European Reference Laboratory - FV. 53 rd Annual North American Chemical Residue Workshop. 18 th July 2016
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1 18 th July 2016
2 Pyrimethanil at 0.01 mg/kg ± 1 Da ± Da Pyrimethanil [M+H + ] m/z mg/ kg in onion RT = 7.05 min Dilution 5x
3 MILLING SAMPLE EXTRACTION LC MS/MS REPORT GC MS/MS EVALUATION
4 LC-QqQ, n=185 (Ratio SRM2/SRM1) CE (V) 1. Acephate (10 %) Carbendazim (4 %) Clomazone (2 %) Cyazofamid (3 %) Dichlorvos (14 %) Diniconazole (12 %) Fipronil (12 %) Fludioxonil (12 %) 5 9. Hexaconazole (10 %) Isofenphos methyl (11 %) Isoxaflutole (8 %) Mepanipyrim (10 %) Metconazole (7 %) Paclobutrazol (6 %) Pencycuron (9 %) Spinosyn A (2 %) Spinosyn D (1 %) Tebuconazole (5 %) Thiacloprid (6 %) Thiobencarb (7 %) Triadimenol (4 %) Triazophos (8 %) Triticonazle (5 %) 41 Low second transition at 0.01 mg/kg in tomato GC-QqQ, n=210 (Ratio SRM2/SRM1) CE (V) 1. 2,4 -DDE (12 %) ,4 -DDE (12 %) Bifenthrin (5 %) Bromopropylate (8 %) Cadusafos (11 %) Chlozolinate (11 %) 5 7. Cypermethrin (11 %) Ethoxyquin (14 %) Fenpropidin (10 %) Heptachlor (10 %) Heptenophos (3 %) Isocarbophos (7 %) Isofenphos-methyl (9 %) Paclobutrazole (13 %) Secbumeton (10 %) Tetrachlorvinphos (14 %) 35 In red, low collision energies In green, high collision energies
5 Transitions at 0.05 mg/kg in tomato LC-QQQ-MS/MS Clomazone Carbendazim > 124.9, > Counts x10 4 Ratio = 1.8 (91.5 %) Ratio: 2% Acquisition Time (m > 160.0, > Counts x10 4 Ratio = 4.4 (94.9 %) Ratio: 4% Acquisition Time (m
6 Mass Data base components- orange matrix compounds (1 g/ml) m/z: Rt: 4-8 min m/z: Rt: 7-13 min 8017 Matrix compounds Miner 3D Enterprise DB: 750 components Orange: 2743 matrix compounds
7 Azinphos methyl at 10 µg/kg in Onion. LC-QqQ-MS/MS Std in solvent at 10 µg/l Ethyl Acetate method NL method Citrate QuEChERS without clean-up method Citrate QuEChERS method x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 CID@8.0 (318.0 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 CID@8.0 (318.0 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 CID@8.0 (318.0 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 CID@8.0 (318.0 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 CID@8.0 ( Ratio: 0.37 * * * * * Ratio: 0.08 Diff.: 78% (>30 %) Ratio: 0.09 Diff.: 76% (>30 %) Ratio: 0.06 Diff.: 84% (>30 %) Ratio: 0.46 Diff.: 24% x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 ( > 26 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 ( > 26 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 ( > 26 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 ( > 26 x10 2 +ESI MRM Frag=380.0V CF=0.000 DF=0.000 ( > * * * * * Counts vs. Acquisition Time (min) Counts vs. Acquisition Time (min) Counts vs. Acquisition Time (min) Counts vs. Acquisition Time (min) Counts vs. Acquisition Time (min)
8 EUPT Sample: coriander FALSE NEGATIVE Linuron Standard in solvent Ion ratio: 1.8 Linuron (0.125 mg/kg) Real sample of coriander Ion ratio: 2.4
9 EUPT Sample of coriander LC-HRAMS Linuron Matrix interference
10 LC-Orbitrap Carbendazim, 0.01 mg/kg in Tomato RT: Relative Abundance SM: 3G Full scan MS ± 5ppm Mass error -0.5 ppm (-0.1 mda) AIF MS ± 5ppm Mass error -1.9 ppm (-0.3 mda) Time (min)
11 MASS ACCURACY RESOLUTION
12 80 C 0-25 H 0-50 N 0-5 O 0-5 Cl 0-5 Br 0-5 S0-5 Number of possible molecular formulas Resolution Resolution ~ FWHM 25 molecular formulas - Cl, Br 12 molecular formulas Resolution ~ FWHM 9 molecular formulas 5 ppm - Cl, Br 5 molecular formulas Absolute mass error relative to Thiabendazole Thiabendazole C 10 H 7 N 3 S (m/z ) (Da) (ppm) ~ ~ ~ ~ ~ (FWHM) ~ ~
13 Influence of resolution on detection Exact mass of bupirimate: Relative Abundance Resolution Two non resolved matrix ions. Mass error 4.7 ppm False detect of bupirimate Resolution Matrix ion. Mass error ppm Matrix ion. Mass error 27.1 ppm m/z
14 Identification criteria (EU) Quantitation LOQ, Linearity, Reproducibility,
15 Combining Full Scan MS and MS 2 Mode
16 17,5 K Orbitrap Full scan MS FS/dd-MS 2 70k 17.5 k MS 2 Target MS 2 analysis. Fragmentation is carried out only if precursor ion is detected in full scan MS. List of precursor ions is necessary. FS/AIF-MS 2 70k 70k Non-target MS 2 analysis. Fragmentation is carried out during entire chromatographic run. No precursor selection. No list of precursor ions is present s 0.6 s
17 Analysis of real samples by LC-HRAMS MS 2 Metalaxyl (XIC m/z ± 5 ppm). Full scan MS. Resolution Pepper spiked at 0.01 mg/kg metlaxyl Grapefruit Real sample 1 Grapefruit Real sample 2
18 LC-QOrbitrap (QExactive) Metalaxyl (XIC m/z ± 5 ppm). Full scan MS. Resolution XIC m/z ± 5 ppm Standard of Metlaxyl Library MS/MS spectrum 192,1382 Expected fragments: XIC m/z ± 5 ppm Grapefruit Real sample MS spectrum Experimental MS/MS spectrum FALSE POSITIVE 191,0603
19 Tomato Pesticides Full scan QTOF Orbitrap MS 2 QTOF Orbitrap Azoxystrobin Diazinon Dichlorvos Fenamiphos - sulfone 0.01 mg/kg Profenofos Orange Pesticides Full scan QTOF Orbitrap MS 2 QTOF Orbitrap Azoxystrobin Diazinon Dichlorvos Fenamiphos - sulfone 0.01 mg/kg Profenofos
20 MILLING SAMPLE EXTRACTION LC MS/MS HRAMS REPORT GC MS/MS EVALUATION
21 SENSITIVITY LINEARITY + REPRODUCIILITY
22 11 Matrices Lettuce Cucumber Orange Green bean Onion Apple Parsley Leek Tomato Garlic Spinach
23 LC-Orbitrap QExactive Focus LOQ % of compounds 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg Tomato 0.05 mg/kg ddms2 Target MS 2 AIF Non Target MS 2 (AIF) % of compounds 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg Apple 0.05 mg/kg ddms2 Target MS 2 AIF Non Target MS 2 (AIF) % of compounds 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg Orange 0.05 mg/kg ddms2 Target MS 2 AIF Non Target MS 2 (AIF) % of compounds 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg Onion 0.05 mg/kg ddms2 Target MS 2 AIF Non Target MS 2 (DIA)
24 LC-Orbitrap QExactive Focus Identification 166 pesticides x 11 matrices = 1826 results 100% 90% % of compounds 80% 70% 60% 50% 40% 30% 20% 0.01 mg/kg 0.1 mg/kg 10% 0% ddms2 AIF
25 Linearity LC-HRAMS 2.0E+09 Area 1.8E E+09 Spinach 1.4E E E E E E E+08 Pirimiphos-methyl Azoxystrobin Ethoprophos Imidacloprid Flusilazole Zoxamide 0.0E Concentration [mg/kg]
26 EU Proficiency Test 50% +25% -25% -50% Homogeneity: 0,085 mg/kg HRAMs No HRAMs
27 Real Samples Results by LC Concentration (mg/kg) Matrix Compound LC-QqQ-MS/MS LC-Orbitrap-MS/MS Diff (%) Maniquises Apricot Tebuconazole < LOQ < LOQ - Green Celery Boscalid < LOQ < LOQ - Dfenoconazole < LOQ < LOQ - Linuron < LOQ < LOQ - Pirethrin I < LOQ < LOQ - Broccoli - < LOQ < LOQ - Zucchini Imidacloprid < LOQ < LOQ - Myclobutanil < LOQ < LOQ - Thiamethoxam < LOQ < LOQ - Pumpkin Cyromazine < LOQ < LOQ - Kiwi - < LOQ < LOQ - Peach Chlorpyrifos < LOQ < LOQ - Conferencia Pear_E Boscalid Difenoconazole Diflubenzuron Imazalil Imidacloprid Paclobutrazole < LOQ < LOQ - Pyraclostrobin Tebuconazole Thiacloprid Trifloxystrobin Conferencia Pear_M Boscalid Difenoconazole Fluopyram Imazalil Imidacloprid Kresoxim Methyl < LOQ < LOQ - Pyraclostrobin Tebuconazole Red Pepper Fluopyram < LOQ < LOQ - Flutriafol Red Chili Pepper Flutriafol Pirimicarb Green Pepper Flutriafol < LOQ < LOQ - Metalaxyl Banana Imazalil Carrot_E - < LOQ < LOQ - Carrot_M - < LOQ < LOQ -
28 Robustness of peak area LC-Orbitrap Area Area Carbendazim d % - 20% Day Malathion-d % - 20% Day
29 Robustness of mass accuracy LC-Orbitrap 1.0 Carbendazim d Error [pmda] Day Malathion-d Error [ppm] Day
30 Scope: 464 pesticides 516 matrices samples 141 pesticides reported Data provided by
31 Full scan MS Target MS 2 Full scan MS Non-target MS 2 Full scan MS Target MS 2 Non-target MS 2
32 Orbitrap Full scan MS 17,5 K MS 2 FS/dd-MS 2 70k 17,5 k Target MS 2 analysis. Fragmentation is carried out only if precursor ion is detected in full scan MS. List of precursor ions is necessary. FS/AIF-MS 2 70k 70k Non-target MS 2 analysis. Fragmentation is carried out during entire chromatographic run. No precursor selection. No list of precursor ions is present. FS/dd-MS 2 /AIF-MS 2 70k 70k 17,5 k Combined target and non-target MS 2 analysis. Fragmentation without precursor selection is carried out during entire chromatographic run. List of target precursor ions is present. Fragmentation with precursor selection is carried out only if a precursor ion from the list is detected in full scan MS s 0.6 s 0.7 s
33 ddms 2 Target (166 compounds) Acephate Emamectin B1a Isoxaflutole Propyzamide Acetamiprid Epoxiconazole Kresoxim-methyl Proquinazid Aldicarb Ethion Linuron Prothioconazole Aldicarb-sulfone Ethirimol Lufenuron Pymetrozine Aldicarb-sulfoxide Ethoprophos Malaoxon Pyraclostrobin Azinphos-methyl Etofenprox Malathion Pyrethrini Azoxystrobin Famoxadone Mandipropamid Pyrethrinii Bifenazate Fenamidone Mepanipyrim Pyridaben Bitertanol Fenamiphos Metalaxyl Pyridate Boscalid Fenamiphos-sulfone Metconazole Pyrimethanil Bromuconazole Fenamiphos-sulfoxide Methidathion Pyriproxyfen Bupirimate Fenarimol Methiocarb Quinoclamine Buprofezin Fenazaquin Methiocarb-sulfone Quinoxyfen Carbaryl Fenbuconazole Methiocarb-sulfoxide Rotenone Carbendazim Fenhexamid Methomyl Spinosyn A Carbofuran Fenoxycarb Methoxyfenozide Spinosyn D Chlorantraniliprole Fenpropathrin Metobromuron Spirodiclofen Chlorfenvinphos, B- Fenpropimorph Monocrotophos Spiromesifen Chlorpyrifos Fenpyrazamine Myclobutanil Spirotetramat Chlorpyrifos-methyl Fenpyroximate Nitenpyram Spiroxamine Clofentezine Fenthion Omethoate Tebuconazole Clomazone Fenthion-sulfone Oxadixyl Tebufenozide Clothianidin Fenthion-sulfoxide Oxamyl Tebufenpyrad Coumaphos Flonicamid Paclobutrazol Terbuthylazine Cyazofamid Flufenacet Paraoxon methyl Tetraconazole Cymoxanil Flufenoxuron Penconazole Thiabendazole Cyproconazole Fluopyram Pencycuron Thiacloprid Cyprodinil Fluquinconazole Pendimethalin Thiamethoxam Cyromazine Flusilazole Phenthoate Thiobencarb Demeton-S-Methyl-Sulfone Flutriafol Phosalone Thiodicarb Demeton-S-methylsulfoxide Formetanate Phosmet Thiophanate-methyl Diazinon Fosthiazate Phoxim Tolclofos-methyl Dichlorvos Haloxyfop Pirimicarb Triadimefon Dicrotophos Hexaconazole Pirimicarb, desmethyl- Triadimenol Diethofencarb Hexythiazox Pirimiphos-methyl Triazophos Difenoconazole Imazalil Prochloraz Trichlorfon Diflubenzuron Imidacloprid Profenofos Trifloxystrobin Dimethoate Indoxacarb Propamocarb Triflumuron Dimethomorph Iprovalicarb Propaquizafop Triticonazole Diniconazole Isocarbophos Propargite Zoxamide Diuron Isofenfos methyl Propiconazole Dodine Isoprocarb Propoxur LC Orbitrap Compound list AIF-MS2 Non-target (102 compounds) Acetochlor Fenoxaprop-ethyl Napropamide Alachlor Fenpropidin Nuarimol Ametryn Fenuron Ofurace Anilofos Flamprop-methyl Oxycarboxin Atrazine Flazasulfuron Paraoxon ethyl Atrazine-Desethyl Fluacrypyrim Paraoxon methyl Azamethiphos Fluazifop-Butyl Phosphamidon Azinphos-ethyl Fluometuron Phosphamidon Bensulfuron-methyl Fluridone Picolinafen Bromacil Fonofos Picoxystrobin Buturon Forchlorfenuron Promecarb Cambendazole Fuberidazole Prometryn Carbetamide Furathiocarb Propachlor Chlorbromuron Heptenophos Propaphos Chloridazon Imazapyr Propaquizafop Chloroxuron Imazaquin Propazine Chromafenozide Isazofos Prosulfocarb Cinosulfuron Isofenphos Pyrazophos Clethodim Isofenphos-oxon Pyridaphenthion Cyanazine Isoproturon Pyrifenox Diafenthiuron Lenacil Pyrimidifen Dialifos Mebendazole Quinalphos Diclobutrazol Mecarbam Sulfosulfuron Difenoxuron Metamitron Sulprofos Diflufenican Metazachlor Terbumeton Dimefuron Metolachlor Terbuthylazine-desethyl Dimethylvinphos, Z- Metosulam Tetrachlorvinphos Dodemorph Metoxuron Thifensulfuron-methyl Edifenphos Metribuzin Thiophanate Ethiofencarb Metsulfuron-methyl Tolfenpyrad Ethiprole Mevinphos Triasulfuron Etrimfos Monolinuron Tribenuron-methyl Fenbendazole Monuron Tricyclazole Fenfuram Naled Vamidothion
34 FS/dd-MS 2 /AIF-MS 2 Pyridaben (target compound) 0.1 mg/kg in orange MS MS 2 Fragment ions detected in Data dependent MS2 MS MS 2 Fragment ion detected in AIF-MS 2
35 FS/dd-MS2/AIF-MS2 Isofenphos methyl (target compound) 0.1 mg/kg in orange MS MS 2 MS MS 2 Data dependent MS 2 failure MS 2 scan not triggered Fragment ion detected in AIF-MS 2
36 DETECTION OF NON-TARGET PESTICIDES 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% Tomato 0.01 mg/kg 0.02 mg/kg 0.05 mg/kg 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% Number of spiked pesticides102 Full scan Full scan + 1 MS2 fragment Full scan + 2 MS2 fragments Zucchini 100% 0.01 mg/kg 0.02 mg/kg 0.05 mg/kg 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg 0.05 mg/kg Full scan Full scan + 1 MS2 fragment Full scan + 2 MS2 fragments Lettuce Full scan Full scan + 1 MS2 fragment Full scan + 2 MS2 fragments
37 DETECTION OF NON-TARGET PESTICIDES Number of spiked pesticides102 Orange Leek 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg 0.05 mg/kg Full scan Full scan + 1 MS2 fragment Full scan + 2 MS2 fragments 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 0.01 mg/kg 0.02 mg/kg 0.05 mg/kg Full scan Full scan + 1 MS2 fragment Full scan + 2 MS2 fragments
38 DETECTION OF NON-TARGET PESTICIDES Imazapyr in pear (not included in EU Monitoring Program) (mass of protonated molecule ) RT: Full scan MS ± 5ppm Relative Abundance AIF MS 2 AIF MS ± 5ppm ± 5ppm AIF MS ± 5ppm Time (min)
39 MILLING LC-HRAMS SAMPLE EXTRACTION REPORT GC-HRAMS EVALUATION
40 IDENTIFICATION QUANTITATION Target Analysis Retention time Analytical standard 2 ions (<5 ppm) Recoveries Linearity Reproducibilty Repeativity Limit of quantitation Quantitative validation
41 IDENTIFICATION QUANTITATION Target Analysis Retention time Analytical standard 2 ions Recoveries Linearity Reproducibilty Repeativity Limit of quantitation Quantitative validation Non Target Analysis (low frequent com.) Retention time Analytical standard 1-2 ions(<5 ppm) Single point calibration Reproducibilty Repeativity Limit of detection/ quantitation Qualitative or Semi quantitative validation
42 IDENTIFICATION QUANTITATION Target Análysis Retention time Analytical standard 2 ions Recoveries Linearity Reproducibilty Repeativity Limit of quantitation Quantitative validation Non Target Analysis (low frequent comp.) Retention time Analytical standard 1-2 ions 2-3 ions(<5 ppm) no analytical Single point calibration Reproducibilty Repeativity Limit of detection/ quantitation Qualitative or Semi quantitative validation Informative standard, Rt?
43
44 Thank You for Your Attention
European Reference Laboratory - FV. Amadeo R. Fernández-Alba
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