Copper, [29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32]-, [[3-(dimethylamino)propyl]amino]sulfonyl derivs.

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: screening test, other

Remarks:

QSAR prediction

Type of information:

(Q)SAR

Adequacy of study:

supporting study

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 adequate and reliable documentation / justification

Justification for type of information:

1. SOFTWARE
Individual model BIOWIN included in the Estimation Programs Interface (EPI) Suite.

2. MODEL (incl. version number)
BIOWIN v4.10 included in EPISuite v 4.11, 2000 - 2017

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
The CAS NUMBER/SMILES CODE was entered in the initial data entry screen.

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
a. Defined endpoint:
BIOWIN2: probability of fast or not fast biodegradability
BIOWIN3: probability of ultimate biodegradability
BIOWIN6: probability of ready or not ready biodegradability

b. Explicit algorithm (OECD Principle 2):
BIOWIN2:
Calculation of the fast biodegradation probability for any compound begins by summing, for all the fragments present in that compound, the fragment coefficient multiplied by the number of instances of the fragment in the compound (for MW, the value of that parameter is multiplied by its coefficient), then adding this summation to the equation constant which is 3.0087. The summed values for each fragment coefficient multiplied by the number of instances appear in the "VALUE" column of the non-linear results screen. The non-linear fast biodegradation probability is then calculated from the logistic equation as follows, where total = 3.0087 + the summation as described above:
Non-linear probability = exp(total) / (1 + exp(total))
BIOWIN3:
The ultimate rating of a compound is calculated by summing, for all the fragments present in that compound, the fragment coefficient multiplied by the number of instances of the fragment in the compound (for MW, the value of that parameter is multiplied by its coefficient), and then adding this summation to the equation constant which is 3.1992 for Biowin3. The summed values for each fragment coefficient multiplied by the number of instances appear in the "VALUE" column of the results screen.
BIOWIN6:
The basic approach for deriving the fragment values is very similar to the approach used for the original non-linear model described above (BIOWIN2). Although the majority of fragments in the new MITI model are identical to fragments in the models described above, the new MITI model incorporates various changes. For example, to provide fuller characterization of alkyl chain length and branching, the original C4 terminal alkyl group fragment was replaced with a fragment set consisting of -CH3, -CH2 (both linear and ring types), -CH (both linear and ring types), and - C=CH (alkenyl hydrogen). The final MITI model contains 42 fragments and molecular weight as independent variables.

c. Define domain of applicability:
BIOWIN2:
Appendix D gives for each fragment the maximum number of instances of that fragment in any of the 295 training set compounds (the minimum number of instances is of course zero, since not all compounds had every fragment). The minimum and maximum values for molecular weight are also given (31.06 – 697.7 g/mole). Currently there is no universally accepted definition of model domain.
BIOWIN3:
Appendix D gives for each fragment the maximum number of instances of that fragment in any of the 200 training set compounds (the minimum number of instances is of course zero, since not all compounds had every fragment). The minimum and maximum values for molecular weight are also given (53.06 – 697.65 g/mole). Currently there is no universally accepted definition of model domain.
BIOWIN6:
Appendix D gives for each fragment the maximum number of instances of that fragment in any of the 589 training set compounds (the minimum number of instances is of course zero, since not all compounds had every fragment). The minimum and maximum values for molecular weight are also given (30.02 – 959.2 g/mole). Currently there is no universally accepted definition of model domain.

d. Descriptor selection: As the program requires only a chemical structure for the estimation, BIOWIN initially separates a molecule into distinct fragments. Distinct values are allocated to each fragment present in the molecule.

e. Statistics for goodness-of-fit:
BIOWIN2:
number in dataset = 295
total correct = 275/295
% correct total = 93.2
% correct, fast = 97.3 (181/186)
% correct, slow = 86.2 (94/109)
BIOWIN3:
number in dataset = 200
r2 = 0.72
mean residual (abs value) = 0.206
total correct = 167/200
% correct total = 83.5
% correct, fast = 93.5 (101/108)
% correct, slow = 71.7 (66/92)
BIOWIN6:
Training Set: Critically Evaluated as "Readily Degradable" = 204/254 (80.3%)
Training Set: Critically Evaluated as "Not Readily Degradable" = 284/335 (84.8%)
Training Set: TOTAL = 488/589 (82.9%)

f. Mechanistic interpretation: The probability of a substance to be biotically degraded in the environment by microorganisms is an important factor in determining the persistency. Knowledge on persistency is further needed for the evaluation of potential hazards of a substance in the environment.
The estimates are based upon fragment constants (of fragments that have a potential effect on biodegradability) that were developed using multiple non-linear regression analyses. For modelling each substance is split into its subgroups and the respective values/ descriptors (depending on the method) are taken for the calculation of a potential for biotical biodegradation.


5. APPLICABILITY DOMAIN
a. Descriptor Domains:
i. Molecular weight: With a molecular weight of 311.36 g/mole, the substance is within the range of all three training sets (BIOWIN2: 31.06 – 697.7 g/mole; BIOWIN3: 53.06 – 697.65 g/mole; BIOWIN6: 30.02 – 959.2 g/mole).
ii. Structural fragment domain: Regarding the structure, the fragment descriptors and equation constants used by the program for the estimation are complete and listed in Appendix D of the BIOWIN help file, except the following fragments: sulfonamide and dioxo-isoindole, which as a conclusion do not contribute to the prediction.
iii. Mechanism domain: NO INFORMATION AVAILABLE
iv. Metabolic domain: NOT RELEVANT

b. Structural analogues: No information available.

6. ADEQUACY OF THE RESULT
a. Regulatory purpose: The data may be used for regulatory purpose.
b. Approach for regulatory interpretation of the model result: If no experimental data are available, the estimated value may be used to fill data gaps needed for hazard and risk assessment.
c. Outcome: The prediction of potential biotical degradation yields a useful result for further
evaluation.
d. Conclusion: The result is considered as useful for regulatory purposes.

Qualifier:

according to guideline

Guideline:

other: REACH guidance on information requirements and chemical safety assessment, chapter R.6: QSARs and grouping of chemicals, May 2008.

Principles of method if other than guideline:

Individual model BIOWIN included in the Estimation Programs Interface (EPI) Suite v4.11.
The Estimation Programs Interface was developed by the US Environmental Agency's Office of Pollution Prevention and Toxics and Syracuse Research Corporation (SRC).

Specific details on test material used for the study:

SMILES: [NH]1C(=O)C2=CC=C(C=C2C1=O)S(=O)(=O)NCCCN(C)C

Parameter:

probability of ready biodegradability (QSAR/QSPR)

Remarks:

BIOWIN6

Value:

0.016

Remarks on result:

other: QSAR predicted value

Parameter:

probability of ready biodegradability (QSAR/QSPR)

Remarks:

BIOWIN3

Value:

2.256

Remarks on result:

other: QSAR predicted value

Parameter:

probability of ready biodegradability (QSAR/QSPR)

Remarks:

BIOWIN2

Value:

0.026

Remarks on result:

other: QSAR predicted value

Validity of model:
1. Defined Endpoint:
BIOWIN2: probability of fast or not fast biodegradability
BIOWIN3: probability of ultimate biodegradability
BIOWIN6: probability of ready or not ready biodegradability

 

2. Descriptor values:

For the test substance the following fragment descriptors were applied: 

BIOWIN2 

type	number	fragment description	coefficient	value
Frag	1	Tertiary amine	-2.2229	-2.2229
MolWt	*	Molecular Weight Parameter		-4.4213
Result		Biowin2 (Non-Linear Biodeg Probability)		0.0257

BIOWIN3 

type	number	fragment description	coefficient	value
Frag	1	Tertiary amine	-0.2548	-0.2548
MolWt	*	Molecular Weight Parameter		-0.6881
Const	*	Equation Constant		3.1992
Result		Biowin3 (Survey Model - Ultimate Biodeg)		2.2563

BIOWIN6 

type	number	fragment description	coefficient	value
Frag	1	Tertiary amine	-1.6622	-1.6622
Frag	3	Aromatic-H	0.0342	0.1026
Frag	2	Methyl [-CH3]	0.2351	0.4702
Frag	3	-CH2- [linear]	0.2345	0.7035
MolWt	*	Molecular Weight Parameter		-5.3865
Result		Biowin6 (MITI Non-Linear Biodeg Probability)		0.0161

 

3. Applicability domain: 

Molecular weight: With a molecular weight of 311.36 g/mole, the substance is within the range of all three training sets (BIOWIN2: 31.06 – 697.7 g/mole; BIOWIN3: 53.06 – 697.65 g/mole; BIOWIN6: 30.02 – 959.2 g/mole).
Structural fragment domain: Regarding the structure, the fragment descriptors and equation constants used by the program for the estimation are complete and listed in Appendix D of the BIOWIN help file, except the following fragments: sulfonamide and dioxo-isoindole, which as a conclusion do not contribute to the prediction.

 

4. Mechanistic interpretation: The estimates are based upon fragment constants (of fragments that have a potential effect on biodegradability) that were developed using multiple non-linear regression analyses. For modelling each substance is split into its subgroups and the respective values/ descriptors (depending on the method) are taken for the calculation of a potential for biotical biodegradation

5. Adequacy/uncertainty of prediction: The test substance contains structural fragments which are not in the training set of the model (i.e., sulfonamide and dioxo-isoindole fragments) and could lead to a potential uncertainty of the prediction. However, three different models were considered in the prediction which gives increased certainty about the biodegradability potential of the fragments included in the models.

Interpretation of results:

not readily biodegradable

Conclusions:

The substance is predicted to be not readily biodegradable in the environment. The models BIOWIN2 and 6 predicted no fast or ready biodegradation and BIOWIN3 simulated a complete biodegradation within weeks to months.

Executive summary:

The probability of biodegradation of N-[3-(dimethylamino)propyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-sulfonamide was predicted using the Estimation Program Interface EPI-Suite version 4.11.
The potential for biotical degradability was estimated using three different models. The resulting numerical values from the models are used as cut-off values for a classification of the probability of biodegradation according to the scheme defined by the respective models. The calculation resulted in the following:
BIOWIN2: the substance does not biodegrade fast (probability value < 0.5)
BIOWIN3: a complete biodegradation is predicted to be in a matter of weeks to months (probability value 2.25 – 2.75)
BIOWIN6: the substance is not readily biodegradable (probability value < 0.5)

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study without detailed documentation

Justification for type of information:

As there is no data available for C.I. Direct Blue 264 (CAS No 68411-04-1; EC No 270-096-9), read-across with the chemical closely related substance C.I. Pigment Blue 15 (CAS No 147-14-8; EC No 205-685-1) is proposed to cover this endpoint.
Both substances have a very similar chemical structure. C.I. Direct Blue 264 is an UVCB substance consisting of phthalocyanine copper complexes. All constituents have copper phthalocyanine (= C.I. Pigment Blue 15) as basic structure. Compared to C.I. Pigment Blue 15 the C.I. Direct Blue 264 constituents are carrying a varying number of side chains (sulfonic acid and dimethylaminopropyl sulfonamide).
Based on the structural similarity and the fact that the result of the study on biodegradation of C.I. Pigment Blue 15 already displays the worst case (“no biodegradation observed”) the read-across approach is assumed to be justified.

Reason / purpose for cross-reference:

read-across source

Parameter:

other: UV-Vis

Value:

0.7

Sampling time:

1 mo

Parameter:

other: BOD

Value:

0

Sampling time:

14 d

Validity criteria fulfilled:

yes

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

Within 14 d, a degradation rate of 0 % was determined for C.I. Pigment Blue 15. Thus C.I. Pigment Blue 15 is considered to be "not readily biodegradable".
Therefore based on read-across with C.I. Pigment Blue 15 also C.I. Direct Blue 264 is considered to be "not readily biodegradable".

Executive summary:

After 14 d, 0 % of the C.I. Pigment Blue 15 was degraded during the performance of a ready biodegradability test corresponding to OECD TG 301C. Thus C.I. Pigment Blue 15 is considered to be "not readily biodegradable".

Therefore based on read-across with C.I. Pigment Blue 15 also C.I. Direct Blue 264 is considered to be "not readily biodegradable".

 

As there is no data available for C.I. Direct Blue 264 (CAS No 68411-04-1; EC No 270-096-9), read-across with the chemical closely related substance C.I. Pigment Blue 15 (CAS No 147-14-8; EC No 205-685-1) is proposed to cover this endpoint.

Both substances have a very similar chemical structure. C.I. Direct Blue 264 is an UVCB substance consisting of phthalocyanine copper complexes. All constituents have copper phthalocyanine (= C.I. Pigment Blue 15) as basic structure. Compared to C.I. Pigment Blue 15 the C.I. Direct Blue 264 constituents are carrying a varying number of side chains (sulfonic acid and dimethylaminopropyl sulfonamide).

Based on the structural similarity and the fact that the result of the study on biodegradation of C.I. Pigment Blue 15 already displays the worst case (“no biodegradation observed”) the read-across approach is assumed to be justified.

Reference 3

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

guideline study without detailed documentation

Justification for type of information:

As there is no data available for C.I. Direct Blue 264 (CAS No 68411-04-1; EC No 270-096-9), read-across with the chemical closely related substance C.I. Pigment Blue 15 (CAS No 147-14-8; EC No 205-685-1) is proposed to cover this endpoint.

Reason / purpose for cross-reference:

read-across: supporting information

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

Deviations:

not specified

GLP compliance:

not specified

Oxygen conditions:

aerobic

Inoculum or test system:

other: standard activated sludge seed

Details on inoculum:

concentration of sludge: 30 ppm

Duration of test (contact time):

1 mo

Initial conc.:

100 mg/L

Parameter followed for biodegradation estimation:

other: BOD

Parameter followed for biodegradation estimation:

other: UV-VIS

Details on study design:

The sludge samples were mixed by stirring in a single container and then cultured at 25°C for one month.

Parameter:

other: UV-VIS

Value:

0.7

Sampling time:

1 mo

Parameter:

other: BOD

Value:

0

Sampling time:

14 d

Validity criteria fulfilled:

yes

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

Within 14 d, a degradation rate of 0 % was determined for C.I. Pigment Blue 15. Thus C.I. Pigment Blue 15 is considered to be "not readily biodegradable".
Therefore based on read-across with C.I. Pigment Blue 15 also C.I. Direct Blue 264 is considered to be "not readily biodegradable".

Executive summary:

After 14 d, 0 % of the C.I. Pigment Blue 15 was degraded during the performance of a ready biodegradability test corresponding to OECD TG 301C. Thus C.I. Pigment Blue 15 is considered to be "not readily biodegradable".

Therefore based on read-across with C.I. Pigment Blue 15 also C.I. Direct Blue 264 is considered to be "not readily biodegradable".

 

As there is no data available for C.I. Direct Blue 264 (CAS No 68411-04-1; EC No 270-096-9), read-across with the chemical closely related substance C.I. Pigment Blue 15 (CAS No 147-14-8; EC No 205-685-1) is proposed to cover this endpoint.

Both substances have a very similar chemical structure. C.I. Direct Blue 264 is an UVCB substance consisting of phthalocyanine copper complexes. All constituents have copper phthalocyanine (= C.I. Pigment Blue 15) as basic structure. Compared to C.I. Pigment Blue 15 the C.I. Direct Blue 264 constituents are carrying a varying number of side chains (sulfonic acid and dimethylaminopropyl sulfonamide).

Based on the structural similarity and the fact that the result of the study on biodegradation of C.I. Pigment Blue 15 already displays the worst case (“no biodegradation observed”) the read-across approach is assumed to be justified.

Description of key information

Based on read-across with the chemical closely related substance C.I. Pigment Blue 15

(CAS No 147-14-8; EC No 205-685-1) C.I. Direct Blue 264 is considered as "not readily biodegradable".

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

As there is no data available for C.I. Direct Blue 264 (CAS No 68411-04-1; EC No 270-096-9), read-across with the chemical closely related substance C.I. Pigment Blue 15 (CAS No 147-14-8; EC No 205-685-1) is proposed to cover this endpoint.

 

Both substances have a very similar chemical structure. C.I. Direct Blue 264 is an UVCB substance consisting of phthalocyanine copper complexes. All constituents have copper phthalocyanine (= C.I. Pigment Blue 15) as basic structure. Compared to C.I. Pigment Blue 15 the C.I. Direct Blue 264 constituents are carrying a varying number of side chains (sulfonic acid and dimethylaminopropyl sulfonamide).

Based on the structural similarity and the fact that the result of the study on biodegradation of C.I. Pigment Blue 15 already displays the worst case (“no biodegradation observed”) the read-across approach is assumed to be justified.

 

As additional study, the probability of biodegradation of the major degradation product N-[3-(dimethylamino)propyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-sulfonamide was predicted to be not readily biodegradable using the BIOWIN model in EPI-Suite.