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Short-term toxicity to aquatic invertebrates

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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.
Reference:
Composition 0
Qualifier:
according to
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
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material: 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid
- IUPAC name: 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid
- Molecular formula: C60H40Cl2N14O26S8
- Molecular weight: 1700.482 g/mole
- Smiles c1ccc2c(c1)ccc(c2S(=O)(=O)O)/N=N/c3c(cc4cc(cc(c4c3O)Nc5nc(nc(n5)Cl)Nc6ccc(c(c6)S(=O)(=O)O)/C=C/c7c(cccc7S(=O)(=O)O)Nc8nc (nc(n8)Cl)Nc9cc(cc1c9c(c(c(c1)S(=O)(=O)O)/N=N/c1ccc2ccccc2c1S(=O)(=O)O)O)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O
- Inchl: 1S/C60H40Cl2N14O26S8/c61-55-67-57(71-59(69-55)65-41-25-33(103(79,80)81)20-30-22-45(107(91,92)93)49(51(77)47(30)41)75-73-39-18-14-27-6-1-3-8-35(27)53(39)109(97,98)99)63-32-16-12-29(44(24-32)106(88,89)90)13-17-37-38(10-5-11-43(37)105(85,86)87)64-58-68-56(62)70-60(72-58)66-42-26-34(104(82,83)84)21-31-23-46(108(94,95)96)50(52(78)48(31)42)76-74-40-19-15-28-7-2-4-9-36(28)54(40)110(100,101)102/h1-26,77-78H,(H,79,80,81)(H,82,83,84)(H,85,86,87)(H,88,89,90)(H,91,92,93)(H,94,95,96)(H,97,98,99)(H,100,101,102)(H2,63,65,67,69,71)(H2,64,66,68,70,72)/b17-13+,75-73+,76-74+
- Substance type: Organic
- Physical state: Solid
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.:
108.446 mg/L
Nominal / measured:
estimated
Conc. based on:
test mat.
Basis for effect:
other: Intoxication
Remarks on result:
other: not toxic

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" or "d" )  and ("e" and ( not "f") )  )  and "g" )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and ("l" and ( not "m") )  )  and ("n" and ( not "o") )  )  and ("p" and ( not "q") )  )  and ("r" and ( not "s") )  )  and ("t" and ( not "u") )  )  and ("v" and ( not "w") )  )  and ("x" and "y" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Aromatic compound OR Azo compound OR Halogen derivative OR Hydroxy compound OR Phenol OR Sulfonic acid OR Sulfonic acid derivative by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] OR Aliphatic Nitrogen, one aromatic attach [-N] OR Aliphatic Nitrogen, two aromatic attach [-N-] OR Amino Triazine/Pyrazine/Pyrimidine  OR Aromatic Carbon [C] OR Aromatic Nitrogen OR Azo [-N=N-] OR Chlorine, aromatic attach [-Cl] OR Chlorine, olefinic attach [-Cl] OR Hydroxy, aromatic attach [-OH] OR Hydroxy, sulfur attach [-OH] OR Miscellaneous sulfide (=S) or oxide (=O) OR Nitrogen, two or tree olefinic attach [>N-] OR Olefinic carbon [=CH- or =C<] OR Oxygen, one aromatic attach [-O-] OR Suflur {v+4} or {v+6} OR Sulfinic acid [-S(=O)OH] OR Sulfonate, aromatic attach [-SO2-O] OR Sym-Triazine ring  by Organic functional groups (US EPA) ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Alkene OR Aromatic amine OR Aromatic heterocyclic halide OR Aryl OR Aryl halide OR Azo OR Fused carbocyclic aromatic OR Overlapping groups OR Phenol OR Sulfonic acid by Organic Functional groups (nested) ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Alkene OR Aromatic amine OR Aromatic heterocyclic halide OR Aryl OR Aryl halide OR Azo OR Fused carbocyclic aromatic OR Naphtalene OR Phenol OR Sulfonic acid OR Triazine by Organic Functional groups ONLY

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 >> Quinones and Trihydroxybenzenes OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds >> Alpha, Beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> Alpha, Beta-Unsaturated Aldehydes OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Haloalkenes with Electron-Withdrawing Groups OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Organic Azides OR Non-covalent interaction >> DNA intercalation >> Polycyclic Aromatic Hydrocarbon and Naphthalenediimide Derivatives OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes OR Radical OR Radical >> Radical mechanism by ROS formation OR Radical >> Radical mechanism by ROS formation >> Organic Azides OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Aminobiphenyl Analogs 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 SN1 OR SN1 >> Alkylation after metabolically formed carbenium ion species OR SN1 >> Alkylation after metabolically formed carbenium ion species >> Polycyclic Aromatic Hydrocarbon and Naphthalenediimide Derivatives OR SN1 >> Nucleophilic attack after nitrene formation OR SN1 >> Nucleophilic attack after nitrene formation >> Organic Azides OR SN1 >> Nucleophilic attack after nitrenium ion formation OR SN1 >> Nucleophilic attack after nitrenium ion formation >> p-Aminobiphenyl Analogs OR SN1 >> Nucleophilic attack after nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN2 OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Haloalkenes with Electron-Withdrawing Groups OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Polycyclic Aromatic Hydrocarbon and Naphthalenediimide Derivatives OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Sulfonates and Sulfates OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives by DNA binding by OASIS v.1.4

Domain logical expression index: "g"

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: "h"

Referential boundary: The target chemical should be classified as Not classified by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Neutral Organics by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Not classified by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Not Related to an Existing ECOSAR Class by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Not classified by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Phenols, Poly by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "n"

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

Domain logical expression index: "o"

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

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Alkene AND Aromatic amine AND Aromatic heterocyclic halide AND Aryl AND Aryl halide AND Azo AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfonic acid AND Triazine by Organic Functional groups

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Cycloalkane by Organic Functional groups

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Aromatic compound AND Azo compound AND Halogen derivative AND Hydroxy compound AND Phenol AND Sulfonic acid AND Sulfonic acid derivative by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "s"

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

Domain logical expression index: "t"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] AND Aliphatic Nitrogen, one aromatic attach [-N] AND Aliphatic Nitrogen, two aromatic attach [-N-] AND Amino Triazine/Pyrazine/Pyrimidine  AND Aromatic Carbon [C] AND Aromatic Nitrogen AND Azo [-N=N-] AND Chlorine, aromatic attach [-Cl] AND Chlorine, olefinic attach [-Cl] AND Hydroxy, aromatic attach [-OH] AND Hydroxy, sulfur attach [-OH] AND Miscellaneous sulfide (=S) or oxide (=O) AND Nitrogen, two or tree olefinic attach [>N-] AND Olefinic carbon [=CH- or =C<] AND Oxygen, one aromatic attach [-O-] AND Suflur {v+4} or {v+6} AND Sulfinic acid [-S(=O)OH] AND Sulfonate, aromatic attach [-SO2-O] AND Sym-Triazine ring  by Organic functional groups (US EPA)

Domain logical expression index: "u"

Referential boundary: The target chemical should be classified as Pyridine, non fused rings  by Organic functional groups (US EPA)

Domain logical expression index: "v"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] AND Aliphatic Nitrogen, one aromatic attach [-N] AND Aliphatic Nitrogen, two aromatic attach [-N-] AND Amino Triazine/Pyrazine/Pyrimidine  AND Aromatic Carbon [C] AND Aromatic Nitrogen AND Azo [-N=N-] AND Chlorine, aromatic attach [-Cl] AND Chlorine, olefinic attach [-Cl] AND Hydroxy, aromatic attach [-OH] AND Hydroxy, sulfur attach [-OH] AND Miscellaneous sulfide (=S) or oxide (=O) AND Nitrogen, two or tree olefinic attach [>N-] AND Olefinic carbon [=CH- or =C<] AND Oxygen, one aromatic attach [-O-] AND Suflur {v+4} or {v+6} AND Sulfinic acid [-S(=O)OH] AND Sulfonate, aromatic attach [-SO2-O] AND Sym-Triazine ring  by Organic functional groups (US EPA)

Domain logical expression index: "w"

Referential boundary: The target chemical should be classified as Halogen, nitrogen attach by Organic functional groups (US EPA)

Domain logical expression index: "x"

Parametric boundary:The target chemical should have a value of log BCF max which is >= 2.67 log(L/kg wet)

Domain logical expression index: "y"

Parametric boundary:The target chemical should have a value of log BCF max which is <= 3.63 log(L/kg wet)

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 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2). EC50 Intoxication value was estimated to be 108.4461 mg/l for Daphnia magna for 48.0 hrs duration. It was concluded that 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2) 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 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2). EC50 Intoxication value was estimated to be 108.4461 mg/l for Daphnia magna for 48.0 hrs duration. It was concluded that 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2) 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 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2). EC50 Intoxication value was estimated to be 108.4461 mg/l for Daphnia magna for 48.0 hrs duration. It was concluded that 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2) was likely to be not toxic to aquatic invertebrate.

Key value for chemical safety assessment

EC50/LC50 for freshwater invertebrates:
108.446 mg/L

Additional information

Following studies of target chemical and structurally similar read across includes predicted data and experimental data to conclude the toxicity extent of 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2) towards aquatic 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 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2). EC50 Intoxication value was estimated to be 108.4461 mg/l for Daphnia magna for 48.0 hrs duration. It was concluded that 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2) 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 trisodium 5-({4-chloro-6-[ethyl(phenyl)amino]-1,3,5-triazin-2-yl}amino)-4-hydroxy-3-[(1-sulfonato-2-naphthyl)diazenyl]naphthalene-2,7-disulfonate (Cas no. 84045-65-8) from the experimental ABITEC Lab report 2017, suggests that the Experimental study for inhibition of the mobility of daphnids was carried out with the trisodium 5-({4-chloro-6-[ethyl(phenyl)amino]-1,3,5-triazin-2-yl}amino)-4-hydroxy-3-[(1-sulfonato-2-naphthyl)diazenyl]naphthalene-2,7-disulfonate according to OECD Guideline 202 (Report no. 174/17, Abitec 2017). The animals used for the test shall be less than 24 h old and should not be of first brood progeny. Test solutions of required concentration were prepared by mixing the stock solution of the test sample with reconstituted test water. The test substance was tested at the concentration of 0,30,45,67,100 and 150 mg/l. The test was performed under static conditions in fresh water system at 20±1°C temperature. Effects on immobilisation were observed for 48 hours. EC50 was calculated using non linear regression by the software Prism 4.0.The median effective concentration (EC50) for the test substance trisodium 5-({4-chloro-6-[ethyl(phenyl)amino]-1,3,5-triazin-2-yl}amino)-4-hydroxy-3-[(1-sulfonato-2-naphthyl)diazenyl]naphthalene-2,7-disulfonate (Cas no. 84045-65-8) in Daphnia magna was determined to be 103.8 mg/L for immobilisation effects.

Based on the value trisodium 5-({4-chloro-6-[ethyl(phenyl)amino]-1,3,5-triazin-2-yl}amino)-4-hydroxy-3-[(1-sulfonato-2-naphthyl)diazenyl]naphthalene-2,7-disulfonate was considered to be non toxic to aquatic invertebrates and thus "not classified" as per the CLP regulation.

Another supporting experimental study for the structurally similar read across suramin (CAS: 145-63-1) from the secondary source 1993, also suggests As in vitro experiment was performed on 8 Gyrodactvlus (worm) were taken from fish and placed in petri dish with added suramin and observed for 30 and 60 min after exposing to the suramin. A control trial was also used were zero mortality observed. After exposure period only 1 worm death was observed.On the basis of this, the LD 50 value for aquatic invertebrates for suramin (145-63-1) was determined to be greater than 200 mg/l as 1 worm was died out of 8 used for experiment. Based on the result , the suramin was considered as "not classified" according to CLP regulations.

Thus based on the effect concentrations which is in the range 103.8 mg/L to200 mg/lgive the conclusion that test substance 4,4'-[vinylenebis[(3-sulpho-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]]bis[5-hydroxy-6-[(1-sulpho-2-naphthyl)azo] naphthalene-2,7-disulphonic] acid (CAS: 94022-69-2) is likely to be not toxic to aquatic environment at environmentally relevant concentrations and applying weight of evidence approach it can be considered to be “not classified” as per the CLP classification criteria.