UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

OFFICE OF CHEMICAL SAFETY 

AND POLLUTION PREVENTION 

MEMORANDUM 

Date 

Subject: 

From: 

Through: 

To: 

21 -November-2013 

Metaflumizone in/on Imported Tomato, Pepper, and Eggplant. Summary of 

Analytical Chemistry and Residue Data. 

PC Codes: 281250 DP Barcode: 0412301,0414852 

Decision No.: 474810 Re2istration No.: none 

Petition No.: 3E8146 Regulatory Action: tolerances with no U.S. registration 

Risk Assessment Type: not applicable Case No.: 7446 

TXR No.: not applicable CAS No.: 139968-49-3 

MRID Nos.: see below 40 CFR: § 180.657 

Tom 

Risk Assessment 

Bloem, ChernBranch ~~ 1/Health Effects Division (RABl!HED; 7509P) 

John Herbert/Julie Chao RM 07 

Registration Division (RD; 7505P) 

Summary of Submitted/Reviewed Residue Chemistry Studies 

OCSPP 860 MRlDNumber Title Series Guideline 

860.1500 49196001 Determination of residues ofmetaflumizone 20% SC in red pepper. BASF DoclD 2007/1062861 

Study on the residue behavior of BAS 320 I on sweet pepper after application of BAS 320 00 I 

860.1500 49196002 under greenhouse conditions in Germany, the Netherlands, France, Italy and Spain, 2002. BASF 

DociD 2003/1001359 

Residue behavior of BAS 320 I after application of BAS 320 00 I on sweet pepper under 

860.1500 49196003 greenhouse conditions in the Netherlands France Italy Greece and Spain 2003. BASF DociD 

2004/5000468 

860.1500 49196004 Study on the residue behavior of BAS 320 1 after application of BAS 320 00 I on tomato under 

field conditions in Spain, 2003. BASF DociD 2004/1006476 

860.1500 49196005 Study on the residue behavior of BAS 320 I on tomato after application of BAS 320 00 I under 

field conditions in Italv and Spain, 2004. BASF DoclD 200411024762 

Study on the residue behavior of BAS 320 I in greenhouse tomatoes after application of BAS 320 

860.1500 49196006 00 I under field conditions in Germany, The Netherlands, France (North and South), Italy and 

Spain, 2002. BASF DociD 200411010549 

Study on the residue behavior ofBAS 320 I after application of BAS 320 00 I on tomato under 

860.1500 49196007 greenhouse conditions in The Netherlands, France, Greece and Spain, 2003. BASF DociD 

2004/5000469 

-- 49196008 Hydrolysis of 14C-BAS 320 I at 90°C, 100°C, and l20°C. BASF DociD 2002/5004262 

Page I of 19 
Metaflumizone Summary of Analytical Chemistry and Residue Data 0412301 

TABLE OF CONTENTS 

1.0 EXECUTNE SUMMARY .................................................................................................................... 3 

2.0 RECOMMENDATIONS ....................................................................................................................... 4 

2.1 Data Deficiencies/Data Needs ............................................................................................................. 4 

2.2 Tolerance Considerations .................................................................................................................... 4 

2.2.1 Enforcement Analytical Method ............................................................................................ 4 

2.2.2 Recommended Tolerances ..................................................................................................... 5 

2.2.3 Revisions to Petitioned-For Tolerances ................................................................................. 5 

2.2.4 International Harmonization ................................................................................................... 5 

2.3 Label Recommendations ..................................................................................................................... 5 

3.0 INTRODUCTION .................................................................................................................................. 6 

3.1 Chemical Identity ................................................................................................................................. 6 

3.2 PhysicaVChemical Properties .............................................................................................................. 7 

3.3 Pesticide Use Pattern/Directions .......................................................................................................... ? 

4.0 MET ABOLISMIDEGRADA TE RESIDUE PROFILE ......................................................................... 8 

5.0 RESIDUE PROFILE .............................................................................................................................. 9 

5.1 Residue Analytical Methods ................................................................................................................ 9 

5 .1. 1 Data Collection Methods ........................................................................................................ 9 

5 .1 .2 Multiresidue Methods ............................................................................................................ 9 

5.1.3 Tolerance-Enforcement Method ........................................................................................... 10 

5.2 Storage Stability ................................................................................................................................. 10 

5.3 Residue Data ...................................................................................................................................... 11 

5.3.1 Crop Field Trials .................................................................................................................. 11 

5.3.2 Field Rotational Crops ......................................................................................................... 12 

5.3.3 Processed Food/Feed ............................................................................................................ 12 

5.3.4 Meat, Milk, Poultry, and Eggs ............................................................................................. 13 

5.4 Food Residue Profile ......................................................................................................................... 13 

6.0 TOLERANCE DERIVATION ............................................................................................................ 13 

ATTACHMENT 1: INTERNATIONAL RESIDUE LIMITS ................................................................... 15 

ATTACHMENT 2: OECD TOLERANCE CALCULATIONS ................................................................ 16 

A IT ACHMENT 3. CHEMICAL NAMES AND STRUCTURES . .......................................................... 17 

ATTACHMENT 4: SUMMARY OF RESIDUE DATA ........................................................................... IS 

Page 2 of 19 
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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1.0 Executive Summary

Background: Metaflumizone (2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-

(trifluoromethoxy)phenyl]hydrazinecarboxamide; E:Z isomer ratio of >9:1) is a semicarbazone 

insecticide which blocks the voltage-dependent sodium channels of susceptible insects leading to 

paralysis. Metaflumizone is currently registered for application to citrus, tree nuts, and grapes with 

tolerances established at 0.04 ppm. Metaflumizone is also registered for application around 

industrial, commercial, agricultural, and recreational facilities/structures and premises. Application 

of metaflumizone to pets was previously registered but was cancelled by the registrant in 2011.

BASF requested tolerances for the combined residues of metaflumizone (E and Z isomers) and 

M320I04 in/on imported tomato, pepper, and eggplant at 0.6 ppm. In 2009, the annual Joint Food 

and Agricultural Organization/World Health Organization (FAO/WHO) Meeting on Pesticide

Residues (JMPR) reviewed data concerning the nature/magnitude of metaflumizone residues in/on 

crops. This review resulted in Codex establishing numerous maximum residue limits (MRLs) 

including the currently-established 0.6 ppm MRLs for the combined residues of metaflumizone (E 

and Z isomers) in/on tomato, pepper, and eggplant and a tolerance of 6 ppm for these same 

compounds in/on dried pepper. 

Since the current proposal is for tolerances in/on imported commodities, HED utilized the 2009 

JMPR metaflumizone report concerning the magnitude of the residues in/on tomato, pepper, and 

eggplant (DERs were not generated). Also utilized is a previous HED review concerning a 

registration proposal for application of metaflumizone to several crops grown in the U.S. including 

fruiting vegetables; it is noted that the proposed application to fruiting vegetables was never 

registered (D308394, T. Bloem, 30-Nov-2005; D304496, R. Mitkus et al., 24-Jan-2006). 

Proposed Use: The petitioner provided English translations of labels from the following countries 

(see Table 3.3.1): Indonesia, Korea, Italy, Austria, Macedonia, Germany, Mexico, Chile, and 

Columbia. The tomato, pepper, and/or eggplant application scenarios detailed in these labels are 

consistent with the use patterns summarized in the 2009 JMPR report for all countries excluding 

Macedonia and Mexico. The 2009 JMPR report did not include a summary concerning application 

of metaflumizone to tomato, pepper, and eggplant in Macedonia. For Mexico, the JMPR report 

indicates a maximum of two applications per season to tomato and bell pepper (0.29 kg ai/hectare) 

while the Mexican label provided to HED indicates the same application rate but does not provide a 

limit concerning the number per season (label does indicate that only two sequential applications 

may be made). 

Nature/Magnitude of the Residue - Livestock: There are no significant livestock feed commodities 

associated with the proposed crops. Therefore, a discussion concerning the nature/magnitude of the 

residue in livestock is unnecessary. 

Nature/Magnitude of the Residue - Rotational Crops: A discussion concerning the magnitude of the 

residue in rotational crops is not relevant to the current petition as tolerances on imported commodities 

are being requested. It is noted that the 2009 JMPR metaflumizone review indicated the following: 

“The data submitted on rotational crop metabolism suggest there are no residues of significance that 

are expected to arise in crops planted in the rotation following primary crop use of metaflumizone 

according to GAP.” In addition, the HED review concerning application to several crops including 

fruiting vegetable concluded that provided a 30-day PBI was established, tolerances in/on rotational 

crops would be unnecessary (D308394, T. Bloem, 30-Nov-2005; application rates of ≤1.0 lb ai/acre).
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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Nature of the Residue - Primary Crops: Based on previously submitted/reviewed cabbage (4 x 280

g ai/hectare), cotton (6 x 336 g ai/hectare), and tomato (6 x ~340 g ai/hectare) metabolism studies, 

HED concluded that the residues of concern in plants for tolerance enforcement and risk assessment

are metaflumizone (E and Z isomers) and M320I04 (D304496, R. Mitkus et al., 24-Jan-2006). HED 

requested additional information concerning the cabbage and cotton metabolism studies (D308394, T. 

Bloem, 30-Nov-2005); since the current request is for application to fruiting vegetables and since an 

adequate tomato metabolism study has been submitted, the requested data concerning the cabbage 

and cotton metabolism studies are not relevant to the current petition. 

Magnitude of the Residue - Proposed Crops: The number and geographical representation of the 

submitted field trial data are adequate. In addition, the petitioner submitted an adequate tomato 

processing study which indicated that the residues of concern concentrate in only tomato wet pomace, 

tomato peel, and tomato paste. All samples were analyzed using adequately validated methods and 

sufficient storage stability data are available. 

2.0 Recommendations

Provided the petitioner submits a revised Section and F, HED concludes that the residue chemistry 

database supports the establishment of permanent tolerances listed in Section 2.2.3. A human-health 

risk assessment is forthcoming. 

2.1 Data Deficiencies/Data Needs

There are no data deficiencies for the current petition. Although not relevant to the current petition, 

BASF has not responded to the following two previously identified data deficiencies (D345540, T. 

Bloem, 26-Jan-2010): 

–Cabbage metabolism study (46264326.der.wpd) - Information pertaining to sample extraction and 

analysis dates is required; if the interval from harvest to analysis is greater than the currently 

validated interval, then additional storage stability data will also be necessary. 

–Cotton metabolism study (46264324.der.wpd) - Individual concentrations of the unknowns should 

be reported; if any unknown comprises >10% of the total radioactive residue (TRR), then further 

characterization/ identification procedures may be required (based on these data, additional residues 

may be included for risk assessment). 

2.2 Tolerance Considerations

2.2.1 Enforcement Analytical Method

HED previously reviewed method validation and independent laboratory validation (ILV) studies for 

the BASF liquid chromatograph/mass spectrometer/mass spectrometer (LC/MS/MS) analytical 

method 531/0 and forwarded the method to FDA for tolerance enforcement (46264221.der; D308394, 

T. Bloem, 30-Nov-2005; D328915, T. Bloem, 17-May-2006). It is noted that following method 

validation, BASF incorporated several minor modifications to method 531/0 with this revised method 

specified as 531/1. Since the tomato, pepper, and eggplant magnitude of the residue samples 

submitted in support of the current petition, were analyzed using a method very similar to the current 

enforcement method and since adequate validation data were submitted, HED concludes that the 

current enforcement method is suitable for enforcement of the tolerances recommended herein. 

Analytical standards for of metaflumizone (E and Z isomers; expiration date 1-June-2021) and 

M320I04 (expiration date 1-July-2017) are currently available in the EPA National Pesticide 

Standards Repository (communication from Theresa Cole, BEAD, 5-Apr-2013).
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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2.2.2 Recommended Tolerances

Table 2.2.2.1 is a summary of the proposed and HED-recommended tolerances for the combined 

residues of metaflumizone (E and Z isomers) and M320I04 (expressed in parent equivalents). 

Table 2.2.2.1: Tolerance Summary.

Commodity Proposed 

Tolerance (ppm)1

HED-Recommended 

Tolerance (ppm)1 Comments

tomato 0.6 0.60 Based on the available field trial data and in order to harmonize with Codex, a 

tolerance of 0.60 ppm is recommended. 

tomato, paste -- 1.2 ppm

Based on the highest-average field-trial (HAFT) tomato residue and the average 

tomato paste processing factor of 2.94x, a tomato paste tolerance of 1.2 ppm is 

recommended (0.39 x 2.94 = 1.15). 

pepper 0.6 1.5 Based on the available data, residues in/on imported pepper and by translation 

eggplant may be greater than the proposed 0.6 ppm tolerance; using the pepper 

data and the Office of Economic Cooperation and Development (OECD)

tolerance-calculation procedure, a tolerance of 1.5 ppm is recommended. 

eggplant 0.6 1.5

2.2.3 Revisions to Petitioned-For Tolerances

Based on the HAFT tomato residue of 0.39 ppm and the average tomato paste processing factor of 

2.94x, a tomato paste tolerance of 1.2 ppm is recommended (0.39 x 2.94 = 1.15). Based on the available 

data, residues in/on imported pepper and by translation eggplant may be greater than 0.6 ppm; using the 

pepper data and the OECD tolerance-calculation procedure, a tolerance of 1.5 ppm is recommended

(pepper data translated to eggplant per 40 CFR 180.41 fruiting vegetable crop group 8-10). 

2.2.4 International Harmonization

HED concluded that the metaflumizone tolerance expression for crops should include metaflumizone 

(E and Z isomers) and M320I04. The Codex MRL expression differs in that it does not include 

M320I04 (see Attachment 1). HED included M320I04 as a residue of concern for risk assessment and 

tolerance enforcement purposes as it was identified at significant concentrations in the submitted 

metabolism study and is the primary residue in some processed commodities. 

Based on the available field trial data, HED concluded that harmonization with the currently 

established 0.6-ppm tomato Codex MRL was acceptable. However, based on the available field trial 

data, HED concluded that harmonization with the Codex pepper and eggplant MRLs was not 

appropriate (maximum residues in/on pepper of 0.66 ppm; pepper data translated to eggplant per 40 

CFR 180.41 fruiting vegetable crop group 8-10). In addition, HED concluded that based on the 

available data, a tomato paste tolerance should be established. 

HED notes that the currently established Codex MRLs are based on the 2009 Metaflumizone JMPR 

report and this report was utilized in the current review. The difference in the HED-recommended 

tolerances and the Codex MRLs may be due to the following issues: (1) codex MRLs do not include 

M320I04 residues; (2) the codex MRLs were established using the North American Free Trade 

Agreement (NAFTA) tolerance-calculation procedure which allowed the establishment of tolerances 

less than the highest residues; the OECD tolerance-calculation procedure, which was employed herein, 

does not permit this; and/or (3) the JMPR report indicated that only two applications were permitted to 

peppers grown in Mexico; based on the English translation of the Mexican labeled provided to HED, 

two sequential applications are permitted with no restriction on the number per season. 

2.3 Label Recommendations

Not relevant to the current petition as tolerances on imported commodities are being requested.
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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3.0 Introduction

3.1 Chemical Identity

The chemical structure and nomenclature of metaflumizone and its metabolites are presented in 

Tables 3.1.1. 

Table 3.1.1. Metaflumizone, M320I04, and M320I23 Nomenclature.

Chemical structure

Common name Metaflumizone

Company experimental name BAS 320 I

IUPAC name (EZ)-2'-[2-(4-cyanophenyl)-1-(α,α,α-trifluoro-m-tolyl)ethylidene]-4-

(trifluoromethoxy)carbanilohydrazide

CAS name 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-

(trifluoromethoxy)phenyl]hydrazinecarboxamide

CAS registry number 139968-49-3

Metabolite M320I04

4-[2-oxo-2-[3-(trifluoromethoxy)phenyl]ethyl]-benzonitrile

Metabolite M320I23

4-[5-hydroxy-3-oxo-4-[4-(trifluoromethoxy)phenyl]-6-[3-(trifluoromethyl)phenyl]-

2,3,4,5-tetrahydro-1,2,4-triazin-5-yl]benzonitrile

CN

N

N

H

N

H

O

O

F3C

CF3

CN

O

F3C

CN

N

F3C NH

N O

O

F3C

HO
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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3.2 Physical/Chemical Properties

Table 3.2.1 is a summary of the physical/chemical properties for metaflumizone. Metaflumizone 

has a low vapor pressure and a high Log Kow.

Table 3.2.1. Physicochemical Properties of Metaflumizone.

Melting points Two melting points observed at approximately 127 oC and 186 oC. MRID 46264204

pH 6.48 at 25 oC (1% aqueous suspension) MRID 46264524

Density (20 oC) 1.461 g/cm3 MRID 46264204

Water solubility (20 oC)

D.I. water 1.79 μg/L

pH 5 1.35 μg/L

pH 7 1.81 μg/L

pH 9 1.73 μg/L

MRID 46264208

Solvent solubility (20 oC)

Acetone 142.7 mg/L

Acetonitrile 60.3 mg/L

DCM 92.7 mg/L

EtOAc 159.7 mg/L

Heptane 0.0084 mg/L

Methanol 13.95 mg/L

Toluene 3.96 mg/L

MRID 46264212

Vapor pressure 1.24 x 10-8Pa at 20 oC MRID 46264206

Dissociation constant, pKa None in pH range 2-12 MRID 46264217

Octanol/water partition 

coefficient, Log(KOW)

Log POW = 5.1 (Z isomer)

Log POW = 4.4 (E isomer) MRID 46264213

UV/visible absorption 

spectrum

Molar absorptivity: 3.81×104 L/Mcm at 234 nm; 1.93×104

L/Mcm at 280 nm.

MRID 46264207

3.3 Pesticide Use Pattern/Directions

The petitioner provided English translations of labels from the following countries concerning 

application of metaflumizone to tomato, pepper, and/or eggplant (see Table 3.3.1): Indonesia, 

Korea, Italy, Austria, Macedonia, Germany, Mexico, Chile, and Columbia. The countries and 

application scenarios provided by the petitioner are consistent with the countries and application 

scenarios summarized in the 2009 JMPR metaflumizone report for all countries excluding 

Macedonia and Mexico (the JMPR report was utilized as part of the current review). The 2009 

JMPR review did not include a summary concerning application of metaflumizone to tomato, 

pepper, and eggplant grown in Macedonia. For Mexico, the JMPR review indicates a maximum 

of two applications per season to tomato and bell pepper while the Mexican label provided to 

HED indicates that only two sequential applications may be made but does not provide a limit 

concerning the number per season. 
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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Table 3.3.1. Summary of Application Scenarios

Crop Country Formulation

Application PHI

(days)

Comments Method Rate kg ai./ha RTI

(days)

Max no. of 

apps.

eggplant Italy SC 240 g ai/L foliar 0.24 7-10 2 x 0.24

3 x 0.06 3 field and greenhouse

pepper

Austria SC 240 g ai/L foliar

0.12 (<50 cm)

0.18 (50-125 cm)

0.24 (>125 cm)

7-14 2 1 greenhouse only

Germany SC 240g ai/L foliar

0.12 (<50 cm)

0.18 (50-125 cm)

0.24 (>125 cm)

7-14 2 3 greenhouse only

Macedonia SC 240g ai/L foliar 0.24 -- 4 3 --

pepper, sweet Italy SC 240 g ai/L foliar 0.24 7-10 2 3 greenhouse only

pepper, sweet (bell) Mexico SC 240 g ai/L foliar 0.29 4-7 --

2

3 --

pepper, chili Indonesia SC 240 g ai/L foliar 0.031 kg ai/hL1-- -- -- --

pepper, red (chili) Korea SC 20% (w:w) foliar 0.016 kg ai/hL1-- 3 2 --

Tomato

Austria SC 240 g ai/L foliar

0.12 (<50 cm)

0.18 (50-125 cm)

0.24 (>125 cm)

7-14 2 1 greenhouse only

Germany SC 240g ai/L foliar

0.12 (<50 cm)

0.18 (50-125 cm)

0.24 (>125 cm)

7-14 2 3 greenhouse only

Macedonia SC 240g ai/L foliar 0.24 -- 4 3 --

Italy SC 240 g ai/L foliar 0.24 7-10 2 3 field and greenhouse

Mexico SC 240 g ai/L foliar 0.29 4-7 --

2

3 --

Chile SC 240 g ai/L foliar 0.24 10-15 3 3 field and greenhouse

Columbia SC 240 g ai/L foliar 0.32 7 2 3 --

1

 The English translation of the Indonesian and Korean labels did not provided application rates in kg ai/ha. The Indonesian 

label indicated that the spray solution should contain 0.5 ml of the formulated product per liter (0.12 g ai/L) and high volumes 

sprays should be used. The Korean label indicated that the spray solution should contain 13 ml of the formulated product per 20 

L (0.16 g ai/L) and should be applied so as to ensure thorough coverage of foliage, bloom, and fruit. 

2

 The Mexican label indicates that no more than two sequential applications may be made but does not indicate a maximum 

number of applications per season. 

4.0 Metabolism/Degradate Residue Profile

Primary Crops: No plant metabolism studies were submitted with this petition. Cabbage (4 x 

280 g ai/hectare), cotton (6 x 336 g ai/hectare), and tomato (6 x ~340 g ai/hectare) metabolism 

studies have been previously submitted and reviewed. These studies were conducted with 

uniformly ring-labeled [benzonitrile14C]metaflumizone (B-label) and [trifluoromethoxyphenyl14C]metaflumizone (T-label). Identified residues accounted for 73-101% TRR in all 

commodities, excluding cottonseed, where total identified residues accounted for 56-64% TRR. 

The major identified residue in all commodities was metaflumizone (E and Z isomers; 34-98% 

TRR; E:Z ratio of ~1:1 to 12:1). M320I04 was a significant residue in all crops accounting for 

12-17% TRR. Residues of M320I06, M320I07, and M320I23 were also identified (≤8% TRR). 

Individual unknowns were <10% of the TRR in/on tomato and cabbage. For cotton, the studies 

presented only the following total unknown concentrations: cotton gin byproducts (13-16% 

TRR) and cottonseed (20-28% TRR). Based on these data, it appears that metaflumizone is 

metabolized in plants via isomerization of the metaflumizone E isomer to the Z isomer, ring 

formation to M320I23, cleavage of the parent molecule to form M320I04, cleavage of M320I23 

to form M320I05, and cleavage of M320I23 and/or M320I04 to form M320I06 (see Attachment 

3 for structures). 

Based on these data HED concluded that the residues of concern in plants for tolerance 

enforcement and risk assessment are metaflumizone (E and Z isomers) and M320I04 (D304496, 
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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R. Mitkus et al., 24-Jan-2006). HED requested additional information concerning the cabbage 

and cotton metabolism studies (D308394, T. Bloem, 30-Nov-2005); since the current request is 

for application to fruiting vegetables and since an adequate tomato metabolism study has been 

submitted, the requested data concerning the cabbage and cotton metabolism studies are not 

relevant to the current petition. 

Rotational Crops: A discussion concerning the nature of the residue in rotational crops is not 

relevant to the current petition as tolerances on imported commodities are being requested. 

Livestock: There are no significant livestock feed commodities associated with the proposed 

crops. Therefore, a discussion concerning the nature of the residues in livestock is unnecessary. 

5.0 Residue Profile

5.1 Residue Analytical Methods

5.1.1 Data Collection Methods 

Excluding the pepper trials conducted in Korea, the magnitude of the residue samples submitted in 

support of the current petition were analyzed for residues of metaflumizone (E and Z isomers), 

M320I04, and M320I23 using BASF Method 531/0 (see below for summary). This method is very 

similar to the current tolerance enforcement method; based on this and since adequate method 

validation data were submitted in conjunction with the magnitude of the residue data, HED 

concludes that this method is adequate for data collection purposes (residues in controls were 

<LOQ (limit of quantitation)).

The pepper samples from the Korean trials were extracted with acetone followed by a silica-gel 

column clean-up (MRID 49196001). The resulting extract was analyzed for residues of 

metaflumizone (E and Z isomers) and M320I04 using a GC/ECD (gas chromatograph/electron 

capture detector). The study indicated a detection limit of 0.01 ppm for both metaflumizone and 

M320I04. However, validation data were only provided at fortification levels of 0.1 ppm and 0.5 

ppm with recoveries of 87 ± 4% for metaflumizone and 104 ± 9% for M320I04. The study did not 

include a complete description of the analytical procedure, example chromatograms, or an example 

of the calculation procedure. Without this information, HED is not able to determine if the 

metabolite residues are expressed in parent equivalents. 

BASF Method 531/0: Briefly, residues are extracted using methanol:water (7:3; v:v) followed by a 

liquid/liquid partition against dichloromethane (DCM). The DCM phase is evaporated to dryness, 

redissolved in methanol:water, and analyzed via for HPLC/MS/MS (high-performance liquid 

chromatograph/mass spectrometer/mass spectrometer). Based on the lower limit of method 

validation, the LOQ for each analyte is 0.01 ppm (LOQ of 0.018 ppm and 0.01 ppm for M320I04 

and M320I23 when expressed in parent equivalents). 

5.1.2 Multiresidue Methods

Acceptable FDA multiresidue methods testing data have previously been submitted and 

indicated that these methods are not appropriate for quantifying metaflumizone residues. These 

data were forwarded to FDA (D323538, T. Bloem, 16-Nov-2005). 
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5.1.3 Tolerance-Enforcement Method

HED previously reviewed method validation and independent laboratory validation (ILV) studies 

for the BASF HPLC/MS/MS analytical method 531/0 and forwarded the method to FDA for 

tolerance enforcement (46264221.der; D308394, T. Bloem, 30-Nov-2005; D328915, T. Bloem, 

17-May-2006). It is noted that following method validation, BASF incorporated several minor 

modifications to method 531/0 with this revised method specified as 531/1 (method 531/1 is the 

current enforcement method). Since the tomato, pepper, and eggplant samples were analyzed 

using a method very similar to the current enforcement method and since adequate validation 

data were submitted, HED concludes that the current enforcement method is suitable for 

enforcement of the tomato, pepper, and eggplant tolerances recommended here. 

Analytical standards for metaflumizone (E and Z isomers; expiration date 1-June-2021) and 

M320I04 (expiration date 1-July-2017) are currently available in the EPA National Pesticide 

Standards Repository (communication from Theresa Cole, BEAD, 5-Apr-2013).

5.2 Storage Stability

HED previously reviewed frozen storage stability data for residues of metaflumizone (E- and Zisomers), M320I04, and M320I23 fortified in/on the following commodities (46264321.der,

46264322.der, 46264323.der, and 46264333.de2): cabbage, potato tuber, cottonseed, cotton gin 

byproducts, lettuce, tomato, tomato juice, tomato paste, and tomato peel. These data indicated 

that metaflumizone (Z isomer) and/or M320I04 are not stable in/on some of the proposed 

commodities. In some instances, it appears the metaflumizone Z isomer may be degrading to 

M320I04. Based on this information and to determine if residues in the field trail samples were 

behaving in a similar manner, a field-incurred storage stability study was conducted using the 

following commodities (46540413.der): cabbage, lettuce, celery, broccoli, mustard greens, and 

tomato. These data demonstrated that the combined residues of metaflumizone (E- and Zisomers), M320I04, and M320I23 were stable for the longest interval tested (371-449 days). It is 

noted that in lettuce, broccoli, and tomato residues of the metaflumizone Z-isomer declined with 

increasing storage interval while the concentration of M320I04 exhibited a corresponding 

increase. In addition, although the field-incurred storage stability study indicated that residues 

may also be degrading to M320I23 during storage, the magnitude of M320I23 residues at all 

storage intervals was insignificant compared to the combined residues of metaflumizone (E and

Z isomers) and M320I04. 

Excluding the pepper samples collected from the Korean field trials, the magnitude of the 

residues samples submitted in support of the current petitioner were stored frozen for ≤12 

months prior to analysis. HED concludes that the storage stability data summarized in the 

previous paragraph are adequate to validate this interval. The Korean pepper field trial study did 

not provide information concerning the sample storage interval.
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

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5.3 Residue Data

5.3.1 Crop Field Trials

2009 JMPR Metaflumizone Evaluation: 

http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Evaluation09/Metaflumizone.pdf

Since the current proposal is for tolerances in/on imported tomato, pepper, and eggplant, the 

magnitude of the residue summaries for the European Union (E.U.) field trails provided in the 

2009 JMPR report were utilized (DERs were not generated). In addition, HED previously 

reviewed a Section 3 registration proposal for application of metaflumizone to fruiting vegetables 

grown in the U.S. and the magnitude of the residue data form this review are also summarized 

herein (D308394, T. Bloem, 30-Nov-2005; D304496, R. Mitkus et al, 24-Jan-2006); it is noted 

that the proposed fruiting vegetable use was never registered. 

A summary of the E.U. and U.S. data can be found in Table 5.3.1.1 (see Attachment 4 for a 

summary of individual residues of the E and Z isomers and M320I04). The samples were analyzed 

using an appropriately validated method and the storage intervals for combined residues of 

metaflumizone (E and Z isomers) and M320I04 have been validated. It is noted that residues of 

M320I23 were also monitored but these data are not presented here (residues of ≤0.01 ppm; 

method and storage interval were validated). In general, combined residues of metaflumizone (E 

and Z isomers) and M320I04 declined with increasing PHI. 

Tomato and Pepper: Importation data attained from the United States Department of Agriculture 

(USDA) Economic Research Service (ERS) indicates that, based on mass, the bulk of the imported 

tomato and peppers are for the fresh market with the majority of these commodities coming from 

Mexico and Canada (http://www.ers.usda.gov/data-products/vegetables-and-pulses-data/bycommodity.aspx). Of these countries and based on the information in the 2009 JMPR report and 

provided by the petitioner, metaflumizone is registered for application to tomato and pepper in 

only Mexico. The English translation of the Mexican label indicates that metaflumizone may be 

applied to bell peppers and tomato at 0.29 kg ai/hectare with a 4- to 7-day retreatment interval and 

a 3-day PHI; the label indicates that no more than 2 sequential applications may be made but does 

not indicate a maximum number of applications per season. Since the residue-decline data 

indicated that, in general, residues decline with increasing PHI and since the label prohibits more 

than two sequential applications of metaflumizone, HED concludes that the application scenario 

and geographical representation of the tomato and pepper trials conducted in the U.S. are adequate 

to support the Mexican application scenario. No additional tomato or pepper field trial data are 

required for the proposed petition. A summary of HED conclusion concerning the appropriate 

tolerance can be found in Section 6.0. 

Eggplant: Importation data attained from the USDA ERS indicates that, based on mass, the bulk 

of the imported eggplant are for the fresh market with the majority of these commodities coming 

from Mexico and Honduras (http://www.ers.usda.gov/data-products/vegetables-and-pulsesdata/by-commodity.aspx). Based on the submitted labels, metaflumizone is only registered for 

application to eggplant in Italy. Eggplant residue data were not submitted; however, per 40 CFR 

180.41 fruiting vegetable crop group 8-10, the pepper residue data may be translated to eggplant. 

HED concludes that the application scenario and geographical representation of the pepper field 

trails conducted in the U.S. are adequate to support the Italian application sceario. No additional 

data field trial data are required for the proposed petition. A summary of HED conclusion 

concerning the appropriate tolerance can be found in Section 6.0. 
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 12 of 19

Table 5.3.1.1: Summary of Residue Data

Commodity/Country

MRID

App. Rate

(kg ai/hectare)

PHI 

(days) Analyte Residue Levels in Metaflumizone Equivalents (ppm)1

n Min. Max. LAFT2 HAFT2 Median Mean Std. Dev.

Bell Pepper/USA

46264332.der

4 x 0.28-0.30

(RTI = 6-8 days) 3 Combined3

7 0.05 0.66 0.05 0.55 0.33 0.32 0.17

Sweet Peppers/EU5

491960-02 and -03

2 x 0.26

(RTI = 6-7 days)

0 Combined3 10 0.11 0.83 -- -- 0.27 0.31 0.20

3-4 Combined310 0.09 0.63 -- -- 0.21 0.24 0.14

Sweet Peppers/EU5

491960-02 and -03

2 x 0.22

(RTI = 6-7 days)

0 Combined310 0.08 0.57 -- -- 0.29 0.28 0.13

3-4 Combined310 0.09 0.37 -- -- 0.19 0.22 0.10

Non-Bell Pepper/USA

46264332.der

4 x ~0.26

(RTI = 6-8 days) 3 Combined3

4 0.11 0.58 0.12 0.57 0.22 0.28 0.20

Pepper/Korea4,5

49196001

2 x 0.4

(RTI = 7 days) 1 Combined3

1 0.17 0.21 -- -- -- 0.19 --

Pepper/Korea4,5

49196001

3 x 0.4

(RTI = 7 days) 1 Combined3

1 0.20 0.24 -- -- -- 0.22 --

Tomato/USA

46264332.der

4 x 0.28-0.30

(RTI = 6-8 days) 3-4 Combined3

12 0.04 0.39 0.06 0.35 0.23 0.21 0.10

Tomato/EU5

491960-04 through -07

2 x 0.24-0.26

(RTI = 6-7 days)

0 Combined315 0.05 0.36 -- -- 0.13 0.14 0.08

2-3 Combined311 0.04 0.21 -- -- 0.10 0.11 0.05

Tomato/EU5

491960-04 through -07

2 x 0.22

(RTI = 6-7 days)

0 Combined315 0.04 0.40 -- -- 0.11 0.13 0.10

2-3 Combined311 0.04 0.25 -- -- 0.10 0.10 0.06

1

 LOQ residues were assumed for residues reported as <LOQ (LOQ = 0.01 ppm for metaflumizone E and Z isomers and 0.018 

ppm for M320I04). Storage stability data indicate that combined residues of metaflumizone (E and Z isomers) and M320I04 are 

stable in/on tomato (by inference peppers) for the interval from harvest to analysis (degradation of the metaflumizone Z isomer to 

M320I04 was noted). 

2

 LAFT = lowest-average field-trial; HAFT = highest-average field-trial. Only a single samples is collected form the EU trials; 

therefore, LAFT and HAFT are not applicable. 

3

 Combined metaflumizone (E and Z isomers) and M320I04 residues. 

4

 Study did not specify if a bell or non bell pepper was used. HED was also unable to determine if the metabolite residues are 

expressed in parent equivalents. 

5

 Since the current proposal is for tolerances in/on imported tomato, pepper, and eggplant, the 2009 JMPR metaflumizone 

magnitude of the residue summaries were utilized for the residue trials conducted in the EU and Korea (DERs were not 

generated). 

5.3.2 Field Rotational Crops

A discussion concerning the magnitude of the residue in rotational crops is not relevant to the 

current petition as tolerances on imported commodities are being requested. It is noted that the 

2009 JMPR metaflumizone review indicated the following: “The data submitted on rotational 

crop metabolism suggest there are no residues of significance that are expected to arise in crops 

planted in the rotation following primary crop use of metaflumizone according to GAP.” In 

addition, the HED review concerning application to several crops including fruiting vegetable 

concluded that provided a 30-day PBI was established, tolerances in/on rotational crops would be 

unnecessary (D308394, T. Bloem, 30-Nov-2005; maximum seasonal rate of ≤1.0 lb ai/acre).

5.3.3 Processed Food/Feed

The petitioner previously submitted an adequate tomato processing study (46264333.der); the 

results of this study are summarized in Table 5.3.3.1 (2009 metaflumizone JMPR report 

referenced this same study). Based on the 2009JMPR report, the currently established Codex 

MRL in/on dried chili pepper (6 ppm) is based on a default dehydration factor of 10 (EPA does 

not require tolerances in/on dried pepper). 

The 2009 JMPR report also included a summary of a study concerning the nature of metaflumizone 

residues under simulated processing conditions (MRID 49196008); hydrolyses of benzonitrile ring-U-
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 13 of 19

[

14C]metaflumizone and trifluromethoxyphenyl ring-U-[14C]metaflumizone were conducted at 90 °C in 

pH 4 aqueous buffer for 20 minutes (pasteurization simulation), at 100 °C in pH 5 aqueous buffer for 

60 minutes (baking, brewing, boiling simulation), and at 120 °C in pH 6 aqueous buffer for 20 minutes 

(sterilization simulation). Metaflumizone was not stable at pH 4 and pH 5 (90 °C–100 °C) with losses

as much as 40% (the hydrolysis products were M320I04 and M320I08).

Table 5.3.3.1: Summary of Processing Factors for Metaflumizone.

RAC Processed Commodity Combined Metaflumizone (E and Z isomers) and M320I04 Processing Factors

range average

Tomato

washed tomato 0.46-0.81x 0.66x

tomato juice 0.16-0.84x 0.51x

tomato wet pomace 1.59-12.55x 5.93x

peeled tomato 0.07-0.48x 0.27x

tomato peels 0.66-5.87x 2.13x

tomato puree 0.43-0.99x 0.70x

tomato paste 1.45-4.51x 2.94x

canned tomato 0.07-0.48x 0.36x

5.3.4 Meat, Milk, Poultry, and Eggs

There are no significant livestock feed commodities associated with the proposed crops. Therefore, a 

discussion concerning the magnitude of the residues in livestock is unnecessary. 

5.4 Food Residue Profile

Section 3 registrations for application of metaflumizone to citrus, tree nuts, and grape have been 

established (LOQ tolerances). As a result of these uses, dietary (food and water) exposure to 

metaflumizone is possible. The field trial data submitted with the current petition indicate that the 

major residue in/on the RACs is parent; however, the tomato processing study indicated that the major 

residue in/on the tomato processed commodities is M320I04. In addition, the Environmental Fate and 

Effects Division (EFED) concluded that metaflumizone has a high potential to bioaccumulate in 

aquatic food webs (D361157, K. Sappington, 21-Dec-2011). 

6.0 Tolerance Derivation

Table 6.0.1 is a summary of the petitioner proposed and HED recommended tolerances levels for the 

combined residues of metaflumizone (E and Z isomers) and M320I04 in/on imported tomato, pepper, 

and eggplant. The Codex MRL expression differs in that it does not include M320I04 (see Attachment 

1). HED determined that M320I04 should be included as a residue of concern for risk assessment and 

tolerance enforcement purposes as it was identified at significant concentrations in the submitted 

metabolism study and is the primary residue in some processed commodities. As indicated in Section 

5.3, the petitioner has submitted adequate field trial and processing studies conducted in the E.U. and 

U.S. to support the establishment of tolerances in/on the proposed imported commodities; no additional 

data are required. 

For tomato, the available EU and U.S. field trial data resulted in maximum combined residues of 

metaflumizone (E and Z isomers) and M320I04 of <0.60 ppm (See Table 5.3.1.1); therefore, HED 

concludes that harmonization with the currently established Codex MRL value is appropriate (tolerance 

expressions differ; see Attachment 1). However, based on the HAFT tomato residue of 0.39 ppm and the 

average tomato paste processing factor of 2.94x, a tomato paste tolerance of 1.2 ppm for the combined 

residues of metaflumizone (E and Z isomers) and M320I04 is recommended (0.39 x 2.94 = 1.15). 
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 14 of 19

For peppers, the maximum combined metaflumizone (E and Z isomers) and M320I04 residues in/on 

bell peppers from the U.S. trials were ≤0.66 ppm (4 x 0.29 kg ai/hectare; RTI = 6-8 days; PHI = 3 

days) and from the E.U. trials were ≤0.62 ppm (2 x 0.26 kg ai/hectare; RTI = 6-7 days; PHI = 3-4 

days). Therefore, HED concludes that harmonization with the Codex 0.6-ppm pepper MRL is not 

appropriate. Based on the U.S. pepper (bell and non-bell) data and the OECD tolerance-calculation 

procedure, a tolerance of 1.5 ppm for the combined residues of metaflumizone (E and Z isomers) and 

M320I04 is appropriate (see Attachment 2). HED used only the U.S. data to determine an 

appropriate pepper tolerance as the employed application scenario more closely matches the scenario 

registered in Mexico with Mexico having the highest registered application rate and is the major 

source of peppers imported into the U.S. HED notes that although Codex has established a MRL 

in/on dried pepper of 6.0 ppm, HED does not require tolerances in/on dried pepper. 

For eggplant and based on translation from the U.S. non-bell pepper field trail data (representative 

crop for eggplant; see 40 CFR 180.41 fruiting vegetable crop group 8-10), HED concludes that an 

eggplant tolerance of 1.5 ppm for the combined residues of metaflumizone (E and Z isomers) and 

M320I04 is appropriate (see Attachment 2). HED notes that, based on the information provided by 

the petitioner, application to eggplant is only registered in Italy with the seasonal application scenario 

employed in the U.S. trials being ~2x the registered seasonal Italian application rate (1x single 

application rate). Since the residue-decline data indicated that, in general, residues decline with 

increasing PHI, HED concludes that the U.S. data are sufficient. 

HED notes that the currently established Codex MRLs are based on the 2009 JMPR report for 

metaflumizone and this report was utilized in the current review. The differences in the HEDrecommended tolerances and the Codex MRLs may be due to the following issues: (1) codex MRLs 

do not include M320I04 residues; (2) the codex MRLs were established using the NAFTA tolerancecalculation procedure which allowed the establishment of tolerances less than the highest residues; 

the OECD tolerance-calculation procedure, which was employed herein, does not permit this; and/or 

(3) the JMPR report indicated that only two applications were permitted to peppers grown in Mexico; 

based on the English translation of the Mexican labeled provided to HED, two sequential applications 

are permitted with no restriction on the number per season. 

Table 6.0.1: Tolerance Summary.

Commodity Proposed 

Tolerance (ppm)1

HED-Recommended 

Tolerance (ppm)1 Comments

tomato 0.6 0.60 Based on the available field trial data and in order to harmonize with Codex, a 

tolerance of 0.60 ppm is recommended. 

tomato, paste -- 1.2 ppm

Based on the HAFT tomato residue of 0.39 ppm and the average tomato paste 

processing factor of 2.94x, a tomato paste tolerance of 1.2 ppm is 

recommended (0.39 x 2.94 = 1.15). 

pepper 0.6 1.5 Based on the available data, residues in/on imported pepper and by translation 

eggplant may be greater than 0.6 ppm. Based on the U.S. pepper data and the 

OECD tolerance-calculation procedure, a tolerance of 1.5 ppm is 

recommended. 

eggplant 0.6 1.5

RDI: RAB1 Chemists (4-Sep-2013)

Attachment 1: International Residue Limits.

Attachment 2: OECD Tolerance Calculations.

Attachment 3. Chemical Names and Structures.

Attachment 4: Summary of Residue Data.
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 15 of 19

Attachment 1: International Residue Limits. 

Summary of US and International Tolerances and Maximum Residue Limits 

Residue Definition

US Canada Mexico2 Codex

Combined residues of metaflumizone (E and Z isomers; 2-[2-(4-

cyanophenyl)-1-[3-(trifluoromethyl) phenyl]ethylidene]- N -[4-

(trifluoromethoxy)phenyl] hydrazinecarboxamide) and its metabolite 

4-{2-oxo-2-[3-(trifluoromethyl) phenyl]ethyl}-benzonitrile 

(calculated in parent equivalents)

None --

Plant and Animal 

commodities: 

metaflumizone, sum of 

metaflumizone E-isomer

and metaflumizone Zisomer. The residue is fatsoluble.

Tolerance/Maximum Residue Limit (ppm)

Commodity1 US Canada Mexico2 Codex

tomato 0.60 -- -- 0.6

tomato, paste 1.2 -- -- --

pepper 1.5 -- -- 0.6; 6 peppers, chili dried

eggplant 1.5 -- -- 0.6 

Completed: M. Negussie: 06/10/2013 

1

Includes only commodities of interest for this action. Tolerance values are HED recommendations and not those proposed by 

the applicant.

2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes.
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 16 of 19

Attachment 2: OECD Tolerance Calculations.

Compound

Crop

Region / Country

GAP

Total number of data (n)

Percentage of censored data

Number of non-censored data

Lowest residue

Highest residue

Median residue

Mean

Standard deviation (SD)

Correction factor for censoring (CF)

Proposed MRL estimate

- Highest residue

- Mean + 4 SD

- CF x 3 Mean

Unrounded MRL

Rounded MRL

Residues (mg/kg) Residues (mg/kg)

0.050 0.220

0.365 0.125

0.195 0.570

0.550 0.225

0.480

0.330

0.265

7

0%

metaflumizone

bell peppers

USA

4 x 0.26-0.29 kg ai/hectare

7

0.050

0.550

0.330

0.319

0.169

0.997

1

High uncertainty of MRL 

estimate due to small 

dataset.

1.000

0.550

0.997

0.958

0.125

0.570

0.223

0.285

0.195

1.000

0.570

1.067

0.855

1.067

1.5

High uncertainty of MRL 

estimate due to small 

dataset.

4

metaflumizone

non-bell pepper

USA

4 x 0.26-0.29 kg ai/hectare

4

0%
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 17 of 19

Attachment 3. Chemical Names and Structures.

Common name/code Chemical name Chemical structure

Metaflumizone E/Z isomer

(EZ)-2'-[2-(4-cyanophenyl)-1-(α,α,αtrifluoro-m-tolyl)ethylidene]-4-

(trifluoromethoxy)carbanilohydrazide

M320I04

4-[2-oxo-2-[3-

(trifluoromethoxy)phenyl]ethyl]-

benzonitrile

M320I05 -- H2N O

F

F

F

M320I06 4-cyanobenzoic acid

N

O

HO

M320I07 hydroxyl parent

N

N

NH NH

O

F

F F

O

F

F

F

HO

M320I08 --

O

F

F

F

H

N NH

NH2

O

M320I23

4-[5-hydroxy-3-oxo-4-[4-

(trifluoromethoxy)phenyl]-6-[3-

(trifluoromethyl)phenyl]-2,3,4,5-

tetrahydro-1,2,4-triazin-5-

yl]benzonitrile e

M320I28

(hydrolysis product of 

Metaflumizone)

N-[4-(trifluoromethoxy)phenyl]-

acetamide

CN

N

N

H

N

H

O

O

F3C

CF3

CN

O

F3C

CN

N

F3C NH

N O

O

F3C

HO

H C3

N

H

O

O

CF3
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 18 of 19

Attachment 4: Summary of Residue Data.

Summary of Residue Data from Crop Field Trials

Commodity/

Country

App. Rate

(lb ai/acre)

PHI 

(days) Analyte Residue Levels in Metaflumizone Equivalents (ppm)1

n Min. Max. LAFT2 HAFT2 Median Mean Std. Dev.

Bell Pepper/USA

46264332.der

4 x ~0.26

(RTI = 6-8 days) 3

Metaflumizone E isomer 7 0.01 0.23 0.01 0.20 0.09 0.11 0.07

Metaflumizone Z isomer 7 0.02 0.39 0.02 0.33 0.18 0.18 0.11

Metaflumizone E and Z isomers 7 0.03 0.62 0.03 0.52 0.31 0.30 0.17

M320I04 7 0.02 0.04 0.02 0.03 0.02 0.02 0.01

Combined37 0.05 0.66 0.05 0.55 0.33 0.32 0.17

Sweet Peppers/EU5

greenhouse/field

MRIDs 491960-02 

and -03

2 x 0.26

(RTI = 6-7 days)

0

Metaflumizone E isomer 10 0.07 0.39 -- -- 0.18 0.19 0.09

Metaflumizone Z isomer 10 0.02 0.42 -- -- 0.05 0.10 0.12

Metaflumizone E and Z isomers 10 0.09 0.81 -- -- 0.25 0.30 0.20

M320I04 10 0.02 0.02 -- -- 0.02 0.02 --

Combined310 0.11 0.83 -- -- 0.27 0.31 0.20

3-4

Metaflumizone E isomer 10 0.05 0.18 -- -- 0.11 0.12 0.04

Metaflumizone Z isomer 10 0.02 0.43 -- -- 0.06 0.11 0.12

Metaflumizone E and Z isomers 10 0.07 0.61 -- -- 0.20 0.22 0.14

M320I04 10 0.02 0.02 -- -- 0.02 0.02 --

Combined310 0.09 0.63 -- -- 0.21 0.24 0.14

Sweet Peppers/EU5

greenhouse/field 

MRIDs 491960-02 

and -03

2 x 0.22

(RTI = 6-7 days)

0

Metaflumizone E isomer 10 0.05 0.26 -- -- 0.16 0.17 0.06

Metaflumizone Z isomer 10 0.01 0.29 -- -- 0.07 0.09 0.08

Metaflumizone E and Z isomers 10 0.06 0.55 -- -- 0.27 0.26 0.13

M320I04 10 0.02 0.02 -- -- 0.02 0.02 --

Combined310 0.08 0.57 -- -- 0.29 0.28 0.13

3-4

Metaflumizone E isomer 10 0.04 0.15 -- -- 0.12 0.10 0.04

Metaflumizone Z isomer 10 0.02 0.24 -- -- 0.06 0.10 0.08

Metaflumizone E and Z isomers 10 0.07 0.35 -- -- 0.18 0.20 0.10

M320I04 10 0.02 0.02 -- -- 0.02 0.02 --

Combined310 0.09 0.37 -- -- 0.19 0.22 0.10

Non-Bell Pepper/USA

46264332.der

4 x ~0.26

(RTI = 6-8 days) 3

Metaflumizone E isomer 4 0.02 0.16 0.03 0.16 0.08 0.09 0.05

Metaflumizone Z isomer 4 0.07 0.40 0.08 0.39 0.12 0.18 0.14

Metaflumizone E and Z isomers 4 0.09 0.56 0.11 0.55 0.20 0.26 0.19

M320I04 4 0.02 0.03 0.02 0.03 0.02 0.02 0.004

Combined34 0.11 0.58 0.12 0.57 0.22 0.28 0.20

Pepper/Korea4,5

MRID 49196001

2 x 0.4

(RTI = 7 days) 1

Metaflumizone E and Z isomers 1 0.13 0.16 -- -- -- 0.14 --

M320I04 1 0.04 0.05 -- -- -- 0.05 --

Combined31 0.17 0.21 -- -- -- 0.19 --

Pepper/Korea4,5

MRID 49196001

3 x 0.4

(RTI = 7 days) 1

Metaflumizone E and Z isomers 1 0.15 0.17 -- -- -- 0.16 --

M320I04 1 0.05 0.08 -- -- -- 0.06 --

Combined31 0.20 0.24 -- -- -- 0.22 --
Metaflumizone Summary of Analytical Chemistry and Residue Data D412301

Page 19 of 19

Summary of Residue Data from Crop Field Trials

Commodity/

Country

App. Rate

(lb ai/acre)

PHI 

(days) Analyte Residue Levels in Metaflumizone Equivalents (ppm)1

n Min. Max. LAFT2 HAFT2 Median Mean Std. Dev.

Tomato/USA

46264332.der

4 x ~0.26

(RTI = 6-8 days) 3/4

Metaflumizone E isomer 12 0.01 0.11 0.02 0.10 0.07 0.06 0.03

Metaflumizone Z isomer 12 0.01 0.21 0.02 0.18 0.11 0.11 0.06

Metaflumizone E and Z isomers 12 0.02 0.32 0.04 0.28 0.17 0.17 0.08

M320I04 12 0.02 0.09 0.02 0.09 0.04 0.04 0.02

Combined312 0.04 0.39 0.06 0.35 0.23 0.21 0.10

Tomato/EU5

greenhouse/field

MRIDs 491960-04 

through -07

2 x 0.24-0.26

(RTI = 6-7 days)

0

Metaflumizone E isomer 15 0.01 0.25 -- -- 0.06 0.08 0.06

Metaflumizone Z isomer 15 0.01 0.10 -- -- 0.05 0.05 0.02

Metaflumizone E and Z isomers 15 0.03 0.34 -- -- 0.11 0.13 0.08

M320I04 15 0.02 0.02 -- -- 0.02 0.02 --

combined 15 0.05 0.36 -- -- 0.13 0.14 0.08

2-3

Metaflumizone E isomer 11 0.01 0.12 -- -- 0.04 0.04 0.03

Metaflumizone Z isomer 11 0.01 0.09 -- -- 0.05 0.05 0.02

Metaflumizone E and Z isomers 11 0.02 0.19 -- -- 0.08 0.09 0.05

M320I04 11 0.02 0.02 -- -- 0.02 0.02 --

Combined311 0.04 0.21 -- -- 0.10 0.11 0.05

Tomato/EU5

greenhouse/field 

MRIDs 491960-04 

through -07

2 x 0.22

(RTI = 6-7 days)

0

Metaflumizone E isomer 15 0.01 0.28 -- -- 0.05 0.07 0.08

Metaflumizone Z isomer 15 0.01 0.10 -- -- 0.04 0.04 0.02

Metaflumizone E and Z isomers 15 0.02 0.38 -- -- 0.09 0.11 0.10

M320I04 15 0.02 0.02 -- -- 0.02 0.02 --

Combined315 0.04 0.40 -- -- 0.11 0.13 0.10

2-3

Metaflumizone E isomer 11 0.01 0.13 -- -- 0.03 0.04 0.04

Metaflumizone Z isomer 11 0.01 0.10 -- -- 0.04 0.04 0.03

Metaflumizone E and Z isomers 11 0.02 0.23 -- -- 0.08 0.08 0.06

M320I04 11 0.02 0.02 -- -- 0.02 0.02 --

Combined311 0.04 0.25 -- -- 0.10 0.10 0.06

1

 LOQ residues were assumed for residues reported as <LOQ (LOQ = 0.01 ppm for metaflumizone E and Z isomers and 0.018 ppm for M320I04). Storage stability data indicate 

that combined residues of metaflumizone (E and Z isomers) and M320I04 are stable in/on tomato (by inference peppers) for the interval from harvest to analysis (degradation of 

the metaflumizone Z isomer to M320I04 was noted). 

2

 LAFT = lowest-average field-trial; HAFT = highest-average field-trial. Only a single samples is collected form the EU trials; therefore, LAFT and HAFT are not applicable. 

3

 Combined metaflumizone (E and Z isomers) and M320I04 residues. 

4

 Study did not specify if a bell or non bell pepper was used. HED was also unable to determine if the metabolite residues are expressed in parent equivalents. 

5

 Since the current proposal is for tolerances in/on imported tomato, pepper, and eggplant, the 2009 JMPR metaflumizone magnitude of the residue summaries were utilized for 

the residue trials conducted in the EU (DERs were not generated).