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Biodegradation in water: screening tests

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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:
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 : Chromate(1-), [2,4-dihydro-4-[(2-hydroxy-5-methyl-3-nitrophenyl)azo]-5-methyl-2-phenyl-3H-pyrazol-3-onato(2-)][3-[4-[[5-(2,2-dimethylpropyl)-2-hydroxy-3-nitrophenyl]azo]-4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl]benzenesulfonamidato(2-)]-, hydrogen
- Molecular formula : C38H36CrN11O10S
- Molecular weight : 890.831 g/mol
- Smiles notation : [Cr+3].c1(N2C([C@@-](C(=N2)C)\N=N\c2cc(cc([N+]([O-])=O)c2[O-])CC(C)(C)C)=O)cc(S(N)(=O)=O)ccc1.c1(ccccc1)N1N=C([C@@-](C1=O)\N=N\c1c(c(cc(c1)C)[N+]([O-])=O)[O-])C
- InChl : 1S/C21H23N6O6S.C17H14N5O4.Cr/c1-12-18(20(29)26(25-12)14-6-5-7-15(10-14)34(22,32)33)24-23-16-8-13(11-21(2,3)4)9-17(19(16)28)27(30)31;1-10-8-13(16(23)14(9-10)22(25)26)18-19-15-11(2)20-21(17(15)24)12-6-4-3-5-7-12;/h5-10,28H,11H2,1-4H3,(H2,22,32,33);3-9,23H,1-2H3;/q2*-1;+3/p-1/b24-23+;19-18+;
- Substance type: Organic
- Physical state: Solid
Oxygen conditions:
aerobic
Inoculum or test system:
other: Micro-organisms
Duration of test (contact time):
28 d
Based on:
not specified
Parameter followed for biodegradation estimation:
other: BOD
Key result
Parameter:
other: BOD
Value:
0.4
Sampling time:
28 d
Remarks on result:
other: Other details not known
Details on results:
Test substance undergoes 0.4% 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 5 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as m,p - Cresols by OECD HPV Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Michael addition AND Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals AND Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Alkyl phenols AND SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Aromatic azo AND SN1 >> Nitrenium Ion formation >> Aromatic nitro AND SN1 >> Nitrenium Ion formation >> Unsaturated heterocyclic 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) sulfonamide group AND Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group >> Arenesulfonamides AND AN2 AND AN2 >> Michael addition to activated double bonds in heterocyclic ring systems AND AN2 >> Michael addition to activated double bonds in heterocyclic ring systems >> Pyrazolone and Pyrazolidine Derivatives AND AN2 >> Nucleophilic addition at polarized N-functional double bond AND AN2 >> Nucleophilic addition at polarized N-functional double bond >> Arenesulfonamides AND AN2 >> Schiff base formation with carbonyl compounds (AN2) AND AN2 >> Schiff base formation with carbonyl compounds (AN2) >> Pyrazolone and Pyrazolidine Derivatives AND Schiff base formation AND Schiff base formation >> Schiff base on pyrazolones and pyrazolidinones AND Schiff base formation >> Schiff base on pyrazolones and pyrazolidinones >> Pyrazolones and Pyrazolidinones 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 No alert found by DNA binding by OASIS v.1.4

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinoneimines OR AN2 >>  Michael-type addition, quinoid structures >> Quinones and Trihydroxybenzenes 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 Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> Coumarins 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) >> Coumarins 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) >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR Radical >> ROS formation after GSH depletion (indirect) OR Radical >> ROS formation after GSH depletion (indirect) >> Quinoneimines 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 nitrenium ion formation OR SN1 >> Nucleophilic attack after 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 SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters 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 >> Alkylation, ring opening SN2 reaction OR SN2 >> Alkylation, ring opening SN2 reaction >> Four- and Five-Membered Lactones OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Coumarins 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.1.4

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 longer than months by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "i"

Parametric boundary:The target chemical should have a value of BAF which is >= 0.448 log(L/kg wet)

Domain logical expression index: "j"

Parametric boundary:The target chemical should have a value of BAF which is <= 2.15 log(L/kg wet)

Validity criteria fulfilled:
not specified
Interpretation of results:
under test conditions no biodegradation observed
Conclusions:
The test chemical Chromate(1-), [2,4-dihydro-4-[(2-hydroxy-5-methyl-3-nitrophenyl)azo]-5-methyl-2-phenyl-3H-pyrazol-3-onato(2-)][3-[4-[[5-(2,2-dimethylpropyl)-2-hydroxy-3-nitrophenyl]azo]-4,5-dihydro- 3-methyl-5-oxo-1H-pyrazol-1-yl]benzenesulfonamidato(2-)]-, hydrogen was estimated to be not readily biodegradable in water.
Executive summary:

Biodegradability of Chromate(1-), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen (CAS no. 72928 -87 -1) is predicted using QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 0.4% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro- 3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of Chromate(1-), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen (CAS no. 72928 -87 -1) is predicted using QSAR toolbox version 3.4 (2018) with logKow as the primary descriptor. Test substance undergoes 0.4% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro- 3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen 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 Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen (CAS No. 72928 -87 -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 (2018) using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemical Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen (CAS No. 72928 -87 -1) was estimated.Test substance undergoes 0.4% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen was estimated to be not readily biodegradable in water.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol (CAS no. 2425 -85 -6),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol.Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 1 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol was determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 1 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol is considered to be not readily biodegradable in nature.

 

For the read across chemical 3 -nitro-N-phenyl-4 -(phenylamino)benzene-1 -sulfonamide (CAS no. 5124 -25 -4), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 3 -nitro-N-phenyl-4 -(phenylamino)benzene-1 -sulfonamide (CAS no. 5124 -25 -4) (J-CHECK, 2017 and EnviChem, 2014). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 3 -nitro-N-phenyl-4 -(phenylamino)benzene-1 -sulfonamide was determined to be 0 and 5% by BOD and UV-Vis parameter in 28 days. Thus, based on percentage degradation, 3-nitro-N-phenyl-4-(phenylamino)benzene-1-sulfonamide is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfonamidato(2 -)]-, hydrogen (from OECD QSAR toolbox version 3.4, 2018) and for its read across substance (from authoritative database J-CHECK and Envichem), it can be concluded that the test substance Chromate(1 -), [2,4 -dihydro-4 -[(2 -hydroxy-5 -methyl-3 -nitrophenyl)azo]-5 -methyl-2 -phenyl-3H-pyrazol-3 -onato(2 -)][3 -[4 -[[5 -(2,2 -dimethylpropyl)-2 -hydroxy-3 -nitrophenyl]azo]-4,5 -dihydro-3 -methyl-5 -oxo-1H-pyrazol-1 -yl]benzenesulfon amidato(2 -)]-, hydrogen can be expected to be not readily biodegradable in nature.