4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid

Endpoint summary

Description of key information

Biodegradation:

Percent biodegradation of test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid was observed to be  25 %  and 32 % by  test material analysis by HPLC parameter. On the basis of percent degradation it is concluded that this test material is inherently biodegradable.

Bioaccumulation:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) is 3.162 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid is non bioaccumulative in food chain.

Transport and distribution:

Percent adsorption of test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (Acid yellow 49) was determined by analyzing test material. This test material is dye and matrix used for adsorption was obtained from Screened raw waste water from greater Cincinnati Mill Creek sewage treatment plant was used as influent (INF) to three pilot scale activated sludge biological treatment systems (Two experimental and one control). Each system consists of primary clarifier, complete mix aeration basin and secondary clarifier. Influent was spiked with test material at concentration of 1 mg/L and 5 mg/L. Then Dye analytical studies were conducted by purified dye compound in organic free influent waste water and mixed liquor. Then influent, primary influent filtrate was passed through column packed with resin. The filter paper and resin were soaked in an ammonia – acetonitrile solution and then soxhlet extracted with ammonia – acetonitrile. The extract was concentrated and brought upto 50 ml volume with methanol/dimethyl formamaide solution. All extracted samples were analyzed by HPLC with ultraviolet detector. Percent adsorption from mass balance data determined was 1 % in both low spiked high spiked samples.On the basis of percent adorption value it is concluded that this test material is shows low sorption.

Additional information

Biodegradation:

Biodegradation in water:

In a experimental study done fromChemosphere Vol 22 pp 107-119 1991 by Glenn M Shaul, Thomas J Holdsworth, Clyde R. Dempsey, and Kenneth A. Dostal in this study the biodegradability of test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (Acid yellow 49) was determined by analyzing percent recovery of test material. This test material is dye and inoculums used for biodegradation was obtained from Screened raw waste water from greater Cincinnati Mill Creek sewage treatment plant was used as influent (INF) to three pilot scale activated sludge biological treatment systems (Two experimental and one control). Each system consists of primary clarifier, complete mix aeration basin and secondary clarifier. Influent was spiked with test material at concentration of1 mg/L and 5 mg/L. Then Dye analytical studies were conducted by purified dye compound in organic free influent waste water and mixed liquor. Then influent, primary influent filtrate was passed through column packed with resin. The filter paper and resin were soaked in an ammonia – acetonitrile solution and then soxhlet extracted with ammonia – acetonitrile. The extract was concentrated and brought upto 50 ml volume with methanol/dimethyl formamaide solution. All extracted samples were analyzed by HPLC with ultraviolet detector.

 Percent recovery from mass balance data determined was 75 % in low spiked and 68 % in high spiked. On the basis of percent recovery value biodegradation of 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid was 25% and 32 %by test material analysis by HPLC parameter. On the basis of percent degradation it is concluded that this test material is inherently biodegradable.

Bioaccumulation:

Bioaccumulation: aquatic/sediments:

Predicted data studies for target chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) and experimental study for its structurally similar read across chemical have been conducted and their results are summarized below for bioaccumulation endpoint.

First weight of evidence study was by done using BCFBAF Program (v3.00) model of Estimation Program Interface (EPI suite 2017) the estimated bio concentration factor (BCF) for 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) is 3.162 L/kg wet-wt at 25 deg. c

Next weight of evidence study was done by using Bio-concentration Factor (v12.1.0.50374) module of Advanced Chemistry Development/ I-lab predictive module (2017) in this study the bio-concentration Factor at range pH 1-14  of the chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS no.12239 -15 -5) estimated to be 1.0 dimensionless.

Third weight of evidence study was done by using Scifinder database of American chemical Society (ACS 2017) in this  study the Bioconcentration factor (BCF) for test chemical  4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS No: 12239-15-5) was predicted in aquatic organisms by at pH 1-10 and temperature 25 °C .The Bioconcentration factor (BCF) of test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid at pH 1-10 and temperature 25 °C was estimated to be 1.0 dimensionless.

 

Fourth weight of evidence study was done by using Chemspider- ACD/PhysChem Suite of Royal society of Chemistry (RCS, 2017) in this study the Bioconcentration factor (BCF) of test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid at pH 5.5 and pH 7.4 was estimated to be 1.0 dimensionless. This BCF value suggests that the test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid is non bioaccumulative in aquatic organisms.

Next weight of evidence study was done 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 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS no.12239 -15 -5) was estimated to be 16.8 dimensionless . The predicted BCF result was based on the 5 OECD principles.

 Last weight of evidence study was done from authoritative database ( Jcheck, 2017) in this study the bioaccumulation test was conducted for 6 weeks for determination the bioconcentration factor (BCF) of read across chemical 2,5-dichloro-4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid (CAS no 84-57-1) on test organism Cyprinus carpio. Recovery ratio of Test water was 102 %, Fish : 61.0 %, - Limit of detection : Test water : 1st concentration area : 0.095 microg/mL, 2ndconcentration area : 0.0095 microg/mL, Fish : 5.5 microg/g .Nominal concentrations used was 1st Concentration area: 2.0 mg/L (w/v), 2nd Concentration area: 0.2 mg/L (w/v) and range finding study was carried out on Rice fish (Oryzias latipes) LC50(48h) 434 mg/L. The lipid content of fish was 3.8 % at start of exposure. Thus according to static fish test the bioconcentration factor (BCF) for read across chemical 2,5-dichloro-4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid was determined according static fish test. The BCF value was observed to be 2.8 L/kg at dose concentration 2 mg/L and ≤ 32 L/kg at dose concentration 0.2 mg/L on test organism Cyprinus carpio during 6 weeks period. Therefore it is concluded that read across chemical 2,5-dichloro-4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid is nonbioaccumulative in fish and food chain as these values are far less than 2000 criteria.

On the basis of above results for target chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) (from EPI suite, ACD labs, Sci Finder database, Chemspider and CompTox Chemistry Dashboard 2017) and for its read across chemicals (From J check) it can be concluded that the BCF value of test substance4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  ranges from 1 to 16.8 dimensionless which does not exceed the bioconcentration threshold of 2000, indicating that the chemical4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5)is expected to be nonbioaccumulative in the food chain.

Transport and distribution:

Adsorption/desorption:

Two experimental data studies and one predicted data study for target chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (Acid yellow 49) and one experimental study for its structurally similar read cross chemical have been conducted anf their results are summarized.

The first experimental study was done from Chemosphere Vol 22 pp 107-119 1991 by Glenn M Shaul, Thomas J Holdsworth, Clyde R. Dempsey, and Kenneth A. Dostal in this study the percent adsorption of test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (Acid yellow 49) was determined by analyzing test material. This test material is dye and matrix used for adsorption was obtained from Screened raw waste water from greater Cincinnati Mill Creek sewage treatment plant was used as influent (INF) to three pilot scale activated sludge biological treatment systems (Two experimental and one control). Each system consists of primary clarifier, complete mix aeration basin and secondary clarifier. Influent was spiked with test material at concentration of1 mg/L and 5 mg/L. Then Dye analytical studies were conducted by purified dye compound in organic free influent waste water and mixed liquor. Then influent, primary influent filtrate was passed through column packed with resin. The filter paper and resin were soaked in an ammonia – acetonitrile solution and then soxhlet extracted with ammonia – acetonitrile. The extract was concentrated and brought upto 50 ml volume with methanol/dimethyl formamaide solution. All extracted samples were analyzed by HPLC with ultraviolet detector. Percent adsorption from mass balance data determined was 1 % in both low spiked high spiked samples. On the basis of percent adorption value it is concluded that this test material is shows low sorption.

 

Next experimental study was done from Fresenius Environmental Bulletin, vol. 13 no.11a, 2004 by Mahir Alkan, Özkan Demirbaş and Mehmet Doğan in this study adsorption experiments were carried out by shaking 0.5 g sepiolite ( Clay mineral of white colour) samples with 50 mL aqueous solution of acid yellow 49 of desired concentration at various ionicstrengths (0.1-0.5 M NaCl solutions in water), pHs (3-11), temperatures (25-55oC)for 1 h (the required time for acid yellow 49 to reach the equilibrium concentrations). A thermostated shaker bath was used to keep the temperature constant. The initial concentrations of dye solutes, C0, were in the range of 1x10-4- 30 x10-4mol L-1. All adsorption experiments were performed at 25oC and pH 6.0 except those in which the effects of temperature and pH of the solution were investigated. At the end of the adsorption period, the solution was centrifuged for 15 min at 3000 rpm and then the concentration of the residual acid yellow 49, Ce, was determined with the help of Cary -1E-UV Visible Spectrophotometer (Varian). The adsorbed amounts of acid yellow 49 were calculated from the concentrations in solutions before and after adsorption according to the following equation

Qe= (C0-Ce) V/W

Results obtained at different pH, temperature, and ionic strength were mentioned in table 1 on the basis value obtained by both Isotherms is is concluded that the adsorbed amount of acid yellow 49 decreased with increasing pH, and increased with increasing temperature and ionic strength. If considered values obtained only at pH 6 and temperature 25 oC Adsorption coefficient Kf value by Freundlich isotherm of test chemical Acid yellow 49 obtained was 1900 dimensionless at pH 6 and at temperature 25 oC on sepiolite clay mineral. On the basis of this value it is concluded that test chemical Acid yellow 49 shows low sorption.

In next supporting study the Soil Adsorption Coefficient i.e Koc value of test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS no.12239 -15 -5) was estimated using Adsorption Coefficient module (v12.1.0.50374) program od Advanced Chemistry Development ACD/I-lab predictive module as Koc 1.0 dimensionless (log Koc= 0.0). This log Koc value indicates that the test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid has a negligible sorption to soil and therefore has rapid migration potential to groundwater.

Last study was supporting Study done from UERL laboratory (2017) in this study the adsorption coefficient Koc in soil and in sewage sludge of read across 5-amino-2-chlorobenzenesulfonic acid (CAS No.88-43-7) was determined by the Reverse Phase High Performance Liquid Chromatographic method. The reference substances were chosen according to estimated Koc range of the read cross substance and generalized calibration graph was prepared. The reference substances were 4-chloroaniline, 4-methylaniline (p-Tolouidine), Aniline, 2,5-Dichloroaniline, Xylene, Ethylbenzene, Toluene, Naphthalene, 1,2,3-trichlorobenzenewere chosen having Koc value ranging from 1.239 to 2.4.

The Log Koc value of read across chemical 5-amino-2-chlorobenzenesulfonic acid was determined to be 1.397 dimensionless at 25°C. Based on the value of log Koc it is concluded that this read cross chemical has negligible sorption to soil and sediments and therefore has rapid migration potential to ground water.

 On the basis of all the studies mentioned above it is concluded that test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid has a negligible sorption to soil and therefore has rapid migration potential to groundwater.