Date ACCURATE-MASS DATABASE FOR SCREENING OF PESTICIDE RESIDUES IN FRUITS AND VEGETABLES BY GAS CHROMATOGRAPHY TIME-OF-FLIGHT MASS SPECTROMETRY
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1 Date ACCURATE-MASS DATABASE FOR SCREENING OF PESTICIDE RESIDUES IN FRUITS AND VEGETABLES BY GAS CHROMATOGRAPHY TIME-OF-FLIGHT MASS SPECTROMETRY
2 In practice, target analysis approach (analysing 1-4 of GC and LC amenable compounds) MEANS THAT THE MAJORITY OF THE LOW- FREQUENCY OR MISUSED COMPOUNDS ARE NOT LOOKED FOR
3 Target methods European Reference Laboratory - FV
4 Target methods Very Expensive
5 Target methods Very Expensive Time Consuming
6 Screening methods Practically all applications have been focused on LC (Time of flight) LC-TOF-MS (libraries containing fragments of compounds and retention time). Focused in GC (single quadrupole), commercial libraries.
7 GC-TOF/MS (full scan) (Ability to record an unlimited number of compounds) GC libraries (accurate masses of molecular ions and fragments and retention times)
8 Experimental conditions Injection volume: 2 μl Mode: Splitless MM Inlet Inyector temperature: 28ºC Agilent 72 Q-TOF GC/MS OVEN PROGRAM Rate(ºC/min) Value(ºC) Hold Time(min) Run Time(min)
9 Experimental conditions Injection volume: 2 μl Mode: Splitless MM Inlet Inyector temperature: 28ºC Agilent 72 Q-TOF GC/MS OVEN PROGRAM Rate(ºC/min) Value(ºC) Hold Time(min) Run Time(min) Post Run Time: 2 min Post Run temperature: 31ºC BACKFLUSHING CAPABILITIES Retention time locked with constant flow (Trifluralin)
10 Experimental conditions Injection volume: 2 μl Mode: Splitless MM Inlet Inyector temperature: 28ºC Agilent 72 Q-TOF GC/MS OVEN PROGRAM Rate(ºC/min) Value(ºC) Hold Time(min) Run Time(min) Post Run Time: 2 min Post Run temperature: 31ºC BACKFLUSHING CAPABILITIES Retention time locked with constant flow (Trifluralin) Electron Ionization Acquisition in full scan at 2 GHz Ion source temperature: 28ºC Transfer line temperature: 28ºC
11 BACKFLUSH CONFIGURATION 2 columns: HP5MSI (35ºC) 15mx25µmx.25µm Constant Flow Column 1 = 1.225ml/min Column 2= 1.425ml/min
12 Internal Reference Mass European Reference Laboratory - FV
13 Internal Reference Mass European Reference Laboratory - FV
14 GC-Q-TOF DATABASE Many ions in the mass spectra. The molecular ion is not always present in the spectra.
15 1ppb Tomate TIC European Reference Laboratory - FV
16 1ppb Tomate EIC ( _Vinclozolin Parent Ion) European Reference Laboratory - FV Molecular ion Vinclozolin
17 1ppb Tomate EIC ( _Vinclozolin Parent Ion) European Reference Laboratory - FV Molecular ion Vinclozolin 1ppb Tomate Mass Spectrum (tr = min)
18 1ppb Tomate EIC ( _Vinclozolin Parent Ion) European Reference Laboratory - FV Molecular ion Vinclozolin 1ppb Tomate Mass Spectrum (tr = min) NIST MASS INTERPRETER
19 1ppb Tomate EIC ( _Vinclozolin Parent Ion) European Reference Laboratory - FV Molecular ion Vinclozolin 1ppb Tomate Mass Spectrum (tr = min) NIST [C6H6NO2] + [C7H3Cl2NO] + [C1H9ClN ] + [C12H9Cl2NO3 ] + [C1H8Cl2N ] + MASS INTERPRETER
20 1ppb Tomate EIC ( _Chlorpyrifos Parent Ion) European Reference Laboratory - FV
21 1ppb Tomate EIC ( _Chlorpyrifos Fragment) Chlorpyrifos Fragment Chorpyrifos
22 1ppb Tomate EIC ( _Chlorpyrifos Fragment) Chlorpyrifos Fragment Chorpyrifos 1ppb Tomate Mass Spectrum (tr = 2.46 min)
23 1ppb Tomate EIC ( _Chlorpyrifos Fragment) Chlorpyrifos Fragment Chorpyrifos 1ppb Tomate Mass Spectrum (tr = 2.46 min) [C5H2Cl3NO] + [C9H11Cl2NO3PS ] + [C5H3Cl2NO3PS ] +
24 ACCURATE MASS DATABASE ### Formula Retention Time Mass Compound name # Formula RT Mass Cpd C17H16Br2O3 28,12 425,9466 Bromopropylate C13H9Br2O 28,12 338,92 Bromopropylate F1 C7H6BrO 28,12 184,962 Bromopropylate F2 C6H4Br 28,12 154,9496 Bromopropylate F3 C13H12BrCl2N3O 27,92 374,9541 Bromuconazole C1H8BrCl2O 27,92 292,9136 Bromuconazole F1 C13H12Cl2N3O 27,92 296,357 Bromuconazole F2 C1H9Cl2O 27,92 215,3 Bromuconazole F3 C7H3Cl2O 27,92 172,9561 Bromuconazole F4 C8H7Cl2 27,92 172,9925 Bromuconazole F5 C13H24N4O3S 24,1 316,1569 Bupirimate C11H18N3O3S 24,1 272,169 Bupirimate F1 C11H18N3O 24,1 28,145 Bupirimate F2 C5H4N2O 24,1 18,324 Bupirimate F3 C16H23N3OS 23,85 35,1562 Buprofezin C9H9N2S 23,85 177,486 Buprofezin F1 C7H5NO 23,85 119,371 Buprofezin F2 C7H8N 23,85 16,657 Buprofezin F3 C7H11N2OS 23,85 171,592 Buprofezin F4 C8H16N2S 23,85 172,134 Buprofezin F5 Continue...
25 ACCURATE MASS DATABASE ### Formula Retention Time Mass Compound name # Formula RT Mass Cpd C17H16Br2O3 28,12 425,9466 Bromopropylate C13H9Br2O 28,12 338,92 Bromopropylate F1 C7H6BrO 28,12 184,962 Bromopropylate F2 C6H4Br 28,12 154,9496 Bromopropylate F3 C13H12BrCl2N3O 27,92 374,9541 Bromuconazole C1H8BrCl2O 27,92 292,9136 Bromuconazole F1 C13H12Cl2N3O 87 PESTICIDES 27,92 296,357 Bromuconazole F2 C1H9Cl2O 27,92 215,3 Bromuconazole F3 C7H3Cl2O 2 FRAGMENTS 27,92 AT LEAST FOR EACH 172,9561 PESTICIDE Bromuconazole F4 C8H7Cl2 RETENTION TIMES 27,92 OF EACH PESTICIDE 172,9925 Bromuconazole F5 C13H24N4O3S 24,1 316,1569 Bupirimate C11H18N3O3S 24,1 272,169 Bupirimate F1 C11H18N3O 24,1 28,145 Bupirimate F2 C5H4N2O 24,1 18,324 Bupirimate F3 C16H23N3OS 23,85 35,1562 Buprofezin C9H9N2S 23,85 177,486 Buprofezin F1 C7H5NO 23,85 119,371 Buprofezin F2 C7H8N 23,85 16,657 Buprofezin F3 C7H11N2OS 23,85 171,592 Buprofezin F4 C8H16N2S 23,85 172,134 Buprofezin F5 Continue...
26 Data base in Excel file (csv format)
27 Data base in Excel file (csv format) Retention time tolerance:,5 min Mass error tolerance 1 ppm
28 % compounds % compounds 1µg/Kg_ 1µg/Kg_Spring onion 2µg/Kg_ 2µg/Kg_Spring onion 5µg/Kg_ 5µg/Kg_Spring onion 1µg/Kg_Spring onion 1µg/Kg_ % compounds % compounds 1µg/Kg_ 1µg/Kg_ European Reference Laboratory - FV 2µg/Kg_ 2µg/Kg_ 5µg/Kg_ 5µg/Kg_ 1µg/Kg_ 1µg/Kg_ TOMATO AUTOMATIC IDENTIFICATION POTATO SPRING ONION ORANGE % DETECTED % NOT DETECTED % ONE FRAGMENT DETECTED
29 % of pesticides detected European Reference Laboratory - FV AUTOMATIC IDENTIFICATION VS MANUAL IDENTIFICATION TOMATO ORANGE SPRING ONION POTATO µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Automatic identification Manual identification
30 NOT AUTOMATICALLY IDENTIFIED One ion is automatically detected Cpd Label Name Formula Score Mass Mass (DB) Diff (Tgt, ppm) Diff (Tgt, mda) 16 Cpd 16: Napropamide Napropamide C17 H21 N O2 81,36 271, ,1572-3,6 -,98 C17H21NO2 22,97 271,1572 Napropamide C12H11O 22,97 171,81 Napropamide F1 C7H14NO 22,97 128,175 Napropamide F3 12,2 ppm Napropamide in tomato at 5 µg/kg -81,31 ppm,84 ppm Napropamide (RT 23,4 min) coeluting with this peak
31 QUANTIFICATION European Reference Laboratory - FV
32 MATRIX EFFECT European Reference Laboratory - FV
33 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Chlozolinate Chlozolinate C(µg/Kg) C(µg/Kg) µg/Kg µg/Kg Endosulphan sulfate Endosulphan sulfate C(µg/Kg) C(µg/Kg)
34 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Metalaxyl Metalaxyl C(µg/Kg) C(µg/Kg) µg/Kg µg/Kg Vinclozolin Vinclozolin C(µg/Kg) C(µg/Kg)
35 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Ametryn Ametryn C µg/kg) C(µg/Kg) µg/Kg µg/Kg Cadusafos Cadusafos C (µg/kg) C(µg/Kg)
36 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Chlorpyrifos-Methyl Chlorpyrifos_Methyl C(µg/Kg) C(µg/Kg) µg/Kg µg/Kg Ethofumesate Ethofumesate C (µg/kg) C(µg/Kg)
37 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Malathion Malathion C (µg/kg) C(µg/Kg) µg/Kg µg/Kg Nuarimol 1 2 C (µg/kg) Nuarimol C(µg/Kg)
38 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Pirimiphos-Methyl C (µg/kg) Pirimiphos-Methyl C(µg/Kg) µg/Kg µg/Kg 15 Triadimefon 8 Triadimefon C (µg/kg) C(µg/Kg)
39 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Prothiophos Prothiofos C (µg/kg) C(µg/Kg) µg/Kg µg/Kg Terbumeton Terbumeton C (µg/kg) C(µg/Kg)
40 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Chlozolinate Chlozolinate C(µg/Kg) C(µg/Kg) µg/Kg µg/Kg Endosulphan sulfate Endosulphan sulfate C(µg/Kg) C(µg/Kg)
41 Area Area Area Area European Reference Laboratory - FV GC-QqQ/MS GC-QTOF/MS Metalaxyl Metalaxyl C(µg/Kg) C(µg/Kg) µg/Kg µg/Kg Vinclozolin Vinclozolin C(µg/Kg) C(µg/Kg)
42 RELATIVE ABUNDANCES AT DIFFERENT CONCENTRATIONS 1µg/Kg FLUTOLANIL 2µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances µg/Kg Relative Abundances to base peak % 31% 37% 41% % 19% 21% 3% 1µg/Kg
43 µg/Kg 2µg/Kg 5µg/Kg BOSCALID 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 19% 3% 32% % 46% 5% 51% µg/Kg
44 µg/Kg TERBUMETON µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 19% 114% 99% % 58% 71% 69% µg/Kg
45 RELATIVE ABUNDANCES IN DIFFERENT MATRICES European Reference Laboratory - FV µg/Kg PROPAZINE 2µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 86% 87% 89% % 25% 27% 24% 1µg/Kg
46 µg/Kg PROPAZINE 2µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 83% 88% 97% % 23% 22% 25% 1µg/Kg
47 1µg/Kg CHLORPYRIFOS METHYL µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 43% 46% 68% % 3% 27% 39% µg/Kg
48 µg/Kg CHLORPYRIFOS METHYL µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 58% 39% 47% % 31% 26% 31% µg/Kg
49 µg/Kg TRIFLURALIN µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 53% 61% 64% % 15% 17% 18% µg/Kg
50 µg/Kg TRIFLURALIN µg/Kg 5µg/Kg 1µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Absolute Abundances Relative Abundances to base peak % 58% 7% 74% % 17% 19% 24% 1µg/Kg
51 % Pesticides European Reference Laboratory - FV ACCURACY (%RSD, n =1) % RSD < 5 % RSD > 5 < 1 % RSD > TOMATO POTATO ORANGE SPRING ONION
52 % pesticides European Reference Laboratory - FV LIMITS OF DETECTION Retention time and at least two fragments with error lower than 5 ppm (correct relative abundance) TOMATO POTATO SPRING ONION ORANGE
53 % compounds European Reference Laboratory - FV LIMITS OF DETECTION Retention time and at least one fragment with error lower than 5 ppm (other fragments with error higher than 5 ppm but with the correct relative abundance) µg/Kg 2µg/Kg 5µg/Kg 1µg/Kg Spring onion
54 REAL SAMPLES Muestra GC-TOF automatico GCQQQMS GC-TOF manual Pepper Boscalid (.25mg/Kg) Boscalid(.23mg/Kg) Iprodione (.2mg/Kg) Iprodione(.27mg/Kg) _1 Pyriproxifen (.54mg/Kg) Pyriproxifen (.62mg/Kg) _2 Bifenthrin 1F(,12mg/Kg) Bifenthrin (.13mg/Kg) Ion error higher than1 ppm Melon_1 Bupirimate (.15mg/Kg) Bupirimate(.13mg/Kg) Buprofezin(.49mg/Kg) Buprofezin(.16mg/Kg) _3 Metalaxyl(.6mg/Kg) Metalaxyl(.68mg/Kg) Pirimicarb(.33mg/Kg) Pirimicarb(.24mg/Kg) Bupirimate(.11mg/Kg) Bupirimate(.48mg/Kg) Zucchini Penconazole(.91mg/Kg) Penconazole(.74mg/Kg) Brussels sprouts Boscalid(.21mg/Kg) Boscalid(.12mg/Kg) _4 Bifenthrin (.1mg/Kg) Bifenthrin (.125mg/Kg) Ion error higher than1 ppm Bean_1* Iprodione 1F(.83mg/Kg) Iprodione(1.2mg/Kg) Saturation* Azoxystrobin ND Azoxystrobin(.337mg/Kg) Coelution Bean_2 Iprodione(.36mg/Kg) Iprodione(.25mg/Kg) Azoxystrobin ND Azoxystrobin(.11mg/Kg) Coelution Bean_3 Iprodione(.19mg/Kg) Iprodione(.78mg/Kg) Azoxystrobin ND Azoxystrobin(.16mg/Kg) Coelution Melon_2 Bupirimate(.11mg/Kg) Bupirimate(.8mg/Kg) Bean_4* Iprodione ND(1.82mg/Kg) Iprodione(1.7mg/Kg) Saturation* Bean_5* Iprodione ND(1.27mg/Kg) Iprodione(1.7mg/Kg) Saturation* Iprodione(.15mg/Kg) Iprodione(.11mg/Kg) Grape Myclobutanil.41mg/Kg Myclobutanil(.41mg/Kg) *These samples were injecting diluted 1:2 to obtain a correct identification and quantification and the mass spetrum show at least 2 fragments ions.
55 Real Sample Bean C=,8 ppm IPRODIONE NOT DETECTED AUTOMATICALLY Rt= min Real Sample C=.276ppm ### Formula Retention Time Mass Compound name Description # Formula RT Mass Cpd Comments C13H13Cl2N3O3 27,81 329,334 Iprodione C12H1Cl2N3O3 27,81 314,99 Iprodione F1 C7H3Cl2NO 27,81 186,9592 Iprodione F3 DETECTED AUTOMATICALLY Rt= min
56 The system has 2 modes of operation : 2GHz Extended Dynamic Range (EDR) mode 4Ghz High Resolution (HR) mode
57 Benalaxyl 2GHz Fragment Benalaxyl F1 Molecular formula Experimental mass Theorethic al mass Error (ppm) C18 H2 N O 266, ,1539,83 4GHz Fragment Benalaxyl F1 Benalaxyl F2 Benalaxyl F4 Benalaxyl F5 Molecular formula Experimental mass Theorethical mass Error (ppm) C18 H2 N O 266, ,1539,83 C13 H16 N O3 234, ,1125-2,19 C12 H16 N 26, ,1176 -,81 O2 C11 H14 N O 176, ,17 1,67
58 Benalaxyl 2GHz 4GHz
59 -34.7 ppm -23,7 ppm Benalaxyl 2GHz 2,1 ppm 5 ppm 1,13ppm ppm 6,4 ppm 4GHz 1,8ppm
60 % Pesticides European Reference Laboratory - FV 2 ppb in Automatic identification Detected no detected 1 fragment detected 2GHz 4GHz
61 CONCLUSIONS European Reference Laboratory - FV
62 15 real samples were processed with the developed method, results were compared with those obtained by GC-QQQ-MS, from a total of 22 positives 14 were correctly identified automatically, and three pesticides were not identified correctly by GCQTOF because the high concentration saturate the detector, five pesticide were not correctly identified because the some of the ions showed errors higher than 1 ppm. This work is a first approach to the accurate mass database for automatic identification and quantification in GC-TOF-MS. It can be considered as a starting point for a large database and for an improved methodology for automatic identification. High Resolution (HR) mode can be considered as a alternative to improve the effectiveness of the automatic identification.
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