[4-[[4-anilino-1-naphthyl][4-(dimethylamino)phenyl]methylene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium acetate

Endpoint summary

Description of key information

Hydrolysis

HYDROWIN v2.00 program of Estimation Programs Interface (EPI Suite, 2017) prediction model was used to predict the hydrolysis half-life of test compound

N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6). The estimated half-life of test chemical was estimated to be 16.337 and 1.634 days at pH 7 and 8 (at 25 deg C) respectively, indicating that it undergoes slow to negligible hydrolysis.

Biodegradation in water

Biodegradability of N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS no. 83803 -79 -6) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 25.65% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene) cyclohexa-2,5-dienylidene)-N-methylmethana minium acetate was estimated to be not readily biodegradable in water.

Biodegradation in water and sediment

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound

N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate

(CAS No. 83803 -79 -6). If released in to the environment, 0.563% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical in water is estimated to be 180 days (4320 hrs). The half-life (180 days estimated by EPI suite) indicates that the chemical is persistent in water and the exposure risk to aquatic animals is moderate to high whereas the half-life period of test chemical in sediment is estimated to be 1620.833 days (38900 hrs). Based on this half-life value, it indicates that N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene) cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate is persistent in sediment.

Biodegradation in soil

The half-life period of N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 51.7% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical in soil is estimated to be 360 days (8640 hrs). Based on this half-life value of test chemical, it is concluded that the chemical N-(4-((4-(dimethylamino)phenyl)(4 -(phenyl amino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate is persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to high.

Bioaccumulation: aquatic / sediment

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical N-(4 -((4 -(dimethylamino)phenyl) (4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6). The bioconcentration factor (BCF) of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl) methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate is not expected to bioaccumulate in the food chain.

Adsorption / desorption

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the adsorption coefficient i.e KOC for test substance N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen -1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate was estimated to be 127000 L/kg (log Koc = 5.103).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmeth anaminium acetate has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

Additional information

Hydrolysis

Various predicted data for the target chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(CAS No. 83803-79-6) were reviewed for the hydrolysis end point which are summarized as below:

 

In aprediction done using the HYDROWIN v2.00 program of Estimation Programs Interface (EPI Suite, 2017) prediction model, the hydrolysis half-life of test compound N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(CAS No. 83803-79-6) was estimated.The estimated half-life of test chemical was estimated to be 16.337 and 1.634 days at pH 7 and 8 (at 25 deg C) respectively, indicating that it undergoes slow to negligible hydrolysis.

In an another prediction done by SSS (2017) using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor, the hydrolysis of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate was predicted.The estimated half-life of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene) cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate was estimated to be 229.26 days, indicating that it is not hydrolysable.

 

On the basis of the above results for target chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (from OECD QSAR toolbox version 3.4 and EPI Suite, 2017), it can be concluded that the test chemical N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl) methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate undergoes slow to negligible hydrolysis.

 

Biodegradation in water

Various predicted data for the target compound N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methyl methanaminium acetate(CAS No. 83803-79-6) and supporting weight of evidence studies for its closest read across substance based on structural similarity and with logKow as the primary descriptor were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(CAS No. 83803-79-6) was estimated.Test substance undergoes 25.65% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene) cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compoundN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(CAS No. 83803-79-6) in the presence of mixed populations of environmental microorganisms was estimated.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 as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetateis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from peer reviewed journal (H. Heukelekian and M. C. Rand, 1955) for the read across chemical [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride (CAS no. 569-64-2),biodegradation experiment was conducted for 5 days for evaluating the percentage biodegradability of read across substance [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride using standard dilution method at a temperature of 20°C. Sewage was used as a test inoculum. The 5 day BOD value of chemical [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride was determined to be 0 g/g. Thus, based on this value, [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of the same read across substance [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride (CAS no. 569-64-2) (EnviChem, 2014). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I). Activated sludge was used as a test inoculums for the study. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride was determined to be 0.3% by BOD parameter in 14 days. Thus, based on percentage degradation, [4-[α-[4-(dimethylamino)phenyl]benzylidene]cyclohexa-2,5-dien-1-ylidene]dimethylammonium chloride is considered to be not readily biodegradable in nature.

 

For the read across chemical N-(1-methylheptyl)-N'-phenylbenzene-1,4-diamine (CAS no. 15233-47-3), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance N-(1 -methylheptyl)-N'-phenylbenzene-1,4 –diamine (J-CHECK, 2017). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively.The percentage degradation of test substance was determined to be4 and 0% degradation by O2 consumption and HPLC parameter in 28 days.The test substance was partially changed in test system to form 2% of 4- Hydroxy diphenylamine (not highly bioaccumulative), 5 to 8% of 1-Methylheptylamine and less than 1 % of N-phenyl-p-benzo quinonimine (not highly bioaccumulative). In addition, 4 % of Aniline (ready biodegradable) was produced only in (Activated sludge + test substance) system. Thus, based on percentage degradation, N-(1 -methylheptyl)-N'-phenylbenzene-1,4 -diamine is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methyl methanaminium acetate(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from peer reviewed journal and authoritative database J-CHECK & EnviChem), it can be concluded that the test substanceN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate can be expected to be not readily biodegradable in nature.

Biodegradation in water and sediment

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound

N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate

(CAS No. 83803 -79 -6). If released in to the environment, 0.563% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of test chemical in water is estimated to be 180 days (4320 hrs). The half-life (180 days estimated by EPI suite) indicates that the chemical is persistent in water and the exposure risk to aquatic animals is moderate to high whereas the half-life period of test chemical in sediment is estimated to be 1620.833 days (38900 hrs). Based on this half-life value, it indicates that N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene) cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate is persistent in sediment.

Biodegradation in soil

The half-life period of N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 51.7% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of test chemical in soil is estimated to be 360 days (8640 hrs). Based on this half-life value of test chemical, it is concluded that the chemical N-(4-((4-(dimethylamino)phenyl)(4 -(phenyl amino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate is persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to high.

On the basis of available information, the test substance N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methyl methanaminium acetate can be considered to be not readily biodegradable in nature.

Bioaccumulation: aquatic / sediment

Various predicted data for the target compound N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803-79-6) and supporting weight of evidence study for its read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In aprediction done using theBCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical N-(4 -((4 -(dimethylamino)phenyl) (4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No. 83803 -79 -6). The bioconcentration factor (BCF) of N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate was estimated to be 3.162 L/kg whole body w.w (at 25 deg C).

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the bioaccumulation i.e BCF for test substance N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino)naphthalen-1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate was estimated to be 601 dimensionless . The predicted BCF result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical (4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium, chloride (CAS no. 548-62-9),the bioaccumulation experiment in fish was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical (4 -(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5 -dien-1 -ylidene)dimethylammonium, chloride. The bioaccumulation factor (BCF) value was calculated using a log Kow of 0.51 and a regression-derived equation. The estimated BCF (bioaccumulation factor) valueof(4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium, chloride was determined to be 3 dimensionless.

 

For the read across chemical 4-[(4-dimethylaminophenyl)-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium chloride (CAS no. 569-64-2),bioaccumulation study in fish was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical 4 -[(4 -dimethylaminophenyl)-phenylmethylidene] cyclohexa-2,5 -dien-1 -ylidene]-dimethylazanium chloride (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using a log Kow of 0.62 and a regression-derived equation. The estimated BCF (bioaccumulation factor) valueof 4-[(4-dimethylaminophenyl)-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium chloride was determined to be 3 dimensionless.

 

On the basis of above results for target chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(from EPI suiteand CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the BCF value of test substanceN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetateranges from 3.162 –601which does not exceed the bioconcentration threshold of 2000, indicating that the chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate is not expected to bioaccumulate in the food chain.

Adsorption / desorption

Predicted data for the target compoundN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate (CAS No 83803 -79 -6) and supporting study for its read across substance were reviewed for the adsorption end point which are summarized as below:

 

In a key study from CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the adsorption coefficient i.e KOC for test substance N-(4 -((4 -(dimethylamino)phenyl)(4 -(phenylamino) naphthalen -1 -yl)methylene)cyclohexa-2,5 -dienylidene)-N-methylmethanaminium acetate (CAS No. 83803-79-6) was estimated to be 127000 L/kg (log Koc = 5.103).The predicted KOC result based on the 5 OECD principles.

 

In a supporting study from authoritative database (HSDB, 2017) for the read across chemical (4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium, chloride (CAS no. 548-62-9),adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical (4 -(4,4'-Bis(dimethylamino)benzhydry lidene)cyclohexa-2,5 -dien-1 -ylidene)dimethylammonium, chloride. The adsorption coefficient (Koc) value was calculated using a structure estimation method based on molecular connectivity indices. The adsorption coefficient (Koc) value of substance (4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium, chloride was estimated to be 610000 (Log Koc = 5.785).

 

On the basis of above overall results for target chemicalN-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate(fromCompTox Chemistry Dashboard,2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the Koc value of test substance N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetatewas estimated to be 127000 L/kg (log Koc = 5.103),indicating that the test chemical N-(4-((4-(dimethylamino)phenyl)(4-(phenylamino)naphthalen-1-yl)methylene)cyclohexa-2,5-dienylidene)-N-methylmethanaminium acetate has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.