2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride

Endpoint summary

Description of key information

Hydrolysis:

Hydrolysis of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) was predicted using OECD QSAR toolbox version 3.3 (2017). The estimated half-life of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be 147.8 days, indicating that 2-[2-[4- [(2-chloroethyl)- ethylamino]-o-tolyl]vinyl]-1 ,3,3-trimethyl-3H-indolium chloride was non hydrolysable.

Biodegradation in water:

Study was conducted to determine the degradation of chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride by the methanogenic bacteria. Anaerobic granular sludge was used in the test. Serum vials (120 ml total volume) with butyl rubber stoppers were used to test the biodegradability of the dyes. Anaerobic granular sludge sampled from a UASB reactor fed with soft-drink wastewater was added as active biomass. The basal medium M9 was used with laboratory grade yeast extract (1 g/l), trypticase (1 g/l), sodium acetate (2 g/l); a microelements solution. All modification was carried out in an anaerobic chamber. The autoclaved medium was aliquoted in the vials (50 ml/each). Test conducted at various concentrations 0, 300, 600, 1200 and 2400 mg/l. The gas phase in the vials was replaced by pure O,-free sterile nitrogen. For each dye and each concentration four replicate vials were prepared. Methane and hydrogen production were monitored in each vial every 24 h for 3 or 4 days. As the chemical shows high toxicity on the methanogenic bacteria (anaerobic granular sludge) and kill 100% bacterial growth at all the concentrations after 72hrs, thus no biodegradation was observed by the bacteria. Based on the result, 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride was not biodegradable.

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 2-[2-[4-[(2-chloroethyl)ethylamino] -o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (CAS No. 6441 -82 -3). The bioconcentration factor (BCF) of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl] vinyl]-1,3,3-trimethyl-3H-indolium chloride  was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride is expected to not bioaccumulate in the food chain.

Adsorption:

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 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride was estimated to be 8100 L/kg (Log Koc = 3.908). The predicted KOC result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride is have strong sorption to soil and sediment, negligible to slow migration potential to ground water.

Additional information

Hydrolysis:

Various predicted and experimental data for the target compound 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]- 1,3,3-trimethyl-3H-indolium chloride (CAS No. 6441 -82 -3) and supporting weight of evidence studies for its closest read across substance with logKow as the primary descriptor were reviewed for the hydrolysis end point which are summarized as below:  

 

In the first weight of evidence study, hydrolysis of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) was predicted using OECD QSAR toolbox version 3.3 (2017). The estimated half-life of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be 147.8 days, indicating that 2-[2-[4-[(2-chloroethyl)- ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was non hydrolysable.

Similarly second study was conducted on the read across chemical which was selected on the basis of logKow as the primary descriptor. Chemical 1,2,3-Trichloropropane (96-18-4) from authoritative database study was conducted for the estimation of hydrolysis rate constant and Half-life of hydrolysis at pH 7 of test chemical 1,2,3-Trichloropropane by base catalyzed first order reaction and structure estimation method. The hydrolysis rate constant of chemical 1,2,3-Trichloropropane was 1.8X10-6 /h based on the first order reaction. The half-life of hydrolysis obtained at pH 7 was 44 years. Since half-life of hydrolysis at pH is more than 10 days so it is concluded that test chemical 1,2,3-Trichloropropane was non hydrolyzing.

 

Similarly third study was conducted on another read across chemical 1,2-Dibromethan (106-93-4) which was selected on the basis of logKow as the primary descriptor. To estimate hydrolysis rate constant and Half-life of hydrolysis at pH 7 of test chemical 1,2-Dibromethan at 60degree C. The aqueous hydrolysis rate constant for ethylene dibromide was measured at pH 7 to be 0.00187/hr at 60 deg C. The half-life of 1,2-Dibromethan obtained at pH 7 was 15.44 days. Since half-life of hydrolysis at pH 7 is more than 10 days so it is concluded that test chemical 1,2-Dibromethan was non hydrolyzing.

 

Thus based on the above data for the target chemical and read across chemical it was concluded that the chemical was not hydrolysable as it exceeds the half-life of at pH 7 is more than 10 days.

 

 

Biodegradation in water:

Various predicted and experimental data for the target compound 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) and supporting weight of evidence studies for its closest read across substance with logKow as the primary descriptor were reviewed for the biodegradation end point which are summarized as below:

In a first experimental report for the 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride done by Bioresource Technology, 1998 biodegradation study was conducted. Study was conducted to determine the degradation of chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride by the methanogenic bacteria. Anaerobic granular sludge was used in the test. Serum vials (120 ml total volume) with butyl rubber stoppers were used to test the biodegradability of the dyes. Anaerobic granular sludge sampled from a UASB reactor fed with soft-drink wastewater was used as active biomass. The basal medium M9 was used with laboratory grade yeast extract (1 g/l), trypticase (1 g/l), sodium acetate (2 g/l); a microelements solution. All modification was carried out in an anaerobic chamber. The autoclaved medium was aliquoted in the vials (50 ml/each). Test conducted at various concentrations 0, 300, 600, 1200 and 2400 mg/l. The gas phase in the vials was replaced by pure O,-free sterile nitrogen. For each dye and each concentration four replicate vials were prepared. Methane and hydrogen production were monitored in each vial every 24 h for 3 or 4 days. As the chemical shows high toxicity on the methanogenic bacteria (anaerobic granular sludge) and kill 100% bacterial growth at all the concentrations after 72hrs, thus no biodegradation was observed by the bacteria. Based on the result, 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride was not biodegradable.

 

In the second supporting study using Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the test compound   2-[2-[4-[(2-chloroethyl) ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl- 3H-indolium chloride (CAS no.6441 -82 -3) 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 as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that the test chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl] -1,3,3-trimethyl-3H-indolium chloride is expected to be not readily biodegradable.

 

In the third supporting study for the target chemical, study was done (SSS) using Biodegradability of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (CAS no.6441 -82 -3) is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 0.58000 % degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride was estimated to be not readily biodegradable in water.

 

Similarly another biodegradation study for read across chemical (127-90-2) which was similar to the target chemical (from authoritative database J-CHECK, 2017), was conducted. 14 days of biodegradation study was conducted for evaluating the percentage biodegradability of test substance 1,1,1,2-tetrachloro-3-(2,3,3,3-tetrachloropropoxy)propane. 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 0 and 6.8 % by BOD and GC parameter in 14 days. Thus, based on percentage degradation, 1,1,1,2-tetrachloro- 3-(2,3,3,3-tetrachloropropoxy)propane is considered to be not readily biodegradable in water.

 

Similarly another biodegradation study for read across chemical (2939-80-2) which was similar to the target chemical (from authoritative database J-CHECK, 2017), was studied. Biodegradation study was conducted for evaluating the percentage biodegradability of test substance (3aS,7aR)-2-(1,1,2,2-tetrachloroethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione. 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 0 and 36 % by BOD and GC parameter in 28 days. Thus, based on percentage degradation, (3aS,7aR)-2- (1,1,2,2-tetrachloroethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione is considered to be not readily biodegradable in water.

 

On the basis of above results for target chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride (6441 -82 -3) (from peer reviewed journal, OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance peer reviewed journal and authoritative from database J-CHECK, it can be concluded that the test substance 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride can be expected to be not readily biodegradable in nature. 

 

Bioaccumulation: aquatic / sediment:

Various predicted data for the target compound 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]- 1,3,3-trimethyl-3H-indolium chloride (CAS No. 6441 -82 -3) study has been reviewed for the bioaccumulation end point which are summarized as below:

 

In the first predicted study from BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]- 1,3,3-trimethyl-3H-indolium chloride (CAS No. 6441 -82 -3). The bioconcentration factor (BCF) of 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl] vinyl]-1,3,3-trimethyl-3H-indolium chloride  was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride is expected to not bioaccumulate in the food chain.

 

Similarly another supporting 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 bioaccumulation i.e BCF for test substance 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride was estimated to be 636 dimensionless . The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride is non-bioaccumulative in nature.

 

On the basis of available information, the test 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride can be considered to be nonbioaccumulative in nature.

 

Adsorption:

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 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3- trimethyl-3H-indolium chloride was estimated to be 8100 L/kg (Log Koc = 3.908). The predicted KOC result based on the 5 OECD principles.

 

Thus based on the result it is concluded that the test substance 2-[2-[4-[(2-chloroethyl)ethylamino]-o-tolyl]vinyl]-1,3,3-trimethyl-3H-indolium chloride is have strong sorption to soil and sediment, negligible to slow migration potential to ground water.