Table 1. Parent Compounds (P) and Metabolites (M1, M2 and M3) As Well As Metabolite Enrichment Factors (MEFs) for Metabolites and Bioaccumulation Factors (BAFs) for Parent Compounds.
| parent compound (CAS number) |
log Kowa and pKa values [-] | molecules (in order of increasing
retention time for each compound) |
method of detection and identification | MEF or BAF [L/kgwet weight] |
|---|---|---|---|---|
| imidacloprid (CAS 138261-41-3) |
0.33 (pKa = 11.12) | no metabolites detected | Radio-HPLC | BAFP = 7f |
| ethylacrylate (CAS 140-88-5) |
1.32 | no metabolites detectedd | Radio-HPLC | BAFP = 87f |
| 4,6-dinitro-o-cresol (CAS 534-52-1) |
2.22 (pKa = 4.46) | no metabolites detected | Radio-HPLC | BAFP = 37f |
| 1,2,3-trichlorobenzene (CAS 87-61-6) |
4.05 | no metabolites detected | Radio-HPLC | BAFP = 191f |
| malathion (121-75-5) |
2.36 | M1: not identified | Radio-HPLC | MEFM1 = 5 |
| P: malathion + malaoxone | HPLC-radio/UV | BAFP = 3 | ||
| chlorpyrifos (CAS 2921-88-2) |
4.96 | M1: not identified | Radio-HPLC | MEFM1 = 492 |
| M2: chlorpyrifos-oxon | HPLC-radio/UV | MEFM2 = 183 | ||
| P: chlorpyrifos | HPLC-radio/UV | BAFP = 412 | ||
| aldicarb (CAS 116-06-3) |
1.13 | M1: aldicarb-sulfone | HPLC-radio/UV | MEFM1 = 0.3 |
| P: aldicarb | HPLC-radio/UV | BAFP = 0.9 | ||
| carbofuran (CAS 1563-66-2) |
2.32 | M1: hydroxy-carbofuran | HPLC-radio/UV | MEFM1 = 69 |
| P: carbofuran | HPLC-radio/UV | BAFP = 0.7 | ||
| carbaryl (CAS 63-25-2) |
2.36 | M1: naphtol-sulfate | Radio-HPLC, Orbitrap | MEFM1 = 153 |
| P: carbaryl + naphtolc | HPLC-radio/UV | BAFP = 4 | ||
| 2,4-dichlorophenol (CAS 120-83-2) |
3.17 (pKa = 7.97) | M1: 2,4-dichlorophenol-sulfateb | Radio-HPLC, Orbitrap | MEFM1 = 195 |
| M2: not identified | Radio-HPLC | MEFM2 = 14 | ||
| P: 2,4-dichlorophenol | HPLC-radio/UV | BAFP = 4 | ||
| 2,4,5-trichlorophenol (CAS 95-95-4) |
3.72 (pKa = 6.94) | M1: 2,4,5-trichlorophenol-sulfate | Radio-HPLC, Orbitrap | MEFM1 = 1454 |
| M2: not identified | Radio-HPLC | MEFM2 = 109 | ||
| P: 2,4,5-trichlorophenol | HPLC-radio/UV | BAFP = 82 | ||
| pentachlorophenol (CAS 87-86-5) |
5.18 (pKa = 4.72) | M1: not identified | Radio-HPLC | MEFM1 = 318 |
| P: pentachlorophenol | Radio-HPLC | BAFP = 202 | ||
| 4-nitrobenzyl-chloride (CAS 100-14-1) |
2.61 | M1: not identified | Radio-HPLC | MEFM1 = 15 |
| M2: 4-nitrobenzyl-alcohol | HPLC-radio/UV | MEFM2 = 50 | ||
| M3: not identified | Radio-HPLC | MEFM3 = 87 | ||
| P: 4-nitrobenzyl-chloride | HPLC-radio/UV | BAFP = 5 | ||
| 2,4-dichloroaniline (CAS 554-00-7) |
2.78 | M1: not identified | Radio-HPLC | MEFM1 = 58 |
| M2: not identified | Radio-HPLC | MEFM2 = 22 | ||
| P: 2,4-dichloroaniline | HPLC-radio/UV | BAFP = 29 | ||
| sea-nine (CAS 64359-81-5) |
2.8 | M1: not identified | Radio-HPLC | MEFM1 = 35 |
| M2: not identified | Radio-HPLC | MEFM2 = 316 | ||
| P: sea-nine | Radio-HPLC | BAFP = 272 | ||
| M3: not identified | Radio-HPLC | MEFM3 = 37 |
Experimental log KOW values from Sangster’s database37 and from Jacobson and Williams38 for sea-nine. For 4-nitrobenzyl-chloride, no experimental value was available; thus, we calculated it with the EPI suite KowWin software (http://epa.gov/oppt/exposure/pubs/episuite.htm). The pKa values were also taken from Sangster’s database (http://logkow.cisti.nrc.ca/logkow/).
Sulfate must be metabolite 1 because orbitrap likely detected the largest peak only.
Peaks of carbaryl and naphtol cannot be separated; naphtol was likely formed during sample preparation.
Ethylacrylate reacts with methanol during sample preparation (spiked samples). We did not observe any peaks of potential biotransformation products that were distinguishable from the artifact peaks of this adduct.
The peaks of malathion and malaoxon could not be clearly separated in the biotransformation kinetics experiment. Both peaks also come closely after each other in the HPLC-UV chromatogram.
Bioaccumulation factors for compounds that were not biotransformed are taken from ref (11).