FILE NAME:   company.wpd   (1/1/2006)

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[5E7007 and 5E6962 ]

Summary of Petitions

	EPA has received pesticide petitions (5E7007 and 5E6962) from
Interregional Research Project Number 4 (IR-4), 681 U.S. Highway #1
South, North Brunswick, NJ 08902-3390; and Bayer CropScience, 2 T.W.
Alexander Drive, Research Triangle Park, NC 27709 proposing, pursuant to
section 408(d) of the Federal Food, Drug, and Cosmetic Act (FFDCA), 21
U.S.C. 346a(d), to amend 40 CFR part 180 by establishing a tolerance for
residues of isoxadifen-ethyl (ethyl
5,5-diphenyl-2-isoxazoline-3-carboxylate) and its metabolite
4,5-dihydro-5,5,diphenyl-3-isoxazolecarboxylic acid when used as an
inert ingredient (safener) in or on the following raw agricultural
commodities: corn, sweet, kernel plus cob with husks removed at 0.05
parts per million (ppm), corn, sweet, forage at 0.40 ppm, corn, sweet,
stover at 0.40 ppm, corn, pop, grain at 0.02 ppm, corn, pop, stover at
0.40 ppm, corn, field, forage at 0.20 ppm (increased from existing
tolerance of 0.10 ppm), and corn, field, stover at 0.40 ppm (increased
from existing tolerance of 0.20 ppm); and isoxadifen-ethyl and its
metabolites 4,5-dihydro-5,5,diphenyl-3-isoxazolecarboxylic acid and
β-hydroxy-β-benzenepropanenitrile when used as an inert ingredient
(safener) in or on the following raw agricultural commodities: rice,
grain at 0.10 ppm, rice, hulls at 0.50 ppm, and rice, straw at 0.25 ppm
(request removal of the specified limitation in seasonal application
rate from the existing tolerances).  EPA has determined that the
petition contains data or information regarding the elements set forth
in section 408(d)(2) of the FFDCA; however, EPA has not fully evaluated
the sufficiency of the submitted data at this time or whether the data
supports granting of the petition.  Additional data may be needed before
EPA rules on the petition.

A. Residue Chemistry                                       

.  The metabolism of isoxadifen-ethyl (ethyl 5,5-diphenyl-2-
isoxazoline-3-carboxylate) in corn and rice has been investigated and is
understood.  Total residue levels in corn commodities were very low. The
initial metabolic transformation of isoxadifen-ethyl in plants is
hydrolysis of the prominent ester function, yielding the carboxylic
acid, AE F129431 (4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylic acid),
the principal metabolite in forage, grain and stover. The pathway then
proceeds via hydroxylation of the phenyl ring to AE F162241
(4,5-dihydro-5-(4-hydroxyphenyl)-5-phenyl-3-isoxazolecarboxylic acid)
which was also significant in forage and stover. AE F129431 and AE
F162241 were also identified in a rice metabolism and rat metabolism
study.  The Agency determined that for corn only the parent
isoxadifen-ethyl and the major metabolite isoxadifen acid (AE F129431)
were the residues of concern.  In rice grain, the primary metabolite
identified was AE C637375 (3-hydroxy-3,3-diphenylpropane- nitrile),
which was found only in trace amounts. AE F129431 and its hydroxylated
analogue AE F162241 comprised the major metabolic residue in rice straw.
 AE F129431 and AE F162241 were also identified in a rice metabolism and
rat metabolism study. 

.  The analytical targets selected were the parent compound,
isoxadifen-ethyl and the major metabolite isoxadifen acid (AE F129431). 
In rice, AE C637375 and AE F162241 are also determined.  After
extraction and cleanup, the analytes are determined by either GC/MS or
HPLC/MS.  The limits of quantification (LOQ) are 0.02 ppm in corn grain,
0.05 ppm in corn forage and stover, and 0.02 ppm in rice. 

.  Four popcorn and 12 sweet corn field trials (14 'harvest'; 2
'decline') were conducted to measure the magnitude of isoxadifen-ethyl
residues on corn following treatment with a suspension concentrate
formulation nominally containing 1.75 lb isoxadifen-ethyl safener per
gallon (210 g/L).  Each trial contained one control and two treated
plots.  Two foliar spray applications of the product were made at 24
inch and 36 inch corn height to treated plot A at a target rate of 0.041
lb safener/acre/application (46 g ai/ha).  Treated plot B received one
foliar spray application at 36 inch corn height and one drop nozzle
(directed) spray one week later at the same target application rate. 
Spray volumes ranged from 13.1 to 17.4 gal/acre (122 to 163 L/ha).  The
achieved total seasonal rates ranged from 0.081 to 0.086 lb safener/acre
(91 to 96 g/ha) for all treated plots at all test sites.  

Following two foliar spray applications to sweet corn at 24 inch and 36
inch height (Treatment A) at a total seasonal target rate of 0.082 lb
safener/acre (92 g safener/ha), the total isoxadifen-ethyl derived
highest average field trial (HAFT) residue was <0.02 ppm, 0.07 ppm, and
0.35 ppm for sweet corn grain, forage, and stover, respectively.  
Maximum single residues were <0.02 for sweet corn grain, 0.07 ppm for
forage, and 0.35 ppm for stover.  Following the same treatment regimen
to popcorn, the total isoxadifen-ethyl derived HAFT residue was <0.02
for grain and 0.08 ppm for stover.  Maximum single total
isoxadifen-ethyl derived residues were <0.02 for grain and 0.10 ppm for
stover.

Following one foliar and one directed spray application to sweet corn at
36 inch height and one week later (Treatment B) at a total seasonal
target rate of 0.082 lb safener/acre (92 g safener/ha), the total
isoxadifen-ethyl derived HAFT residue was 0.02 ppm, 0.34 ppm, and 0.34
ppm for sweet corn grain, forage, and stover, respectively.  Maximum
single total isoxadifen-ethyl derived residues were 0.02 for sweet corn
grain, 0.35 ppm for forage, and 0.36 ppm for stover.   Following the
same treatment regimen to popcorn, the total isoxadifen-ethyl derived
HAFT residue was <0.02 for grain and 0.08 ppm for stover.  Maximum
single total isoxadifen-ethyl derived residues were <0.02 ppm for grain
and 0.09 ppm for stover. 

For two years (1997 and 1998) trials were conducted in field corn on
fifteen sites in the US and Canada to determine the magnitude of
isoxadifen-ethyl residues on corn following treatment with a
water-dispersible granulate formulation containing nominally 50% (w/w)
isoxadifen-ethyl.  

Each site comprised one control and four treated plots.  Three treated
plots received an application at 30 g a.i./ha followed by an application
at 60 g a.i./ha.  The application timing ranged from 12 inch corn to 48
inch corn.  The fourth treated plot in the US received a single
application of 120 g a.i./ha to 48 inch corn.  The fourth plot in Canada
was treated with two times 45 g a.i./ha.  Samples of forage were
collected 45 days after the 48 inch applications, ears alone were
sampled 70 days after the 48 inch applications, and ears and stover were
sampled at maturity.  The samples were analyzed for the parent compound
and its metabolites AE F129431 and AE F 162241.

In the 1997 trials isoxadifen derived residues in corn grain were
limited to four observations of AE F129431 at a maximum of 0.03 ppm. 
Residues in stover and forage were limited to sporadic observations of
AE F129431 and AE F162241 at or just above the limits of quantitation
(0.05 ppm).  Residues above 0.1 ppm were confined to isolated
observations of AE F129431 following the 160 g a.i./ha treatment.  A
maximum residue was observed at 0.35 ppm in stover and 0.15 ppm in
forage.  Due to the very low residue levels no decline trends could be
observed. 

In the 1998 trials isoxadifen derived residues were limited to sporadic
observations of the metabolites AE F129431 and AE F 162241 in stover
together with four observations of the metabolite AE F 129431 in grain. 
AE F129431 reached a maximum of 0.19 ppm in stover (treated with 160 g
a.i./ha) and 0.06 ppm in grain (treated with 30+60 g a.i./ha).  AE
F162241 derived residues reached a maximum of 0.1 ppm in stover (treated
with 160 g a.i./ha).  No residues above the limits of quantitation
(0.02) were found in grain treated with 160 g a.i./ha.

B. Toxicological Profile

.  Isoxadifen ethyl has low acute toxicity:  acute rat oral LD50  1740
mg/kg, acute rat dermal LD50 > 2000 mg/kg, 4 hour rat inhalation LC50
was > 5 mg/L.  Isoxadifen ethyl was slightly irritating to rabbit eyes
and non irritating to rabbit skin.  Based on these results, isoxadifen
ethyl was classified as EPA Category III for oral and dermal toxicity
and eye irritation, and EPA Category IV for inhalation toxicity and
dermal irritation.  Technical isoxadifen ethyl was shown to be a dermal
sensitizer in a guinea pig maximization assay, but no evidence of
sensitization has been observed in a Buehler assay when formulated into
a commercial product.

.  Isoxadifen-ethyl was negative in the:Ames and E. coli reverse
bacterial mutation assays,  in vitro mammalian gene mutation assay in
Chinese hamster lung (V79) cells,  in vivo unscheduled DNA synthesis
assay in rat hepatocytes, and mouse micronucleus assay.  In an in vitro
chromosomal aberrations assay in Chinese hamster lung (V79) cells,
isoxadifen-ethyl was negative without metabolic activation, but positive
with activation only at toxic concentrations.  Thus, the overall weight
of evidence indicates that isoxadifen ethyl does not possess significant
genotoxic activity.

.  Isoxadifen-ethyl is not teratogenic or a reproductive toxicant. A rat
developmental toxicity study was conducted at dose levels of  0, 15, 120
and 1000 mg/kg/day.  Maternal toxicity (including one death) was noted
at 1000 mg/kg/day, as was an increase in resorptions.  Bent scapula or
bent scapula costad were observed at a LOAEL of 120 mg/kg/day which was
a NOAEL for maternal toxicity. The maternal LOAEL was 1,000 mg/kg/day
based on mortality, decreased body weight, weight gain, and food
consumption. The developmental NOAEL was 15 mg/kg/day.  Based on this
study, EPA selected a acute Reference Dose (aRfD) for females 13-50 of
0.15 mg/kg/day.

A rabbit developmental toxicity study was conducted at dose levels of 0,
5, 50 and 500 mg/kg/day.  Maternal effects at 500 mg/kg/day consisted of
decreased food consumption, slight weight loss during gestation days 6
8,  one death, and one dam with two emply implantation sites.  Both the
maternal and developmental NOAELs were 50 mg/kg/day based on increased
mortality (dams) and fragmented caudal vertebrae (fetuses) at the same
LOAEL of 500 mg/kg/day (HDT).

In the 2 generation reproduction study in the rat, administration of
isoxadifen ethyl at 4000 ppm, resulted in parental toxicity in the F0
and F1 generation (both sexes) consisting of reduced body weight,  body
weight gain, food intake and an increase in microscopic kidney lesions.
Decreased F1 pup body weight was associated  with a delay in achievement
of vaginal patency and balanopreputial separation at 4000 ppm. The
reproductive NOAEL was $4000 ppm (HDT). The NOEL for both parental and
neonatal toxicity was 200 ppm, equivalent to an overall mean achieved
intake of about 16.4 mg/kg body weight/day.

In a 90 day rat feeding study, isoxadifen ethyl was administered at
dietary concentrations of 0, 20, 200, 2000 and 4000 ppm.  The NOEL for
this study was considered to be 200 ppm (approximately 13.8 mg/kg/day)
based on decreased body weight and body weight gain at 2000 ppm, and
decreased weight gain, increased liver weights and centrilobular
hepatocyte enlargement at 4000 ppm.  

In a 90 day feeding study in mice, isoxadifen ethyl was administered at
dietary concentrations of 13, 125, 1250 and 2500 ppm.  At the top 2 dose
levels,  decreased kidney weights, increased liver weights, and
histopathological changes in the liver (centrilobular hepatocyte
enlargement,  vacuolation and fatty deposits) were noted.  The NOEL for
this study was 125 ppm (approximately 19.8 mg/kg/day).  

In a 90 day dog feeding study,  isoxadifen ethyl was administered to
beagle dogs at dietary concentrations of 0, 25, 125 and 1000 ppm.
Dietary administration of 1000 ppm isoxadifen ethyl exceeded the maximum
tolerated dose (MTD), and it was concluded that 700 ppm would be a
suitable high dose level for a chronic dog study. The NOEL for this 90
day study was considered to be 25 ppm (approximately 1.2 mg/kg/day)
based on fat deposits in the collecting ducts of the kidney and aspermia
(males) and decreased body weight gain, differences in various
hematological parameters and moderate fat deposits in the collecting
duct of the kidneys (females).

. Chronic toxicity has been assessed in  the rat, mouse and the dogIn
the rat combined chronic toxicity and oncogenicity study the liver was
the target organ as evidenced by increases in liver weight and
centrilobular hepatocyte hypertrophy. The no effect level was 200 ppm
(10 mg/kg/day). In the mouse carcinogenicity study, the NOAEL was 16.6
mg/kg/d in males and 202.5 mg/kg/d in females, based on significantly
decreased survival in males at 169.6 mg/kg/day and females at 407.3
mg/kg/d.  There was no evidence of carcinogenicity. In the chronic dog
study, the NOAEL was 3.3 mg/kg/day (males) and 3.6 mg/kg/day(females). 
The LOAEL was 24 mg/kg/d based on increased blood creatinine in females,
decreased urinary specific gravity (both sexes), increased partial
thromboplastin time (both sexes) and increased incidence and severity of
straight tubule vacuolation in the kidney of both sexes.The dog is the
most sensitive species. Based on the dog, EPA selected a chronic
Reference Dose (cRfD) for isoxadifen ethyl of 0.033 mg/kg/day. No
carcinogenic activity was detected in dogs, mice and rats at the Maximum
Tolerated Dose (MTD). Isoxadifen ethyl is not oncogenic in dogs, rats or
mice and is not likely to be carcinogenic in humans.  Isoxadifen ethyl
was classified as a "Not likely to be a human carcinogen@ based on the
lack of carcinogenicity in rats and mice.

. The metabolism of isoxadifen-ethyl has been determined in the rat and
dog. In both species the main metabolic route was hydrolysis of the
ester to yield the free acid AE F129431
(5,5-diphenyl-2-isoxazoline-3-carboxylic acid), which is the same as
observed in plants. This was the only significant metabolic route in the
dog following either gavage or dietary dosing. In the rat there was an
additional metabolic route which led to the formation of a hydroxylated
free acid, AE F162241
(4,5-dihydro-5-(4-hydroxyphenyl)-5-phenyl-3-isoxazolecarboxylic acid),
also a plant metabolite. This was a major metabolic route in male rats,
particular at the low-dose, but was only a minor metabolic route in
female rats. Unchanged isoxadifen-ethyl was only excreted in trace
amounts in the faeces. There were a number of minor (< 3%) polar
metabolites also excreted, which were not identified. A further plant
metabolite AE C637375 ( -hydroxy- -benzenepropanenitrile) was also shown
to be a trace metabolite in the rat. 

The metabolism of isoxadifen-ethyl in ruminants is adequately
understood.  A dairy cow was dosed with the compound at a level
equivalent to 11.52 ppm in the diet for 7 days.  Total residue levels
were very low.  Parent compound was seen in fats and milk only. The
carboxylic acid, AE F129431, was the major metabolite identified in all
of the tissues, with traces also being found in the milk. 

The metabolism of isoxadifen-ethyl in poultry is also adequately
understood. Laying hens were fed the compound at a level equivalent to
11 ppm in the diet for 14 days.  Residue levels were low in all
commodities.  The vast majority of the dose was excreted as AE F129431,
with smaller amounts of AE F162241 and isoxadifen-ethyl.  AE F129431 was
the major metabolite identified in all of the tissues and yolks.  Trace
amounts of isoxadifen-ethyl and AE F162241 were detected in liver and
eggs with isoxadifen-ethyl also being detected in the muscle. The
metabolic profile of isoxadifen-ethyl in the hen was similar to that
seen in the cow and rat.

. [NA Remove.]

.  No special studies have been conducted to investigate the potential
of isoxadifen-ethyl to induce estrogenic or other endocrine effects. 
However, no evidence of estrogenic or other endocrine effects have been
noted in any of the standard toxicology studies that have been conducted
with this product and there is no reason to suspect that any such
effects would be likely. 

C. Aggregate Exposure

. Isoxadifen-ethyl will be used as a herbicide safener for use on rice
and corn, including popcorn and sweet corn, as well as on turf.  

.  Acute and chronic dietary analyses were conducted to estimate
exposure to potential isoxadifen-ethyl derived residues in/on corn,
including sweet corn and popcorn, and rice.  A Tier One analysis was
conducted using the DEEM-FCID( software and the 1994-1996, 1998 CSFII
food consumption data. It was assumed that residues were at established
and proposed tolerance levels in rice (0.1 ppm), field corn grain (0.1
ppm), popcorn grain (0.05 ppm), and sweet corn grain (0.05 ppm) and that
100% of all crop was treated. Additionally, based on the results from
appropriate studies, it was assumed that there was no concentration into
processed commodities and that contributions from residues in meat, milk
or eggs are not required. An acute RfD of 0.15 mg/kg/day for females
13-50 years old was based on the rat developmental toxicity study and an
100x uncertainty factor.  A chronic RfD of 0.033 mg/kg /day was derived
from the NOEL of 3.3 mg/kg /day in the most sensitive species, dog. 
Using these inputs the acute dietary exposure estimate for females 13-50
years old was 0.000381 mg/kg/day or 0.25 % of the aPAD.  The chronic
dietary exposure estimate from residues of isoxadifen-ethyl for the US
Population was 0.000173 mg/kg /day or 0.5% of its cPAD.  For the
sub-population with the highest exposure, children 3-5 years old, the
chronic dietary exposure estimate from residues of Isoxadifen-ethyl was
0.000394 mg/kg /day, or 1.2 % of its cPAD. These values are highly
conservative, having been based on worst case assumptions of tolerance
level residues and 100% of the crop treated.



. US EPA's Standard Operating Procedure (SOP) for Drinking Water
Exposure and Risk Assessments was used to perform the drinking water
assessment.  This SOP uses a variety of tools to conduct drinking water
assessment.   These tools include water models such as SCI-GROW, GENEEC,
PRZMS/EXAMS, and monitoring data.  If monitoring data are not available
then the models are used to predict potential residues in surface and
ground water and the highest is assumed to be the drinking water
residue.  In the case of isoxadifen-ethyl monitoring data do not exist
therefore model calculations were used to estimate a water residue.  The
calculated drinking water levels of comparison (DWLOC) for acute and
chronic exposures for all subgroups greatly exceed the estimated
drinking water concentrations from the models.  The acute DWLOC for
females 13-50 is 8977 ppb, the chronic DWLOC for adults is 1148 ppb. 
The chronic DWLOC for children/toddlers is 326 ppb.  EPA calculated
estimated environmental concentrations (EECs) for surface water of 80
and 40 ppb (acute and chronic values), and for groundwater of 5 ppb (HED
review D2296540 from 02-Dec-2003).

.  Exposure to isoxadifen-ethyl for the mixer/loader/ground boom/aerial
applicator was calculated using the Pesticide Handlers Exposure Database
(PHED) for liquid and dry flowable formulations.  It was assumed that
the product would be applied to a maximum of 200 acres per day by ground
boom applicator and 1200 acres per day by aerial applicator at a maximum
use rate of 0.71 pounds ai per acre (equivalent to 80 grams ai per
hectare).  Normal work attire consisting of long sleeved shirt, long
pants, and protective gloves were assumed in the PHED assessments. 
Short term margins of exposure (MOEs) for a 70 kg operator were
calculated utilizing an oral NOAEL of 13.8 mg/kg body weight/day from
the 90 day rat feeding study.  Intermediate term MOEs were calculated
utilizing an intermediate term NOAEL of 3.3 mg/kg body weight/day from
the dog chronic toxicity study.  A 14 % dermal absorption value was used
for all dermal exposures.  The combined short term MOEs (inhalation plus
dermal) for persons mixing, loading, and applying isoxadifen-ethyl with
open cab ground boom equipment were 9,600 and 5,400 for liquid and dry
flowable formulations, respectively.  The combined intermediate term
MOEs (inhalation plus dermal) for persons mixing, loading, and applying
isoxadifen-ethyl with open cab ground boom equipment were 2,300 and
1,300 for liquid and dry flowable formulations, respectively.  For
aerial application, where the mixer/loader was assumed to be a different
operator from the pilot, combined short term MOEs for the mixer/loader
were 2,600 and 1,100 for liquid and dry flowable formulations,
respectively.  The combined intermediate term MOEs for the mixer/loader
were 610 and 270 for liquid and dry flowable formulations, respectively.
 Combined short term and intermediate term MOEs for pilots were 15,000
and 3,500, independent of formulation type.  Post-application exposure
to workers reentering corn fields treated with isoxadifen-ethyl was
estimated using a default dislodgeable foliar residue of 20% of the
application rate and a 1000 cm2/hr transfer coefficient for scouting and
irrigation from HED Exposure SAC Policy 3.1.  An 8-hour work day, and a
70 kg worker were assumed.  The short term MOE of 5,400 was calculated
utilizing an oral NOAEL of 13.8 mg/kg body weight/day from the 90 day
rat feeding study and a 14 percent dermal absorption value.  The results
indicate no unacceptable risk for the proposed use of isoxadifen-ethyl.

Isoxadifen-ethyl may also be used on turf, which could result in
residential exposures. EPA (Federal Register / Vol. 69, No. 102 /
Wednesday, May 26, 2004, 29882 - 29890) published the following risk
assessment:  The proposed turf use is intended for professional
application to Bermudagrass on golf courses, sod farms, residential and
commercial site lawns, parks, recreational facilities, and similar
sites. It is not intended for use by homeowners or other nonprofessional
applications. Therefore, residential mixer/loader and applicator
exposures are not anticipated. The following short-term post-application
residential exposures are anticipated: Adult (dermal - golf course and
residential lawn), children (dermal -residential lawn), and toddler
(dermal and incidental oral - residential lawn). However, dermal
exposures for golfers are considered to be less than those resulting
from a residential turf application, and were therefore not assessed.
Hand to mouth (HTM), object to mouth (OTM), and soil hand to mouth
short-term incidental oral exposures may occur as a result of the
proposed turf use. However, the soil hand to mouth exposure is
considered to be very small in comparison to the other exposures. MOEs
were estimated to be 790 (for a 15 kg child) and 1,500 (for an adult).
MOEs greater than 100 are not of concern.

D. Cumulative Effects

	There is no information to indicate that isoxadifen-ethyl may share a
common mechanism of toxicity with any other chemical.  Thus, this
assessment was not needed.

E. Safety Determination

. Using the conservative assumptions described above, based on the
completeness and reliability of the toxicity data, it is concluded that
aggregate exposure, in this case food only, to the proposed uses of
isoxadifen-ethyl will utilize at most 0.5% of the reference dose for the
US Population.  The actual exposure is likely to be much less as more
realistic data and models are developed.  EPA generally has no concern
for exposures below 100% of the RfD because the RfD represents the level
at or below which daily aggregate exposure over a lifetime will not pose
appreciable risk to human health.  Drinking water levels of comparison
based on the dietary exposure are much greater than highly conservative
estimated levels, and would be expected to be well below the 100% level
of the RfD, if they occur at all.  Therefore, there is a reasonable
certainty that no harm will occur to the US Population from aggregate
exposure (food and drinking water) to isoxadifen-ethyl.

. No evidence of increased sensitivity to fetuses was noted in
developmental toxicity studies in rats or rabbits.  There has been no
indication of reproductive effects or indication of increased
sensitivity to the offspring in the 2 generation rat reproduction study.
 No additional safety factor to protect infants and children is
necessary as there is no evidence of increased sensitivity in infants
and children.

Using the conservative assumptions described in the exposure section
above, the percent of the reference dose that will be used for exposure
to residues of isoxadifen-ethyl in food for children 3-5 years old (the
most highly exposed sub group) is 1.2%.  As in the adult situation,
drinking water levels of comparison are much higher than the worst case
drinking water estimated concentrations and are expected to use well
below 100% of the reference dose, if they occur at all.  Therefore,
there is a reasonable certainty that no harm will occur to infants and
children from aggregate exposure to residues of isoxadifen-ethyl.

F. International Tolerances

	There are no Codex Alimentarius Commission (CODEX) maximum residue
levels (MRLs) established for residues of isoxadifen-ethyl.



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