Document ID: EPA-HQ-OPP-2008-0125-0007
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2011-02-02T05:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF PREVENTION, PESTICIDES

	AND TOXIC SUBSTANCES

  SEQ CHAPTER \h \r 1 MEMORANDUM

Date:  09/29/2008

Subject:	Sulfentrazone.  Section 3 Registration Request to Add New Uses
on:  Brassica, Head and Stem, Subgroup 5A; Brassica, Leafy Greens,
Subgroup 5B; Melon, Subgroup 9A; Fruiting Vegetable, Group 8 and Okra;
Pea, Succulent; Flax; Strawberry; and Tuberous and Corm Vegetable,
Subgroup 1C.  Summary of Analytical Chemistry and Residue Data.

PC Code:  129081	DP Barcode:  D349321

Decision No.:  388050	Registration Nos:  279-3220 & 279-3189

Petition No.:  7E7308	Regulatory Action:  Amended Section 3

Risk Assessment Type:  NA	Case No.:  NA

TXR No.:  NA	CAS No.:  122836-35-5

MRID No.:  see MRID Summary Table	40 CFR:  §180.498

From:		William D. Wassell, Chemist

		Registration Action Branch 1 (RAB1)

		Health Effects Division (HED, 7509P)

Through:	George F. Kramer, Ph.D., Branch Senior Chemist

		RAB1/HED (7509P)

To:		Daniel Rosenblatt, RM 05

	Registration Division (RD, 7505P) 

MRID Summary Table

MRID No.	Study Type	Comments

47311401	860.1500 broccoli	New DER; 47311401.der.doc

47311402	860.1500 mustard greens	New DER; 47311402.der.doc

47311403	860.1500 cantaloupe	New DER; 47311403.der.doc

47311404	860.1500 pepper	New DERs; 47311404.der.doc (includes MRID
47311405) and 47311405.der.doc

47311405	860.1500 tomato

860.1520 tomato

	47311406	860.1500 succulent pea	New DER; 47311406.der.doc

47311407	860.1500 flax

860.1520 flax	New DERs; 47311407.de1.doc and 47311407.de2.doc

47311408	860.1500 strawberry	New DER; 47311408.der.doc

  SEQ CHAPTER \h \r 1 This document was originally prepared under
contract by Dynamac Corporation (2275 Research Boulevard, Suite 300;
Rockville, MD 20850; submitted:  05/22/2008).  This document has been
reviewed by HED and revised to reflect current Office of Pesticide
Programs (OPP) policies.

Executive Summary

  SEQ CHAPTER \h \r 1 Sulfentrazone is an aryl triazolinone herbicide
used to control a variety of broadleaf weeds.  The mode-of-action for
controlling emerging weeds is by protoporphyrinogen oxidase (PPO)
inhibition.  Sulfentrazone acts by the same mechanism as the diphenyl
ether herbicides in which membrane disruption is initiated by the
inhibition of PPO in the chlorophyll biosynthetic pathway and leads to
the subsequent build-up of toxic intermediates.  Plants emerging from
soils treated with sulfentrazone turn necrotic and die shortly after
exposure to light.

The Interregional Research Project No. 4 (IR-4) has submitted a petition
proposing the establishment of permanent tolerances for the combined
residues of the herbicide sulfentrazone
[N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2
,4-triazol-1-yl]phenyl]methanesulfonamide] and its metabolites HMS
[N-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-hydroxymethyl-5-oxo
-1H-1,2,4-triazol-yl)phenyl)methanesulfonamide)] and DMS [(N-2,4-
dichloro-5-[4-(difluoromethyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl)p
henyl)methanesulfonamide] in/on:

Brassica, head and stem, subgroup 5A*	0.20 ppm

Brassica, leafy greens, subgroup 5B	0.35 ppm

Melon, subgroup 9A	0.10 ppm

Vegetable, fruiting, group 8	0.05 ppm

Okra	0.05 ppm

Pea, succulent	0.05 ppm

Flax	0.05 ppm

Strawberry	0.05 ppm

Vegetable, tuberous and corm, subgroup 1C*	0.15 ppm

	*  Individual tolerances are established for residues in/on cabbage at
0.20 ppm and potato at 0.15 ppm.

A tolerance is currently established under 40 CFR §180.498(a)(1) for
the combined residues of sulfentrazone and its major metabolite, HMS,
in/on soybean seed at 0.05 ppm.  In addition, permanent tolerances are
established under 40 CFR §180.498(a)(2) for the combined residues of
sulfentrazone and its metabolites HMS and DMS in/on several food
commodities; these established tolerances range from 0.15 ppm (various
plant commodities) to 0.40 ppm (peanut meal).  Time-limited tolerances
for the combined residues of sulfentrazone and its metabolites HMS and
DMS have been established under 40 CFR §180.498(b) in connection with
Section 18 Emergency Exemptions; these include tolerances for residues
in/on bean, succulent-seed without pod (lima bean & cowpea) at 0.1 ppm
with a 12/31/07 expiration date, flax seed at 0.2 ppm with a 12/31/10
expiration date, and strawberry at 0.60 ppm with a 12/31/10 expiration
date.  Finally, tolerances are established under 40 CFR §180.498(d) for
inadvertent and indirect combined residues of sulfentrazone and its
metabolites HMS and DMS in/on cereal grain (excluding sweet corn) bran,
forage, grain, hay, hulls, stover, and straw at 0.1-0.6 ppm as a result
of the application of sulfentrazone to growing crops.

  SEQ CHAPTER \h \r 1 There are no Mexican, Canadian or Codex maximum
residue limits (MRLs) established for sulfentrazone in/on any of the
subject crops; therefore, there are no compatibility issues to be
reconciled.

The sulfentrazone end-use products (EPs) relevant for this registration
request are Spartan® Herbicide (EPA Reg. No. 279-3189; 75% dry-flowable
or DF formulation) and Spartan® 4F Herbicide (EPA Reg. No. 279-3220; 4
lb/gal flowable-concentrate (FlC) formulation).  IR-4   SEQ CHAPTER \h
\r 1 requests the amendment of these EP labels to incorporate new uses
on head and stem Brassica, leafy greens Brassica, fruiting vegetables
including okra, melons, strawberry, succulent peas and beans, and flax. 
These EPs are proposed for:  (i) preplant or preemergence applications
on all of the above-listed crops at maximum seasonal rates of
0.1875-0.375 lb ai/A using ground or aerial equipment; and (ii)
postemergence applications on fruiting vegetables at a maximum seasonal
rate of 0.375 lb ai/A.  No pre-harvest intervals (PHIs) were proposed
for these crops.

The nature of the residue in soybeans as well as rotational crops is
adequately understood.    SEQ CHAPTER \h \r 1 The HED Metabolism
Committee has determined that the parent compound, sulfentrazone, and
the metabolite HMS are the residues of concern in soybeans, and that
sulfentrazone and the metabolites HMS and DMS are the residues of
concern in rotational crops (D226434, 6/14/96, G. Kramer).  In addition,
HED concluded that the results of the rotational crop metabolism studies
may be translated to support preemergence uses on all types of crops
(D220548, 3/13/96, G. Kramer).  However, as the proposed use pattern on
fruiting vegetables includes postemergence applications, metabolism data
are not available to support this specific use pattern.  HED is,
therefore, recommending that all proposed uses should be limited to
preemergence application only unless the petitioner is willing to submit
new metabolism studies on fruiting vegetables reflecting postemergence
application.  However, as the enforcement method for plant commodities
determines free and conjugated forms of the analytes, the tolerance
expression should be revised to indicate the residues of concern are the
combined residues of free and conjugated sulfentrazone, and its
metabolites HMS and DMS.

The nature of the residue in livestock is adequately understood based on
acceptable ruminant and poultry metabolism studies.  Sulfentrazone per
se and its metabolites HMS and DMS were identified as the residues of
concern in meat, milk, poultry, and eggs.  Based on established and
proposed sulfentrazone tolerances and the results of livestock
metabolism studies, conventional feeding studies and tolerances for
livestock commodities are not required for the purpose of this petition
only.

There is an adequate residue analytical method for the purposes of
tolerance enforcement.  A gas chromatography (GC) method for the
determination of sulfentrazone and its metabolites DMS and HMS was
submitted with a petition for a sulfentrazone tolerance on soybeans (PP#
4F04407).  A petition method validation (PMV) was successfully completed
by the Agency’s Analytical Chemistry Laboratory (ACL).  The limit of
quantitation (LOQ) and limit of detection (LOD) were determined to be
0.05 ppm and 0.005-0.025 ppm, respectively.  The method has been
forwarded to the Food and Drug Administration (FDA) for inclusion in the
Pesticide Analytical Methods Vol. II (PAM II).

The data requirements for multiresidue methods (MRMs) are fulfilled. 
The FDA MRMs are not suitable as enforcement methods since sulfentrazone
residues of concern were not successfully recovered by the FDA MRMs.

Samples of raw agricultural and processed commodities were analyzed for
residues of sulfentrazone and its metabolites DMS and HMS using either a
GC/XSD halogen-specific detector) method or a liquid chromatograph
equipped with tandem mass spectrometers (LC/MS/MS) method.  The
validated LOQ was 0.05 ppm for each analyte.  These methods are adequate
for data collection based on acceptable method validation and concurrent
recovery data.

Pending submission of a revised Section F as specified in Table 15,
adequate crop field trial data have been submitted for:  broccoli, one
of the representative commodities of head and stem Brassica (subgroup
5A); provided the proposed use directions (Section B) are modified,
mustard greens, the sole representative commodity of Brassica leafy
greens (subgroup 5B); peas (succulent and edible-podded); bell and
non-bell peppers and tomatoes, the representative commodities of
fruiting vegetables (group 8); cantaloupe, the sole representative
commodity of melon subgroup (subgroup 9A); strawberries; and flax.  The
submitted data showed that the combined residues of sulfentrazone, DMS,
and HMS were <0.15 ppm in/on mature commodities listed above following
application(s) of a representative formulation of sulfentrazone
according to the proposed crop use pattern.  It is, however, noted that
higher residues were observed in/on mustard green samples treated at
<1.0x.  The field trial data are supported by adequate storage stability
data, and no corrections need to be applied to the observed residue
levels.  A revised Section B should be submitted to remove the proposed
postemergence use on fruiting vegetables.

The previously reviewed data for potato, the representative commodity of
tuberous and corm vegetables (subgroup 1C) may be used to support the
requested use pattern for the subgroup.  These data were submitted as
part of PP# 2E6405 (D287102, 1/10/03, G. Kramer) and showed that the
maximum combined residues of sulfentrazone and its metabolites HMS and
DMS were 0.077 ppm in/on potato tubers after a preemergence treatment at
1x.

The previously reviewed data for cabbage, another representative
commodity of head and stem Brassica (subgroup 5A) may be used to support
the requested use pattern for the subgroup.  These data were submitted
in conjunction with PP#1E6311 (D276111, 12/9/02, G. Kramer) and indicate
that the combined residues of sulfentrazone, HMS, and SCA (quantitated
as DMS) were <0.15-0.18 ppm and <0.15-0.17 ppm in/on cabbage heads with
and without wrapper leaves, respectively, following application at 1x.

The submitted data for the fruiting vegetables may used to support the
proposed use on okra.

The submitted flax and tomato processing studies are unacceptable since
the studies did not conclusively demonstrate that sulfentrazone residues
of concern will not concentrate in processed fractions as a result of
the proposed use.  Quantifiable residues were not detected in the RACs
used for processing, and the field trials were conducted at only 1x
(flax) or 2x (tomatoes) rates.  Since phytotoxicity does not appear to
be an issue, the processing studies need to be repeated using an
exaggerated application rate (equal to the maximum theoretical
concentration factor or 5x, whichever is less).

stover, and straw.  As the 1x use rate in soybeans (0.375 lb ai/A) is
≥ the 1x use rate of the proposed new uses, the established tolerances
for indirect or inadvertent residues of sulfentrazone and its
metabolites, HMS and DMS are adequate to support the subject petition. 
The proposed rotational crop restrictions are adequate and consistent
with previous sulfentrazone petitions.

Analytical standards for sulfentrazone and its metabolites DMS and HMS
are currently available at the EPA National Pesticide Standards
Repository.  However, the standards for sulfentrazone and its metabolite
DMS will expire 10/1/2012 and 5/1/2012, respectively, and the standard
for HMS has expired 4/1/2008.

  SEQ CHAPTER \h \r 1 Regulatory Recommendations and Residue Chemistry
Deficiencies

HED has examined the residue chemistry database for sulfentrazone. 
There are no residue chemistry issues that would preclude granting a
conditional registration for the requested uses pending submissions of: 
a revised Section B (see requirements under Directions for Use);
reference standard for the metabolite HMS (see requirements under   SEQ
CHAPTER \h \r 1 Submittal of Analytical Reference Standards); and a
revised Section F (see Table 15).  Full and unconditional registration
will be granted following submission of adequate flax and tomato
processing studies.  The proposed uses and the submitted data support
the establishment of the following tolerances for the combined residues
of free and conjugated sulfentrazone and its metabolites HMS and DMS
in/on:

Brassica, head and stem, subgroup 5A	0.20 ppm

Brassica, leafy greens, subgroup 5B	0.40 ppm

Melon, subgroup 9A	0.15 ppm

Vegetable, fruiting, group 8	0.15 ppm

Okra	0.15 ppm

Pea, succulent	0.15 ppm

Flax	0.15 ppm

Strawberry	0.15 ppm

Vegetable, tuberous and corm, subgroup 1C	0.15 ppm

A human-health risk assessment is forthcoming.

Note to RD:  As the enforcement method for plant commodities determines
free and conjugated forms of the analytes, the tolerance expression
should be revised to indicate tolerances are established for combined
residues of free and conjugated forms of sulfentrazone, and its
metabolites HMS and DMS.

860.1200 Directions for Use

A revised Section B is required.  The proposed label for Spartan® 4F
Herbicide (EPA Reg. No. 279-3220), a 4 lb/gal FlC formulation, should be
modified to correct the application rates listed as “dry ounces
Spartan® Herbicide per acre” to “fluid ounces Spartan® Herbicide
per acre.”  Also, as metabolism data are not available to support
postemergence applications on fruiting vegetables, these proposed uses
should be limited to preemergence application only.  Additionally, the
proposed labels should be revised to specify a maximum single and
seasonal application rate of 0.020 lb ai/A for Spartan® to Brassica
leafy greens subgroup 5B as this rate is supported by the submitted crop
field trial data for mustard greens.  

860.1520 Processed Food and Feed

New flax and tomato processing studies should be submitted.  Since
phytotoxicity does not appear to be an issue, the requested processing
studies should use an exaggerated application rate (equal to the maximum
theoretical concentration factor or 5x, whichever is less).

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

As the reference standard for the metabolite HMS has expired 4/1/2008,
the petitioner must submit a new standard.  If new standards are being
submitted, they should be sent to the Analytical Chemistry Lab, which is
located at Fort Meade, to the attention of either Theresa Cole or Thuy
Nygen at the following address:

	USEPA

	National Pesticide Standards Repository/Analytical Chemistry Branch/OPP

	701 Mapes Road

	Fort George G. Meade, MD  20755-5350

860.1550 Proposed Tolerances

A summary of recommended tolerances are presented in Table 15.  The
petitioner is required to submit a revised Section F to reflect
appropriate tolerance levels.

Background

The chemical structure and nomenclature of sulfentrazone are presented
in Table 1, and the physicochemical properties of the technical grade of
sulfentrazone are presented in Table 2.



Table 1.  Sulfentrazone Nomenclature.

Chemical structure	

Common name	Sulfentrazone

Company experimental name	F6285; FMC 97285

IUPAC name	  SEQ CHAPTER \h \r 1
2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-
triazol-1-yl)methanesulfonanilide

CAS name	  SEQ CHAPTER \h \r 1
N-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,
4-triazol-1-yl)phenyl)methanesulfonamide

CAS registry number	122836-35-5

End-use product (EP)	4 lb/gal FlC formulation (Spartan® 4F Herbicide;
EPA Reg. No. 279-3220) and 75% DF formulation (Spartan® Herbicide; EPA
Reg. No. 279-3189)

Chemical structure of DMS metabolite	

Common name	3-desmethyl sulfentrazone; DMS

Chemical name
N-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol
-1-yl)phenyl)methanesulfonamide

Chemical structure of HMS metabolite	

Common name	3-hydroxymethyl sulfentrazone; HMS

Chemical name
N-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-hydroxymethyl-5-oxo-
1H-1,2,4-triazol-1-yl)phenyl)methanesulfonamide



Table 2.  Physicochemical Properties of Technical Grade Sulfentrazone.

Parameter	Value	Reference

Melting range	120-122 ºC	DP# 288712, 3/6/03, G. Kramer, G. Reddy, and
L. Liu

pH	4.78 at 23 ºC

	Density	0.53 g/cm3

	Water solubility	4.0 x 102 µg/g

	Solvent solubility	18.6% w/w in acetonitrile

	Vapor pressure	8 x 10-10 mm Hg

	Dissociation constant, pKa	6.56

	Octanol/water partition coefficient, Log(KOW)	1.49 at pH 5

	UV/visible absorption spectrum	Not available

	

860.1200  Directions for Use

A list of the sulfentrazone end-use products relevant to this
registration request is presented in Table 3.  The proposed crop use
directions are summarized in Table 4A.  Information regarding rotational
crop restrictions is listed in Table 4B.

Table 3.  Summary of Proposed End-Use Products.

Trade Name	Reg. No.	ai (% of formulation)	Formulation Type	Target Crops
Target Pests	Label Date

Spartan® 4F Herbicide	279-3220	39.6 (4 lb/gal)	FlC	Row Crops:  corn
(field, seed, and pop); peanut; potato; soybean; sugarcane; sunflower;
tobacco.

Vegetable Crops:  asparagus; Brassica, head and stem; Brassica, leafy
greens; cabbage (transplant only); dry shelled beans and peas; fruiting
vegetables (except cucurbits) and okra; horseradish; melons; strawberry;
succulent peas and beans;

Oil Crops:  flax; mint.	Broadleaf, grass, and sedge weeds.	Specimen
label code:  Spartan4F _3_12-17-07

Spartan® Herbicide	279-3189	75	DF

	Specimen label code:  Spartan

_3_12-17-07

Table 4A.  Summary of Proposed Directions for Use of Sulfentrazone.

Applic. Timing, Type, and Equip.	Formulation

[EPA Reg. No.]	Applic. Rate, 

lb ai/A

[Soil Type]	Max. No. Applic. per Season	Max. Seasonal Applic. Rate

(lb ai/A)	PHI

(days)

Brassica, Head and Stem [broccoli, Chinese broccoli, Brussels sprouts,
Chinese (napa) cabbage, Chinese mustard, cauliflower, cavalo broccoli,
kohlrabi]

Early preplant, preemergence, preplant incorporated	4 lb/gal FlC

[279-3220]	0.070-0.281

[coarse]

0.094-0.375

[medium and fine]	Not specified

(NS)	0.375	NS

	75% DF

[279-3189]

	Use Directions and Limitations  Do not incorporate to depths greater
than 2 inches.

Brassica, Leafy Greens [broccoli raab, Chinese (bok choy) cabbage,
collards, kale, mizuna, mustard greens, mustard spinach, rape greens]

Early preplant, preemergence, preplant incorporated	4 lb/gal FlC

[279-3220]	0.070-0.281

[coarse]

0.094-0.375

[medium and fine]	NS	0.375	NS

	75% DF

[279-3189]

	Use Directions and Limitations:  Do not incorporate to depths greater
than 2 inches.

Fruiting Vegetables (except curcurbits) [eggplant, groundcherry
(Physalis spp), pepino, pepper (includes bell pepper, chili pepper,
cooking pepper, pimento, sweet pepper), tomatillo, tomato] and okra

Preplant banded or postemergence with shielded/hooded sprayer	4 lb/gal
FlC

[279-3220]	0.070-0.281

[coarse]

0.094-0.375

[medium and fine]	NS	0.375	NS

	75% DF

[279-3189]

	Use Directions and Limitations:  None.

Succulent Peas and Beans [bean (Phaseolus; includes green lima bean and
succulent broad bean), bean (Vigna; includes blackeyed pea, cowpea,
southern pea), pea (Pisum; includes English pea, garden pea, green pea);
pigeon pea 

Preemergence	4 lb/gal FlC

[279-3220]	0.070-0.1875

[coarse]

0.094-0.1875

[medium]

0.117-0.1875

[fine]	NS	0.1875	NS

	75% DF

[279-3189]

	Use Directions and Limitations:  Do not incorporate.

Flax

Preemergence	4 lb/gal FlC

[279-3220]	0.070-0.281

[coarse]

0.094-0.375

[medium and fine]	NS	0.375	NS

	75% DF

[279-3189]

	Use Directions and Limitations:  Do not apply directly on crop after
the crop emergence or if the seedling sprouts are close to the soil
surface.



Melon [citron melon, muskmelon, watermelon]

Preemergence	4 lb/gal FlC

[279-3220]	0.093-0.1875

[coarse]

0.093-0.2125

[medium]

0.117-0.25

[fine]	NS	0.25	NS

	75% DF

[279-3189]

	Use Directions and Limitations:  Do not apply directly on crop after
the crop emergence or if the seedling sprouts are close to the soil
surface.

Strawberry

Preemergence	4 lb/gal FlC

[279-3220]	0.070-0.281

[coarse] 

0.094-0.375

[medium and fine]	NS	0.375	NS

	75% DF

[279-3189]

	Use Directions and Limitations:  Do not apply directly on crop after
the crop emergence or if the seedling sprouts are close to the soil
surface.

The following restrictions apply to all proposed crops:  Application
rates are dependent on soil texture, percent organic matter (%OM), and
pH.  Use on soils classified as sand which have <1% OM is prohibited. 
Applications are to be made in a minimum of 10 gallons per acre (GPA)
using ground equipment or a minimum of 5 GPA using aerial equipment.  



Table 4B.   Plantback Intervals for Use of Sulfentrazone.

Rotational Crop1	Plantback Interval (months)

Alfalfa	12

Barley	4

Cabbage	Anytime

Canola	24

Cereal Grains (Buckwheat, Oats, Pearl Millet, Proso Millet, Teosinte,
Wild Rice)	12

Corn, Field	10

Corn, Pop	18

Corn, Sweet	18

Cotton	18

Dry Shell Peas and Beans	Anytime

Horseradish	Anytime

Limas	Anytime

Mint	Anytime

Peanuts	Anytime

Potatoes	Anytime

Rice	10

Rye	4

Sorghum	10 2

Soybean	Anytime

Sugar Beets	36

Sugarcane	Anytime

Sunflowers	Anytime

Sweet Potatoes	12

Triticale	4

Tobacco	Anytime

Turf	Anytime

Wheat	4

1  For all other crops not listed, the rotation interval is a minimum of
12 months.

2  Sorghum – 18-month rotation for rates above 8.0 oz/A.

Conclusions.  The use directions are adequate to allow HED an assessment
of whether the submitted residue data reflect the maximum residues
likely to occur.  However, the label for Spartan® 4F Herbicide (EPA
Reg. No. 279-3220), a 4 lb/gal FlC (liquid) formulation, should be
modified to correct the application rates listed as “dry ounces
Spartan®  Herbicide per acre” to “fluid ounces Spartan® Herbicide
per acre”.  Also, as metabolism data are not available to support
postemergence applications on fruiting vegetables (except curcurbits),
these proposed uses should be limited to preemergence application only. 
Additionally, the proposed labels should be revised to specify a maximum
single and seasonal application rate of 0.020 lb ai/A to Brassica leafy
greens, subgroup 5B, as this rate is supported by the submitted crop
field trial data for mustard greens.  A revised Section B is required.

860.1300 Nature of the Residue – Plants and Livestock

DP# 226434, 6/14/96, G. Kramer (HED Metabolism Committee Meeting of
5/20/96)

DP# 220548, 3/13/96, G. Kramer

  SEQ CHAPTER \h \r 1 Data concerning the metabolism of sulfentrazone in
soybeans and confined rotational crops were submitted in conjunction
with the soybean petition (PP#4F04407).  Sulfentrazone is metabolized
via four different pathways:  (1) Oxidation of the 3-methyl group to
form 3-hydroxymethyl sulfentrazone or HMS, followed by further oxidation
to form sulfentrazone carboxylic acid which is decarboxylated to
3-desmethyl sulfentrazone or DMS.  (2) Hydrolysis of the trifluoromethyl
group to form desdifluoromethyl sulfentrazone which is oxidized and
decarboxylated to form desdifluoromethyl desmethyl sulfentrazone.  (3)
Hydrolysis of the sulfonamide group to form desmethylsulfonyl
sulfentrazone.  (4) Scission of the phenyl and triazole rings to produce
methyl triazole.  The corresponding phenyl metabolites are believed to
remain bound.

The HED Metabolism Committee has determined that the parent compound,
sulfentrazone, and the metabolite HMS are the residues of concern in
soybeans, and that sulfentrazone and the metabolites HMS and DMS are the
residues of concern in rotational crops (D226434, 6/14/96, G. Kramer). 
In addition, HED concluded that the results of the rotational crop
metabolism studies may be translated to support preemergent uses on all
types of crops (D220548, 3/13/96, G. Kramer).  

For the proposed uses of sulfentrazone, limited to preemergence
application, the nature of the residue in crops is understood.  The
residues of concern are sulfentrazone and its metabolites HMS and DMS. 
However, as the enforcement method for plant commodities determines free
and conjugated forms of the analytes, the tolerance expression should be
revised to indicate the residues of concern are the combined residues of
free and conjugated sulfentrazone, and its metabolites HMS and DMS. 
Additionally, as the proposed directions for use on fruiting vegetables
include postemergence applications, HED concludes metabolism data are
not available to support the postemergence applications.

Adequate ruminant and poultry metabolism studies were submitted in
conjunction with the soybean petition (PP#4F04407).  The metabolism of
sulfentrazone in livestock differs from that in plants as metabolism
proceeds only by oxidation of the 3-methyl group to form 3-hydroxymethyl
sulfentrazone (HMS), followed by further oxidation to form sulfentrazone
carboxylic acid which is decarboxylated to 3-desmethyl sulfentrazone
(DMS).  Sulfentrazone per se and its metabolites HMS and DMS were
identified as the residues of concern in meat, milk, poultry and eggs.

860.1340 Residue Analytical Methods

Letter dated 9/18/98 from G. Kramer to M. Clower (FDA)

D233520, 3/25/97, G. Kramer

Enforcement method

A GC analytical method for the determination of sulfentrazone, DMS, and
HMS residues (free and conjugated) in/on various matrices was submitted
with a petition for a sulfentrazone tolerance on soybeans (PP# 4F04407).
 A PMV was successfully completed by the Agency’s ACL.  The LOQ and
LOD were determined to be 0.05 ppm and 0.005-0.025 ppm, respectively. 
HED concluded that the method is suitable for enforcement purposes
(D233520, G. Kramer, 3/25/97).  The method was forwarded to FDA for
inclusion in PAM II (Letter, G. Kramer, 9/18/98).  This method is
suitable for enforcement of the tolerances associated with this
petition.

Data-collection methods

Samples of raw agricultural commodities (RACS) and processed commodities
were analyzed for residues of sulfentrazone and its metabolites DMS and
HMS using the FMC method entitled, “Analytical Methodology for the
Determination of Sulfentrazone, 3-Desmethyl Sulfentrazone, and
3-Hydroxymethyl Sulfentrazone in/on Various Matrices, Study Number
162MVL96R1” with minor modifications.  Residues in/on broccoli and
mustard greens were determined using GC/XSD, while residues in/on
cantaloupe, fruiting vegetables (pepper and tomato), peas, flax, and
strawberry were determined using LC/MS/MS.

Briefly, homogenized samples were refluxed with acetone:0.25N HCl
(30:10, v:v) for 1 hour followed by filtration and concentration, then
refluxed a second time with 1N HCI for 2 hours to free all conjugated
analytes of concern and to completely convert sulfentrazone 3-carboxylic
acid (SCA) to DMS.  The method quantifies residues of SCA as DMS and
calculates SCA residues by a molecular weight-conversion factor (1.12). 
SCA is a metabolism intermediate in formation of DMS.  The extract was
filtered, cleaned-up on a C8 solid-phase extraction (SPE) cartridge and
eluted with acetonitrile.  The eluate was dried under a gentle stream of
nitrogen and additionally cleaned up on a silicon (Si) SPE; eluted twice
with ethyl acetate:hexane (60:40, v:v).  The eluates were combined,
concentrated, and reconstituted with acetonitrile.  For samples of
broccoli and mustard greens, an aliquot was analyzed for sulfentrazone
and DMS by GC/XSD.  A second aliquot was derivatized with BSTFA
(N,O-bis[trimenthylsilyl]trifluoroacetamide) and analyzed for HMS by
GC/XSD.  For samples of cantaloupe, fruiting vegetables (pepper and
tomato), peas, flax, and strawberry and the processed commodities of
flax and tomato, the eluate was concentrated to near dryness and brought
to volume with 25% acetonitrile in water for analysis by LC/MS/MS.  For
tomato samples, the SPE cleanup steps were eliminated; after filtration,
the aqueous solution was brought to volume with water and analyzed by
LC/MS/MS.

The data-collection methods described above are adequate based on
acceptable method validation and concurrent recovery data.

860.1360 Multiresidue Methods

Residue Chemistry Memo, 2/7/95, G. Kramer

MRM data for sulfentrazone and HMS were previously submitted and
forwarded to FDA (Memo, 2/7/95, G. Kramer).  Neither compound was
recovered by any of the protocols.  The FDA PESTDATA database dated
10/99 (PAM Vol. I, Appendix II) indicates that DMS is not recovered
using MRM Sections 303 (Mills, Onley, and Gaither; Protocol E, nonfatty)
and 304 (Mills, fatty food).  No information for recovery of DMS using
Section 302 (Luke Method; Protocol D) is available.

860.1380 Storage Stability

IR-4 conducted concurrent storage stability studies with the broccoli,
cantaloupe, flax, mustard greens, pea (succulent shelled and
edible-podded), pepper, strawberry, and tomato field trials, and the
flax and tomato processing studies.  

The results indicate that residues of sulfentrazone, DMS, and HMS are
reasonably stable under frozen storage conditions in/on broccoli for 427
days, cantaloupe for 352 days, flax seed for 484 days, mustard greens
for 391 days, pea (succulent shelled and edible-podded) for 757 days,
pepper for 596 days, strawberry for 389 days, tomato and tomato paste
for 552 days, flax meal for 500 days, and flax oil for 494 days.  The
storage durations and conditions of samples from the crop field trials
submitted to support this petition are presented in Table 5.

Table 5.  Summary of Storage Conditions and Durations of Samples from 

Crop Field Trial and Processing Studies.

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

Broccoli	-38 to -3	Treated samples:

234-403 days

(7.7-13.3 months)

Control samples:

236-446 days

(7.7-14.7 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage in/on broccoli for up to 427 days.

Mustard greens	-38 to -3	Treated samples:  

104-351 days

(3.4-11.5 months)

Control samples:  

99-439 days

(3.3-14.4 months)	Residues of sulfentrazone, DMS, and HMS are stable
in/on mustard greens during frozen storage for up to 391 days.

Pea, succulent	-38 to -1	385-742 days

(12.7-24.4 months)	Residues of sulfentrazone, DMS, and HMS are stable
in/on peas stored frozen for up to 757 days.

Pepper	-40 to -2	Treated:  450-584 days

(14.8-19.2 months)

Control:  450-610 days

(14.8-20.0 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage in/on peppers for up to 596 days.

Tomato	~ -18	483-573 days

(15.9-18.8 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage in/on tomatoes for up to 552 days.

Tomato RAC	-12 (processing facility)

-18 (analytical laboratory)	506 days

 (16.6 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage in/on tomatoes and tomato paste for up to 552 days.

Tomato puree

513-519 days 

(16.9-17.1 months)

	Tomato paste

500-506 days 

(16.4-16.6 months)

	Cantaloupe 	-38 to -6	278-364  days

(9.1-12.0 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage in/on cantaloupe for up to 352 days.

Strawberry	-38 to -1	Treated samples:  

116-394 days

(3.8-13.0 months)

Control samples:  

116-434 days 

(3.8-14.3 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage in/on strawberries for up to 389 days.



Flax, seed	-38 to 0.7	354-382 days

(11.6-12.6 months)	Residues of sulfentrazone, DMS, and HMS are stable
in/on flax seed during frozen storage for up to 484 days.

Flax, seed	-29 to -14

(processing facility)

-38 to 0.7

(analytical laboratory)	Treated:  407 days

(13.4 months)

Control:  406-410 days

(13.4-13.5 months)	Residues of sulfentrazone, DMS, and HMS are stable in
frozen storage for up to 484 days in/on flax seed, 500 days in/on flax
meal, and 494 days in/on flax oil.

Flax, meal

Treated:  468 days

(15.4 months)

Control:  460-623 days

(15.1-20.5 months)

	Flax, oil

Treated:  443 days

(14.6 months)

Control:  434-624 days

(14.3-20.5 months)

	

Conclusions.  The available storage stability data for sulfentrazone are
adequate to support the storage conditions and durations of samples of
broccoli, cantaloupe, flax, mustard greens, pea (succulent shelled and
edible-podded), pepper, strawberry, and tomato from the submitted crop
field trials and the flax and tomato processing studies.  There are no
storage stability issues and no corrections for storage stability need
be applied to the field trial and processing studies.

860.1480 Meat, Milk, Poultry, and Eggs

PP#s 2F6391, 2E6498, 2E6405, & 2E6500; D287102, 1/10/03, G. Kramer

HED previously determined that, based on the established sulfentrazone
tolerances for soybean and cereal grain commodities and the results of
the livestock metabolism studies, conventional feeding studies are not
required.  This conclusion was reevaluated in conjunction with PP#s
2F6391 and 2E6405 (D287102, 1/10/03, G. Kramer) based on revised dietary
burdens resulting from a diet comprised of corn and potato commodities
for beef and dairy cattle and corn and rice commodities for poultry. 
Since a dietary exposure of 10x would not result in quantifiable
residues, HED concluded that conventional ruminant and poultry feeding
studies were still not required.

In the current petition, the only livestock feedstuff is flax meal. 
Flax meal is a feed commodity for cattle and swine (10% of diet) and
poultry (30% of diet), but would contribute a minor percentage to
livestock diets compared to soybeans and cereal grains.  Residues of
sulfentrazone and its metabolites in/on flax will not result in a higher
dietary burden, and tolerances for residues in/on meat, milk, poultry,
and egg are not required to support preemergence uses on flax.

860.1500 Crop Field Trials

Vegetable, tuberous and corm, subgroup 1C

PP#s 2F6391, 2E6498, 2E6405, & 2E6500; D287102, 1/10/03, G. Kramer

No new tuberous and corm vegetable field trial data were submitted.  An
individual tolerance has been established for the combined residues of
sulfentrazone and its metabolites HMS and DMS in/on potato at 0.15 ppm
[40 CFR §180.498(a)(2)].  Since potato is the representative commodity
for the tuberous and corm vegetable, subgroup 1C, IR-4 is proposing to
convert the individual tolerance for potato to a crop subgroup 1C
tolerance at the same level.

The available potato field trial data (MRID 45582201) were reviewed in
conjunction with PP#2E6405.  Fourteen potato field trials were conducted
in WA (3 trials), ID (2 trials), ME, FL, NC, OH, CO, ND, NJ, NY, and CA
at seasonal application rates of 0.375 lb ai/A (1x the maximum proposed
seasonal rate) with PHIs of 68-158 days.  The maximum combined residues
of sulfentrazone and its metabolites HMS and DMS were 0.077 ppm in/on
treated potato tubers.

Conclusions.  The previously submitted residue data for potato are
adequate to support the proposed crop subgroup tolerance of 0.15 ppm for
tuberous and corm vegetables, subgroup 1C.

Brassica, head and stem, subgroup 5A

Broccoli

47311401.der.doc

IR-4 has submitted field trial data for sulfentrazone on broccoli, a
representative commodity of the Brassica head and stem subgroup 5A.  Six
field trials were conducted on broccoli in the United States in Zones 1
(NY; 1 trial), 6 (TX; 1 trial), 10 (CA and NM; 3 trials), and 12 (OR; 1
trial) during the 2001 growing season.  Each trial site consisted of one
untreated plot and one treated plot.  A 4 lb/gal FlC formulation of
sulfentrazone was applied as a single broadcast application to soil 72
hours prior to transplanting broccoli or to direct seeded broccoli at
the 2-4 leaf growth stage, at a rate of 0.34-0.38 lb ai/A (~0.9-1.0x the
maximum proposed seasonal rate).  The applications were made in 19-35
GPA spray volumes, without an adjuvant.  Mature broccoli was harvested
at 45 to 73-day PHIs.

Residues of sulfentrazone, DMS, and HMS were each below the LOQ (<0.05
ppm) in/on all samples of broccoli harvested 45-73 days following one
broadcast application either to soil 72 hours prior to transplanting or
to direct seeded broccoli at the 2- to 4-leaf growth stage at a rate of
0.34-0.38 lb ai/A; see Table 6.  Total sulfentrazone residues were all
<0.15 ppm in/on all treated samples of broccoli.

Table 6.  Summary of Residue Data from Broccoli Field Trials with
Sulfentrazone.

Commodity	Total Applic. Rate

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

	n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preplant/preemergence application at a maximum
rate of 0.375 lb ai/A

Sulfentrazone

Broccoli	0.34-0.38	45-73	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

DMS

Broccoli	0.34-0.38	45-73	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Broccoli	0.34-0.38	45-73	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

Total

Broccoli	0.34-0.38	45-73	12	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Varying degrees of phytotoxicity were reported at both CA trial sites
and at the NY and TX trial sites.  The petitioner indicated that treated
broccoli plants were stunted with burned, curled leaves.  Although
phytotoxicity was attributed to the test substance application, these
isolated instances of phytotoxicity did not have an adverse impact on
the residue trials.

Cabbage

PP#1E6311, DP# 276111, 12/9/02, G. Kramer

A tolerance of 0.20 ppm has been established [40 CFR §180.498(a)(2)]
for the combined residues of sulfentrazone and its metabolites HMS and
DMS in/on cabbage based on residue data reviewed in PP#1E6311.  These
data indicate that   SEQ CHAPTER \h \r 1 the combined residues of
sulfentrazone, HMS, and SCA (quantified as DMS) were <0.15-0.18 ppm and
<0.15-0.17 ppm in/on cabbage heads with and without wrapper leaves,
respectively, harvested 68-104 days following a single ground broadcast
application of the 75% DF formulation at 0.375 lb ai/A (1x rate) made
1-3 days prior to transplanting or at the 2- to 4-leaf growth stage (33
days after planting) to direct seeded cabbage.  The petition review
concluded that two additional cabbage field trials should be conducted
in Regions 1 and 8 as a condition for full registration.

Conclusions:  The submitted residue data for broccoli along with the
previously reviewed data for cabbage are adequate to support the
proposed crop subgroup tolerance of 0.20 ppm for Brassica head and stem,
subgroup 5A.  Following application of a representative formulation of
sulfentrazone at 1x, the combined residues of sulfentrazone, DMS, and
HMS were <0.15 ppm in/on broccoli, <0.15-0.18 ppm in/on cabbage heads
with wrapper leaves, and <0.15-0.17 ppm in/on cabbage heads without
wrapper leaves.  As a condition for full registration, HED previously
required two additional cabbage field trials to be conducted in Regions
1 and 8.  These trials are no longer needed since an adequate number of
broccoli and cabbage field trials are available to satisfy geographic
representation for head and stem Brassica, subgroup 5A. 

Brassica, leafy greens, subgroup 5B

Mustard Greens

47311402.der.doc

IR-4 has submitted field trial data for sulfentrazone on mustard greens,
the representative commodity of the Brassica leafy greens subgroup 5B. 
Seven field trials were conducted on mustard greens in the United States
in Zones 2 (GA and NJ; 2 trials), 3 (FL; 1 trial), 4 (TN; 1 trial), 5
(OH; 1 trial), 6 (TX; 1 trial), and 10 (CA; 1 trial) during the
2001-2002 growing seasons.  Each trial consisted of one untreated plot
and two treated plots, except for one trial (TN) which contained three
treated plots.  Each treated plot received a single preemergence
broadcast soil application of a 4 lb/gal FlC formulation of
sulfentrazone at target rates of ~0.10 lb ai/A (~0.3x; Treatment Plot
2), ~0.20 lb ai/A (~0.5x; Treatment Plot 3) or ~0.40 lb ai/A (~1.1x;
Treatment Plot 4).  All applications were made in 20-40 GPA spray
volumes, without an adjuvant.  Mature samples were collected 40-66 days
after treatment.

The results of the field trials indicate that residues of sulfentrazone
were all below the LOQ (<0.05 ppm) in/on all samples of mustard greens
harvested 40-66 days following a preemergence broadcast soil application
of a 4 lb/gal FlC formulation of sulfentrazone at a rate of ~0.10 lb
ai/A (Treatment Plot 2), ~0.20 lb ai/A (Treatment Plot 3) or ~0.40 lb
ai/A (Treatment Plot 4); see Table 7.  Maximum residues of DMS were
0.098 ppm, 0.136 ppm, and <0.05 ppm in/on mustard green samples from
Treatment Plots 2, 3, and 4, respectively.  Maximum residues of HMS were
0.051 ppm, 0.162 ppm, and <0.05 ppm in/on mustard green samples from
Treatment Plots 2, 3, and 4, respectively.  Maximum total residues were
0.198 ppm, 0.291 ppm, and <0.15 ppm in/on mustard green samples from
Treatment Plots 2, 3, and 4, respectively.

Table 7.  Summary of Residue Data from Mustard Green Field Trials with
Sulfentrazone.

Commodity	PHI

(days)

	Trt Plot

No.	Total

Applic.

Rate

(lb ai/A)	Residue Levels (ppm)

n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preplant/preemergence application at a maximum
rate of 0.375 lb ai/A

Sulfentrazone

Mustard greens, leaves	40-66	2	0.092-0.108	14	<0.05	<0.05	<0.05	<0.05
<0.05	--

3	0.199-0.222	14	<0.05	<0.05	<0.05	<0.05	<0.05	--

4	0.402	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

DMS

Mustard greens, leaves	40-66	2	0.092-0.108	14	<0.05	0.098	0.074	<0.05
0.053	0.013

3	0.199-0.222	14	<0.05	0.136	0.109	<0.05	0.058	0.024

4	0.402	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Mustard greens, leaves	40-66	2	0.092-0.108	14	<0.05	0.051	0.051	<0.05
<0.050	0.000

3	0.199-0.222	14	<0.05	0.162	0.148	<0.05	0.070	0.037

4	0.402	2	<0.05	<0.05	0.05	<0.05	<0.05	--

Total

Mustard greens, leaves	40-66	2	0.092-0.108	14	<0.15	<0.198	0.174	<0.15
0.154	0.013

3	0.199-0.222	14	<0.15	<0.291	0.248	<0.15	0.178	0.049

4	0.402	2	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Varying degrees of phytotoxicity were reported at the FL and GA trial
sites.  The petitioner noted that crops were stunted by 15% (Treatment
Plot 2) and 75% (Treatment Plot 3) at the GA trial site and 20%
(Treatment Plot 2) and 45% (Treatment Plot 3) at the FL site.  Although
phytotoxicity was attributed to the test substance application, these
isolated instances of phytotoxicity did not have an adverse impact on
the residue trials.

Conclusions:  The submitted residue data for mustard greens, which is
the representative commodity of Brassica leafy greens, subgroup 5B, are
adequate to fulfill data requirements provided the use directions are
revised to indicate a maximum single and seasonal application rate of
0.20 lb ai/A.  The number and locations of crop field trials are in
accordance with OPPTS Guideline 860.1500 and the trials conducted
reflect the revised proposed use pattern.  The residue data for mustard
greens indicate that total residues were <0.15 ppm in/on two samples
treated at 0.402 lb ai/A (~1.1x).  It is noted that higher residues were
observed on samples treated at <1.0x.  Maximum total residues of <0.198
ppm and <0.291 ppm were reported in/on samples treated at ~0.3x and
~0.5x.  The residue data for mustard greens were not entered into the
Agency’s tolerance spreadsheet as specified by the Guidance for
Setting Pesticide Tolerances Based on Field Trial Data SOP to determine
the tolerance level as more than half of the samples (8 of 14) had
residues that were less then the LOQ (0.05 ppm).  HED concludes a
tolerance level of 0.40 ppm for free and conjugated residues of
sulfentrazone, HMS and DMS in/on Brassica leafy greens, subgroup 5B.  A
revised Section F is required.

Vegetable, Legume, Group 6

Pea, succulent

47311406.der.doc

IR-4 has submitted field trial data for sulfentrazone on succulent
shelled and edible-podded peas.  Eleven pea field trials were conducted
in the United States during the 2003-2004 growing seasons.  Eight field
trials were conducted on succulent shelled peas in Zones 1 (NY; 1
trial), 5 (MI, OH, and WI; 4 trials), 11 (ID and WA; 2 trials), and 12
(OR; 1 trial).  Three edible-podded pea trials were conducted in Zones 2
(NJ; 1 trial) and 10 (CA; 2 trials).  Each trial consisted of one
untreated plot and two treated plots.  Each treated plot received a
single preemergence broadcast soil application of a 75% DF formulation
of sulfentrazone at a rate of ~0.1875 lb ai/A (1x; Treatment Plot 2), or
~0.25 lb ai/A (1.3x; Treatment Plot 3).  All applications were made in
20-38 GPA spray volumes, without an adjuvant.  Mature peas were
collected from treatment plots at 52- to 168-day PHIs.

The results of the field trials show that residues of sulfentrazone,
DMS, and HMS were each below the LOQ (<0.05 ppm) in/on samples of peas
(succulent shelled and edible-podded) harvested 52-168 days after a
single preemergence broadcast application of a 75% DF formulation of
sulfentrazone made to soil at target rates of ~0.1875 lb ai/A (1x;
Treatment Plot 2) or ~0.25 lb ai/A (1.3x; Treatment Plot 3); see Table
8.  Total sulfentrazone residues were <0.15 ppm in/on all treated
samples of succulent shelled and edible-podded peas.



Table 8.  Summary of Residue Data from Succulent Pea Field Trials with
Sulfentrazone.

Commodity	PHI

(days)

	Trt

No.	Total

Applic.

Rate 

(lb ai/A)	Residue Levels (ppm)

n	Min.	Max.	HAFT	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preemergence application at a maximum rate of
0.1875 lb ai/A

Sulfentrazone

Pea, succulent shelled and edible-podded	52-168	2	0.181-0.198	22	<0.05
<0.05	<0.05	<0.05	<0.05	--

3	0.242-0.264	22	<0.05	<0.05	<0.05	<0.05	<0.05	--

DMS

Pea, succulent shelled and edible-podded	52-168	2	0.181-0.198	22	<0.05
<0.05	<0.05	<0.05	<0.05	--

3	0.242-0.264	22	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Pea, succulent shelled and edible-podded	52-168	2	0.181-0.198	22	<0.05
<0.05	<0.05	<0.05	<0.05	--

3	0.242-0.264	22	<0.05	<0.05	<0.05	<0.05	<0.05	--

Total

Pea, succulent

shelled and edible-podded	52-168	2	0.181-0.198	22	<0.15	<0.15	<0.15
<0.15	<0.15	--

3	0.242-0.264	22	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Varying degrees of phytotoxicity were reported at five of the trial
sites.  The petitioner reported the following phytotoxic effects:  (i)
at the NY and OH trials, stunting with slight yellowing which increased
with treatment rate, (ii) at the NJ site, whitening and yellowing of
foliage in 20% of plants, (iii) at one CA site crop stunting with lower
leaf burning of 50-75% of crops.  No phytotoxic effects were noted at
the six remaining trials.  Although phytotoxicity was attributed to the
test substance application, these isolated instances of phytotoxicity
did not have an adverse impact on the residue trials.

Conclusions:  The submitted residue data for succulent peas are adequate
to fulfill data requirements.  The number and locations of crop field
trials are in accordance with OPPTS Guideline 860.1500, and the trials
conducted reflect the proposed use pattern.  The field trial data will
support a tolerance of 0.15 ppm for succulent peas.  The combined
residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature peas
(succulent shelled and edible-podded) following treatment according to
the proposed use pattern.  A revised Section F is required since the
petitioner has proposed a tolerance level of 0.05 ppm for residues in/on
mature peas (succulent shelled and edible-podded).

Vegetable, fruiting, group 8

47311404.der.doc (includes MRID 47311405)

IR-4 has submitted field trial data for sulfentrazone on peppers (bell
and non-bell) and tomatoes, the representative commodities of the
fruiting vegetables, crop group 8.  Twenty-four fruiting vegetable field
trials were conducted in the United States during the 2004 growing
season.  Six bell pepper trials were conducted in Zones 2 (MD; 1 trial),
3 (FL; 1 trial), 5 (WI; 1 trial), 6 (TX; 1 trial), and 10 (CA; 2
trials).  Four non-bell pepper trials were conducted in Zones 2 (GA; 1
trial), 5 (WI; 1 trial), 6 (TX; 1 trial), and 10 (NM; 1 trial). 
Fourteen tomato trials were conducted in Zones 1 (NY; 1 trial), 2 (MD
and NC; 2 trials), 3 (FL; 2 trials), 5 (MI; 1 trial), and 10 (CA and NM;
8 trials).

Each trial consisted of one untreated plot and multiple (at least two)
treatment plots.  Each treatment plot received one banded application to
the soil surface made at pre-transplant stage followed by one
postemergence application between rows using a shielded/hooded sprayer. 
Treatment Plots 2, 3, and 4 were treated with a 4 lb/gal FlC formulation
whereas Treatment Plots 5 and 6 were treated with a 75% DF formulation
of sulfentrazone.  Treatment Plots 2 and 5 received two applications at
~0.250 lb ai/A for a total rate of ~0.500 lb ai/A (1.3x).  Treatment
Plots 3 and 6 received two applications at ~0.375 lb ai/A for a total
rate of ~0.750 lb ai/A (2.0x).  Treatment Plot 4 received two
applications at ~0.200 lb ai/A for a total rate of ~0.400 lb ai/A
(1.1x).  Peppers were treated at a 47- to 84-day RTI, and tomatoes were
treated at a 34- to 99-day RTI.  The second application made to each
tomato treated plot at the MD site was over-applied by ~64%.  Mature
peppers and tomatoes were collected at 19- to 22-day PHIs.

The crop field study shows that residues of sulfentrazone, DMS, and HMS
were each <LOQ (<0.05 ppm) in/on all samples of peppers and tomatoes
harvested 19-22 days following the last of two applications (a soil
surface, pre-transplant, banded application followed by a postemergence
application made between rows with a shielded/hooded sprayer) of either
a 4 lb/gal FlC formulation or a 75% DF formulation of sulfentrazone, at
total rates of 0.40 lb ai/A (1.1x), 0.50 lb ai/A (1.3x), and 0.75 lb
ai/A (2.0x); see Table 9.  Total combined residues of sulfentrazone,
DMS, and HMS were all <0.15 ppm in/on all treated samples of peppers and
tomatoes.  No residue decline data were submitted; however, decline data
are not required because residues were nonquantifiable at the earliest
harvest time.

Table 9.   Summary of Residue Data from Fruiting Vegetable Field Trials
with Sulfentrazone.

Commodity	PHI

(days)

	Trt Plot

No.	Total

Applic.

Rate

(lb ai/A)	Residue Levels (ppm)

n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preplant or postemergence application at a
maximum seasonal rate of 0.375 lb ai/A

Sulfentrazone

Bell Pepper	19-21	2	0.505-0.512	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.739-0.773	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

	21	4	0.410	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

5	0.504-0.507	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

6	0.758-0.779	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

Non-bell pepper	19-22	2	0.499-0.505	8	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.750-0.761	8	<0.05	<0.05	<0.05	<0.05	<0.05	--

Tomato	19-21	2	0.489-1.004	28	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.730-0.982	28	<0.05	<0.05	<0.05	<0.05	<0.05	--

	21	4	0.537	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

	19-21	5	0.490-0.504	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

6	0.739-0.758	4	<0.05	<0.05	<0.05	<0.05	<0.05	--



DMS

Bell Pepper	19-21	2	0.505-0.512	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.739-0.773	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

	21	4	0.410	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

5	0.504-0.507	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

6	0.758-0.779	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

Non-bell pepper	19-22	2	0.499-0.505	8	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.750-0.761	8	<0.05	<0.05	<0.05	<0.05	<0.05	--

Tomato	19-21	2	0.489-1.004	28	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.730-0.982	28	<0.05	<0.05	<0.05	<0.05	<0.05	--

	21	4	0.537	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

	19-21	5	0.490-0.504	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

6	0.739-0.758	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Bell Pepper	19-21	2	0.505-0.512	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.739-0.773	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

	21	4	0.410	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

5	0.504-0.507	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

6	0.758-0.779	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

Non-bell pepper	19-22	2	0.499-0.505	8	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.750-0.761	8	<0.05	<0.05	<0.05	<0.05	<0.05	--

Tomato	19-21	2	0.489-1.004	28	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.730-0.982	28	<0.05	<0.05	<0.05	<0.05	<0.05	--

	21	4	0.537	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

	19-21	5	0.490-0.504	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

6	0.739-0.758	4	<0.05	<0.05	<0.05	<0.05	<0.05	--

Total

Bell Pepper	19-21	2	0.505-0.512	12	<0.15	<0.15	<0.15	<0.15	<0.15	--

3	0.739-0.773	12	<0.15	<0.15	<0.15	<0.15	<0.15	--

	21	4	0.410	2	<0.15	<0.15	<0.15	<0.15	<0.15	--

5	0.504-0.507	4	<0.15	<0.15	<0.15	<0.15	<0.15	--

6	0.758-0.779	4	<0.15	<0.15	<0.15	<0.15	<0.15	--

Non-bell pepper	19-22	2	0.499-0.505	8	<0.15	<0.15	<0.15	<0.15	<0.15	--

3	0.750-0.761	8	<0.15	<0.15	<0.15	<0.15	<0.15	--

Tomato	19-21	2	0.489-1.004	28	<0.15	<0.15	<0.15	<0.15	<0.15	--

3	0.730-0.982	28	<0.15	<0.15	<0.15	<0.15	<0.15	--

	21	4	0.537	2	<0.15	<0.15	<0.15	<0.15	<0.15	--

	19-21	5	0.490-0.504	4	<0.15	<0.15	<0.15	<0.15	<0.15	--

6	0.739-0.758	4	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Conclusions:  The submitted residue data for peppers (bell and non-bell)
and tomatoes are adequate.  The number and locations of crop field
trials are in accordance with OPPTS Guideline 860.1500 and the trials
conducted reflect the proposed use pattern.  The field trial data will
support a tolerance of 0.15 ppm for residues in/on fruiting vegetables,
crop group 8.  Following two applications (a soil surface,
pre-transplant, banded application followed by a postemergence
application made between rows with a shielded/hooded sprayer) of
representative formulations at ~1.1-2.0x, the combined residues of
sulfentrazone, DMS, and HMS were <0.15 ppm in/on the representative
commodities.  A revised Section B is required to remove postemergence
uses on the labels since metabolism data are not available to support
this use pattern.  A revised Section F is also required since the
petitioner has proposed a crop group tolerance level of 0.05 ppm.

Okra

Okra residue data were not submitted in support the proposed use on
okra.  IR-4 has proposed to translate the existing and submitted
fruiting vegetable data (peppers and tomatoes) to okra.  The proposed
use on okra is identical to the proposed use on the fruiting vegetables
crop group.  HED has approved adding okra to the fruiting vegetable crop
group (see minutes of ChemSAC meeting of 10/18/06).  Until 40 CFR
§180.41 is updated, a separate tolerance must be established for
residues in/on okra.

Conclusions.  The available data for the fruiting vegetables, crop group
8 may used to support the proposed tolerance for residues in/on okra. 
The tolerance should be established at the same level as the fruiting
vegetable group tolerance, 0.15 ppm.

Melon subgroup 9A

47311403.der.doc

IR-4 has submitted field trial data for sulfentrazone on cantaloupe, the
representative commodity of the melon subgroup 9A.  Eight field trials
were conducted on cantaloupe in the United States in Zones 1 (NY; 1
trial), 2 (NC; 1 trial), 5 (WI; 1 trial), 6 (TX; 1 trial), 9 (CO; 1
trial), and 10 (CA and NM; 3 trials) during the 2002 growing season. 
Each trial consisted of one untreated plot and two treated plots, except
for one trial (NY) which had three treated plots.  Each treated plot
received a single broadcast application of a 75% DF formulation of
sulfentrazone to soil surface at pre-transplant or preemergence at rates
of ~0.20 lb ai/A (0.8x; Treatment Plot 2), ~0.25 lb ai/A (1.0x;
Treatment Plot 3) or ~0.15 lb ai/A (0.6x; Treatment Plot 4). 
Applications were made in 21-42 GPA, without an adjuvant.  Mature
cantaloupes were collected from the fields at 59- to 94-day PHIs.

The results of the field trials indicate that residues of sulfentrazone,
DMS, and HMS were below the LOQ (<0.05 ppm) in/on all samples of
cantaloupe harvested 59-94 days after a single broadcast application of
a 75% DF formulation of sulfentrazone to soil surface at pre-transplant
or preemergence at rates of ~0.20 lb ai/A (Treatment Plot 2), ~0.25 lb
ai/A (Treatment Plot 3) or ~0.15 lb ai/A (Treatment Plot 4), with one
exception; see Table 10.  In one CA trial, residues of HMS were 0.052
ppm in/on cantaloupe samples from Treatment Plot 2.  Maximum total
residues were <0.152 ppm, <0.15 ppm, and <0.15 ppm in/on cantaloupes
from Treatment Plots 2, 3, and 4, respectively.



Table 10.  Summary of Residue Data from Cantaloupe Field Trials with
Sulfentrazone.

Commodity	PHI

(days)

	Trt

No.	Total

Applic.

Rate

(lb ai/A)	Residue Levels (ppm)

n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preemergence application at a maximum seasonal
rate of 0.25 lb ai/A

Sulfentrazone

Cantaloupe, fruit	59-94	2	0.20-0.22	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.25-0.27	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

4	0.16	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

DMS

Cantaloupe, fruit	59-94	2	0.20-0.22	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

3	0.25-0.27	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

4	0.16	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Cantaloupe, fruit	59-94	2	0.20-0.22	16	<0.05	0.052	0.051	<0.05	<0.05	--

3	0.25-0.27	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

4	0.16	2	<0.05	<0.05	<0.05	<0.05	<0.05	--

Total

Cantaloupe, fruit	59-94	2	0.20-0.22	16	<0.15	<0.152	<0.151	<0.15	<0.15
--

3	0.25-0.27	16	<0.15	<0.15	<0.15	<0.15	<0.15	--

4	0.16	2	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Varying degrees of phytotoxicity were reported at four trial sites (CA;
2 trials, NC, and NY).  The petitioner noted that leaf crinkling,
necrosis, and stunted growth were observed in crops at the NY site,
crops from the NC site had marginal and intervenal necrosis, and crops
from two CA trials were reported to have stunted growth, leaf
discoloration, burning, and distortion.  Although phytotoxicity was
attributed to the test substance application, these isolated instances
of phytotoxicity did not have an adverse impact on the residue trials.

Conclusions:  The submitted residue data for cantaloupes are adequate to
support a tolerance of 0.15 ppm for residues in/on the melon subgroup
9A.  The number and locations of crop field trials are in accordance
with OPPTS Guideline 860.1500, and the trials conducted reflect the
proposed use pattern.  Following pre-transplant or preemergence
application of a representative formulation at ~0.6-1.0x, the combined
residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature
cantaloupes.  A revised Section F is required since the petitioner has
proposed a crop subgroup tolerance level of 0.10 ppm.

Strawberry

47311408.der.doc

IR-4 has submitted field trial data for sulfentrazone on strawberry. 
Eight strawberry field trials were conducted in the United States during
the 2003 growing season.  Three perennial strawberry trials were
conducted in Zones 2 (NJ; 1 trial), 5 (MI; 1 trial), and 12 (OR; 1
trial).  Five annual strawberry trials were conducted in Zones 3 (FL; 2
trials), and 10 (CA; 3 trials).  Each trial site consisted of one
untreated plot and two treated plots.  Each treated plot received one
broadcast soil application of a 75% DF formulation of sulfentrazone at
pre-plant (annual strawberry crops) or during the dormant phase
(perennial strawberry crops) at a rate of 0.25-0.26 lb ai/A (1.0x;
Treatment Plot 2) or 0.38-0.40 lb ai/A (1.6x; Treatment Plot 3), in
20-35 GPA spray volumes, without an adjuvant.  Mature strawberries were
harvested at 56-to 189-day PHIs.

The results of the field trials show that residues of sulfentrazone,
DMS, and HMS were each <LOQ (0.05 ppm) in/on all samples of strawberry
harvested 56-189 days following a single broadcast soil application of a
75% DF formulation of sulfentrazone made preplant (annual strawberry
crops) or during the dormant phase (perennial strawberry crops) at a
rate of 0.25-0.26 lb ai/A (Treatment Plot 2) or 0.38-0.40 lb ai/A
(Treatment Plot 3); see Table 11.  Total sulfentrazone residues were
<0.15 ppm in/on all treated samples of strawberry.

Table 11.  Summary of Residue Data from Strawberry Field Trials with
Sulfentrazone.

Commodity	Total Applic. Rate

(lb ai/A)	PHI

(days)	Residue Levels  (ppm)

	n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preemergence application at a maximum seasonal
rate of 0.25 lb ai/A

Sulfentrazone

Strawberry	0.25-0.26	56-189	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

	0.38-0.40

16	<0.05	<0.05	<0.05	<0.05	<0.05	--

DMS

Strawberry	0.25-0.26	56-189	16	<0.05	<0.05	<0.05	<0.05	<0.05	--

	0.38-0.40

16	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Strawberry	0.25-0.26	56-189	16	<0.05	<0.05	0.05	0.05	<0.05	--

	0.38-0.40

16	<0.05	<0.05	0.05	0.05	<0.05	--

Total

Strawberry	0.25-0.26	56-189	16	<0.15	<0.15	<0.15	<0.15	<0.15	--

	0.38-0.40

16	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Varying degrees of phytotoxicity were reported at the MI trial site and
two CA trial sites.  At the MI trial site, there was a 25-30% reduction
in size in Treatment Plot 2 and a 40% reduction Treatment Plot 3.  At
the Salinas, CA trial, a few weeks after application, there were signs
of phytotoxicity in both treated plots, with the Treatment Plot 3 being
more affected.  By the end of the growing season, the Treatment Plot 2
plants were stunted with 5-8% dead or missing plants and the Treatment
Plot 3 was 25-30% dead, with the remainder 25% stunted, producing little
or no fruit.  At the Watsonville, CA trial, a few weeks after
application, there were signs of similar levels of phytotoxicity in both
treated plots.  By the end of the growing season, the treated plots had
fewer plants with fruit than the control plot and no mature berries.  In
addition, the plants were not uniform.  Treatment Plot 3 also had many
small plants throughout the plot.  No phytotoxic effects were noted at
the five remaining trials.

Conclusions:  The submitted residue data for strawberries are adequate
to fulfill data requirements.  The number and locations of crop field
trials are in accordance with OPPTS Guideline 860.1500, and the trials
conducted reflect the proposed use pattern.  The field trial data
support a tolerance of 0.15 ppm for residues in/on strawberry.  The
combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on
mature strawberries following a pre-plant or dormant application of a
representative sulfentrazone formulation at 1.0-1.6x.  A revised Section
F is required since the petitioner has proposed a tolerance level of
0.05 ppm for residues in/on strawberries.

Flax

47311407.de1.doc

IR-4 has submitted field trial data for sulfentrazone on flax.  Six flax
field trials were conducted in the United States in Zones 5 (ND; 3
trials) and 7 (SD; 3 trials) during the 2002 growing season.  Each trial
consisted of one untreated and one treated plot.  The treated plots
received a single preemergence broadcast soil application of a 75% DF
formulation or a mixture of two 75% DF formulations of sulfentrazone at
a rate of ~0.375 lb ai/A (1.0x), in 18-20 GPA spray volumes, without an
adjuvant.  Flax seed was harvested at 111-to 123-day PHIs.

The results of the field trials indicate that residues of sulfentrazone,
DMS, and HMS were each <LOQ (0.05 ppm) in/on all samples of flax seed
harvested 111-123 days after a single preemergence broadcast soil
application of a 75% DF formulation or mixture of two 75% DF
formulations of sulfentrazone at a rate of ~0.375 lb ai/A; see Table 12.
 Total sulfentrazone residues were <0.15 ppm in/on all treated samples
of flax seed.

Table 12.  Summary of Residue Data from Flax Field Trials with
Sulfentrazone.

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

	n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Proposed Use Pattern:  Preemergence application at a maximum seasonal
rate of 0.375 lb ai/A

Sulfentrazone

Flax, seed	0.365-0.383	111-123	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

DMS

Flax, seed	0.365-0.383	111-123	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

HMS

Flax, seed	0.365-0.383	111-123	12	<0.05	<0.05	<0.05	<0.05	<0.05	--

Total

Flax, seed	0.365-0.383	111-123	12	<0.15	<0.15	<0.15	<0.15	<0.15	--

1  HAFT = highest-average field trial.  For calculation of the total
residues, HAFT, median, and mean, the LOQ value (<0.05 ppm) was used for
all residues reported as below the LOQ.

Conclusions:  The submitted residue data for flax are adequate to
fulfill the data requirements.  The number and locations of crop field
trials are in accordance with OPPTS Guideline 860.1500, and the trials
conducted reflect the proposed use pattern.  The field trial data will
support a tolerance of 0.15 ppm for residues in/on flax seed.  The
combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on
flax seed following a preemergence application of a representative
sulfentrazone formulation at 1.0x.  A revised Section F is required
since the petitioner has proposed a tolerance for residues in/on flax
seed at 0.05 ppm.

860.1520 Processed Food and Feed

Flax

47311407.de2.doc

IR-4 has submitted processing data for sulfentrazone on flax.  In one
trial conducted in ND during the 2002 growing season, flax seed was
harvested 123 days following a single preemergence broadcast soil
application of a 75% DF formulation of sulfentrazone at a rate of 0.3718
lb ai/A (~1x), without an adjuvant.  The harvested flax seeds were
processed into meal and oil using simulated commercial processing
procedures.

The processing study indicates that all residues of sulfentrazone, DMS,
and HMS were <LOQ (0.05 ppm) in flax seed (RAC), meal, and oil; see
Table 13.  Since all residues were <LOQ, processing factors (PF) could
not be calculated (NC).  It is noted that no phytotoxic effects were
reported following application of the test substance.

Table 13.  Residue Data from a Flax Processing Study with Sulfentrazone.

Processed Commodity	Total Rate

(lb ai/A) 	PHI 

(days)	Sulfentrazone	DMS	HMS	Total

	Residues 

(ppm)	PF	Residues 

(ppm)	PF	Residues 

(ppm)	PF	Residues 

(ppm)	PF

Flax, seed (RAC)	0.3718	123	<0.05	--	<0.05	--	<0.05	--	<0.15	--

Flax, meal

	<0.05	NC	<0.05	NC	<0.05	NC	<0.15	NC

Flax, oil

	<0.05	NC	<0.05	NC	<0.05	NC	<0.15	NC

Conclusions:  The submitted flax processing study is unacceptable for
regulatory purposes since the study has not conclusively demonstrated
that sulfentrazone residues of concern will not concentrate in flax meal
and oil as a result of the proposed use.  Quantifiable residues were not
detected in the flax seeds used for processing, and the field trial was
conducted at only a 1x rate.  Since no phytotoxic effects were reported,
the flax processing study needs to be repeated using an exaggerated
application rate (equal to the maximum theoretical concentration factor
for flax or 5x, whichever is less).

Tomato

47311405.der.doc

IR-4 has submitted the results of a tomato processing study with
sulfentrazone.  Samples used for processing were generated from a field
trial conducted in CA during the 2004 growing season.  Tomatoes were
harvested 20 days following two applications (one banded application to
soil surface pre-transplant and one postemergence application between
rows using a shielded/hooded sprayer) of a 4 lb/gal flowable concentrate
(FlC) formulation of sulfentrazone, applied at rates of ~0.250 lb
ai/A/application, for a total rate of ~0.500 lb ai/A (~1.3x; Treatment
Plot 2) or at ~0.375 lb ai/A/application, for a total rate of ~0.750 lb
ai/A (2.0x; Treatment Plot 3).  Applications were made at a 99-day RTI,
in 25-31 GPA spray volumes, without an adjuvant.  The collected tomato
samples were processed into paste and puree using simulated commercial
procedures.

The processing study indicates that all residues of sulfentrazone, DMS,
and HMS were <LOQ (<0.05 ppm) in/on tomato fruit, paste, and puree; see
Table 14.  Since all residues were <LOQ, processing factors could not be
calculated.  The study reported that phytotoxic effects occurred after
the first application but the crops fully recovered by the second
application.  The maximum theoretical concentration factors are 5.5x for
processing to tomato paste (OPPTS 860.1520,  Table 1).

Table 14.  Residue Data from a Tomato Processing Study with
Sulfentrazone.

Processed Commodity	Total Rate

(lb ai/A) 	PHI 

(days)	Sulfentrazone	DMS	HMS	Total

	Residues 

(ppm)	PF	Residues 

(ppm)	PF	Residues 

(ppm)	PF	Residues 

(ppm)	PF

Tomato, fruit (RAC)	0.5006	20	<0.05

<0.05	--	<0.05

<0.05	--	<0.05

<0.05	--	<0.15

<0.15	--

	0.7607

<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.15

<0.15	NC

NC

Tomato, paste	0.5006

<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.15

<0.15	NC

NC

	0.7607

<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.15

<0.15	NC

NC

Tomato, puree	0.5006

<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.15

<0.15	NC

NC

	0.7607

<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.05

<0.05	NC

NC	<0.15

<0.15	NC

NC

1  For calculation of the total residues, the LOQ value (<0.05 ppm) was
used for all residues reported as below the LOQ.

Conclusions:  The submitted tomato processing study is unacceptable
since the study does not conclusively demonstrated that sulfentrazone
residues of concern will not concentrate in tomato paste and puree as a
result of the proposed use.  Although the petitioner reported phytotoxic
effects after the first application, these plants recovered by the
second application.  Therefore, an attempt should be made to apply
sulfentrazone at an exaggerated rate (equal to the maximum theoretical
concentration factor or 5x, whichever is less) to obtain samples with
quantifiable residues so that processing factors may be determined.

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

Analytical standards for sulfentrazone and its metabolites DMS and HMS
are currently available at the EPA National Pesticide Standards
Repository (personal communication with Dallas Wright, ACB, 4/21/08). 
However, the standards for sulfentrazone and its metabolite DMS will
expire 10/1/2012 and 5/1/2012, respectively, and the standard for its
metabolite HMS has expired 4/1/2008.  The registrant must either
recertify the lot in the repository and send an updated certificate of
analysis (COA), or submit new standards (different lot #) if the
previous lots will not be recertified.  If new COAs are being submitted,
they should be faxed to the repository at 410-305-2999.

If new standards are being submitted, they should be sent to the
Analytical Chemistry Lab, which is located at Fort Meade, to the
attention of either Theresa Cole or Thuy Nygen 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.)

860.1850/1900 Confined/Field Accumulation in Rotational Crops

As the 1x use rate in soybeans (0.375 lb ai/A) is ≥ the 1x use rate of
the proposed new uses, the established tolerances for indirect or
inadvertent residues of sulfentrazone and its metabolites, HMS and DMS
are adequate to support the subject petition.  The proposed rotational
crop restrictions are adequate and consistent with previous
sulfentrazone petitions.

860.1550 Proposed Tolerances

The HED Metabolism Committee has determined that the parent compound,
sulfentrazone, and the metabolite HMS are the residues of concern in
soybeans, and that sulfentrazone and the metabolites HMS and DMS are the
residues of concern in rotational crops (D226434, 6/14/96, G. Kramer). 
As the enforcement method for plant commodities determines free and
conjugated forms of the analytes, the tolerance expression should be
revised to indicate the residues of concern are the combined residues of
free and conjugated sulfentrazone, and its metabolites HMS and DMS.

Sulfentrazone   SEQ CHAPTER \h \r 1 tolerances are currently established
under 40 CFR §180.498.  A tolerance is established under 40 CFR
§180.498(a)(1) for the combined residues of sulfentrazone and its major
metabolite, HMS, in/on soybean seed at 0.05 ppm.  Permanent tolerances
are established under 40 CFR §180.498(a)(2) for the combined residues
of sulfentrazone and its metabolites HMS and DMS in/on several food
commodities; these established tolerances range from 0.15 ppm (various
plant commodities) to 0.40 ppm (peanut meal).  Time-limited tolerances
for the combined residues of sulfentrazone and its metabolites HMS and
DMS have been established under 40 CFR §180.498(b) in connection with
Section 18 Emergency Exemptions; these include tolerances for bean,
succulent seed without pod (lima bean & cowpea) at 0.1 ppm with a
12/31/07 expiration date, flax seed at 0.2 ppm with a 12/31/10
expiration date, and strawberry at 0.60 ppm with a 12/31/10 expiration
date.  Finally, tolerances are established under 40 CFR §180.498(d) for
inadvertent and indirect combined residues of sulfentrazone and its
metabolites HMS and DMS in/on cereal grain (excluding sweet corn) bran,
forage, grain, hay, hulls, stover, and straw at 0.1-0.6 ppm as a result
of the application of sulfentrazone to growing crops.

The proposed tolerance expression in the current petition should be
revised to indicate tolerances for combined residues of free and
conjugated sulfentrazone and its metabolites HMS and DMS are the
residues of concern.  

Pending submission of a revised Section F as specified in Table 15,
adequate crop field trial data have been submitted for:  broccoli, one
of the representative commodities of head and stem Brassica (subgroup
5A); provided the proposed use directions are modified, mustard greens,
the sole representative commodity of Brassica leafy greens (subgroup
5B); peas (succulent and edible-podded); bell and non-bell peppers and
tomatoes, the representative commodities of fruiting vegetables (group
8); cantaloupe, the sole representative commodity of melon subgroup
(subgroup 9A); strawberries; and flax.  The submitted data showed that
the combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm
in/on mature commodities listed above following application(s) of a
representative formulation of sulfentrazone according to the proposed
crop use pattern.  It is, however, noted that higher residues were
observed in/on mustard green samples treated at <1.0x.  The field trial
data are supported by adequate storage stability data, and no
corrections need to be applied on the observed residues.  A revised
Section B must be submitted to remove the proposed postemergence use on
fruiting vegetables.

The residue data for mustard greens were not entered into the Agency’s
tolerance spreadsheet as specified by the Guidance for Setting Pesticide
Tolerances Based on Field Trial Data SOP to determine the tolerance
level as more than half of the samples (8 of 14) had residues that were
less then the LOQ (0.05 ppm).  HED concludes a tolerance level of 0.40
ppm for combined residues of free and conjugated sulfentrazone, HMS and
DMS in/on Brassica leafy greens, subgroup 5B.  A revised Section F is
required.

The previously reviewed data for potato, the representative commodity of
tuberous and corm vegetables (subgroup 1C) may be used to support the
requested use pattern for the subgroup.  These data were submitted as
part of PP# 2E6405 (DP#s 287102, 1/10/03, G. Kramer) and showed that the
maximum combined residues of sulfentrazone and its metabolites HMS and
DMS were 0.077 ppm in/on potato tubers after a preemergence treatment at
1x.

The previously reviewed data for cabbage, another representative
commodity of head and stem Brassica (subgroup 5A) may be used to support
the requested use pattern for the subgroup.  These data were submitted
in conjunction with PP#1E6311 (DP# 276111, 12/9/02, G. Kramer) and
indicate that the combined residues of sulfentrazone, HMS, and SCA
(quantified as DMS) were <0.15-0.18 ppm and <0.15-0.17 ppm in/on cabbage
heads with and without wrapper leaves, respectively, following
application at 1x.  The petition review concluded that two additional
cabbage field trials should be conducted in Regions 1 and 8 as a
condition for full registration.  These trials are no longer needed
since an adequate number of broccoli and cabbage field trials are
available to satisfy geographic representation for head and stem
Brassica, subgroup 5A.

The submitted data for the fruiting vegetables may used to support the
proposed use on okra.

New flax and tomato processing studies are required.

No Codex, Canadian, or Mexican MRLs have been established for
sulfentrazone on the subject crops; therefore, harmonization of MRLs and
U.S. tolerances is not an issue at this time.  An International Residue
Limit (IRL) form is appended to this Summary Document and follows this
section.

A tolerance summary for sulfentrazone is presented in Table 15.

Table 15.   Tolerance Summary for Sulfentrazone.

Commodity	Proposed Tolerance (ppm)	Recommended Tolerance (ppm)	Comments

Brassica, head and stem, subgroup 5A	0.20	0.20	The established tolerance
for cabbage under 180.498(a)(2) should be removed concomitantly when the
subgroup 5A tolerance is established

Brassica, leafy greens, subgroup 5B	0.35	0.40

	Melon subgroup 9A	0.10	0.15

	Vegetable, fruiting, group 8	0.05	0.15

	Okra	0.05	0.15

	Pea, succulent	0.05	0.15

	Flax	0.05	0.15	The established time limited tolerance for flax seed
under 180.498(b) should be removed concomitantly when the permanent flax
tolerance is established.

Strawberry	0.05	0.15	The established time limited tolerance for
strawberry under 180.498(b) should be removed concomitantly when the
permanent strawberry tolerance is established.

Vegetable, tuberous and corm, subgroup 1C	0.15	0.15	Tolerance
recommendation is based on residue data translated from potato.  The
established tolerance for potato under 180.498(a)(2) should be removed
concomitantly when the subgroup 1C tolerance is established.

References

DP#:		288712

Subject:	Sulfentrazone – Briefing Memorandum for Meeting of Metabolism
Assessment Review Committee

From:		G. Kramer

To:		Y. Donovan

Dated:		3/6/03

MRID(s):	None

DP#s:		287102, 286879, 287256, 287257

Subject:	PP#s 2F6391, 2E6498, 2E6405 & 2E6500.  Sulfentrazone in/on
Dried Shelled Pea and Bean, Field Corn, Succulent Lima Bean, Potatoes
and Asparagus.  Summary of Analytical Chemistry and Residue Data.

From:		G. Kramer

To:		D. Morgan/J. Miller

Dated:		1/10/03

MRID(s):	45537402, 45567404, 45739201, 45582201, 45752601, 45567403,
45582201

DP#:		276111

Subject:	PP# 1E6311.  Sulfentrazone on Cabbage, Horseradish, and Mint. 
Evaluation of Residue Data and Analytical Methods.

From:		G. Kramer

To:		S. Brothers/R. Forrest

Dated:		12/9/02

MRID(s):	45393501 and 45393502

DP#:		233520

Subject:	PP# 4F04407.  Sulfentrazone (Authority Herbicide) for Use on
Soybeans.  Results of Petition Method Validation (PMV).

From:		G. Kramer

To:		S. Robbins/K. Boyle

Dated:		3/25/97

MRID(s):	44118801 and 44118802

DP#:		226434

Subject:	HED Metabolism Committee of 5/20/96.  Sulfentrazone. 
PP#4F04407.

From:		G. Kramer

To:		HED Metabolism Committee Members

Dated:		6/14/96

MRID(s):	None

DP#:		220548

Subject:	PP# 4F04407.  Sulfentrazone for Use on Soybeans.  Data Waiver
Request.

From:		G. Kramer

To:		J. Miller

Dated:		3/13/96

MRID(s):	None

DP#:		None

Subject:	Multiresidue Method Testing of sulfentrazone and 3-hydroxy
methyl sulfentrazone.

From:		G. Kramer

To:		H. Hundley

Dated:		2/7/95

MRID(s):	43345416

  SEQ CHAPTER \h \r 1 Attachments:  

International Residue Limit Status sheet

DOCUMENT TRACKING

RDI:  RAB1 Chemistry Team:  08/20/2008

Petition Number: 7E7308

DP#: 349321

PC Code: 129081

Template Version September 2005



INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name: 
N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,
4-triazol-1-yl]phenyl]methanesulfonamide	Common Name:  Sulfentrazone

	X Proposed tolerance

⁬Reevaluated tolerance

⁬Other	Date:  4/17/08

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

X No Codex proposal step 6 or above

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ition Number:  PP#7E7308

DP#:  349321

Other Identifier:  

Residue definition (step 8/CXL): N/A	Reviewer/Branch:  J. Tyler/RAB1

	Residue definition:  Combined residues of sulfentrazone and its
metabolites 3-hydroxymethyl sulfentrazone (HMS) and 3-desmethyl
sulfentrazone (DMS)

Crop (s)	MRL (mg/kg)	Crop(s) 	Tolerance (ppm)

Brassica, head and stem, subgroup 5A	0.20

Brassica, leafy greens, subgroup 5B	0.35

Melon, subgroup 9A	0.10

Vegetable, fruiting, group 8	0.05

Okra	0.05

Pea, succulent	0.05

Flax	0.05

Strawberry	0.05

Vegetable, tuberous and corm, subgroup 1C	0.15

Limits for Canada	Limits for Mexico

X No Limits

⁬ No Limits for the crops requested	⁬ No Limits

X No Limits for the crops requested

Residue definition:  N/A

	Residue definition: sulfentrazone

Crop(s)	MRL (mg/kg)	Crop(s)	MRL (mg/kg)

	Notes/Special Instructions:

S.Funk, 04/28/2008.

Sulfentrazone	Summary of Analytical Chemistry and Residue Data	DP#: 
349321

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