2-methoxy-5-nitroanilinium chloride

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 prediction was done by using OECD QSAR tool box v3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: 2-methoxy-5-nitroanilinium chloride
- IUPAC name: 2-methoxy-5-nitroanilinium chloride
- Molecular formula: C7H9ClN2O3
- Molecular weight: 204.6121g/mol
- Smiles: Cl.COc1ccc(cc1N)[N+](=O)[O-]
- Inchl: 1S/C7H8N2O3.ClH/c1-12-7-3-2-5(9(10)11)4-6(7)8;/h2-4H,8H2,1H3;1H
- Substance type: Organic

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: % degradation by BOD

Value:

0.2

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent degradation of test chemical 2-methoxy-5-nitroanilinium chloride was determined to be 0.20% on the basis of BOD as parameter 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" )  and ("d" and ( not "e") )  )  and "f" )  and "g" )  and "h" )  and ("i" and ( not "j") )  )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and ("o" and "p" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids AND SN1 AND SN1 >> Nucleophilic attack after reduction and nitrenium ion formation AND SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids by DNA binding by OASIS v.1.3

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Aromatic nitro by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Strong binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as No alert found by Protein binding by OASIS v1.3

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Ester aminolysis OR Acylation >> Ester aminolysis >> Amides OR Michael Addition OR Michael Addition >> Quinoide type compounds OR Michael Addition >> Quinoide type compounds >> Quinone methide(s)/imines; Quinoide oxime structure; Nitroquinones, Naphthoquinone(s)/imines  OR SN2 OR SN2 >> Nucleophilic substitution at sp3 carbon atom OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> (Thio)Phosphates  OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> Alkyl halides  OR SN2 >> Nucleophilic substitution on benzilyc carbon atom OR SN2 >> Nucleophilic substitution on benzilyc carbon atom >> alpha-Activated benzyls  OR SNAr OR SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds OR SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds >> Activated aryl and heteroaryl compounds by Protein binding by OASIS v1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Class 5 (Not possible to classify according to these rules) by Acute aquatic toxicity classification by Verhaar (Modified) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Reactive unspecified by Acute aquatic toxicity MOA by OASIS ONLY

Domain logical expression index: "h"

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

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Alkali Earth by Groups of elements

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 15 - Nitrogen N AND Group 16 - Oxygen O AND Group 17 - Halogens Cl AND Group 17 - Halogens F,Cl,Br,I,At by Chemical elements

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Group 16 - Sulfur S by Chemical elements

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Anilines (Hemolytic anemia with methemoglobinemia) Rank A AND Anilines (Hepatotoxicity) Rank C by Repeated dose (HESS)

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Dantrolene (Hepatotoxicity) Alert by Repeated dose (HESS)

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 182 Da

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 223 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

Percent degradation of test chemical 2-methoxy-5-nitroanilinium chloride was determined to be 0.20% by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it can be concluded that test chemical 2-methoxy-5-nitroanilinium chloride is not readily biodegradable.

Executive summary:

Biodegradability of test chemical 2-methoxy-5-nitroanilinium chloride was determined by uisng OECD QSAR tool box v3.3 by cosidering five closest read across chemicals with log Kow as primary descriptor. Percent degradation of test chemical 2-methoxy-5-nitroanilinium chloride was determined to be 0.20% by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it can be concluded that  test chemical 2-methoxy-5-nitroanilinium chloride is not readily biodegradable.

Description of key information

Biodegradability of test chemical 2-methoxy-5-nitroanilinium chloride was determined by uisng OECD QSAR tool box v3.3 by cosidering five closest read across chemicals with log Kow as primary descriptor. Percent degradation of test chemical 2-methoxy-5-nitroanilinium chloride was determined to be 0.20% by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it can be concluded that  test chemical 2-methoxy-5-nitroanilinium chloride is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data for the target compound 2-methoxy-5-nitroanilinium chloride(CAS No. 67827-72-9) 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 first weight of evidence study the biodegradability of test chemical 2-methoxy-5-nitroanilinium chloride was determined by using OECD QSAR tool box v3.3 by considering five closest read across chemicals with log Kow as primary descriptor. Percent degradation of test chemical 2-methoxy-5-nitroanilinium chloride was determined to be 0.20% by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent biodegradability value it can be concluded that test chemical 2-methoxy-5-nitroanilinium chloride is not readily biodegradable.

 

Next weight of evidence study was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound 2-methoxy-5-nitroanilinium chloride (CAS no. 67827 -72 -9) 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 Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 2-methoxy-5-nitroanilinium chloride is expected to be not readily biodegradable.

 

Another experimental weight of evidence study was done from journal “The Science of the Total Environment “ 170 (1995) 43-51 by Takashi Kameya, Takeshi Murayamaa, Kohei Uranoa, Masaru Kitanob for structurally similar read across chemical 3- nitrobenzoic acid of CAS no.121-92-6 in this study the read across chemical 3- nitrobenzoic acid was tested for biodegradation at 30 mgC/l concentration by analyzing the decrease of DOC taking benzoic acid as a reference ( standard) compound using inoculum obtained from synthetic sewage at concentration of 100 mgC/l using JIS BOD5 inorganic medium for 28 days in anaerobic condition less than 30% biodegradation ratio was obtained. Then read across compound 3- nitrobenzoic acid was tested at low (3mgC/l) concentration by analyzing decrease of chromatographic peak (test material analysis) using same inoculum and medium in anaerobic condition it showed < 30% biodegradation. So it is concluded that read across item was not readily biodegradable.

Next weight of evidence study was done from journal “Applied and Environmental Microbiology”, Feb. 1989, Vol. 55, No. 2 p. 433-439 by Nigel S. Battersby and Valerie Wilson for structurally similar read across chemical in this study the Biodegradation potential of read across chemical 3-Nitrobenzoic acid (CAS no.121-92-6) was analysed under methanogenic conditions with an anaerobic digesting sludge as inoculums. The read across chemical was taken at concentration 50 mg/L in a serum bottle containing 90% nitrogen and 10 % carbon dioxide in head space to maintain anaerobic condition at temperature 35 oC then gas production was measured weekly for more than 80 days with the help of hand held pressure meter. The theoretical gas production was corrected with the blank. The read across chemical 3-nitrobenzoic acid undergoes 0 % degradation in anaerobic condition in more than 80 days. So it is concluded that this read across chemical is not readily biodegradable.

Another experimental weight of evidence study was done from authoritative database (J CHECK, 2017) in this study the Biodegradation experiment was carried out for read across chemical 4-Nitrophenol (CAS no. 100-02-7)by taking activated sludge as inoculums at 30 mg/L concentration for 14 days. Biodegradation was analyzed by using three parameters namely O2 consumption (BOD), TOC removal and test material analysis by GC. The initial concentration of read across chemical was 100 mg/L. After 14 days of incubation Percent biodegradation of read across chemical 4-Nitrophenol was observed to be < 4.3 % by O2 consumption (BOD) parameter <0.0 % by TOC removal and test material analysis by GC parameters in 14 days. Therefore it is concluded that read across chemical 4-Nitrophenol is not readily biodegradable.

 

Last experimental weight of evidence study was done from authoritative database (J CHECK, 2017) in this study the biodegradation experiment was carried out of read across chemical 2-Nitro-p-cresol (CAS no. 119-33-5) by taking activated sludge as inoculums at 30 mg/L concentration for 14 days. Biodegradation was analyzed by using two parameters namely BOD and HPLC. The initial concentration of read across chemical was 100 mg/L. The study design used was of standard type. After 14 days of incubation percent biodegradation of read across chemical 2-Nitro-p-cresol was observed to be 0.0 % by BOD parameter 2.0% by GC parameter. On the basis of percent degradability values it is concluded that read across chemical 2-Nitro-p-cresol is not readily biodegradable.

 

 

On the basis of results of above mentioned studies for target chemical 2-methoxy-5-nitroanilinium chloride (CAS no. 67827 -72 -9) ( from OECD QSAR tool boxv3.3 and EPI suite) and supporting weight of evidence study ( from JournalsThe Science of the Total Environment , Applied and Environmental Microbiology and J Check, 2017). It is concluded that the test chemical 2-methoxy-5-nitroanilinium chloridecan be expected to be not readily biodegradable.