Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate

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:

QMRF report has been attached

Qualifier:

according to guideline

Guideline:

other: Estimated data

Principles of method if other than guideline:

Prediction was done using the OECD QSAR toolbox version 3.4.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name: Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate
- Mol. formula: C17H10ClF3N3NaO4S
- Molecular Weight: 467.786 g/mole
- SMILES:Nc1ccc2cc(S(=O)(=O)O{-}.[Na]{+})cc(O)c2c1N=Nc1ccc(Cl)cc1C(F)(F)F
- InChI:1S/C17H11ClF3N3O4S.Na/c18-9-2-4-13(11(6-9)17(19,20)21)23-24-16-12(22)3-1-8-5-10(29(26,27)28)7-14(25)15(8)16;/h1-7,25H,22H2,(H,26,27,28);/q;+1/p-1/b24-23-;

Analytical monitoring:

not specified

Vehicle:

not specified

Test organisms (species):

Daphnia magna

Details on test organisms:

- Common name: Water flea

Test type:

static

Water media type:

freshwater

Total exposure duration:

48 h

Nominal and measured concentrations:

Estimated data

Reference substance (positive control):

not specified

Key result

Duration:

48 h

Dose descriptor:

EC50

Effect conc.:

170.384 mg/L

Nominal / measured:

estimated

Conc. based on:

not specified

Basis for effect:

other: Intoxication

Remarks on result:

other: Other details not known

Details on results:

The effect concentration was 170 mg/l

The prediction was based on dataset comprised from the following descriptors: EC50
Estimation method: Takes average value from the 6 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

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: "b"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Schiff base formation by aldehyde formed after metabolic activation AND AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives AND Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines AND Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines AND Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives AND SN1 AND SN1 >> Nucleophilic attack after metabolic nitrenium ion formation AND SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines AND SN2 AND SN2 >> Acylation involving a leaving group after metabolic activation AND SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives AND SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation AND SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives by DNA binding by OASIS v.1.4

Domain logical expression index: "c"

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

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acid moiety AND Anilines (Unhindered) AND Phenol Amines AND Phenols AND Salt by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "e"

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

Domain logical expression index: "f"

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

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as No alert found OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Hydrazine OR SN1 >> Nitrenium Ion formation >> Aromatic nitro by DNA binding by OECD

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Moderate binder, NH2 group OR Weak binder, NH2 group OR Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "k"

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: "l"

Referential boundary: The target chemical should be classified as SR reaction (peroxidase-activated heterocyclic amines) by Protein binding by OASIS v1.4

Domain logical expression index: "m"

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: "n"

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

Domain logical expression index: "o"

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

Domain logical expression index: "p"

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

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Alkyl halide AND Aniline AND Aryl AND Aryl halide AND Azo AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfonic acid by Organic Functional groups

Domain logical expression index: "r"

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

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as Alkyl halide AND Aniline AND Aryl AND Aryl halide AND Azo AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfonic acid by Organic Functional groups

Domain logical expression index: "t"

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

Domain logical expression index: "u"

Referential boundary: The target chemical should be classified as Alkyl halide AND Aniline AND Aryl AND Aryl halide AND Azo AND Fused carbocyclic aromatic AND Naphtalene AND Phenol AND Sulfonic acid by Organic Functional groups

Domain logical expression index: "v"

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

Domain logical expression index: "w"

Parametric boundary:The target chemical should have a value of log Kow which is >= -0.284

Domain logical expression index: "x"

Parametric boundary:The target chemical should have a value of log Kow which is <= 3.53

Validity criteria fulfilled:

not specified

Conclusions:

Based on the intoxication of test organism the EC50 value was estimated to be 170 mg/l when Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate exposed to daphnia magna for 48 hrs.     
   

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 five closest read across substances, toxicity on daphnia magna was predicted for Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate (57741-47-6). Based on the intoxication of test organism the EC50 value was estimated to be 170 mg/l when Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate exposed to daphnia magna for 48 hrs.         

Based on this value it can be concluded that the substance Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate is considered to be nontoxic to aquatic environment and cannot classified as per the criteria mentioned in CLP regulation.        

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 five closest read across substances, toxicity on daphnia magna was predicted for Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate (57741-47-6). Based on the intoxication of test organism the EC50 value was estimated to be 170 mg/l when Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate exposed to daphnia magna for 48 hrs.        

Based on this value it can be concluded that the substance Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonateis considered to be nontoxic to aquatic environment and cannot classified as per the criteria mentioned in CLP regulation.        

Key value for chemical safety assessment

Fresh water invertebrates

Fresh water invertebrates

Effect concentration:

170 mg/L

Additional information

Based on the various prediction data for the target chemical and experimental data for the read across chemical study have been reviewed to determine the toxic nature of Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate (57741-47-6) on the growth of invertebrates. The studies are as mentioned below: 

In the first predicted study for the target chemical Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl) phenyl]azo]-4-hydroxynaphthalene-2-sulphonate (57741-47-6) from QSAR toolbox 2017, study was carried out. Based on the prediction done using the OECD QSAR toolbox version 3.3 with log kow as the primary descriptor and considering the five closest read across substances, toxicity on daphnia magna was predicted for Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate (57741-47-6). Based on the intoxication of test organism the EC50 value was estimated to be 170 mg/l when Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate exposed to daphnia magna for 48 hrs.         

Based on this value it can be concluded that the substance Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate is considered to be nontoxic to aquatic environment and cannot classified as per the criteria mentioned in CLP regulation.        

 

First predicted study was supported by the other experimental study for the read across chemical (3734-67-6) from ABITEC lab report. An acute immobilisation test was used to test how a range of concentrations of Disodium 5-acetylamino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate exerts different degrees of toxic effects on the swimming capability of Daphnia magna under otherwise identical test conditions. The test was performed in close resemblance to OECD guideline 202 by ABITEC in Prague. The testing aim was to determine a EC50 after 48 hours of exposure to D. magna. Daphnids were exposed to Disodium 5-acetylamino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate in 50 ml beakers in a volume of 25 ml of liquid solution containing both the chemical and media as specified in OECD 202. The beakers were placed in a temperature controlled room at 20±1 degrees Celsius. The D. magna (age ≤24) used for the test had been breed at ABITEC. The breeding stock of D. Magna originated from University of Technology in Prague. The animals were exposed to medium (i.e. a beaker containing only medium) and/or the tested chemical during 48 hours (±1 hour). None of the exposed animal’s immobilization were affected by exposure to only medium. The nominal concentrations used were: 100 mg/L (limit test). There were 5 Daphnia per test vessels and 5 replicates per concentration. The pH in test vessels were 7.7-7.8 mg/L. The positive control/reference substance used in the tested showed an expected result and gave an EC50 that corresponded to previous exposures with this chemical in D. magna. The IC50 was defined as a concentration that immobilizes 50% of the exposed D. magna. Eight percent immobilization in D. magna was observed after 48 hours of exposure to 100 mg/L of Disodium 5-acetylamino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate. The IC8 was therefore estimated to be 100 mg/L. Based on the IC8, it can be concluded that the chemical was nontoxic and can be consider to be not classified as per CLP classification criteria.

 

Similarly in the third weight of evidence study for the read across chemical Amaranth dye (915-67-3) from ABITEC report, toxicity study was carried out. Determination of the inhibition of the mobility of daphnids was carried out with the substance 2,7-Naphthalenedisulfonic acid, 3-hydroxy- 4-[(4-sulfo-1-naphthalenyl), sodium salt; Amaranth dye according to OECD Guideline 202. The limit test was performed at 100 mg/l. Effects on immobilisation were observed for 48 hours. The effective concentration (EC8) for the test substance, 2,7-Naphthalenedisulfonic acid, 3-hydroxy-4- [(4-sulfo-1 -naphthalenyl), sodium salt (Amaranth dye), in Daphnia magna was determined to be 100 mg/L on the basis of mobility inhibition effects in a 48 hour study. 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.

 

 

Based on the predicted data for the target chemical and experimental studies for the read across chemical obtain from various sources (ABITEC reports) toxicity on invertebrates was studied and it was concluded that the chemical Sodium 6-amino-5-[[4-chloro-2-(trifluoromethyl)phenyl]azo]-4-hydroxynaphthalene-2-sulphonate was consider as nontoxic and can be consider to be not classified as toxic to aquatic invertebrates as per CLP classification criteria.