Docket ID #:  EPA-HQ-OPP-2010-1017

COMPANY NOTICE OF FILING FOR RIMSULFURON TOLERANCE PETITION

EPA Registration Division contact: Sidney Jackson,<PHONE_NUMBER>

I.E.I. du Pont de Nemours and Company (DuPont), and

Interregional Research Project Number 4 (IR-4)

PP No. 0E7809

EPA has received a pesticide petition (PP No. 0E7809) from the IR-4,
Rutgers, The State University of New Jersey, 500 College Road East,
Suite 201W. Princeton, NJ 08540, proposing pursuant to section 408 (d)
of the Federal Food, Drug, and Cosmetic Act, 21 U.S.C. 346a (d), to
amend 40 CFR Part 180.478 by establishing a tolerance for residues of
the herbicide rimsulfuron N-((4,6-dimethoxypyrimidin-2-yl)
aminocarbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide in or on the raw
agricultural commodities caneberry subgroup 13-07A at 0.01 parts per
million (ppm) and bushberry subgroup 13-07B at 0.01 ppm.  This summary
was prepared by the registrant, DuPont. 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
support granting the petition. Additional data may be needed before EPA
rules on the petition.

A. Residue Chemistry

1. Plant and animal metabolism.

With the initial establishment of rimsulfuron tolerances in field corn
and potato, the EPA determined that the nature of plant residues was
adequately understood for the purposes establishing those tolerances. A
metabolism study in tomatoes was conducted to support establishment of
tolerances for Rimsulfuron in tomato. Based on these studies, the Agency
previously concluded that only rimsulfuron needs to be regulated and
assessed for dietary assessment. Further, the nature of the residue in
corn and potatoes is adequately understood. The nature of the residue in
animals is adequately understood based on acceptable ruminant and
poultry metabolism studies. The pathways of rimsulfuron metabolism in
ruminants and poultry are consistent with those demonstrated in plants.

2. Analytical method.

Adequate analytical methodology, high-pressure liquid chromatography
(HPLC) with electrospray ionization tandem mass spectrometry (ESI-MS/MS)
detection, is available for enforcement purposes.

3. Magnitude of residues.

a. Magnitude of the residue in plants:

i. Caneberry

The results from six trials show that the maximum residue in caneberry
is <0.01 ppm following a single application of approximately 0.0625
pound active ingredient per acre (lb ai/A) rimsulfuron when the
application is made 21-24 days prior to harvest.

ii. Bushberry

The results from eight trials show that the maximum residue in blueberry
is <0.01 ppm following a single application of approximately 0.0625 lb
ai/A rimsulfuron when the application is made 19-23 days prior to
harvest.

b. Magnitude of the residue in animals:

EPA determined, upon granting field corn and potato tolerances, that
there is no reasonable expectation of residues occurring in meat, milk,
poultry, or eggs from these tolerances. Of the commodities for which
tolerances are being proposed, only wet apple pomace, citrus dried pulp,
and almond hulls are considered possible animal feed items. However, the
worst-case animal dietary burden is comprised of only field corn and/or
potato commodities. Therefore, there remains a reasonable expectation
that no residues of rimsulfuron will occur in meat, milk, poultry, or
eggs from the current, and proposed, rimsulfuron tolerances.

B. Toxicological Profile

1. Acute toxicity.

Technical rimsulfuron has been placed in acute toxicology category III
based on overall results from several studies. This compound was placed
in toxicology category III for acute dermal toxicity (lethal dose (LD)50
> 2,000 milligram per kilogram (mg/kg); rabbits) and eye irritation
(effects reversible within 72 hours; rabbits). Acute oral toxicity (LD50
> 5,000 mg/kg; rats), acute inhalation toxicity (lethal concentration
(LC)50 > 5.4 mg/liter (L), rats) and skin irritation (no observed
irritation; rabbits) results were assigned toxicology category IV.
Technical rimsulfuron is not a dermal sensitizer.

2. Genotoxicty.

Technical rimsulfuron was negative for genotoxicity in a battery of in
vitro and in vivo tests. These tests included the following:
mutagenicity in bacterial (Ames test) and mammalian (CHO/HGPRT assay)
cells; in vitro cytogenetics (chromosomal aberration in human
lymphocytes); in vivo cytogenetics (bone marrow micronucleus assay in
mice); and unscheduled DNA synthesis in rat primary hepatocytes.

3. Reproductive and developmental toxicity.

A two-generation reproduction study was conducted in rats with dietary
technical rimsulfuron concentrations of 0, 50, 3,000 or 15,000 ppm. The
study was negative for reproductive toxicity and there was no indication
that offspring were more susceptible to rimsulfuron administration than
parents. The NOAEL was 3,000 ppm (or 165 to 264 mg/kg/day for P1 and F1
males and females and their offspring). This was based on the following
effects at 15,000 ppm (830 to 1,316 mg/kg/day): lower food consumption
and/or food efficiency in P1 males and females and F1 females; decreased
mean body weights and/or body weight gain by P1 and F1 males and
females; lower mean body weights and increased incidence of small body
size for F2 pups during lactation.

A developmental study was conducted in rats administered technical
rimsulfuron by gavage at 0, 200, 700, 2,000 or 6,000 mg/kg/day. There
were no systemic or developmental effects observed up to and including
the highest dose tested. The NOAEL was therefore > 6,000 mg/kg/day.

A developmental study was conducted in rabbits administered technical
rimsulfuron by gavage at 0, 25, 170, 500 or 1,500 mg/kg/day. The NOAELs
for maternal and offspring toxicity were 170 and 500 mg/kg/day,
respectively. The maternal NOAEL was based on reduced body weight and
mortality at higher doses. These maternal effects precluded any
evaluation of adverse effects in fetuses at 1,500 mg/kg/day; however,
there were no systemic or developmental effects observed among fetuses
at 500 mg/kg/day and below.

4. Subchronic toxicity.

A 90-day study in mice was conducted at dietary concentrations of 0, 50,
375, 1,500 or 7,500 ppm. The NOAELs were 375 ppm (56.0 mg/kg/day) for
male mice and 7,500 ppm (1,575 mg/kg/day) for female mice. The NOAEL for
males was based on slight reductions in mean body weight gain and food
efficiency at 1,500 ppm (228 mg/kg/day).

Technical rimsulfuron was administered in the diets of rats at 0, 50,
1,500, 7,500 or 20,000 ppm for 90 days. The NOAEL was 1,500 ppm (102 and
120 mg/kg/day for males and females, respectively) based on reduced mean
body weights and body weight gains and increased relative liver weights
at 7,500 ppm (495 and 615 mg/kg/day for males and females,
respectively).

Dogs were administered technical rimsulfuron in their diets at 0, 250,
5,000 or 20,000 ppm for 90 days. The NOAEL was 250 ppm (9.63 and 10.6
mg/kg/day for males and females, respectively). This was based on slight
increases in liver and/or kidney weights, increased urine volume and
decreased urine osmolarity at 5,000 ppm (193 and 189 mg/kg/day for males
and females, respectively).

5. Chronic toxicity.

An 18-month mouse study was conducted with dietary concentrations of 0,
25, 250, 2,500 or 7,500 ppm technical rimsulfuron. This product was not
oncogenic in mice. The systemic NOAEL was 2,500 ppm (351 and 488
mg/kg/day for males and females, respectively) based on decreased mean
body weights in both sexes and increased incidence of spontaneous,
age-related artery and tunica degeneration in the testes for this mouse
strain at the highest dose tested, 7,500 ppm (1,127 and 1,505 mg/kg/day
for males and females, respectively). The latter was observed in the
absence of any effect on spermatogenesis. An increased incidence of
dilation and cysts in the glandular stomach of males was also observed
at 7,500 ppm.

A 2-year chronic toxicity/oncogenicity study was conducted in rats fed
diets that contained 0, 25, 300, 3,000 or 10,000 ppm technical
rimsulfuron. This product was not oncogenic in rats. The systemic NOAELs
were 300 ppm (11.8 mg/kg/day) for males and 3,000 ppm (163 mg/kg/day)
for females. The NOAELs were defined by decreased body weight gain and
increased relative liver weights at 3,000 ppm (121 mg/kg/day) and 10,000
ppm (569 mg/kg/day) for males and females, respectively.

Technical rimsulfuron was administered for one year to dogs at dietary
concentrations of 0, 50, 2,500 or 10,000 ppm. The NOAELs were 50 ppm
(1.6 mg/kg/day) for males and 2,500 ppm (86.5 mg/kg/day) for females.
The NOAEL for males was based on the following effects, which the Agency
has previously determined were of questionable biological significance,
observed at 2,500 ppm (81.8 mg/kg/day): increased absolute liver and
kidney weights; and increased incidence of seminiferous tubule
degeneration and increased numbers of spermatid giant cells present in
the epididymides. The NOAEL for females was based on the following
effects observed at 10,000 ppm (358.5 mg/kg/day): decreased body weight
and body weight gain; increased serum cholesterol levels and alkaline
phosphatase activity, increased absolute liver weight and increased
relative liver and kidney weights.

6. Animal metabolism.

The metabolism of rimsulfuron in animals (rat, goat and hen) is
adequately understood and is similar among the species evaluated.
Rimsulfuron was rapidly eliminated via urinary and fecal excretion in
the rat. Approximately 60 to 70% of the administered dose to rats was
excreted within 24 hours. There were no volatile metabolites detected
and unmetabolised rimsulfuron was the major component in the urine (42 -
55%) and feces (5 - 16%). The major metabolic pathway in rats involved a
contraction of the sulfonylurea bridge followed by dealkylation,
hydroxylation and/or conjugation reactions. Cleavage of the sulfonylurea
bridge was observed; however, it was considered to be a minor pathway.
Elimination of administered rimsulfuron was similarly rapid for the goat
and hen. Tissue residue levels were generally less than 0.3% of the
administered dose for the rat, goat and hen. There was no evidence of
accumulation of rimsulfuron or its metabolites in tissues of any of the
species or in milk and eggs.

7. Metabolite toxicology.

Common metabolic pathways for rimsulfuron were demonstrated in the rat,
goat and hen as well as plants (corn, tomatoes and potatoes). When
evaluated for acute toxicity and mutagenicity, two of the major
metabolites, i.e., one resulting from contraction of the sulfonylurea
bridge and one from the cleavage of this bridge, were found to be of low
toxicity and were negative in the Ames test. The existing metabolism
studies indicate that the metabolites formed are unlikely to accumulate
in humans or in animals that may be exposed to these residues in the
diet. The fact that no quantifiable residues were found in treated crops
further indicates that exposures to and accumulation of metabolites are
unlikely. Because of the above, toxicology studies on metabolites were
not required.

8. Endocrine disruption.

No special studies investigating potential estrogenic or other endocrine
effects of rimsulfuron have been conducted.  However, the standard
battery of required toxicology studies has been completed. These include
an evaluation of the potential effects on reproduction and development,
and an evaluation of the pathology of the endocrine organs following
repeated or long-term exposure to doses that far exceed likely human
exposures.  Based on these studies there is no evidence to suggest that
rimsulfuron has an adverse effect on the endocrine system.

C. Aggregate Exposure

1. Dietary exposure.

When tolerances were established on field corn and potatoes, EPA
determined that the residue of concern was rimsulfuron. Therefore, for
the commodities for which new tolerances are being proposed, the residue
of concern continues to be rimsulfuron.

No acute dietary risk assessment was needed since there is no acute tox
endpoint.

The chronic risk assessments (food only and food + water) for
rimsulfuron were conducted using DEEM-FCIDTM software, version 2.16
(Exponent, Inc.).  A chronic reference dose of 0.818 mg/kg/day, from a
systemic NOAEL of 81.8 mg/kg/day from a one-year beagle dog tox study,
was used.  Tolerance values were used for residue inputs, no processing
factors were employed, and 100% crop treated was assumed.  All
commodities for a given crop were included, ie, orange juice (citrus),
wine, almond oil, and field corn flour.

a. Food.

i. Acute

For the general U.S. population, acute dietary exposure assessments were
not considered relevant for rimsulfuron for the following reasons:
rimsulfuron presents very low acute toxicity based on animal testing;
and no detectable residues have been demonstrated in edible portions of
treated crops.

ii. Chronic

There is no population in the chronic risk assessment for rimsulfuron,
either dietary (food only) or aggregate (food and water), with an
exposure greater than 0.1% of the chronic reference dose.

b. Drinking water.

Chronic drinking water exposure analyses were calculated for rimsulfuron
based on the First Index Reservoir Screening Tool (FIRST) and Screening
Concentration in Ground Water (SCI-GROW) models.  Results indicate that
a reasonable certainty exist that rimsulfuron residues in drinking water
will not contribute significantly to the aggregate human risk.

The predicted chronic concentration for rimsulfuron maximum surface
water value was 0.74 parts per billion (ppb), and a maximum ground water
value was 0.0522 ppb.  When the surface water concentration was included
in the chronic dietary risk assessment, no population including the
general U.S. population and all subpopulations had an exposure greater
0.1% of the chronic reference dose (cRfD), indicating a significant
margin of safety.

No acute dietary endpoint was identified. Therefore, an acute drinking
water risk assessment is not considered necessary. One can conclude with
reasonable certainty that residues of Rimsulfuron in drinking water do
not contribute significantly to the aggregate acute human health risk.

2. Non-dietary exposure.

Rimsulfuron is not registered for any use that could result in
non-occupational, non-dietary exposure to the general population.

D. Cumulative Effects

Rimsulfuron belongs to the sulfonylurea class of crop protection
chemicals. Other structurally similar compounds in this class are
registered herbicides. However, the herbicidal activity of sulfonylureas
is due to the inhibition of acetolactate synthase (ALS), an enzyme found
only in plants. This enzyme is part of the biosynthesis pathway leading
to the formation of branched chain amino acids. Animals lack ALS and
this biosynthetic pathway. This lack of ALS contributes to the
relatively low toxicity of sulfonylurea herbicides in animals. There is
no reliable information that would indicate or suggest that rimsulfuron
has any toxic effects on mammals that would be cumulative with those of
any other chemical.

E. Safety Determination

1. U.S. population.

Based on the completeness and reliability of the toxicology database and
using the conservative assumptions presented earlier, EPA has
established a chronic RfD of 0.818 mg/kg/day. This RfD is based on the
systemic NOAEL of 81.8 mg/kg/day for males in a 1-year toxicity study in
beagle dogs. It has been concluded that the aggregate exposure for
existing crops plus the tolerances being proposed would utilize less
than 0.1% of the RfD. Generally, exposures below 100% of the RfD are of
no concern because it represents the level at or below which daily
aggregate dietary exposure over a lifetime will not pose appreciable
risk to human health. Thus, there is reasonable certainty that no harm
will result from aggregate exposures to rimsulfuron residues.

2. Infants and children.

In assessing the potential for additional sensitivity of infants and
children to residues of rimsulfuron, data from the previously discussed
developmental and multigeneration reproductive toxicity studies were
considered.

Developmental studies are designed to evaluate adverse effects on the
developing organism resulting from pesticide exposure during pre-natal
development. Reproduction studies provide information relating to
reproductive and other effects on adults and offspring from pre-natal
and post-natal exposures to the pesticide. The studies with rimsulfuron
demonstrated no evidence of developmental toxicity at exposures below
those causing maternal toxicity. This indicates that developing animals
are not more sensitive to the effects of rimsulfuron administration than
adults.

FFDCA section 408 provides that EPA may apply an additional uncertainty
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 current toxicological data requirements, the database
for rimsulfuron relative to pre- and post-natal effects for children is
complete. In addition, the NOAEL upon which the RfD is based is much
lower than the NOAELs defined in the reproduction and developmental
toxicology studies. Conservative assumptions utilized to estimate
aggregate dietary exposures of infants and children to rimsulfuron
demonstrated that only 0.1% of the RfD would be utilized for the highest
exposed group, Children 1-2 years old. Based on these exposure estimates
and the fact that the current database demonstrates that the developing
offspring or young animals are not uniquely susceptible to rimsulfuron
administration, the extra 10-fold uncertainty factor is not warranted
for these groups. Therefore, it may be concluded that there is
reasonable certainty that no harm will result to infants and children
from aggregate exposures to rimsulfuron.

F. International Tolerances

A number of international tolerances (or Maximum Residue Levels (MRLs))
have been established for rimsulfuron including the following:

Countries	Crop	Tolerance/MRL

Austria, Italy	Corn	0.1 ppm

Austria, Italy, Canada	Potatoes	0.1 ppm

Belgium, Denmark, Germany, Spain	Potatoes	0.05 ppm

Germany, Spain, Portugal, Canada	Tomatoes	0.05 ppm

Pesticide Petition for Tolerances		AGRICULTURAL COMMODITIES

for Rimsulfuron	Caneberry Subgroup 13-07A, Bushberry Subgroup 13-07B


[Federal Register Volume 82, Number 136 (Tuesday, July 18, 2017)]
[Notices]
[Page 32810]
[FR Doc No: 2017-15058]

-----------------------------------------------------------------------

DEPARTMENT OF ENERGY

Federal Energy Regulatory Commission

Combined Notice of Filings

    Take notice that the Commission has received the following Natural
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    Dated: July 11, 2017.
Nathaniel J. Davis, Sr.,
Deputy Secretary.
[FR Doc. 2017-15058 Filed 7-17-17; 8:45 am]
 BILLING CODE 6717-01-P


                 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY                          WASHINGTON, D.C. 20460

                                                 	OFFICE OF CHEMICAL SAFETY AND                                                                                POLLUTION PREVENTION

MEMORANDUM

	Date:	26 September 2012

	SUBJECT:	Clothianidin  -  New Uses on Strawberry, Pistachio, Citrus, and Tea.  Evaluation of Residue Chemistry Data.

PC Code:  044309 DP Barcode:  D397689 Decision No.: 455249 Registration No.:  59639-150, 59639-152 Petition Nos.:  1E7923 Regulatory Action:  Section 3 Risk Assessment Type:  N/A Case No.:  7620 TXR No.:  N/A CAS No.:  210880-92-5 MRID No.:  48600001-48600005 40 CFR:180.586

	FROM:	Michael A. Doherty, Ph.D., Chemist 		Risk Assessment Branch II 		Health Effects Division (7509P)

	THROUGH:	Dennis McNeilly, Chemist 		Risk Assessment Branch II 		Health Effects Division (7509P)

	TO:	Marianne Lewis/Venus Eagle, RM 01 	Insecticide-Rodenticide Branch  	Registration Division (7505P)

	Barbara Madden 	Risk Integration, Minor Use, and Emergency Response Branch 		Registration Division (7505P)

Background

Interregional Research Project No. 4 (IR-4) has petitioned the Agency to approve new uses of the insecticide clothianidin on strawberry, pistachio, and the citrus crop group (Crop Group 10-10), and to establish tolerances in support of those uses.  Additionally, IR-4 has requested the establishment of a tolerance for residues of clothianidin in/on tea without a domestic registration (i.e., an import tolerance).  In support of the petition, IR-4 has submitted field trial data depicting residues of clothianidin in/on strawberry, lemon, grapefruit, orange, and tea, and an orange-processing study.  IR-4 has requested that the tolerance for pistachio be translated from the existing tolerance for residues in/on tree nuts.

Regulatory Recommendations

There are no residue chemistry considerations that would preclude granting the requested registrations and establishing permanent tolerances at the following levels: Pistachio	0.01 ppm Strawberry	1.50 ppm Fruit, citrus, group 10-10	0.60 ppm Tea, dried	70 ppm

These recommended tolerance levels differ from the petitioned-for tolerance levels for strawberry, citrus, and tea, and HED has determined that a separate tolerance is not necessary for citrus, dried pulp.

There are no Canadian or Codex MRLs for clothianidin that are relevant to the recommended tolerances.  Codex MRLs (see Attachment 1) are in place for tea, strawberry, citrus, and fruiting vegetables; however, the MRLs are based on clothianidin derived from treatment with thiamethoxam rather than treatment with clothianidin.  Therefore, it is not appropriate to harmonize U.S. tolerances with the Codex MRLs.

Prior to registration, the petitioner should submit a revised Section F which requests tolerances at the recommended levels and with the commodity definitions listed above.  Furthermore, the tolerance expression in the Section F should be revised to reflect the current tolerance definition in 40 CFR 180.586.

Label Revision Recommendations

We note that IR-4 has included some restrictions against use of adjuvants and aerial application.  HED has recently recommended that aerial application be allowed for Brassica vegetables, fruiting vegetables, leafy vegetables, peach, pomegranate, and tree nuts, and that restrictions regarding use of adjuvants be removed.  If these requested uses are approved, RD should ensure that the product label reflects all of the recent revisions/recommendations that were made outside of this new-use action.  This includes updating the rotational crop restrictions to include strawberry as a crop suitable for immediate plant back.

In addition, HED recommends that the label be revised for all crops to state that the maximum amount of active ingredient applied per season is 0.2 lb a.i./A regardless of the formulation and type of application being made.

Finally, HED notes that the maximum seasonal foliar use rate for V-10170 2.13 SC on strawberry (0.1 lb a.i./A) differs from the maximum use rate for the Arena product (0.2 lb a.i./A).  HED recommends that RD ensure that these differences are intended by the petitioner.  The available residue data support a maximum seasonal application rate of 0.2 lb a.i./A to strawberry.

Submitted Material and Evaluations

No data were submitted to support the tolerance for residues in/on pistachio.  The existing tolerance for residues of clothianidin in/on tree nuts is suitable for translation to pistachio.

IR-4 has submitted an acceptable proposed label and acceptable guideline studies depicting residues of clothianidin in/on strawberry and the representative crops of the citrus crop group (grapefruit, lemon, and orange) as well as an acceptable guideline study showing the behavior of residues upon processing of oranges into processed commodities.  An acceptable number of trials were conducted and demonstrate adequate geographical representation.  The residue data are supported by adequate method validation and storage stability information (summarized below).

For tea, IR-4 has submitted a compilation of reports conducted by Sumitomo Chemical Co., Ltd. and Takeda Pharmaceutical Co., Ltd. as well as data summary report from the Taiwanese Council of Agriculture.  These data are also supported by adequate method validation and storage stability information.  Details regarding the use pattern for tea were not provided.  Entries in the table are derived from information about the use patterns used in the field trials.

Summary of Proposed Use Patterns for Clothianidin on Pistachio, Strawberry, Citrus, and Tea. Crop Formulation Application Type Number of Applics. (min. RTI) Maximum Application Rate, lb a.i./A  PHI, Days Comments

per Applic. per Season

Pistachio V-10170 2.13 SC Foliar (ground or air) 2  (10-14) 0.1 0.2 21 -- Strawberry Arena 50 WDG Foliar (ground or air) 2  (7) 0.2 0.2 1 --

Soil (pre-or at-plant incorporated, furrow, transplant drench, chemigation into root zone) 1 0.2 0.2 21 --

V-10170 2.13 SC Foliar (ground or air) NS 0.1 0.1 1 --

Soil (pre-or at-plant incorporated, furrow, transplant drench, chemigation into root zone) 1 0.2 0.2 21 -- Citrus V-10170 2.13 SC Foliar (ground or air) 2 [implied] (14) 0.1 0.2 1 --

Basal Bark Spray NS 0.2 0.2 1 --

Soil (drench at base of tree, chemigation into root zone, soil surface band) 2 [implied] (NS) 0.2 0.2 1 -- Tea NS Foliar 1 1.8 1.8 7 Use patterns are implied from the field trial application parameters NS = Not Specified

Summary of Analytical Methods and Storage.  Crop Method ID Description LOQ, ppm                                Storage Stability

Sample Duration and Conditions  Demonstrated Stability Strawberry Residue Analytical Method 00552 Extraction with ACN:H2O (2:1, v/v), Cleanup with partitioning on a ChemElut column, Separation/Quantification via HPLC-MS/MS 0.014 (calc.) 0.02 (Lowest Limit of Method Validation, LLMV)                              <=515 days at -20°C                                    482 days Citrus (including processed commodities) RM-39C-1 Extraction with acidified water (0.1% formic acid), Cleanup on Celite, Separation/Quantification via HPLC-MS/MS 0.01 (LLMV) <=338 days at -15 to -5°C 374 days (lemon) Tea Not Specified Extraction with ACN: 0.1 M HCl, Cleanup on multiple solid phase columns, Separation/Quantification via HPLC/UV <=1.6 (LLMV) <=0.04 (LOD) <=306 days at -20°C 306 days

Summary of Clothianidin Residue Data. Commodity                           Application Rate, lb a.i./A                                    PHI, days                                        n                                Clothianidin, ppm                                                                                Min.                                      Max.                                      LAFT                                      HAFT                                     Median                                      Mean                                    Std. Dev. Strawberry                                       0.2                                        1 10 0.096 1.170 0.103 1.120 0.258 0.327 0.301 Grapefruit                                       0.2                                        1 5 0.022 0.346 0.027 0.281 0.072 0.113 0.103 Lemon                                       0.2                                        1 6 0.022 0.201 0.034 0.176 0.102 0.107 0.055 Orange                                       0.2                                        1 13 0.005 0.269 0.008 0.219 0.057 0.083 0.066 Tea                                   0.9  -  1.8                                       3-7 12 2.14 38.0 2.15 37.55 13.95 15.21 11.76

Summary of Residues and Processing Factors from the Orange Processing Study. Commodity                            Residues (ppm) [Average]                              Processing Factor[1] Fruit 0.223 0.236 [0.242] 0.267                                        _ Oil < 0.005  < 0.005 [<0.005] < 0.005                                    <0.02 Juice 0.006 0.007 [0.006] 0.006                                      0.03X Dried Pulp 0.417 0.406 [0.406] 0.396                                      1.68X [1]Processing factor from RAC, calculated from the average residues.

Tolerance Derivation

Tolerances for residues of clothianidin in/on strawberry, citrus, and tea were derived using the Organization for Economic Cooperation and Development Maximum Residue Level (OECD MRL) Calculation Procedures.  The data and results are summarized below.  For the citrus crop group, the representative crops were analyzed separately and the highest recommended MRL of 0.6 ppm from grapefruit was selected as the appropriate tolerance for the crop group.  For citrus pulp, HED used the greatest HAFT from the field trial for citrus (0.281 ppm from grapefruit) and multiplied it by the processing factor for dried pulp (1.68X).  The resulting value (0.47 ppm) is less than the recommended tolerance for residues in/on citrus.  Therefore, a separate tolerance for dried citrus pulp is not required.

For tea, HED performed an analysis of variance of the 3- and 7-day PHI residue values.  That analysis indicated that there was no significant difference in residues from these PHI groups (see ANOVA table below); therefore, the data from the 3- and 7-day PHI trials were pooled for the tolerance analysis.

Summary of Inputs and Results from the OECD MRL Calculation Procedures for Strawberry, Citrus, and Tea. Compound Clothianidin Clothianidin Clothianidin Clothianidin Clothianidin Crop Strawberry Lemon Grapefruit Orange Tea GAP 1-Day PHI 1-Day PHI 1-Day PHI 1-Day PHI 3- and 7-Day PHI Total number of data (n) 10 6 5 13 12 Percentage of censored data 0 0 0.286 0 0 Number of non-censored data 10 6 5 13 12 Lowest residue 0.103 0.034 0.027 0.008 2.150 Highest residue 1.120 0.176 0.281 0.219 37.550 Median residue 0.258 0.102 0.072 0.057 13.950 Mean 0.327 0.107 0.113 0.083 15.214 Standard deviation (SD) 0.301 0.055 0.103 0.066 11.757 Correction factor for censoring (CF) 1.000 1.000 1.000 1.000 1.000                              Proposed MRL estimate - Highest residue 1.120 0.176 0.281 0.219 37.550 - Mean + 4 SD 1.529 0.325 0.526 0.347 62.243 - CF x 3 Mean 0.981 0.321 0.339 0.249 45.641 Unrounded MRL 1.529 0.325 0.526 0.347 62.243 Rounded MRL 1.5 0.4 0.6 0.4 70 Notes -- High uncertainty of MRL estimate due to small dataset. High uncertainty of MRL estimate due to small dataset. -- --

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

1.12 0.128 0.14 0.032 21.15

0.23 0.074 0.281 0.029 10.75

0.405 0.1755 0.04675 0.044 18.45

0.405 0.155 0.0265 0.131 10.05

0.3 0.034 0.0715 0.2185 18.15

0.285 0.075

0.204 5.34

0.205

0.0415 34.6

0.11

0.0755 2.15

0.1085

0.1015 37.55

0.103

0.043 2.23

0.0925 17.15

0.0075 4.995

0.057

* Values are less than the limit of quantitation.

Single-Factor Analysis of Variance of Clothianidin Residues in Tea Comparing 3- and 7-Day PHI.                                     SUMMARY                                     Groups                                      Count                                       Sum                                     Average                                    Variance

3-day                                                                               4                                                                            60.4                                                                            15.1                                                                           30.75

7-day                                                                               8                                                                         122.165                                                                        15.27063                                                                        204.0332

                                     ANOVA Source of Variation SS df MS F P-value F crit Between Groups                                                                        0.077634                                                                               1                                                                        0.077634                                                                        0.000511                                                                        0.982417                                                                        4.964603 Within Groups                                                                        1520.483                                                                              10                                                                        152.0483

Total                                                                         1520.56                                                                              11

Summary of Clothianidin Residue Chemistry Database

Nomenclature and Physicochemical Properties

Clothianidin Nomenclature. Parent Compound                                                                                Common name Clothianidin Company experimental name TI-435, V-10066 IUPAC name (E)-1-(2-Chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine CAS name (E)-N-[(2-Chloro-5-thiazolyl)methyl]-N'-methyl-N"-nitroguanidine CAS registry number 210880-92-5 (formerly 205510-53-8) Molecular wt. 249.68 End-use product (EP) 50% WDG (Arena[(R)] 50 WDG; EPA Reg. No. 59639-152) 2.13 lb/gal FlC (V-10170 2.13 SC; EPA Reg. No. 59639-150) 5 lb/gal FlC (V-10170 5 FS; EPA Reg. No. 59639-151) Metabolite                                                                                Common name Thiazolylmethylguanidine Company experimental name TMG IUPAC name N-(2-chlorothiazol-5-yl)-N'-methylguanidine CAS Name N-(2-chlorothiazol-5-yl)-N'-methylguanidine CAS registry number 635283-91-9 Molecular wt. 204.68

Physicochemical Properties of Clothianidin. Parameter Value Reference Melting point (ºC) 176.8 D335355, W. Drew, 10/16/07 pH at 23ºC 6.24 (1% solution/suspension)

Density (g/cm[3]) 1.61 (PAI), 1.59 (TGAI)

Water solubility (g/L at 20ºC) 0.327

Solvent solubility (g/L at 25ºC) Acetone	15.2	Dichloromethane	1.32 Ethyl acetate	2.03	Heptane 	<0.00104 Methanol	6.26	Octanol	0.938 Xylene	0.0128

Vapor pressure (Pa at 20ºC) 1.3 x 10 [-10]

Dissociation constant, pKa at 20ºC 11.09

Octanol/water partition coefficient, Log(KOW) at 25ºC 0.7

UV/visible absorption spectrum (Maximum, nm) 265.5 (acidic or neutral) 246.0 (basic)

PAI = Purified Active Ingredient; TGAI = technical grade active ingredient.

Nature of the Residue  -  Plants

Based on the available metabolism studies, HED has concluded that the nature of the residue has been adequately delineated, and that parent only is the residue of concern to be used in risk assessment and the tolerance expression for most primary crops.  However, for root crops and leafy vegetables TMG is also a residue of concern for risk assessment.

Nature of the Residue  -  Livestock

The nature of clothianidin residues in livestock is understood based on the adequate goat and hen metabolism studies.  The residue definition for tolerance enforcement is clothianidin.  For risk assessment, the residue definition for ruminants is clothianidin, TZU, TZG, TZNG, and ATMG-Pyruvate.  For poultry, the residue definition for risk assessment is clothianidin, TZU, TZG, TZNG and ATG-Acetate.

Analytical Method

Adequate methods, based on solvent extraction and LC-MS/MS separation, identification, and quantification, are available for plant (Morse Method #Meth-164 - modified, RM-39C-1, or Bayer Method 00552) and livestock (Bayer Method 00624) matrices.  The LOQ for clothianidin in plant commodities is 0.01 ppm, except for wheat straw (0.02 ppm), and the validated LOQs are 0.01 ppm in milk and 0.02 ppm in animal tissues.  Clothianidin and its major metabolites are not adequately recovered using any of the FDA multiresidue methods.

Meat, Milk, Poultry, and Eggs

Dried citrus pulp is considered to be a significant feed item for beef and dairy cattle.  Given the feedstuff makeup of the current livestock dietary burden (below), residues of clothianidin in dried citrus pulp do not impact the dietary burden or current tolerances for residues of clothianidin in livestock commodities.

Estimation of Dietary Burdens for Clothianidin Residues to Livestock. Feedstuff                                Dietary Component                                % Dry Matter [1]                                   % Diet [1]                               Residues  (ppm) [2]                         Dietary Contribution (ppm) [3]                                   Beef Cattle Field corn forage                                        R                                       40                                       10                                      0.10                                      0.025 Cotton gin byproducts                                        R                                       90                                        5                                       4.5                                      0.250 Sugar beet molasses                                       CC                                       75                                       10                                      0.05                                      0.007 Field corn grain                                       CC                                       88                                       70                                      0.01                                      0.008 Cottonseed meal                                       PC                                       89                                        5                                    0.02 [4]                                      0.001 TOTAL BURDEN                                       100                                                                              0.291                                  Dairy Cattle Field corn forage                                        R                                       40                                       35                                       0.1                                      0.088 Almond, hulls                                        R                                       90                                       10                                       1.5                                      0.167 Sugar beet molasses                                       CC                                       75                                       10                                      0.05                                      0.007 Field corn grain                                       CC                                       88                                       35                                      0.01                                      0.004 Cottonseed                                       PC                                       88                                       10                                      0.20                                      0.023 TOTAL BURDEN                                       100                                                                              0.289                                     Poultry Field corn grain                                       CC                                                                               75                                      0.01                                      0.008 Cottonseed meal                                       PC                                                                               20                                    0.02 [4]                                      0.004 Soybean seed                                       PC                                                                                5                                      0.02                                      0.001 TOTAL BURDEN                                       100                                                                              0.013                                      Swine Field corn grain                                       CC                                                                               85                                      0.01                                      0.009 Cottonseed meal                                       PC                                                                               15                                    0.02 [4]                                      0.003 TOTAL BURDEN                                       100                                                                              0.012 [1]	Potential dietary burdens for livestock were determined using recent Agency guidance on calculating the maximum reasonably balanced diets for livestock (memo, 6/30/2008). [2]	The tolerance level for the RAC was used for any associated processed fractions unless otherwise indicated. [3]	Contribution = ([tolerance /% DM] X % diet) for beef and dairy cattle; contribution = ([tolerance] X % diet) for poultry and swine. [4]	A residue level of 0.02 ppm was used for cottonseed meal, as the cotton processing study indicated that residues are reduced in meal by 0.1x.

Attachment 1.  International Harmonization

                   Clothianidin (044309; 11 September 2012) Summary of US and International Tolerances and Maximum Residue Limits  Residue Definition: US Canada Mexico[2] Codex[3,4] 40 CFR 180.586: Plant/Livestock:  clothianidin, ( E )- N -[(2-Chloro-5-thiazolyl)methyl]- N' -methyl- N" -nitroguanidine

[C(E)]-N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl- N"-nitroguanidine

clothianidin. The residue is not fat-soluble.

Commodity[1] Tolerance (ppm) /Maximum Residue Limit (mg/kg)

                                      US Canada Mexico[2] Codex[3,4] Tea (import only) 70

0.7 Tea, green, black (black, fermented and dried) (T) Strawberry 1.5

0.07 berries and other small fruits (except grapes) (c, T) Fruit, Citrus, Group 10-10 0.6

0.07 citrus fruits (T) Pistachio 0.01

Pepper and Eggplant (Crop Subgroup 8-10B) 0.8

0.05 fruiting vegetables other than cucurbits (T) 0.5 peppers chili, dried

Completed:  M. Negussie; 09/13/2012 [1] Includes only commodities of interest for this action.  Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes.

3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains.  PoP = processed postharvest treated commodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.

[4] The source of the residue; T-thiamethoxam; C-clothianidin