4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic 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 data is predicted using the OECD QSAR toolbox version 3.3 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (IUPAC name): 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid
- Molecular formula : C18H16N4O12S3
- Molecular weight : 576.538 g/mol
- Smiles notation : O=C(O)C1=NN(C(=O)[C@@H]1\N=N\c1ccc(S(=O)(=O)CCOS(=O)(=O)O)cc1)c1ccc(S(=O)(=O)O)cc1
- InChl : 1S/C18H16N4O12S3/c23-17-15(16(18(24)25)21-22(17)12-3-7-14(8-4-12)36(28,29)30)20-19-11-1-5-13(6-2-11)35(26,27)10-9-34-37(31,32)33/h1-8,15H,9-10H2,(H,24,25)(H,28,29,30)(H,31,32,33)/b20-19+
- 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:

4.137

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 4.137% degradation by BOD 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 "g" )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and ("l" and ( not "m") )  )  and ("n" and "o" )  )

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 Acid moiety OR Amides OR Hydrazines by Aquatic toxicity classification by ECOSAR ONLY

Domain logical expression index: "c"

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: "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 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 days - weeks by Biodeg primary (Biowin 4) 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 Not categorized by Repeated dose (HESS)

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Benzene/ Naphthalene sulfonic acids (Less susceptible) Rank C OR Hydrazines (Hemolytic anemia with methemoglobinemia) Rank B OR Hydrazines (Hepatotoxicity) Rank C by Repeated dose (HESS)

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Aromatic compound AND Carbonic acid derivative AND Carboxylic acid derivative AND Heterocyclic compound AND Sulfonic acid AND Sulfonic acid derivative AND Sulfuric acid derivative AND Sulfuric acid monoester by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Acetal OR Alkyl chloride OR Alkyl fluoride OR Alkyl halide by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] AND Aliphatic Carbon [CH] AND Aliphatic Carbon [-CH2-] AND Aliphatic Nitrogen, one aromatic attach [-N] AND Amide, aliphatic attach [-C(=O)N] AND Amino, aliphatic attach [-N<] AND Amino-carbonyl compound [NCC(=O)-C] AND Aromatic Carbon [C] AND Azo [-N=N-] AND Azomethine, aliphatic attach [-N=C] AND Carbonyl, aliphatic attach [-C(=O)-] AND Carbonyl, olefinic attach [-C(=O)-] AND Hydrazine [>N-N<] AND Hydroxy, sulfur attach [-OH] AND Miscellaneous sulfide (=S) or oxide (=O) AND Nitrogen, two or tree olefinic attach [>N-] AND Olefinic carbon [=CH- or =C<] AND Suflur {v+4} or {v+6} AND Sulfate, linear [-O-SO2-O-] AND Sulfinic acid [-S(=O)OH] AND Sulfite, linear [-OS(=O)O-] AND Sulfonate, aromatic attach [-SO2-O] AND Sulfonic [SO2(-OH)-O] by Organic functional groups (US EPA)

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as -CO-N-CO five member ring (not pyrroledione) OR Cyclic ester by Organic functional groups (US EPA)

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 218 Da

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 605 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid (CAS no. 10149 -98 -1) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 4.137% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid (CAS no. 10149 -98 -1) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 4.137% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid 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

Various predicted data for the target compound 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid (CAS No. 10149-98-1) and supporting weight of evidence studies for its structurally similar 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 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid(CAS No. 10149-98-1) was estimated.Test substance undergoes 4.137% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acidwas estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid(CAS No. 10149-98-1) in the presence of mixed populations of environmental microorganisms was estimated.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 chemical4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acidis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from peer reviewed journal (Yasuhide TONOGAI et. al; 1978) for the read across chemical Trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylate (CAS no. 1934-21-0),biodegradation study was conducted under aerobic conditions for evaluating the percentage biodegradability of read across substance Trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylate (CAS no. 1934-21-0). Activated sludge was used as a test inoculum obtained from the municipal sewage treatment plant, Nakahama, Osaka. The return sludge was acclimated to the synthetic sewage for a week or longer, and it was used for the aerobic and anaerobic decomposition experiments. Synthetic sewage was prepared by dissolving Glucose, peptone and potassium dihydrogen phosphate, 30g each, in 1 liter water and the pH was adjusted to pH 7.0 with sodium hydroxide. Concentration of inoculum used for the study was3000 mg/l. Percentage degradation of chemical was determined by measuring the absorbance (test material analysis), oxygen uptake and BOD parameter. For the aerobic decomposition of dyes with sludge, 250 ml of O.03 M dye solution was added to 750ml of sludge (MLSS ca, 3,000 ppm), 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 whereas measurement oxygen uptake by sludge involve 2.0 ml of sludge, 0.2 ml of 1,000 ppm dye solution, and O.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 the dye addition. For determining the BOD values, test chemical solutions (10, 20 and 40 ppm) were prepared with the seeded dilution water and kept at 20°C. The dissolved oxygen contents were then measured by using a dissolved oxygen meter. The percentage degradation of test chemical Trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylatewas determined to be 20% in 10 days by using the test material analysis parameter. From the oxygen uptake by Warburg’s manometer, the low activity of the sludge to dye was obtained and by using the dissolved oxygen meter, the dissolved oxygen contents on the 5th day were essentially the same to initial ones. Thus, based on percentage degradation, the chemical Trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylatewas considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for evaluating the percentage biodegradation of the same read across chemical C. I. Acid Yellow 23 (CAS no. 1934-21-0) (from peer reviewed journal Glenn M. Shaul et. al; 1991 and secondary source Glenn M. Shaul et. al; 1988). The study was carried out in pilot activated sludge process system using several wastewater and mixed liquor at a temperature of 21-25°C and pH range of 7.0-8.0, respectively. Mass balance calculations were made to determine the amount of the dye compound in the waste activated sludge (WAS) and in the activated sludge effluent (ASE). Activated sludge was used as test inoculum for the study. Test chemical conc. used for the study was 1 and 5 mg/l, respectively. Screened raw wastewater from the Greater Cincinnati Mill Creek Sewage Treatment Plant was used as the influent (INF) to three pilot-scale activated sludge biological treatment systems (two experimental and one control) operated in parallel. Each system consisted of a primary clarifier (33 L), complete-mix aeration basin (200 L), and a secondary clarifier (32 L). Each water soluble dye was dosed as commercial product to the screened raw wastewater for the two experimental systems operated in parallel at targeted active ingredient doses of 1 and 5 mg/L of influent flow (low and high spike systems, respectively).All systems were operated for at least three times. All samples were 24 hr composites made up of 6 grab samples collected every 4 hr and stored at 4°C study. The possible removal mechanisms for a dye compound in the ASP system include adsorption, biodegradation, chemical transformation, photodegradation, and air stripping. Dye analytical recovery studies were conducted by dosing the purified dye compound into organic-free water, influent wastewater, and mixed liquor. These studies were run in duplicate and each recovery study was repeated at least once to ensure that the dye compound could be extracted. Purified dye standards were analytically prepared from the commercial dye product by repeated recrystallization. The INF, primary effluent (PE), and ASE were filtered, and the filtrate was passed through a 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 up to 50 mL volume with a methanol/dimethylformamide solution. The mixed liquor (ML) samples were separated into two components, the filtrate or soluble (SOL) fraction and the residue (RES) fraction. The SOL fraction was processed similar to the INF, PE, and ASE samples. The RES fraction and the filter paper were processed similar to these samples but the resin adsorption step was omitted. All extracted samples were analyzed by HPLC with an ultraviolet-visible detector. Total suspended solids (TSS) analyses were also performed on the INF, PE, ML, and ASE samples. Percentage recovery of chemical C. I. Acid Yellow 23was determined to be 103-107%,thus, it appeared that little or no chemical transformation occurred for test chemical because of contact with the variable wastewater and/or sludge matrix under these conditions. Also it was evaluated that the chemical C. I. Acid Yellow 23 was adsorbed at a level of˂1% on the ML solids, indicating that the compound was substantially untreated by the activated sludge process (ASP). Thus, based on %recovery of test chemical, chemical C. I. Acid Yellow 23 was can be considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid (from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from peer reviewed journals and secondary source), it can be concluded that the test substance 4,5-dihydro-5-oxo-4-[[4-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]-1-(4-sulphophenyl)-1H-pyrazole-3-carboxylic acid can be expected to be not readily biodegradable in nature.