Document ID: EPA-HQ-OPP-2010-0122-0009
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2011-03-09T05:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF CHEMICAL SAFETY

	AND POLLUTION PREVENTION

  SEQ CHAPTER \h \r 1 MEMORANDUM

Date:  October 12, 2010

SUBJECT:	Fomesafen Sodium.  Petition for the Establishment of Tolerances
and Registration of New Uses on Pepper and Potato, and Response to Data
Gaps for Conditional Registration based on Submission of a Confined
Rotational Crop Metabolism Study.  Summary of Analytical Chemistry and
Residue Data. 

PC Code:  123802	DP Barcodes:  D373544 and D382067

Decision No.:  426814	Registration No.:  100-993

Petition Nos:  9F7563 (potato), 9F7667 (pepper)	Regulatory Action: 
Amended Section 3

Risk Assessment Type:  NA	Case No.:  NA

TXR No.:  NA	CAS No.:  72178-02-0

MRID No.:  See MRID Summary Table	40 CFR:  §180.433

	

FROM:	Alexandra LaMay, Biologist

		Christine Olinger, Chemist  SEQ CHAPTER \h \r 1 

		Risk Assessment Branch VII

		Health Effects Division (7509P)

THROUGH:	Michael S. Metzger, Chief

		Risk Assessment Branch VII

		Health Effects Division (7509P)

TO:		Michael Walsh, PM Team 23

		Herbicide Branch   SEQ CHAPTER \h \r 1   SEQ CHAPTER \h \r 1 

		Registration Division (7505P)

MRID Summary Table

MRID No.	Study Type	Comments

47941402	860.1500 Pepper Crop Field Trials	New DER; 47941402.de1.doc

	860.1380 Pepper Storage Stability Study	New DER; 47941402.de2.doc

47937602	860.1850 Confined Rotational Crop Study	New DER;
47937602.der.doc

Executive Summary

Fomesafen sodium is a contact broadleaf herbicide in the diphenylether
chemical class.  The herbicide acts through inhibition of the enzyme
protoporphyrinogen oxidase (PPO) in plants.  The active ingredient was
originally registered on 09/11/1987 by Zeneca Ag Products and was
transferred to Syngenta Crop Protection, Inc. on 02/23/2001.  Fomesafen
is currently registered for use on the crops cotton, dry beans, snap
beans, and soybeans.  It is applied to treat various broadleaf weeds,
annual grasses, perennial weeds and sedges. 

Syngenta has proposed, in PP#9F7563 and PP#9F7667, the establishment of
permanent tolerances for residues of fomesafen in/on the following raw
agricultural commodities:

Potato	0.025 ppm

Pepper	0.025 ppm

In support of the proposed tolerances and new crop uses, Syngenta has
submitted a magnitude of the residue study on pepper and a confined
rotational crop metabolism study.  Syngenta has previously submitted a
magnitude of the residue study on potatoes (also described in DP barcode
D365199 and D366116, 1/21/2010, C. Olinger).  This Summary Document
addresses the adequacy of the submitted residue chemistry data in
support of the proposed new uses on peppers as well as the adequacy of
the submitted residue chemistry of the confined rotation crop metabolism
study.

On peppers, Reflex® Herbicide is proposed for one broadcast preplant
non-incorporated preemergence application up to 7 days prior to
transplanting pepper seedlings at a maximum rate of 0.375 lb ae/A and a
60-day preharvest interval (PHI).  On potatoes, Reflex® Herbicide is
proposed for one broadcast preemergence application after planting but
before potato emergence at a maximum rate of 0.25 lb ae/A and a 70-day
PHI.

HED generally recommends that three metabolism studies on diverse crops
when a pesticide is to be used on several different commodities.  It was
previously concluded that the three previously-submitted metabolism
studies on tomatoes, soybeans and cotton were not sufficiently diverse
to define the nature of the residue in all crops.  Since no data on a
root crop had been provided that can be translated to the proposed use
on potatoes, a potato metabolism study, in which both the root and
tops/foliage were analyzed, was required to support the proposed use on
potatoes (D365199 and D366116, 1/21/2010, C. Olinger).  Syngenta has
submitted a confined rotational crop metabolism study as part of the
current submission, which HED has determined is adequate and is
acceptable to use to determine the nature of the residue in potato.  The
residue of concern in plants is fomesafen.

There are no livestock feedstuffs associated with the proposed use on
peppers (PP#9F7667).  The only livestock feedstuffs associated with the
proposed uses in PP#9F7563 are potato culls and processed waste. The
nature of the residue in ruminants is adequately understood.  At this
time no tolerances have been established on any livestock commodity in
association with the existing uses of fomesafen.  There is no reasonable
expectation of finite residues in livestock.  Therefore, no livestock
feeding studies are required to support the proposed/registered uses of
fomesafen sodium.  Syngenta should note that if additional uses are
proposed in the future which result in an increase in the dietary
burdens, livestock feeding studies may be required. 

Adequate residue analytical methods are available for the purpose of
tolerance enforcement.  Syngenta submitted a new high performance liquid
chromatography method with tandem mass spectrometry detection (LC/MS/MS)
method (GRM045.01A) as an enforcement method.  The method uses
extraction procedures similar to previous methods, SPE cleanup
procedures, and the final determination step by LC/MS/MS for analysis of
fomesafen residues.  The validated limit of quantitation (LOQ) of the
method is 0.02 ppm.  Method GRM045.01A was adequately validated at
fortification levels of 0.02 ppm and 0.2 ppm in snap beans, pinto beans
(dry bean), corn oil, cotton, undelinted seed and gin byproducts, and
soybean forage, hay, and aspirated grain fractions.  Methods for the
determination of fomesafen residues of concern in livestock commodities
are not required at this time.  

The requirements for multiresidue method testing data for fomesafen are
fulfilled.  FDA multiresidue methods are not suitable for determining
residues of fomesafen.  

Samples of raw and processed commodities of potatoes, which were
collected from the magnitude of the residue studies, were analyzed for
residues of fomesafen using a LC/MS/MS based on a liquid chromatography
with ultraviolet detection (HPLC/UV) method (GAM-RM-001/86).  The method
was adequately validated during concurrent analysis of samples.  The
lowest level of method validation (LLMV) was 0.025 ppm.  Samples of raw
commodities of pepper, which were collected from the magnitude of the
residue studies, were analyzed for residues of fomesafen using a
HPLC/MS/MS method (TMR0626B).  The method was adequately validated
during concurrent analysis of samples.  The lowest level of method
validation (LLMV) was 0.025 ppm.

Analytical standards for fomesafen are currently available in the EPA
National Pesticide Standards Repository.

Adequate storage stability data are available to support the storage
conditions and durations of samples collected from the magnitude of the
residue studies on potato and pepper.  

The submitted field trial data for fomesafen on peppers and potatoes are
acceptable and support the proposed uses.  An adequate number of trials
were conducted in the appropriate geographic regions at ~1x the maximum
proposed rate using Reflex® Herbicide, and the appropriate samples were
collected from each test around the proposed PHI.  All treated samples
bore residues below the LLMV (<0.025 ppm).  Based on these data, HED
recommends a tolerance of 0.025 ppm for residues of fomesafen in/on
peppers and potatoes.

The results of submitted potato processing studies show that residues of
fomesafen were each below the LLMV (<0.025 ppm) in/on the respective
RACs following application of Reflex® Herbicide at 1x.  Since the
studies involved processing of RACs bearing nonquantifiable residues, no
measurable processing factors can be calculated.  Although, the Agency
would have preferred the use of exaggerated rates in the conduct of the
processing studies to yield RACs with quantifiable residues, HED will
not require additional processing data at this time.

Syngenta has submitted a new confined rotational crop study reflecting
separate application of CP- and NP-label fomesafen at the maximum
seasonal application rate to rotatable crops, including wheat, soybean,
potato, spinach, radish and carrot.  This has been completed and
reviewed by the Agency, and it has been determined that the nature of
the residue in rotational crops is adequately understood.  This confined
rotational crop data satisfies the data gap of the conditional
registrations of previous assessment (D365199 and D366116). 

There is now data to support rotation to other crops beyond those
commodities that are currently registered and proposed as primary crops.
 All plant back intervals (PBIs) for rotational crops on the draft label
are acceptable, including a 4 month PBI for wheat (and similar
commodities), a 10 month PBI for corn, peanuts, peas, rice, and seed
corn and an 18 month PBI for alfalfa, sunflowers, sugar beets and
sorghum.  

No Codex, Canadian, or Mexican MRLs have been established for residues
of fomesafen in/on potato or pepper; therefore, there are no issues with
international harmonization raised by this action.  Canadian MRLs have
been established for residues of fomesafen in/on dry beans, lima beans,
snap beans, and soybeans at 0.05 ppm, and a Mexican MRL of 0.05 mg/kg
has been established for residues of fomesafen in/on soybeans.  

  SEQ CHAPTER \h \r 1 Regulatory Recommendations 

HED has examined the residue chemistry database for fomesafen sodium. 
The deficiency pertaining to directions for use the submission of a
confined rotational crop study has been resolved; there are no residue
chemistry issues that would preclude granting the petitioner’s request
to amend the Reflex® Herbicide label for the purpose of adding the
requested use on potatoes and peppers.  HED recommends a registration
for this herbicide on the crops requested and/or the revision of 40 CFR
§180.433 for the establishment of tolerances for residues of fomesafen
as follows:

Potato	0.025 ppm

Pepper, bell 	0.025 ppm

Pepper, non-bell 	0.025 ppm

Also, the data gaps pertaining to the conditional registration on
tomatoes, dry bean, snap bean, and cotton has been resolved based on
submission of adequate confined rotational crop metabolism data. 

The registrant’s most recent Reflex® Herbicide label reflects
regional use of fomesafen on peppers.  However, the residue chemistry
data submitted in support of this action are of sufficient geographic
representation to support full U.S. registration; therefore, HED
recommends that these tolerances be listed in the general section of 40
CFR §180.433.

Tolerances for fomesafen residues are listed in 40 CFR §180.433. 
Currently, the single established tolerance is expressed in terms of
“sodium salt of fomesafen,
5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzam
ide.”  HED has determined that the residue of concern for tolerance
expression is fomesafen.  Therefore, the established tolerance
expression should be revised to be expressed in terms of fomesafen, by
removing the phrase “sodium salt of” from 40 CFR §180.433(a).

Note to PM:  According to HED’s Interim Guidance on Tolerance
Expressions (5/27/09, S. Knizner), the tolerance expression for
fomesafen should be revised to state:

“Tolerances are established for residues of fomesafen, including its
metabolites and degradates, in or on the commodities in the table below.
 Compliance with the tolerance levels specified below is to be
determined by measuring only fomesafen
[5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenza
mide].”

The current tolerances listed in 40 CFR §180.433 for fomesafen in
soybeans, dry beans, and snap (succulent) beans are 0.05 ppm.  HED
continues to recommend for the reduction of the following tolerances, as
described in a previous memo (D. Davis, DP No. D325801, 4/25/06):  dry
beans and snap (succulent) beans should be reduced to 0.025 ppm and the
tolerance on soybeans should be reduced to 0.02 ppm.  Note that the
lower tolerance values were used in the dietary risk assessment.

A human health risk assessment is forthcoming.

Residue Chemistry Deficiencies

Deficiencies - Tomato Petition (9F7563)

All data gaps previously identified by HED (DP# 365199 and 366116,
1/21/2010, C. Olinger) as a condition of registration under the
petitions cited above have now been adequately fulfilled.

The data gap of confined accumulation in crops identified in HED (DP#
365199 and 366116, 1/21/2010, C. Olinger) as a condition of registration
for the use on tomatoes has now been adequately fulfilled.  

There is now data to support rotation to other crops beyond those
commodities currently registered and primary crops.  The data supports a
4 month rotational interval to small grains; a 10 month rotational
interval to corn, peanuts, peas, rice and seed corn; and an 18 month
rotational interval to alfalfa, sunflowers, sugar beets, and sorghum. 

Remaining Deficiencies – PP#s 1E6228 (Dry Bean), 9F5068 (Cotton), and
6E4653 (Snap Bean) 

The data gap of the requirement for confined rotational crop data
previously identified by HED (DP# 365199 and 366116, 1/21/2010, C.
Olinger) as a condition of registration under the petitions cited above
have now been adequately fulfilled.   

There still remains the deficiency pertaining to storage stability
listed below.  

860.1380 Storage Stability

	·	The registrant intends to submit a final storage stability report,
including analyses at 18 and 24 months.  When this study is submitted
the registrant should ensure that the dates documented in the report
should reflect the actual storage intervals, and not the proposed
intervals, as there was some discrepancy in the interim report.

Background

The chemical name and structure of fomesafen sodium and fomesafen are
listed below in Table 1.  The physicochemical properties of fomesafen
are listed in Table 2; data pertaining to the physicochemical properties
of fomesafen sodium are not available.

5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-N-methylsulfonyl-2-nitrobenza
mide, sodium salt

CAS name
5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitro-benza
mide, sodium salt

CAS registry number	108731-70-0

Compound	

Common name	Fomesafen

Company experimental name	Not provided.

IUPAC name
5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-N-methylsulfonyl-2-nitrobenza
mide

CAS name
5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzam
ide

CAS registry number	72178-02-0

End-use product (EP)	Reflex® Herbicide, 2 lb ae/gal SL; EPA Reg. No.
100-993

Table 2.   Physicochemical Properties of Fomesafen.

Parameter	Value	Reference

Melting point/range	220-221 (C	HED Memo, 9/3/82, W. Anthony

pH	8.2 (94% TGAI)	CSF (EPA Reg. No. 100-1017; 10/13/00)

Density	1.28 g/cm3 at 20 (C	HED Memo, 9/10/86, C. Trichilo

Water solubility at 25 °C	600 g/L at pH 7

<10 ppm at pH 1-2

50 mg/L	HED Memo, 9/3/82, W. Anthony

HED Memo, 9/10/86, C. Trichilo

Solvent solubility	g/L

Acetone	                                300

Cyclohexanone	                150

Methanol	                                  25

Hexane	                                  0.5

Xylene                                      1.9	HED Memo, 9/10/86, C.
Trichilo

Vapor pressure	<7.5 x 10-7 mm Hg at 50 (C	The Pesticide Manual 1

Dissociation constant, pKa	2.7 at 20 (C

	Octanol/water partition coefficient, Log(KOW)	Log KOW = 2.9 at pH 1

	UV/visible absorption spectrum	Not available

	1  The Pesticide Manual, A World Compendium, The British Crop
Protection Council (toxnet.nlm.nih.gov).

860.1200 Directions for Use

The end-use product relevant to the pepper petition (PP#9F7667) and
potato petition (PP#9F7563)  is Reflex® Herbicide (EPA Reg. No.
100-993), a soluble concentrate liquid (SL) formulation containing 22.8%
sodium salt of fomesafen as the active ingredient (equivalent to 2 lb
ae/gal of fomesafen).  Reflex® is a selective herbicide which may be
applied preplant surface, preemergence, and/or postemergence for control
or partial control of broadleaf weeds, grasses, and sedges in registered
crops cotton, dry beans, snap beans, and soybeans.  In support of the
proposed use on peppers, the petitioner submitted a draft label for
Reflex® Herbicide dated 4/22/2010.  A summary of the proposed use
directions for potatoes and peppers is presented in Table 3A.

Table 3A.  Summary of Proposed Use Directions of Reflex® Herbicide (EPA
Reg. No. 100-993; 2 lb ae/gal) on Potatoes and Peppers.

Applic. Timing, Type, and Equip.	Applic. Rate 

(lb ae/A)	Max. No. Applic. per Season	Max. Seasonal Applic. Rate

(lb ae/A)	PHI

(days)	Use Directions and Limitations

Peppers (Transplanted)

Broadcast preplant non-incorporated preemergence application up to 7
days prior to transplanting peppers

Ground/Aerial/Center pivot irrigation	0.25-0.375	1	0.375	60	Refer to
Syngenta’s Regional Use Map for Reflex® 1 (summarized in the
‘General Use Directions’ below) for determination of maximum use
rate that may be applied in each geographic region.  Do not apply to any
field in Regions 2, 3, 4, or 5 more than once every two years.

Potato

Broadcast preemergence application after planting but before potato
emergence 

Ground/Aerial/Center pivot irrigation	0.25	1	0.25	70	Refer to
Syngenta’s Regional Use Map for Reflex® 1 (summarized in the
‘General Use Directions’ below) for determination of maximum use
rate that may be applied in each geographic region.  Do not apply to any
field in Regions 2, 3, 4, or 5 more than once every two years.  Do not
apply to sweet potatoes or yams.  Do not apply as a preplant
incorporated application as crop injury may occur.  Do not apply to
emerged potato plants or severe crop injury will occur.

1  The draft label specifies five use regions with specific seasonal
maximum application rates.  The rates range with the label use Region 1
having the highest seasonal application rate reflects application at
0.375 lb ae/A each year and label use Region 5 with the lowest seasonal
application rate reflects application of up to 0.1875 lb ae/A in
alternate years.  Details of the seasonal maximums for all label use
Regions are presented below under “General Use Directions”.

General Use Directions

Syngenta’s regional use map for Reflex®:  The draft label specifies
that product may only be used in the eastern half of the U.S. 
Syngenta’s regional use map for Reflex® is subdivided into the
following five regions:

Region 1:  Reflex® may be applied at a maximum of 0.375 lb ae/A per
year in Region 1 per year which includes the following states or portion
of states:  AL, AR, FL, GA, LA, MS, MO (counties of Bollinger, Butler,
Cape Girardeu, Dunklin, Madison, Mississippi, New Madrid, Pemiscot,
Perry, Ripley, Scott, Stoddard, and Wayne), NC, OK (East of U.S. Highway
75 and East of Indian Nation Parkway), SC, TN, and TX (includes area
East of U.S. Highway 77 to State Road 239 including all of Calhoun
County).

Region 2:  Reflex® may be applied at a maximum of 0.375 lb ae/A in
alternate years in Region 2 which includes the following states or
portion of states:  DE, KY, MD, VA, WV, and South of Interstate 70 in
the following states:  IL, IN, and OH and all areas South of the
Interstate 80 to the intersection of U.S. Highway 15 and East of U.S.
Highway 15 and U.S. Highway 522 in PA.

Region 3:  Reflex® may be applied at a maximum of 0.313 lb ae/A in
alternate years in Region 3 which includes the following states or
portion of states:  CT, IA, ME, MA, MO (all counties except those listed
in Region 1), NH, NJ, NY, PA (all areas except those listed in Region
2), RI, VT, and WI (South of U.S. Highway 18 between Prairie Du Chien
and Madison, and South of Interstate 94 between Madison and Milwaukee),
and North of Interstate 70 in the following states:  IN, IL, and OH. 

Region 4:  Reflex® may be applied at a maximum of 0.25 lb ae/A in
alternate years in Region 4 which includes the following states or
portion of states:  KS (all counties East of or intersected by U.S.
Highway 281), MI (Southern Peninsula), MN (all areas South of Interstate
94), NE (all counties East of or intersected by U.S. Highway 281), and
WI (all areas, except those in Region 3, South of Interstate 94 from MN
state line to Eau Claire and South of U.S. Highway from Eau Claire to
Green Bay plus Barron, Chippewa, Clark, Door, Dunn, Eau Claire,
Kewaunee, Marathon, Menominee, Oconto, Polk, Shawano, and St. Croix
counties.  The following counties are excluded:  Adams, Marquette,
Portage, Waupaca, Waushara, and Wood).  ND (all areas East of Interstate
29 from Fargo South to the SD state line).  SD (all areas East of
Interstate 29 from the ND state line to Watertown, all areas East of
Highway 81 from Watertown to Madison and all areas East and South of
State Road 34 and U.S. Highway 281 to the NE state line.

Region 5:  Reflex® may be applied at a maximum of 0.1875 lb ae/A in
alternate years in Region 5 which includes the following states or
portion of states:  ND (all areas East of the U.S. Highway 281 except
those areas in Region 4), SD (all areas East of the U.S. Highway 281
except those areas in Region 4), and MN (all areas South of the U.S.
Highway 2 except those areas in Region 4).

Spray additives:  The draft label specifies that spray additives cleared
for use on growing crops under 40 CFR §180.1001 may be used in the
spray mixture.  A nonionic surfactant (NIS), crop oil concentrates
(COC), or other adjuvants may be used for postemergence applications
only.  Since the proposed uses on potatoes and peppers are either
preemergence or pretransplant, the use of surfactants is typically not
needed when Reflex® is applied to these crops, as the label states
adjuvants are not needed for preplant surface or preemergence
applications unless Reflex® is being used in a burndown on emerged
weeds.  

Application equipment:  Ground applications are to be made in a minimum
of 10 gal/A, and aerial applications are to be made in a minimum of 5
gal/A.  Applications are not to be made through any type of irrigation
equipment except center pivot systems.  Reflex® alone or in tank
mixture with other herbicides on the label, which are registered for
center pivot application, may be applied in irrigation water
preemergence (after planting but before weeds or crop emerge) at
label-recommended rates.

Tank mixtures with other products registered for use on potatoes and
peppers:  The draft label provides mixing procedures for tank mixes but
does not specify specific tank mix partners for potatoes and peppers. 
The use directions state that, for tank mix combinations, the
recommendations, restrictions, and limitations for all products must be
followed and that the most restrictive labeling is to apply.  For
preemergence application in potatoes, Reflex® may be tank mixed with
other pesticide products registered for use in this way and timing in
potatoes.  For preplant non-incorporated preemergence applications prior
to transplanting peppers, Reflex® may also be tank mixed with other
pesticide products registered for use in this way and timing in peppers.
 

Rotational crop plantback intervals:  The draft label specifies that the
rotational crops listed in Table 3B may be planted after applying
Reflex® at recommended rates.

Table 3B.  Rotational Crop Plantback Intervals Listed on the Reflex®
Herbicide.

Crop To Be Planted	Minimum Rotation Interval

(Days or Months After Last Reflex® Application)

Cotton, dry beans, peppers, potatoes, snap bean, soybeans, and
transplanted tomatoes	0

Small grains such as wheat, barley, and rye	4 months

Corn 1, peanuts, peas, rice, seed corn	10 months

To avoid crop injury, do not plant alfalfa, sunflowers, sugar beet,
sorghum 2, or any crop within	18 months

Do not graze rotated small grain crops or harvest forage or straw for
livestock.

1 Use a 12 month minimum rotation interval for popcorn in the states of
OH, KY, IL, IN, IA, and Region 4 when applied at rates of 0.25 lb ae/A
or more.  Use 18 month minimum rotation for sweet corn in the states of
CT, ME, MA, NH, NY, RI, VT, and Region 5.

2  Sorghum may be planted back after 10 months in Region 1.

Conclusions.  The available draft label for Reflex® Herbicide is
adequate to allow evaluation of residue data relative to the proposed
use on potatoes and peppers. 

The available draft label and available data are adequate to evaluate
rotation to other crops beyond those commodities that are currently
registered and proposed as primary crops.

860.1300 Nature of the Residue - Plants

DER Reference: 	47473901.der.doc (tomato)

DER Reference: 	44754706.der.wpd (cotton)

DER Reference: 	45313001.der.wpd (soybean)

Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis

Residue Chemistry Memo DP#365199 and 366116, 1/21/2010, C. Olinger

Currently adequate tomato, soybean, and cotton metabolism studies are
available for fomesafen, but no metabolism studies are available for a
root crop.  In a meeting with HED in 2008, the registrant proposed
substituting the results of a confined rotational crop study for the
root/tuber metabolism study, since the use is early season, is used in
manner similar to the applications employed in a rotational study, and
the use is not likely to result in detectable residues.  However, the
confined study had not been submitted when HED had reviewed the petition
on potatoes (DP#365199 and 366116, 1/21/2010, C. Olinger).  Syngenta has
since submitted a confined rotational crop metabolism study for the
rotational crops of wheat, soybean, potato, spinach, radish, and carrot
(see section 860.1850).  No new metabolites of concern relevant to
root/tuber vegetables were identified in the study.  HED has concluded
this study is adequate to support the tolerance in/on potatoes.  The
residue of concern in/on potatoes and peppers is fomesafen.

860.1300 Nature of the Residue - Livestock

MRID 00110508 (PP#2G2745, 1/28/83, A. Rathman, and PP#4F2997, 9/25/94,
A. Smith)

MRID 00135635 (PP#4F2997, 9/25/84, A. Smith)

Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis

Residue Chemistry Memo DP#365199 and 366116, 1/21/2010, C. Olinger

Syngenta submitted a goat metabolism study in conjunction with the
temporary tolerance petition for soybeans (PP#2G2745).  A single goat
was dosed with [nitrophenyl-14C]fomesafen at 0.1 ppm in the diet for 7
days; the goat was sacrificed 16 hours after the final dose.  The dosing
level corresponds to ~2x and 5x the maximum theoretical dietary burdens
to beef and dairy cattle, respectively.  TRR reached a maximum in milk
of 0.0008 ppm on Day 3.  TRR were 0.003 ppm in liver, 0.004 ppm in
kidney, <0.003 ppm in meat, and <0.005 ppm in fat.  Approximately 70% of
the dosed radioactivity was excreted.  No residue characterization was
conducted because of low radioactivity levels.  

A goat metabolism study was reviewed in conjunction with the soybean
permanent tolerance petition (PP#4F2997).  A single goat was dosed with
[nitrophenyl-14C]fomesafen at 10.3 ppm in the diet for 3 consecutive
days; the goat was sacrificed 4 hours after the final dose.  The dosing
level corresponds to ~184x and 468x the maximum theoretical dietary
burdens to beef and dairy cattle, respectively.  TRR were 0.20 ppm in
liver, 0.28 ppm in kidney, 0.009 ppm in meat, 0.006 ppm in fat, and
0.014 ppm in milk.  Approximately 47% of the dosed radioactivity was
excreted.  Fomesafen was not found in any milk, tissue, or excreta
sample.  The identified metabolites were
5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-N-methylsulfonylanthranilamid
e (compound XV) and 5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)
anthranilic acid (compound V).  Compound XV was found at 10% TRR in
liver and 20.9% TRR in kidney, and compound V was found at 34.5% TRR in
liver and 33.9% TRR in kidney.  

Conclusions.  The available livestock metabolism data are adequate to
satisfy data requirements. The significant components of the animal
residues are fomesafen and its metabolites
5-(2-chloro-α,α,α-trifluoro-p-tolyloxy) anthranilic acid (compound V)
and
5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-N-methylsulfonylanthranilamid
e (compound XV).  

Based on the residue levels in goat matrices following dosing at to
~184x and 468x the maximum theoretical dietary burdens to beef and dairy
cattle, respectively, HED concludes that the proposed/registered uses of
fomesafen on cotton, dry and snap beans, soybeans, potatoes, peppers and
tomatoes result in a 40 CFR §180.6(a)(3) situation for livestock
commodities; i.e., there is no reasonable expectation of finite residues
in livestock commodities.  There are no poultry and swine feedstuffs
associated with the proposed uses.

860.1340 Residue Analytical Methods

MRIDs 47761903 and 47761904 (Enforcement method GRM045.01A; DP# 365199
and 366116, 1/21/2010, C. Olinger)

Plant commodities

Enforcement methods

Syngenta Crop Protection has previously submitted descriptions and
validation data for the enforcement method, Method GRM045.01A, which is
entitled “Fomesafen Analytical Method for the Determination of
Residues of Fomesafen in Crop Commodities by LC-MS/MS.”  This high
performance liquid chromatography with tandem mass spectrometry
detection (LC/MS/MS) method is based on previously submitted gas
chromatography with nitrogen phosphorus detection (GC/NPD) methods
(refer to DP# 325801, D. Davis, 4/25/06) developed by Zeneca AG.  This
method is the updated version for previous Zeneca AG data-gathering
methods (TMR08055B, TMR0879B, TMR0800B, and TMR0881B).  

Method GRM045.01A uses extraction procedures modified from the previous
GC/NPD methods.  In the revised method, fomesafen residues are extracted
with 1% hydrochloric acid in acetonitrile.  An aliquot is subjected to
an SPE cleanup and analyzed using LC/MS/MS.  A second ion transition may
be monitored for confirmation.  The validated LOQ is 0.02 ppm for
fomesafen in each matrix.  Representative spectra and linearity data
were submitted demonstrating adequate sensitivity.  Method GRM045.01A
has been adequately validated at fortification levels of 0.02 ppm and
0.2 ppm in snap beans, pinto beans (dry bean), corn oil, cotton,
undelinted seed and gin byproducts, and soybean forage, hay, and
aspirated grain fractions.  This method is adequate for enforcement
purposes.

Data-collection methods

Samples of raw and processed commodities of potatoes, which were
collected from the magnitude of the residue study, were analyzed for
residues of fomesafen using a high performance liquid chromatography
method with tandem mass spectrometry detection based on an HPLC/UV
method (GAM-RM-001/86).  The method was adequately validated during
concurrent analysis of samples.  The lowest level of method of
validation (LLMV) was 0.025 ppm for each matrix. 

Samples of raw pepper, which were collected from the magnitude of the
residue study, were analyzed for residues of fomesafen using an ultra
performance liquid chromatography method with quadrupole mass
spectrometry detection (TMR0626B) based on a GC/NPD method.  This method
is similar to the enforcement method; this method has a similar
extraction method (fomesafen residues are extracted with 1% hydrochloric
acid in acetonitrile), no SPE cleanup step, a similar analysis method
(done by HPLC/MS/MS), and a different confirmation ion.  The method
validation percent recovery ranged from 83-118%, which is within
70-120%.  The method was adequately validated during concurrent analysis
of samples, with percent recovery ranging from 84-117%.  The LLMV was
0.025 ppm for peppers.

Livestock commodities

Because there are no established or proposed tolerances for livestock
commodities, an enforcement method for livestock commodities is not
required.

860.1360 Multiresidue Methods

DER Reference List:  47761901.der.doc

Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis

HED (DP# 325801) previously required the submission of multiresidue
method testing data for fomesafen.  In response, the petitioner
submitted MRID 47761901.  The submission has been reviewed by HED, and
the Executive Summary of the study DER is reproduced below.

Syngenta Crop Protection has submitted multiresidue testing data for
fomesafen (free acid) following testing and analysis according to FDA
Multiresidue Test Guidelines in PAM Vol. I (1/94).  The Decision Tree
for MRM Testing found in the Multiresidue Protocols was followed in
determining the response patterns.  Fomesafen (free acid) was tested
through Protocols A, B, and C.  Protocols D, E, and F were not tested as
no residues were detected using Protocol C.  The compound was not tested
under Protocol G because it is not a substituted urea.

  

Fomesafen does not have an N-methylcarbamate structure and did not
produce a response on the fluorescence detector under Protocol A.  In
Protocol B testing, methylated fomesafen was not recovered from
Florisil; therefore, no additional work was performed under Protocol B.

Fomesafen (free acid) did not produce a response under Protocol C, using
gas chromatography with either the nitrogen phosphorus or the electron
capture detector (GC/NPD or GC/ECD).  Therefore, it was not tested using
Protocol D, E, or F.

Conclusions:  These data indicate that FDA multiresidue methods are not
suitable for determining residues of fomesafen.  The submitted data will
be forwarded to U.S. FDA for further evaluation.

860.1380 Storage Stability

DER Reference:  47761902.der.doc (corn, soybean, cotton, and wheat
matrices storage stability data)

DER Reference:  47473903.de1.doc (potato tuber concurrent storage
stability data)

DER Reference:  47473903.de2.doc (potato processed commodities
concurrent storage stability data)

DER Reference:  47473902.de1.doc (tomato fruit concurrent storage
stability data)

DER Reference:  47473902.de2.doc (tomato processed commodities
concurrent storage stability data)

DER Reference:  47941402.de2.doc (pepper fruit concurrent storage
stability data)

Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis

Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger

Sample storage duration and conditions  

The storage durations and conditions of potato samples from the
submitted magnitude of the residue and processing studies are presented
in Table 4; the storage durations and conditions of pepper samples from
the submitted magnitude of the residue study are presented in Table 4. 
Table 4 also includes the storage conditions and durations of samples
from the crop field trial, processing, and field rotational crop studies
which were submitted to support previous petitions (PP#s 1E6228, 9F5068,
6E4653, and 9F7563).

Table 4.   Summary of Storage Conditions and Durations of Samples from
Crop Field Trial, Processing, and Field Rotational Crop Studies. 

Matrix	Storage Temperature  (°C)	Actual Storage Duration	Interval of
Demonstrated Storage Stability

Samples from Previous Petitions (PP#s 1E6228, 9F5068, and 6E4653)

reviewed under DP# 325801, 4/25/06, D. Davis

Cotton Field Trials (MRID 44754701)

Cotton gin byproducts	~-18	232-324 days

(7.6-10.7 months)	Storage stability data indicate that residues of
fomesafen appear to be erratic in/on cotton gin byproducts, but overall
show general stability; corrected stored recoveries were 69% at 2.5
months, 80% at 3.2 months, 142% at 8.8 months, and 68% at 14.6 months.

Soybean Processing Study (MRID 45093601)

Soybean hulls	-20	294 days

(9.7 months)	Storage stability data indicate that residues of fomesafen
appear to be relatively stable in/on soybean hulls stored frozen at -31
to -3 ºC for up to ~15 months.

Soybean refined oil

288 days

(9.5 months)	Storage stability data indicate that residues of fomesafen
appear to be relatively stable in/on soybean oil for up to ~9 months but
increased to a recovery of 149% by ~15 months.

Field Rotational Crop Study (MRID 00158936)1

Corn forage	-20	235-272 days

(7.7-8.9 months)	Storage stability data indicate that residues of
fomesafen appear to be relatively stable in/on corn K+CWHR, forage, and
stover, and wheat forage and straw stored frozen at -31 to -3 ºC for up
to ~15 months.

Corn cob

178-223 days

(5.8-7.3 months)

	Corn fodder

178-223 days

(5.8-7.3 months)

	Wheat forage

361-388 days

(11.9-12.7 months)

	Wheat straw

289-339 days

(9.5-11.1 months)

	Field Rotational Crop Study (MRID 45268501)

Field corn, forage	<-10	280-316 days

(9.2-10.4 months)	Storage stability data indicate that residues of
fomesafen appear to be relatively stable in/on corn forage and stover,
and wheat forage and straw stored frozen at -31 to -3 ºC for up to ~15
months.

Field corn, stover

239-279 days

(7.9-9.2 months)

	Sorghum, forage

232-289 days

(7.6-9.5 months)

	Sorghum, stover

182-273 days

(6.0-9.0 months)

	Samples from Previous Petition (PP#9F7563)

reviewed under DP# 365199 and 366116, 1/21/2010, C. Olinger

Potato Field Trials and Processing Study (MRID 47473903)

Potato tuber	-40 to -6	316-399 days

(10.4-13.1 months)	Concurrent storage stability data indicate that
residues of fomesafen appear to be relatively stable for up to 420 days
in/on frozen potato tuber, 311 days in potato flakes, 308 days in potato
chips, and 307 days in wet potato peel. 

Potato, tuber (RAC)	-40 to -6	308 days

(10.1 months)

	Potato, flakes

299 days

(9.8 months)

	Potato, chips

298 days

(9.8 months)

	Potato, wet peel

293 days

(9.6 months)

	Tomato Field Trials and Processing Study (MRID 47473902)

Tomato fruit	-40 to -5	211-302 days

(6.9-9.9 months)	Concurrent storage stability data indicate that
residues of fomesafen appear to be relatively stable for up to 319 days
in/on tomato fruit and 236 days in tomato paste and puree.

Tomato, fruit (RAC)	-40 to -5	241 days

(7.9 months)

	Tomato, paste

229 days

(7.5 months)

	Tomato, puree

229 days

(7.5 months)

	Samples from Current Petition (PP#9F7667)

Pepper Field Trials (MRID 47941402)

Pepper fruit	-29 to -15	458 days

(15.1 months)	Concurrent storage stability data indicate that residues
of fomesafen appear to be relatively stable for up to 458 days in/on
pepper fruit.

1  For the field rotational crop study reported in MRID 00158936, the
dates of sample analysis were not provided.  The maximum storage
interval for each sample, based on the study completion date, was
calculated by the study reviewer.

Storage stability data

Storage stability data were concurrently generated with the potato field
and processing studies.  For each crop, control samples of the
respective matrices were fortified with fomesafen at ~0.25 ppm and
placed in storage under the same frozen conditions as the treated
samples.  No zero-day analyses were conducted on the fortified samples
placed into storage.  Rather, triplicate stored samples were analyzed
along with a control sample and freshly fortified samples at an interval
reflecting the maximum storage intervals from the field and processing
studies.  Average corrected recovery ranges of fomesafen were:  78-90%
in potato tubers after 420 days, 79-99% in potato flakes after 311 days,
72-77% in potato chips after 308 days, and 71-81% in potato wet peel
after 307 days.  Although no 0-day analysis was conducted, the data
indicate that fomesafen is stable under frozen storage conditions at the
maximum intervals tested.  These data indicate that no corrections of
residues need to be applied to the study results.

Storage stability data were concurrently generated with the pepper field
study.  Control samples were fortified with fomesafen at ~0.25 ppm and
places in storage under the same frozen storage conditions as the
treated samples.  Triplicate stored samples were analyzed along with a
control sample and freshly fortified sample at an interval reflecting
the maximum storage intervals from the field study.  Recovery ranges of
fomesafen were 92-119% in pepper fruit after 458 days.  These data
indicate that fomesafen is stable under frozen storage conditions at the
maximum interval tested.  These data indicate that no corrections of
residues need to be applied to the study results.

860.1400 Water, Fish, and Irrigated Crops

There are no proposed uses that are relevant to this guideline topic.

860.1460 Food Handling

There are no proposed uses that are relevant to this guideline topic.

860.1480 Meat, Milk, Poultry, and Eggs

There are no livestock feedstuffs associated with the proposed use on
peppers (PP#9F7667).  

The only livestock feedstuffs associated with the proposed uses in
PP#9F7563 are potato culls and processed waste.  The dietary burdens of
fomesafen to beef and dairy cattle resulting from the proposed use on
potato and the registered uses on cotton, dry and snap beans, and
soybean, are presented in Table 5.  The dietary burdens were calculated
according to the Agency guidance on constructing maximum reasonably
balanced diets (June 30, 2008) and used the proposed and existing
tolerances for feedstuffs.  The calculated dietary burdens are 0.054 ppm
for beef cattle and 0.019 ppm for dairy cattle.  There are no poultry
and swine feedstuffs associated with the proposed uses.  

Table 5.    Livestock Dietary Burdens for Fomesafen.

Feedstuff	Feedstuff Type1	% Dry Matter 2	% Diet 2	Estimated Tolerance
Dietary Contribution (ppm) 3

Beef Cattle

Cotton hulls	R	90	10	0.025 ppm	0.003

R not registered4	R	--	5	--	--

Potato processed waste	CC	15	30	0.025 ppm for potato	0.050

CC not registered/ reasonable4	CC	--	50	--	--

Soybean, meal5	PC	92	5	0.02 ppm	0.001

  TOTAL BURDEN

	100

0.054

Dairy Cattle

R not registered	R	--	45	--	--

Potato processed waste	CC	15	10	0.025 ppm for potato	0.017

CC not registered4	CC	--	35	--	--

Soybean, meal5	PC	92	10	0.02 ppm	0.002

  TOTAL BURDEN

	100

0.019

1  R = Roughage; CC = Carbohydrate concentrate; and PC = Protein
concentrate.

2  Table 1 Feedstuffs (June 2008).  

3  Contribution = (tolerance /% DM x % in diet) for beef and dairy
cattle.

4  Although fomesafen is registered for other feedstuffs not listed in
the dietary burden, only the feedstuffs which will result in the maximum
dietary contribution were included.  The calculation follows the
guidance on constructing maximum reasonably balanced diets (June 30,
2008).

5 Currently, soybean tolerance is established at 0.05 ppm.  HED has
since recommended that the tolerance on soybean be reduced to 0.02 ppm
(D. Davis, DP No. D325801, 4/25/06).  HED continues to recommend that
these tolerances be updated.

A ruminant feeding study was not submitted and is not needed for the
purpose of this petition.  HED concludes that the registered uses of
fomesafen on cotton, dry and snap beans, and soybean and the proposed
use of fomesafen on potato result in a 40 CFR §180.6(a)(3) situation
for livestock commodities; there is no reasonable expectation of finite
residues in livestock.  Therefore, no livestock feeding studies are
required to support the proposed/registered uses of fomesafen sodium. 
Syngenta should note that if additional uses are proposed in the future
which result in an increase in the dietary burden, livestock feeding
studies may be required.

860.1500 Crop Field Trials

DER Reference List	47473903.de1 (Potato)

			Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger

			47941402.der (Pepper)

A summary of the reviewed crop field trial data for potato and pepper is
presented in Table 6.

Table 6.   Summary of Residue Data from Crop Field Trials with
Fomesafen.

Commodity	Total Applic. Rate

 (lb ae/A)	PHI (days)	Residue Levels  (ppm)

	n	Min.	Max.	HAFT1	Median

(STMdR)	Mean

(STMR)	Std. Dev.

Potato

(Proposed use = One preemergence application after planting but before
crop emergence at 0.25 lb ae/A; 

70-day PHI)

Potato tubers	0.237-0.263	70-141	26	<0.025	<0.025	<0.025	0.025	0.025	---

Pepper

(Proposed use = One preplant non-incorporated preemergence application
up to 7 days prior to transplanting of peppers at 0.375 lb ae/A; 60 day
PHI)

Pepper fruit	0.362-0.385	59-121	26	<0.025	<0.025	<0.025	0.025	0.025	---

1  HAFT = Highest Average Field Trial.

Potato

  SEQ CHAPTER \h \r 1 Syngenta Crop Protection has submitted field trial
data for fomesafen on potatoes.  Thirteen trials were conducted in the
United States in Zones 1 (NY; 1 trial), 2 (MD, NC and NJ; 3 trials), 3
(FL; 1 trial), 5 (MI and WI; 2 trials), 8 (CO; 2 trials), and 11 (ID and
WA; 4 trials) during the 2006 growing season. 

At each test location, a single preemergence application of Reflex®
Herbicide (EPA Reg. No. 100-993) was made to potatoes at 0.237 to 0.263
lb ae (acid equivalents)/A.  Reflex® Herbicide is a soluble concentrate
liquid formulation containing 22.8% sodium salt of fomesafen as the
active ingredient (equivalent to 2 lb ae/gal of fomesafen). 
Applications were made using ground equipment in spray volumes of 16-36
gal/A without an adjuvant.  Samples of mature potatoes were collected at
a PHI of 70-141 days.  Additional samples were collected from one trial
to conduct a processed food and feed study; refer to the 860.1520 DER
for MRID 47473903 for the study details and results.

Samples of potatoes were analyzed for residues of fomesafen using a
LC/MS/MS method based on an HPLC/UV method (GAM-RM-001/86), entitled
“The Determination of PP021 in Soybeans – A High Performance Liquid
Chromatographic Method,” which is an enforcement method for fomesafen.
 The method was adequate for data collection based on adequate
concurrent recovery data.  The LLMV was 0.025 ppm for potato.

The maximum storage duration of potatoes from harvest to analysis was
399 days (13.1 months) for analysis of fomesafen.  Sample storage
conditions and durations are supported by concurrent storage stability
data.  However, zero-day data were not provided with the storage
stability study.  The petitioner is reminded that storage stability
studies should always include a zero-day sampling interval to ensure
that the samples were fortified properly [see OPPTS 860.1380(d)(6)(i)].

Residues of fomesafen were less than the LLMV (<0.025 ppm) in/on
potatoes harvested 70-141 days following a single pre-emergence
application of the 2 lb ae/gal SL formulation of fomesafen at a total
rate of 0.237-0.263 lb ae/A.

Pepper

  SEQ CHAPTER \h \r 1 Syngenta Crop Protection has submitted field trial
data for fomesafen on peppers.  Thirteen crop trials were conducted in
the United States. Nine trials were conducted on bell peppers in Zones 2
(NJ, NC, and MD, 3 trials), 3 (FL; 1 trial), 5 (MI and OH; 2 trials ), 6
(TX; 1 trial) and 10 (CA, 2 trials), and four trials were conducted on
non-bell cultivars (chili peppers) in Region 3 (FL, 1 trial), 6 (TX, 1
trial), 5 (MI, 1 trial), and 10 (NM, 1 trial) during the 2006 growing
season.  

At each test location, a single broadcast application to soil surface of
Reflex® Herbicide (EPA Reg. No. 100-993) was made prior to
transplanting peppers at a rate of 0.362 to 0.385 lb ae/A.  Reflex®
Herbicide is a SL formulation containing 22.8% sodium salt of fomesafen
as the active ingredient (equivalent to 2 lb ae/gal of fomesafen). 
Applications were made using ground equipment in spray volumes of 19-35
gal/A without an adjuvant.  Pepper fruit samples were harvested at
commercial maturity, 59 to 121 days after treatment, 56 to 115 days
after transplanting.

Samples of raw pepper were analyzed for residues of fomesafen using an
ultra performance liquid chromatography method with mass spectrometry
detection (TMR0626B) based on a GC/NPD method.  The method was
adequately validated during concurrent analysis of samples.  The LLMV
was 0.025 ppm for pepper.

The maximum storage duration of pepper from harvest to analysis was 398
days (13.1 months) for analysis of fomesafen.  Sample storage conditions
and durations are supported by concurrent storage stability data. 

Residues of fomesafen were less than the  LLMV (<0.025 ppm) in/on
peppers harvested 59-121 days following a single pre-transplant
application of the 2 lb ae/gal SL formulation of fomesafen at a total
rate of 0.362-0.385 lb ae/A.

Conclusions.  The submitted field trials for potatoes are acceptable and
support the proposed uses, as the potato metabolism data gap has been
satisfied with the submitted confined rotational crop metabolism study. 
An adequate number of trials were conducted in the appropriate
geographic regions at ~1x the maximum proposed rate using Reflex®
Herbicide, and the appropriate samples were collected from each test
around the proposed PHI.  The confined rotational crop metabolism study
does not identify any additional residues of concern, and thus the field
trial data are adequate.  Based on these data, HED recommends a
tolerance of 0.025 ppm for residues of fomesafen in/on potatoes.

The submitted field trial data for fomesafen on peppers are acceptable
and support the proposed uses.  An adequate number of trials were
conducted in the appropriate geographic regions at ~1x the maximum
proposed rate using Reflex® Herbicide, and the appropriate samples were
collected from each test around the proposed PHI.  All treated samples
bore residues below the LLMV (<0.025 ppm).  Based on these data, HED
recommends a tolerance of 0.025 ppm for residues of fomesafen in/on bell
and non-bell peppers.

860.1520 Processed Food and Feed

DER Reference List	47473903.de2 (Potato)

			Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger

The observed processing factors reported for potatoes, resulting from
treatment at 1x, are presented in Table 7.

  SEQ CHAPTER \h \r 1 Table 7.   Summary of Observed Processing Factors
for Fomesafen in Potatoes Following Treatment at 1x.

RAC	Processed Commodity	Processing Factor

Potato, tuber	Flakes	NC1

	Chips	NC

	Wet peel	NC

1  NC = Not calculated.  The processing factor could not be calculated
because residues were below the LLMV (<0.025 ppm) in both the RAC and
the processed fractions.

Potato

Syngenta Crop Protection submitted magnitude of the residue data for
fomesafen on the processed commodities of potatoes.  Samples used for
processing were generated from two potato field trial conducted in ID
(Zone 11) during the 2006 growing season.  The test formulation used in
the trial was Reflex® Herbicide (EPA Reg. No. 100-993), a SL
formulation containing 22.8% sodium salt of fomesafen as the active
ingredient (equivalent to 2 lb ae/gal of fomesafen).  Potatoes were
harvested 130 days following a single preemergence application of a 2 lb
ae/gal SL formulation of fomesafen at 0.256 lb ae/A (~3x field
application rate).  Application was made using ground equipment in a
spray volume of 20 gal/A without an adjuvant.  The potatoes were
processed into potato flakes, chips and wet peel.

Samples of potatoes and potato processed commodities were analyzed for
residues of fomesafen using a high performance liquid chromatography
method with tandem mass spectrometry detection (LC/MS/MS) based on an
HPLC/UV method (GAM-RM-001/86), entitled “The Determination of PP021
in Soybeans – A High Performance Liquid Chromatographic Method,”
which is an enforcement method for fomesafen.  The method was adequate
for data collection based on adequate concurrent recovery data.  The
lowest level of method of validation (LLMV) was 0.025 ppm for potato
tuber and processed commodities flakes, chips, and wet peel.

The maximum storage duration of the processing study samples were 308
days (10.1 months) from harvest to analysis for potatoes (RAC) and 299
days (9.8 months), 298 days (9.8 months), and 293 days (9.6 months) from
processing to analysis for potato flakes, chips and wet peel,
respectively.  Sample storage conditions and durations are supported by
concurrent storage stability data.  However, zero-day data were not
provided with the storage stability study.  The petitioner is reminded
that storage stability studies should always include a zero-day sampling
interval to establish the residue levels present at the time samples are
placed into storage [see OPPTS 860.1380(d)(6)(i)].

Residues of fomesafen were less than the LLMV (<0.025 ppm) in/on the
potato tuber (RAC) and potato processed commodities.  Therefore,
concentration factors could not be calculated.  The petitioner is
reminded that samples used in processing studies should contain
field-treated quantifiable residues so that concentration factors can be
determined.  Field treatment of the processing samples should have been
done at exaggerated application rates to ensure that the samples were
fortified properly [see OPPTS 860.1520(c)(2)].

According to Tables 2 and 3 of OPPTS 860.1520, the theoretical
concentration factors for potato processed fraction are 4.0x for
processed waste (wet peel) and 4.7x for flakes/granules.  

Conclusions.  The results of submitted potato processing study show that
residues of fomesafen were each below the LLMV (<0.025 ppm) in/on the
respective RACs following application of Reflex® Herbicide at ~1x. 
Following processing of RACs bearing nonquantifiable residues, no
measurable processing factors can be calculated because the processed
commodities of potatoes also bore residues below the LLMV (<0.025 ppm). 
The Agency would have preferred the use of exaggerated rates in the
conduct of the processing studies to yield RACs with quantifiable
residues; the registrant provided no justification for conducting the
study at only a 1x rate.  Since the proposed use is for preemergence
application and all RAC samples from the current potato field trials
show residues below the LLMV and the residue data cover all significant
growing regions for the crop requested as delineated in OPPTS 860.1500,
for the purpose of this petition only, HED recommends a waiver for the
conduct of new potato processing studies at exaggerated rates.

The submitted processing study for potatoes is adequate, as the potato
metabolism data gap has been satisfied with the submitted confined
rotational crop metabolism study.   The confined rotational crop
metabolism study does not identify any additional residues of concern,
and thus the potato processing study is adequate.  

  SEQ CHAPTER \h \r 1 860.1650 Submittal of Analytical Reference
Standards

Analytical standards for fomesafen are currently available in the EPA
National Pesticide Standards Repository (personal communication with
Theresa Cole, 9/20/10).  The standard has an expiration date of August
2012.

Analytical reference standards of fomesafen must be supplied and
supplies replenished as requested by the Repository.  The reference
standards should be sent to the Analytical Chemistry Lab, which is
located at Fort Meade, to the attention of either Theresa Cole or Thuy
Nguyen at the following address:

	USEPA

	National Pesticide Standards Repository/Analytical Chemistry Branch/OPP

	701 Mapes Road

	Fort George G. Meade, MD  20755-5350

(Note that the mail will be returned if the extended zip code is not
used.)

860.1850 Confined Accumulation in Rotational Crops

Reference List:	47937602.der.doc

Syngenta has submitted a confined rotational crop study with
[trifluoromethylphenyl-U-14C] fomesafen (TMP label; specific activity
55.8 µCi/mg) and [nitrophenyl-U-14C] fomesafen (NP label; specific
activity 56.2 µCi/mg). Each radiolabeled test substance was formulated
as SL and applied as a single bare-ground spray in plots in Madera, CA
at a rate of 0.375 lb ae/A (1x the maximum proposed seasonal rate for
any rotatable crop).  Rotational crops (wheat, soybean, potato, spinach,
radish and carrot) were planted 90/91, 224 and 270 days after soil
treatment, after which the total radioactive residues (TRR) of the crops
was quantified.  Phytotoxicity necessitated usage of the following
rotational crops and plant back intervals (PBI): 90 day PBI for wheat
(forage, hay, straw, grain) as the small grain; 91 day PBI for soybeans
(forage, hay, seeds) as a leafy vegetable and potatoes (foliage, roots)
as a root vegetable; 224 day PBI for wheat (forage, hay, straw, grain),
radish (foliage, root), and spinach (immature, mature); 270 PHI for
wheat (forage, hay, straw, grain), carrot (foliage, root), and spinach
(immature, mature). 
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摥愠⁴灡牰灯楲瑡⁥湩整癲污⁳潦⁲湡污獹獩മ

TRR accumulated at ≥0.01 ppm in all rotational crop matrices planted
in the 90/91, 224 and 270 day PBIs, except for radish roots.

The majority of radioactivity was extracted from rotational crop
matrices using ACN/water.  In some cases, additional extractions were
necessary to remove radiolabel from the PES.  Typically the PES was
extracted further with ACN:0.5 M KOH, 6 M HCl, 72% sulfuric acid, 24%
KOH, and 80% dioxane in 0.05 M HCl.  

Total radioactive residues (TRR) in RACs were determined by combustion
and may be found in Table 8.  TRR in extracts were determined by liquid
scintillation counting (LSC).  Fomesafen and its metabolites were
quantified and determined by liquid chromatography with ultraviolet
detection (LC/UV), liquid chromatography- mass spectrometry (LC/MS) and
nuclear magnetic resonance (NMR).  Identification was confirmed by
thin-layer chromatography (TLC).

Total radioactive residues (TRR, ppm) were highest in all commodities at
the 90/91 day PBI and decreased at the longer PBIs of 224 and 270 days. 
The TRR in the 224 and 270 days PBI samples were generally comparable. 

Residues in the wheat commodities were highest in the 90 days PBI
samples with fomesafen the highest residue, ranging from 0.01 ppm in
grain to 0.329 ppm in the hay.  The other major residues found in wheat
were trifluoroacetic acid (TFAA) conjugates in forage, hay and straw
(0.019 – 0.064 ppm).  At the later PBI intervals of 224 days and 270
days, fomesafen decreased in grain, forage, hay and straw.  The TFAA
conjugates also had the highest residues at the 90 day PBI, 0.035, 0.064
and 0.047 ppm being the maximum residues in the forage, hay and straw,
respectively.  No other major residue was found in these commodities.  

Three different root crops were used, potatoes at the 91 day PBI, radish
at the 224 day PBI and carrots at the 270 day PBI.  The residues in the
tubers or roots were low across all three crops (TRR < 0.01 ppm).  The
residue was made up of fomesafen, R290493 and TFAA conjugates.  Residues
in the potato, radish and carrot foliage tops were higher, with the
major residue comprised of fomesafen and TFAA conjugates.  For potato,
radish and carrot foliage, the highest fomesafen residues were 0.005,
0.011, and 0.017, respectively, and highest TFAA conjugate residues
0.013, 0.023, and 0.017 ppm TRR, respectively.  R290493 found in potato
foliage at 25.9% TRR as well, at 0.007 ppm TRR.

Soybeans were planted at the 91 day PBI, and spinach at the 224 day and
270 day PBI.  The highest residues were found in the 91 day PBI soybean
forage and hay.  The major components of the residue in the soybean
forage and hay were a TFAA conjugate (0.035 – 0.136 ppm), a R052850
lipid conjugate (0.02 – 0.061 ppm), and R290493 (0.015 - 0.016 ppm). 
Residues of fomesafen were low (less than or equal to 0.003 ppm) or not
detected in the soybean forage, hay or seed.   The only residue detected
in soybean seed was 0.005 ppm TFAA conjugate. Lower residues were found
in the immature and mature spinach at the 224 and 270 day PBI, with the
major residue components being fomesafen and TFAA conjugate.  The
maximum TRR of fomesafen in spinach was 0.015 ppm and the maximum TRR of
TFAA conjugate was 0.023 ppm.  R290493 was found in 224 day PBI immature
spinach at >10% TRR, but at only 0.002 ppm TRR.

The major components taken up in rotated crops are fomesafen and TFAA
conjugates.  R052850 lipid conjugate reached 0.061 ppm and was unique to
soybean forage and hay (although Peak 9 in 90 day PBI TMP-label wheat
straw may correspond to R052850).  The uptake results in low residues of
fomesafen or TFAA conjugates, except for fomesafen found in the wheat
hay and straw at up to 0.329 ppm.  

The dates of application, harvest, combustion, extraction and analysis
were reported.  No storage stability determination was reported as
processing, extraction and analysis did not exceed 4-6 months from
harvest.  

Based on the submitted confined rotation crop study, the petitioner
described the metabolic pathway of fomesafen.   Fomesafen is cleaved at
the biphenyl ether linkage (probably glutathione-mediated) to TMP moiety
2-chlor-4-trifluoromethylphenol (not observed) and Cys conjugate
R290493.  2-chloro-4-trifluoromethylphenol is further rapidly converted
to either TFAA conjugates (A and B) and/or R052850 lipid conjugate (in
soybean foliage RACs).  Formation of TFAA conjugates reflects
opening/extensive oxidation of the phenyl ring.  

TABLE 8.	Total Radioactive Residues (TRRs) in Rotational Crops.

Matrix	Plant-back interval (days)	NP Label	TMP Label

ppm	ppm

Wheat Forage	90	0.141	0.180

	224	0.038	0.034

	270	0.027	0.039

Wheat Hay	90	0.515	0.526

	224	0.075	0.074

	270	0.100	0.113

Wheat Straw	90	0.823	0.864

	224	0.239	0.115

	270	0.139	0.107

Wheat Grain	90	0.027	0.024

	224	0.009	0.006

	270	0.009	0.012

Soybean Forage	91	0.058	0.142

Soybean Hay	91	0.169	0.364

Soybean Seeds	91	0.013	0.025

Potato Foliage	91	0.027	0.061

Potato Root	91	0.008	0.008

Spinach, Immature	224	0.019	0.024

	270	0.024	0.040

Spinach, Mature	224	0.015	0.025

	270	0.013	0.029

Radish Foliage	224	0.014	0.031

Radish Roots	224	0.005	0.009

Carrot Foliage	270	0.068	0.087

Carrot Roots	270	0.004	0.010

Table 9.  Summary of Major Residues Found in Fomesafen Confined
Rotational Crop Study

Analyte	Residues Found - %TRR (Label Position in Parentheses)

Fomesafen	Wheat Forage (NP) 90/224/2701 – 65.2/68.4/70.4   Wheat
Forage (TMP) 90/224/270 – 36.1/11.8/35.9

Wheat Hay (NP) 90/224/270 – 63.9/50.7/48.0   Wheat Hay (TMP)
90/224/270 – 51.9/14.9/21.2

Wheat Straw (NP) 90/224/270 – 30.4/38.1/43.2   Wheat Straw (TMP)
90/224/270 – 35.3/24.3/34.6

Wheat Grain (NP) 90/224/270 – 44.4/33.3/33.3   Wheat Grain (TMP)
90/224/270 – 25/16.7/16.7

Potato Foliage (NP) 91 day – 18.5   Potato Foliage (TMP) 91 day –
6.6

Potato Root (NP) 91 day – 25.0   Potato Root (TMP) 91 day – 25.0

Immature Spinach (NP) 224/270  – 57.9/62.5   Immature Spinach (TMP)
224/270 day – 4.2/32.5

Mature Spinach (NP) 224 /270 – 60.0/53.8   Mature Spinach (TMP)
224/270 day – 4.0/20.7

Radish Foliage (NP) 224 day – 78.6   Radish Foliage (TMP) 224 day –
19.4

Radish Root (TMP) 224 day – 44.4

Carrot Foliage (NP) 270 day – 30.9   Carrot Foliage (TMP) 270 day
–19.5

Carrot Root (NP) 270 day – 25.0   Carrot Root (TMP) 270 day –10.0

Soybean Forage (NP) 91 day – 3.4   Soybean Forage (TMP) 91 day – 0.7

Soybean Hay (NP) 91 day – 1.8

R052850 Conjugate	Soybean Forage (TMP) 91 day – 14.1 (0.02 ppm)

Soybean Hay (TMP) 91 day – 16.8(0.061 ppm)

Wheat Straw (TMP) 90/224/270 – 3.6/ND/ND (<0.031 ppm)

TFAA Conjugates	Wheat Forage (TMP) 90/224/270 – 20/73.5/51.3

Wheat Hay (TMP) 90/224/270 – 12.6/64.9/45.1 

Wheat Straw (TMP) 90/224/270 – 9.9/28.7/17.8

Wheat Grain (TMP) 90/224/270 – ND/33.3/33.3

Soybean Forage (TMP) 91 day – 26.0

Soybean Hay (TMP) 91 day – 37.4

Potato Foliage (TMP) 91 day – 37.7

Potato Root (TMP) 91 day – 50.0 

Immature Spinach (TMP) 224/270 – 79.2/52.5 

Mature Spinach (TMP) 224/270 – 92.0/55.2 

Radish Foliage (TMP) 270 day –74.2 

Radish Root (TMP) 270 day –33.3 

Carrot Foliage (TMP) 270 day –19.5

Carrot Root (TMP) 270 day –40.0 

Soybean Seed (TMP) 91 day – 20.0  

R290493

2-amino-3-(3
–methanesulfonylamino-carbonyl-4-nitro-phenylsulfany1)-propionic acid
Soybean Forage (NP) 91 day – 27.6 

Potato Foliage (NP) 91 day – 25.9 

Potato Root (NP) 91 day – 12.5 

Immature Spinach (NP) 224 day – 10.5

Wheat Forage (NP) 90/224/270 – 1.4/2.6/3.7

Wheat Straw (NP) 90/224/270 – ND/3.3/2.2

Soybean Hay (NP) 91 day – 8.9 

Immature Spinach (NP) 270 day – 4.2 

Mature Spinach (NP) 270 day – 7.7 

Radish Foliage (NP) 224 day – 7.1 

1 These values refer to the plant-back interval. In days NP =
nitrophenyl label.  TMP = trifluoromethylphenyl label.

The major components in rotated crops are fomesafen, trifluoroacetic
acid (TFAA) conjugates, R052850 conjugates, and R290493.  The highest
residues found of fomesafen were in wheat hay, forage and straw at
levels up to 0.329 ppm for fomesafen; TFAA conjugates were found at
levels up to 0.064 ppm in wheat commodities.  The highest residues found
of TFAA conjugates were in soybean hay at levels up to 0.136 ppm.  The
highest residues found of R052850 lipid conjugate and R290493 were in
soybean forage and hay at levels up to 0.061 ppm for R052850 lipid
conjugate and 0.016 ppm for R290493.

Conclusions.  The submitted confined rotational crop data are adequate
to satisfy data requirements.  The study appears to have adequately
delineated the nature of the residue in rotational crops.  The
metabolism of fomesafen appears to proceed in rotational crops via
similar mechanisms and to be more extensive than that observed in
primary crops.  TFAA conjugate metabolites were identified in rotational
crops that were not identified in primary crops.  HED has determined
that the residue of concern for the tolerance expression in rotation
crops is fomesafen per se.  HED has also determined that the residue of
concern for the risk assessment in rotational crops is fomesafen.

The submitted confined study indicated the potential for quantifiable
fomesafen residues in rotated crop commodities at 90/91, 224 and 270 day
plantback intervals.

860.1900 Field Accumulation in Rotational Crops

Reference List:	47761905 (No DER generated)

		00158936.der.wpd

		45268501.der.wpd

Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis

Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger

HED previously summarized (DP# 325801, 4/25/2006, D. Davis) the
available field accumulation data for fomesafen.  The available data
consisted of:  (i) MRID 00110509 which was reviewed by the Environmental
Fate and Effects Division (EFED) and was found to contain numerous
deficiencies; (ii) MRID 00158936, a field rotational crop study on field
corn and winter wheat; and (iii) MRID 45268501, a field rotational crop
study on field corn and safened sorghum.  HED previously concluded that
the adequacy of these data cannot be determined until the nature of
fomesafen residues in rotational crops has been delineated.  

Syngenta has adequately responded to HED’s concerns and comments
regarding the analytical method (PPRAM No. 66) used for the analysis of
fomesafen from a previously submitted field rotational crop study (MRID
00158936) (See DP barcode D365119 and 366116, C. Olinger, 1/21/2010). 
Syngenta has provided detailed information/data concerning:  (i) when
the fortification of external recoveries were performed; (ii) data to
support the reported LOQ of 0.01 ppm; (iii) data demonstrating that
recoveries of the internal standard are linear relative to recoveries of
fomesafen; and (iv) information on the identity of matrices fortified to
validate the method.  This deficiency is resolved.

As for the deficiency of data concerning the nature of the residue in
rotational crops, this data gap has been fulfilled with the submission
of the confined rotational crop metabolism study as described above. 
This data can support rotation to other crops beyond those commodities
that are currently registered and proposed as primary crops.  All plant
back intervals (PBIs) for rotational crops on the draft label are
acceptable, including a 4 month PBI for small grains (wheat and similar
commodities), a 10 month PBI for corn, peanuts, peas, rice, and seed
corn, and an 18 month PBI for alfalfa, sunflowers, sugar beets and
sorghum.  The submitted confined rotational crop study is adequate to
determine the nature of residues in rotational crops; the residue of
concern for rotational crops is fomesafen (D373600, A. LaMay, 10/12/10).

860.1550 Proposed Tolerances/Tolerance Reassessments for Fomesafen

Tolerances for fomesafen residues are listed in 40 CFR §180.433.  The
tolerance expression is in terms of “sodium salt of fomesafen,
5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzam
ide.”  HED has determined that the residue of concern for tolerance
expression is fomesafen.  Therefore, the established tolerance
expression should be revised to be expressed in terms of fomesafen, by
removing the phrase “sodium salt of” from 40 CFR §180.433(a).  In
accordance with the HED Interim Guidance on Tolerance Expressions
(5/27/09, S. Knizner), the tolerance expression for fomesafen should be
revised to state:

“Tolerances are established for residues of fomesafen, including its
metabolites and degradates, in or on the commodities in the table below.
 Compliance with the tolerance levels specified below is to be
determined by measuring only fomesafen
[5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenza
mide].”

The available crop field trial data and revised analytical method will
support the proposed tolerance of 0.025 ppm for pepper and potato.  As
all residues were below the LLMV (<0.025 ppm) in/on RAC samples treated
at 1x, the Agency’s tolerance spreadsheet was not used for determining
the recommended tolerances.  The petitioner’s draft label for Reflex®
Herbicide reflects regional use of fomesafen on pepper and potato. 
However, the residue chemistry data submitted in support of this action
are of sufficient geographic representation to support full U.S.
registration; therefore, HED recommends that this tolerances be listed
in the general section of 40 CFR §180.433.  Note that the commodity
term for pepper should be modified as described in table below.

No tolerances are required for meat, milk, poultry, and eggs for the
purpose of this petition.  Syngenta should note that if additional uses
are proposed in the future which result in an increase in the dietary
burden, livestock feeding studies and animal tolerances may be required.

No Codex, Canadian, or Mexican MRLs have been established for residues
of fomesafen in/on potato or pepper.  Canadian MRLs have been
established for residues of fomesafen in/on dry beans, lima beans, snap
beans, and soybeans at 0.05 ppm, and a Mexican MRL of 0.05 mg/kg  has
been established for residues of fomesafen in/on soybeans.  The
registrant has advised the Agency that they intend to petition the
Canadian government for revised tolerances to address any potential
harmonization issues raised by establishing the new tolerances requested
in this action.

A summary of the tolerance reassessment for fomesafen sodium is
presented in Table 10.  

Table 10.   Tolerance Summary for Fomesafen Sodium

Commodity	Established/Proposed Tolerance (ppm)	Recommended Tolerance
(ppm)	Comments; Correct Commodity Definition

Proposed Tolerance Under PP#9F7563

Potato	0.025	0.025

	Proposed Tolerance Under PP#9F7667

Pepper	0.025	0.025	Pepper, bell

Pepper, non-bell

References

DP#:	325801

Subject:	Fomesafen Sodium.  Residue Chemistry Summary for the HED Human
Health Risk Assessment, a Proposal To Amend Use on Soybeans, and
Proposals to Add Uses on Cotton, Dry Bean, and Snap Bean.  PP#1E6228,
PP#9F5068, and PP#6E4653.

From:	D. Davis

To:	J. Stone/J. Miller

Dated:	4/25/06

MRIDs:	00158936, 00158937, 40346603, 44754701-44754704, 44754706,
44727901, 45093601-45093604, 45237101, 45259801, 45268501-45268503,
45313001, & 45342601

DP#:	365199 and 366116

Subject:	Fomesafen Sodium.  Petition for the Establishment of Tolerances
and Registration of New Uses on Potato and Tomato; and Response to Data
Gaps for Conditional Registration on Cotton, Dry Bean, and Snap Bean. 
Summary of Analytical Chemistry and Residue Data.  PP#1E6228, PP#9F5068,
PP#6E4653, and PP#9F7563.

From:	C. Olinger

To:	D. Kenny/M. Walsh

Dated:	1/21/2010

MRIDs:	47473901, 47473902, 47473903, 47761901, 47761902, 47761903,
47761904, and 47761905.

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Appendix I	International Residue Limit Status Sheet

Appendix II	Chemical Names and Structures of Metabolites Identified 

Appendix I

International Residue Limit Status Sheet

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name:
5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzam
ide	Common Name:

Fomesafen	X Proposed tolerance

□ Reevaluated tolerance

□ Other	Date: 5/27/10

Codex Status (Maximum Residue Limits)	U. S. Tolerances

X No Codex proposal step 6 or above

□ No Codex proposal step 6 or above for the crops requested	Petition
Number:  PP#9F7563 and PP#9F7667

DP#:  D373544 and D382067

□ No Limits

X  No Limits for the crops requested	□ No Limits

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MRL (mg/kg)

	Notes/Special Instructions:

S.Funk, 5/27/2010.

Appendix II

Chemical Names of Metabolites Identified

Identification of Compounds.

Common name/code

Page   PAGE  2  of   NUMPAGES  30 

Fomesafen Sodium	Summary of Analytical Chemistry and Residue Data	DP#s:
D373544 and D382067