2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-4-methanol

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2015-10-07 to 2016-01-07

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

EU Method C.19 (Estimation of the Adsorption Coefficient (KOC) on Soil and Sewage Sludge Using High Performance Liquid Chromatography (HPLC))

Deviations:

no

Qualifier:

according to guideline

Guideline:

OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC))

Deviations:

no

Qualifier:

according to guideline

Guideline:

other: European Commission (EC), Technical Guidance Document on Risk Assessment Part III, Chapter 4.3: “Use of (Quantitative) Structure Activity Relationships ((Q)SARs) - Soil and Sediment Sorption”, 2003.

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Remarks:

See study report

Type of method:

HPLC estimation method

Media:

other: HPLC column

Specific details on test material used for the study:

SOURCE OF TEST MATERIAL
- Source and lot/batch No.of test material:
* identification: JNJ-16479489-AAA (T001159)
* Batch: M14IB5308
- Expiration date of the lot/batch: 2016-02-03 (retest date)
- Purity test date: 2015-04-23

STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material: At room temperature

Radiolabelling:

no

Details on study design: HPLC method:

EQUIPMENT
- Apparatus: Acquity UPLC system (Waters, Milford, MA, USA)
- Type: Acquity UPLC TUV detector (Waters)
- Type, material and dimension of analytical (guard) column:
* Column: Acquity UPLC HSS Cyano, 100 mm x 2.1 mm i.d., dp = 1.8 µm (Waters)
* Column temperature: 35°C ± 1°C
* Flow: 0.4 mL/min
* Injection volume: 10 µL
- Detection system: 210 nm (UV)

MOBILE PHASES
- Type: 55/45 (v/v) methanol/0.01 M phosphate buffer at pH 8
- Solutes for dissolving test and reference substances:
* Solution of the unretained compound:
A 5.0 g/L stock solution of formamide (99.2%, [75-12-7], Alfa Aesar, Karlsruhe, Germany) in methanol was used. The stock solution was diluted to obtain an end solution of 55/45 (v/v) methanol/0.01 M phosphate buffer pH 8.
The formamide blank solution was 55/45 (v/v) methanol/0.01 M phosphate buffer pH 8.
* Reference substance solutions:
Stock solutions of the reference substances at concentrations of approximately 1 g/L in methanol were used. The stock solutions were diluted to obtain an end solution of 55/45 (v/v) methanol/0.01 M phosphate buffer pH 8.
The blank solution for the mixture of reference substances was 55/45 (v/v) methanol/0.01 M phosphate buffer pH 8
* Test solution:
A 2000 mg/L stock solution of the test item was prepared in methanol. The stock solution was diluted to obtain an end solution of 55/45 (v/v) methanol/0.01 M phosphate buffer pH 8. The final concentration of the test item solution was 10.0 mg/L.
The test item blank solution was 55/45 (v/v) methanol/0.01 M phosphate buffer pH 8.

REFERENCE SUBSTANCES
- Identity: combined reference solution containing Acetanilide, Monuron, 2,5-Dichloroaniline, Nahtalene, Benzoic acid phenylester, Fenthion, Phenanthrene and 4,4'-DDT.

DETERMINATION OF RETENTION TIMES
- Quantity of test substance introduced in the column: 10.0 mg/L
- Quantity of reference substances: 1 g/L in methanol
- Intervals of calibration: no data

REPETITIONS
- Number of determinations: The reference substance and test item solutions were injected in duplicate. Blank solutions were analysed by single injection.

EVALUATION
- Calculation of capacity factors k': from retention time of reference items, the test item, and then on-sorbed chemical item
- Determination of the log Koc value: a correlation of log k' versus log Koc of the reference items is plotted using linear regression - the log k' value of the test item is then used to calculate its log Koc value

Analytical monitoring:

no

Key result

Type:

Koc

Value:

510 dimensionless

pH:

8

Key result

Type:

log Koc

Value:

2.7 dimensionless

pH:

8

Key result

Type:

Koc

Value:

> 430 000 dimensionless

pH:

7

Key result

Type:

log Koc

Value:

> 5.63 dimensionless

pH:

7

Details on results (HPLC method):

- Retention times of reference substances used for calibration:
- At test pH 8
* Formamide (t0): tr1 = 0,693min; tr2= 0,692min
* Acetanilide: tr1 = 0,866min; tr2= 0,885min
* Monuron: tr1 = 1,075min; tr2= 1,074min
* 2,5-Dichloroaniline: tr1 = 1,195min; tr2= 1,197min
* Naphthalene: tr1 = 1,39min; tr2= 1,392min
* Benzoic acid phenylester: tr1 = 1,652min; tr2= 1,651min
* Fenthion: tr1 = 2,089min; tr2= 2,091min
* Phenanthrene: tr1 = 2,323min; tr2= 2,322min
* 4,4’-DDT: tr1 = 5,285min; tr2= 5,284min

- At neutral pH 7
* 4,4’-DDT tr1=7.043min; tr2= 7.063min

- Details of fitted regression line (log k' vs. log Koc): log k' = 0.311 x log Koc - 0.864 (r = 0.98, n = 16)
- Average retention data for test substance:
* At test pH 8: tr1 = 1,35min; tr2= 1,349 min
* At neutral pH 7: tr1=11.806 min; tr2= 11.964 min

Transformation products:

not measured

Calculation of pKa values

The following pKa values in the logarithm range of 1 - 14 for acidic and basic groups in the molecular structure of the test item were calculated using the Perrin calculation method:

Acidic groups: No pKa values

Basic group:

 1 -SUBST.-IMIDAZOLE: pKa 6.04

Validity criteria fulfilled:

yes

Conclusions:

The determination of the adsorption coefficient (Koc) of JNJ-16479489-AAA (T001159) was performed according to the OECD 121. The HPLC method using soil-adsorption-reference data was applied.
The Koc at pH 7 was >4.3 x 10^5 and the log Koc was > 5.63. The results of the test can be considered reliable without restriction.

Description of key information

One study (Reingruber, 2016) was performed according to OECD guideline 121 and the EEC Directive 2001/59, C.19 and given a Klimisch score of 1. The HPLC method using soil-adsorption-reference data was applied for the determination of the adsorption coefficient (Koc) of JNJ-16479489-AAA (T001159). At neutral pH, the log Koc was > 5.63.

Key value for chemical safety assessment

Koc at 20 °C:

430 000

Other adsorption coefficients

Type:

log Kp (solids-water in suspended matter)

Value in L/kg:

4.63

at the temperature of:

20 °C

Other adsorption coefficients

Type:

log Kp (solids-water in sediment)

Value in L/kg:

4.33

at the temperature of:

20 °C

Other adsorption coefficients

Type:

log Kp (solids-water in soil)

Value in L/kg:

3.93

at the temperature of:

20 °C

Additional information

[LogKoc: 5.63]