p-[4,5-dihydro-4-[[2-methoxy-5-methyl-4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-3-methyl-5-oxo-1H-pyrazol-1-yl]benzenesulphonic acid

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: screening tests

Type of information:

(Q)SAR

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification

Justification for type of information:

The supporting QMRF report has been attached

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

Principles of method if other than guideline:

The prediction was done by using OECD QSAR tool box v3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: p-[4,5-dihydro-4-[[2-methoxy-5-methyl-4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-3-methyl-5-oxo-1H-pyrazol-1-yl] benzenesulphonic acid or Reactive Yellow 15 free acid
- IUPAC name: 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid
- Molecular formula: C20H22N4O11S3
- Molecular weight: 590.609 g/mol
- Smiles : O=S(=O)(OCCS(=O)(=O)c1c(cc(\N=N\[C@@H]2C(=O)N(c3ccc(S(=O)(=O)O)cc3)N=C2C)c(OC)c1)C)O
- Inchl: 1S/C20H22N4O11S3/c1-12-10-16(17(34-3)11-18(12)36(26,27)9-8-35-38(31,32)33)21-22-19-13(2)23-24(20(19)25)14-4-6-15(7-5-14)37 (28,29)30/h4-7,10-11,19H,8-9H2,1-3H3,(H,28,29,30)(H,31,32,33)/b22-21+
- Substance type: Organic
- Physical state: Solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microrganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: %biodegradation (BOD)

Value:

0.143

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

The percent degradation of test chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid was estimated to be 0.142 % by considering BOD as parameter in 28 days.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 7 nearest neighbours
Domain  logical expression:Result: In Domain

((((("a" or "b" or "c" or "d" or "e" )  and "f" )  and "g" )  and ("h" and ( not "i") )  )  and ("j" and "k" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Vinyl Sulfones by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Schiff base formation AND Schiff base formation >> Pyrazolones and Pyrazolidinones derivatives AND Schiff base formation >> Pyrazolones and Pyrazolidinones derivatives >> Pyrazolones and Pyrazolidinones  by Protein binding by OASIS v1.3

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Acid moiety OR Amides OR Hydrazines by Aquatic toxicity classification by ECOSAR ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Direct Acylation Involving a Leaving group OR Acylation >> Direct Acylation Involving a Leaving group >> Acetates OR SN2 OR SN2 >> SN2 reaction at sp3 carbon atom OR SN2 >> SN2 reaction at sp3 carbon atom >> Alkyl diazo by Protein binding by OECD ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as SN1 OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic azo OR SN1 >> Nitrenium Ion formation >> Unsaturated heterocyclic azo by DNA binding by OECD ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as weeks - months by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as months and longer by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules by DPRA Cysteine peptide depletion

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as High reactive OR High reactive >> Activated haloarenes OR Low reactive OR Low reactive >> N-substituted aromatic amides OR Moderate reactive OR Moderate reactive >> Azalactones by DPRA Cysteine peptide depletion

Domain logical expression index: "j"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 300 Da

Domain logical expression index: "k"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 627 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The percent degradation of test chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid was estimated to be 0.142 % by considering BOD as parameter and microrganisms as inoculum in 28 days.

Executive summary:

Biodegradability of test chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid (CAS no. 60958-41-0) was estimated by using OECD QSAR tool box v3.3 by considering five closest read across chemicals with log Kow as primary descriptor. The percent degradation of test chemical  4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid was estimated to be 0.142 % by considering BOD as parameter and microrganisms as inoculum in 28 days. On The basis of value of percent biodegradabilty it is concluded that this test chemical is not readily biodegradable in 28 days.

Description of key information

Biodegradability of test chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid (CAS no. 60958-41-0) was estimated by using OECD QSAR tool box v3.3 by considering five closest read across chemicals with log Kow as primary descriptor. The percent degradation of test chemical  4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid was estimated to be 0.142 % by considering BOD as parameter and microrganisms as inoculum in 28 days. On The basis of value of percent biodegradabilty it is concluded that this test chemical is not readily biodegradable in 28 days.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data studies for target chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid (CAS no. 60958-41-0), one experimental study for its structurally similar red across chemical and one more experimental study for target chemical’s closest read across chemical with log kow as primary descriptor are summarized below for biodegradation in water endpoint.

 

In first weight of evidence study the biodegradability of test chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid (CAS no. 60958-41-0) was estimated by using OECD QSAR tool box v3.3 by considering five closest read across chemicals with log Kow as primary descriptor. The percent degradation of test chemical  4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid was estimated to be 0.142 % by considering BOD as parameter and microrganisms as inoculum in 28 days. On The basis of value of percent biodegradabilty it is concluded that this test chemical is not readily biodegradable in 28 days.

 

In another weight of evidence study the prediction was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzene-1-sulfonic acid (CAS no. 60958 -41 -0) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical  4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzene-1-sulfonic acid is expected to be not readily biodegradable.

 

Next weight of evidence study was done from Chemosphere, Vo1.15, No.4, pp 479-491, (1986) for structurally similar read across chemical Benzenesulfonic acid, 4-[4-[[2,5-dimethoxy-4-[(2-sulfoxy)ethyl]sulfonyl]phenyl]azo]-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl]-, dipotassium salt (CAS no.20317-19-5) in this study the aerobic biodegradation experiment was performed for read across chemical Benzenesulfonic acid, 4-[4-[[2,5-dimethoxy-4-[(2-sulfoxy)ethyl]sulfonyl]phenyl]azo]-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl]-, dipotassium salt using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100mg/L for 28 days. By considering DOC removal parameter read across chemical showed 10% degradation in 28 days. This percentage value is very less So it is concluded that read across chemical Benzenesulfonic acid, 4-[4-[[2,5-dimethoxy-4-[(2-sulfoxy)ethyl]sulfonyl]phenyl]azo]-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl]-, dipotassium salt is not readily biodegradable.

Last weight of evidence study was done from authoritative database (J check, 2017) in this study the read across chemical2-(3-((4-Amino-9,10-dihydro-3-sulpho-9,10-dioxoanthracen-4-yl)amino)benzenesulphonyl)vinyl disodium sulphate (CAS no. 2580-78-1)was subjected to biodegradation test by taking activated sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and HPLC parameters. The initial concentration of test chemical was 100 mg/L. The study design used was of standard type. The read across chemical2-(3-((4-Amino-9,10-dihydro-3-sulpho-9,10-dioxoanthracen-4-yl)amino)benzenesulphonyl)vinyl disodium sulphate showed 1 % degradation by BOD parameter, 22% degradation by TOC parameter and 8.0 % degradation by HPLC parameter in 28 days. Based on percent biodegradability it is concluded that read across chemical2-(3-((4-Amino-9,10-dihydro-3-sulpho-9,10-dioxoanthracen-4-yl)amino)benzenesulphonyl)vinyl disodium sulphate is not readily biodegradable.

On the basis of all the studies mentioned above it is concluded that target chemical 4-{4-[(E)-2-{2-methoxy-5-methyl-4-[2-(sulfooxy)ethanesulfonyl]phenyl}diazen-1-yl]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl} benzene-1-sulfonic acid (CAS no. 60958-41-0) can be considered as non readily biodegradable as both the predicted data have shown that it is not biodegradable and other two studies for read across chemicals support it.