Benzoic acid, 2,3,4,5-tetrachloro-6-cyano-, methyl ester, reaction products with p-phenylenediamine and sodium methoxide

Biodegradation in soil

Administrative data

Endpoint:

biodegradation in soil: simulation testing

Data waiving:

study scientifically not necessary / other information available

Justification for data waiving:

other:

Justification for type of information:

see attached justification

Cross-reference

Cross-reference 1

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

additional information on environmental fate and behaviour

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2021

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

other: OECD 318

At any of the time points mentioned in the TG-318, the influence of Ca is critical. Regardless of pH, the pigment is least stable in 10 mM Ca, representing high water hardness.
After 6h, the samples showed high dispersion stability in 0 mM Ca and intermediate stability at all other conditions.
After 24 hours the stability in 0 mM Ca at pH 4 remained high. The stability in 0 mM Ca at pH 9 became intermediate. For the samples at all other conditions the stability was low.

 

Full results of the dispersion stability in the presence of NOM
	Ca(NO3)2	Stability after 6h	Standard deviation	Stability after 15h	Standard deviation	Stability after 24h	Standard deviation
	[mM]	[%]	[%]	[%]	[%]	[%]	[%]
pH 4	0	96.8	0.6	94.9	0.1	92.8	0.3
pH 4	1	75.3	0.9	22.2	1.0	10.2	1.5
pH 4	10	14.5	1.5	6.6	0.6	2.9	0.4
.
pH 7	0	98.4	0.1	66.2	11.1	6.8	2.3
pH 7	1	38.9	0.3	10.8	0.3	5.0	0.2
pH 7	10	10.3	0.7	4.4	0.3	1.9	0.1
.
pH 9	0	89.8	0.7	83.9	0.3	78.2	1.5
pH 9	1	22.0	3.2	7.7	0.7	3.9	0.7
pH 9	10	14.6	1.1	0.0.	0.6	19.4	2.0

 

To rationalize the observed dispersion stability, we finally checked the particle size distribution directly in the environmental medium. We applied the NanoDefine method of Analytical Ultracentrifugation (SOP AUC-RI, published by 3). The centrifugation parameters are given in the methods section.
As required by TG318, paragraph 31, the tested nanomaterial was pre-wetted in ultrapure water and left in the form of wet-paste for 24 h. The TG318 requires this step “to insure the proper interaction of nanomaterial surface with ultrapure water.” We visually observed incomplete wetting, and so any ensuing measurement would have been incorrect. In accord with the NanoGenoTox dispersion protocol, a drop of ethanol was added, successfully transferred the powder into a paste, which was then further diluted as specified in the TG318
The observed size distributions confirm the moderate agglomeration at 1 mM Ca, pH7, with NOM (Figure 4). If the particles would have been significantly dissolved, no size distribution would be observable at all by this method, which relies on the detection of the movement of particles during centrifugal separation.
Additionally, the centrifugation methods include a determination of the remaining absorption after centrifugation, fully consistent with the conventional determination of the dissolved fraction after centrifugation as recommended by the TG-318. The remaining absorption was measured at ca. 0.01. This is a fraction of 1% of the initial absorption, but actually is close to the LOD of the built-in UV/Vis detector. Considering the LOD, between 0% and 1% of the sample may have been dissolved.
All evidence combined, the results after centrifugation confirm that at least 99% of the observed dispersion stability has to be attributed to the particles, not to dissolution.

 

 

Executive summary:

At any of the time points mentioned in the TG-318, the influence of Ca is critical. Regardless of pH, the pigment is least stable in 10 mM Ca, representing high water hardness.
After 6h, the samples showed high dispersion stability in 0 mM Ca and intermediate stability at all other conditions.
After 24 hours the stability in 0 mM Ca at pH 4 remained high. The stability in 0 mM Ca at pH 9 became intermediate. For the samples at all other conditions the stability was low.

Cross-reference 2

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

biodegradation in water: ready biodegradability

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, but not (completely) falling into its applicability domain, with adequate and reliable documentation / justification

Remarks:

Parameter ranges: In domain; Structural domain: Out of domain (Correct fragments: 95.24%; Incorrect fragments: 0%; Unknown fragments: 4.76%);

Justification for type of information:

1. SOFTWARE
OASIS Catalogic v5.13.1.156

2. MODEL (incl. version number)
CATALOGIC 301C v.11.15

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
See section 'Test Material'.

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
See attached QMRF.

5. APPLICABILITY DOMAIN
See attached QPRF.

6. ADEQUACY OF THE RESULT
- The model is scientifically valid (see attached QMRF).
- The model estimates the biodegradability of a substance Screening information on the ready biodegradability is required for substances manufactured or imported in quantities of 1 t/y or more. Depending on the results, further information may be required for substances manufactured or imported in quantities of 100 t/y or more (simulation testing on ultimate degradation in surface water/soil/sediment). Column 2 of REACH Annex VII provides exemptions for conducting the study. It does not need to be conducted if the substance is inorganic. According to column 2 of REACH Annex IX, testing is not required if the substance is highly insoluble in water, or the substance is readily biodegradable.
- See attached QPRF for reliability assessment.

Principles of method if other than guideline:

Estimation of ready biodegradation in water using CATALOGIC v5.13.1.156 BOD 28 days MITI (OECD 301C) v11.15

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: model calculation

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

O2 consumption

Parameter:

% degradation (O2 consumption)

Value:

5

Sampling time:

28 d

Remarks on result:

other: The octachloro derivative is not completely within the applicability domain of the model due to 4.76% unknown fragments in the training set.

Parameter:

% degradation (O2 consumption)

Value:

10

Sampling time:

28 d

Remarks on result:

other: The monomethoxy-heptachloro derivative is not completely within the applicability domain of the model due to 13.64% unknown fragments in the training set.

Parameter:

% degradation (O2 consumption)

Value:

14

Sampling time:

28 d

Remarks on result:

other: The bismethoxy-hexachloro derivative is not completely within the applicability domain of the model due to 21.74% unknown fragments in the training set.

Octachloro derivative:

-Concomitant predictions:

Not ready degradable

Primary Half Life = 9.97 days

Ultimate Half Life = 11m 17d

- Predicted value (model result): O2 -consumption (BOD) = 0.05 ± 0.0178

Metabolite predition:

The model Catalogic 301 C v11.15 (OASIS Catalogic v5.13.1.156) calculated 125 metabolites (see octachloro document attached under "attached background material") identifying 48 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1%.

All metabolites identified as relevant degradation products were calculated to be not readily biodegradable. Individual biodegradation of these metabolites was estimated to be 0% to 10% after 28 days (based on BOD).

Monomethoxy-heptachloro derivative:

-Concomitant predictions:

Not ready degradable

Primary Half Life = 5.33 days

Ultimate Half Life = 6m 4d

- Predicted value (model result): O2 -consumption (BOD) = 0.10 ± 0.0148

Metabolite predition:

The model Catalogic 301 C v11.15 (OASIS Catalogic v5.13.1.156) calculated 175 metabolites (see monomethoxy-heptachloro document attached under "attached background material") identifying 58 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of≥ 0.1%.

All metabolites identified as relevant degradation products were calculated to be not readily biodegradable. Individual biodegradation of these metabolites was estimated to be 1% to 11% after 28 days (based on BOD). Only one metabolites was identified as biodegradable (100%) based on BOD. Since the quantity is only 0.14% the overall conclusion will not be affected.

Bismethoxy-hexachloro derivative:

-Concomitant predictions:

Not ready degradable

Primary Half Life = 3.64 days

Ultimate Half Life = 4m 7d

- Predicted value (model result): O2 -consumption (BOD) = 0.14 ± 0.0181

Metabolite predition:

The model Catalogic 301 C v11.15 (OASIS Catalogic v5.13.1.156) calculated 45 metabolites (see bismethoxy-hexachloro document attached under "attached background material") identifying 24 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of≥ 0.1%.

All metabolites identified as relevant degradation products were calculated to be not readily biodegradable. Individual biodegradation of these metabolites was estimated to be 3% to 13% after 28 days (based on BOD).

Only one metabolites was identified as biodegradable (100%) based on BOD. Since the quantity is only 0.25% the overall conclusion will not be affected.

Interpretation of results:

not readily biodegradable

Remarks:

according to OECD criteria

Cross-reference 3

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

biodegradation in water: ready biodegradability

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, but not (completely) falling into its applicability domain, with adequate and reliable documentation / justification

Principles of method if other than guideline:

Prediction of ready biodegradability based on EPI Suite v4.10 BIOWIN v4.10.

GLP compliance:

no

Remarks on result:

other: Ready biodegradability prediction: Substance is not readily biodegradable.

Remarks:

It is true for the three derivatives

Results octachloro derivative:

Biowin1 (Linear Model Prediction)   : Does Not Biodegrade Fast

Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin3 (Ultimate Biodegradation Timeframe): Recalcitrant

Biowin4 (Primary Biodegradation Timeframe): Months

Biowin5 (MITI Linear Model Prediction)   : Does Not Biodegrade Fast

Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

 

TYPE	NUM	Biowin1 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.2102	0.4203
Frag	8	Aromatic chloride  [-CL]	-0.1824	-1.4594
MolWt	*	Molecular Weight Parameter		-0.3056
Const	*	Equation Constant		0.7475
RESULT	Biowin1 (Linear Biodeg Probability)			-0.5971

 

 

 

TYPE	NUM	Biowin2 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	2.6913	5.3826
Frag	8	Aromatic chloride  [-CL]	-2.0155	-16.1240
MolWt	*	Molecular Weight Parameter		-9.1156
RESULT	Biowin2 (Non-Linear Biodeg Probability)			0.0000

 

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

TYPE	NUM	Biowin3 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	-0.0542	-0.1084
Frag	8	Aromatic chloride  [-CL]	-0.2066	-1.6528
MolWt	*	Molecular Weight Parameter		-1.4186
Const	*	Equation Constant		3.1992
RESULT	Biowin3 (Survey Model - Ultimate Biodeg)			0.0193

 

 

TYPE	NUM	Biowin4 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.2054	0.4109
Frag	8	Aromatic chloride  [-CL]	-0.1653	-1.3227
MolWt	*	Molecular Weight Parameter		-0.9262
Const	*	Equation Constant		3.8477
RESULT	Biowin4 (Survey Model - Primary Biodeg)			2.0097

 

Result Classification:  5.00 -> hours    4.00 -> days   3.00 -> weeks

(Primary & Ultimate)   2.00 -> months   1.00 -> longer

 

TYPE	NUM	Biowin5 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.1266	0.2533
Frag	8	Aromatic chloride  [-CL]	0.0062	0.0494
Frag	4	Aromatic-H	0.0082	0.0329
MolWt	*	Molecular Weight Parameter		-1.9098
Const	*	Equation Constant		0.7121
RESULT	Biowin5 (MITI Linear Biodeg Probability)			-0.8621

 

TYPE	NUM	Biowin6 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.8859	1.7717
Frag	8	Aromatic chloride  [-CL]	-0.2191	-1.7532
Frag	4	Aromatic-H	0.1201	0.4806
MolWt	*	Molecular Weight Parameter		-18.5321
RESULT	Biowin6 (MITI Non-Linear Biodeg Probability)			0.0000

 

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

 

 

TYPE	NUM	Biowin7 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	-0.5679	-1.1358
Frag	8	Aromatic chloride  [-CL]	-0.4023	-3.2182
Frag	4	Aromatic-H	-0.0954	-0.3817
Const	*	Equation Constant		0.8361
RESULT	Biowin7 (Anaerobic Linear Biodeg Prob)			-3.8996

 

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

Ready Biodegradability Prediction: (YES or NO)

----------------------------------------------

Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey model) result is "weeks" or faster (i.e. "days", "days to weeks", or "weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then the prediction is YES (readily biodegradable). If this condition is not satisfied, the prediction is NO (not readily biodegradable). This method is based on application of Bayesian analysis to ready biodegradation data (see Help). Biowin5 and 6 also predict ready biodegradability, but for degradation in the OECD301C test only; using data from the Chemicals Evaluation and Research Institute Japan (CERIJ) database.

Results monomethoxy-heptachloro derivative:

Biowin1 (Linear Model Prediction)   : Does Not Biodegrade Fast

Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin3 (Ultimate Biodegradation Timeframe): Recalcitrant

Biowin4 (Primary Biodegradation Timeframe): Weeks-Months

Biowin5 (MITI Linear Model Prediction)   : Does Not Biodegrade Fast

Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

 

TYPE	NUM	Biowin1 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.2102	0.4203
Frag	7	Aromatic chloride  [-CL]	-0.1824	-1.2769
Frag	1	Aromatic ether [-O-aromatic carbon]	0.1319	0.1319
MolWt	*	Molecular Weight Parameter		-0.3035
Const	*	Equation Constant		0.7475
RESULT	Biowin1 (Linear Biodeg Probability)			-0.2807

 

TYPE	NUM	Biowin2 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	2.6913	5.3826
Frag	7	Aromatic chloride  [-CL]	-2.0155	-14.1085
Frag	1	Aromatic ether [-O-aromatic carbon]	2.2483	2.2483
MolWt	*	Molecular Weight Parameter		-9.0528
RESULT	Biowin2 (Non-Linear Biodeg Probability)			0.0000

 

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

TYPE	NUM	Biowin3 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	-0.0542	-0.1084
Frag	7	Aromatic chloride  [-CL]	-0.2066	-1.4462
Frag	1	Aromatic ether [-O-aromatic carbon]	-0.0581	-0.0581
MolWt	*	Molecular Weight Parameter		-1.4088
Const	*	Equation Constant		3.1992
RESULT	Biowin3 (Survey Model - Ultimate Biodeg)			0.1776

 

TYPE	NUM	Biowin4 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.2054	0.4109
Frag	7	Aromatic chloride  [-CL]	-0.1653	-1.1574
Frag	1	Aromatic ether [-O-aromatic carbon]	0.0771	0.0771
MolWt	*	Molecular Weight Parameter		-0.9198
Const	*	Equation Constant		3.8477
RESULT	Biowin4 (Survey Model - Primary Biodeg)			2.2585

 

Result Classification:  5.00 -> hours    4.00 -> days   3.00 -> weeks

(Primary & Ultimate)   2.00 -> months   1.00 -> longer

 

TYPE	NUM	Biowin5 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.1266	0.2533
Frag	7	Aromatic chloride  [-CL]	0.0062	0.0432
Frag	1	Aromatic ether [-O-aromatic carbon]	0.1952	0.1952
Frag	4	Aromatic-H	0.0082	0.0329
Frag	1	Methyl [-CH3]	0.0004	0.0004
MolWt	*	Molecular Weight Parameter		-1.8966
Const	*	Equation Constant		0.7121
RESULT	Biowin5 (MITI Linear Biodeg Probability)			-0.6595

 

TYPE	NUM	Biowin6 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.8859	1.7717
Frag	7	Aromatic chloride  [-CL]	-0.2191	-1.5340
Frag	1	Aromatic ether [-O-aromatic carbon]	1.3227	1.3227
Frag	4	Aromatic-H	0.1201	0.4806
Frag	1	Methyl [-CH3]	0.0194	0.0194
MolWt	*	Molecular Weight Parameter		-18.4045
RESULT	Biowin6 (MITI Non-Linear Biodeg Probability)			0.0000

 

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

 

 

TYPE	NUM	Biowin7 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	-0.5679	-1.1358
Frag	7	Aromatic chloride  [-CL]	-0.4023	-2.8159
Frag	1	Aromatic ether [-O-aromatic carbon]	0.1780	0.1780
Frag	4	Aromatic-H	-0.0954	-0.3817
Frag	1	Methyl [-CH3]	-0.0796	-0.0796
Const	*	Equation Constant		0.8361
RESULT	Biowin7 (Anaerobic Linear Biodeg Prob)			-3.3988

 

 

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

Ready Biodegradability Prediction: (YES or NO)

----------------------------------------------

Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey model) result is "weeks" or faster (i.e. "days", "days to weeks", or "weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then the prediction is YES (readily biodegradable). If this condition is not satisfied, the prediction is NO (not readily biodegradable). This method is based on application of Bayesian analysis to ready biodegradation data (see Help). Biowin5 and 6 also predict ready biodegradability, but for degradation in the OECD301C test only; using data from the Chemicals Evaluation and Research Institute Japan (CERIJ) database.

 

Results bismethoxy-hexachloro derivative:

Biowin1 (Linear Model Prediction)   : Does Not Biodegrade Fast

Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin3 (Ultimate Biodegradation Timeframe): Recalcitrant

Biowin4 (Primary Biodegradation Timeframe): Weeks-Months

Biowin5 (MITI Linear Model Prediction)   : Does Not Biodegrade Fast

Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

 

TYPE	NUM	Biowin1 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.2102	0.4203
Frag	6	Aromatic chloride  [-CL]	-0.1824	-1.0945
Frag	2	Aromatic ether [-O-aromatic carbon]	0.1319	0.2638
MolWt	*	Molecular Weight Parameter		-0.3014
Const	*	Equation Constant		0.7475
RESULT	Biowin1 (Linear Biodeg Probability)			0.0357

 

TYPE	NUM	Biowin2 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	2.6913	5.3826
Frag	6	Aromatic chloride  [-CL]	-2.0155	-12.0930
Frag	2	Aromatic ether [-O-aromatic carbon]	2.2483	4.4966
MolWt	*	Molecular Weight Parameter		-8.9901
RESULT	Biowin2 (Non-Linear Biodeg Probability)			0.0003

 

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

TYPE	NUM	Biowin3 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	-0.0542	-0.1084
Frag	6	Aromatic chloride  [-CL]	-0.2066	-1.2396
Frag	2	Aromatic ether [-O-aromatic carbon]	-0.0581	-0.1162
MolWt	*	Molecular Weight Parameter		-1.3991
Const	*	Equation Constant		3.1992
RESULT	Biowin3 (Survey Model - Ultimate Biodeg)			0.3358

 

TYPE	NUM	Biowin4 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.2054	0.4109
Frag	6	Aromatic chloride  [-CL]	-0.1653	-0.9920
Frag	2	Aromatic ether [-O-aromatic carbon]	0.0771	0.1542
MolWt	*	Molecular Weight Parameter		-0.9134
Const	*	Equation Constant		3.8477
RESULT	Biowin4 (Survey Model - Primary Biodeg)			2.5074

 

Result Classification:  5.00 -> hours    4.00 -> days   3.00 -> weeks

(Primary & Ultimate)   2.00 -> months   1.00 -> longer

 

TYPE	NUM	Biowin5 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.1266	0.2533
Frag	6	Aromatic chloride  [-CL]	0.0062	0.0370
Frag	2	Aromatic ether [-O-aromatic carbon]	0.1952	0.3905
Frag	4	Aromatic-H	0.0082	0.0329
Frag	2	Methyl [-CH3]	0.0004	0.0008
MolWt	*	Molecular Weight Parameter		-1.8835
Const	*	Equation Constant		0.7121
RESULT	Biowin5 (MITI Linear Biodeg Probability)			-0.4569

 

TYPE	NUM	Biowin6 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	0.8859	1.7717
Frag	6	Aromatic chloride  [-CL]	-0.2191	-1.3149
Frag	2	Aromatic ether [-O-aromatic carbon]	1.3227	2.6454
Frag	4	Aromatic-H	0.1201	0.4806
Frag	2	Methyl [-CH3]	0.0194	0.0389
MolWt	*	Molecular Weight Parameter		-18.2769
RESULT	Biowin6 (MITI Non-Linear Biodeg Probability)			0.0000

 

 

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

 

 

TYPE	NUM	Biowin7 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Amide  [-C(=O)-N or -C(=S)-N]	-0.5679	-1.1358
Frag	6	Aromatic chloride  [-CL]	-0.4023	-2.4136
Frag	2	Aromatic ether [-O-aromatic carbon]	0.1780	0.3560
Frag	4	Aromatic-H	-0.0954	-0.3817
Frag	2	Methyl [-CH3]	-0.0796	-0.1591
Const	*	Equation Constant		0.8361
RESULT	Biowin7 (Anaerobic Linear Biodeg Prob)			-2.8981

 

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

 

Ready Biodegradability Prediction: (YES or NO)

----------------------------------------------

Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey model) result is "weeks" or faster (i.e. "days", "days to weeks", or "weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then the prediction is YES (readily biodegradable). If this condition is not satisfied, the prediction is NO (not readily biodegradable). This method is based on application of Bayesian analysis to ready biodegradation data (see Help). Biowin5 and 6 also predict ready biodegradability, but for degradation in the OECD301C test only; using data from the Chemicals Evaluation and Research Institute Japan (CERIJ) database.

Interpretation of results:

not readily biodegradable

Cross-reference 4

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

biodegradation in water: ready biodegradability

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, but not (completely) falling into its applicability domain, with adequate and reliable documentation / justification

Principles of method if other than guideline:

The model is based on the OECD TG 301C - modified MITI -I test data and provides a qualitative evaluation (binary classification) of ready biodegradability properties. It has been developed using Sarpy software, by Istituto di Ricerche Farmacologiche Mario Negri and Politecnico di Milano.
The applicability domain of predictions is assessed using an Applicability Domain Index (ADI) that has values from 0 (worst case) to 1 (best case). The ADI is calculated by grouping several other indices, each one taking into account a particular issue of the applicability domain. Most of the indices are based on the calculation of the most similar compounds found in the training and test set of the model, calculated by a similarity index that consider molecule's fingerprint and structural aspects (count of atoms, rings and relevant fragments).

GLP compliance:

no

Remarks on result:

other: Result: The substance is not readily biodegradable. It is out of the Applicability Domain of the model according to the AD index. This state ment is true for all three derivates.

Model output octachloro derivative:

Compound: Molecule 0

Compound SMILES: O=C4NC(=Nc3ccc(N=C1NC(=O)c2c1c(c(c(c2Cl)Cl)Cl)Cl)cc3)c5c4c(c(c(c5Cl)Cl)Cl)Cl

Experimental value: -

Predicted RB activity: NON Readily Biodegradable

No. alerts for non RB: 3

No. alerts for possible non RB: 3

No. alerts for RB: 0

No. alerts for possible RB: 0

Structural alerts: Non RB alert no. 1 (1,2-dichlorobenzene); Non RB alert no. 21 (methanimine); Non RB alert no. 25 (2-chlorobenzaldehyde); Possible non RB alert no. 2 (1-chloro-2-methylbenzene); Possible non RB alert no. 7 (chlorobenzene); Possible non RB alert no. 11 (halogenated ring structure)

Reliability: the predicted compound is outside the Applicability Domain of the model

Remarks: none

Model output monomethoxy-heptachloro derivative:

Compound: Molecule 0

Compound SMILES: O=C4NC(=Nc3ccc(N=C1NC(=O)c2c1c(c(c(c2Cl)Cl)Cl)Cl)cc3)c5c4c(c(OC)c(c5Cl)Cl)Cl

Experimental value: -

Predicted RB activity: NON Readily Biodegradable

No. alerts for non RB: 4

No. alerts for possible non RB: 3

No. alerts for RB: 0

No. alerts for possible RB: 1

Structural alerts: Non RB alert no. 1 (1,2-dichlorobenzene); Non RB alert no. 10 (3-chlorophenol); Non RB alert no. 21 (methanimine); Non RB alert no. 25 (2-chlorobenzaldehyde); Possible non RB alert no. 2 (1-chloro-2-methylbenzene); Possible non RB alert no. 7 (chlorobenzene); Possible non RB alert no. 11 (halogenated ring structure); Possible RB alert no. 19 (anisole)

Reliability: the predicted compound is outside the Applicability Domain of the model

Remarks: none

Model output bismethoxy-hexaachloro derivative:

Compound: Molecule 0

Compound SMILES: O=C4NC(=Nc3ccc(N=C1NC(=O)c2c1c(c(c(OC)c2Cl)Cl)Cl)cc3)c5c4c(c(OC)c(c5Cl)Cl)Cl

Experimental value: -

Predicted RB activity: NON Readily Biodegradable

No. alerts for non RB: 4

No. alerts for possible non RB: 3

No. alerts for RB: 0

No. alerts for possible RB: 1

Structural alerts: Non RB alert no. 1 (1,2-dichlorobenzene); Non RB alert no. 10 (3-chlorophenol); Non RB alert no. 21 (methanimine); Non RB alert no. 25 (2-chlorobenzaldehyde); Possible non RB alert no. 2 (1-chloro-2-methylbenzene); Possible non RB alert no. 7 (chlorobenzene); Possible non RB alert no. 11 (halogenated ring structure); Possible RB alert no. 19 (anisole)

Reliability: the predicted compound is outside the Applicability Domain of the model

Remarks: none

Interpretation of results:

not readily biodegradable