2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1H-benzimidazolium chloride

Adsorption / desorption

Administrative data

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Justification for type of information:

Experimental test result performed using standard OECD test guidelines

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2018

Report date:

2018

Materials and methods

Test guideline

Qualifier:

according to guideline

Guideline:

other: Adapted from IS: 2720 (Part 4)

Principles of method if other than guideline:

Reverse Phase High Performance Liquid Chromatography on Octadecyl-modified silica based stationary phase is used.
Partitioning on the column occurs in order of hydrophobicity when a suitable mobile phase is used. From relationship between the measured retention times and the adsorption coefficient on organic matter of reference substances, the sorption coefficient of the test substance is calculated.

GLP compliance:

yes

Type of method:

HPLC estimation method

Media:

soil/sewage sludge

Test material

Test material information

Constituent 1

Reference substance name:

2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1H-benzimidazolium chloride

EC Number:

249-694-9

EC Name:

2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1H-benzimidazolium chloride

Cas Number:

29556-33-0

Molecular formula:

C22H24N3O2.Cl

IUPAC Name:

2-[7-(diethylamino)-2-oxo-2H-chromen-3-yl]-1,3-dimethyl-2,3-dihydro-1H-3,1-benzimidazol-1-ium chloride

Test material form:

solid: particulate/powder

Details on test material:

- Name of test material (as cited in study report): 2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1H-benzimidazolium chloride
- Molecular formula: C22H24N3O2.Cl
- Molecular weight: 397.904 g/mol
- Smiles notation: c1([n+](c2c(n1C)cccc2)C)c1c(oc2c(c1)ccc(c2)N(CC)CC)=O.[ClH-]
- InChl: 1S/C22H24N3O2.ClH/c1-5-25(6-2)16-12-11-15-13-17(22(26)27-20(15)14-16)21-23(3)18-9-7-8-10-19(18)24(21)4;/h7-14H,5-6H2,1-4H3;1H/q+1;/p-1
- Substance type: Organic
- Physical state: Solid

Specific details on test material used for the study:

- Name of test material (as cited in study report): 2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1H-benzimidazolium chloride
- Molecular formula: C22H24N3O2.Cl
- Molecular weight: 397.904 g/mol
- Smiles notation: c1([n+](c2c(n1C)cccc2)C)c1c(oc2c(c1)ccc(c2)N(CC)CC)=O.[ClH-]
- InChl: 1S/C22H24N3O2.ClH/c1-5-25(6-2)16-12-11-15-13-17(22(26)27-20(15)14-16)21-23(3)18-9-7-8-10-19(18)24(21)4;/h7-14H,5-6H2,1-4H3;1H/q+1;/p-1
- Substance type: Organic
- Physical state: Solid
- Purity : 98.56%

Radiolabelling:

not specified

Study design

Test temperature:

25 deg.C

HPLC method

Details on study design: HPLC method:

PREPARATION PROCEDURE
Preparation of Reference substances:
Seven reference substances, 4-methylaniline(p-Tolouidine), N-methylaniline, Aniline, Xylene, Ethylbenzene,Toluene, Naphthalene were chosen having Koc value ranging from 1.9 to 2.75 Individual solutions of these reference substances were prepared in ACN with concentrations of 400 mg/l.
Urea (at concentration of 500 mg/l) was used as an unretained compound for the determination of the “dead time” t0.
K=tR -t0
t0
where
k= capacity factor,
tR= retention time of test substance and reference substance.
t0=retention time of Urea.

Batch equilibrium or other method

Analytical monitoring:

yes

Details on sampling:

A test item solution was prepared by accurately weighing 4 mg of test item and diluted with ACN up to 10 ml. Thus, the test solution concentration was 400 mg/l. The pH of test substance was 6.85.

Details on test conditions:

Chromatographic Conditions:
HPLC Model No. : Agilent Technologies,1260 Infinity
Flow Rate : 1.0ml/min
Column : ZORBAX Eclipse Plus C18, 4.6×100mm, 3.5 μm
Mobile phase : ACN: water (55:45)
Temperature : 25°C
Detector : Diode Array Detector @210nm
Injector : Autosampler
Injector volume : 10μl
Data Acquisition software : ChemStationOpen lab Control Panel

Results and discussion

Adsorption coefficient

Key result

Sample No.:

#1

Type:

log Koc

Value:

2.743 dimensionless

Temp.:

25 °C

Remarks on result:

other: other details not available

Results: HPLC method

Details on results (HPLC method):

HPLC PROCEDURE:
The solutions of the test substance and reference substances were prepared in solvent mentioned in 4.3. Each of the reference substance and test substance were analysed by HPLC at 210 nm.
After equilibration of the HPLC system, Urea was injected first, the reference substances were injected in duplicate, followed by the test chemical solution in duplicate. Reference substances were injected again after test sample, no change in retention time of reference substances was observed. Retention time tR were measured, averaged and the decimal logarithms of the capacity factors k were calculated. The graph was plotted between log Koc versus log k(Annex - 2).The linear regression parameter of the relationship log Koc vs log k were also calculated from the data obtained with calibration samples and therewith, log Koc of the test substance was determined from its measured capacity factor.

Results: Batch equilibrium or other method

Transformation products:

not specified

Any other information on results incl. tables

The Log Koc of 2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1Hbenzimidazolium chloride (CAS No. 29556-33-0) was determined to be 2.7434 dimensionless at 25°C.

Reference substance	Log koc	Rt1	Rt2	Rt3	Mean R± SD	K	Log K
Urea	NA	0.887	0.887	0.888	0.887±0.001	00	0
4-methylaniline(p- Tolouidine)	1.9	1.755	1.748	NA	1.7515±0.005	0.9746	-0.0112
N-methylaniline	2.28	2.303	2.294	NA	2.2985±0.006	1.5913	0.2018
Aniline	2.07	1.513	1.495	NA	1.504±0.013	0.6956	-0.1576
Xylene	2.58	6.241	6.232	NA	6.2365±0.006	6.031	0.7804
Ethylbenzene	2.649	6.359	6.355	NA	6.357±0.003	6.1669	0.7901
Toluene	2.369	4.378	4.382	NA	4.38±0.003	3.938	0.5953
Naphthalene	2.75	6.127	6.218	NA	6.1725±0.064	5.9589	0.7752

Test substance 2-[7-(diethylamino)-2-oxo-2H-1- benzopyran-3-yl]-1,3-dimethyl- 1H-benzimidazolium chloride		K	Log k (X axis)	Log Koc ( Y axis)  By Generalized calibration graph	Mean of Log Koc± S.D
Rt1	9.758	8.758	0.9424	2.7416	2.7434±0.002
Rt2	9.858	8.858	0.9473	2.7451

Applicant's summary and conclusion

Validity criteria fulfilled:

not specified

Conclusions:

The Adsorption Coefficient of test substance 2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1Hbenzimidazolium chloride (CAS No. 29556-33-0) was determined as per the HPLC method. The Log Koc value obtained was 2.7434 dimensionless at 25°C.

Executive summary:

The adsorption coefficient Koc in soil and in sewage sludge of test chemical 2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1Hbenzimidazoliumchloride (CAS No. 29556-33-0) was determined by the Reverse Phase High Performance Liquid Chromatographic method. The reference substances were chosen according to estimated Koc range of the test substance and generalized calibration graph was prepared. The reference substances were 4-methylaniline(p-Tolouidine), N-methylaniline, Aniline, Xylene, Ethylbenzene,Toluene, Naphthalene were chosen having Koc value ranging from 1.9 to 2.75.

The Log Koc value of test chemical 2-[7-(diethylamino)-2-oxo-2H-1-benzopyran-3-yl]-1,3-dimethyl-1Hbenzimidazoliumchloride (CAS No. 29556-33-0)

was determined to be 2.7434 dimensionless at 25°C. Based on the value of log Koc it is concluded that this test chemical has moderate sorption to soil and sediments and therefore has slow migration potential to ground water.