### UNITED STATES E NVIR O NMENTAL PROTECTION AGENCY WASHINGTON, D.C. 20460

OFFICE OF CHEMICAL SAFETY
AND POL L UTION PREVENTION



### MEMORANDUM

Date

Subject:

From :

Through:

To : 21 -N ovember-2013

Metaflumizone in/on Imported Toma to, Pepper, and Eggplant. Summary of Analytical Chemistry and Residue Data

.

PC Code s : 281250 DP Barcode: 0412301,0414852
Decision No.: 474810 Re2istration No

. : none Pe tition No.: 3E8146 Regulatory Action: tolerances with no U.S. registration

Risk A ss es sment Type: not applicable Case No. : 7446

TXR No

. : not applicable CAS No

. : 13996 8

- 49

- 3

MRID Nos.: see below 40 CFR: § 180.657



### Tom Bloem

,

# Chern**~~** Risk Assessment Branch 1/Health Effe ct s Division (RABl!HED; 7509P)

John Herbert/Julie Chao RM 07 Regi s tration Divi s ion (RD; 7505P)

Summary of Submitted/Reviewed Residue Chem istry Studies

OCSPP 860 MRlDNumber T i tle Series Guideline

860.1500 49196001 Determinat ion 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 o f B AS 320 00 I

860.1500 49196002 under greenhouse cond itions in Germany, the Netherlands, France, Italy and Spain, 2002

. BASF

DociD 2003 / 1 001359

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

860

. 15 00 49196003 greenhouse conditions in the Netherlands France Italy Greece and Spain 2003

. BASF DociD

2004/5000468

860 .15 00 49 196004 Study on the residue behav ior o f BAS 320 1 after application o f BAS 320 00 I on tomato under

field conditions in Spain, 2003. BASF DociD 2004 /1 006476

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

fie ld conditions in Italv and Spain, 2004. BASF DoclD 200411024762 Study on the residue be h avi or of BAS 320 I in greenhouse tomatoes after application of BAS 320

860.1500 49 1 96006 00 I under field conditions in Germany, The Netherlands, F rance (North and South), Italy and Spain, 2002. B ASF D ociD 200411010549 Study on the residue beha v ior ofBAS 320 I after application of BA S 320 00 I on tomato under

86 0.1500 4919 6007 greenh ous e condit ions in The Netherlands, France

, Greece and Spain

, 2003. BASF DociD

2004 /5000 469



# -- 49196008 Hydrolysi s of 14C

- BAS 320 I at 90°C, 1 00°C, and l20°C

. BASF DociD 2002/5004262

Page I of 19Metaflumizone Summary o f Analytica l Chemistry and Res i due Data 0412301



### TABLE OF CONTENTS



### 1

. 0 EXECUTNE SUMMARY

. .. ... .. ... . ... .. .. ... .. .. ... . ... .. .. .. . . . .. .. . . . . .. .. .. . . .... ... .......... .. . . . . .. .. . .. ......... ... . ....... . ....... 3

2.0 RECOMMENDATIONS

... ............. . .. . ............................... . . .. .... . .. .. ... . .. .. .. .. .. .. .. .. .. .. ... .. . .. .. .. .. .. . ... . .. . ... . .. . 4

2

. 1 Data Deficiencies/Data Needs

.................. . .............. . .. .. . . ... .. ... . .... . .. .. .. .. ... . .. .. . . . . .. .. ... . . . .. .. . ...... . . . ........... 4

2

. 2 To l erance 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 In t erna t i onal Harmonization

........ . . . ...... . ............................................... . . .. ... . . .. .. . .... . .. .. .. . ... . .. .. 5

2.3 Label Recommendations

........... . .. .. .. . ........ .. .. .. ... . ... .. .. .. ... . ... .. .. . .... . ...... . ........ . ...................................... 5

3.0 INTRODUCTION

.......................... . ........ . ......... .. .. . ....... ... .. . ... . ... . .. ... ....... . ... . ... . ... . .. . ............................... 6

3

. 1 Chemical Ident i ty

........ . .... .. .. .. .. ... . . .. .. .. ... .. ... . .. . .. . . . . . ............................ . . . .... . .. .. ... . .. ... . ... . .. ..... ... . ... . .. . .. .. .. 6
3.2 PhysicaVC h emica l Properties

.. ... . ... . ............................................. .. ... . ...... . ....... .. .. . ... . ... . .. .. .. . ............... 7

3

. 3 Pesticide Use Pattern/Directions

...................... . .. . ... .. .. .. ... . . . . .. .. .. .. .. ... . .. .. .. . .... .. ....... . ............................ . ?

4

. 0 MET ABOLISMIDEGRADA TE RESIDUE PROFILE

. ..... . ....... .. ............... . ..... . . . . .. . .. .. . .. .. .. .. .. . .. ... . ....... 8

5

. 0 RESIDUE PROFILE

... . ... ... . ... . .............................. .. . ... .. .. .. .. ... .. .. .. .. .. ...... . ... .. . . . . ............................. . . . . .... . 9

5

. 1 Residue Ana l ytical Methods

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

. .......... . ... . ................................ . ... .. .. .. ... . .. .. ... . ...... . ........................ ... 9

5 .1

. 2 Mu l t i residue Methods

. ... ... ............ . ......................................... . .. .. ... . ... . ..... ... ..... . .................... 9

5.1.3 Tolerance

- Enfo r cement Method

.... . . . . . .. . .............................................. . . . .. ... . .. . .... . . . .............. 1 0



### 5.2 Storage Stabi li ty

.. .. ... .. .. .. ... .......................... . .......... . .... .. ... . .. .. ... . ... .. ....... . .......... .. ......................... .. . .. .. 10

5.3 Res i due Data

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

. ............ . .............................. . . . .... .. .. .. ... . ... .. .. .. .. . ......................................... 11



### 5.3.2 F i eld Rotational Crops

.. . ................................ . ...... .. ... . ... . ... . ... .. ..... . . . ... . ............................... . 12



### 5.3.3 Processed Food/Feed

. . .............................. . .... . ... . ... . .... . ...... . ... . ............... . ............. . .... . ... .. .. .. . . 12



### 5.3.4 Meat, Mi l k, Po u ltry, and Eggs

............ . ........ . ... . ............. . ... .. .. . ... . .. . ... .. ........................... . .... . 13



### 5.4 Food Residue Profile

.......... ...... ......... . ... . ... . ... . ... .. .. .. ... .. . . .. ... . ...... . ............................ .. .. ... .. .. .. . ... .. . .. .. . . 13

6.0 T OLERANCE DERIVATION

. . . . ............................ . ..... . . .... . .. ... . ... . ... .. . . ..... . ............................. . . . . ....... 1 3

ATTACHMENT 1: IN T ERNATIONAL RESIDUE LIMITS

..................... . ....... . .... . ... . .. .. .. .. . . ... . .............. 15

ATTACHMENT 2: OECD TOLERANCE CALCULATIONS

... ... .. . ... ...... . ....................... .. .. . ...... .. .. . .. .. . . 16

A 

### IT ACHMENT 3. CHEMICAL NAMES AND STRUCTURES

. . . .. ...... . . .. .. ... . .. ... . .. . ... . ... . .. . .................. 1 7

ATTACHMENT 4: SUMMARY OF RESIDUE DATA

. . . ................. . ................ .. .. . ... . ... . ............ . ............ IS

Page 2 of 19Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 3 of 19 

### 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 channel s of susceptible insects leading to paralysis

. Metaflumizone is currently reg istered for application to c itrus, t ree n uts, and g rape s with tolerances established at 0.04 ppm. Metaflumizone is also registered for application around

i ndustrial, c ommercial, a gricultural

, and r ecreational f acilities/ s tructures and p remises

. Ap plication
of metaflumizone to pets was previously registered but was cancelled by the registrant in 201 1

. BASF requested tolerance s 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 H ealth Organization ( FAO/WHO ) Meeting on Pesticide Residues (JMPR) reviewed data concerning the nature/magnitude of metaflumizone residues in/on

cr o ps . T his review result ed 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 import ed commodities, HED utilized th e 2009

JMPR metaflumizone report concerning the magnitude of the residues in/on tomato, pepper, and eggplant (DERs were not generated). Also uti lized is a previous HED review concerning a registration proposal for a pplication of metaflumizone to several crops grown in the U.S. including

f ruiting vegetables ; it is noted that the proposed application to fruiting vegetables was never registered (D308 394, 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, Chil e , and Columbia. The tomato, pepper, and/or eggplant application scenarios detailed in the se labels are consistent with the use patterns summarized in the 2009 JMPR re port for all countries excluding
Macedonia and Mexico. The 2009 JMPR re port did not include a summary concerning application
of metaflumizone to tomato , pepper, and eggplant in Macedonia. For Mexico, the JMPR re port 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 signifi cant 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 mag nitude 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 in cluding 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 D 412301

P age 4 of 19 

### Nature of the Residue

- P rimary Crops : Based on previously submitted/reviewed c abbage (4 x 280

g ai/ hectare ) , cotton ( 6 x 336 g ai/hectare ) , and tomato (6 x

~ 3 40 g ai/hectare ) metabolism studies,
HED conclude d that t he 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); sin ce 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.

Magnitud

e 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 concentra te 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

- hea lth
risk assessment is forth coming.

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 (462 64326.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 the se 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 spectromet er ( 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 followin g method validation, BASF incorporated several minor modifications to method 531/0 with this revised method specified as 531/1. Since the tomat o, pepper, and eggplant magnitude of the residue samples submitted in support of the current petition, were anal yzed 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 here in

. Analytical standard s 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 D 412301

P age 5 of 19 

### 2.2.2 Recommend ed Tolerances

Table 2.2.2.1 is a summary of the proposed and HED

- recommended tolerance s 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 proced ure , 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. T he 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 wit h 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 th is report was utilized in the current review. T he 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 Am erican Free Trade Agreement ( NAFT A) tolerance

- calculation procedure which allowed the establishment of tolerances less than the highest residues; the OECD tolerance

- calculation procedure , which was employed here in

, 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

N ot relevant to the current petition as tolerances on imported commodities are being requested.Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 6 of 19 

### 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]benzonitrileMetaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 7 of 19 

### 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 K
ow 

### .

Table 3. 2 .1

. Physicochemical Properties of Metaflumizone.

Melting point s Two melting points observed at approximately 127 o C and 186 o C

. MRID 46264204

pH 6.48 at 25 o C (1% aqueous suspension) MRID 46264524
Density (20 oC) 1.461 g/cm 3 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

He ptane 0.0084 mg/L
Methanol 13.95 mg/L
Toluene 3.96 mg/L MRID 46264212

Vapor pressure 1.24 x 10 - 8 Pa at 20 o C MRID 46264206
Dissociation constant, pK

a None in pH range 2

- 12 MRID 46264217
Octanol/water partition coefficient, Log(K OW ) Log P OW = 5.1 ( Z isomer) Log P OW = 4.4 (E isomer) MRID 46264213

UV/visible absorption
spectrum Molar absorptivity: 3 .8 1×10 4 L/Mcm at 234 nm; 1

. 93×10 4

L/Mcm at 280 nm

. MRID 462 6 42 07



### 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, Chil e , and Columbia. The countries and application scenarios provided by the petitioner are consistent with the countries and application
scenarios s ummarized in the 2009 JMPR metaflum izone re port 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 Mac edonia. 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 th e number per season.Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 8 of 19 Table 3.3.1. Summary of Application Scenarios

Crop Country Formulation Application PHI ( days ) Comments Method Rate kg a i ./ha R TI (days) M ax no. of

apps.

eggplant Italy SC 240 g ai/L foliar 0.2 4 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/hL 1

-- -- -- -- pepper, red (chili) Korea SC 20% (w:w) foliar 0.016 kg ai/hL 1

-- 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

P rimary Crops : No plant metabolism studies were submitted with this petition. C abbage (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 pre viously submitted and reviewed . T hese studies were conducted with uniformly ring

- labeled [benzonitrile

14 

### C]metaflumizone (B

- label) and [trifluoromethoxyphenyl

14 

### C]metaflumizone (T

- label). Identified residues accounted for 73

- 101% TRR in all commodities, excluding cottonseed, where total identified residues accounte d 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 M32 0I23 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). B ased 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 conclude d that t he 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 D 412301

P age 9 of 1 9 

### R. Mitkus et al. , 24

- Jan

- 2006)

. HED requested additional information concerning the cabbage
and cotton metabolism studies (D 308394, T. Bloem, 30

- Nov

- 2005 ) ; since the current request is for application to fruiting vegetable s and since an adequate tomato metabolism study has been submitted, the requested data concerning the cabbage and cotton metabolism studies are not

r elevant 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, t he 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 M ethod 531/0 (see below for summary)

. This method is very
similar to the current t olerance 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 (r esidues in controls were

<L OQ (limit of quantitation) )

.

The pepper samples from the Korean trials were extracted wi th 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 8 7 ± 4% for metaflumizone and 10 4 ± 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 determin e 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

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

, redissol v ed 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).Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 10 of 19 

### 5.1.3 Tolerance

- Enforcement Method

HED previously reviewed method validation and independent laboratory validation (ILV) studies
for the BASF HP 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 (method 531/1 is the current enforcement method). Since the tomato, pepper, and e ggplant 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 eggplan t tolerances recommended here.

Analytical standards for metaflumizone (E and Z isomers; expiration date 1

- June

- 2021 ) and M320I04 ( expiration date 1

- July

- 201 7 ) are currently available in the EPA National Pesticide Standards Repository (communication from Theresa Cole, BEAD, 5

- Apr

- 201 3 ).

5.2 Storage Stability

HED previously reviewed frozen storage stability data for residues of metaflumizone (E

- and Z

isomers), M320I04, and M320I23 fortified in/on the following commodities (46264321.der, 46264322.der, 4 6264323.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

- in curred 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 Z

isomers), M320I0 4, 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 corre sponding
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 th is interval. The Korean pepper field trial study did not provide information concerning the sample storage interval.Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 11 of 19 

### 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 m agnitude of the residue data form this review are also summarized
here in (D308394, T. Bloem, 30

- Nov

- 2005; D304496, R. Mitkus et al , 24

- Jan

- 2006) ; it is noted
that th e proposed fruiting vegetable u se was never registered.

A summary of the E

. U

. and U.S. d ata 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
metaflumizon e (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 meta flumizone (E and Z isomers) and M320I04 declined with increasing PHI.

Tomato and Pepper: Importation data attained from the U nited States Department of Agriculture (U SDA ) 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

- product s/vegetables

- and

- pulses

- data/by

commodity.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 translat ion 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 d oes not indicate a maximum number of applications per season. Since the residue

- decline data
indicated that

, in general

, residue s decline with increasing PHI and since the label prohibits more than two sequential applications of metaflumizone, HED conclud es 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 th e imported eggplant are for the fresh market wit h the majority of these commodities coming
from Mexico and Honduras ( http://www.ers.usda.gov/data

- products/vegetables

- and

- pulses

data/by

- commodity.aspx ). Base d on the submitted labels , metaflumizone is only registered for application to eggplant in Italy. E ggplant 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

. H ED concludes that the application scenario and geographical representation of the pepper field
trail s conducted in the U.S. are adequate to support the Italian application sceario

. No additional data field trial data are required for the propo sed 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 D 412301

P age 12 of 19 T able 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. LAFT 2 HAFT 2 Median Mean Std. Dev.
Bell Pepper

/USA
46264332.der 4 x 0.28

- 0.30 (RTI = 6

- 8 days) 3 Combined 3 7 0.05 0.66 0.05 0.55 0.33 0.32 0.17

Sweet Peppers/EU 5

491960

- 02 and

- 03 2 x 0.26 (RTI = 6

- 7 days) 0 Combined 3 10 0.11 0.83

-- -- 0.27 0.31 0.20

3

- 4 Combined 3 10 0.09 0.63

-- -- 0.21 0.24 0.14 Sweet Peppers/EU 5

491960

- 02 and

- 03 2 x 0.22 (RTI = 6

- 7 days) 0 Combined 3 10 0.08 0.57

-- -- 0.29 0.28 0.13

3

- 4 Combined 3 10 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 Combined 3 4 0.11 0.58 0.12 0.57 0.22 0.28 0.20

Pepper/Korea 4,5

49196001 2 x 0.4 (RTI = 7 days) 1 Combined 3 1 0.17 0.21

-- -- -- 0.19

--
Pepper/Korea 4,5

49196001 3 x 0.4 (RTI = 7 days) 1 Combined 3 1 0.20 0.24

-- -- -- 0.22

--

Tomato/USA
46264332.der 4 x 0.28

- 0.30 (RTI = 6

- 8 days) 3

- 4 Combined 3 12 0.04 0.39 0.06 0.35 0.23 0.21 0.10

Tomato/EU 5

491960

- 04 through

- 07 2 x 0.24

- 0.26 (RTI = 6

- 7 days) 0 Combined 3 15 0.05 0.36

-- -- 0.13 0.14 0.08

2

- 3 Combined 3 11 0.04 0.21

-- -- 0.10 0.11 0.05

Tomato/EU 5

491960

- 04 through

- 07 2 x 0.22 (RTI = 6

- 7 days) 0 Combined 3 15 0.04 0.40

-- -- 0.11 0.13 0.10

2

- 3 Combined 3 11 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 (degra dation of the metaflumizone Z isomer to M320I04 was noted)

. 2 LAFT = lowest

- average field

- trial; HAFT = h ighest

- a verage f ield

- t rial

. Only a single samples is collected form the EU trials; therefore, LAFT and HAFT are not applicable

. 3 Combined metaf

lumizone (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 th e 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 indica ted 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 JM P R 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)

.

T he 2009 JMPR rep ort also included a summary of a study concerning the nature of metaflumizone
residue s under simula ted processing conditions (MRID 49196008) ; h ydrolyses of benzonitrile ring

- U

-Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 13 of 19 

### [ 14 

### C]metaflumizone and trifluromethoxyphenyl ring

- U

- [ 14 

### C]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). Me taflumizone was not stable at pH 4 and pH 5 (90 °C

– 100 °C) with loss es as much as 40% (t he 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

ma jor 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

T able 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 f or 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 , t he available EU and U.S. field trial data result ed 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 metaflu mizone (E and Z isomers) and M320I04 is recommended (0.39 x 2.94 = 1.15).Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 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 day s; 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 h armonization with the Codex 0.6

- ppm pepper MRL is not appropriate. Based on the U.S. pepper (bell and non

- be ll) 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 tolera nce 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 establis hed 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 a n 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, applicat ion 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 gener al, 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 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 NAFT A tolerance

calculation procedure which allowed the establishment of tolerances less than the highest residues;
the OECD tolerance

- calculation procedure , which was employed here in , does not permit this; and/or (3) the JMPR report indicated that only two applications were permitted to pepp ers 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 H ED

- 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

- 20 1 3 )

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 D 412301

P age 15 of 19 

### Attachment 1 : International Residue Limits

.

Summary of US and International Tolerances and Maximum Residue Limits

Residue Definition

US Canada Mexico 2 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 (calcul ated in parent equivalents) None

-- Plant and A nimal
commodities: metaflumizone, sum of
metaflumizone E

- isomer
and metaflumizone Z

isomer. The residue is fat

soluble.

Tolerance/Maximum Residue Limit (ppm)

Commodity 1 US Canada Mexico 2 Codex

t omato 0.60

-- -- 0.6

tomato, paste 1.2

-- -- -- p epper 1.5

-- -- 0.6; 6 peppers, chili dried

e ggplant 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 D 412301

P age 16 of 19 

### Attachment 2: OECD Tolerance Calculations.Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 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,α

trifluoro

- m

- tolyl)ethylidene]

- 4

- (trifluoromethoxy)carbanilohydrazide

M320I04 4

- [2

- oxo

- 2

- [3

- (trifluoromethoxy)phenyl]ethyl]

- benzonitrile

M320I05

--

M320I06 4

- cyanobenzoic acid

M320I07 hydroxyl parent

M320I08

--

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]

- acetamideMetaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 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. LAFT 2 HAFT 2 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

Combined 3 7 0.05 0.66 0.05 0.55 0.33 0.32 0.17

Sweet Peppers/EU 5
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 0.0 2 0.0 2

-- -- 0.0 2 0.0 2

-- Combined 3 10 0.1 1 0.8 3

-- -- 0.2 7 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 0.0 2 0.0 2

-- -- 0.0 2 0.0 2

-- Combined 3 10 0.0 9 0.6 3

-- -- 0.21 0.2 4 0.14

Sweet Peppers/EU 5
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 0.0 2 0.0 2

-- -- 0.0 2 0.0 2

-- Combined 3 10 0.0 8 0.5 7

-- -- 0.2 9 0.2 8 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 0.0 2 0.0 2

-- -- 0.0 2 0.0 2

-- Combined 3 10 0.0 9 0.3 7

-- -- 0.19 0.2 2 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

Combined 3 4 0.11 0.58 0.12 0.57 0.22 0.28 0.20
Pepper/Korea 4 ,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

-- Combined 3 1 0.17 0.21

-- -- -- 0.19

-- Pepper/Korea 4 ,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

-- Combined 3 1 0.20 0.24

-- -- -- 0.22

--Metaflumizone Summary of Analytical Chemistry and Residue Data D 412301

P age 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. LAFT 2 HAFT 2 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

Combined 3 12 0.04 0.39 0.06 0.35 0.23 0.21 0.10

Tomato/EU 5
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 0.0 2 0.0 2

-- -- 0.0 2 0.0 2

-- combined 15 0.0 5 0.3 6

-- -- 0.1 3 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

-- Combined 3 11 0.04 0.21

-- -- 0.10 0.11 0.05

Tomato/EU 5
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

-- Combined 3 15 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

-- Combined 3 11 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 ha rvest to analysis (degradation of the metaflumizone Z isomer to M320I04 was noted)

. 2 LAFT = lowest

- average field

- trial; HAFT = highest

- average field

- t rial

. Only a single samples is collected form the EU trials; therefore, LAFT and HAFT are not applica ble

. 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 magnitu de of the residue summaries were utilized for the residue trials conducted in the EU (DERs were not generated).