Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate]

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:

key study

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 v3.4

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo] benzenesulphonate]
- IUPAC name: tetrasodium 2-[(E)-2-{2-acetamido-4-[4-({3-acetamido-4-[(E)-2-{2-sulfonato-4-[(E)-2-(4-sulfonatophenyl)diazen-1-yl]phenyl} diazen-1-yl]phenyl}carbamoyl)benzamido]phenyl}diazen-1-yl]-5-[(E)-2-(4-sulfonatophenyl)diazen-1-yl]benzene-1-sulfonate - Molecular formula: C48H34N12Na4O16S4
- Molecular weight: 1255.09 g/mole
- Smiles : [Na+].[Na+].[Na+].[Na+].c1(ccc(cc1)C(=O)Nc1cc(c(cc1)\N=N\c1c(cc(cc1)\N=N\c1ccc(cc1)S(=O)(=O)[O-])S(=O)(=O)[O-])NC(=O)C)C (=O)Nc1cc(c(cc1)\N=N\c1c(cc(cc1)\N=N\c1ccc(cc1)S(=O)(=O)[O-])S(=O)(=O)[O-])NC(=O)C
- Inchl: 1S/C48H38N12O16S4.4Na/c1-27(61)49-43-23-33(11-19-39(43)57-59-41-21-13-35(25-45(41)79(71,72)73)55-53-31-7-15-37(16-8-31) 77(65,66)67)51-47(63)29-3-5-30(6-4-29)48(64)52-34-12-20-40(44(24-34)50-28(2)62)58-60-42-22-14-36(26-46(42)80(74,75)76)56-54-32-9-17-38(18-10-32)78(68,69)70;;;;/h3-26H,1-2H3,(H,49,61)(H,50,62)(H,51,63)(H,52,64)(H,65,66,67)(H,68,69,70)(H,71,72,73)(H,74,75,76);;;;/q;4*+1/p-4/b55-53+,56-54+,59-57+,60-58+;;;;
- 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: % degradability BOD

Value:

0.167

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent biodegradation of the test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] was estimated to be 1.66 % by considering BOD as parameter and Microorganism as inoculum in 28 days

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 6 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide and Aminoalkylamine Side Chain by DNA binding by OASIS v.1.4

Domain logical expression index: "b"

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

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Acylation involving an activated (glucuronidated) carboxamide group AND Acylation >> Acylation involving an activated (glucuronidated) carboxamide group >> Carboxylic Acid Amides AND Acylation >> Direct acylation involving a leaving group AND Acylation >> Direct acylation involving a leaving group >> Carboxylic Acid Amides AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides AND AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Carboxylic Acid Amides by Protein binding by OASIS v1.4

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Direct Acylation Involving a Leaving group AND Acylation >> Direct Acylation Involving a Leaving group >> Acetates by Protein binding by OECD

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Acid moiety AND Amides AND Salt by Aquatic toxicity classification by ECOSAR

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 Alkali Earth AND Non-Metals by Groups of elements

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Alkaline Earth by Groups of elements

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Group 1 - Alkali Earth Li,Na,K,Rb,Cs,Fr AND Group 14 - Carbon C AND Group 15 - Nitrogen N AND Group 16 - Oxygen O AND Group 16 - Sulfur S by Chemical elements

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Group 17 - Halogens F by Chemical elements

Domain logical expression index: "k"

Similarity boundary:Target: CC(=O)Nc1cc(NC(=O)c2ccc(C(=O)Nc3ccc(N=Nc4ccc(N=Nc5ccc(S(=O)(=O)O{-}.[Na]{+})cc5)cc4S(=O)(=O)O{-}.[Na]{+})c(NC(C)=O)c3)cc2)ccc1N=Nc1ccc(N=Nc2ccc(S(=O)(=O)O{-}.[Na]{+})cc2)cc1S(=O)(=O)O{-}.[Na]{+}
Threshold=20%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "l"

Similarity boundary:Target: CC(=O)Nc1cc(NC(=O)c2ccc(C(=O)Nc3ccc(N=Nc4ccc(N=Nc5ccc(S(=O)(=O)O{-}.[Na]{+})cc5)cc4S(=O)(=O)O{-}.[Na]{+})c(NC(C)=O)c3)cc2)ccc1N=Nc1ccc(N=Nc2ccc(S(=O)(=O)O{-}.[Na]{+})cc2)cc1S(=O)(=O)O{-}.[Na]{+}
Threshold=40%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of log Kow which is >= 0.467

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of log Kow which is <= 3.88

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

Percent biodegradation of the test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] was estimated to be 1.66 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] is not readily biodegradable.

Executive summary:

Biodegradability of test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] (CAS no. 70210-30-9) was estimated by using OECD QSAR tool box v3.4 by considering six closest read across chemical log Kow as primary descriptor. Percent biodegradation of the test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] was estimated to be 1.66 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] is not readily biodegradable.

Description of key information

Biodegradability of test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] (CAS no. 70210-30-9) was estimated by using OECD QSAR tool box v3.4 by considering six closest read across chemical log Kow as primary descriptor. Percent biodegradation of the test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] was estimated to be 1.66 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data studies for target chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] (CAS no. 70210-30-9) and experimental studies for its structurally similar read across chemicals have been conducted and their results are summarized below.

In first predicted data study the biodegradability of test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] (CAS no. 70210-30-9) was estimated by using OECD QSAR tool box v3.4 by considering six closest read across chemical log Kow as primary descriptor. Percent biodegradation of the test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] was estimated to be 1.66 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] is not readily biodegradable.

Another predicted data study was done by using Estimation Programs Interface Suite (EPI suite, 2018) in this study the biodegradation potential of the test compound Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo] benzenesulphonate] (CAS no. 70210 -30 -9) was estimated 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 Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical  Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo] benzenesulphonate] is expected to be not readily biodegradable.

Next study was experimental study done for read across chemical done from (UERL, 2016) in this study 28-days Manometric respirometry test was conducted following the OECD guideline 301 F to determine the ready biodegradability of the read across chemical tetrasodium 1-acetamido-2-hydroxy-3-(4-((4-sulphonatophenylazo)-7-sulphonato-1-naphthylazo))naphthalene-4,6- disulphonate(CAS No. 2519-30-4). The test system included control, test read across and reference item. The concentration of read across and reference item (Sodium Benzoate) chosen for the study was 20 mg/l and 30 mg/l, while that of inoculum was10ml/l. ThOD (Theoretical oxygen demand) of test and reference item was determined by calculation. % Degradation was calculated using the values of BOD and ThOD for read across item and reference item. The BOD28 value of tetrasodium 1-acetamido-2-hydroxy-3-(4-((4-sulphonatophenylazo)-7-sulphonato-1-naphthylazo))naphthalene-4,6- disulphonate(CAS No. 2519-30-4) was observed to be 0.050mgO2/mg. ThOD was calculated as1.088 mgO2/mg. Accordingly, the % degradation of the read across item after 28 days of incubation at 20 ± 1°C according to manometric respirometry test was determined to be 4.596 %. Based on the results, the read across item, under the test conditions, was considered to be not readily biodegradable at 20 ± 1°C over a period of 28 days.

Next experimental study was done from authoritative data base (J check, 2017) for read across chemical in this study the read across chemical Barium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]toluene-4-sulphonate] (CAS no. 5160-02-1)was subjected to biodegradation test by taking sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD parameter. The initial concentration of read across chemical was 100 mg/L. After 2 weeks (14 days) test chemical Barium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]toluene-4-sulphonate] showed 0 % biodegradability by BOD parameter and by taking activated sludge as inoculumin 14 days so it is concluded that read across chemical Barium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]toluene-4-sulphonate] is not readily biodegradable.

Similarly one more study was done from authoritative database (J check, 2017) in this study the read across chemical tetrasodium 3,3'-[carbonylbis[imino(2-methyl-4,1-phenylene)azo]]bisnaphthalene-1,5-disulphonate (CAS no. 3214-47-9) was subjected to biodegradation test by taking sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and HPLC parameters. The initial concentration of read across chemical was 100 mg/L and study design was of standard type. The read across chemical tetrasodium 3,3'-[carbonylbis[imino(2-methyl-4,1-phenylene)azo]]bisnaphthalene-1,5-disulphonate showed 13 % biodegradation by TOC parameter and 0 % biodegradation by other two parameters namely BOD and HPLC in 28 days. Based on percent biodegradability it is concluded that read across chemical tetrasodium 3,3'-[carbonylbis[imino(2-methyl-4,1-phenylene)azo]]bisnaphthalene-1,5-disulphonate is not readily biodegradable.

Last experimental study was done from another 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 Tetrasodium 2,2'-[1,4-phenylenebis[carbonylimino[2-acetamido-4,1-phenylene]azo]]bis[5-[(4-sulphonatophenyl)azo]benzenesulphonate] (CAS no. 70210-30-9)is not readily biodegradable