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EC number: 248-742-6 | CAS number: 27939-60-2
Biodegradation in water and sediment: simulation tests
Administrative data
Link to relevant study record(s)
Description of key information
Based on DRAFT report OECD TG 309
In accordance with OECD TG 309 the time course of biodegradation of a test substance in aerobic natural water at 12°C is determined at 10 and 100 µg/l. The parent substance Vertoliff disappeared within minutes (<1 day) and turned into Vertoliff-acid/alcohol(s) (ROI 7), which remained stable for 14 days in the low and high concentration groups. Thereafter primarily further oxidation products were found (ROI 6 to ROI 1) and one reduction reaction towards Vertoliff-alcohol (ROI 8).
The low mineralisation of Vertoliff required identification by means of log Kow (HPLC, OECD TG 117) for all metabolites (ROIs) when exceeding the 10% level (OECD TG 309, 40). In both low and high treatment groups ROI 8, 7, 6 and 5 all decreased to <10%, mostly show a decreasing trend and therefore do not need to be considered further. In the high treatment group only ROI 4 is above 10% but shows a decreasing trend in the low treatment group. This ROI has a log Kow of 1.95, which is <2. In the low treatment group ROI 3 is just above 10% and shows a decreasing trend in both low and high treatment groups. ROI 3 has a log Kow of 1.8, which is <2. In both low and high treatment groups ROI 2 and 1 are well above 10% and increase from day 28 onwards. The log Kow of these ROIs are 1.77 and 1.5, respectively.
Key value for chemical safety assessment
- Half-life in freshwater:
- 0.063 d
- at the temperature of:
- 12 °C
Additional information
Biodegradation in a Water-Simulation test – Based on DRAFT Report
Introduction
To address the potential PBT profile of Vertoliff based on potential bioaccumulation for air-breathing organism, a biodegradation study was performed. The mineralisation and transformation of the substance was studied in the guideline study 'Aerobic Mineralisation in Surface Water – Simulation Biodegradation Test' according to OECD TG 309 and in compliance with GLP. In addition, log Kow values of transformation products have been determined using the OECD TG 117 HPLC test guideline, using reference compounds. The transformation products will be discussed with the focus on those exceeding the 10% at day 63 and showing an increasing trend (OECD TG 309) and the log Kow exceeding the value of 2, which is a relevant value for the bioaccumulation in air-breathing organisms (ECHA-guidance on PBT, 2017).
Method
Natural lake water was utilised in the study. Water was dosed with 14C-labeled Vertoliff at actual concentrations of 10.5 µg/L and 108 µg/L. Sterilised water dosed at 100 µg/L was included to evaluate transformation in the absence of water microorganisms. A control group treated with [14C]benzoic acid (~10 µg/L) was included to evaluate viability and activity of the microbial population.
Test vessels were sealed with crimp caps and septa after treatment, and were incubated with continuous shaking for up to 63 days at 12°C. Aerobic conditions were monitored by dissolved oxygen measurements in control vessels. At each sampling interval, vessels selected for analysis were attached to an air flow-through system designed to purge vessel headspace with air and collect 14C volatile gases and 14CO2 with the exception of Day 0. Effluent gases were passed through ethylene glycol to trap organic volatiles, followed by an alkali solution to trap evolved carbon dioxide.
Duplicate live test vessels of each dose level were sacrificed on Day 0, 2 and 4 hours, Day 1, 7, 14, 28, 42 and 63. Duplicate sterile vessels were sacrificed on Days 0, 28, and 63. Reference substance (benzoic acid) vessels were assessed for 14C gas production on Days 7, 14, and 28. Water samples were processed by diluting with acetonitrile (ACN) to stabilise and the diluted waters were analysed for total radioactivity by liquid scintillation counting (LSC). The radioactive distributions of parent substance and associated metabolites were determined by high performance liquid chromatography with a radiometric detection (HPLC-β-RAM).
Octanol-water partition coefficient (Kow) was determined using the HPLC method. The values of the log Kow was determined for all transformation product peaks using samples from high treatment group from day 14 and day 28.
Results
The water layer recoveries and material balances were quantitative during the study (91.9%-103.2%). Recoveries of 14CO2 and 14C volatile products were minimal, indicating that no or very little mineralisation occurred during the study. Mineralisation in the viability controls demonstrated that the microbial population was viable and active during the study.
In the abiotic system Vertoliff completely disappeared by Day 28 because oxidation reaction(s) occurred in the parent test substance. The by-products Vertoliff acid/alcohol metabolites were detected in retention time regions-of-interest (ROI 7) at all intervals in the abiotic vessels (Table 1).
In the biotic system a similar oxidation reaction occurred rapidly in the parent test substance (ROI 7) and further bio-transformation was observed in both the low and high concentration groups. In the low treatment group (10 ug/l), at day 63, major transformation products (>10% AR) were seen in three regions of interest (ROI 3, 2 and 1). Other transformation products were either transient (only reaching 10% AR at one interval) or never reached 10% AR (Table 2). In the high treatment group (100 ug/l), at day 63, major transformation products (>10% AR) were seen in three regions of interest (ROI 4, 2 and 1). Other transformation products were either transient (only reaching 10% AR at one interval) or never reached 10% AR (Table 3).
The calculated DT50 and DT90 for [14C]Vertoliff from the low treatment group (10 µg/L) were 0.0041 and 0.0136 days, respectively. The calculated DT50 and DT90 for [14C]Vertoliff from the high treatment group (100 µg/L) were 0.0631 and 0.21 days, respectively. Modelling the transformation products’ data resulted in very poor fits, and were therefore not reported.
Chromatographically, all transformation products were eluting in the polar regions preceding the parent material. The octanol-water partition coefficient (Kow) of ROI 9 is 2.9, ROI 7 (2 combined peaks) is 2.8, ROI 6 and 5 have log Kows of 2.2 and 2.1, respectively. ROI 4, 3, 2 and 1 have log Kows of 1.95, 1.82. 1.77 and 1.50, respectively.
Table 1
Mean Distribution of Parent and Transformation Products in Test Systems
Treated with [14C]Vertoliff at 100 µg/L
Abiotic Test Systems, 12 °C
| Regions of Interest (ROI, % AR) |
|
| ||||||||
| ROI1 | ROI2 | ROI3 | ROI4 | ROI5 | ROI6 | ROI7 | ROI8 | Vertoliff | Total | Total |
Test | Met1 | Met2 | Met3 | Met4 | Met5 | Met6 | Met7/8 | Met9 | Parent | Trans. | 14C |
Day | ~2.1-3.5 | ~4.0-5.4 | ~5.9-6.9 | ~6.9-8.3 | ~8.6-9.5 | ~9.8-10.4 | ~15.2-16.8 | ~17.0-17.8 | ~21.1-21.9 min. | Products |
|
0 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 10.5% | 0.0% | 92.0% | 10.5% | 102.4% |
28 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 93.5% | 0.0% | 0.0% | 94.2% | 94.2% |
63 | 4.0% | 0.0% | 0.0% | 3.2% | 1.0% | 1.1% | 85.9% | 0.0% | 0.0% | 96.2% | 96.2% |
All calculations performed in Excel 2016 in full precision mode. Manual calculations may differ slightly.
Table 2
Mean Distribution of Parent and Transformation Products in Test Systems
Treated with [14C]Vertoliff at 10 µg/L
Biotic Test Systems, 12 °C
| Regions of Interest (ROI, % AR) |
|
| ||||||||
| ROI1 | ROI2 | ROI3 | ROI4 | ROI5 | ROI6 | ROI7 | ROI8 | Vertoliff | Total | Total |
Test | Met1 | Met2 | Met3 | Met4 | Met5 | Met6 | Met7/8 | Met9 | Parent | Trans. | 14C |
Day | ~2.1-3.5 | ~4.0-5.4 | ~5.9-6.9 | ~6.9-8.3 | ~8.6-9.5 | ~9.8-10.4 | ~15.2-16.8 | ~17.0-17.8 | ~21.1-21.9 min. | Products |
|
0 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 100.8% | 0.0% | 100.8% |
0.083 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 96.6% | 0.0% | 0.0% | 96.6% | 96.6% |
0.167 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 98.3% | 0.0% | 0.0% | 98.3% | 98.3% |
7 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 98.5% | 0.0% | 0.0% | 98.5% | 98.5% |
14 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 99.3% | 0.0% | 0.0% | 99.3% | 99.3% |
28 | 24.1% | 13.0% | 17.5% | 10.4% | 3.8% | 13.2% | 7.1% | 10.6% | 0.0% | 99.8% | 99.8% |
42 | 29.8% | 18.2% | 11.2% | 9.6% | 8.4% | 1.5% | 6.3% | 7.4% | 0.0% | 93.2% | 93.2% |
63 | 36.9% | 22.4% | 10.2% | 6.0% | 8.9% | 2.3% | 5.0% | 7.5% | 0.0% | 99.2% | 99.2% |
All calculations performed in Excel 2016 in full precision mode. Manual calculations may differ slightly.
Table 3
Mean Distribution of Parent and Transformation Products in Test Systems
Treated with [14C]Vertoliff at 100 µg/L
Biotic Test Systems, 12 °C
| Regions of Interest (ROI, % AR) |
|
| ||||||||
| ROI1 | ROI2 | ROI3 | ROI4 | ROI5 | ROI6 | ROI7 | ROI8 | Vertoliff | Total | Total |
Test | Met1 | Met2 | Met3 | Met4 | Met5 | Met6 | Met7/8 | Met9 | Parent | Trans. | 14C |
Day | ~2.1-3.5 | ~4.0-5.4 | ~5.9-6.9 | ~6.9-8.3 | ~8.6-9.5 | ~9.8-10.4 | ~15.2-16.8 | ~17.0-17.8 | ~21.1-21.9 min. | Products |
|
0 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 10.6% | 0.0% | 90.3% | 10.6% | 100.9% |
0.083 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 64.6% | 0.0% | 33.4% | 64.6% | 98.0% |
0.167 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 79.4% | 0.0% | 17.7% | 79.4% | 97.1% |
7 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 97.2% | 0.0% | 0.0% | 97.2% | 97.2% |
14 | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 96.1% | 0.0% | 0.0% | 96.1% | 96.1% |
28 | 14.5% | 19.0% | 0.0% | 15.1% | 10.4% | 17.9% | 9.0% | 10.5% | 0.0% | 96.3% | 96.3% |
42 | 28.6% | 12.3% | 6.9% | 12.7% | 7.1% | 10.7% | 6.1% | 7.1% | 0.0% | 92.2% | 92.2% |
63 | 31.6% | 14.3% | 4.5% | 13.3% | 7.5% | 9.9% | 6.2% | 7.5% | 0.0% | 95.9% | 95.9% |
All calculations performed in Excel 2016 in full precision mode. Manual calculations may differ slightly.
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