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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
Reference:
Composition 1
Qualifier:
equivalent or similar 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
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material (as cited in study report): 4-nitrobenzene-1,3-diamine
- Molecular formula (if other than submission substance): C6H7N3O2
- Molecular weight (if other than submission substance): 153.14 g/mol
- Smiles notation (if other than submission substance): c1(c(cc(N)cc1)N)[N+](=O)[O-]
- InChI: 1S/C6H7N3O2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H,7-8H2
- Substance type: Organic
- Physical state: Solid
Oxygen conditions:
aerobic
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:
0.857
Sampling time:
28 d
Remarks on result:
other: Other details not known
Details on results:
Test substance undergoes 0.85% 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 7 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Anilines (Acute toxicity) by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Aminoaniline, meta AND Aniline AND Aryl AND Nitrobenzene by Organic Functional groups

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Aminoaniline, meta AND Nitrobenzene AND Overlapping groups by Organic Functional groups (nested)

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Aliphatic Nitrogen, one aromatic attach [-N] AND Aromatic Carbon [C] AND Miscellaneous sulfide (=S) or oxide (=O) AND Nitro, aromatic attach [-NO2] AND Olefinic carbon [=CH- or =C<] by Organic functional groups (US EPA)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Amine AND Aromatic compound AND Nitro compound AND Primary amine AND Primary aromatic amine by Organic functional groups, Norbert Haider (checkmol)

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 Does NOT Biodegrade Fast by Biodeg probability (Biowin 2) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Substituted Anilines by Protein binding by OASIS v1.4

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Acylation involving an activated (glucuronidated) carboxamide group OR Acylation >> Acylation involving an activated (glucuronidated) carboxamide group >> Carboxylic Acid Amides OR Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group OR Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group >> Arenesulfonamides OR Acylation >> Direct acylation involving a leaving group OR Acylation >> Direct acylation involving a leaving group >> Carboxylic Acid Amides OR Acylation >> Ester aminolysis OR Acylation >> Ester aminolysis >> Amides OR AN2 >> Michael addition to activated double bonds OR AN2 >> Michael addition to activated double bonds >> alpha,beta-Unsaturated Carbonyls and Related Compounds OR AN2 >> Michael-type addition to quinoid structures  >> Carboxylic Acid Amides OR AN2 >> Michael-type addition to quinoid structures  >> N-Substituted Aromatic Amines OR AN2 >> Nucleophilic addition at polarized N-functional double bond OR AN2 >> Nucleophilic addition at polarized N-functional double bond >> Arenesulfonamides OR Michael addition OR Michael addition >> Michae addition on quinoide type compounds OR Michael addition >> Michae addition on quinoide type compounds >> Quinone methide(s)/imines; Quinoide oxime structure; Nitroquinones, Naphthoquinone(s)/imines  OR No alert found OR Schiff base formation OR Schiff base formation >> Schiff base formation with carbonyl compounds OR Schiff base formation >> Schiff base formation with carbonyl compounds >> Aromatic carbonyl compounds by Protein binding by OASIS v1.4

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as High (Class III) by Toxic hazard classification by Cramer (extension) ONLY

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Aromatic amine   [-NH2  or  -NH-] AND Aromatic nitro  [-NO2] AND Aromatic-H AND Benzene by Bioaccumulation - metabolism alerts

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Alkyl substituent on aromatic ring OR Aromatic acid   [-C(=O)-OH] OR Aromatic alcohol  [-OH] OR Aromatic bromide   [-Br] OR Aromatic chloride   [-CL] OR Aromatic ether  [-O-aromatic carbon] OR Aromatic-CH2 OR Aromatic-CH3 OR Azo group   [-N=N-] OR Biphenyl OR -C=CH  [alkenyl hydrogen] OR Ketone   [-C-C(=O)-C-] OR Methyl  [-CH3] OR Naphthalene OR Number of fused 6-carbon aromatic rings OR Quaternary amine OR Sulfonic acid / salt -> aromatic attach OR Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Very fast by Bioaccumulation - metabolism half-lives ONLY

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as No alert found by Respiratory sensitisation

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Pro-Michael Addition OR Pro-Michael Addition >> Pro-quinone and related OR Pro-Michael Addition >> Pro-quinone and related >> Phenylenediamines by Respiratory sensitisation

Domain logical expression index: "q"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 108 Da

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 248 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
under test conditions no biodegradation observed
Conclusions:
The test chemical 4-nitrobenzene-1,3-diamine was estimated to be readily biodegradable in water.
Executive summary:

Biodegradability of 4-nitrobenzene-1,3-diamine (CAS no. 5131 -58 -8) is predicted using QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 0.85% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-nitrobenzene-1,3-diamine was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 4-nitrobenzene-1,3-diamine (CAS no. 5131 -58 -8) is predicted using QSAR toolbox version 3.4 with logKow as the primary descriptor (2017). Test substance undergoes 0.85% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4 -nitrobenzene-1,3 -diamine 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 -nitrobenzene-1,3 -diamine (CAS No. 5131 -58 -8) and various supporting weight of evidence studies for its closest 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 chemical 4 -nitrobenzene-1,3 -diamine (CAS No. 5131 -58 -8) was estimated.Test substance undergoes 0.85% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-nitrobenzene-1,3-diamine was 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 4 -nitrobenzene-1,3 -diamine (CAS No. 5131 -58 -8) 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 4-nitrobenzene-1,3 -diamine is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017),biodegradation screening test was conducted for 14 days (2 weeks) for evaluating the percentage biodegradability of the read across substance 4-nitroaniline (CAS no. 100 -01 -6). 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 read across substance was determined to be 0% by BOD and 2.9% by TOC removal parameter in 14 days. Thus, based on percentage degradation, substance 4-nitroaniline is considered to be not readily biodegradable in nature.

 

For the same read across chemical 4-nitroaniline (CAS no. 100 -01 -6), biodegradation test was conducted for 20 days for evaluating the percentage biodegradability of the read across substance 4-nitroaniline (P. PITTER, 1976). Activated sludge was used as a test inoculum. Activated sludge taken from a sewage plant is cultivated in a 1000ml volumetric cylinder. The mixture is aerated with pressure air. Every day 200 ml of the mixture is driven off so that the sludge age is 5 days. After driving off the 200ml of the mixture aeration is interrupted, and after sedimentation ca. 600mlof the liquid phase is driven off. The residue (200 ml of the thickened activated sludge) is diluted with tap water to the volume of ca.800 ml and 600 mg/l of starch or glucose, 600 mg/l of peptone, 25 ml of a phosphate buffer pH 7.2, and the solution of the tested compound are added. Then the mixture in the cylinder is made up to 1000ml with tap water and aerated for 23 h (the recirculation ratio is 0-25). After this period the procedure is repeated. The tested substance is dissolved in a beaker in a biological medium in a concentration corresponding to 200mg 1 -I COD. To the biological medium such amount of thickened adapted activated sludge is added to make dry matter of the inoculum 100mgl . The beaker is placed in a dark room with a roughly 3 constant temperature of 20 ± 3 °C on an electromagnetic stirrer. The initial value of COD or organic carbon of the liquid phase are determined. Samples filtered or centrifuged before analysis, are taken at suitable intervals. The decrease of the tested substance in the liquid phase is evaluated by determining COD or organic carbon. With the degree of degradation also the average specific rate of degradation is determined, expressed in terms of mg COD (or organic carbon) removed by a gramme of dry matter of the activated sludge per hour. The experiment is carried out till there is no decrease of COD. After that time the total percentage of COD removed and the rate of degradation are evaluated. Conc of test substance used for the study was 200mg/l, respectively. The percentage degradation of read across substance was determined to be 0% by COD parameter in 20 days. Thus, based on percentage degradation, substance 4-nitroaniline is considered to be not readily biodegradable in nature.

 

Another weight of evidence study of biodegradation from authoritative database (J-CHECK, 2017) of the read across substance 2,4-dinitroaniline (CAS no. 97 -02 -9) was conducted for 28 days. 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 read across substance was determined to be 4 and 3% degradation by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, substance 2,4-dinitroaniline is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical 4 -nitrobenzene-1,3 -diamine (from OECD QSAR toolbox version 3.4 and EPI Suite, 2017) and for its read across substance (from authoritative database J-CHECK, 2017 and peer reviewed journal), it can be concluded that the test substance 4 -nitrobenzene-1,3 -diamine can be expected to be not readily biodegradable in nature.