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2 Adding of new compounds to the routine methods from the working document SANCO/12745/2013 of 21 st 22 nd November 2017 rev. 9(1) 48 compounds by LC and GC, fully validated at and mg/kg in tomato, orange and avocado Ametoctradin (LC) Anthraquinone (GC) BAC10 (LC) BAC12 (LC) BAC8 (LC) Benalaxyl (GC) Chlorfluazuron (GC) Clomazone (LC) Cyazofamid (LC) Cyflufenamid (GC) Etoxazole (LC) Fenpyrazamine (LC) Flufenacet (LC) Fluopicolide (GC) Fluxapyrosad (LC) Heptachlor (GC) Heptachlor endo-epoxide (GC) Heptachlor exo-epoxide (GC) Ioxynil (LC) Isopyrazam (GC) Isoxaflutole (LC) Lufenuron (LC) Metconazole (LC) Metrafenone (LC) Molinate (GC) Novaluron (LC) Penflufen (LC) Penthiopyrad (LC) Phenthoate (GC) Picolinafen (GC) Propaquizafop (LC) Proquinazid (LC) Prothioconazole (LC) Prothioconazole-desthio (LC) Prothiofos (GC) Pyridalil (LC) Pyridate (LC) Pyriofenone (GC) Quinoclamine (LC) Quintozene (GC) Rotenone (LC) Spinetoram (LC) Spirotetramat (LC) Sulfoxaflor (LC) Tetramethrin (GC) Triallate(GC) Tricyclazole (LC) Triticonazole (LC) Tritosulfuron (LC)
3 Molecular Components Map of representative matrices of commodity groups (48 matrices)
4 Exact Mass database for LC-HRMS (with 188 compounds) Enlarge of the scope of the Accurate Mass Database by GC-HRMS (150 compounds)
5 Validation of the MRM methods at low concentration levels (0.002 mg/kg in GC-MS/MS and at mg/kg in LC-MS/MS) 203 compounds by GC-MS/MS 195 compounds by LC All of them, fully validated in tomato, orange, apple, avocado and tea
6 SELECTIVITY SENSITIVITY
7 Sensitivity
8 scco 2 AS MOBILE PHASE Liquid-like density Gas-like viscosity Low critical point T c = K P c = 73.8 bar High diffusivity Widely available, safe to use Capability to mix with a wide range of liquid solvents
9 SFC-MS/MS Systems CO 2 pump Column flow 1.5 ml/min Post-column flow µl/min MS analyzer ESI source Column BP R Co-solvent pump Auxiliary pump MeOH MeOH Ammonium formate (5 mm) Formic acid (0,1%)
10 BPR SUPERCRITICAL CO 2 (UNTIL CROSS THE BPR DEVICE) ESI MS SMALL AMOUNT OF ORGANIC SOLVENT REACHING THE SOURCE
11 IONIZATION EFFICIENCY Absence of water Lower surface tension Lower polarity Microdroplet in LC (containing water) CO 2 evaporation Lower flow in the MS detector Reduced microdroplet size Microdroplet in SFC (only MeOH) More analyte reaching the gas phase and the mass analyzer. Increase of sensitivity
12 INCREASE OF SENSITIVITY Lower injection volumes (matrix concentration 0.2 mg/ul) 5 Injection volume (µl) 4 Lower amount of sample with no loss of sensitivity 3 2 Reduced matrix effect 1 mg sample 1 0 LC SFC 0.4 mg sample
13 FRUITS AND VEGETABLES pplication of SFC-MS/MS for the detection of pesticides in fruits and vegetables 164 pesticides (log K OW -0.8 to Tomato Orange 6.9) High water content Acidic matrix Leek Interfering compounds
14 8,5 x108 8,9 x108 9,4 x108 9,7 x108 MAKE-UP FLOW TOTAL AREA OF COMPOUNDS PEEK DIAMETER 7,7 x10 8 I.D: 127µm I.D: 64 µm 150 µl/min 125 µl/min 100 µl/min 90 µl/min 80 µl/min
15 SENSITIVITY - IDENTIFIED COMPOUNDS 5 ppb 10 ppb 20 ppb 100% 95 90% 98% 98% 94% 85 80% 75 70% 65 60% 55 50%
16 logpow ELUTION ORDER Increased polarity 0-1 0% 20% 40% 60% 80% 100% LC RT(%) SFC End of chromatograp hic run
17 MATRIX EFFECT Evaluation Comparison between calibration curves built in matrix and solvent (considered as no suppression) % 1% 3% 35% Significant matrix effect (>50% suppression) % 87% 62% Low matrix effect (20-50% suppression) Irrelevant matrix effect (<20% suppression)
18 MATRIX EFFECT Carbaryl Matrix effect is more intense in samples with a high number of interfering compounds Tomato Orange Leek Profenofos Similar calibration curves for these three different matrices illustrate the low matrix effect.
19 ISOBARIC INTERFERENCES The use of high flow rates promotes the coelution of matrix compounds and analytes, which leads to modification of ion ratios (>30%). Ion Ratio 53,2 Ion Ratio 51,5 Tomato Isoprocarb Fenhexamid Orange Isoprocarb Lufenuron 331> > >189 Epoxiconazole Leek Imazalil Ion Ratio 240,1 Ion Ratio 54,1 Penthion-sulfone Fenarimol Fenoxycarb Phoxim Flutriafol Trichlorfon
20 METHOD VALIDATION Linearity Matrix-matched standards in the range of µg/l (5-500 µg/kg in samples) Reproducibility 5 replicates of each matrix extract Calibration curve (Profenofos leek) 8,0E+6 x10 6 R 2 = 0, % RSD of compounds (5ppb) 7,0E+6 7,00 6,0E+6 6,00 80% ,0E+6 5,00 60% 4,0E+6 4,00 3,0E+6 3,00 40% 2,0E+6 2,00 1,0E+6 1,00 0,0E % 0% <10 % % >20 %
21 SPICES Application of SFC-MS/MS for the detection of pesticides in spices Interferring matrix components 162 pesticides (log K OW -0.9 to 6.9) Cayenne Black pepper Strong matrix effect
22 Percentage of compounds (%) MATRIX EFFECT Low flow rate in the source Reduced microdroplet size Absence in water in the mobile phase Lower polarity and surface tension Smaller amount of sample injected Fewer interferences Cayenne Black pepper Weak Medium Strong
23 Signal Percentage of compounds METHOD VALIDATION Calibration curve (Isoprocarb in cayenne) Linearity Matrix-matched standards in the range of µg/l ( µg/kg in samples) R 2 = Reproducibility Concentration 0 RSD < 20% RSD < 10% Cayenne Black Pepper
24 Number of detections Carbendazim Imidacloprid Acetamiprid Azoxystrobin Metalaxyl Tebuconazole Chlorpyrifos Profenofos Chlorantraniliprole Fluopyram Myclobutanil Triazophos Ethion 2,4-D Deet Difenoconazole Kresoxim-methyl Linuron Propiconazole Methamidophos Flonicamid Fluazifop Hexaconazole Pyraclostrobin Thiacloprid Thiamethoxam Boscalid Mandipropamid Fenpyroximate Flusilazole Indoxacarb Trifloxystrobin Etofenprox Methomyl Pirimiphos-methyl Propargite Propizamide Bromuconazole Buprofezin Dicrotophos Ethoprophos Fenpropathrin Imazalil Pyridaben Pyriproxyfen Tebufenozide REAL SAMPLES Total number of samples: Below the MRL Above the MRL
25 Z-score Z-Score PROFICIENCY TESTS 2 1,5 1 0,5 0,2 0,2 0,3 2 1,5 1 0,5 1,2 0,9 1,2 1,6 0, ,5-0, ,5-1, JRC-GEEL (2017) Fipronil in eggs FAPAS (2017) Pesticide Residues in pear purée
26 CONCLUSIONS SFC provides a high sensitivity of the analysis even with small amounts of sample injected: - Absence of water. - Evaporation of CO 2 in the mobile phase. The use of SFC-MS/MS allowed the identification of the majority of 164 pesticides in tomato (98%), orange (98%) and leek (94%) at 5 µg/kg. Good recoveries (70-120%) were obtained in cayenne (89%) and black pepper (93%) at 50 µg/kg. Some polar and acidic compounds underwent an increase of their signals. Their peak shapes could also be improved. Very low matrix effect was observed for most compounds in all matrices studied.
27 GC/MS LC/MS
28 T C Oven temperature program with different runtime methods Ramp 1 30ºC/min 9,4 Ramp 2 20ºC/min 12,4 Ramp 3 19,3 10ºC/min Time (min)
29 2,4'-DDE 2-Phenylphenol 4,4'-DDD 4,4'-DDE 4,4'-DDT Acrinathrin Alachlor Aldrin Ametryn Atrazine Azoxystrobin Benalaxyl Bifenox Bifenthrin Biphenyl Bixafen Boscalid Bromopropylate Bupirimate Buprofezin Butralin Butylate Cadusafos Carbofuran Carbophenothio n Chinomethionat e Chlorbromuron Chlordane Chlorfenapyr Chlorobenzilate Chlorothalonil Chlorpropham Chlorpyrifos Chlorpyrifos-methyl Chlorthal-dimethyl Chlozolinate Coumaphos Cyfluthrin Cypermethrin Cyproconazole Cyprodinil Deltamethrin Desmethyl-pirimicarb Diazinon Dichlofluanid Dichloran Dichlorobenzopheno ne Dichlorvos Diclobutrazol Dicofol Dieldrin Diethofencarb Dimethenamid Dimethipin Diphenylamine Disulfoton Disulfoton-sulfoxide Dodemorph Endosulfan sulfate Endosulfan-alpha Endosulfan-beta Endrin EPN Epoxiconazole Ethion Ethofenprox Ethofumesate Ethoprophos Ethoxyquin Etrimfos Fenamidone Fenarimol Fenazaquin Fenbuconazole Fenchlorphos Fenhexamid Fenitrothion Fenpropathrin Fenpropidin Fenpropimorph Fenthion Fenvalerate Fipronil Fipronil sulfone Fipronil-desulfinil Flampropisopropyl Flamprop-methyl Fluacrypyrim Fluazifop-p-butyl Flucythrinate Fludioxonil Fluopicolide Fluopyram Fluquinconazole Flusilazole Flutolanil Flutriafol Fluvalinate-tau Fonofos Formothion Fosthiazate HCB HCH-alpha HCH-beta Heptachlor Heptachlor endoepoxide Heptachlor exo-epoxide Heptenophos Hexaconazole Indoxacarb Iprodione Iprovalicarb Isazofos Isocarbophos Isofenphos Isofenphos-methyl Isoprothiolane Isopyrazam Kresoxim-methyl -Cyhalothrin Lindane Malaoxon Malathion Mecarbam Mepanipyrim Merphos Metalaxyl Metazachlor Metconazole Methidathion Methiocarb Methoxychlor Metolachlor Mevinphos Molinate Myclobutanil Napropamide Nuarimol Ofurace Oxadixyl Paclobutrazol Paraoxon-methyl Parathion Parathion-methyl Penconazole Pendimethalin Pentachloroanili ne Permethrin Phenothrin Phenthoate Phorate Phorate sulfone Phosmet Phthalimide Picolinafen Picoxystrobin Pirimicarb Pirimiphosmethyl Procymidone Profenofos Prometon Prometryn Propaphos Propazine Propiconazole Propyzamide Prosulfocarb Prothiofos Pyraclostrobin Pyrazophos Pyridaben Pyrifenox Pyrimethanil Pyriproxyfen Quinalphos Quinoxyfen Quintozene Secbumeton Spirodiclofen Spiromesifen Sulfotep Sulprofos Tebuconazole Tebufenpyrad Tecnazene Tefluthrin Terbufos Terbumeton Terbutryn Tetrachlorvinphos Tetraconazole Tetradifon THPI Tetramethrin Thiobencarb Tolclofos-methyl Tolylfluanid Triadimefon Triazophos Trifloxystrobin Trifluralin Vinclozolin 203 GC compounds
30 Azoxystrobin (data points per peak with the 5 runtime methods) 16 data points per peak 9.4 min 12.4 min min min min 42
31
32 9.4 min Overlapping peaks Chlorobenzilate 139> min Cyproconaz ole 100> min 12.4 min Interference +changement in peaks order Interference Thiobencarb
33 Extraction Method Citrate buffered QuEChERS 10 g of Sample + 10 ml of AcN Shake 4 min 4 g MgSO g NaCl + 1 g NaCit 2H 2 O +0.5 g NaCit 1.5H 2 O Shake 4 min Centrifuge 5 minutes at 3700 rpm Take 5 ml mg MgSO mg PSA Centrifuge 5 minutes at 3700 rpm Acidify with 10 ul formic acid 5 % per ml of extract Solvent exchange (EtAc) Analysis 1 g Sample/mL
34 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% LOQ Tomato Apple Orange 0% 2 µg.kg-1 10 µg.kg-1 50 µg.kg-1
35 90% 80% 75% 86% Matrix effect % 70% 60% 50% 40% 30% 25% Apple/Tomato Orange/Tomato 20% 10% 0% 13% 0% 0% Weak Moderate Strong -20 to 20 % -20 to -50 % and 20 to 50 % <-50 and >50 %
36 12% 88 % Samples with no pesticide residues Samples with detections > 2 µg.kg-1 Samples with detections > 10 µg.kg-1
37
38 Extraction Method Modified Citrate buffered QuEChERS 2 g of Sample + 7 ml H 2 0 (30 min soaking time) Shake 7 min Add 10 ml ACN 5 times dilution Add 4 g MgSO g NaCl + 1 g NaCit 2H 2 O +0.5 g NaCit 1.5H 2 O Shake 7 min Centrifuge 5 minutes at 3700 rpm Activate EMR-Lipid by adding 5 ml of water Transfer 5 ml of the supernatant into EMR-Lipid tubes Mix and centrifuge for 5 minutes at 3700 rpm Transfer 5 ml of the supernatant into Polish tubes (0.4 g NaCl+ 1.6 g MgSO 4 ) Mix and centrifuge for 5 minutes at 3700 rpm Solvent Exchange (EtAc) 5 times dilution Analysis of 0,04 g Sample/mL
39 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% LOQ M /LOQ I Black Pepper Cayenne Pepper 50 µg.kg µg.kg-1 >200 µg.kg-1 2 µg.kg-1 8 µg.kg-1 >8 µg.kg-1
40 Matrix effect 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 97% 89% 55% 12% 5% 4% Weak Moderate Strong Black pepper/tomato Cayenne/tomato
41 Total of 50 samples Percentage of samples 30% 27% 25% 23% 20% 18% 15% 14% 10% 5% 5% 5 0% No detected pesticides 1 detected pesticide 2 detected pesticides 3 detected pesticides 4 detected pesticides > 5 detected pesticides
42
43 Injection volume Matrix injected in column LC: 5 µl 5 mg 2.5 mg 1 mg 0.5 mg 0.25 mg GC: 1 µl 1 mg 0.5 mg 0.2 mg 0.1 mg 0.05 mg Green Tea Dilx0 1 g/ml Dilx2 0.5 g/ml Dilx5 0.2 g/ml Dilx g/ml Dilx g/ml
44 % Pesticides Suppression >50% EFFECT OF DILUTION IN EASY-MEDIUM COMPLEX MATRICES 60 LC-TOF-MS Leek Orange Broccoli Tomato Pepper Grape Cucumber 0 No 5 mg Dilution Dil 1 mg x 5 Dil 0.5 x 10 mg Dil 0.25 x 20 mg
45 RESOLUTION
46 Resolution at FWHM - full-width half maximum (Full Width of the peak at Half its Maximum height) R = m m 50% of hight Δm m For example: = = =
47 Relative Abundance Effects of increased resolution m/z
48 Effects of increased resolution Resolution: Resolution:
49 RESOLUTION (30,-50,000) + MASS ACCURACY (5ppm) Nominal Mass----Exact Mass
50 INSTRUMENTATION: Time of flight Orbitrap Fourier transform ion cyclotron (electric/magnetic) sector instrument
51 GC-EI-HRMS Full Scan or Full Scan? That is the NO question
52 Thiobencarb 0.01 mg/kgin Tomato Interference + shifts in peaks order Thiobencarb 9.3 min Interference GC-Intuvo MS/MS (100>72) GC-Orbitrap MS m/z m/z
53 Diethofencarb mg/kg in Tomato SRM1: 151>122 SRM2: 207>151 m/z m/z GC-Intuvo-MS/MS GC-Orbitrap MS
54 Fluquinconazole mg/kg in Tomato m/z m/z GC-QToF-MS GC-Orbitrap-MS
55 GC-EI-QExative 60k Orbitrap GC-EI-MS System Full scan MS Real Samples: Fluopyram 50 µg/kg Std in Tomato Real Sample: Pear C = 26 µg/kg Ratio Ion 2/1: 52% Ratio Ion 3/1: 29% Ratio Ion 4/1: 34% Ratio Ion 2/1: 50% Ratio Ion 3/1: 30% Ratio Ion 4/1: 35% The ion ratios are within ± 4% with respect to the standard and mass accuracy below 0.2 mda Ion 1 ( ): 0.01 mda Ion 2 ( ): 0.14 mda Ion 3 ( ): mda Ion 4 ( ): 0.02 mda
56 SENSITIVITY (10 ug/kg) LINEARITY (2 orders) + REPRODUCIILITY (< 20%)
57 LC-HR-ESI-MS/MS All Ion Fragmentation or NOT AIF? That is the question targeted MS SIM MS2 Narrow quadrupole window with or without triggering non-targeted Full Scan Wide quadrupole window(s)
58 Carbendazim in Carrot MRM-LC-HR-MS/MS, Isolation Mass Window: 0.7 Da 0.01 mg/kg 0.1 mg/kg Mass accuracy precursor: -1.0 ppm Mass accuracy fragment: -4.9 ppm Ion ratio: 0.14 Mass accuracy precursor: -0.1 ppm Mass accuracy fragment: -4.4 ppm Ion ratio: 0.17 Precursor Ion: Fragment Ion: Ratio Difference: -18%
59 SENSITIVITY (10 ug/kg) LINEARITY (2 orders) + REPRODUCIILITY (< 20%)
60 INSTRUMENTAL ISSUES ASSOCIATED WITH LC-HRMS WORKING IN ALL ION FRAGMENTATION
61 0.010 mg/kg Flufenoxuron AIF 1 window Aubergine Broccoli Lemon [M+H] + [M+H] + [M+H] + F1 F1 F mg/kg [M+H] + [M+H] + [M+H] + F1 F1 F1 Ratio difference within ± 65 %
62 Mass Peticides - tomato matrix compounds 2408 Matrix compounds 1Da 1 min
63 Pesticides - orange matrix compounds Mass 8017 Matrix compounds 1Da 1 min
64 Pesticides - orange matrix compounds Mass 8017 Matrix compounds 1 min
65 Pesticides - orange matrix compounds Mass 8017 Matrix compounds 80Da 1 min
66 0.010 mg/kg Flufenoxuron AIF 10 windows Aubergine Broccoli Lemon F1 [M+H] + F1 [M+H] + F1 [M+H] mg/kg F1 [M+H] + F1 [M+H] + F1 [M+H] + Ratio difference within ± 18 %
67 BUT.
68 Cycle Time LC-QTOF-MS X500R (AIF -20 Windows) 32k 32 k 32 k 32 k 32 k 32 k 32 k 32 k 32 k 32 k 32 k 32 k 32 k 32 k LC-QTOF-MS X500R (AIF -10 Windows) 0.05 s x 20 Windows = 1 s 0.2 s 1.2 s 32k 32 k 32 k 32 k 32 k 32 k 32 k 0.05 s x 10 Windows = 0.5 s LC-QOrbitrap-MS (AIF) 70k 0.2 s 0.7 s 70k LC-TQ-MS 0.27 s 0.6 s 0.38 s MS1 MS2
69 Retrospective Analysis combined? with the use of databases and libraries. Old or very rare detected compounds OR Very expensive analytical standards Compounds produced during the analysis
70 SELECTIVITY SENSITIVITY
71 > 132.1, > x10 2 Ratio = Counts Azinphos- methyl at mg kg -1 Injected amount:0.2 mg sample 7 6 LC-QqQ-MS/MS Green Tea RT: LC-Q-Exactive-Orbitrap-MS/MS EIC ± 5ppm NL: 1.24E4 Base Peak m/z= F: FTMS + p ESI Full ms [ ] MS Te_verde_10pbb_dil25_5mi cro Relative Abundance Acquisition Time (min) Time (min)
72 CONCLUSIONS GC and LC-HRMS provide very accurate results improving the identification confidence ( 10 ug/kg). In cases of limitation in achieving analytical standards prediction of presence/ no presence can be provided. In special GC-EI-HRMS can be easily implemented in the laboratories very effectively. However, an increase of the sensitivity around 5-10 times should be necessary to be applied with the same workflows than triple quadrupoles
73
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