Unique Benefits of Orbitrap MS Technology for the Comprehensive Analysis of Polar and Non-polar Pesticides
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1 Unique Benefits of Orbitrap MS Technology for the Comprehensive Analysis of Polar and Non-polar Pesticides Richard J.Fussell 1, Carmen Ferrer 2 and Sergio Guazzotti 1 1 Thermo Fisher Scientific, 2 University of Almeria PO72485-EN 817S The world leader in serving science
2 Outline Overview of Pesticides workflow Features of the different Thermo Scientific TM Orbitrap TM MS Technologies Benefits of Orbitrap MS Technology Non targeted and targeted acquisition of small molecules Detection, quantification and identification Retrospective analysis Examples to demonstrate the performance of systems 2
3 Comprehensive Analysis of Pesticide Residues MRMs SRMs IC-MS gylphosate phosphine GC-MS LC & GC LC-MS (RP) Polar pesticides chlorate/ paraquat/ perchlorate diquat dithios Targeted acquisition: expected residues QQQ provides the selectivity and sensitivity to meet MRL requirements. Non-targeted acquisition: expected, suspected and unexpected residues High Resolution Accurate Mass (HRAM) MS provides: Similar sensitivity Improved selectivity & quantification Simplicity of FS method set-up Increased scope Retrospective analysis Flexibility in fragmentation (LC-MS) 3
4 Workflow- Analysis of Extracts Thermo Scientific TSQ Endura Triple Quadrupole Mass Spectrometer IC-(Thermo Scientific Dionex ICS-5+ Reagent-Free HPIC system) MS/MS QuEChERS NL SweEt Thermo Scientific TSQ 8 Evo Triple Quadrupole GC-MS/MS Targeted analysistriple quadrupole MS/MS QuPPe methanol/water (polar pesticides) Simultaneous Targeted & Non- Targeted Analysis: Orbitrap-MS (detection, quantification, identification, screening) Thermo Scientific Q Exactive Focus Hybrid Quadrupole-Orbitrap Mass Spectrometer Thermo Scientific Exactive GC Orbitrap GC-MS Thermo Scientific Dionex Integrion HPIC System - can be coupled to Orbitrap MS 4
5 Redefining Routine Pesticides Analysis Exactive GC system Resolving Power Mass Accuracy Up to 6, at m/z 2 < 1ppm Sensitivity Dynamic Range ppt >6 orders Redefining Routine GC-MS EI/CI; Full-scan; Timed-SIM EI Spectra searchable against the NIST Library 5
6 QE GC-Orbitrap MS Resolving Power Resolving power ~1/ m/z GC-EI: 278 ions for 574 pesticides K (m/z 2) K (m/z 2) 3K (m/z 2) 15K (m/z 2) 2 Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 6
7 GC-HRAM Linearity Curve from.5 to 5 ng/g (triplicate at each level) R 2 =.9999 Fenpropimorph calibration curve in leek matrix. For all pesticides, the coefficient of determination (R 2 ) was >.99 with an average value of R 2 =.997 7
8 Spectral Quality vs Amount Injected RT: SM: 5B NL: 3.21E4 1 m/z= F: FTMS + p EI Full ms 8 [5.-5.] MS 1532_8 7 Relative Abundance Time (min).1 pg Solvent standard hexachlorobenzene (6K) NIST RT: SM: 5B NL: 9.5E m/z= F: FTMS + p EI Full ms 8 [5.-5.] MS 1532_ , pg Relative Abundance Time (min) Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 8
9 Selectivity (chlorpropham in leek, 1 ppb) Nominal mass Full scan MS XIC m/z ±.5 Da 127 ±.5 Da bu da ce e at e Nominal Mass MS/MS HRAM Full scan MS XIC m/z ± 5 ppm Relative Abundance ative Abundance ±.6 Da RT: RT: 11.5 MA: Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 9
10 Limit of Quantification: Exactive GC system QuEChERS - 1µL Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 1
11 Limit of Identification: Exactive GC system QuEChERS - 1µL Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 11
12 High Sensitivity Full-scan 15 compounds in mixed vegetable matrix Triple-quadrupole-level sensitivity possible with a non-target acquisition *Acquired on the Q Exactive GC system the Exactive GC system provides equivalent performance. 12
13 Repeatability of Injection: LVI (5µL) 5 μl QuEChERS (ACN) extract of leek Various pesticides, 25 pg/μl Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 13
14 Automated Qualitative Screening Workflows Quantitative method with all associated AQC for usual suspects (~1) Automated qualitative screening: lower AQC burden for unexpected pesticides Same raw data files, but 2 different data processing approaches 1. Library: match of EI-spectra deconvolution of HR spectra cleaned spectrum Library search (NIST, PEST library) 2. Database: RT + 2 exact masses RT ±.5 min XICs ± 5 ppm 2 ions (w/o ratio criterion) Software: Report if match (SI) > user threshold. (The analysts manually review hits) Software: Report if signal is found for both ions (The analysts manually review hits) 1 µg/kg found out of 5 Tomato 47 Orange 44 Leek 43 Data courtesy of Dr Hans Mol, Rikilt Wageningen, UR 14
15 Thermo Scientific Application Note 169 Identification Point Retention time Quan ion Tolerance Primary ID.1 minutes 5 ppm Optional additional ID Identifcation ion 5 ppm Ion ratio < 3% Additional ions 5 ppm Isotopic pattern match > 7% NIST spectral match > 6 51 pesticides were prepared in tomato, leek and orange at concentrations equivalent to.5, 1, 2, 5, 1, 2, 5, 1, 2 and 5 μg/kg. 15
16 Ion Chromatography-Mass Spectrometry: Polar Ionic Pesticides The world leader in serving science
17 IC-MS/MS Configuration Dionex Integrion HPIC System High- Pressure Non-Metallic Pump Eluent Generator (OH or H + ) Makeup Pump (MeCN) CR-TC Waste Sample Inject (Autosampler) Separation Column AS 19 Electrolytic Eluent Suppressor Conductivity Detector.31 µs Data Management 17
18 Glyphosate: IC-QQQ Analysis of QuPPe Extracts of Wheat Flour Stable retention times AMPA 1 µg/kg Multi-analyte capability Glyphosate Glufosinate Fosetyl 11.1> >62.9 N-acetyl glyphosate N-acetyl glufosinate Phosphonic acid AMPA 3-MPPA chlorate N-acetyl AMPA ethephon perchlorate Data Courtesy of Fera Science Ltd UK 18
19 Polar Ionic Pesticides (QuPPE) w/wo IS Correction (Grape) Compound Glyphosate AMPA N-acetyl AMPA Glufosinate 3-MPPA N-acetyl Glufosinate Perchlorate Chlorate Ethephon Fosetyl-Al Phosphonic acid Conc n (ng/g) Mean % Rec (n=5) IS Corrected Mean % RSD Mean % Rec (n=5) Not corrected Mean % RSD IS not available Data Courtesy of Fera Science Ltd UK 19
20 Polar Ionic Pesticides (QuPPE) w/wo IS Correction (wheat flour) Compound Glyphosate AMPA N-acetyl AMPA Glufosinate 3-MPPA N-acetyl Glufosinate Perchlorate Chlorate Ethephon Fosetyl-Al Phosphonic acid Conc n (ng/g) Mean % Rec (n=5) IS Corrected Mean % RSD Mean % Rec (n=5) Not corrected Mean % RSD IS not available Data Courtesy of Fera Science Ltd UK
21 Analyteguru.com IC-MS: The Solution to the Problem Analysis of Polar Pesticides? The High Capacity of Dionex Ionexchange Columns The Robustness of Ion-exchange Columns Compatibility with Mass Spectrometers Independent Results in Compliance with Accepted Guideline Criteria A Commitment to Continuous Method Improvement 21
22 IC-MS Publication Stuart Adams et al J. Agric. Food Chem, 217 on-line 22
23 Polar Analytes Glyphosate (m/z ) N-acetyl glyphosate (m/z ) Chlorate (m/z ) Perchlorate (m/z ) Aminomethylphosphonic acid (AMPA) (m/z 11.12) Fosetyl-aluminium (m/z 19.6) N-acetyl aminomethylphosphonic acid (N-acetyl AMPA) (m/z ) Phosphonic acid (m/z ) Br - Bromide ion (m/z ) Etephon (m/z ) Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 23
24 Extracted Ion Chromatograms of Precursor ng/g 1 5 Glyphosate Relative Abundance AMPA N-acetyl glyphosate Bromide ion N-acetyl AMPA Ethephon 1 5 Chlorate 7 73 Relative Abundance Fosetyl- Al Time (min) Phosphonic acid Perchlorate Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 24
25 Glyphosate- Sensitivity Improvement in MS 2 RT: Relative Abundance A) B) 5 C) mg/kg of glyphosate in carrot. A) ± 5 ppm extracted from full scan MS(m/z ) B) ± 5 ppm extracted from PRM MS 2 C) ± 5 ppm extracted from PRM MS 2 Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 25
26 Validation of IC - Orbitrap Method: Peak Area Repeatability.1 mg/kg solvent orange onion tomato.5 mg/kg melon carrot Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 26
27 Validation of IC-Orbitrap Method: Linearity.1-.5 mg/kg AMPA Chlorate Perchlorate Glyphosate Fosetyl- Al Phosphonic acid Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 27
28 Modified QuPPe-PO Weigh sample homogenate in 5 ml centrifuge tube Fresh fuits and vegetables (high water content): 1 ±.1 g Adjust water content of sample to 1 ml Add 1 ml MeOH Add 25 μl IS (2 ppm) ( 13 C-Glyphosate & 18 O 3 -Chlorate) Shake automatically 5 min Centrifuge at 4 rpm for 5 min Transfer 4 ml supernatant into a plastic vial IC-MS analysis Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 28
29 Analysis of Real Samples Aubergine.51 mg/kg of chlorate quantifier qualifier Zucchini.75 mg/kg of perchlorate quantifier qualifier Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 29
30 Analysis of Real Samples: More Examples Baby food.26 mg/kg of phosphonic acid quantifier qualifier Orange.239 mg/kg of fosetyl-al quantifier qualifier Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 3
31 Q Exactive Focus hybrid quadrupole Orbitrap MS The world leader in serving science
32 Redefining Routine LC-MS Analysis of Pesticides Q Exactive Focus Hybrid Quadrupole-Orbitrap MS vdia is not available in the U.S. Mass Range 5 < m/z < 2, m/z 2 Top N 2 Mass Accuracy Polarity Switching Flexible Acquisition 17,5 at 12 Hz 35, at 6 Hz 7, at 3 Hz < 1ppm RMS, Internal Calibration < 3ppm RMS, External Calibration one full cycle 35. RP in <1sec Full scan dd-ms 2 AIF vdia PRM (SIM) 32
33 Acquisition: Q Exactive Focus MS System And more! vdia is not available in the U.S. 33
34 LC-HRAM - Does Resolving Power Matter? Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 34
35 Possible Workflows in LC-Q-Orbitrap Full scan MS Nontarget MS 2 All Ions Fragmentation (AIF) Full scan MS Target MS 2 Data dependent MS2 (dd-ms2) Full scan MS Target MS 2 Nontarget MS 2 FS/dd-MS 2 /AIF-MS 2 Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 35
36 Pesticides Detected in Routine 464 pesticides 516 matrices 33,5 samples 141 pesticides Data provided by Courtesy Prof. Amadeo Rodríguez Fernández- Alba, University of Almeria, Spain, 36
37 LC- Q Orbitrap Method Target (166 compounds) FS-ddMS 2 Non-target (12 compounds)-aif-ms2 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 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 Courtesy Prof. Amadeo Rodríguez Fernández- Alba, University of Almeria, Spain, 37
38 FS/dd-MS2/AIF-MS2 Pyridaben (target compound).1 mg/kg in orange MS MS 2 Fragment ions detected in Data dependent MS 2 Fragment ion detected in AIF-MS 2 Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain 38
39 Validation: Linearity of Response in Spinach 2.E+9 1.8E+9 1.6E+9 1.4E+9 1.2E+9 1.E+9 8.E+8 6.E+8 4.E+8 Pirimiphos-methyl Ethoprophos 2.E+8.E Flusilazole Concentration [mg/kg] Courtesy Prof. Amadeo Rodríguez Fernández- Alba, University of Almeria, Spain, 39
40 Validation: Repeatability of Residue Concentrations % of Compounds 1% 9% 8% 7% 6% 5% 4% 3% 2% 1% %.1 mg/kg <5% 5-1% 1-15% 15-2% >2% Courtesy Prof. Amadeo Rodríguez Fernández- Alba, University of Almeria, Spain RSD (%) % of Compounds Tomato Orange 1% 9% 8% 7% 6% 5% 4% 3% 2% 1% %.5 mg/kg <5% 5-1% 1-15% 15-2% >2% RSD (%) 4
41 Analysis of Real Samples: Quantification Concentration (mg/kg) Matrix LC-Q-Orbitrap- Compound LC-QqQ-MS/MS MS/MS Diff (%) Conferencia Pear1 Boscalid Difenoconazole Diflubenzuron Imazalil Imidacloprid Pyraclostrobin Tebuconazole Thiacloprid Trifloxystrobin Conferencia Pear2 Boscalid Difenoconazole Fluopyram Imazalil Imidacloprid Pyraclostrobin Tebuconazole Red Pepper Flutriafol Red Chili Pepper Flutriafol Pirimicarb Banana Imazalil Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain 41
42 Validation of Method: Stability of Mass Accuracy Error (mda) Day Carbendazim-d 3 Malathion-d 1 Error (mda) Day Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain 42
43 Analysis of Real Samples: Imazapyr in Pears DETECTION OF NON-TARGET PESTICIDES not included in EU Monitoring Program protonated molecule = m/z RT: Relative Abundance Full scan MS AIF MS 2 AIF MS ± 5ppm ± 5ppm ± 5ppm 1 5 AIF MS ± 5ppm Time (min) Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain 43
44 Analysis of Real Samples: Diafenthiuron Metabolite in Pepper DETECTION OF NON-TARGET PESTICIDES Diafenthiuron urea (metabolite of diafenthiuron) in pepper mass of protonated molecule = m/z RT: SM: 9G Full scan MS ± 5ppm 1.93 Relative Abundance AIF MS ± 5ppm AIF MS ± 5ppm Time (min) Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain, 44
45 Analysis of Real Samples: Summary additional pesticides not included in the scope of the LC-QQQ Courtesy Prof. Amadeo Rodríguez Fernández-Alba, University of Almeria, Spain 45
46 Benefits from Utilization of Orbitrap MS technology Highest resolution and stable excellent mass accuracy at the low m/z s of interest Simultaneous targeted and non-targeted analysis in a single analysis Quantification of residues at least equal to triple quadrupole technology The highest selectivity for the accurate determination of residue concentrations in difficult matrices Increased scope- acquiring all of the information all of the time The possibility of retrospective analysis Proven robust instrumentation The benefits of ion chromatography: add a new capability to the workflow facilitating the migration of ionic pesticides into multi-residue method High capacity columns to cope with high matrix load to provide more resolution and retention time stability Robust columns and technology proven over 4 years of development 46
47 Thank You For Your Attention Stay Connected with Us Please join at our booth where we will address further comments and questions. Analyte Guru Blog Solutions For More Resources visit our Food and Beverage Website 47
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