UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

MEMORANDUM 

DATE: December 19, 2012 

OFFICE OF CHEMICAL SAFETY AND 

POLLUTION PREVENTION 

SUBJECT: Flumioxazin. Petition for the Section 3 Registration and Establishment of 

Tolerances for uses on Artichoke, Cabbage, Olive, Pomegranate, and Prickly Pear 

Cactus. Summary of Analytical Chemistry and Residue Chemistry Data. 

PC Code: 129034 

Decision No.: 450810 

Petition: #1F7886 

Risk Assessment Type: Single 

Chemical Aggregate 

TXRNo.: NA 

MRID Nos.: 48730701-48730705 

DP Barcode: D406070 

Registration No.: 59639-97 

Regulatory Action: Section 3 

Registration 

Case No.: 7244 

CAS No.: 103361-09-7 

40 CFR: §180.568 

FROM: 

Risk 

Sheila 

Assessment 

Piper, Chemist 

Branch 

~ VI ~ 

Health Effects Division (7509P) 

THROUGH: Christine Olinger, Acting Branch Chief /J/ / _/ . Risk 

Health 

Assessment 

Effects Division 

Branch 

(7509

VI 

P) 

~~ 

TO: Andrew Ertman, Barbara Madden RM05 

Risk Integration, Minor Use, and Emergency Response Branch 

Registration Division (7505P) 
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Table of Contents

Contents

EXECUTIVE SUMMARY...........................................................................................................................................3

REGULATORY RECOMMENDATIONS ......................................................................................................................3

PRE-REGISTRATION DATA NEEDS......................................................................................................................................3

Analytical Methods....................................................................................................................................................4

RECOMMENDED TOLERANCES ..........................................................................................................................................4

INTERNATIONAL HARMONIZATION.....................................................................................................................................5

REVISIONS TO PETITIONED-FOR TOLERANCES ......................................................................................................................5

RESIDUE PROFILE ...........................................................................................................................................................5

RESIDUE CHEMISTRY GUIDELINES..........................................................................................................................6

DIRECTIONS FOR USE (860.1200)....................................................................................................................................6

860.1340 RESIDUE ANALYTICAL METHODS ......................................................................................................................8

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

Enforcement method in animal matrices ..................................................................................................................9

860.1360 MULTIRESIDUE METHODS...............................................................................................................................9

860.1380 STORAGE STABILITY .......................................................................................................................................9

860.1460 FOOD HANDLING ESTABLISHMENTS ................................................................................................................10

860.1480 MEAT, MILK, POULTRY, AND EGGS.................................................................................................................10

860.1500 CROP FIELD TRIALS ......................................................................................................................................11

860.1520 PROCESSED FOOD AND FEED .........................................................................................................................16

TOLERANCE DERIVATION..................................................................................................................................... 17

APPENDIX 1. FIELD TRIAL DATA AND OECD MRL CALCULATOR OUTPUT ............................................................. 20

APPENDIX 3. NOMENCLATURE AND STRUCTURES OF IMPORTANT METABOLITES AND DEGRADATES FOUND IN 

METABOLISM STUDIES IN PRIMARY CROPS AND LIVESTOCK. .............................................................................. 22

The DER was originally prepared by California Department of Pesticide Regulation (1001 I 

Street, Sacramento, CA 95812; submitted 07/16/12). The DER has been reviewed by the Health 

Effects Division (HED) and revised to reflect current Office of Pesticide Programs (OPP) 

policies.
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Executive Summary

Flumioxazin belongs to the N-phenylphthalimide class of herbicides (Group 14). It is a lightdependent peroxidizing 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 postemergence 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 permanent tolerances of flumioxazin on 

artichoke, cabbage, olive, pomegranate, and prickly pear cactus. The end-use products being 

proposed for use on these sites are Valor Herbicide (EPA Reg. No. 59639-99) 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 0.38 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 intervals (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-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. Flumioxazin tolerances are established under 40 CFR §180.568 and 

range from 0.02 to 8.0 ppm on a wide 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 

evaluation/enforcement and human health risk assessment.

Regulatory Recommendations

Provided the submitted Section F, there are no residue chemistry issues that would preclude 

granting the requested Section 3 registration for flumioxazin 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.
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Analytical Methods

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 

Flumioxazin 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 (LOD) and limit 

of quantitation (LOQ) for flumioxazin are 0.010 and 0.020 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 purified by partitioning 

between hexane/acetonitrile (ACN). The residues in the ACN phase were then concentrated, redissolved 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 Methods - 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 

PAM, Vol. I. 

Recommended Tolerances

HED recommends that CFR 40§180.568[a] be amended by establishing tolerances for the plant 

commodities listed in the Table 1. The tolerances should be defined as follows:

Tolerances are established for residues of the herbicide flumioxazin, including its metabolites 

and degradates, in or on the commodities in the table below. Compliance with the tolerance 

levels for flumioxazin is to be determined by measuring only 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.

Table 1. Tolerance Summary for Flumioxazin

Commodity Proposed 

Tolerance 

(ppm)

HED

Recommended 

Tolerance (ppm)

Comments (correct 

commodity definition)

Artichoke 0.02 0.02

Cabbage 0.02 0.02

Chinese Cabbage 0.02 0.02

Olive 0.02 0.02

Pomegranate 0.02 0.02

Prickly pear cactus, fruit 0.1 0.07
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Table 1. Tolerance Summary for Flumioxazin

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 required 

at this time since there is no reasonable expectation of finite residues.

Revisions to Petitioned-For Tolerances

The proposed tolerances are different for cactus from those 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 nomenclature and physiochemical properties of flumioxazin are presented below in Tables 2 

and 3. The chemical names and structures of flumioxazin 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-2H-1,4-benzoxazin-6-

yl)cyclohex-1-ene-1,2-dicarboxamide

CAS name 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-

4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

CAS # 103361-09-7

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

TABLE 3. Physicochemical Properties of the Technical Grade Test Compound

Parameter Value Reference

N

N

O

F

C

H2

O

O

HC C O
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TABLE 3. Physicochemical Properties of the Technical Grade Test Compound

Parameter Value Reference

Melting point/range 202–204°C US EPA Fact Sheet 

pH (25°C) 7.29 issued April 12, 2001.

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

Vapor pressure (22°C) 2.41 x 10-6 mmHg US EPA Fact Sheet 

Dissociation constant (pK issued April 12, 2001. a) None

Octanol/water partition 

coefficient Log(KOW)

2.55 at 20°C

UV/visible absorption spectrum λ218

λ216

λ216

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 products

being proposed for use on these sites are Valor Herbicide (EPA Reg. No. 59639-99) 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 0.38 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 flumioxazin is summarized in Table 4, below.

Table 4. Summary of Directions for Proposed Uses 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. Do 
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Table 4. Summary of Directions for Proposed Uses 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 crop 

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 DP# 272652, 3/12/01, R. Loranger

Residue Chemistry Memo DP# 259493, 3/12/01, D. Dotson 

Adequate plant metabolism studies are available depicting the uptake and metabolism of 

[

14C]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). 
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Conclusions: 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 DP# 272652, 3/12/01, R. Loranger

Residue Chemistry Memo DP# 259493, 3/12/01, D. Dotson 

Residue Chemistry Memo DP# 194594, 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 Analytical 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 has 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 

Phosphorous 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 partitioning 

between hexane/acetonitrile (ACN). The residues in the ACN phase were then concentrated, redissolved 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. 
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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 method in animal 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 

adequately 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/2001, D. Dotson

Residue Chemistry Memo DP# 397086, 22/FEB/2012, W.T. Drew

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 limits 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 Multiresidue Protocols were submitted 

and the available 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)
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Storage stability data for flumioxazin residues in various plant commodities are conducted in 

conjunction with the residue study on flumioxazin. Residues were stable in/on artichoke when 

stored frozen for 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, pomegranate, 

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. Storage 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 

Temperaturea

(°C)

Actual Storage Duration (days)1Interval of Demonstrated Storage Stability 

(days)

Crop Field Trial Studies

Artichoke

-21+7

o

221-225 days (7.3-7.4 months) 252 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

oC upon receipt at the laboratory. Durng processing 

for analysis, samples were moved and held temporarily (<1 day) in a freezer at -11+11oC. While outside the freezer 

they were maintained on dry ice. Ground samples were then returned to frozen storage at -21+7

oC.

860.1400 Water, 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 tolerances are not required for animal

commodities. 
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860.1500 Crop Field Trials

DER References: 48730701.DER (Artichoke)

48730702.DER (Cabbage)

48730703.DER (Olives)

48730704.DER (Pomegranate)

48730705.DER (Prickly Pear Cactus)

Crop field trials were conducted with artichoke, cabbage, olive, pomegranate, and prickly pear 

cactus following application of ValorTM Herbicide (51% water dispersible granule (WDG) to 

control broadleaf weeds.

Artichoke

The Interregional Research Project No. 4 (IR-4) has 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 

include 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 detection (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 samples 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 method 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)

PHI1

(days)

Residue Levels

(ppm)

n Min. Max. HAFT1 Median Mean Std. 

Dev.

Artichoke 0.187–0.191 126-

147

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

1HAFT = Highest Average Field Trial
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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 stability 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 0.02 ppm for artichoke. 

Cabbage

The Interregional Research Project No. 4 (IR-4) has submitted field trial data for flumioxazin on 

cabbage. Eight field trials were conducted in the United States during the 2006 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 Method entitled, “Residue 

Analysis of Flumioxazin on Cabbage by GC/NPD, Version #8.” This method was adapted with 

minor modifications from Valent method RM-30A-1. For method validation, 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 samples was 0.02 ppm. The LOD and LOQ for flumioxazin residues 

in/on cabbage samples were 0.0063 ppm and 0.019 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 Rate
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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 stability 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 0.02 ppm 

for cabbage. 

Olive

The Interregional Research Project No. 4 (IR-4) has 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 at 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 orchard 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 method validation, 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 fortified 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 89 -103% (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 LOQ 

calculated for flumioxazin in/on olive and olive oil was 0.021 ppm and 0.017 ppm, respectively. 
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The results 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 0.02 ppm for olive.

Pomegranate

The Interregional Research Project No. 4 (IR-4) has 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 days at rates of 0.363-0.383 lb ai/A. The applications were 

made in spray volumes of 20-36 gal/A, and included an adjuvant in the spray mixture. 

Pomegranate RAC samples were harvested at commercial maturity, 57-59 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 Determination of Flumioxazin Residues in Crops”. For method 

validation, control samples of pomegranate were fortified with flumioxazin at 0.02 and 0.2 ppm. 

Recoveries from pomegranate were 89-101% (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 for 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 days 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 D406070

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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. HAFT1 Median Mean Std. 

Dev.

Pomegranate 0.73-0.76 57-59 6 <0.02 <0.02 <0.02 <0.02 <0.02 -

1HAFT = 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 study is supported by adequate 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 0.02 ppm for 

pomegranate.

Prickly Pear Cactus

The Interregional Research Project No. 4 (IR-4) has submitted field trial data for flumioxazin on 

prickly 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 0.380-0.392 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 in/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 were 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 validation 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 D406070

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The maximum residues were <0.02 ppm, 0.025ppm, 0.026 ppm, and 0.037 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. HAFT1 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)

1HAFT = 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 fruit 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 Processed Food and Feed

DER References: 48730703.DER (Olives)

The Interregional Research Project No. 4 (IR-4) has submitted a processing study on olives. In 

one trial conducted in CA, two broadcast exaggerated rate (5X) applications of flumioxazin were 

made to the 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 the 5X treated plot showed 

residues of flumioxazin that were each below LOQ <0.02 ppm. 
Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406070

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

flumioxazin using an acceptable method, and the study is supported by adequate 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 DP #259493, 3/12/01, D. Dotson

Residue Chemistry Memo DP #272652, 3/12/01, R. Loranger

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 confined 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 application 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 calculation 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 Appendix 1.

List of Appendix

Appendix 1. Field Trial Data and OECD MRL Calculator Output

Appendix 2. International Residue Limits

Appendix 3. Chemical Structures of Important Metabolites Identified in Metabolism Studies and 

 Analyzed in Field Trials and Livestock Feeding Studies

Bibliography
Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406070

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 Chemical 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#: None

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 - 44295057
Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406070

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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: 7/23/2004

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 Fruit (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, 47005107
Flumioxazin Summary of Analytical Chemistry and Residue Data Barcode D406070

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

Dated: 1/31/2008

MRID(s): 47184801

Appendix 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. The residue values in mg/kg listed in the tables in this 

attachment are the means of the two samples taken at each trial site. 

Table 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% 100% 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 0.020 0.020 0.020 0.020

Rounded MRL 0.02 0.02 0.02 0.02

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*
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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 0.037 0.026

Median residue 0.025 0.020

Mean 0.027 0.022

Standard deviation (SD) 0.007 0.003

Correction factor for 

censoring (CF) 0.833 0.833

- Highest residue 0.0237 0.026

- Mean + 4 SD 0.056 0.034

- CF x 3 Mean 0.066 0.054

Unrounded MRL 0.066 0.06

Rounded MRL 0.07 0.06

High uncertainty of 

MRL estimate due to 

small dataset

High uncertainty of 

MRL estimate due to 

small dataset

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

0.037 0.020

0.020*

0.020*

0.025

0.026

0.024

0.020

Appendix 2: International Residue Limits

Flumioxazin (129034; 08/31/2012)

Summary of US and International Tolerances and Maximum Residue Limits 
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Residue Definition:

US Canada Mexico2 Codex3

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)-2H-1,4-

benzoxazin-6-yl]-

4,5,6,7-tetrahydro-1Hisoindole-1,3(2H)-

dione

None

Commodity1 Tolerance (ppm) /Maximum Residue Limit (mg/kg)

US Canada Mexico2 Codex3

Artichoke 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 quantitation; 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 not been finalized by the CCPR and the CAC.

Appendix 3: Nomenclature and Structures of Important Metabolites and Degradates 

Found in Metabolism Studies in Primary Crops and Livestock.

Common name Chemical name Chemical structure

Flumioxazin 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-

propynyl)-2H-1,4-benzoxazin-6-yl]-

4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-

dione N

N

O

F

C

H2

O

O

HC C O
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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

O N

N

F O

O

O

OH

4-OH-Flumioxazin 7-fluoro-6-(4-hydroxy-3,4,5,6-

tetrahydrophthalimido)-4-(2-propynyl)-

2H-1,4-benzoxazin-3(4H)-one

O N

N

F O

O

O

OH

Metabolite B, F Not available

O N

N

F O

O

O

OH

Metabolite C Not available

OH

O N

N

F O

O H

O

HO

O N

N

F O

O

H O

OH

OH

or

4-OH-S-53482-SA 7-fluoro-6-(1-sulfo-4-hydroxy-1,2-

cyclohexanedicarboximido)-4-(2-

propynyl)-2H-1,4-benzoxazin-3(4H)-

one

O N

N

F O

O

O

SO3H

OH
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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

HO

O

O

N

H

O

N

O

F

CH

APF 3-oxo-4-prop-2ynyl-6-amino-7-fluoro3,4-dihydro-1,4-benzoxazin

O NH2

N

O

F

CH

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).