 

EPA REGISTRATION DIVISION COMPANY NOTICE OF FILING FOR PESTICIDE
PETITIONS PUBLISHED IN THE FEDERAL REGISTER  

EPA Registration Division contact: [Philip V. Errico (7505C) - Office of
Pesticide Programs-U.S. Environmental Protection Agency- S7723, Office
of Pesticide Programs, One Potomac Yard, 2777 S. Crystal Dr., Arlington,
VA 22202-Phone: 703-305-6663 - Email: errico.philip@epamail.epa.gov.]

 

INSTRUCTIONS:  Please utilize this outline in preparing the pesticide
petition.  In cases where the outline element does not apply, please
insert “NA-Remove” and maintain the outline. Please do not change
the margins, font, or format in your pesticide petition. Simply replace
the instructions that appear in green, i.e., “[insert company
name],” with the information specific to your action.

TEMPLATE:

[Dow AgroSciences, LLC]

[Insert petition number]

	EPA has received a pesticide petition (PP# 8F7369) from [Dow
AgroSciences, LLC.], [9330 Zionsville Road, Indianapolis, Indiana 46268]
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.

(Options (pick one)

	1. by establishing a tolerance for residues of

	2. to establish an exemption from the requirement of a tolerance for

	[penoxsulam] in or on the raw agricultural commodity [nut, tree, group
14] at [0.01] parts per million (ppm), [grape] at [0.01] parts per
million (ppm), [almond, hulls] at [0.01] parts per million (ppm),
[pistachio] at [0.01] parts per million (ppm).  EPA has determined that
the petition contains data or information regarding the elements set
forth in section 408 (d)(2) of FDDCA; 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

	1. Plant metabolism. [Based on results of the metabolism studies in
plants that are summarized below, it is concluded that the residue
definition in plants is the parent compound alone, penoxsulam.  

A nature of residue study (NOR) was conducted in grapes using a soil
application of penoxsulam. Penoxsulam, 14C-labeled either in the
2-position on the triazolopyrimidine ring (TP) or uniformly labeled in
the phenyl-ring (Ph), was applied as a broadcast spray onto soil around
established grape vines at a single application rate of approximately 20
g a.i./ha.  The soil in this study was a sandy clay loam.  Application
was made when grapes vines were at growth stage BBCH 55 (early
flowering).  After application, the plots were irrigated with 1 cm of
water daily for 7 days.  Grapes and leaves were harvested at 118 days
after application. 

Mature grapes contained residues below the limit of quantification
(0.0008 µg/g penoxsulam equivalents).  The PH-label and TP-label leaves
collected at maturity contained 0.016 µg/g and 0.013 µg/g penoxsulam
equivalents, respectively.  In the mature leaves, approximately 65% of
the leaf TRR was extractable with neutral solvent, of which
approximately half partitioned into organic solvent.  The majority of
the organic phase was identified as numerous low-level metabolites,
while the aqueous phase consisted of primarily polar, solvent-front
residues.  The residue was characterized as low-level degradates,
tentatively including the 5-hydroxy-penoxsulam and the
dihydroxy-penoxsulam metabolites.

In summary, very low levels of soil-applied penoxsulam and degradates
are taken up by the vine.  No penoxsulam was detected in the leaves, and
due to the low TRR levels in the grapes, no penoxsulam is predicted
there either.  The residue was characterized as low-level degradates,
tentatively including the 5-hydroxy-penoxsulam and the
dihydroxy-penoxsulam metabolites.

The nature of residue study in rice, treated with 14C-labeled penoxsulam
(2-position on the triazolopyrimidine ring or uniformly labeled in the
phenyl ring) at 100 g/ha, demonstrated that no significant residues
(0.003-0.022 ppm) were found in mature straw and grain.  The residues
were fractionated by reversed-phase HPLC and consisted of penoxsulam,
5-OH penoxsulam (identified by retention time), and two unidentified
peaks.  Each component was <0.01 μg/g (penoxsulam equivalents).  Based
on the plant metabolism studies, the tolerance expression is the parent,
penoxsulam. 

Metabolism studies in livestock animals with 14C-labeled penoxsulam
(2-position on the triazolopyrimidine ring or uniformly labeled in the
phenyl ring) at a concentration equivalent to about 10 ppm in the diet
indicated that approximately 99% of the administered dose was eliminated
in the excreta.  The low levels of residues (0.002-0.07 ppm) in fat and
edible tissues, milk or eggs demonstrate that residues due to penoxsulam
would not accumulate in the animals.  Additionally, the dose levels in
these studies are about 200 to 1000 times higher than the theoretical
maximum exposure in the animal diet of rice commodities treated with
penoxsulam, therefore, livestock feeding studies are not considered
necessary. ]

	2. Analytical method. [In the Magnitude of Residue (MOR) studies
conducted in grapes, almonds and pecans to support tolerances proposed
in this petition, residues of penoxsulam  DOCVARIABLE  AI1lc  \*
MERGEFORMAT   were determined using the analytical method GRM 04.09. 
Residues of penoxsulam were extracted from the crop samples by
homogenizing and shaking with an acetonitrile/water solution (80:20
v/v).  An aliquot was diluted with 0.1N HCl and purified using a 96-well
polymeric-reverse phase extraction (SPE) plate.  The SPE plate was
washed with a 40/60 methanol/water solution and eluted with acetonitrile
into a 96-well plate containing an acetonitrile/methanol/water mobile
phase (15:15:70 containing 0.1% acetic acid) and a stable isotope
internal standard.  The final solution was analyzed by liquid
chromatography with positive-ion electrospray tandem mass spectrometry
(LC/MS/MS).  The limit of detection (LOD) and limit of quantitation
(LOQ) are 0.003 µg/g and 0.010 µg/g, respectively.]

	3. Magnitude of residues. [The proposed tolerances (Section F) are
supported by MOR studies in grapes, almonds and pecans conducted in the
U.S.  Trials were conducted in almonds and pecans to support a tolerance
for the nut tree crop group (Nuts, tree, group 14) including pistachios,
and almond hulls.  Additionally, trials were conducted in grapes to
support a tolerance for grapes.

Based on the properties of penoxsulam and results from residue studies
in other crops along with the proposed use pattern on tree nuts and
grapes, Dow AgroSciences expected that residues in almond hulls, nutmeat
and grapes would not be detected.  A proposal for was submitted to US
EPA that suggested almond and pecan trials be carried out at three
locations and grape trials would be carried out at four locations.  The
objective of these trials would be to confirm that penoxsulam residues
in almond hulls, nutmeat and grapes are not detected when penoxsulam is
applied according to the proposed use patterns.  

Grape – Magnitude of Residue Trials and Processing Study

The magnitude of residues of   DOCVARIABLE  AI1lc  \* MERGEFORMAT   in
grapes was determined following two applications of penoxsulam.  Four
trials were conducted at sites in New York, California and Washington
(NAFTA zones 1, 10 and 11, respectively).    DOCVARIABLE  AI1TC  \*
MERGEFORMAT    DOCVARIABLE  AI1TC  \* MERGEFORMAT  Penoxsulam  was
applied to the vineyard floor as the   DOCVARIABLE  FormNo1  \*
MERGEFORMAT  GF-1075  formulation (an   DOCVARIABLE  FormType1  \*
MERGEFORMAT  oil dispersion (OD) ) in each of two broadcast applications
with a 60 day PHI.  The target rates for the first and second
applications were penoxsulam at 40 g a.i./ha (0.0357  lb ai/A) and 20 g
a.i./ha (0.0178 lb ai/A), respectively.  Additionally, at one trial site
a plot was treated with penoxsulam at a 5X rate (200 g ai/ha + 100 g
ai/ha, or 0.1784 lb ai/A + 0.0892 lb ai/A) and grapes were collected
for processing to grape juice and raisins.  All spray mixtures included
crop oil concentrate at 1.25% (v/v).  

 

Penoxsulam was determined using liquid chromatography with positive-ion
electrospray tandem mass spectrometry (LC/MS/MS).  The limit of
detection (LOD) and limit of quantitation (LOQ) for penoxsulam in
grapes, juice and raisins were 0.003 µg/g and 0.01 µg/g, respectively.

Residue was not detected (ND, <0.003 µg/g) in any of the grape samples
from treated or untreated control plots.  Additionally, no residue was
detected in whole grapes collected in the field from the 5X rate
treatment or at the beginning of processing, and no residue was detected
in the grape juice or raisins produced from processing these grapes. 
Therefore, there is no concentration of residue from grapes to either
juice or raisins. 

Almond – Magnitude of Residue Trials

The magnitude of residues of   DOCVARIABLE  AI1lc  \* MERGEFORMAT   in
almond hulls and nutmeat was determined following two applications of
penoxsulam.  Three trials were conducted at sites in California (NAFTA
zone 10).   DOCVARIABLE  AI1TC  \* MERGEFORMAT     DOCVARIABLE  AI1TC 
\* MERGEFORMAT  Penoxsulam  was applied to the orchard floor as the  
DOCVARIABLE  FormNo1  \* MERGEFORMAT  GF-1075  formulation (an  
DOCVARIABLE  FormType1  \* MERGEFORMAT  oil dispersion (OD) ) in each of
two broadcast applications with a 60 day PHI.  The target rates for the
first and second applications were 50 g a.i./ha (0.0446 lb ai/A) and 20
g a.i./ha (0.0178 lb ai/A), respectively.  All spray mixtures included
crop oil concentrate at 1.25% (v/v).  

Penoxsulam was determined using liquid chromatography with positive-ion
electrospray tandem mass spectrometry (LC/MS/MS).  The limit of
detection (LOD) and limit of quantitation (LOQ) for penoxsulam in both
almond hulls and nutmeat were 0.003 µg/g and 0.01 µg/g, respectively. 
Residue was not detected (ND, <0.003 µg/g) in any of the almond hull or
nutmeat samples.

Pecan – Magnitude of Residue Studies

The magnitude of residues of   DOCVARIABLE  AI1lc  \* MERGEFORMAT   in  
DOCVARIABLE  Cr1lc  \* MERGEFORMAT   was determined following two
applications of penoxsulam.  Three trials were conducted at sites in
Georgia, Louisiana and Texas (NAFTA zones 2, 4 and 8).    DOCVARIABLE 
AI1TC  \* MERGEFORMAT     DOCVARIABLE  AI1TC  \* MERGEFORMAT  Penoxsulam
 was applied to the orchard floor as the   DOCVARIABLE  FormNo1  \*
MERGEFORMAT  GF-1075  formulation (an   DOCVARIABLE  FormType1  \*
MERGEFORMAT  oil dispersion (OD) ) in each of two broadcast applications
with a 60 day PHI.  The target rates for the first and second treatment
applications were 50 g a.i./ha (0.0446 lb ai/A) and 20 g a.i./ha (0.0178
lb ai/A), respectively.   All spray mixtures included crop oil
concentrate at 1.25% (v/v).  

Penoxsulam was determined using liquid chromatography with positive-ion
electrospray tandem mass spectrometry (LC/MS/MS).  The limit of
detection (LOD) and limit of quantitation (LOQ) for penoxsulam in pecan
nutmeat were 0.003 µg/g and 0.01 µg/g, respectively.  Residue was not
detected (ND, <0.003 µg/g) in any of the pecan nutmeat samples from
control or treated plots.

B. Toxicological Profile

	1. Acute toxicity.  [The acute toxicity of penoxsulam is considered
low.  The acute oral and dermal LD50s were greater than 5000 mg/kg,
while the acute inhalation LC50 was greater than the highest attainable
aerosol concentration (3.50 mg/L).  Only very slight, transient dermal
irritation was seen, and mild eye irritation was noted. Penoxsulam was
negative for skin sensitization in a Magnussen and Kligman maximization
test involving intradermal injection of penoxsulam with an adjuvant.]

	2. Genotoxicity. [Penoxsulam was negative for genotoxicity when tested
in in vitro and in vivo systems.]

	3. Reproductive and developmental toxicity. [Penoxsulam did not have
any effect on reproductive parameters at dose levels that induced
treatment-related effects in parental rats.  At the highest dosage
tested (300 mg/kg/day), body weights and weight gains in both males and
females were depressed, liver and/or kidney weights were increased, and
histologic changes were noted in the liver (males) and kidneys
(females).  At 100 mg/kg/day, increased liver weights were recorded in
males, with no histologic correlate, and histologic changes noted in the
kidneys of females.  Transient decreases in pup body weights were seen
at the highest dosage tested, but dietary concentrations were targeted
for adults and consumption of treated diets by the pups resulted in dose
levels to the pups approximately 3-fold higher than in adults.  A
teratogenic potential was not demonstrated for penoxsulam in either rats
or rabbits.]

	4. Subchronic toxicity. [Dietary exposure to penoxsulam identified the
liver and/or urinary tract (kidneys and bladder) as target organs in
rats, mice and dogs following 4-week and 13-week administration. 
Effects on the liver were reflected in increased liver weights and
hepatocellular hypertrophy, but these effects were not associated with
increases in mixed function oxidase (MFO) enzyme activity.  Effects
noted in the kidneys included crystal deposition, most likely from
precipitation of penoxsulam from the urine, with resultant irritation,
inflammation and hyperplasia of renal pelvic transitional epithelium. 
Other than the crystal deposition in the kidneys, all effects following
subchronic exposure to rats appeared to be reversible.  Very high doses
were associated with significant decreases in body weight and weight
gain, and feed consumption.]

	5. Chronic toxicity. [Chronic exposure in the dog indicated that the
renal effects were not exacerbated with long-term exposure.  Following
long-term exposure in rats, the kidneys and urinary bladder were the
primary target organs.  Histologic changes seen at the end of 2-years of
exposure consisted of inflammation and hyperplasia of the renal pelvic
transitional epithelium, crystal deposition in the kidneys and urinary
bladder, and hyperplasia of the mucosa of the urinary bladder.  In the
mouse, the liver was the primary target organ, and histologic changes
consisted of hepatocellular hypertrophy.  There were no
treatment-related increases in tumors in either rats or mice.  The
incidence of mononuclear cell leukemia (Fischer rat leukemia) was
increased in all groups of treated male rats compared to the concurrent
controls.  However, the incidences in the treated groups were identical
across a 50-fold increase in dosage, and well within the range of
control values reported in the literature.

Using the Guidelines for Carcinogen Risk Assessment published September
24, 1986 (51 FR 33992), it is proposed that penoxsulam be classified as
Group E for carcinogenicity (no evidence of carcinogenicity) based on
the results of carcinogenicity studies in two species.  Dow AgroSciences
believes there was no evidence of carcinogenicity in an 18-month mouse
feeding study and a 24-month rat feeding study at all dosages tested.]

	6. Animal metabolism. [Orally administered penoxsulam is rapidly
absorbed, excreted and extensively metabolized in both male and female
rats, thus, indicating that penoxsulam is not expected to accumulate in
biological systems.  The majority of the residue was associated with the
parent, penoxsulam.  Several metabolites were also observed but the vast
majority were <1% of the administered dose.  The major route of
metabolism involves O-demethylation, producing the OH- Penoxsulam
metabolite followed by conjugation.]

	7. Metabolite toxicology. [A metabolism study with penoxsulam in rice
revealed the presence of the parent, a desmethylation metabolite (5-OH-
Penoxsulam), and two other polar metabolites, which may represent
conjugates of the desmethylated metabolite.  The 5-OH-Penoxsulam
metabolite and its glucuronide and glutathione conjugates have also been
identified in the plasma and liver of rats, therefore, plant metabolites
are considered of little toxicological concern.]

	8. Endocrine disruption. [Penoxsulam did not have any effects on
endocrine organs or tissues in mice, rats or dogs in any of the studies
conducted.  There were no indications of effects on fetal development in
either rats or rabbits, or on reproductive performance in rats.  Based
on the lack of any effects on the endocrine system, penoxsulam is not
considered an endocrine disrupter.]

C. Aggregate Exposure

	1. Dietary exposure. [Tier 1 dietary risk assessments were performed
using DEEM-FCID™ software (version 2.14) to determine consumption of
tree nuts and grapes containing penoxsulam residues and to determine
dietary exposure resulting from consumption of tree nuts and grapes
treated with penoxsulam.]

	i. Food. [Penoxsulam is registered for use as an herbicide on rice. 
Therefore, consumption of rice that has been treated with penoxsulam
could result in dietary exposures.  On September 24, 2004, EPA finalized
tolerances for penoxsulam in rice, grain (0.02 ppm) and rice, straw (0.5
ppm) (69 FR 57188-57197).  In establishing the tolerances for rice,
grain and rice, straw, EPA concluded that chronic dietary exposures were
<1% of the cPAD, but exposure estimates were not provided.  On July 25,
2007, EPA finalized tolerances for penoxsulam in fish, and shellfish. 
For the purposes of this aggregate assessment, it is necessary to
estimate dietary exposures of penoxsulam resulting from tolerance level
residues on rice, fish and shellfish in addition to the proposed new
uses.  Secondary residues in meat, milk and poultry were not included
because the transferability of penoxsulam to edible tissues is quite low
and tolerances are not required.  A chronic dietary exposure and risk
assessment for tolerance-level residues in existing and proposed uses
was performed using the DEEM-FCID™ software (version 2.14).  An acute
dietary assessment was not performed because no toxicity endpoint has
been identified to evaluate acute dietary exposures to penoxsulam (EPA,
2004).  To produce a conservative Tier 1 dietary risk assessment,
tolerance-level residues were assumed for all commodities, and 100
percent crop treated was assumed for all commodities.

Dietary penoxsulam exposures range from 0.000009 mg/kg/d for Females
13-19 (not pregnant or nursing) to 0.000052 mg/kg/d for children 1-2
years.  These estimated penoxsulam exposures are very low, accounting
for less than 0.1% of the cRfD (0.147 mg/kg/d) for all subpopulations.]

	ii. Drinking water. [Calculation of potential acute aggregate dietary
exposure from food and drinking water was not necessary.  Risk
assessment for short-term and chronic exposure to penoxsulam indicates
that drinking water is not a significant exposure pathway.  

Based on the FIRST, SCI-GROW, and GENEEC2 models, the most conservative
environmental concentrations (EECs) of penoxsulam for chronic exposures
are estimated to be 0.4 ppb for surface water and 0.046 ppb for ground
water.  For the purpose of these assessments, 0.4 ppb was used for the
chronic exposure estimate for water, and this value was incorporated as
a single point estimate for both “water, direct, all sources” and
“water, indirect, all sources” within DEEM-FCID( food categories
exposure modeling.  Based on the conservative assumptions used and using
a cPAD of 0.147 mg/kg/day, the chronic dietary exposure to penoxsulam
from all registered and proposed uses and drinking water, to all
population subgroups is approximately <0.1% of the cPAD.  Children 1-2
years old have been identified as the most highly exposed population
subgroup yet utilizing only <0.1% of the cPAD.

It may be reasonably concluded that overall aggregate penoxsulam
exposures from the diet and drinking water uses will be associated with
a reasonable certainty of no harm.]

	2. Non-dietary exposure. [Short-term exposures and MOEs for handlers
making applications of penoxsulam for tree nut and grape vegetation
control are estimated to range from 340,000 to >2,000,000 , depending on
the work function performed (M/L open/closed system; or applying liquids
open/closed cab).  These MOEs, which are considerably in excess of the
target of 100, indicate that penoxsulam may be applied according to
label instructions with a reasonable certainty of no harm for
mixer/loader/applicators.

Adult residential exposure MOEs during and post application were
>1,000,000 and >60,000 respectively.  Residential exposure MOE for
children (dermal, soil ingestion, OtM, HtM) was calculated to be 13,000.
 An aggregate risk assessment was conducted for chronic exposure from
drinking water and dietary intakes and the short-term exposure during
residential application for penoxsulam, as pertains to uses on turf
according to the EPA SOP for aggregate assessment guidance document
(EPA, 1999).  The short-term aggregate total MOEs range from 12,000 for
toddlers to 370,000 for adults.  The long-term aggregate total MOEs
range from 12,000 for toddlers to 56,000 for adults.  As these values
illustrate, conservatively estimated total aggregate MOEs for all
dietary, oral (incidental non-dietary), drinking water and dermal
exposures are greater than 100.  Thus, anticipated aggregate exposures
estimated with conservative assumptions regarding use patterns of the
full range of registered and proposed penoxsulam products are not of
concern.]

D. Cumulative Effects

	[Currently, no methodologies are available to resolve the complex
scientific issues concerning common mechanism of toxicity and cumulative
exposure and risk. The U.S. EPA has begun a pilot process to study this
issue further through the examination of particular classes of
pesticides.  Thus, Dow AgroSciences believes it is appropriate to
consider only the potential risks of penoxsulam in its exposure
assessment.]

E. Safety Determination

	1. U.S. population. [Using the conservative exposure assumptions
described above, and based on the completeness and reliability of the
toxicity data, the aggregate exposure to penoxsulam, as determined under
the guidance of the FQPA, will utilize less than 0.1% of the RfD from
the dietary exposure for all subgroups of the U.S. population. 
Generally and under the FQPA, the U.S. EPA has no concern for exposures
below 100% of the RfD because the RfD represents the level at or below
which daily dietary exposure over a lifetime will not pose appreciable
risks to human health.  Additionally, the chronic dietary exposure to
penoxsulam from all registered and proposed uses and drinking water, to
all population subgroups is approximately <0.1% of the cPAD.  Therefore,
there is a reasonable certainty that no harm will result to the general
U.S. population from aggregate exposure to penoxsulam residues from the
proposed use.]

	2. Infants and children. [In assessing the potential for additional
sensitivity of infants and children to residues of penoxsulam, data from
developmental toxicity studies in rats and rabbits and a
multi-generation reproduction study in the rat are considered.  The
developmental toxicity studies are designed to evaluate adverse effects
on the developing organism resulting from pesticide exposure during
prenatal development.  Reproduction studies provide information relating
to effects from exposure of both parents to the pesticide on the
reproductive capability and potential systemic toxicity of mating
animals and on various parameters associated with the well being of
offspring.

FFDCA section 408 provides that the U.S. EPA may apply an additional
safety factor for infants and children in the case of threshold effects
to account for pre- and post-natal toxicity and the completeness of the
database.  Based on the current toxicological data requirements, the
database for penoxsulam relative to pre- and post-natal effects for
children is complete.  Overall, penoxsulam had no effect on reproduction
or embryo-fetal development at any dosage tested.  No quantitative or
qualitative susceptibility was seen following pre- and post-natal
exposures.  In a rabbit developmental toxicity study, effects on
in-utero survival were observed only at a dose level where clear
maternal toxicity was seen.  In a 2-generation reproductive toxicity
study in rats, no effects on reproductive performance were observed and
effects on neonatal growth were seen only at a dose level where parental
toxicity was seen.  In addition, the NOAEL in the chronic dog study
(14.7 mg/kg/day), used to calculate the chronic RfD (0.147 mg/kg/day),
is already lower than the NOAEL from the rabbit developmental study (25
mg/kg/day).  Therefore, an additional FQPA uncertainty factor is not
needed and the RfD at 0.147 mg/kg/day is appropriate for assessing risk
to infants and children.  Using the conservative exposure assumptions
previously described, the percent RfD utilized by the potential exposure
to residues of penoxsulam is less than 0.1% for children 1-2 years, the
population subgroup predicted to
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F. International Tolerances

	[A review of Maximum Residue Limits (MRLs) established globally
indicates that no corresponding MRLs have been established for
penoxsulam in or on grapes, pistachios or tree nuts.  However,
registration has been requested on grapes in France where the proposed
MRL is 0.01 mg/kg.  Residues in the grapes in the trials in France were
not detected and the proposed MRL is based on the LOQ of the analytical
method.]

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