### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C

. 20460



### MEMORANDUM

DATE: Decemb er 19

, 2012 O FFICE O F CHEMICAL SAFETY AND
POLLUTION PREVENTION



### SUBJECT: F l umioxazin. Petition for the Section 3 Registration and Estab li shmen t of

Toler ances for uses on Artichoke

, Ca bba ge, O li ve , Pomegranate

, and Prickly Pear
Cactus. Summary of Analytical Chemistry and Residue Chemistry Data.

PC Code: 129034

Decision No.: 450810

Petition: # 1F7886

Risk Assessment Type: S in g l e Chemical Agg r egate
TXRNo.: NA

MRID Nos

. : 487 30701-48 730705 DP Barcode: D406070 Registration No .: 59639-97 Regulatory Action : Section 3 Registration

Case No .: 7244

CAS No.: 103361-09-7

40 CFR: § 1 80.56 8

FROM: Sheila Piper, Chemist

# ~**~** Risk Assessment Branch VI

Health Effec t s Division (7509P)

THROUGH: Christine Olinger, Acting Branch Chief 

# /J / / _/

. Risk Assessment Branch VI

# ~~ Health Effects Division (7509 P )

TO: Andrew Ertman, Barbara Madden RM05
Risk Int egration

, Minor Use

, and Emergency Response Branch Registration Division (7505P)Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 2 of 24 Table of Contents

Contents

EXECUTIVE SUMMARY

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

REGULATORY RECOMMEND ATIONS

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

P RE

- R E GISTRATION D ATA N EEDS

................................ ................................ ................................ ................................ ...... 3 Analytical Methods

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

R ECOMMENDED T OLERANCES

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

I NTERNATIO NAL H ARMONIZATION

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

R EVISIONS TO P ETITIONED

- F OR T OLERANCES

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

R ESIDUE P ROFILE

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

RESIDUE CHEMISTRY GU IDELINES

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

D IRE CTIONS FOR U SE (860.1200)

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

860.1340 R ESIDUE A NALYTICAL M ETHODS

................................ ................................ ................................ ...................... 8 Enforcement method in plant commodities

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

Enforcement method in animal matrices

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

860.1360 M ULTIRESIDUE M ETHODS

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

860.1380 S TORAGE S TABILITY

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

860.1460 F OOD H ANDLING E STABLISHMENTS

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

860.1480 M EAT
, M ILK
, P OULTRY
, AND E GGS

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

860.1500 C ROP F IELD T RIALS

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

860.1520 P ROCESSED F OOD AND F EED

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

TOLERANCE DERIVATION

................................ ................................ ................................ ................................ ..... 17

APPENDIX 1. FIELD TRIAL DATA AND OECD MRL CALCULATOR OUTPUT

................................ ............................. 20

APPENDIX 3. NOMENCL ATURE AND STRUCTURES OF IMPORTANT METABOL ITES AND DEGRADATES FOUND IN

METABOLISM STUDIES I N PRIMARY CROPS AND LIVESTOCK.

................................ ................................ .............. 22



### Th e DER was originally prepared by California Department of Pesticide Regulation ( 1001 I Street, Sacramento, CA 95812 ; submitted 07 /1 6 /1 2 ). The DER has been reviewed by the Health Effects Division (HED) and revised to reflect current Office of Pesticide Programs (OPP) policies.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 3 of 24 Executive Summary

Flumioxazin belongs to the N

- phenylphthalimide class of herbicides (Group 14). It is a light

dependent peroxi dizing herbicide (LDPH) which acts by blocking heme and chlorophyll biosynthesis, resulting in an endogenous accumulation of porphyrins which are known to have a phototoxic mode of action in plants. Flumioxazin is currently registered for pre

- and post

em ergence applications on a variety of fruit, vegetable, and field crops for the control of susceptible weeds.

The petitioners, Valent U.S.A. Corporation and IR

- 4 ( The Interregional Research Project No. 4 ), are requesting registration and establishment of p ermanent tolerances of flumioxazin on artichoke, cabbage, olive, pomegranate, and prickly pear cactus

. The end

- use product s being proposed for use on these sites are Valor Herbicide (EPA Reg. No. 59639

- 99) and Chateau Herbicide (EPA Reg. No. 59639

- 119, wa ter dispersible granule)

, which are formulated as a water dispersible granule (WDG) containing 51 % flumioxazin by weight

. The maximum single application rate proposed for olive, pomegranate, and prickly pear cactus is 0.3 8 lb ai/A,
artichoke is 0.19 lb ai/ A, and cabbage and Chinese cabbage are 0.13 lb ai/A

. Applications are to be made using ground and aerial equipment. The proposed pre

- harvest interval s (PHI) are 5 or 10 days.

The nature of flumioxazin residues in plants and animals is adequately understood based on acceptable soybean, peanut, corn, sugarcane, grapes, ruminant

, and poultry metabolism studies

. The residue of concern for plants is only the parent compound. The residues of concern for ruminants should include parent, 3

- OH

- flumioxazi n, 4

- OH

- flumioxazin, and Metabolites B, C, and F. For poultry, the residues of concern are parent, 3

- OH

- flumioxazin, 4

- OH

- flumioxazin,
and 4

- OH

- S

- 53482

- SA. Flumioxazin tolerances are established under 40 CFR § 180.568 and range from 0.02 to 8.0 ppm on a w ide variety of fruits, vegetables, and field crops. No livestock
tolerances have been established

. Acceptable data were submitted depicting analytical methods, storage stability, and residues in target crops. The data are adequate to support tolerance

ev aluation/enforcement and human health risk assessment.

R egulatory R ecommendations

Provided the submitted Section F, there are no residue chemistry issues that would preclude granting the requested Section 3 registration for f lumioxazin and for the recommended tolerances on the proposed commodities as listed in Table 1

.

Pre

- Registration Data Needs

The registrant needs to submit a revised Section F in which the recommended tolerances listed in
Table 1 are proposed.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 4 of 24 Analytical Method s

Enforcement Method

- An adequate gas chromatography /nitrogen phosphorus detector ( GC/NPD ) method is available for enforcing tolerances for residues of flumioxazin in/on plant commodities (MRID 43935509, Valent Residue Method #RM

- 30A

- 1, Determination of
Flu mioxazin Residues in Crops; No DP#, 1/8/96, J. Garbus). This method has undergone a successful independent laboratory validation (ILV) trial and a successful petition method validation (PMV) trial by the Agency. The reported method limit of detection ( LO D ) and limit of quantitation ( LO Q ) for flumioxazin are 0.0 1 0 and 0.0 2 0 ppm, respectively.

Briefly, residues were extracted with acetone:water (4:1, v:v) and then partitioned into dichloromethane (DCM). After evaporation of the DCM, residues were purifi ed by partitioning between hexane/acetonitrile (ACN). The residues in the ACN phase were then concentrated, re

dissolved in hexane/ethyl acetate, and purified using a Florisil column eluted with hexane:ethyl acetate (2:1 v:v). Residues in the eluate were concentrated, reconstituted in acetone, and then analyzed by GC/NPD or GC/ mass selective detector ( MSD ) , using an external standard.

Data Collection Method s

- The enforcement method ( RM

- 30A

- 1 ) and data collection methods
are similar.

Multiresidue Method

- Data depicting the analysis of flumioxazin and degradates 482

- HA and APF through FDA Multiresidue Protocols were submitted to FDA for review. The multiresidue method testing data indicate that flumioxazin is not recovered through Sections 304 and 402 of

P AM, Vol. I.

Recommended Tolerances

HED recommends that CFR 40 § 180.568[a] be amended by establishing tolerances for the plant
commodities listed in the T able 1

. T he tolerances should be defined as follows:

Tolerances are established for residues of t he herbicide flumioxazin , including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance
levels for f

lumioxazin is to be determined by measuring only f lumioxazin 2

- [7

- fluoro

- 3,4

- dihydro

- 3

- oxo

- 4

- (2

- prop ynyl)

- 2 H

- 1,4

- benzoxazin

- 6

- yl]

- 4,5,6,7

- tetrahydro

- 1 H

- isoindole

- 1,3(2

H )

- dione

.

Table 1 . Tolerance Summary for F lumioxazin Commodity Proposed
Tolerance (ppm) HED

Recommended Tolerance (ppm) Comments (correct

commodity definition)

A rtichoke 0.02 0.02 Cabbage 0.02 0.02 Chinese Cabbage 0.02 0.0 2

Olive 0.02 0.02 Pomegranate 0.02 0.0 2

Prickly pear cactus

, fruit 0.1 0.07Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 5 of 24 Table 1 . Tolerance Summary for F lumioxazin Commodity Proposed
Tolerance (ppm) HED

Recommended Tolerance (ppm) Comments (correct

commodity definition)

Prickly pear cactus

, pads 0.05 0.06



### International Harmonization

There are no Codex, Canadian or Mexican MRLs established for residues of flumioxazin on commodities associated with this petition . Tolerances for livestock commodities are not re quir ed at this time since there is no reasonable expectation of finite residues.

Revisions to Petitioned

- For Tolerances

T he proposed tolerances are different for cactus from th ose recommended by HED

. HED used
the Organization for Economic Co

- operation and Development ( OECD ) calculation procedures
to establish the tolerances recommended. The registrant should submit a revised Section F in which the proposed tolerances are the same as those recommended by HED.

Residue Profile

The n omenclature and physiochemical properties of flumioxazin are presented below in Tables 2
and 3. The chemical names and structures of flumio xazin residues of concern are presented in Appendix 3.

TABLE 2

. Test Compound Nomenclature

Flumioxazin

Common name Flumioxazin Company experimental

name VC

- 1152

IUPAC name N

- (7

- fluoro

- 3,4

- dihydro

- 3

- oxo

- 4

- prop

- 2

- ynyl

- 2 H

- 1,4

- benzoxazin

- 6

- yl)cyclohex

- 1

- ene

- 1,2

- dicarboxamide

CAS name 2

- [7

- fluoro

- 3,4

- dihydro

- 3

- oxo

- 4

- (2

- propynyl)

- 2 H

- 1,4

- benzoxazin

- 6

- yl]

- 4,5,6,7

- tetrahydro

- 1 H

- isoindole

- 1,3(2 H )

- dione

CAS # 103361

- 09

- 7

End

- use product/(EP) ValorTM WDG Herbicide, ChateauTM WDG H erbicide



### TABLE 3

. Physicochemical Properties of the Technical Grade Test Compound

Parameter Value ReferenceFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 6 of 24 TABLE 3

. Physicochemical Properties of the Technical Grade Test Compound

Parameter Value Reference Melting point/range 202

– 204°C US EPA Fact Sheet issued April 12, 2001. pH (25°C) 7.29 Density (25°C) 1.51 Water solubility (mg/L at 25°C) 1.79 Solvent solubility (mg/L at 25°C) 17 Acetone
32.3 Acetonitrile 17.8 Ethyl Acetate
191 Dichloromethane Pesticide Manual

Vapo r pressure (22°C) 2.41 x 10 - 6 

### mmHg US EPA Fact Sheet issued April 12, 2001. Dissociation constant (pK
a 

### ) None Octanol/water partition coefficient Log(K OW 

### ) 2.55 at 20°C

UV/visible absorption spectrum λ 218 

### λ 216 

### λ 216



### Residue Chemistry Guidelines

Directions for Use (860.1200)

Valent USA Corporation is proposing the use of the herbicide flumioxazin on artichoke, cabbage, Chinese cabbage, olive, pomegranate, and prickly pear cactus

. The end

- use product s being proposed for use on these sites are Valor Herbicide (EPA Reg. No. 5963 9

- 99) and Chateau Herbicide (EPA Reg. No. 59639

- 119, water dispersible granule)

, which are formulated as a water dispersible granule (WDG) containing 51 % flumioxazin by weight

. The maximum single application rate proposed for olive, pomegranate, and prickly pear cactus is 0.3 8 lb ai/A, artichoke is 0.19 lb ai/A, and cabbage and Chinese cabbage are 0.13 lb ai/A

. Applications are to be made using ground and aerial equipment.

The use pattern for the proposed uses of flumioxazi n is summarized in Table 4, below.

Table 4 . Summary of Directions for Proposed Use s of Flumioxazin.

Applic. Timing, Type, and Equip. Formulation

[EPA Reg.

No. 59639

- 99, 59639

- 119 ] Applic.

Rate (lb ai/A) Max. No.

Applic. per
Season Max.

Seasonal Applic. Rate (lb ai/A) PHI Use Directions and
Limitations

Prickly Pear Cactus

Ground

, Chemigation, Dry Bulk

Fertilizer Water

Dispersible
Granule 0.38 lb

ai/A 1 0.38 lb ai/A (1.91 lb
ai/ton fertilizer) 60 days Apply as a

preemergencence and postemergence application. Apply as a uniform broadcast application to the plantation floor or as a uniform band directed at the base of the agave. DoFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 7 of 24 Table 4 . Summary of Directions for Proposed Use s of Flumioxazin.

Applic. Timing, Type, and Equip. Formulation

[EPA Reg.

No. 59639

- 99, 59639

- 119 ] Applic.

Rate (lb ai/A) Max. No.

Applic. per
Season Max.

Seasonal Applic. Rate (lb ai/A) PHI Use Directions and
Limitations

not apply over the top of crop or allow spray to
come in contact with cr op as a result of application or
drift. Use a minimum of 15 gallons of spray solution

per acre. Olive, Pomegranate

Ground Chemigation, Dry Bulk

Fertilizer Water

Dispersible
Granule 0.38 lb

ai/A 1 0.38 lb ai/A ( 1.91 lb
ai/ton fertilizer) 60 days Apply after bud break

through final harvest using shielded application equipment if the applicator can ensure the spray drift
will not come into contact
with non

- target vegetation, crop fruit and/or foliage.

Artichoke

Ground

, aerial

and Chemigation, Dry Bulk

Fertilizer Water

Dispersible
Granule 0.19 lb

ai/A 1 0.19 lb ai/A (1.91 lb
ai/ton fertilizer) None Apply as a pre

- plant

application for preemergence control of
weeds.

Cabbage, Chinese Cabbage

Ground Chemigation, Dry Bulk

Fertilizer Water

Dispersible
Granule 0.13 lb

ai/A 1 0.13 lb ai/A (1.91 lb
ai/ton fertilizer) None All applications must be

made with shielded or hooded equipment in row
middles between raised plastic mulched beds. Do not apply after crops are transplanted.



### Conclusions

. The use directions are adequate to allow evaluation of the field trial data for artichoke, cabbage, olive, pomegranate

, and prickly pear cactus relative to the proposed uses

.

860.1300 Nature of the Residue

- Plants

Residue Chemistry Memo DP# 301247, 7/23/04, W. Drew
MARC Decision Memo D P# 272652, 3/12/01, R. Loranger Residue Chemistry Memo D P# 259493 , 3/12/01, D. Dotson



### Adequate plant metabolism studies are available depicting the u ptake and metabolism of [ 14 

### C]flumioxazin following applications to soybean (preemergence), peanut (preemergence), corn (preemergence), sugarcane (directed to the lower 3 feet of plants), and grapes (directed to soil surface surrounding vines).Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 8 of 24 Conclusio ns: Based on plant metabolism studies, HED determined that the parent compound only is the residue of concern to be used in risk assessments and the tolerance expression for primary and rotated crops. The available data are adequate to support the uses proposed herein.

860.1300 Nature of the Residue

- Livestock

MARC Decision Memo D P# 272652, 3/12/01 , R. Loranger Residue Chemistry Memo DP# 259493, 3/12/01, D. Dotson Residue Chemistry Memo DP# 194 594, 9/21/94, J. Garbus



### Adequate ruminant and poultry metabolism studies are available depicting the metabolism of flumioxazin radiolabeled in either the phenyl or tetrahydrophthaloyl (THP) ring. The
metabolism of flumioxazin is similar in both ruminants and poultry, involving the hydroxylation and reduction of the cyclohexene ring in the THP moiety, hydrolytic cleavage of the imide and amide linkages, and incorporation of sulfonic acid into the THP moiety.

Conclusions : HED has determined that the residues of concern for ruminants should include parent, 3

- OH

- flumioxazin, 4

- OH

- flumioxazin , and Metabolites B, C, and F. For poultry, the residues of concern are parent, 3

- OH

- flumioxazin, 4

- OH

- flumioxazin, and 4

- OH

- S

- 53482

- SA.

860.1340 Residue Analyt ical Methods

Residue Chemistry Memo DP# 259493, 3/12/01, D. Dotson Residue Chemistry Memo DP# 342963, 11/20/07, D. Rate Residue Chemistry Memo No DP# , 1/8/96

, J. Garbus



### Enforcement method in plant commodities

Enforcement method: An adequate GC/NPD method is available for enforcing tolerances for residues of flumioxazin in/on plant commodities (MRID 43935509, Valent Residue Method

#RM

- 30A

- 1, Determination of Flumioxazin Residues in Crops; No DP#, 1/8/96, J. Garbus).
This method ha s undergone a successful independent laboratory validation (ILV) trial and a successful petition method validation (PMV) trial by the Agency. The reported method LOD and LOQ for flumioxazin are 0.010 and 0.020 ppm, respectively.

Data collection method : Samples of artichoke, cabbage, olive, pomegranate, and prickly pear cactus commodities from the submitted crop field trial were analyzed for residues of flumioxazin using a GC/NPD/MSD method entitled “ Residue Analysis of Flumioxazin by GC/Nitrogen Phosph orous Detector. ” This method is a more recent version of Method RM

- 30A

- 1.

Briefly, residues were extracted with acetone:water (4:1, v:v) and then partitioned into dichloromethane (DCM). After evaporation of the DCM, residues were purified by partition ing between hexane/acetonitrile (ACN). The residues in the ACN phase were then concentrated, re

dissolved in hexane/ethyl acetate, and purified using a Florisil column eluted with hexane:ethyl acetate (2:1 v:v). Residues in the eluate were concentrated, reconstituted in acetone, and then analyzed by GC/NPD or GC/MSD, using an external standard.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 9 of 24 Conclusion: The GC/NPD methods used for data collection are adequately for determining
residues of flumioxazin in artichoke, cabbage, olive, pomegranate, and prickly pear cactus commodities. The methods were validated in conjunction with the analysis of samples from the
field trial . The validated method LOQ for flumioxazin was 0.02 ppm, and the LOD was 0.01 ppm, for all matrices.

Enforcement m ethod in a nim al matrices

An enforcement method for animal matrices was not submitted and is not required based on the no expectation of residues in livestock commodities.

Adequate data collection methods were submitted in conjunction with the cattle feeding study ( DP # 342963) . Residues of flumioxazin and its two hydroxy metabolites (3

- OH

- flumioxazin
and 4

- OH

- flumioxazin) were determined in milk and tissues using two related LC/MS/MS methods, Valent Methods RM

- 30MK for milk and RM

- 30T for tissues. The methods were
ad equately validated in conjunction with the analysis of the feeding study samples using control samples of milk and tissues fortified with each analyte at 0.02 and 0.1 ppm. For both methods, the validated LOQ is 0.02 ppm for each analyte, and the reported LOD is 0.01 ppm.

Conclusions. No additional residue analytical methods data for livestock commodities are required at this time.

860.1360 Multiresidue Methods

Residue Chemistry Memo DP # 259493, 12 / MAR / 20 01

, D. Dotson Residue Chemistry Memo DP # 397086

, 22 / FEB / 20 1 2, W

. T. D rew



### An adequate gas chromatography/nitrogen

- phosphorus detection (GC/NPD) method, Valent
Method RM30

- A

- 1, is available for enforcing tolerances for residues of flumioxazin per se in/on plant commodities. The reported method lim its of quantitation and detection (LOQ and LOD) for flumioxazin in/on plant commodities are 0.02 and 0.01 ppm, respectively.

Data depicting the analysis of flumioxazin through FDA Multir esidue Protocols were submitted
and the availa ble data indicate that flumioxazin could not be recovered through application of the FDA multiresidue protocols.

860.1380 Storage Stability

DER References: 48730701.DER ( Artichoke )

48730702.DER (Cabbage) 48730703.DER (Olives)

48730704.DER (Pomegranate) 48730705.DER (Prickly Pear Cactus)Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 10 of 24 Storage stability data for flumioxazin residues in various plant commodities are conducted in conjunction with the residue study on flumioxazin . R esidues were stable in/on artichoke when
stored frozen fo r up to 252 days for artichoke, 232 days for cabbage, 532 days for olives, 504 days for pomegranate, and 168 days for cactus. The submitted storage stability results are adequate to support the storage duration for samples of artichoke, cabbage, olive, po megranate, and prickly pear cactus

.

Sample storage intervals and conditions

Samples collected from the field trial and processing studies were stored frozen prior to residue analysis. S torage durations and conditions of samples are presented in Table 5

.

Table 5 . Summary of Storage Conditions and Intervals of Samples from Field Trials.

Matrix Storage

Temperature a (°C) Actual Storage Duration (days) 1 Interval of Demonstrated Storage Stability (days)

Crop Field Trial Studies

Artichoke

- 21 + 7 o 221

- 225 days (7.3

- 7.4 months) 2 52 days (8 months) in artichoke
Cabbage 232 days (7.6 months) 243 days ( 8 months) in cabbage

Olive 532 days 526 days

Olive Oil 510 days 479 days
Pomegranate 496

- 503 days ( 16.5

- 16.7 months) 504 days

Prickly Pear

Cactus

- fruit 134

- 175 days ( 4.4

- 5.75 months) 165 days

Prickly Pear

Cactus

- pads 71

- 76 days (2.3

- 5.75 months) 168 days

a Whole frozen field samples were placed in frozen storage at

- 21 + 7 o C upon receipt at the laboratory. Durng processing for analysis, samples were moved and held temporarily (<1 day) in a freezer at

- 11 + 11 o C. While outside the freezer they were maintained on dry ice. Gro und samples were then returned to frozen storage at

- 21 + 7 o C

.



### 860.1400 Wa ter, Fish, and Irrigated Crops

There are no proposed uses in the current petition that are relevant to this guideline topic.

860.1460 Food Handling Establishments

There are no proposed uses for which this guideline topic is relevant.

860.1480 Meat, Milk, Poultry, and Eggs

The new uses on artichoke, cabbage, olive, pomegranate, and prickly pear cactus are not livestock feedstuffs; therefore, HED concludes that toleran ces are not required for animal
commodities.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 11 of 24 860.1500 Crop F ield Trials

DER References: 48730701

. DER ( Artichoke )

48730702.DER (Cabbage) 48730703.DER (Olives) 48730704.DER (Pomegranate) 48730705.DER (Prickly Pear Cactus)



### Cro p field trials were conducted with artichoke, cabbage, olive, pomegranate, and prickly pear

cactus following application of Valor TM Herbicide (51% water dispersible granule (WDG) to
control broadleaf weeds.

Artichoke

The Interregiona l Research Project No. 4 (IR

- 4) h as submitted field trial data for flumioxazin on artichoke

. Three field trials were conducted in the United States during the 2007 growing season
in the North American Free Trade Agreement (NAFTA) Growing Zone 10 (CA).

At all trial locations, one treated plot received one broadcast pre

- plant application of flumioxazin (51% WDG) was made to the soil surface 1

- 4 days before transplanting artichoke at rates of

0.187

- 0.191 lb ai/A. The applications were made in a spray volume of 30

- 50 gal/A, and did not
incl ude an adjuvant in the spray mixture. Artichoke RAC samples (flower heads) were harvested at commercial maturity, 126

- 147 days after treatment.

Residues of flumioxazin in/on artichoke were quantitated by gas chromatography (GC) nitrogen phosphorous det ection (NPD) using the Cornell Analytical Laboratory Method entitled, “Residue Analysis of Flumioxazin on Artichoke by GC/NPD, Version #9.” This method was adapted with

minor modifications from Valent Method RM

- 30A

- 1. For method validation, control sampl es of artichoke were fortified with flumioxazin at 0.02 and 0.2 ppm. Recoveries from artichoke were

80

- 115% (96 ± 14%, n = 6). Concurrent recoveries from control artichoke samples fortified at 0.02 ppm were 70

- 90% (83 ± 10%, n = 6). The lowest level of meth od validation for residues of flumioxazin in/on artichoke samples was 0.02 ppm. The calculated limit of detection (LOD) and limit of quantitation (LOQ) for flumioxazin residues in/on artichoke samples were 0.005 ppm and 0.016 ppm, respectively.

The results from these trials showed that flumioxazin residues in/on artichoke were <0.02 ppm in/on all artichoke samples harvested 126

– 147 days after one pre

- transplant application of
flumioxazin at the rate of 0.191 lb ai/A. No residue decline studies were submitted.

TABLE 6

. Summary of Residue Data from Crop Field Trials with Flumioxazin. Commodity Total Applic.

Rate (lb ai/A) PHI 1

(days) Residue Levels (ppm)

n Min. Max. HAFT 1 Median Mean Std.

Dev.

Artichoke 0.187

– 0.191 126

- 147 6 <0.02 <0.02 <0.02 <0.02 <0.02

-

1 HAFT = Highest Average Field TrialFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 12 of 24 Conclusion: The submitted residue data for artichoke are adequate to satisfy data requirements. The studies reflect the maximum proposed use pattern for artichoke, and the number and
locations of the field trials are in accordance with OCSPP 860.1500. The data were generated using a validated analytical method and are supported by adequate storage s tability data. The residue data for artichoke were entered into the Agency’s OECD calculator to determine appropriate tolerance levels ; see Appendix I . The tolerance spreadsheet recommends tolerances
of 0.0 2 ppm for artichoke

.

Cabbage

The Interregional Research Project No. 4 (IR

- 4) h as submitted field trial data for flumioxazin on cabbage

. Eight field trials were conducted in the United States during the 200 6 growing seasons
in the North American Free Trade Agreement (NAFTA) Growing Zones 1 (NY; 1 trial), 2 ( NJ,
NC ; 1 trial each ), 3 (FL; 1 trial), 5 (WI; 1 trial), 6 (TX; 1 trial), 8 (CO; 1 trial), and 10 (CA; 1
trial ).

At all trial locations, one pre

- plant broadcast application of flumioxazin (51% WDG) was made
to the soil surface 0

- 5 days before transplanting, at rates of 0.045

- 0.048 lb ai/A (low rate) or
0.094

- 0.097 lb ai/A (high rate). The applications were made in a spray volume of 20

- 36 gal/A, and did not include an adjuvant in the spray mixture. Cabbage samples (fresh cabbage heads with wrapper leaves) were harvested at commercial maturity, 55

- 104 days after treatment.

Residues of flumioxazin in/on cabbage were quantitated by gas chromatography (GC) nitrogen phosphorous detection (NPD) using the Cornell Analytical Laboratory Metho d entitled, “Residue Analysis of Flumioxazin on C a bbage by GC/NPD, Version #8.” This method was adapted with

minor modification s from Valent method RM

- 30A

- 1. For m ethod v alidation, control samples of cabbage were fortified with flumioxazin at 0.02 and 0. 2 ppm. Recoveries from cabbage were 85

- 90% (89 ± 2%, n = 6). Concurrent recoveries from control cabbage samples fortified at 0.02 ppm were 80

- 120% (103 ± 12%, n = 15). The lowest level of method validation for residues of flumioxazin in/on cabbage sampl es was 0.02 ppm. The LOD and LOQ for flumioxazin residues in/on cabbage samples were 0.0 063 ppm and 0.0 19 ppm, respectively

.

The results from these trials showed that maximum residues of flumioxazin in/on cabbage were <0.02 ppm in/on all cabbage samples harvested 55

– 104 days after one pre

- transplant application of flumioxazin (51% WDG) at rates of 0.045

- 0.048 lb ai/A (low rate) or 0.094

- 0.097 lb ai/A (high rate). A residue decline study was not submitted.

TABLE 7

. Summary of Residue Data from Crop Field Trials with Flumioxazin. Commodity Total

Applic.

Rate (lb ai/A) PHI

(days) Residue Levels (ppm)

n Min. Max. HAFT * Median Mean Std.

Dev.

Low RateFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 13 of 24 Cabbage, Fresh, with

wrapper leaves 0.045

-

0.048 55

- 104 16 <0.02 <0.02 <0.02 <0.02 <0.02

-

High Rate Cabbage, Fresh, with

wrapper leaves 0.094

-

0.097 55

- 104 14 <0.02 <0.02 <0.02 <0.02 <0.02

-

* HAFT = Highest Average Field Trial



### Conclusions : The submitted residue data for cabbage are adequate to satisfy data requirements. The studies reflect the maximum proposed use pattern for cabbage, and the number and locations
of the field trials are in accordance with OCSPP 860.1500. The data were generated using a validated analytical method and are supported by adequate storage sta bility data. The residue
data for cabbage were entered into the Agency’s OECD calculator to determine appropriate tolerance levels; see Appendix I . The tolerance spreadsheet recommends tolerances of 0.0 2 ppm for cabbage

.

Olive

The Interregional Rese arch Project No. 4 (IR

- 4) h as submitted field trial data for flumioxazin on
olive

. Five field trials were conducted in the United States during the 2008 growing seasons in
the North American Free Trade Agreement (NAFTA) Growing Zones 10 (CA).

At all trial locations, two broadcast applications of flumioxazin (51% WDG) were made to the
orchard floor a t a 60

- day interval at rates of 0.364

- 0.390 lb ai/A for a total rate of 0.742

– 0.779
lb ai/A . The applications were made in a spray volume of 22

- 35 gal/A, and included an adjuvant in the spray mixture . Olive RAC samples ( fruit without pits) were harvested at 56

- 59 days after
the last treatment. At one location, two broadcast exaggerated rate (5X) applications of
flumioxazin were made to the or chard floor at a 60

- day interval at rates from 1.831

- 1.848 lb ai/A. Olive samples (fruit with pits) were harvested at 56 days after the last application and were processed into olive oil according to normal commercial practice.

Residues of flumioxazin in/on olives were quantitated by gas chromatography (GC) with mass selective detection (MSD) in selective ion monitoring mode (SIM) using a method derived from
the Valent method RM

- 30

- A

- 3 “Determination of flumioxazin residues in crops

. January 23,
1990. Revised January 8, 1996 ” For m ethod v alidation, control samples of olive fruit without pits and olive oil were fortified with flumioxazin at 0.02 and 0.2 ppm. Recoveries from fortified olive fruit without pits were 76

- 122% (103 ± 15%, n = 6) and fortifi ed olive oil were 82

- 116% (94 ± 13%, n= 6). Concurrent recoveries from control olive fruit without pits samples fortified at 0.02 ppm were 87

- 102% (92 ± 6%, n = 5)

. Concurrent recoveries from control olive oil samples fortified at 0.02 ppm were 8 9

- 10 3 % ( 98 ± 8%, n=3). The lowest level of method validation for
residues of flumioxazin in/on olive fruit without pits and oil samples was 0.02 ppm. The LO Q
calculated for flumioxazin in/on olive and olive oil was 0.021 ppm and 0.01 7 ppm, respectively.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 14 of 24 The r esults from these trials showed that flumioxazin residues in/on olives were <0.02 ppm in/on all olive samples harvested 56

- 59 days after two applications at a rate of 0.375 lb ai/A. A residue decline study was not submitted.

TABLE 8

. Summary of Residue Data from Crop Field Trials with Flumioxazin.

Commodity Total

Applic. Rate (lb ai/A) PHI (days) Residue Levels (ppm)

n Min. Max. HAFT * Median Mean Std.

Dev. Olive (fruits without pits) 0.74

– 0.78 56

- 59 10 < 0.02 < 0.02 < 0.02 < 0.02 < 0.02

-

Olive (fruit without pits) 3.68 56 2 < 0.02 < 0.02 < 0.02 < 0.02 < 0.02

-

Olive oil 3.68 56 2 <0.02 <0.02 <0.02 <0.02 <0.02

* HAFT = Highest Average Field Trial.



### Conclusions : The submitted olive field trial data are adequate. The studies reflect the maximum proposed use pattern for olive, and the number and locations of the field trials are in accordance
with OCSPP 860.1500. An acceptable method was used for residue quantitation, and the study is supported by adequate storage stability data. The residue data for olive were entered into the Agency’s OECD calculator to determine appropriate tolerance levels; see Appendix I. The tolerance spreadsheet recommends tolerances of 0.0 2 ppm for olive.

Pomegranate

The Interregional Research Project No. 4 (IR

- 4) h as submitted field trial data for flumioxazin on
pomegranate

. Three field trials were conducted in the United States during the 2008 growing

seasons in the North American Free Trade Agreement (NAFTA) Growing Zones 10 (CA).

At all trial locations, two broadcast applications of flumioxazin (51% WDG) were made to the
orchard floor at an interval of 60 day s at rates of 0.363

- 0.383 lb ai/A. The applications were made in spray volume s of 20

- 36 gal/A

, and include d an adjuvant in t he spray mixture. Pomegranate RAC samples were harvested at commercial maturity, 57

- 5 9 days after treatment.

Residues of flumioxazin in/on pomegranate were quantitated by gas chromatography (GC) mass selective detector (MSD) in selective ion monitoring (SIM) using a method derived from
“Valent method RM

- 30A

- 3 De t ermination of Flumioxazin Residues in Crops”. For m ethod

v alidation, control samples of pomegranate were fortified with flumioxazin at 0.02 and 0.2 ppm. Recoveries from pomegranate were 89

- 10 1% (96 ± 4%, n = 6). Concurrent recoveries from control pomegranate samples fortified at 0.02 ppm were 80

- 103% (92 ± 12%, n = 3 ). The lowest
level of method validation for residues of flumioxazin in/on pomegranate samples was 0.02 ppm. The LOD and LOQ f

or flumioxazin residues in/on pomegranate samples were 0.005 ppm and

0.016 ppm, respectively.

The results from these trials showed that maximum residues of flumioxazin in/on pomegranate were <0.02 ppm in/on all six pomegranate samples harvested 57

– 59 da ys after two applications of flumioxazin (51% WDG) at rates of 0.363

- 0.383 lb ai/A per application. A residue decline study was not submitted.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 15 of 24 TABLE 9

. Summary of Residue Data from Crop Field Trials with Flumioxazin. Commodity Total

Applic.

Rate (lb ai/A) PHI

(days) Residue Levels (ppm)

n Min. Max. HAFT 1 Median Mean Std.

Dev.

Pomegranate 0.73

- 0.76 57

- 59 6 <0.02 <0.02 <0.02 <0.02 <0.02

- 1 HAFT = Highest Average Field Trial



### Conclusion: The submitted pomegranate field trial data are adequate. The studies reflect the maximum proposed use pattern for pomegranate, and the number and locations of the field trials
are in accordance with OCSPP 860.1500. Acceptable methods were used for residue quantitation, and the s tudy is supported by a dequate storage stability data. The residue data for pomegranate was entered into the Agency’s OECD calculator to determine appropriate tolerance levels; see Appendix I . The tolerance spreadsheet recommends tolerances of 0.0 2 ppm for
pomegranate.

Prickly Pear Cactus

The Interregional Research Project No. 4 (IR

- 4) h as submitted field trial data for flumioxazin on

p rickly pear cactus

. Two field trials were conducted in the United States during the 2006 growing seasons in the North American Free Trade Agreement (NAFTA) Growing Zones 10 (CA).

At all trial locations, one control and two treated plots were established. Flumioxazin (51% WDG) was applied twice as a direct application to the base of the plants at 0.380

- 0.39 2 lb ai/acre (low rate) or 0.749

- 0.775 lb ai/acre (high rate). The applications were made in the early winter and in the spring, with a treatment interval of 134

- 139 days. The total rates were 0.77

- 0.78 lb
ai/acre/season and 1.52

- 1.54 lb ai/acre/season. Applications were made in a spray volume of 21

- 39 gal/acre and did not include an adjuvant in the spray mixture. Prickly pear cactus samples (fruit and pads) were harvested at 1, 8 and 14

- 15 days after the last application.

Residues of flumioxazin i n/on prickly pear cactus were quantitated by gas chromatography (GC) nitrogen phosphorous detection (NPD) using the Cornell Analytical Laboratory Method entitled, “Residue Analysis of Flumioxazin on Prickly Pear Cactus Fruit and Pads by GC/NPD, Version

#7. ” This method was adapted with minor modifications from Valent method RM

- 30A

- 1. For method validation, control samples of prickly pear cactus fruit and pads were fortified with flumioxazin at 0.02 and 0.2 ppm.

Recoveries from prickly pear cactus fruit w ere 90

- 110% (98 ± 6%, n = 8) and recoveries from pads were 90

- 120% (98 ± 6%, n = 8). Concurrent recoveries from control fruit and pad samples

were 80

- 120% (101 ± 13%, n = 14) and 70

- 120% (98 ± 12%, n = 15), respectively . The lowest
level of method valida tion for residues of flumioxazin in/on prickly pear cactus samples was 0.02 ppm. The LOD and LOQ for flumioxazin in/on prickly pear fruit were 0.0059 ppm and 0.018 ppm, respectively. The LOD and LOQ for flumioxazin in/ on prickly pear pads were 0.007

ppm and 0.021 ppm, respectively.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 16 of 24 The maximum residues were <0.02 ppm, 0.025ppm, 0.026 ppm, and 0.0 37 ppm in/on prickly pear cactus fruit and 0.026 ppm, 0.022 ppm, and <0.02 ppm in/on prickly pear cactus pads, each harvested 1, 8, and 14

- 15 days, respectively, after the last application. A residue decline study
was not submitted.

TABLE 10

. Summary of Residue Data from Crop Field Trials with Flumioxazin. Commodity Total Applic.

Rate (lb ai/A) PHI

(days) Residue Levels (ppm)

n Min. Max. HAFT 1 Median Mean Std.

Dev.

Low Rate

Fruit 0.767

- 0.776 1 4 <0.02 <0.02 <0.02 <0.02 <0.02

- 8 4 <0.02 <0.02 <0.02 <0.02 <0.02

- 14

- 15 4 <0.02 0.037 0.024 <0.02 0.017 0.014

Pads 0.767

- 0.776 1 4 <0.02 0.02 0.015 <0.02 0.013 0.005

8 4 <0.02 <0.02 <0.02 <0.02 < 0.02

- 14

- 15 4 <0.02 <0.02 <0.02 <0.02 <0.02

- High Rate

Fruit 1.524

- 1.539 1 4 <0.02 <0.02 <0.02 <0.02 <0.02

- 8 4 <0.02 0.026 0.018 <0.02 0.014 0.008

14

- 15 4 <0.02 0.025 0.025 0.017 0.017 0.008

Pads 1.524

- 1.539 1 4 <0.02 0.026 0.023 0.015 0.017 0.008

8 4 <0.02 0.022 0.016 <0.02 0.013 0.006

14

- 15 4 <0.02 <0.02 <0.02 <0.02 <0.02

- For calculations of HAFT, median, mean, and SD, values <0.02 ppm were assigned a value of 1⁄2 LLMV (0.01 ppm)

1 HAFT = Highest Average Field Trial



### Conclusions : The studies reflect the maximum proposed use pattern for cactus, and the number and locations
of the field trials are in accordance with OCSPP 860.1500. ChemSAC recommends selecting the set of two samples per site which had the highest residue (09/26/12). The maximum residues were 0.020, 0.024, 0.025, and 0.037 ppm in/on prickly pear cactus fruit harvested at 15 days and <0.02, 0.02, 0.02, and 0.026 ppm in/on prickly pear cactus pad harvested 1 day. The residue data
for prickly pear cactus fru it was entered into the Agency’s OECD calculator to determine appropriate tolerance levels ; see Appendix I. The tolerance spreadsheet recommends tolerances
of 0.07 ppm for prickly pear cactus fruit and 0.06 ppm for prickly cactus pads

.

860.1520 Processe d Food and Feed

DER References: 48730703.DER (Olives)



### The Interregional Research Project No. 4 (IR

- 4) h as submitted a processing study on olives . In
one trial conducted in CA , two broadcast exaggerated rate (5X) applications of flumioxazin were
made to t he orchard floor at a 60

- day interval at rates from 1.83

- 1.85 lb ai/A. Olive samples (fruit with pits) were harvested at 56 days after the last application and were processed into olive oil according to normal commercial practice. Olive oil samples from t he 5X treated plot showed residues of flumioxazin that were each below LOQ <0.02 ppm.Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 17 of 24 Conclusions

. The submitted olive processing study is acceptable. Samples were analyzed for

f lumioxazin using an acceptable method, and the study is supported by a dequate storage stability
data

. A separate tolerance for olive oil is not needed.

860.1850

- 1900 Confined and Field Accumulation in Rotational Crops Residue Chemistry Memo D P # 259493, 3/12/01 , D. Dotson Residue Chemistry Memo D P # 272652, 3/12/01 , R. Lora nger



### The previously submitted confined rotational crop study is adequate for the proposed uses on the requested commodities . HED has concluded that the residue of concern in rotational crops is the parent compound only. Based on the results of the confi ned accumulation study, HED concluded that the existing rotational crop plantback intervals (PBIs) are acceptable, and that field trials and tolerances in rotated crops are not necessary.

Conclusions

. Current label directions for 51% WG formulation include the following statement: Do not plant any crop except cotton, peanut, soybean and sugarcane earlier than 30 days after application of flumioxazin. In addition, the labels specify a variety of PBIs for different field crops depending on the appli cation rate. For the highest use rate on any rotated crop (0.38 lb ai/A), the specified PBIs are 9 months for cotton, field corn, peanut, rice, sorghum, soybean, sunflower, tobacco and wheat, and 12

- 18 months for all other crops not listed.

Tolerance Derivation

The OECD MRL calculat ion procedures were used to determine the MRLs for all commodities.
The procedures generate MRLs based on mean field trial values. The spreadsheets for the
various commodities can be found in A ppendix 1

.

List of Appendi x

Appendix 1 . Field Trial Data and OECD MRL Calculator Output Appendix 2

. International Residue Limits Appendix 3 . Chemical Structures of Important Metabolites Ident ified in Metabolism Studies and

Analyzed in Field Trials and Livestock Feedi ng Studies

BibliographyFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 18 of 24 DP#: 272652 Subject: PP#7F4841/0F6171; Flumioxazin in/on Peanuts, Soybeans and Sugarcane.

Conclusions of the 12/20/2000 Meeting of the Metabolism Assessment Review
Committee

. From: R. Loranger

To: Y. Donovan
Dated: 3/12/2001 MRID(s): NA

DP#: 2397086 Subject: Flumioxazin. Multiresidue Method Studies on Flumioxazin Degradates, 482

- HA

and APF, Submitted as Conditional Registration Data Pursuant to the Human
Health Risk Assessment for Aquatic Use of the Herbicide ( PP# 8E7438 )

. From: W.T. Drew

To: K. Montague
Dated: 2/22/2012 MRID(s): 48402403 and

- 04

DP#: 194594 Subject: PP# 3G4250: New Chemi cal EUP: V

- 53482, Flumioxazin on Soybeans.

Evaluation of Analytical Methods and of Residue Data.

From: J. Garbus

To: J. Miller, D. Kenny and A. Koscialski
Dated: 9/21/1994 MRID(s): 42884011

- 42884014, 42884016

- 42884019

DP#: Non e Subject: PP# 3G4250: New Chemical EUP: Flumioxazin: Revised Tolerance

Enforcement Method.

From: J. Garbus

To: J. Miller
Dated: 1/08/1996 MRID(s): 43935509

DP#s: 259493 and 268181 Subject: PP#s 7F4841 and 0F6171. Tolerance Petitions for the Use of Flumioxazin on

Peanuts, Soybeans, and Sugarcane. Evaluation of Residue Chemistry and Analytical Methodology

From: D. Dotson

To: D. Kenny and J. Miller
Dated: 3/12/2001 MRID(s): 44013001, 44013002, 44295049

- 44295057Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 19 of 24 DP#: 298647 Subject: Flumioxazin. Tolerance Petition Requesting Section 3 Registration for Food Use

of Flumioxazin on Cotton. Summary of Analytical Chemistry and Residue Data.
Petition Number 1F06296.

From: W. Drew

To: J. Miller
Dated: 2/17/2004 MRID(s): 45375506

DP#: 301247 Subject: Flumioxazin. Tolerance Petition Requesting Section 3 Registration for Food Use

of the Herbicide Flumioxazin on Sugarcane, Grape, Almond/Pistachio, Mint, Tuberous/Corm Vegetables (Crop Subgroup 1C), and Dry Bulb Onion/Garlic/Shallot. Summary of Analytical Chemistry and Residue Data. Petitions Numbered 0F06171, 1F06296, 3E06777, 3E06779, 3E6788.

From: W. Drew

To: Joanne Miller/James Stone
Dated: 7/23/20 04 MRID(s): 45244801, 45375503, 45375504, 45375505, 45375507, 45888501, 46109201,

46114601, 46133901

DP#s: 310408 and 313783 Subject: Flumioxazin. Tolerance Petitions Requesting Section 3 Registration for Food Use

of the Herbicide Flumioxazin on Pome Fr uit (Crop Group 11), Stone Fruit (Crop Group 12), and Strawberries. Summary of Analytical Chemistry and Residue

Data.

From: W. Drew

To: J. Stone, J. Miller and D. Rosenblatt,
Dated: 3/15/2006 MRID(s): 46229401, 46229402, 46229403, 46229404, 46229405, 46229406, 46229407,

46229408, 46292501

DP#: 342963 Subject: Flumioxazin. Petitions for Tolerances on Alfalfa, Asparagus, Dry Beans, Fruiting

Vegetables (Group 8, including Okra), Melons (subgroup 9A), Bushberries (subgroup 13B), and Tree Nuts (group 14 ), and a Request for an Amended Use on Garlic. Summary of Analytical Chemistry and Residue Data. PP#s: 6F7092 and

6E7151.

From: D. Rate

To: D. Rosenblatt, J. Miller, J. Stone
Dated: 11/20/2007 MRID(s): 46889603, 46889604, 47005101, 47005102, 47005103, 47005104, 47005105,

47005106, 47005107Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 20 of 24 DP#: 342413 Subject: Flumioxazin. Petition for the Establishment of Permanent Tolerances on Field

Corn Commodities. Summary of Analytical Chemistry and Residue Data.

PP#7E7243.

From: D. Rate

To: B. Hanson

Date d: 1/31/2008 MRID(s): 47184801

A ppendix 1 : Field Trial Data and OECD MRL Calculator Output

The OECD tolerance calculation procedures were used to generate the tolerances recommended for the proposed crop commodities

. T he residue values in mg/kg liste d in the tables in this attachment are the means of the two samples taken at each trial site.

Ta ble A. 1 . Results from the OECD Calculator

Crop Artichoke Olives Pomegranate Cabbage
Region / Country U.S.A U.S.A U.S.A U.S.A

GAP 0.191 lb ai/A 0.78 lb ai/A 0.76 lb ai/A 0.048 lb ai/A (low rate) Total number of data (n) 3 5 3 8

% of censored data 100 % 100 % 10 0% 0 %

Number of non

- censored
data 0 0 0 8

Lowest residue 0.020 0.020 0.020 0.020
Highest residue 0.020 0.020 0.020 0.020

Median residue 0.020 0.020 0.020 0.020

Mean 0.020 0.020 0.020 0.020
Standard deviation (SD) 0.000 0.000 0.000 0. 000

Correction factor for censoring (CF) 0.333 0.333 0.333 0.333

- Highest residue 0.020 0.020 0.020 0.020

- Mean + 4 SD 0.020 0.020 0.020 0.020

- CF x 3 Mean 0.020 0.020 0.020 0.020

Unrounded MRL 0.02 0 0.0 2 0 0.0 20 0.0 20

Rounded MRL 0.0 2 0.0 2 0.0 2 0.0 2

High uncertainty of MRL
estimate due to small
dataset. High uncertainty of MRL
estimate due to small
dataset. High uncertainty of
MRL estimate due to
small dataset.

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

0.020 * 0.020 * 0.020 * 0.020 *

0.020 * 0.020 * 0.020 * 0.020 *

0.020 * 0.020 * 0.020 * 0.020 *

0.020 * 0.020 *Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 21 of 24

0.020 * 0.020 *

0.020 *

0.020 *

0.020 *

Table A.1. Results from the OECD Calculator

Crop Prickly Pear Cactus
Fruit Prickly Pear

Cactus Pad Region / Country U.S.A U.S.A.

GAP 0.78

- 1.54 lb ai/A 0.78

- 1.54 lb ai/A
Total number of data (n) 4 4

% of censored data 25 % 25 %

Number of non

- censored

data 3 3

Lowest residue 0. 020 0. 020
Highest residue 0.0 37 0.0 26

Median residue 0. 02 5 0. 02 0

Mean 0.02 7 0.02 2

Standard deviation (SD) 0. 00 7 0. 00 3

Correction factor for censoring (CF) 0.833 0.833

- Highest residue 0.02 37 0.0 26

- Mean + 4 SD 0.0 56 0.0 34

- CF x 3 Mean 0.0 66 0.0 54

Unrounded MRL 0.066 0.06

Rounded MRL 0.07 0.0 6

High uncertainty of

MRL estimate due to
small dataset High uncertainty of

MRL estimate due to
small dataset
Residues (mg/kg) Residues (mg/kg)

0.0 37 0.020

0.020 * 0.020 *

0.02 5 0.02 6

0.02 4 0.020



### Appendix 2 : International Residue Limits



## Flumioxazin (129034; 08/31/2012 )
Summary of US and International Tolerances and Maximum Residue LimitsFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 22 of 24 Residue Definition :
US Canada Mexico 2 Codex 3

40 CFR 180.568:

Plant: flumioxazin, 2

- [7

- fluoro

- 3,4

- dihydro

- 3

-

oxo

- 4

- (2

- propynyl)

- 2 H

- 1,4

- benzoxazin

- 6

- yl]

- 4,5,6,7

- tetrahydro

- 1 H

- isoindole

- 1,3(2 H )

- dione

Livestock: N/A 2

- [7

- fluoro

- 3,4

- dihydro

- 3

- oxo

- 4

- (2

- propynyl)

- 2 H

- 1,4

- benzoxazin

- 6

- yl]

- 4,5,6,7

- tetrahydro

- 1 H

isoindole

- 1,3(2 H )

- dione None



### Commodity 1 

### Tolerance (ppm) /Maximum Residue Limit (mg/kg)

US Canada Mexico 2 

### Codex 3

A rtichoke 0.06 Cabbage 0.06 Chinese Cabbage 0.06

Olive 0.06 Pomegranate 0.06 Prickly pear cactus (fruit and pads) 0.07



### Completed: M. Negussie; 08/31/12

1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant.

2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes.

3 * = absent at the limit of quan titation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated commodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have n ot been finalized by the CCPR and the CAC.



### A ppendix 3 : Nomenclature and S tructures of Important Metabolites and Degrada tes
Found in Metab olism Studies in Primary Crops and Livestock

.

Common name Chemical name Chemical structure

Flumioxazin 2

- [7

- fluoro

- 3,4

- dihydro

- 3

- oxo

- 4

- (2

- propynyl)

- 2 H

- 1,4

- benzoxazin

- 6

- yl]

- 4,5,6,7

- tetrahydro

- 1H

- isoindole

- 1,3(2H)

- dioneFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 23 of 24 Common name Chemical name Chemical structure

3

- OH

- Flumioxazin 7

- fluoro

- 6

- (3

- hydroxy

- 3,4,5,6

- tetrahydrophthalimido)

- 4

- (2

- propynyl)

- 2H

- 1,4

- benzoxazin

- 3(4H)

- one

4

- OH

- Flumioxazin 7

- fluoro

- 6

- (4

- hydroxy

- 3,4,5,6

- tetrahydrophthalimido)

- 4

- (2

- propynyl)

- 2H

- 1,4

- benzoxazin

- 3(4H)

- one

Metabolite B , F Not available

Metabolite C Not available

4

- OH

- S

- 53482

- SA 7

- fluoro

- 6

- (1

- sulfo

- 4

- hydroxy

- 1,2

- cyclohexanedicarboximido)

- 4

- (2

- propynyl)

- 2H

- 1,4

- benzoxazin

- 3(4H)

-

oneFlumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406 070



### Page 24 of 24 Common name Chemical name Chemical structure

482

- HA N

- (7

- fluoro

- 3,4

- dihdyro

- 3

- oxo

- 4

- prop

- 2

- ynyl

- 2H

- 1,4

- benzoxazin

- 6

- yl)cyclohex

- 1

- ene

- 1

- carboxamide

- 2

- carboxylic acid

APF 3

- oxo

- 4

- prop

- 2ynyl

- 6

- amino

- 7

- fluoro

3,4

- dihydro

- 1,4

- benzoxazin

Metabolite B, C, & F structures are not fully characterized (with Metabolite B & Metabolite F associated with Goat milk, liver, & kidney; and Metabolite C associated with Goat milk, kidney, and muscle).