Dialuminium tris[2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate]

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 data is predicted using the OECD QSAR Toolbox version 3.4 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material : Dialuminium tris[2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate]
- Molecular formula:C20H4Br4Cl4O5 2/3Al
- Molecular weight : 2404.904 g/mol
- Smiles notation : C1=C2C(=C3C=C(C(=O)C(=C3OC2=C(C(=C1Br)[O-])Br)Br)Br)C4=C(C(=C(C(=C4Cl)Cl)Cl)Cl)C(=O)[O-].C1=C2C(=C3C=C(C(=O)C(=C3OC2=C(C(=C1Br)[O-])Br)Br)Br)C4=C(C(=C(C(=C4Cl)Cl)Cl)Cl)C(=O)[O-].C1=C2C(=C3C=C(C(=O)C(=C3OC2=C(C(=C1Br)[O-])Br)Br)Br)C4=C(C(=C(C(=C4Cl)Cl)Cl)Cl)C(=O)[O-].[Al+3].[Al+3]
- InChl : 1S/3C20H4Br4Cl4O5.2Al/c3*21-5-1-3-7(8-9(20(31)32)13(26)15(28)14(27)12(8)25)4-2-6(22)17(30)11(24)19(4)33-18(3)10(23)16(5)29;;/h3*1-2,29H,(H,31,32);;/q;;;2*+3/p-6
- Substance type : Organic
- Physical state: Solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Based on:

not specified

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

1.817

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 1.82% degradation by using BOD parameter 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" )  and "e" )  and "f" )  and "g" )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and "l" )  and ("m" and "n" )  )

Domain logical expression index: "a"

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

Domain logical expression index: "b"

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 SNAr OR SNAr >> Nucleophilic aromatic substitution OR SNAr >> Nucleophilic aromatic substitution >> Activated halo-benzenes by Protein binding by OECD ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as High reactive AND High reactive >> Activated haloarenes by DPRA Cysteine peptide depletion

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Low reactive AND Low reactive >> Activated haloarenes by DPRA Lysine peptide depletion

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 2) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.4

Domain logical expression index: "i"

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 and Trihydroxybenzenes 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 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 and Aminoalkylamine Side Chain OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes 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) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroarenes with Other Active Groups OR Radical >> Radical mechanism via ROS formation (indirect) >> Polynitroarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes OR SN1 OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation >> Nitroarenes with Other Active Groups 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 reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroarenes with Other Active Groups OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Polynitroarenes OR SN2 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, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkanes Containing Heteroatom 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 after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 >> Nitroarenes with Other Active Groups by DNA binding by OASIS v.1.4

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Aromatic alcohol  [-OH] AND Aromatic bromide   [-Br] AND Aromatic chloride   [-CL] AND Aromatic ether  [-O-aromatic carbon] AND Aromatic-H AND Carbon with 4 single bonds & no hydrogens AND Ester   [-C(=O)-O-C] by Biodegradation fragments (BioWIN MITI)

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Amide   [-C(=O)-N  or -C(=S)-N] OR Aromatic acid   [-C(=O)-OH] OR Aromatic amine   [-NH2  or  -NH-] OR Aromatic-CH2 OR Aromatic-CH3 OR -C=CH  [alkenyl hydrogen] OR -CH -  [cyclic] OR -CH-   [linear] OR -CH2-  [cyclic] OR -CH2-  [linear] OR Methyl  [-CH3] OR Sulfonic acid / salt -> aromatic attach OR Tertiary amine OR Tin  [Sn] by Biodegradation fragments (BioWIN MITI)

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Not bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 250 Da

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 960 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) (CAS no. 15876 -58 -1) is predicted using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 1.82% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) (CAS no. 15876 -58 -1) is predicted using OECD QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 1.82% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) was estimated to be not readily biodegradable in water.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data for the target compound Dialuminium tris(2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxoxanthen-9 -yl)-3,4,5,6 -tetrachlorobenzoate) (CAS No. 15876 -58 -1) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemicalDialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate)was estimated.Test substance undergoes 1.82% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) was estimated to be not readily biodegradable in water.

 

In a supporting weight of evidence study from peer reviewed journal (U. Pagga and O. Brown, 1986) for the read across chemical Disodium 2-(2,4,5,7-tetrabromo-6-oxido-3-oxo-3H-xanthen-9-yl)benzoate (CAS no. 17372-87-1),biodegradation experiment was carried out for 42 days for evaluating the percentage biodegradation of the read across chemical 2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxo-3H-xanthen-9 -yl) using modified OECD Guideline 302B. Activated sludge was used as an inoculum. The sources of the activated sludge were treatment plants conveniently located to the laboratories carrying out the test. These treatment plants received communal and/or industrial wastewater. Concentration of inoculum i.e, activated sludge used was 0.5 g/l and initial test substance conc. used in the study was 100 mg/l. Analytical methods involve the measurement of extinction at absorption maximum 412 nm and DOC (dissolved organic carbon).The percentage degradation of the read across substance 2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxo-3H-xanthen-9 -yl ) was determined to be -3% by using DOC removal parameter. Thus, based on percentage degradation of 2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxo-3H-xanthen-9 -yl) was considered to be not readily biodegradable in nature.

 

For the read across chemical 2',4',5',7'-tetrabromo-4,5,6,7-tetrachloro-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one (Phloxine B) (CAS no. 18472-87-2), the biodegradability of phloxine B was studied using methods: Aerobic degradability, Warburg method and BOD measurement. Return activated sludge was obtained from the municipal sewage treatment plant, Nakahama, Osaka. Synthetic sewage preparation: Glucose, peptone and potassium dihydrogen phosphate, 30g each, were dissolved in 1 liter water and the pH was adjusted to pH 7.0 with sodium hydroxide. Seeded Dilution water: To 1 liter, 10 ml of supernatant of sludge was added. Aerobic biodegradation assay: To 750ml of sludge (MLSS ca, 3,000 ppm) 250 ml of O.03 M dye solution was added, and bubbled with air sufficiently at 20°C. 5ml sample was taken out once a day. After sampling 5ml of synthetic sewage was added to the mixture. Each sample was filtered through filter paper and diluted twenty times prior to the spectrophotometric measurement at the absorption maximum within the visible range. The decrease of dyes concentration was expressed in terms of percent to the initial absorption. The experiment was carried out for 10 days. Oxygen uptake of sludge [Warburg Method]- 2.0 ml of sludge, 0.2 ml of 1000 ppm dye solution, and 0.2 ml of 20% potassium hydroxide were pipetted into the vessel, the side arm and central well, respectively. The sludge and the dye solution were mixed and the vessel was shaken at 25°C. The oxygen uptake was measured. The oxygen uptake by sludge alone was subtracted from those by dyes addition.

Determination of BOD – Dye solution (10, 20, and 40 ppm) were prepared with the seeded dilution water and kept at 20°C (Japanese Industrial Standards Committee, 1971). The dissolved oxygen contents were measured by a dissolved oxygen meter, because of the coloration of the solutions. The COD, BOD and absorbance at 245 and 545 nm (representing ultraviolet and the visible absorbance) of Phloxine B was studied. During 10 days of the aerobic experiment, the absorbance of dye solution was measured once day for 10 days. Food Red No. 104 was scarcely decreased.Free acids of Red No.104, was precipitated due to the slight acidity (pH 6-7) of the solution. The percentage degradation of read across substance 2',4',5',7'-tetrabromo-4,5,6,7-tetrachloro-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one (Phoxine B) was determined to be 0% by using Test mat. analysis and Oxygen uptake in 10 days. Thus, based on percentage degradation 2',4',5',7'-tetrabromo-4,5,6,7-tetrachloro-3',6'-dihydroxy-3H-spiro [2-benzofuran-1,9'-xanthen]-3-one was considered to be not readily biodegradable in nature.

 

Another Biodegradation study was conducted for 5 days for evaluating the percentage biodegradability of read across substance Dipotassium 3,6 -dichloro-2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxoxanthen-9 -yl)benzoate (CAS no. 6441 -77 -6) using standard dilution method at a temperature of 20°C (H. Heukelekian and M. C. Rand, 1955). Sewage was used as a test inoculum. The 5 day BOD value of chemical Dipotassium 3,6 -dichloro-2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxoxanthen-9 -yl)benzoate was determined to be 0 g/g. Thus, based on this value, Dipotassium 3,6 -dichloro-2 -(2,4,5,7 -tetrabromo-6 -oxido-3 -oxoxanthen-9 -yl)benzoate is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemicalDialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) (from OECD QSAR toolbox version 3.4, 2017) and for its read across substance (from peer reviewed journals), it can be concluded that the test substance Dialuminium tris(2-(2,4,5,7-tetrabromo-6-oxido-3-oxoxanthen-9-yl)-3,4,5,6-tetrachlorobenzoate) can be expected to be not readily biodegradable in nature.