Registration Dossier
Registration Dossier
Please be aware that this old REACH registration data factsheet is no longer maintained; it remains frozen as of 19th May 2023.
The new ECHA CHEM database has been released by ECHA, and it now contains all REACH registration data. There are more details on the transition of ECHA's published data to ECHA CHEM here.
Use of this information is subject to copyright laws and may require the permission of the owner of the information, as described in the ECHA Legal Notice.
EC number: 616-466-9 | CAS number: 77501-63-4
Biodegradation in soil
Administrative data
Link to relevant study record(s)
Description of key information
(2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate is completely degraded in soil biotically (half-life approximately 2.2 d) with the esterase product 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate decreasing to 42 % of initial radioactivity from approximately 52 % after 1 week , and 14.5 % detected in the released carbon dioxide.
Anaerobic biodegradation of (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate led to the esterase product, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid and there were only minor differences compared to the aerobic degradation. Minor amounts of the esterase product were reduced at the nitro group, yielding 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2 -amino benzoic acid and its corresponding intramolecular ammonium salt, respectively.
Key value for chemical safety assessment
- Half-life in soil:
- 2.2 d
- at the temperature of:
- 21 °C
Additional information
The potential of soil to degrade (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate was examined in regard to 4 aspects
1. Degradation by soil fungi
2. Degradation by soil bacteria
3. Aerobic degradation in soil
4. Anaerobic degradation in soil
with the following results: 1. The degradation of (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate by eleven species of fungi widespread in soil was examined in the laboratory. All but one of the fungi species rapidly degraded (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate to a singleproduct after 120 h in shake-flask cultures at 27°C. In the sterile control, (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate was not degraded. By Thin Layer Chromatography, High Performance Liquid Chromatography and Mass Spectrometry the metabolite formed by esterase activity was demonstrated to be 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid.
2. Similarily, nine bacterial strains were tested for their potential to degrade (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate in shake flask cultures at 30°C in the laboratory.
All strains were able to degrade (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate within 7 d significantly. Two strains of Bacillus were the most effective and completely degraded the test substance. The other 7 bacterial strains were less active in (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate degradation than the fungi tested in another study of the same authors, and unreacted test substance remained after 7 d of incubation. All nine strains formed a different major metabolite.
3. Aerobic biodegradation of (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate in soil extending the examinations reported in the previous studies from 30 to 90 d of incubation.
(2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate is completely degraded in soil biotically (half-life approximately 2.2 d). After 90 d, the concentration of the identified esterase product, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, had fallen from approximately 52 % after 7 d to 42 % of the applied radioactivity of 14C-(2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate. After 90 days the 14carbon dioxide formation amounted to 14.5% of the applied radioactivity.
4. Anaerobic biodegradation of (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate in soil was followed for 30 or 60 d after 30 d of aerobic incubation in the laboratory.
After 30 or 60 d of anaerobic biodegradation (60 or 90 d in total), the esterase product, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, was found and there were only minor differences compared to the aerobic degradation. These differences were:
1. Minor amounts of the esterase product were reduced at the nitro group, yielding 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2 -amino benzoic acid and its corresponding intramolecular ammonium salt, respectively.
2. Carbon dioxide release amounted only 3.4 % suggesting the formation of additional transformation/degradation intermediates
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.
