Environmental Photochemistry of Fluoroquinolones in Soil and in Aqueous Soil Suspensions

Environmental photochemistry of Fluoroquinolones in soil and in aqueous soil suspensions under solar light

Environmental Science and Pollution Research

Michela Sturinia*, Andrea Speltinia*, Federica Maraschia, Luca Pretalib, Antonella Profumoa, Elisa Fasania, Angelo Albinia

a Department of Chemistry, University of Pavia, via Taramelli 12, 27100 Pavia, Italy

b Institute for Organic Synthesis and Photoreactivity, National Research Council (ISOF-CNR), via Gobetti 101, 40129 Bologna, Italy

*Corresponding authors. Tel.: + 39 0382-987347; Fax: + 39 0382-98528544

E-mail addresses: ,

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF CIP (Film)

Fragment / HPLC/ESI-MS/MS
comp. CIP51 / comp. CIP61 / comp. CIP1 / CIP
m/e / int. / m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 263.15 / 12 / 334.16 / 6 / 306.16 / 12 / 332.22 / 2
[M+1-NH3]+ / 317.21 / 100
[M+1-H2O]+ / 245.14 / 100 / 288.28 / 100 / 314.19 / 4
[M+1-CO2]+ / 288.22 / 100
[M+1-CHO2]+ / 217.17* / 100 / 327.27 / 100
[M+1-CH3NO2]+ / 273.19* / 100
[M+1-CHFO2]+ / 268.24* / 100
[M+1-C2H5N]+ / 263.19 / 28
[M+1- C2H3O2]+ / 203.26* / 92
[M+1-C4H6FN]+ / 245.24* / 70
[M+1-C5H8FN]+ / 231.24* / 20
[M+1-C7H10FN]+ / 205.22* / 12

*MS/MS/MS

1Appl.Cat.B, J. Environ. Monit 05

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF CIP (Soil)

Fragment / HPLC/ESI-MS/MS
comp. CIP11 / comp. CIP2 / comp. CIP3
m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 306.12 / 60 / 360.22 / 1 / 376.18 / 2
[M+1-OH]+ / 289.01* / 70 / 359.14 / 100
[M+1-H2O]+ / 288.17 / 100 / 342.29 / 4
[M+1-H2FN]+ / 271.06* / 100
[M+1-H3FO]+ / 344.27* / 20
[M+1-CO2]+ / 316.22 / 100 / 332.19 / 25
[M+1-CFNO]+ / 315.17 / 95
[M+1-C2H4FN]+ / 245.18* / 20
[M+1-C2H2FNO2]+ / 288.22* / 10
[M+1-C3H2FNO2]+ / 257.08* / 7
[M+1-C4H2FNO2]+ / 245.10* / 100

*MS/MS/MS

1Appl.Cat.B, , J. Environ. Monit 05

Fragment / HPLC/ESI-MS/MS
CIP / comp. CIP41
m/e / int. / m/e / int.
[M+1]+ / 332.25 / 1 / 346.16 / 3
[M+1-H2O]+ / 314.29 / 4 / 328.26 / 5
[M+1-CO2]+ / 288.14 / 100 / 302.16 / 100
[M+1-CHFO2]+ / 268.17* / 100 / 282.19* / 20
[M+1-C3H5NO2]+ / 245.15* / 70
[M+1-C3H3NO3]+ / 245.14* / 100
[M+1-C4H5NO3]+ / 231.18* / 12
[M+1-C4H7NO2]+ / 231.12* / 20
[M+1-C6H9NO2]+ / 205.07* / 15

*MS/MS/MS

1Appl.Cat.B, , J. Environ. Monit 05

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF DAN (Film)

Fragment / HPLC/ESI-MS/MS
comp. DAN41 / DAN
m/e / int. / m/e / int.
[M+1]+ / 344.34 / 9 / 358.29 / 3
[M+1-H2O]+ / 326.21 / 72 / 340.27 / 20
[M+1-CO2]+ / 320.20 / 100 / 314.24 / 100
[M+1-CHFO2]+ / 294.20* / 90
[M+1- CH3NO2]+ / 283.13 / 100
[M+1-C2H5NO2]+ / 283.26 / 10
[M+1-C3H5NO2]+ / 271.21* / 22
[M+1-C6H7NO2]+ / 219.19 / 12

*MS/MS/MS

1Appl.Cat.B.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF DAN (Soil)

Fragment / HPLC/ESI-MS/MS
DAN / comp. DAN1 / comp. DAN2 / comp. DAN3
m/e / int. / m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 358.16 / 2 / 360.24 / 2 / 362.12 / 40 / 390.20 / 48
[M+1-H2O]+ / 340.29 / 6 / 342.27 / 4 / 344.19 / 100 / 372.21 / 100
[M+1-HF]+
[M+1-H3FO]+ / 324.19* / 72
[M+1-CO2]+ / 314.26 / 100 / 316.28 / 100
[M+1-C3H2]+ / 352.19* / 20
[M+1-CH2O2]+ / 344.11* / 55
[M+1- CHFO2]+ / 294.16* / 100 / 326.12* / 100
[M+1- CH3NO2]+
[M+1-C2H5FO]+ / 298.12* / 68
[M+1-C2H5NO2]+ / 283.20 / 8
[M+1-C3H5FO2]+ / 298.13* / 35
[M+1-C4H5F]+ / 288.24* / 10
[M+1-C4H6FN]+ / 271.27* / 20
[M+1-C5H10FN]+ / 257.16* / 8
[M+1-C5H9NO]+ / 263.16* / 24
[M+1-C5H8FNO]+ / 245.14* / 64
[M+1-C5H9FN2O]+ / 230.06* / 100
[M+1-C6H8FN]+ / 245.10* / 18
[M+1-C6H10FN]+ / 245.23* / 100
[M+1-C7H12FN]+ / 231.17* / 6
[M+1-C8H1.3FN]+ / 204.03* / 4

*MS/MS/MS

1Appl.Cat.B.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF ENR (Aqueous soil suspension)

Fragment / HPLC/ESI-MS/MS
comp. N1 / comp. Q1 / ENR
m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 334.20 / 3 / 332.24 / 2 / 360.35 / 1
[M+1-H2O]+ / 316.22 / 15 / 314.24 / 4 / 342.38 / 2
[M+1-CO2]+ / 288.21 / 100 / 316.28 / 100
[M+1-HCO2]+ / 289.09 / 10
[M+1- CHFO2]+ / 268.23* / 100 / 296.25* / 10
[M+1-C3H4O]+ / 288.22* / 12
[M+1-C3H5NO]+ / 263.18 / 100
[M+1-C3H7NO2]+ / 245.18 / 20
[M+1-C3H5FO2]+ / 268.33* / 5
[M+1-C3H2FNO2]+ / 257.18* / 10
[M+1-C4H9NO]+ / 245.17* / 80
[M+1-C4H7NO2]+ / 231.15* / 30
[M+1-C4H5NO3]+ / 219.11 / 15
[M+1-C5H9NO2]+ / 245.20* / 100
[M+1-C6H9NO2]+ / 205.15* / 20
[M+1-C6H11NO2]+ / 231.12* / 9
[M+1-C7H11NO2]+ / 219.28* / 4
[M+1-C7H11N2O2]+ / 204.10* / 6

*MS/MS/MS

1Chemosphere 2012.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF LEV (Film)

Fragment / HPLC/ESI-MS/MS
comp. LEV11 / comp. LEV31 / LEV / comp. LEV4 / comp. LEV5
m/e / int. / m/e / int. / m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 336.14 / 1 / 348.22 / 1 / 362.21 / 1 / 293.12 / 12 / 307.15 / 10
[M+1-H2O]+ / 330.31 / 2 / 344.22 / 2 / 275.17 / 100 / 289.15 / 100
[M+1-CO2]+ / 304.25 / 100 / 318.26 / 100
[M+1- CH5N]+ / 305.11 / 7
[M+1-CH7N]+ / 260.22* / 62
[M+1-CHNO2]+ / 234.09* / 100
[M+1-CHO2F]+ / 284.21* / 90 / 298.22* / 8
[M+1-C2H3F]+ / 261.13* / 100
[M+1-C2HO2F]+ / 217.15* / 22 / 231.15* / 29
[M+1-C3H5NO2]+ / 261.20* / 100 / 206.13* / 15
[M+1-C3H7N]+ / 279.08 / 100
[M+1-C3H6FN]+ / 261.12* / 100
[M+1-C4H7NO2]+ / 261.19* / 100

*MS/MS/MS

1Appl.Cat.B.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF LEV (Soil)

Fragment / HPLC/ESI-MS/MS
comp. LEV11 / LEV / comp. LEV21
m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 336.15 / 4 / 362.18 / 7 / 360.17 / 5
[M+1-HF]+ / 316.21 / 5
[M+1-H2O]+ / 344.17 / 15 / 342.32 / 7
[M+1-CO2]+ / 318.21 / 100
[M+1-CHO2]+ / 316.20 / 100
[M+1-CH5N]+ / 305.09 / 10
[M+1-C2H4FN]+ / 301.22* / 4
[M+1-CHFO2]+ / 298.21* / 6
[M+1-C3H7N]+ / 279.10 / 100
[M+1-C3H4O2]+ / 288.29* / 15
[M+1-C3H7NO2]+ / 273.23* / 5
[M+1-C4H11N]+ / 263.16 / 25
[M+1-C3H9NO]+ / 261.09* / 100
[M+1-C3H5NO3]+ / 257.08* / 10
[M+1-C4H7NO2]+ / 261.17* / 100
[M+1-C4H5NO3]+ / 245.08* / 100
[M+1-C5H11NO]+ / 235.15 / 15
[M+1-C5H7NO3]+ / 231.15* / 10

*MS/MS/MS

1Appl.Cat.B.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF LEV (Aqueous soil suspension)

Fragment / HPLC/ESI-MS/MS
comp. LEV11 / LEV31 / comp. LEV
m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 336.15 / 1 / 348.35 / 1 / 362.18 / 7
[M+1-HF]+ / 316.30 / 5
[M+1-H2O]+ / 330.29 / 2 / 344.17 / 15
[M+1-CO2]+ / 304.21 / 100 / 318.21 / 100
[M+1-CH5N]+ / 305.24 / 7
[M+1-CHO2F]+ / 284.22* / 90
[M+1-C2H4FN]+ / 301.22* / 4
[M+1-CHFO2]+ / 298.21* / 6
[M+1-C3H7N]+ / 279.09 / 100
[M+1-C3H5NO2]+ / 261.18* / 100
[M+1-C3H7NO2]+ / 273.23* / 5
[M+1-C3H9NO]+ / 261.09 / 100*
[M+1-C4H7NO2]+ / 261.17* / 100
[M+1-C5H11NO]+ / 235.22 / 10

*MS/MS/MS

1Appl.Cat.B.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF MOX (Film)

Fragment / HPLC/ESI-MS/MS
comp.MOX7 / comp. MOX31 / comp. MOX81 / comp. MOX9 / MOX
m/e / int. / m/e / int. / m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 432.16 / 2 / 400.28 / 10 / 416.28 / 1 / 279.18 / 12 / 402.16 / 8
[M+1-H2O]+ / 414.19 / 100 / 382.24 / 100 / 398.24 / 4 / 261.12 / 100 / 384.27 / 18
[M+1-HF]+ / 380.14* / 4
[M+1-CO] / 388.16 / 100
[M+1-HFO]+ / 396.31* / 20
[M+1-CO2]+ / 358.20 / 100
[M+1-CH2O2]+ / 370.22* / 100 / 233.13* / 28
[M+1-CHNO2]+ / 220.07* / 100 / 343.26* / 26
[M+1-CHO2F]+ / 338.17 / 12
[M+1-C2H3N]+ / 238.14* / 14
[M+1-C2H4O]+ / 372.30 / 3
[M+1- C3H2]+ / 362.25 / 10
[M+1-C2H4O4]+ / 342.18* / 90
[M+1-C5H5N]+ / 321.17* / 8 / 323.14* / 22
[M+1-C5H4FN]+ / 305.07 / 2
[M+1-C5H5NO2]+ / 321.14 / 74
[M+1-C6H9NO]+ / 305.17 / 72
[M+1-C6H9NO2]+ / 305.26* / 15
[M+1-C6H5NO4]+ / 277.20 / 80
[M+1-C7H9NO4]+ / 261.14* / 32
[M+1-C8H11N]+ / 279.20* / 8
[M+1-C8H12FN]+ / 261.23 / 12
[M+1-C8H10FNO]+ / 261.20 / 20

*MS/MS/MS

1Appl.Cat.B.

Fragment / HPLC/ESI-MS/MS
comp. MOX61 / comp. MOX5
m/e / int. / m/e / int.
[M+1]+ / 321.12 / 18 / 293.15 / 50
[M+1-CH3]+ / 278.03* / 20
[M+1-H2O]+ / 303.14 / 100 / 275.13 / 100
[M+1-CH7N]+ / 260.04* / 55
[M+1-C2H4]+ / 293.19* / 10
[M+1-C2H3F]+ / 275.14* / 100
[M+1-C2H5NO]+ / 234.05* / 100
[M+1- C3H5FO]+ / 217.04* / 20
[M+1-C4H6FN]+ / 234.09* / 68

*MS/MS/MS

1Appl.Cat.B.

FRAGMENTATION OF PHOTOLYTIC PRODUCTS OF MOX (Soil)

Fragment / HPLC/ESI-MS/MS
comp. MOX1 / MOX / comp. MOX2 / comp. MOX31 / comp. MOX4
m/e / int. / m/e / int. / m/e / int. / m/e / int. / m/e / int.
[M+1]+ / 332.73 / 5 / 402.16 / 8 / 253.15 / 40 / 400.38 / 30 / 263.16 / 32
[M+1-CH3]+ / 238.10* / 58
[M+1-HF]+ / 380.14* / 20 / 245.09 / 100
[M+1-H2O]+ / 314.66 / 8 / 384.27 / 18 / 235.11 / 100 / 382.24 / 100
[M+1-NF]+ / 220.08* / 100
[M+1-CO2]+ / 358.20 / 100
[M+1-CHNO2]+ / 343.26* / 26
[M+1-CHO2F]+ / 338.17 / 12
[M+1-C2H4]+ / 304.68 / 14
[M+1-C2H3N]+ / 222.14* / 2
[M+1- C3H2]+ / 362.25 / 10
[M+1- CH3NO]+ / 355.23 / 5
[M+1-C2H3F]+ / 217.18* / 100
[M+1-C2H2FN]+ / 204.13* / 42
[M+1-C3H4]+ / 291.93 / 100
[M+1-C4H8]+ / 276.06 / 6
[M+1-C5H5N]+ / 323.14* / 22 / 321.29* / 10
[M+1-C5H4FN]+ / 305.07 / 2
[M+1-C8H11N]+ / 279.20* / 8
[M+1-C8H12FN]+ / 261.23 / 12
[M+1-C9H13N]+ / 265.16* / 8

*MS/MS/MS

1Appl.Cat.B.

Fragment / HPLC/ESI-MS/MS
comp. MOX5
m/e / int.
[M+1]+ / 293.15 / 50
[M+1-CH3]+ / 278.03* / 20
[M+1-H2O]+ / 275.13 / 100
[M+1-CH7N]+ / 260.04* / 55
[M+1-C2H5NO]+ / 234.05* / 100
[M+1-C3H5FO]+ / 217.04* / 20

*MS/MS/MS

1Appl.Cat.B.