53rd Annual North American Chemical Residue Workshop · 53rd Annual North American Chemical Residue...

European Reference Laboratory - FV

53rd Annual North American Chemical Residue Workshop


18th July 2016



Pyrimethanil [M+H+] m/z 200.1182 0.01 mg/ kg in onion RT = 7.05 min Dilution 5x

200.1182 ± 1 Da

200.1182 ± 0.001 Da

Pyrimethanil at 0.01 mg/kg



MILLING

SAMPLE EXTRACTION

LC MS/MS

GC MS/MS

EVALUATION

REPORT



LC-QqQ, n=185 (Ratio SRM2/SRM1)

CE (V)

1. Acephate (10 %) 15 2. Carbendazim (4 %) 20 3. Clomazone (2 %) 10 4. Cyazofamid (3 %) 10 5. Dichlorvos (14 %) 30 6. Diniconazole (12 %) 28 7. Fipronil (12 %) 28 8. Fludioxonil (12 %) 5 9. Hexaconazole (10 %) 30 10. Isofenphos methyl (11 %) 15 11. Isoxaflutole (8 %) 50 12. Mepanipyrim (10 %) 20 13. Metconazole (7 %) 48 14. Paclobutrazol (6 %) 36 15. Pencycuron (9 %) 60 16. Spinosyn A (2 %) 20 17. Spinosyn D (1 %) 20 18. Tebuconazole (5 %) 20 19. Thiacloprid (6 %) 10 20. Thiobencarb (7 %) 10 21. Triadimenol (4 %) 5 22. Triazophos (8 %) 10 23. 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 %) 20 2. 4,4’-DDE (12 %) 20 3. Bifenthrin (5 %) 40 4. Bromopropylate (8 %) 20 5. Cadusafos (11 %) 10 6. Chlozolinate (11 %) 5 7. Cypermethrin (11 %) 20 8. Ethoxyquin (14 %) 30 9. Fenpropidin (10 %) 3 10. Heptachlor (10 %) 40 11. Heptenophos (3 %) 10 12. Isocarbophos (7 %) 8 13. Isofenphos-methyl (9 %) 10 14. Paclobutrazole (13 %) 20 15. Secbumeton (10 %) 5 16. Tetrachlorvinphos (14 %) 35

In red, low collision energies

In green, high collision energies



Acquisition Time (m

10 10.1 10.2 10.3 10.4 10.5 10.6 10.7 10.8

Co

un

ts 4x10

-0.5

0

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5

5.5

240.1 -> 124.9 , 240.1 -> 127.8

Ratio = 1.8 (91.5 %)

Clomazone

Transitions at 0.05 mg/kg in tomato LC-QQQ-MS/MS

Acquisition Time (m

2.7 2.8 2.9 3 3.1 3.2 3.3 3.4 3.5

Cou

nts

4x10

-0.1

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1

1.1

1.2

1.3

1.4

1.5

1.6

1.7

1.8

1.9

192.0 -> 160.0 , 192.0 -> 132.0

Ratio = 4.4 (94.9 %)

Carbendazim

Ratio: 4% Ratio: 2%



Mass Data base components- orange matrix compounds (1 g/mL)

8017 Matrix compounds

m/z: 100-700 Rt: 4-8 min

m/z: 100-400 Rt: 7-13 min

DB: 750 components

Orange: 2743 matrix compounds

Miner 3D Enterprise


2x10

0

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5

+ESI MRM Frag=380.0V CF=0.000 DF=0.000 [email protected] (318.0

* 9.174

2x10

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5

+ESI MRM Frag=380.0V CF=0.000 DF=0.000 (318.0000 -> 26

* 9.150

Counts vs. Acquisition Time (min)

8.7 8.8 8.9 9 9.1 9.2 9.3 9.4 9.5 9.6

2x10

0

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.174

2x10

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.174


8.7 8.8 8.9 9 9.1 9.2 9.3 9.4 9.5 9.6

2x10

0

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.162

2x10

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.162


8.7 8.8 8.9 9 9.1 9.2 9.3 9.4 9.5 9.6

2x10

0

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.162

2x10

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.162


8.7 8.8 8.9 9 9.1 9.2 9.3 9.4 9.5 9.6

2x10

0

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.174

2x10

0.5

1

1.5

2

2.5

3

3.5

4

4.5

5


* 9.174


8.7 8.8 8.9 9 9.1 9.2 9.3 9.4 9.5 9.6

Std in solvent at 10 µg/L

Ethyl Acetate method

NL method Citrate QuEChERS without clean-up method

Citrate QuEChERS method

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%

Azinphos methyl at 10 µg/kg in Onion. LC-QqQ-MS/MS

http://www.clipartsfree.net/large/6390-ok-button-clipart.html

http://www.viewpsd.com/wp-content/uploads/2013/04/delete-button.jpg





EUPT Sample: coriander

Linuron Standard in solvent Ion ratio: 1.8

Linuron (0.125 mg/kg) Real sample of coriander Ion ratio: 2.4

FALSE NEGATIVE



EUPT Sample of coriander

LC-HRAMS

Linuron

Matrix interference



LC-Orbitrap

RT: 0.00 - 12.11 SM: 3G

0 1 2 3 4 5 6Time (min)

0

20

40

60

80

1000

20

40

60

80

100

Re

lativ

e A

bu

nd

an

ce

4.21

4.22

Full scan MS 192.0768 ± 5ppm

AIF MS2

160.0506 ± 5ppm

Mass error -0.5 ppm (-0.1 mDa)

Mass error -1.9 ppm (-0.3 mDa)

Carbendazim, 0.01 mg/kg in Tomato



MASS ACCURACY RESOLUTION



0

20

40

60

80

0.1 0.01 0.005 0.001 0.0005 495 49 25 5 2

(Da) (ppm)

Thiabendazole C10H7N3S (m/z 202.0433)

C0-25H0-50N0-5O0-5Cl0-5Br0-5S0-5

Num

ber o

f pos

sibl

e m

olec

ular

form

ulas

5 ppm

~ 2 000 ~ 20 000 ~ 40 000 ~ 200 000 ~ 400 000 (FWHM) Resolution

Resolution ~ 70 000 FWHM

9 molecular formulas


- Cl, Br

~ 70 000 ~25 000

Absolute mass error relative to Thiabendazole

Resolution ~ 25 000 FWHM



- Cl, Br



Influence of resolution on detection

317.00 317.05 317.10 317.15 317.20 317.25 317.30 317.35m/z

0

10

20

30

40

50

60

70

80

90

1000

10

20

30

40

50

60

70

80

90

100

Rel

ativ

e Ab

unda

nce

317.1657

317.2014

317.1728

317.1966

317.1544

Exact mass of bupirimate: 317.1642

Matrix ion. Mass error 27.1 ppm

Matrix ion. Mass error -30.1 ppm

Resolution 17500

Resolution 70000

Two non resolved matrix ions. Mass error 4.7 ppm False detect of bupirimate

317.1728

317.1657

317.2014

317.1966

317.1544



Identification criteria (EU)

Quantitation LOQ, Linearity, Reproducibility,…



Combining Full Scan MS and MS2

Mode



70k 70k

FS/dd-MS2

FS/AIF-MS2

0.27 s 0.6 s

Orbitrap Full scan MS

MS2

17,5 K

Target MS2 analysis. Fragmentation is carried out only if precursor ion is detected in full scan MS. List of precursor ions is necessary.

Non-target MS2 analysis. Fragmentation is carried out during entire chromatographic run. No precursor selection. No list of precursor ions is present.

70k 17.5 k



Pepper spiked at 0.01 mg/kg metlaxyl

Grapefruit Real sample 1

Metalaxyl (XIC m/z 280.1543 ± 5 ppm). Full scan MS. Resolution 70000

Grapefruit Real sample 2

Analysis of real samples by LC-HRAMS MS2



Metalaxyl (XIC m/z 280.1543 ± 5 ppm). Full scan MS. Resolution 70000

Expected fragments: 148.1119 160.1119 192.1380 220.1380

LC-QOrbitrap (QExactive)

Grapefruit Real sample

FALSE POSITIVE

XIC m/z 280.1543 ± 5 ppm

XIC m/z 280.1543 ± 5 ppm

Standard of Metlaxyl

280.1547

MS spectrum Experimental MS/MS spectrum

Library MS/MS spectrum

192,1382

191,0603



Pesticides Full scan QTOF Orbitrap MS2 QTOF Orbitrap Azoxystrobin 404.1241 -1.5 0.0 372.0979 0.6 -0.3 Diazinon 305.1083 -1.5 0.3 169.0794 0.9 0.0 Dichlorvos 220.9532 0.5 0.5 109.0047 -1.9 1.6 Fenamiphos - sulfone 336.1029 -0.2 0.6 266.0246 -1.6 0.4

Profenofos 372.9424 1.9 0.5 302.8642 1.0 -0.3

Pesticides Full scan QTOF Orbitrap MS2 QTOF Orbitrap Azoxystrobin 404.1241 0.4 0.0 372.0979 1.4 0.3 Diazinon 305.1083 1.2 -0.3 169.0794 -1.1 -0.6 Dichlorvos 220.9532 1.9 -0.5 109.0047 -2.3 2.4 Fenamiphos - sulfone 336.1029 -0.2 0.0 266.0246 1.5 0.0

Profenofos 372.9424 -0.4 0.0 302.8642 1.1 -1.0

Tomato

Orange

0.01 mg/kg

0.01 mg/kg



MILLING

SAMPLE EXTRACTION

LC MS/MS

GC MS/MS

EVALUATION

REPORT

HRAMS


SENSITIVITY LINEARITY + REPRODUCIILITY



11 Matrices

Cucumber Orange Green bean

Apple

Lettuce

Onion

Tomato

Parsley Leek

Garlic Spinach



LOQ

0%10%20%30%40%50%60%70%80%90%

100%

0.01mg/kg

0.02mg/kg

0.05mg/kg

ddMS2

AIF

0%10%20%30%40%50%60%70%80%90%

100%

0.01mg/kg

0.02mg/kg

0.05mg/kg

ddMS2

AIF

Tomato Apple

0%10%20%30%40%50%60%70%80%90%

100%

0.01mg/kg

0.02mg/kg

0.05mg/kg

ddMS2

AIF

Orange

0%10%20%30%40%50%60%70%80%90%

100%

0.01mg/kg

0.02mg/kg

0.05mg/kg

ddMS2

AIF

Onion

% o

f com

poun

ds

% o

f com

poun

ds

% o

f com

poun

ds

% o

f com

poun

ds Target MS2

Non Target MS2 (AIF)

Target MS2


Target MS2


Target MS2

Non Target MS2 (DIA)

LC-Orbitrap QExactive Focus



Identification 166 pesticides x 11 matrices = 1826 results

% o

f com

poun

ds

0%

10%

20%

30%

40%

50%

60%

70%

80%

90%

100%

ddMS2 AIF

0.01 mg/kg0.1 mg/kg

LC-Orbitrap QExactive Focus



Linearity LC-HRAMS

0.0E+00

2.0E+08

4.0E+08

6.0E+08

8.0E+08

1.0E+09

1.2E+09

1.4E+09

1.6E+09

1.8E+09

2.0E+09

0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6

Concentration [mg/kg]

Pirimiphos-methyl

Ethoprophos

Flusilazole

Are

a

Spinach

0.07 0.14 0.21 0.28 0.35 0.42 0.49

Azoxystrobin

Imidacloprid

Zoxamide



HRAMs No HRAMs Homogeneity: 0,085 mg/kg

+25%

-25%

-50%

50%

EU Proficiency Test



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 0.168 0.154 8 Difenoconazole 0.027 0.029 -7 Diflubenzuron 0.014 0.017 -21 Imazalil 1.711 1.334 22 Imidacloprid 0.047 0.052 -11 Paclobutrazole < LOQ < LOQ - Pyraclostrobin 0.114 0.096 16 Tebuconazole 0.048 0.048 0 Thiacloprid 0.037 0.036 3 Trifloxystrobin 0.024 0.021 13 Conferencia Pear_M Boscalid 0.175 0.177 -1 Difenoconazole 0.012 0.013 -8 Fluopyram 0.027 0.026 4 Imazalil 1.359 1.093 20 Imidacloprid 0.053 0.061 -15 Kresoxim Methyl < LOQ < LOQ - Pyraclostrobin 0.067 0.063 6 Tebuconazole 0.044 0.047 -7 Red Pepper Fluopyram < LOQ < LOQ - Flutriafol 0.019 0.013 32 Red Chili Pepper Flutriafol 0.397 0.368 7 Pirimicarb 0.034 0.034 0 Green Pepper Flutriafol < LOQ < LOQ - Metalaxyl 0.010 0.010 0 Banana Imazalil 0.915 0.788 14 Carrot_E - < LOQ < LOQ - Carrot_M - < LOQ < LOQ -



02000000400000060000008000000

1000000012000000140000001600000018000000

0 2 4 6 8 10 12

Area

Day

Carbendazim d-3

0

2000000

4000000

6000000

8000000

10000000

12000000

0 2 4 6 8 10 12

Area

Day

Malathion-d10

Robustness of peak area LC-Orbitrap

+ 20%

- 20%

+ 20%

- 20%



Robustness of mass accuracy LC-Orbitrap

-1.0

-0.6

-0.2

0.2

0.6

1.0

0 2 4 6 8 10 12

Erro

r [pm

Da]

Day

Carbendazim d-3

-1.0

-0.6

-0.2

0.2

0.6

1.0

0 2 4 6 8 10 12

Erro

r [pp

m]

Day

Malathion-d10



Data provided by

Scope: 464 pesticides 516 matrices 33500 samples

141 pesticides reported



Non-target MS2 Full scan MS

Target MS2 Full scan MS

Target MS2 Non-target MS2 Full scan MS



70k 17,5k

70k 70k

FS/dd-MS2

FS/AIF-MS2

Orbitrap Full scan MS

MS2 17,5 K

Target MS2 analysis. Fragmentation is carried out only if precursor ion is detected in full scan MS. List of precursor ions is necessary.

Non-target MS2 analysis. Fragmentation is carried out during entire chromatographic run. No precursor selection. No list of precursor ions is present.

70k 70k

FS/dd-MS2/AIF-MS2

17,5k

0.27 s 0.6 s 0.7 s

Combined target and non-target MS2 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.



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

LC Orbitrap Compound list

Target (166 compounds) Non-target (102 compounds) ddMS2 AIF-MS2



Pyridaben (target compound) 0.1 mg/kg in orange

FS/dd-MS2/AIF-MS2

Fragment ion detected in AIF-MS2

MS MS2

MS MS2

Fragment ions detected in Data dependent MS2



Isofenphos methyl (target compound) 0.1 mg/kg in orange

Fragment ion detected in AIF-MS2

MS MS2

MS MS2

Data dependent MS2 failure

MS2 scan not triggered

FS/dd-MS2/AIF-MS2



0%

10%

20%

30%

40%

50%

60%

70%

80%

90%

100%

0.01 mg/kg 0.02 mg/kg 0.05 mg/kg

Full scan

Full scan + 1 MS2fragment

Full scan + 2 MS2fragments

0%

10%

20%

30%

40%

50%

60%

70%

80%

90%

100%

0.01 mg/kg 0.02 mg/kg 0.05 mg/kg

Full scan



0%

10%

20%

30%

40%

50%

60%

70%

80%

90%

100%

0.01 mg/kg 0.02 mg/kg 0.05 mg/kg

Full scan



Tomato Lettuce

Zucchini

Number of spiked pesticides102

DETECTION OF NON-TARGET PESTICIDES



Number of spiked pesticides102

0%10%20%30%40%50%60%70%80%90%

100%

0.01 mg/kg 0.02 mg/kg 0.05 mg/kg

Full scan



Orange

0%10%20%30%40%50%60%70%80%90%

100%

0.01 mg/kg 0.02 mg/kg 0.05 mg/kg

Full scan



Leek





Imazapyr in pear (not included in EU Monitoring Program) (mass of protonated molecule 262.1186)

RT: 0.00 - 12.11

0 1 2 3 4 5 6 7 8 9 10 11Time (min)

0

50

1000

50

1000

50

100

Re

lative

Ab

un

da

nce 0

50

1004.73

4.74

4.74

4.74

Full scan MS

AIF MS2

AIF MS2

AIF MS2

262.1186 ± 5ppm

149.0345 ± 5ppm

174.0662 ± 5ppm

202.0611 ± 5ppm



MILLING

SAMPLE EXTRACTION

LC-HRAMS

GC-HRAMS EVALUATION

REPORT



IDENTIFICATION QUANTITATION

Target Analysis

• Retention time • Analytical standard

• 2 ions (<5

ppm)

• Recoveries • Linearity • Reproducibilty • Repeativity • Limit of quantitation

Quantitative validation




Target Analysis


• 2 ions



Non Target

Analysis (low

frequent com.)


• 1-2 ions(<5

ppm)

Single point calibration • Reproducibilty • Repeativity • Limit of detection/ quantitation

Qualitative or Semi quantitative validation




Target Análysis


• 2 ions



Non Target

Analysis (low

frequent comp.)


• 1-2 ions

• Single point calibration

• Reproducibilty • Repeativity • Limit of detection/ quantitation

Qualitative or Semi quantitative validation

• 2 -3 ions(<5

ppm)

• no analytical

standard , Rt?

Informative




Thank You for Your Attention

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