Trisodium 2-[[4,5-dihydro-3-methyl-5-oxo-1-[4-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]-1H-pyrazol-4-yl]azo]naphthalene-1,5-disulphonate

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 the test chemical: Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)
diazen-1-yl]naphthalene-1,5-disulfonate
- IUPAC name: trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene -1,5-disulfonate
- Molecular Formula: C22H17N4Na3O13S4
- Molecular Weight: 742.6253 g/mol
- SMILES Notation: [Na+].CC1C(N=Nc2ccc3c(S(=O)(=O)[O-])cccc3c2S(=O)(=O)[O])C(=O)N(c2ccc(S(=O)(=O)CCOS(=O)(=O)[O-])cc2)N=1.[Na+].[Na+]
- InChI: 1S/C22H20N4O13S4.3Na/c1-13-20(22(27)26(25-13)14-5-7-15(8-6-14)40(28,29)12-11-39-43(36,37)38)24-23-18-10-9-16-17(21(18)42
(33,34)35)3-2-4-19(16)41(30,31)32;;;/h2-10,20H,11-12H2,1H3,(H,30,31,32)(H,33,34,35)(H,36,37,38);;;/q;3*+1/p-3/b24-23+;;;
- Substance Type: Organic
- Physical State: Solid

Oxygen conditions:

not specified

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

0.75

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent biodegradadtion of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate was estimated to be 0.75 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 8 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Naphthalene sulfonic acids, condensates by OECD HPV Chemical Categories

Domain logical expression index: "b"

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

Domain logical expression index: "c"

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: "d"

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

Domain logical expression index: "e"

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: "f"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinones OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds >> Four- and Five-Membered Lactones OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Geminal Polyhaloalkane Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Generation of ROS by glutathione depletion (indirect) OR Radical >> Generation of ROS by glutathione depletion (indirect) >> Haloalkanes Containing Heteroatom OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Amino Anthraquinones OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Geminal Polyhaloalkane Derivatives OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives OR SN2 >> Alkylation, ring opening SN2 reaction OR SN2 >> Alkylation, ring opening SN2 reaction >> Four- and Five-Membered Lactones OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Vicinal Dihaloalkanes OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) >> Vicinal Dihaloalkanes OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "h"

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

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Non binder, MW>500 by Estrogen Receptor Binding

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Strong binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "k"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 506 Da

Domain logical expression index: "l"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 889 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

Percent biodegradadtion of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate was estimated to be 0.75 by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

Executive summary:

Biodegradability of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate (CAS no. 20298 -05 -9) was estimated by using OECD QSAR tool box v3.3 considering eight closest read across chemical with log Kow as primary descriptor. Percent biodegradadtion of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate was estimated to be 0.75 by considering BOD as parameter  and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate

(CAS no. 20298 -05 -9) was estimated by using OECD QSAR tool box v3.3 considering eight closest read across chemical with log Kow as primary descriptor. Percent biodegradation of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate was estimated to be 0.75 by considering BOD as parameter  and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

 Predicted data for target chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate(CAS no. 20298 -05 -9) and experimental studies for its read across chemical are summarized below for biodegradation endpoint.

 

In first weight of evidence study the biodegradability of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate(CAS no. 20298 -05 -9) was estimated by using OECD QSAR tool box v3.3 considering eight closest read across chemical with log Kow as primary descriptor. Percent biodegradation of test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate was estimated to be 0.75 by considering BOD as parameter  and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

 

Another weight of evidence study was done from Chemosphere Vol 22 pp 107-119 1991 by Glenn M Shaul, Thomas J Holdsworth, Clyde R. Dempsey, and Kenneth A. Dostal in this study the Biodegradability of read across chemical trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylate (Acid yellow 23) was determined by anlysing percent recovery of test material. This read across material is dye and inoculums used for biodegradation was obtained from Screened raw waste water from greater Cincinnati Mill Creek sewage treatment plant was used as influent (INF) to three pilot scale activated sludge biological treatment systems (Two experimental and one control). Each system consists of primary clarifier, complete mix aeration basin and secondary clarifier. Influent was spiked with test material at concentration of 1 mg/L and 5 mg/L. Then Dye analytical studies were conducted by purified dye compound in organic free influent waste water and mixed liquor. Then influent, primary influent filtrate was passed through column packed with resin. The filter paper and resin were soaked in an ammonia – acetonitrile solution and then soxhlet extracted with ammonia – acetonitrile. The extract was concentrated and brought upto 50 ml volumn with methanol/dimethyl formamaide solution. All extracted samples were analyzed by HPLC with ultraviolet detector.  Percent recovery determined was 107 % in low spiked and 103 % in high spiked. On the basis of percent recovery value biodegradation of dye was negligible i.e., 0%. Percent biodegradation of read across chemical trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylatewas observed to be 0.0 % by test material analysis by HPLC parameter. On the basis of percent degradation it is concluded that this test material is not readily biodegradable.

 

Next weight of evidence study was done from The Journal of Toxicological Sciences, Vol.3 , 193 -204, (1978) by Yasuhide TONOGAI, Masahiro IWAIDA, Masatomo TATI, Youki OsE and Takahiko SATO . The aim of the study was to estimate the microbial decomposition of read across chemical Food yellow 4 dye. The biodegradation of chemical was determined by 3 methods under aerobic conditions: Aerobic decomposition of dyes with sludge, Oxygen uptake and BOD determination.

During 10 days of the aerobic experiment, the absorbance of dye solution was measured once in a day for 10 days. 20% decomposition of read across chemical was obtained in 10 days. 3.82 O2 mg/hg – sludge oxygen uptake was obtained in 5 –hrs test and the dissolved oxygen contents on the 5th day were essentially the same to initial ones. The low reactivity of aerobic sludge towards dyes was confirmed.

Based on the results obtained from the aerobic degradation assay, Warburg method and BOD determination it can be concluded that this read across is not readily biodegradable under aerobic conditions.

 

Next study was also conducted for read across from the Journal of Toxicological Sciences, Vol.3 , 193 -204, (1978) in this study the Biodegradability of read across chemical Sodium 4-(4-(2-hydroxynaphthalenylazo)phenylazo) benzenesulphonate (Acid Red 151) was determined by analyzing percent recovery of test material. This test material is dye and inoculums used for biodegradation was obtained from Screened raw waste water from greater Cincinnati Mill Creek sewage treatment plant was used as influent (INF) to three pilot scale activated sludge biological treatment systems (Two experimental and one control). Each system consists of primary clarifier, complete mix aeration basin and secondary clarifier. Influent was spiked with test material at concentration of 1 mg/L and 5 mg/L. Then Dye analytical studies were conducted by purified dye compound in organic free influent waste water and mixed liquor. Then influent, primary influent filtrate was passed through column packed with resin. The filter paper and resin were soaked in an ammonia – acetonitrile solution and then soxhlet extracted with ammonia – acetonitrile. The extract was concentrated and brought upto 50 ml volumn with methanol/dimethyl formamaide solution. All extracted samples were analyzed by HPLC with ultraviolet detector. Percent recovery and Percent adsorbed of read across chemical Sodium 4-(4-(2-hydroxynaphthalenylazo)phenylazo)benzenesulphonatewas observed was 82% and 50 % in low spike of test chemical and 70 % and 58% at high spike of read across chemical respectively. On the basis of percent recovery value biodegradation of dye was 9.0 % at low spike and 15 % at high spike of read across chemical. On the basis of percent degradation it is concluded that this read across material is not readily biodegradable.

 

Last weight of evidence study was done from authoritative database (HSDB, 2017) in this study the read across chemical disodium 6-hydroxy-5-[(4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate (CAS no. 2783-94-0) showed 0.0% biodegradation by considering BOD as parameter in 5 days, and by taking sewage as inoculums. So it is concluded that read across chemical disodium 6-hydroxy-5-[(4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate is not readily biodegradable.

 

On the basis of all the studies mentioned above it can be concluded that test chemical Trisodium 2-[(E)-2-(3-methyl-5-oxo-1-{4-[2-(sulfonatooxy)ethanesulfonyl]phenyl}-4,5-dihydro-1H-pyrazol-4-yl)diazen-1-yl]naphthalene-1,5-disulfonate  (CAS No. 20298-05-9) is expected to be not readily biodegradable.