
Melon, subgroup 9A
Parts per million
0.08
Commodity
Pepper, bell
Parts per million
0.35
Commodity
Pepper, nonbell
Parts per million
1.7
Commodity
Pumpkin
Parts per million
0.20
Commodity
Squash, winter
Parts per million
0.20
Commodity
Strawberry
Parts per million
0.90
40 CFR 18.0588 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of May 2, 2011: https://www.ecfr.gov

11.5.2 Personal Protective Equipment (PPE)

Applicators and other handlers must wear: Long-sleeved shirt and long pants, chemical-resistant gloves, shoes plus socks. /Quintec Fungicide/
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf
... Restricted-entry interval (REI) of 12 hours. Personal protective equipment (PPE) required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water is: Coveralls, Chemical resistant gloves made of any waterproof material. Shoes plus socks. /Quintec Fungicide/
Dow AgroSciences LLC; Product Label for Quintec Fungicide (11/30/2009). Available from, as of June 20, 2011: https://www.cdms.net/ldat/ld6ck000.pdf

11.6 Regulatory Information

Status Regulation (EC)
04/60/EC, Reg. (EU) 2016/2016, Reg. (EU) 2018/1914, Reg. (EU) No 540/2011, Reg.(EU)2018/524
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Quinoxyfen: Does not have an individual approval but may be used under an appropriate group standard

11.6.1 FIFRA Requirements

Tolerances are established for residues of the fungicide quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline in or on the following raw agricultural commodities:
Commodity
Artichoke, globe
Commodity
Fruit, stone, group 12
Commodity
Hop, dried cones
Commodity
Gourd, edible
Commodity
Grape
Commodity
Lettuce, head
Commodity
Lettuce, leaf
Commodity
Melon, subgroup 9A
Commodity
Pepper, bell
Commodity
Pepper, nonbell
Commodity
Pumpkin
Commodity
Squash, winter
Commodity
Strawberry
40 CFR 18.0588 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of May 2, 2011: https://www.ecfr.gov
Reregistration Eligibility Decision (RED) Scheduled for 2014
US EPA; Reregistration Review: Summary of Planned Schedule for Opening Registration Review Dockets by Fiscal Year 2011 to 2014. April 1, 2011. Washington, DC; USEPA, Off Pest Prog. Available from, as of June 23, 2011: https://www.epa.gov/oppsrrd1/registration_review/2011-14-schedule-summary.pdf

11.7 Other Safety Information

11.7.1 Toxic Combustion Products

During a fire, smoke may contain the original material in addition to combustion products of varying composition which may be toxic and/or irritating. Combustion products may include and are not limited to: nitrogen oxides, fluorine, chlorine, carbon monoxide, and carbon dioxide. /Quintec Fungicide/
Dow AgroSciences LLC; MSDS, Quintec Fungicide (MSDS Number: 007615; Effective Date: 3/24/2008). Available from, as of June 20, 2011: https://www.cdms.net/ldat/mp6CK023.pdf

12 Toxicity

12.1 Toxicological Information

12.1.1 RAIS Toxicity Values

Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.2
Oral Chronic Reference Dose Reference
OPP

12.1.2 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Chronic or One Day PAD (RfD) [mg/kg/day]
0.2
Chronic or One Day HHBPs [ppb]
1000
Chronic HHBP Sensitive Lifestage/Population
General Population

12.1.3 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

12.1.4 Acute Effects

12.1.5 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

12.1.6 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ A formulation chemist ... was shown to be sensitized to aqueous solutions containing 10% or more quinoxyfen. No other cases had been found after checking all employees who have worked with the material. In addition, 20 control individuals were patch-tested specifically with quinoxyfen and this produced an entirely negative reaction. The data from the formulation laboratory were suggested by the applicant to indicate that there is a small possibility for idiosyncratic skin sensitization. Since the formulation chemist may have been sufficiently exposed to be sensitized compared with other workers and given the additional evidence from animal experiments, this finding is consistent with quinoxyfen being a skin sensitizer.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.393 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
/CASE REPORTS/ ... Two operators and a supervisor were exposed to quinoxyfen while decanting a returned batch of a 50% w/w soluble concentrate formulation. All three developed rashes of the wrist/forearm. The supervisor and one operator were tested for sensitization to quinoxyfen, with positive results. The other operator had left the company before the follow-up testing was performed.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.394 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
/SURVEILLANCE/ None of 28 individuals in a health surveillance program reported or presented for health concerns related to quinoxyfen between June 1992 and March 1995. Audits of clinical records of all individuals involved in the investigations were performed and no health-related problems relating to quinoxyfen were noted.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.394 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html

12.1.7 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Quinoxyfen was not irritating to skin, but was slightly irritating to rabbits' eyes. A study of skin sensitization by the Buehler method gave negative results, but a second study using the Magnusson & Kligman maximization method produced clear evidence of skin sensitization.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.375 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of four male and four female beagle dogs were fed diets containing quinoxyfen (purity: 98.7%) at nominal doses of 0 (control) 10, 50 or 100 mg/kg bw per day for 90 days. The parameters assessed were in-life observations, body weight and body-weight gain, feed consumption, hematology, clinical chemistry, urine analysis, organ weights, gross and histopathological evaluations. The achieved mean daily compound intakes were 10, 50 and 100 mg/kg bw per day in males and 10, 50 and 101 mg/kg bw per day in females at nominal doses of 10, 50 and 100 mg/kg bw per day. At the start of treatment, body weights ranged from 8.19 to 10.82 kg in male dogs and 7.48-9.30 kg in female dogs. No mortalities occurred during the study period. There were no adverse effects on animal behavior. Ophthalmological examinations at the beginning and on day 87 of the study did not reveal any treatment-related ocular defects. A slight transient reduction in food consumption was observed in the highest dose males but the animals adapted to the initial unpalatability. However, it was noted that females at the highest dose consumed more feed than did controls. Body-weight gain was not affected. Clinical chemistry, urine analysis and hematology parameters did not show any biologically significant treatment-related changes. The terminal body weights and organ weights did not show any significant treatment related intergroup differences; increased relative liver weights in the groups at 50 mg/kg bw per day were not reproduced at 100 mg/kg bw per day. Gross examination at necropsy did not reveal any significant treatment-related changes. Histopathological examination revealed only a single incidence of slight and midzonal centrilobular hepatocellular hypertrophy, with no associated clinical chemistry or additional histopathology findings, which indicated that the dose of 100 mg/kg bw per day may represent a threshold dose for histopathological effects on the liver. The NOAEL was 100 mg/kg bw per day. The single occurrence of hepatocellular hypertrophy, with no associated clinical chemistry or other histopathological findings, was not considered to be adverse.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.380 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a GLP compliant study, groups of 10 male and 10 female Fischer 344 rats were given diets containing quinoxyfen (purity, 98.7%) at a dose of 0 (control), 10, 100 or 250 mg/kg bw per day for 13 weeks. All animals were killed at the end of the treatment period and underwent necropsy. Additional satellite groups of 10 male and 10 female rats were fed doses of 0 or 250 mg/kg bw per day for 13 weeks and then kept on a quinoxyfen-free diet for an additional 4 weeks in order to investigate recovery from any effects. The achieved daily intakes of quinoxyfen were 10, 102 and 253 mg/kg bw per day) in males and 10, 100 and 249 mg/kg bw per day in females at nominal doses of 10, 100 and 250 mg/kg bw per day, respectively. The parameters investigated included in-life observations, a battery of functional tests, hematology, clinical chemistry, urine analysis, organ weights, gross and histopathological examinations of organs and tissues. Histopathology was limited to the adrenal glands, kidneys, liver, lungs, testes and gross lesions for the groups at 10 and 100 mg/kg bw per day. At the start of the study, the body weights of male rats ranged from 150.1 to 185.8 g (group means, 170.6-171.4 g) and that of female rats 120.5-141.4 g (group means, 131.8-134.3 g). No mortalities occurred during the study period. There were no signs of treatment-related effects during regular observations and during the battery of functional tests on day 83. The changes in body-weight gain in males (overall body-weight gain was only 3-6% lower than that of controls at doses of >/= 100 mg/kg bw per day) were minimal and not of biological significance. However, reductions in body-weight gain were observed in females at 100 mg/kg bw per day (very slightly but statistically significantly lower than concurrent controls from day 63 to termination) and at 250 mg/kg bw per day (from day 14 onwards and including the recovery period). Terminal body weights in females were reduced by 14% and 16% at 100 and 250 mg/kg bw per day, respectively. There were no clear biologically significant treatment-related differences in the hematology of treated and control animals; reductions in concentrations of hemoglobin (3%) in males at the highest dose achieved statistical significance. Clinical chemistry showed statistically significant reductions in alkaline phosphatase (ALP), alanine aminotransferase (ALT) and aspartate aminotransferase (AST) in males (11.4%, 19.3% and 19.6% respectively) at 250 mg/kg bw per day compared with controls, but the corresponding changes in females at the same dose (9.3%, 27.8% and 12.8% respectively) were not statistically significant. These observations were considered to be of no biological significance. Increases in blood albumin, total protein and potassium concentrations were observed at doses of 100 mg/kg bw per day in males and at 250 mg/kg bw per day in females compared with controls. There was incomplete recovery from the clinical chemistry changes at the end of the recovery period. Urine analysis did not reveal any treatment-related changes. Gross examination at necropsy did not reveal any treatment-related abnormalities. Organ weights showed a significant increase in the mean absolute and relative liver weights at doses of >/= 100 mg/kg bw per day in males (17-33%) and females (9-29%) compared with controls. A slight increase in absolute and relative kidney weights in males and in relative kidney weight in females only was observed at 250 mg/kg bw per day compared with controls. At the end of the recovery period, the absolute and relative liver weights were slightly increased in males at 250 mg/kg bw per day compared with controls. Histopathology at 13 weeks revealed slight centrilobular and midzonal hepatocellular hypertrophy with increased basophilia at doses of > 100 mg/kg bw per day in the 90-day group. Panlobular hepatocellular hypertrophy with increased basophilia and very slight individual cell hepatocellular necrosis were observed in males and females at the highest dose only. At the end of the 4-week recovery period, histopathology of the liver showed that 8 out of 10 male rats in the group at the highest dose exhibited very slight centrilobular hepatocellular hypertrophy with increased basophilia, indicating a reduction of the effects on the liver. The NOAEL was 10 mg/kg bw per day on the basis of reduction in body-weight gain, alterations in clinical chemistry, increase in absolute and relative liver weight and changes in the histopathology of the liver.
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.377 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Quinoxyfen (XDE-795, purity = 97.4%), suspended in aqueous 0.5% methylcellulose, was applied to the clipped skin of 10 Fischer 344 rats per sex per dose at dose levels of 0 (vehicle only), 10, 100, or 1000 mg/kg/day for 6 hrs per day, 5 days a week for 4 weeks using an occlusive wrap. No animals died. No treatment-related signs of systemic toxicity or local skin irritation were observed. No treatment-related body weight, organ weight, hematological, or serum chemistry effects were observed. Macroscopic and microscopic examinations revealed no treatment-related abnormalities. ... NOEL (M/F, systemic and skin) = 1000 mg/kg/day (based on no effects at the highest dose tested). ...
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Quinoxyfen (124495-18-7) p.8 (November 9, 1993). Available from, as of May 25, 2011: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm
For more Non-Human Toxicity Excerpts (Complete) data for Quinoxyfen (23 total), please visit the HSDB record page.

12.1.8 Non-Human Toxicity Values

LD50 Rabbit dermal >2000 mg/kg
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.375 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
LC50 Rat inhalation > 3.38 mg/L (mass median aerodynamic diameter 3.6 um) /Duration not specified/
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.375 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html
LD50 Rat oral >5000 mg/kg
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.375 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html

12.2 Ecological Information

12.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

12.2.2 Ecotoxicity Values

EC50; Species: Selenastrum capricornutum (Green Algae); Concentration: >0.058 mg/L for 72 hr; Effect: Biomass /Conditions of bioassay not specified in source examined/
MacBean C, ed. Quinoxyfen (124495-18-7). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
EC50; Species: Daphnia magna (Water Flea); Concentration: >0.08 mg/L for 48 hr /Conditions of bioassay not specified in source examined/
MacBean C, ed. Quinoxyfen (124495-18-7). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
LC50; Species: Oncorhynchus mykiss (Rainbow Trout); Concentration: 0.27 mg/L for 96 hr /Conditions of bioassay not specified in source examined/
MacBean C, ed. Quinoxyfen (124495-18-7). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
LC50; Species: Lepomis macrochirus (Bluegill); Concentration: >0.28 mg/L for 96 hr /Conditions of bioassay not specified in source examined/
MacBean C, ed. Quinoxyfen (124495-18-7). In: The e-Pesticide Manual, 15th Edition, Version 5.0.1 (2010). Surrey UK, British Crop Protection Council.
For more Ecotoxicity Values (Complete) data for Quinoxyfen (7 total), please visit the HSDB record page.

12.2.3 Environmental Fate / Exposure Summary

Quinoxyfen's production may result in its release to the environment through various waste streams; its use as an agricultural fungicide will result in its direct release to the environment. If released to air, a vapor pressure of 1.5X10-7 mm Hg at 25 °C indicates quinoxyfen will exist in both the vapor and particulate phases. Vapor-phase quinoxyfen will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 1 day. Particulate-phase quinoxyfen will be removed from the atmosphere by wet or dry deposition. Quinoxyfen contains chromophores that absorb at wavelengths >290 nm, and therefore may be susceptible to direct photolysis by sunlight. If released to soil, quinoxyfen is expected to have slight mobility based upon an estimated Koc of 3600. Volatilization from moist soil surfaces is not expected to be an important environmental fate process based upon an estimated Henry's Law constant of 9.6X10-9 atm-cu m/mole. Quinoxyfen may not volatilize from dry soil surfaces based upon its vapor pressure. Quinoxyfen biodegradation half-lives in soils have been reported to range from 106-508 days, suggesting that biodegradation is not an important environmental fate process in soil. If released into water, quinoxyfen is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Using a water/sediment inoculum, half-lives of 35 to 150 days have been reported, suggesting that biodegradation is an environmental fate process in water. Volatilization from water surfaces is not expected to be an important environmental fate process based upon this compound's estimated Henry's Law constant. The estimated volatilization half-life from a model pond is 85 years if adsorption is considered. An estimated BCF of 500 suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism. Quinoxyfen is stable to hydrolysis at pH 7 and pH 9. Photolysis in water is an important environmental fate process with half-lives of 1.7 hours (June) and 22.8 hours (December) reported. Occupational exposure to quinoxyfen may occur through inhalation and dermal contact with this compound at workplaces where quinoxyfen is produced or used. (SRC)

12.2.4 Artificial Pollution Sources

Quinoxyfen's production may result in its release to the environment through various waste streams; its use as an agricultural fungicide(1) will result in its direct release to the environment(SRC).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

12.2.5 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3600(SRC), determined from a log Kow of 4.66(2) and a regression-derived equation(3), indicates that quinoxyfen is expected to have slight mobility in soil(SRC). Volatilization of quinoxyfen from moist soil surfaces is expected to be a minor environmental fate process(SRC) given an estimated Henry's Law constant of 9.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Quinoxyfen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-7 mm Hg at 25 °C(2). Quinoxyfen biodegradation half-lives in soils have been reported to range from 106-508 days(2), suggesting that biodegradation is not an important environmental fate process(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jun 23, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3600(SRC), determined from a log Kow of 4.66(2) and a regression-derived equation(3), indicates that quinoxyfen is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 9.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 550(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Photolysis in water is an important environmental fate process with half-lives of 1.7 hours (June) and 22.8 hours (December) reported(2). Using a water/sediment inoculum, half-lives of 35 to 150 days have been reported(2), suggesting that biodegradation is an environmental fate process in water(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jun 23, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(5) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(6) Franke C et al; Chemosphere 29: 1501-14 (1994)
(7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), quinoxyfen, which has a vapor pressure of 1.50X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase quinoxyfen is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1 day(SRC), calculated from its rate constant of 5.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase quinoxyfen may be removed from the air by wet or dry deposition(SRC). Quinoxyfen contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

12.2.6 Environmental Biodegradation

AEROBIC: Quinoxyfen biodegradation half-lives in soils have been reported to range from 106-508 days using 7 unspecified soils incubated at 20 to 25 °C(1).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
ANAEROBIC: Quinoxyfen biodegradation half-life in soil has been reported as 289 days at 20 °C. Using a water/sediment inoculum maintained in the dark, half-lives of 35 to 150 days have been reported, yielding 2-oxoquinoxyfen(1).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

12.2.7 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of quinoxyfen with photochemically-produced hydroxyl radicals has been estimated as 5.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Quinoxyfen is stable to hydrolysis at pH 7 and pH 9; a hydrolysis half-life of 75 days has been reported at pH 4(2). Quinoxyfen contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC). Photolysis on soil is slow with a half-life in the field of greater than 1 year reported(2). Photolysis in water is an important environmental fate process as indicated by half-lives of 1.7 hours (June) and 22.8 hours (December)(2).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

12.2.8 Environmental Bioconcentration

An estimated BCF of 550 was calculated in fish for quinoxyfen(SRC), using a log Kow of 4.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jun 23, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.9 Soil Adsorption / Mobility

The Koc of quinoxyfen is estimated as 3600(SRC), using a log Kow of 4.66(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that quinoxyfen is expected to have slight mobility in soil.
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Jun 23, 2011: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Swann RL et al; Res Rev 85: 17-28 (1983)

12.2.10 Volatilization from Water / Soil

The Henry's Law constant for quinoxyfen is estimated as 9.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that quinoxyfen is expected to be essentially nonvolatile from water and moist soil surfaces(2). Quinoxyfen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-7 mm Hg(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Quinoxyfen (124495-18-7) (2008-2010)

12.2.11 Milk Concentrations

EXPERIMENTAL: (14)C-quinoxyfen, labeled either in the phenoxy ring or the quinoline ring, was investigated in lactating dairy goats (n = 5; 51-60 kg bw). Two goats were orally dosed with phenoxy (14)C-quinoxyfen (purity: > 98%), twice per day for five consecutive days, at a concentration of 10.7 mg/kg feed. Similarly, two goats were treated with quinoline (14)C-quinoxyfen, twice per day for five consecutive days, at a concentration of 11.7 mg/kg feed. The remaining goat was used as the untreated control animal. Urine and feces were collected at intervals of 24 hrs until sacrifice. Milk samples were collected before the first treatment with quinoxyfen, and then twice daily throughout the study period until animals were sacrificed. ... The major component present in fat was quinoxyfen (approximately 90% TRR /total radio-labeled residue/), while milk contained quinoxyfen (approximately 40% TRR) and some very polar material. ...
WHO/FAO; Joint Meeting on Pesticide Residues Evaluation for Quinoxyfen (124495-18-7) p.373 (2006). Available from, as of June 13, 2011: https://www.inchem.org/pages/jmpr.html

12.2.12 Probable Routes of Human Exposure

Occupational exposure to quinoxyfen may occur through inhalation and dermal contact with this compound at workplaces where quinoxyfen is produced or used. (SRC)

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Chemical Co-Occurrences in Literature

14.6 Chemical-Gene Co-Occurrences in Literature

14.7 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 KEGG: Pesticides

18.4 ChemIDplus

18.5 UN GHS Classification

18.6 EPA CPDat Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 EPA DSSTox Classification

18.9 PFAS and Fluorinated Organic Compounds in PubChem

18.10 EPA Substance Registry Services Tree

18.11 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. EPA Safe Drinking Water Act (SDWA)
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  9. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  10. ChEBI
  11. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  12. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  13. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  14. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  15. EPA Chemical and Products Database (CPDat)
  16. EPA Pesticide Ecotoxicity Database
  17. EU Pesticides Database
  18. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    quinoxyfen
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  19. USDA Pesticide Data Program
  20. Hazardous Chemical Information System (HCIS), Safe Work Australia
  21. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    quinoxyfen (ISO); 5,7-dichloro-4-(4-fluorophenoxy)quinoline
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  22. Human Metabolome Database (HMDB)
    LICENSE
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    http://www.hmdb.ca/citing
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  25. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    quinoxyfen
  26. MassBank Europe
  27. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  28. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  29. SpectraBase
  30. Springer Nature
  31. Thieme Chemistry
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
  32. Wikidata
  33. PubChem
  34. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  35. GHS Classification (UNECE)
  36. EPA Substance Registry Services
  37. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  38. PATENTSCOPE (WIPO)
CONTENTS