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Biodegradation in water: screening tests

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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 is attached
Qualifier:
according to
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 v3.4
GLP compliance:
not specified
Specific details on test material used for the study:
- Name of test material: 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene -2,7-disulphonic acid
- IUPAC name: 4-amino-3,6-bis[(E)-2-[4-({4-chloro-6-[(3-sulfophenyl)amino]-1,3,5-triazin-2-yl}amino)-2-sulfophenyl]diazen-1-yl]-5-hydroxynaphthalene -2,7-disulfonic acid
- Molecular formula: C40H29Cl2N15O19S6
- Molecular weight: 1287.0571 g/mole
- Smiles : c1cc(cc(c1)S(=O)(=O)O)Nc2nc(nc(n2)Cl)Nc3ccc(c(c3)S(=O)(=O)O)/N=N/c4c(cc5cc(c(c(c5c4N)O)/N=N/c6ccc(cc6S(=O)(=O)O) Nc7nc (nc(n7)Cl)Nc8cccc(c8)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O
- Inchl: 1S/C40H29Cl2N15O19S6/c41-35-48-37(44-18-3-1-5-22(13-18)77(59,60)61)52-39(50-35)46-20-7-9-24(26(15-20)79(65,66)67)54-56-32-28(81 (71,72)73)11-17-12-29(82(74,75)76)33(34(58)30(17)31(32)43)57-55-25-10-8-21(16-27(25)80(68,69)70)47-40-51-36(42)49-38(53-40)45-19-4-2-6-23(14-19)78(62,63)64/h1-16,58H,43H2,(H,59,60,61)(H,62,63,64)(H,65,66,67)(H,68,69,70)(H,71,72,73)(H,74,75,76)(H2,44,46,48,50,52)(H2,45,47,49,51,53)/b56-54+,57-55+
- 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:
other: BOD
Key result
Parameter:
other: % biodegradation by BOD
Value:
0.111
Sampling time:
28 d
Remarks on result:
other: other details not available
Details on results:
Percent biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid was estimated to be 0.11% by considering 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 8 nearest neighbours
Domain  logical expression:Result: In Domain

(((((((((("a" or "b" or "c" or "d" )  and "e" )  and "f" )  and "g" )  and "h" )  and ("i" and ( not "j") )  )  and "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 Acid moiety OR Anilines (Unhindered) OR Phenol Amines OR Phenols OR Triazines, Aromatic by Aquatic toxicity classification by ECOSAR ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SNAr OR SNAr >> Nucleophilic aromatic substitution OR SNAr >> Nucleophilic aromatic substitution >> Halo-triazines by Protein binding by OECD ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Michael-type addition to quinoid structures  OR AN2 >> Michael-type addition to quinoid structures  >> Substituted Anilines 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 v1.4 ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR SN1 OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines by DNA binding by OASIS v.1.4 ONLY

Domain logical expression index: "e"

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

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 7) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as High (Class III) by Toxic hazard classification by Cramer (original) ONLY

Domain logical expression index: "h"

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: "i"

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 16 - Sulfur S AND Group 17 - Halogens Cl AND Group 17 - Halogens F,Cl,Br,I,At by Chemical elements

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Group 1 - Alkali Earth Li,Na,K,Rb,Cs,Fr OR Group 17 - Halogens Br by Chemical elements

Domain logical expression index: "k"

Similarity boundary:Target: Nc1c(N=Nc2ccc(Nc3nc(Nc4cccc(S(O)(=O)=O)c4)nc(Cl)n3)cc2S(O)(=O)=O)c(S(O)(=O)=O)cc2cc(S(O)(=O)=O)c(N=Nc3ccc(Nc4nc(Nc5cccc(S(O)(=O)=O)c5)nc(Cl)n4)cc3S(O)(=O)=O)c(O)c12
Threshold=10%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "l"

Similarity boundary:Target: Nc1c(N=Nc2ccc(Nc3nc(Nc4cccc(S(O)(=O)=O)c4)nc(Cl)n3)cc2S(O)(=O)=O)c(S(O)(=O)=O)cc2cc(S(O)(=O)=O)c(N=Nc3ccc(Nc4nc(Nc5cccc(S(O)(=O)=O)c5)nc(Cl)n4)cc3S(O)(=O)=O)c(O)c12
Threshold=40%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Not categorized by Repeated dose (HESS)

Domain logical expression index: "n"

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

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of log BCF max which is >= 1.28 log(L/kg wet)

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of log BCF max which is <= 4.45 log(L/kg wet)

Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
Percent biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid was estimated to be 0.11% by considering BOD as parameter and microorganisms as inoculum in 28 days.On the basis of this percent biodegraddability it is conccluded that test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid is not readily biodegradable.
Executive summary:

Biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid

(CAS no. 51357 -74 -5)was estimated by using OECD QSAR tool box v3.4 by considering eight cloest read across chemicals with log KOw as primary descriptor. Percent biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid  was estimated to be 0.11% by considering BOD as parameter  and microorganisms as inoculum in 28 days.On the basis of this percent biodegraddability it is conccluded that test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid  is not readily biodegradable.

Description of key information

Biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid

(CAS no. 51357 -74 -5)was estimated by using OECD QSAR tool box v3.4 by considering eight cloest read across chemicals with log KOw as primary descriptor. Percent biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid  was estimated to be 0.11% by considering BOD as parameter  and microorganisms as inoculum in 28 days.On the basis of this percent biodegraddability it is conccluded that test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid  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 compound4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid

(CAS no. 51357 -74 -5)and supporting weight of evidence studies for its 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 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid (CAS no. 51357 -74 -5)was estimated by using OECD QSAR tool box v3.4 by considering eight closet read across chemicals with log KOw as primary descriptor. Percent biodegradability of test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid  was estimated to be 0.11% by considering BOD as parameter  and microorganisms as inoculum in 28 days. On the basis of this percent biodegradability it is concluded that test chemical 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid  is not readily biodegradable.

 

Second weight of evidence study was done by using Estimation Programs Interface Suite (EPI suite, 2017)in this study the biodegradation potential of the test compound 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid (CAS no. 51357 -74 -5) was estimated 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 4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid is expected to be not readily biodegradable.

 

Third weight of evidence study was done from chemosphere journal Vo1.15, No.4, pp 479-491 (1986)by U. Pagga and O. Brown in this study the aerobic biodegradation experiment was performed for read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4)( CAS no.17095-24-8) using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100mg/L for 28 days. By considering DOC removal parameter the read across chemical showed -53 % degradation in 28 days. This read across chemical was categorized in D category which shows no elimination in static test. This percentage value is also very less So it is concluded that chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) is not readily biodegradable.

 

Last weight of evidence study was done from authoritative database ( J check, 2017) in this study the read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) (CAS no. 17095-24-8) was subjected to biodegradation test by taking activated sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and HPLC parameters. The initial concentration of read across chemical was 100 mg/L. The study design used was of standard type. The read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) showed 4.0 % and 9 % biodegradation by considering BOD and TOC as parameter respectively but it showed 96 % biodegradation by HPLC parameter . Percent biodegradability values of read across chemical by BOD and TOC parameters are very low but by HPLC parameter read across chemical showed very high biodegradability but this high value of biodegradation is not due complete degradation of read across chemical but it is due to partial change of read across chemical and formation of 4-Amino-5-hydroxy-3,6-bis[4-(vinylsulfonyl)phenylazo]-2,7-naphthalenedisulfonic acid . Therefore on the basis of percent biodegradability by BOD and TOC parameters it is concluded that read across chemical 2,7-Naphthalenedisulfonic acid, 4-amino-5-hydroxy-3,6-bis[2-[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]diazenyl]-, sodium salt (1:4) is not readily biodegradable.

 

On the basis of results of above mentioned studies for target chemical4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acid (CAS no. 51357-74-5)(from OECD QSAR tool box v3.4 and EPI suite) and supporting weight of evidence study (from, Chemosphere journal and J Check, 2017). It is concluded that the test chemical4-amino-3,6-bis[[4-[[4-chloro-6-[(3-sulphophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonic acidcan be expected to be not readily biodegradable.