2-methoxy-5-nitroanilinium chloride

Short-term toxicity to aquatic invertebrates

Link to relevant study record(s)

Reference

Endpoint:

short-term toxicity to aquatic invertebrates

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:

Data is from OECD QSAR toolbox version.3.3 and QMRF report has been attached.

Qualifier:

according to guideline

Guideline:

other: Predicted data

Principles of method if other than guideline:

Prediction is done using QSAR Toolbox version 3.3 with log kow as the primary discriptors.

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

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Daphnia magna

Test type:

static

Water media type:

freshwater

Total exposure duration:

48 h

Key result

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

101.751 mg/L

Nominal / measured:

estimated

Conc. based on:

test mat.

Basis for effect:

mobility

Remarks on result:

other: not toxic

Details on results:

- Mortality of control: None

The prediction was based on dataset comprised from the following descriptors: EC50
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 ( not "g") )  )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and ("l" and ( not "m") )  )  and "n" )  and "o" )  and ("p" and ( not "q") )  )  and ("r" and ( not "s") )  )  and ("t" and ( not "u") )  )  and ("v" and ( not "w") )  )  and ("x" and ( not "y") )  )  and ("z" and "aa" )  )

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 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: "e"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

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: "g"

Referential boundary: The target chemical should be classified as SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Polynitroarenes OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> p-Substituted Mononitrobenzenes OR SN2 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 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: "i"

Referential boundary: The target chemical should be classified as SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroaniline Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "j"

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

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Non binder, MW>500 by Estrogen Receptor Binding

Domain logical expression index: "l"

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

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "n"

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: "o"

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

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Aromatic ether  [-O-aromatic carbon] AND Aromatic nitro  [-NO2] AND Aromatic-H AND Benzene AND Methyl  [-CH3] AND Quaternary amine by Bioaccumulation - metabolism alerts

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Azo group   [-N=N-] by Bioaccumulation - metabolism alerts

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Aromatic ether  [-O-aromatic carbon] AND Aromatic nitro  [-NO2] AND Aromatic-H AND Benzene AND Methyl  [-CH3] AND Quaternary amine by Bioaccumulation - metabolism alerts

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as Number of fused acyclic rings by Bioaccumulation - metabolism alerts

Domain logical expression index: "t"

Referential boundary: The target chemical should be classified as Aliphatic Amine, primary AND Ammonium salt AND Aryl AND Ether AND Nitrobenzene by Organic Functional groups

Domain logical expression index: "u"

Referential boundary: The target chemical should be classified as Fused carbocyclic aromatic by Organic Functional groups

Domain logical expression index: "v"

Referential boundary: The target chemical should be classified as Aliphatic Amine, primary AND Ether AND Nitrobenzene AND Overlapping groups by Organic Functional groups (nested)

Domain logical expression index: "w"

Referential boundary: The target chemical should be classified as Aromatic amine by Organic Functional groups (nested)

Domain logical expression index: "x"

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

Domain logical expression index: "y"

Referential boundary: The target chemical should be classified as Aryl chloride by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "z"

Parametric boundary:The target chemical should have a value of log Kow which is >= -3.99

Domain logical expression index: "aa"

Parametric boundary:The target chemical should have a value of log Kow which is <= 0.755

Conclusions:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9). EC50 mobility value was estimated to be 101.7508 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9) was likely to be not toxic to aquatic invertebrate.

Executive summary:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9). EC50 mobility value was estimated to be 101.7508 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9) was likely to be not toxic to aquatic invertebrate.

Description of key information

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9). EC50 mobility value was estimated to be 101.7508 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9) was likely to be not toxic to aquatic invertebrate.

Additional information

Following studies of target chemical and structurally similar read across includes predicted data and experimental data to conclude the toxicity extent of 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9) towards invertebrate is summarized as follows:

Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the closest read across substances, the toxicity to aquatic invertebrate was predicted 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9). EC50 mobility value was estimated to be 101.7508 mg/l for Daphnia magna for 48 hrs duration. It was concluded that 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9) was likely to be not toxic to aquatic invertebrate.

The above predicted data of target chemical is supported by the experimental study of structurally similar read across 3 – Nitrobenzene sulfonic acid (CAS No. 127-68-4) from the experimental ABITEC lab report 2016, suggests that the Determination of the inhibition of the mobility of daphnids was carried out with the substance 3 – Nitrobenzene sulfonic acid according to OECD Guideline 202. The test substance was tested at the limit concentration 100 mg/l. Effects on immobilisation were observed for 48 hours. Based on the % inhibition of daphnia magna, due to the exposure of chemical 3 – Nitrobenzene sulfonic acid, the IC8 was 100 mg/l.

This value indicates that the substance is likely to be non-hazardous to aquatic invertebrates and cannot be classified as toxic as per the CLP criteria.

Another supporting experimental study for the structurally similar read across Sulfanilic acid (121-57-3) from the publication Water Pollution Control Federation 1965, also suggests that the Short term toxicity of test chemical sodium 4-chloro-3-nitrobenzene-1-sulfonate was determined in Daphnia magna which were cultured in laboratory from starting culture originally obtained from Put in Bay, Ohio. The experiment was static test and medium used was glasswool filtered university lake water. Median tolerance limit(TLm) of test chemical sodium 4-chloro-3-nitrobenzene-1-sulfonate was observed in daphnia magna at different time intervals. At 24 hrs and 48 hrs it was 8665 mg/L and at 72 hrs TLm was 6017 mg/L on the basis of immobilization. On the basis of TLm value at different time interval it is concluded that this test chemical is considered as "not classified" according to CLP criteria.

Thus based on the effect concentrations which is in the range 100 mg/l to 8665 mg/l give the conclusion that test substance 2-methoxy-5-nitroanilinium chloride (CAS: 67827-72-9) was likely to be not toxic to aquatic invertebrate at environmentally relevant concentrations and can be considered to be “not classified” as per the CLP classification criteria.