3'-nitroacetophenone

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: ready biodegradability

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 B (Ready Biodegradability: CO2 Evolution Test)

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 (as cited in study report): 3-Nitroacetophenone
- Molecular formula (if other than submission substance): C8H7NO3
- Molecular weight (if other than submission substance): 165.147 g/mol
- Smiles notation (if other than submission substance): c1(cc(ccc1)[N+](=O)[O-])C(C)=O
- InChI: 1S/C8H7NO3/c1-6(10)7-3-2-4-8(5-7)9(11)12/h2-5H,1H3
- 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:

CO2 evolution

Key result

Parameter:

% degradation (CO2 evolution)

Value:

22.75

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 22.75% degradation by CO2 evolution in 28 days.

The prediction was based on dataset comprised from the following descriptors: "CO2 evolution"
Estimation method: Takes average value from the 5 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

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

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Aryl AND Ketone AND Nitrobenzene by Organic Functional groups

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Ketone 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 Carbon [CH] AND Aliphatic Carbon [-CH2-] AND Aliphatic Carbon [-CH3] AND Aromatic Carbon [C] AND Carbonyl, aliphatic attach [-C(=O)-] AND Carbonyl, olefinic attach [-C(=O)-] AND Carbonyl, one aromatic attach [-C(=O)-] 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 Aromatic compound AND Carbonyl compound AND Ketone AND Nitro compound by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Acridone, Thioxanthone, Xanthone and Phenazine Derivatives OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain 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 by ROS formation OR Radical >> Radical mechanism by ROS formation >> Acridone, Thioxanthone, Xanthone and Phenazine Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Hydrazine Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroarenes with Other Active Groups OR SN1 OR SN1 >> Carbenium ion formation OR SN1 >> Carbenium ion formation >> Alpha-Haloethers 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 reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroarenes with Other Active Groups OR SN2 OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Sulfonates and Sulfates OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> SN2 at sp3-carbon atom OR SN2 >> SN2 at sp3-carbon atom >> Alpha-Haloethers 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.1.3

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules by DPRA Cysteine peptide depletion

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Low reactive OR Low reactive >> Alicyclic ketones by DPRA Cysteine peptide depletion

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Non-Metals by Groups of elements

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Halogens OR Metalloids by Groups of elements

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 148 Da

Domain logical expression index: "p"

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

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical 3-Nitroacetophenone was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 3-Nitroacetophenone (CAS no. 121 -89 -1) is predicted using QSAR toolbox version 3.4. Test substance undergoes 22.75% degradation by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, the test chemical 3-Nitroacetophenone was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 3-Nitroacetophenone (CAS no. 121 -89 -1) is predicted using QSAR toolbox version 3.4 (2017). Test substance undergoes 22.75% degradation by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, the test chemical 3-Nitroacetophenone 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

In different studies, 3 -Nitroacetophenone (CAS No. 121 -89 -1) has been investigated for potential for biodegradation to a greater or lesser extent. These include 2 predicted data for the target compound 3 -Nitroacetophenone and the 6 studies (from peer reviewed journal, authoritative database and secondary source) for its closest read across substances with logKow as the primary descriptor.

 

Prediction of the biodegradability of test substance 3-Nitroacetophenone (CAS no. 121 -89 -1) was done by SSS (2017) using OECD QSAR toolbox version 3.4with logKow as the primary descriptor(2017). Test substance undergoes 22.75% degradation by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, the test chemical 3-Nitroacetophenone was estimated to be not readily biodegradable in water.

 

Another prediction was done using the Estimation Programs Interface Suite (EPI suite, 2017) for estimating the biodegradation potential of the test compound 3-Nitroacetophenone (CAS no. 121 -89 -1) 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 as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that 3-Nitroacetophenone is expected to be not readily biodegradable.

 

In a weight of evidence study of read across substance 3-Nitrobenzoic acid (CAS no. 121-92-6) which is having a percentage similarity of 80-90% with the target chemical 3-Nitroacetophenone (J-CHECK, 2016), biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 3-Nitrobenzoic acid (CAS no. 121-92-6). 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 6, 0 and 3% by BOD, TOC removal and UV-Vis parameter in 14 days. Thus, based on percentage degradation, 3-Nitrobenzoic acid is considered to be not readily biodegradable in nature.

 

For the same read across substance 3-Nitrobenzoic acid (CAS no. 121-92-6) which is having a percentage similarity of 80-90% with the target chemical 3-Nitroacetophenone, biodegradation experiment was conducted by Takashi Kameya, et. al; 1995; for 28 days for evaluating the percentage biodegradability of read across substance 3 -Nitrobenzoic acid (CAS no. 121-92-6). Seeding bacteria was used as a test inoculum. The seeding bacteria had been cultured in a continuous anaerobic bioreactor at 37 + 1°C.Synthetic sewage, composed of glucose, peptone and corn steap liquor (carbon ratio = 1:1:2), is supplied into the reactor (3.0 g-C/l, 8.0 g-CS./.d). In this culture, > 95% acidic decomposition and > 90% methanogenic decomposition are achieved.

A standard test and low conc. tests using 50 ml vials (total capacity: 68 ml) was employed. Ten test vials were prepared under the same conditions, and they were set in a water bath at 37°C ± 0.5”C. The original solution was added to the test inoculum and organic medium in oxygen-free water. At the starting time and after every week, two vials were opened simultaneously, and the concentration of organic compound was analyzed. The concentration of organic compound was determined by dissolved organic carbon (DOC) in the standard test and by chromatography in low conc. test. Biodegradation ratio is determined by analysing the decrease of DOC in the standard test. The percentage degradation of the read across compound was determined to be < 30% degradation by DOC removal, chromatography in 28 days by using standard test Thus, based on the percentage degradation, the read across chemical 3-Nitrobenzoic acid was considered to be not readily biodegradable in nature.

 

In a weight of evidence study (J-CHECK, 2016) of another read across substance Tripropylene glycol (CAS no. 24800-44-0), biodegradation was conducted for 28 days for evaluating the percentage biodegradability of read across substance Tripropylene glycol (CAS no. 24800-44-0). 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 2, 0 and 2% by BOD, TOC removal and GC parameter in 28 days. Thus, based on percentage degradation, Tripropylene glycol is considered to be not readily biodegradable in nature.

 

Another weight of evidence study (HSDB, 2016) of biodegradation was conducted for 20 days for evaluating the percentage biodegradability of read across substance Dipropylene glycol monomethyl ether (CAS no. 34590-94-8). The percentage degradation of read across substance was determined to 0, 0 and 31% degradation by ThOD parameter in 5, 10 and 20 days, respectively. Thus, based on percentage degradation, Dipropylene glycol monomethyl ether was considered to be not readily biodegradable in nature.

 

Weight of evidence study (OECD SIDS, 2001) of biodegradation for read across substance Dipropylene glycol monomethyl ether (CAS no. 34590-94-8) was conducted for 28 days for evaluating the percentage biodegradability of chemical Dipropylene glycol monomethyl ether. Initial test substance conc. used in the study was10 mg/l, respectively. The percentage degradation of read across substance was determined to be 34% degradation in 28 days. At a concentration of 20 mg/l degradation was <10% after 28 days. Thus, based on percentage degradation, Dipropylene glycol monomethyl ether was considered to be not readily biodegradable in nature.

 

In an additional weight of evidence study (OECD SIDS, 2003), biodegradation was conducted for 28 days for evaluating the percentage biodegradability of read across substance Dipropylene glycol monobutyl ether (CAS no. 29911-28-2). The study was performed according to OECD Guideline 301 D (Ready Biodegradability: Closed Bottle Test). Initial test substance conc. used in the study was 0, 1.86, or 9.29 mg/l, respectively. Domestic sewage was used as a test inoculum collected from a local municipal sewage treatment facility. To test for its ready biodegradability potential, read across chemical was incubated for 28 days in continuously agitated closed bottles in the dark at two concentrations with inoculum (secondary effluent) collected from a local municipal sewage treatment facility. The incubation temperature of the water was 19.7-20.0°C, pH ranged from 7.2 to 7.4, hardness was not reported, and the concentration of inoculum was one droplet per liter of test solution. Oxygen concentration was the measured variable. Degradation of read across chemical was monitored by assessing the dissipation of oxygen in the test solution over time (i.e., measuring dissolved oxygen content with an oxygen electrode at various time points). Oxygen content was measured (in duplicate bottles) on days 0, 5, 15, and 28. Degradation was calculated by dividing the biochemical oxygen demand (BOD) expressed as mg O2 per mg DPnB, by the theoretical oxygen demand (ThOD).The percentage degradation of read across substance was determined to be 0% by %ThOD parameter in 28 days. Thus, based on percentage degradation, Dipropylene glycol monobutyl ether was considered to be not readily biodegradable in water.

 

On the basis of above results for target and read across substance, it can be concluded that the test substance 3 -Nitroacetophenone can be expected to be not readily biodegradable in nature.