Multi-component Analysis of Priority Pollutants in Foods using a GC Triple Quad MS/MS
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1 The world leader in serving science Multi-component Analysis of Priority Pollutants in Foods using a GC Triple Quad MS/MS Anton Mayer Thermo Fisher Scientific April 16, 29 ESAC 29
2 How many Pesticides need to be screened? The Pesticide Manual (14th ed.) includes 1,524 profiles 881 are comprehensive main entries 643 abbreviated entries of superseded products CAS numbers of pesticides EU Directive 25/396 Annex I covers 882 pesticides 2 independent SRMs are needed! DE DFG S19 Method 368 pesticides for GC 116 pesticides for LC (all new developments here) JP MHLW 26 Positive List with a total of 837 compounds ~ 4 pesticides for GC ~ 5 pesticides for LC And growing. 2
3 Why Choose a Triple Quad GC/MS? The matrix we are working requires a more selective way of analyses International regulations on the maximum residue levels of pesticides in food (MRLs) cover many hundreds of individual components at very low maximum residue limits in the range of only 1 ppb or even below [1]. More than 5 regulated pesticides can be analyzed by GC/MS 1. EU Commission Directives 91/414/EEC, 86/362/EEC, 86/363/EEC, 9/642/EEC, / Regulation (EC) N. 396/25 and subsequent amendments. 3
4 Current status in analysis of pesticide residues? More than 882 pesticides are regulated by EU* Total > 145. combinations MRL x Food Matrix Very low MRL established for some pesticides (.1 mg/kg) * Regulation (EC) No 396/25 and subsequent amendments and annexes 4
5 Worldwide Impact of Japanese Positive List - MRL 1ppb 5
6 Typical Workflow for Analysis of Pesticides Low volatility and high bp Volatility and boiling point of the pesticide analytes High volatility and low bp HPLC-MS/MS Clean (drinking water) Analysis of pesticides complexity and dirtiness of the matrix of the sample High fat (fish & meat) GC-ECD, NPD, FPD, GC-MS, GC-MS/MS Low fat (fruits & vegs) Homogenize sample Add IS Extract t and clean up multiple times Extract Clean up Concentrate 6
7 Typical pesticide multi-residue method setup Extraction Acetonitrile, Ethylacetate, Methanol... Clean-up GPC, SPE, LLE, column chromatography Determination GC, LC, GC/MS, LC/MS, GC/MS/MS, LC/MS/MS... 7
8 Pesticide residue methods pitfalls: Matrix complexity Number of analytes Number of samples Performance (LOD) Extraction Clean-up Determination Speed The complexity of samples requires a more selective way of analyses 8
9 Parameters to optimize: Selectivity it Sensitivity Speed 9
10 Workflow for Analysis of Pesticides in low fat matrices QuEChERS For: moisture > 75%, low fat fruits and vegetables LOQ: < 1 ng/g 229 pesticides AOAC Method Chop 1 kg sample Homogenize ca. 2 g subsample Mix and shake 15 g sample+15 ml 1% HAc in MeCN+1.5 g anh. NaAc+6 g anh. MgSO4+75 µl IS (4 ng/µl d1-parathion) to 5 ml FEP tube 1 min Centrifuge 35 g for 1 min 15 mg anh. MgSO4+5 mg PSA per ml extract in FEP tube LVI for GC 1 or 2 ml Transfer No LVI for GC 8 ml 15 mg anh. MgSO4+5 mg PSA per ml extract in FEP tube 3 s Mix and shake Mix and shake 3 s 35 g 1 min Centrifuge Centrifuge 35 g 1 min A B 1
11 AOAC 27.1 Method (QuEChERS) A Mix LVI GC.5 or 1 ml extract to GC vial Transfer 5 µl TPP (2 ng/µl) + 25 µl MeCN per.5 ml extract LC.15 or.3 ml to LC vial Mix 45 µl 6.7 mm formic acid per.15 ml extract Inject to LVI GC-MS/MS 8 µl Inject to LC-MS/MS 5-1 µl 11
12 AOAC 27.1 Method (QuEChERS) B GC 4 ml 4 µl TPP+1 ml toluene Transfer LC 25 µl 25 µl TPP+12.5 µl MeCN+6.7 mm formic acid to reach 25% MeCN in 5 mm formic acid Mix Mix Evaporate to.3-.5 ml Mix add toluene to 1 ml+anh. MgSO4 under N2 5-1 µl for LC-MS/MS Centrifuge 35 g 1 min Transfer.6 ml to GC vial Inject 2 µl for splitless GC-MS/MS 12
13 Triple Quadrupole GC/MS/MS vs. GC/MS Benefits of a triple quad over a Single Quad? Selectivity it (Selected Reaction Monitoring) i Lower detection limits Speed of analysis Matrix Elimination Robustness More than 5 pesticides can be analyzed by GC/MS TSQ Quantum GC Method workflow benefits: Less sample clean-up Faster response Lower costs (labor, solvents, consumables, waste disposal) 13
14 EC Directive 96/23/EC 14
15 Triple Quadrupole GC: Selected Reaction Monitoring Purpose of SRM: Quantitation on a single product ion Park Q1 on precursor ion e.g. Parathion m/z 291 Park Q3 on product ion SRM on m/z 19 15
16 TSQ Quantum GC: QED - SRM Switched to MSMS Purpose: Confirmation of a positive result Library Search for Identification Park Q1 on precursor ion e.g. Parathion m/z 291 Scan Q3 for the full product ion spectrum 16
17 Generic Method Proposal using GC-MS/MS Sample Prep Quechers (ITQ Tech Note 1236) Trace GC Ultra PTV preferred, SSL ok Quartz/Siltec liner 5% phenyl column, 3 m x.25 x.25 He flow programming TriPlus AS Standard 1-2 ul, or > 2 ul injections IonTrapQ for < 7 compounds MS/MS TSQ Q GC for >> 7 compounds SRM mode, most selective solution for dirty matrices 17
18 Comparison of GC/MS SIM and GC/MS/MS Quinoxyfen in 1 pg RT: Rela ative Abundance Abundance Relative Relative Abu undance Relative Abundan nce Relative Abundance DSQII SIM Mode RT: RT: TSQ Quantum GC MS/MS (SRM Mode) RT: NL: 6.37E4 m/z= F: + c SIM ms [ , , ] MS probe2f_sim NL: 2.67E4 m/z= F: + c SIM ms [ , , ] MS probe2f_sim NL: 9.94E3 m/z= F: + c SIM ms [ , , ] MS probe2f_sim RT: NL: 6.1E5 m/z= F: + c EI SRM ms [ ] 28 1] MS Genesis Probe2F RT: Time (min) NL: 1.6E6 m/z= F: + c EI SRM ms [ ] MS Genesis Probe2F 18
19 Product-Ion for transition 272 to 237 1pg RT: x1 RT: NL: 6.45E5 TIC F: + c EI SRM ms [ ] MS Genesis hopfenmix_1pgsrm dance Relative Abun Basislinie i x Time (min) 19
20 Lambda Cyhalothrin in Peach using GC-MS/MS NCI RT: NL: 3.86E3 m/z= F: - c CI SRM ms [ , ] MS 11FEB8_14 ative Abundance RelaPeach Sample 16 fg NL: 2.91E4 m/z= F: - c CI SRM ms [ , ] MS 11feb8_17 Re elative Abundance Standard 1pg Time (min) 2
21 Inside the TSQ Quantum GC Detection Q3 Q2 9 curved collision cell eliminates Neutral chemical noise DuraBriteXL EI/CI Ion Source Q1 Square rods for Q and Q2 are 3-4 x More efficient over hexapole or octopoles in ion transmission 21
22 The world leader in serving science Multi-Residue Analysis of Pesticides in Food* using H-SRM on the TSQ Quantum GC
23 Sample preparation* *Ministry of Health, Labour and Welfare Japan, Department of Food Safety, The Positive List System for Agricultural ral Chemical Residues in Foods, June 26, see: 2g sample 5ml ACN Extraction 1 min Filtration Salting out NaCl, phosphate buffer SPE clean-up GCB/aminopropylsilanized silica gel Elution with 2 ml of acetonitrile/toluene (3:1) Evaporate and transfer to acetone/n-hexane (1:1) Evaporation and dilution GC/MS/MS 23
24 Analytical GC-MS/MS Method: EI H-SRM GC TRACE GC Ultra Column : Injection mode : Injection Temp : Oven Temp : Flow : Transfer line Temp : Rti-5MS (Restek) or TRACE TR-5 Pesticide 3 m.25 mm I.D. df=.25 um Splitless with Surge (2 kpa,1 min) or PTV w/siltec baffeled Liner 24 SSL / 5 C PTV 8 (1 min) 2 /min 18 5 /min 28 (1 min) constant flow 1.2 min/min 28 MS TSQ Quantum GC Ion Source Temp : 22 Emission Current : 25 μa Ionization mode : EI Ion volume : Closed EI Analytical mode: SRM (Selected Reaction Monitoring) Scan width :.22 m/z Scan Time :.2 sec,.5 sec,.1 sec Peak Width for H-SRM: Q1:.4 Da, Q3:.7 Da Collision Gas Pressure : 1.2 mtorr (Ar) AS TriPlus Injection Volume : Injection mode : Syringe : 1 μl Hot Needle 8 mm Needle 24
25 Pesticide Method Overview TSQ Quantum GC ISO Name Formula Molecular Weight RT Precursor Ion Product Ion Coll. Energy nominal accurate min m/z m/z ev Hexachlorobutadiene (HCBD) C4Cl Hexachlorocyclohexane (HCH) C6H6Cl Hexaconazole C14H17Cl2N3O Hexazinone Hexythiazox C17H21ClN2O2S Imazalil C 14H 14Cl 2N 2O Imazamethabenz C15H18N2O Imibenconazole C17H13Cl3N4S Indoxacarb C22H17ClF3N3O (Extract from the alphabetical pesticide data base, worksheet Thermo) The total number of compounds currently is 67 with SRM information., Alanwood.net web pesticide database for structure and compound information is available as well. Comment to retention times: RTs may vary from sample to sample (matrix) and column to column (diameter, film thickness variations). Retention times will be provided as orientation on 2 different phases the universal TR-5Pesticides and the polar TR-35MS ongoing). 25
26 Thermo List Pesticide Residue List Compounds Pesticide id Compound List v1 Jan29.pdf 1 pages including transitions & energy 26
27 Multi-Residue Analysis: > 1 Pesticides Precursor Product Collision R 2 CV(%) Precursor Product Collision Range R 2 CV(%) Range Ion (m/z) Ion (m/z) Energy n=5 Ion (m/z) Ion (m/z) Energy n=5 Mevinphos Flutlanil XMC Hexaconazole Tecnazene Profenofos Ethoprpphos Uniconazole-P Ethalfluralin Pretilachlor Benfluralin Flamprop-methyl Monocrotophos Oxyfluorfen α-bhc Azaconazole Dicloran Bupirimate Simazine Thifluzamide Propazine Fenoxanil β-bhc Chlorbenzilate γ-bhc Pyriminobac-methyl-Z Cyanophos Oxadixyl Pyroquilon Triazophos Diazinon Fluacrypyrim Phosphamidon Edifenphos Prohydrojasmon Quinoxyfen δ-bhc Lenacil Prohydrojasmon Trifloxystrobin Benoxacor Pyriminobac-methyl-E Propanil Tebuconazole Phosphamidon Diclofop-methyl Dichlofenthion Mefenpyr-diethyl Dimethenamid Pyributicarb Bromobutide Pyridafenthion Paration-methyl Acetamiprid Tolclofos-methyl Bromopropylate Ametryn Piperophos Mefenoxam Fenpropathrin Bromacil Etoxazole Pirimiphos-methyl Tebufenpyrad Quinoclamine Anilofos Diethofencarb Phenothrin Cyanazine Tetradifon Chlorpyrifos Phenothrin Parathion Mefenacet Triadimefon Cyhalofop-buthyl Chlorthal-dimethyl Cyhalothrin Nitrothal-isopropyl Cyhalothrin Fthalide Pyrazophos Fosthiazate Bitertanol Diphenamid Pyridaben Pyrifenox-Z Cafenstrole Fipronil Cypermethrin Allethrin Halfenprox Dimepiperate Cypermethrin Quinalphos Cypermethrin Phenthoate Cypermethrin Paclobutrazol Fenvalerate Endosulfan-α Flumioxazin Butachlor Fenvarelate Imazamethabenz-methyl Deltamethrin+Tralomethrin Butamifos Tolfenpyrad Napropamide Imibenconazole
28 Standard Chromatogram Full Scan (63 comp.) RT: NL: 8.78E8 TIC MS Relative Abu undance Time (min) by Inge 28
29 17 Pesticide Run (5 pg/µl each) under 22 minutes! 29
30 Sensitivity - Spiked 1 ug/kg in Green Bell Pepper (1.2 pg injected on column) 27/3/29 15:57:47 Rti-5MS scan time.1 SETTIME=.1 RT: SM: 5G NL: 3.18E @cid15. Pyrifenox-Z [ ] MS RT: SM: 5G NL: 1.71E4 1 Endosulfan-α 24.86@cid15. [ ] MS 5 RT: SM: 5G NL: 4.89E4 1 Profenofos @cid15. [ ] MS NL: 6.26E @cid25. Fipronil [ ] MS NL: 1.81E @cid1. Butachlor [ ] MS NL: 5.46E4 Uniconazole-P 234.1@cid15. [ ] MS NL: 4.43E @cid1. [ ] MS NL: 9.39E @cid15. [ ] MS Dimepiperate Butamifos Pretilachlor NL: 6.63E @cid1. [ ] MS NL: 6.6E @cid1. [ ] MS NL: 1.68E @cid5. [ ] MS Phenthoate Napropamide Framprop -methyl NL: 3.95E @cid1. [ ] MS NL: 1.52E @cid1. [ ] MS NL: 6.22E @cid15. [ ] MS NL: 2.85E @cid1. [ ] MS Quinalphos Flutranil Oxyfluorfen NL: 1.28E @cid15. [ ] MS NL: 2.68E @cid15. [ ] MS NL: 2.4E @cid15. [ ] MS Paclobutrazol Hexaconazole Azaconazole Time (min) Time (min) Time (min) 3
31 Sensitivity at 1/1 MRL - 1 ppb in Green Bell Pepper 27/3/29 15:57:47 Rti-5MS scan time.1 SETTIME=.1 RT: SM: 5G NL: 2.71E @cid1. Bupirimate [ ] MS 5 RT: SM: 5G 17.3 NL: 3.32E @cid1. Triazophos [ ] MS RT: SM: 5G NL: 1.93E5 1 5 Pyriminobac -methyl-e 32.2@cid15. [ ] MS NL: 9.5E @cid1. Thifluzamide [ ] MS NL: 4.61E @cid1. Fluacrypyrim [ ] MS NL: 5.74E4 Tebuconazole 25.3@cid2. [ ] MS NL: 3.54E @cid2. [ ] MS NL: 4.48E @cid1. [ ] MS NL: 7.13E @cid15. [ ] MS Fenoxanil Edifenphos Diclofop-methyl NL: 2.9E @cid15. [ ] MS NL: 1.59E @cid1. [ ] MS Chlorbenzilate Quinoxyfen Mefenpyr -diethyl NL: 1.6E @cid2. [ ] MS Pyriminobac -methyl -Z NL: 2.12E @cid15. [ ] MS NL: 7.33E @cid15. [ ] MS -E Lenacil Pyributicarb NL: 2.4E @cid1. [ ] MS NL: 6.54E @cid1. Oxadixyl [ ] MS 1 5 Trifloxystrobin 18.1 NL: 2.6E @cid1. [ ] MS 1 5 Pyridafenthion NL: 5.E @cid1. [ ] MS Time (min) Time (min) Time (min) 31
32 TSQ Quantum GC Tetradifon in Grapefruit 5 Tetradifon Y = *X R^2 =.9992 W: Equal RT: SM: 3B 1 95 RT: NL: 2.E4 TIC F: + c CI SRM ms @cid1. 9 [ ] MS ICIS std_4 85 Area ppb % RSD at 5 PPB Time (min) lative Abundance Re 32
33 Multimethod Pesticides: Low LOQ pg on-column Pesticide TSQ Quantum GC LOQ (s/n > 1) Bromopropylate 1.1 Chlorpyrifos.1 Cypermethrin-1 2 Cypermethrin-2 2 Cypermethrin-3 2 Cypermethrin-4 2 Deltamethrin+Tralomethrin.2 Diazinon.1 Endosulfan-α.1 Fenpropathrin.1 Fenvalerate Fenvarelate-2.1 Fipronil.1 Mevinphos.1 33
34 Multi-Pesticides: Quantum GC- pg on-column with Green Bell Pepper spiked standards Pesticide TSQ Quantum GC (LOQ) Parathion 1.1 Phenothrin-1 5 Phenothrin-2.1 Phenthoate.1 Phosphamidon-1.1 Pirimiphos-methyli i.1 Triadimefon.1 Tetradifon.2 Triazophos.2 α-bhc.1 β-bhc.1 γ-bhc.1 Note: Lowest calibration limits it as LOQ for Quantum GC, S/N 1:11 34
35 QuEChERS approach Final extract contains many co-extractives from the matrix The complexity of samples requires a more selective way of determination Highly Selective Reaction Monitoring au resolution o on the TSQ Quantum GC 35
36 SRM with Unit Resolution Q3 Q1 Q2 256,3 48,4 48,2 256,22,7 Da,7 Da 36
37 Thermo Scientific TSQ - H-SRM precursor selection Q3 Q2 Q1 256,3 48,4 7Da,7 48,2 4Da,4 37
38 Quadrupole Performance Characteristics; TSQ Quantum GC uses Hyperbolic Rods for Q1 and Q3 for maximum performance Comparision of hyperbolic and round rod quadrupole performance Hyperbolic rods Round rods 38
39 Selectivity with H-SRM for Food Samples C:\Xcalibur\...\greapfruits_spiked_1ppb Rti-5MS scan time.5 SETTIME=.1 3/29/27 4:58:44 AM greapfruits_spiked_1ppb RT: RT: Da Relative Abundance Time (min) NL: 2.23E4 TIC F: + c CI SRM ms @cid15. [ ] MS greapfruits_spiked_1 ppb Cl Hexaconazole In Grapefruit N N N OH Cl greapfruits_spiked_1ppb_ /29/27 12:27:58 PMgreapfruits_spiked_1ppb Rti-5MS scan time.5 SETTIME=.1 HSRM RT: RT: 15.6 Relative Abundance Da Time (min) NL: 2.67E @cid15. [ ] MS greapfruits_spiked_1ppb _ Rti-5MS scan time.5 SETTIME=.1 RT: elative Abundance Re Da /29/27 12:55:2 AM RT: 12.6 NL: 9.82E3 TIC F: + c CI SRM ms @cid15. [ ] MS greenpaprika p _ spiked _ 1ppb Parathion Green-Bell Pepper O O O P S _ /29/27 1:26:2 AM Rti-5MS scan time.5 SETTIME=.1 HSRM RT: RT: 12.6 NL: 9.77E @cid15. [ ] MS greenpaprika_spiked_1ppb_ Relative Abundance Da N Time (min) Time (min) N O O R
40 SRM vs H-SRM: Flamprop-methyl in Grapefruit 1 ppb spiked RT: SRM - unit RT:15.66 O N NL: 2.49E4 O O RT: 1 RT: H-SRM NL: 1.93E Cl 7 65 F Relative Abundance Relative Abundance Time (min) Time (min) 4
41 GC Triple Quadrupole MS/MS in pesticide analysis Conclusions Unique Target Compound Selectivity with au, QED MS/MS spectra and Chemical Ionization modes Superior Sensitivity Trace levels at your syringe tip Q and Q2 square rods for 3-4x improved ion transmission over octapole or hexapole designs 9 curved Q2 collision cell for neutral noise elimination Superior Results with Complex Matrix Samples Less extensive sample clean-up Lower costs Reliable quantitation peak integration Faster 2ms per transition Confirmation of Positive Compounds In one run full QED MS/MS spectra TSQ Quantum GC Ease-of-Use and Maintenance friendly DuraBrite XLIon source design 41
42 Thank you very much for your attention! 42
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