Document ID: EPA-HQ-OPP-2014-0355-0068
Agency: epa
Document Type: Rule
Title: Pesticide Tolerances: Bicyclopyrone
Posted Date: 2015-04-23T04:00Z

[Federal Register Volume 80, Number 78 (Thursday, April 23, 2015)]
[Rules and Regulations]
[Pages 22648-22654]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2015-09482]

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2014-0355; FRL-9926-66]

Bicyclopyrone; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes tolerances for residues of 
bicyclopyrone

[[Page 22649]]

in or on field corn, forage; field corn, grain; field corn, stover; 
popcorn, grain; popcorn, stover; sweet corn, forage; sweet corn, ears; 
sweet corn, stover; sugarcane, stalks; cattle, liver; goat, meat 
byproducts; sheep, meat byproducts; horse, meat byproducts; and hog, 
meat byproducts. Syngenta requested these tolerances under the Federal 
Food, Drug, and Cosmetic Act (FFDCA).

DATES: This regulation is effective April 23, 2015. Objections and 
requests for hearings must be received on or before June 22, 2015, and 
must be filed in accordance with the instructions provided in 40 CFR 
part 178 (see also Unit I.C. of the SUPPLEMENTARY INFORMATION).

ADDRESSES: The docket for this action, identified by docket 
identification (ID) number EPA-HQ-OPP-2014-0355, is available at http://www.regulations.gov or at the Office of Pesticide Programs Regulatory 
Public Docket (OPP Docket) in the Environmental Protection Agency 
Docket Center (EPA/DC), West William Jefferson Clinton Bldg., Rm. 3334, 
1301 Constitution Ave. NW., Washington, DC 20460-0001. The Public 
Reading Room is open from 8:30 a.m. to 4:30 p.m., Monday through 
Friday, excluding legal holidays. The telephone number for the Public 
Reading Room is (202) 566-1744, and the telephone number for the OPP 
Docket is (703) 305-5805. Please review the visitor instructions and 
additional information about the docket available at http://www.epa.gov/dockets.

FOR FURTHER INFORMATION CONTACT: Susan Lewis, Registration Division 
(7505P), Office of Pesticide Programs, Environmental Protection Agency, 
1200 Pennsylvania Ave. NW., Washington, DC 20460-0001; main telephone 
number: (703) 305-7090; email address: RDFRNotices@epa.gov.

SUPPLEMENTARY INFORMATION: 

I. General Information

A. Does this action apply to me?

    You may be potentially affected by this action if you are an 
agricultural producer, food manufacturer, or pesticide manufacturer. 
The following list of North American Industrial Classification System 
(NAICS) codes is not intended to be exhaustive, but rather provides a 
guide to help readers determine whether this document applies to them. 
Potentially affected entities may include:
     Crop production (NAICS code 111).
     Animal production (NAICS code 112).
     Food manufacturing (NAICS code 311).
     Pesticide manufacturing (NAICS code 32532).

B. How can I get electronic access to other related information?

    You may access a frequently updated electronic version of EPA's 
tolerance regulations at 40 CFR part 180 through the Government 
Publishing Office's e-CFR site at http://www.ecfr.gov/cgi-bin/text-idx?&c=ecfr&tpl=/ecfrbrowse/Title40/40tab_02.tpl

C. How can I file an objection or hearing request?

    Under FFDCA section 408(g), 21 U.S.C. 346a, any person may file an 
objection to any aspect of this regulation and may also request a 
hearing on those objections. You must file your objection or request a 
hearing on this regulation in accordance with the instructions provided 
in 40 CFR part 178. To ensure proper receipt by EPA, you must identify 
docket ID number EPA-HQ-OPP-2014-0355 in the subject line on the first 
page of your submission. All objections and requests for a hearing must 
be in writing, and must be received by the Hearing Clerk on or before 
June 22, 2015. Addresses for mail and hand delivery of objections and 
hearing requests are provided in 40 CFR 178.25(b).
    In addition to filing an objection or hearing request with the 
Hearing Clerk as described in 40 CFR part 178, please submit a copy of 
the filing (excluding any Confidential Business Information (CBI)) for 
inclusion in the public docket. Information not marked confidential 
pursuant to 40 CFR part 2 may be disclosed publicly by EPA without 
prior notice. Submit the non-CBI copy of your objection or hearing 
request, identified by docket ID number EPA-HQ-OPP-2014-0355, by one of 
the following methods:
     Federal eRulemaking Portal: http://www.regulations.gov. 
Follow the online instructions for submitting comments. Do not submit 
electronically any information you consider to be CBI or other 
information whose disclosure is restricted by statute.
     Mail: OPP Docket, Environmental Protection Agency Docket 
Center (EPA/DC), (28221T), 1200 Pennsylvania Ave. NW., Washington, DC 
20460-0001.
     Hand Delivery: To make special arrangements for hand 
delivery or delivery of boxed information, please follow the 
instructions at http://www.epa.gov/dockets/contacts.html.
    Additional instructions on commenting or visiting the docket, along 
with more information about dockets generally, is available at http://www.epa.gov/dockets.

II. Summary of Petitioned-For Tolerance

    In the Federal Register of September 5, 2014 (79 FR 53009) (FRL-
9914-98), EPA issued a document pursuant to FFDCA section 408(d)(3), 21 
U.S.C. 346a(d)(3), announcing the filing of a pesticide petition (PP 
3F8225) by Syngenta Crop Protection, LLC., P.O. Box 18300, Greensboro, 
NC 27419. The petition requested that 40 CFR part 180 be amended by 
establishing tolerances for residues of the herbicide bicyclopyrone, 
herbicide, in or on field corn, forage at 0.4 parts per million (ppm); 
field corn, grain at 0.02 ppm; field corn, stover at 0.5 ppm; popcorn, 
grain at 0.02 ppm; popcorn, stover at 0.5 ppm; sweet corn, forage at 
0.4 ppm; sweet corn, ears at 0.02 ppm; sweet corn, stover at 0.5 ppm; 
sugarcane, stalks at 0.01 ppm; and cattle, liver at 0.06 ppm. That 
document referenced a summary of the petition prepared by Syngenta Crop 
Protection, LLC., the registrant, which is available in the docket, 
http://www.regulations.gov. In the Federal Register of February 11, 
2015 (80 FR 7559) (FRL-9921-94), EPA published a corrected notice of 
filing for the import tolerance on sugarcane petition. Comments were 
received for both items. EPA's response to these comments is discussed 
in Unit IV.C.
    Based upon review of the data supporting the petition, EPA has 
revised the proposed tolerances to corn, field, forage at 0.30 ppm; 
corn, field, grain at 0.02 ppm; corn, field, stover at 0.40 ppm; corn, 
pop, grain at 0.02 ppm; corn, pop, stover at 0.40 ppm; corn, sweet, 
forage at 0.40 ppm; corn, sweet, kernel plus cob with husks removed at 
0.03 ppm; corn, sweet, stover at 0.70 ppm; sugarcane, cane at 0.02 ppm; 
cattle, meat byproducts at 1.5 ppm; goat, meat byproducts at 1.5 ppm; 
sheep, meat byproducts at 1.5 ppm; horse, meat byproducts at 1.5 ppm; 
and hog, meat byproducts at 0.15 ppm. The reasons for these changes are 
explained in Unit IV.C.

III. Aggregate Risk Assessment and Determination of Safety

    Section 408(b)(2)(A)(i) of FFDCA allows EPA to establish a 
tolerance (the legal limit for a pesticide chemical residue in or on a 
food) only if EPA determines that the tolerance is ``safe.'' Section 
408(b)(2)(A)(ii) of FFDCA defines ``safe'' to mean that ``there is a 
reasonable certainty that no harm will result from aggregate exposure 
to the pesticide chemical residue, including all anticipated dietary 
exposures and all other exposures for which there is reliable 
information.'' This includes

[[Page 22650]]

exposure through drinking water and in residential settings, but does 
not include occupational exposure. Section 408(b)(2)(C) of FFDCA 
requires EPA to give special consideration to exposure of infants and 
children to the pesticide chemical residue in establishing a tolerance 
and to ``ensure that there is a reasonable certainty that no harm will 
result to infants and children from aggregate exposure to the pesticide 
chemical residue . . .''
    Consistent with FFDCA section 408(b)(2)(D), and the factors 
specified in FFDCA section 408(b)(2)(D), EPA has reviewed the available 
scientific data and other relevant information in support of this 
action. EPA has sufficient data to assess the hazards of and to make a 
determination on aggregate exposure for bicyclopyrone including 
exposure resulting from the tolerances established by this action. 
EPA's assessment of exposures and risks associated with bicyclopyrone 
follows.

A. Toxicological Profile

    EPA has evaluated the available toxicity data and considered its 
validity, completeness, and reliability as well as the relationship of 
the results of the studies to human risk. EPA has also considered 
available information concerning the variability of the sensitivities 
of major identifiable subgroups of consumers, including infants and 
children.
    The effects of bicyclopyrone are indicative of inhibition of 4-
hydroxyphenylpyruvate dioxygenase (HPPD). Plasma tyrosine levels were 
consistently elevated in rats, rabbits, and dogs (levels in mice were 
not tested). Consistent with these elevated tyrosine levels, ocular 
effects (corneal opacity, keratitis) were observed for subchronic and 
chronic durations through the oral and dermal routes in rats, which was 
the most sensitive species tested (minor instances in dogs). There were 
also increased incidences of thyroid follicular hyperplasia and a 
chronic progressive nephropathy. While minor instances of ocular 
effects were observed in dogs, different toxicological effects were 
generally observed. For subchronic oral exposure, clinical signs 
(moderate hypoactivity, slightly unsteady gait, increased heart rate, 
regurgitation, and vomiting) were observed, and clinical pathological 
indicators of toxicity occurred in the eye and the thymus. Following 
chronic exposure, there was a dose-dependent increase in chromatolysis 
and swelling of selected neurons in the dorsal root ganglia, and 
degeneration of nerve fibers in the spinal nerve roots in both sexes. 
In one female dog at the high dose, corneal opacity and light 
sensitivity were observed.
    Across the database, there were decreased absolute body weights 
(the only finding in mice for any duration) and food consumption. There 
were no signs of immunotoxicity or neurotoxicity in rodents.
    Bicyclopyrone treatment resulted in developmental toxicity in both 
rats and rabbits, and there was an increased quantitative fetal 
susceptibility in both species tested. In rats, maternal toxicity was 
not observed up to 1000 mg/kg/day. Fetal effects occurred at all doses 
(>=100 mg/kg/day), and manifested as skeletal variations (increased 
incidences of full or rudimentary supernumerary ribs, pelvic girdle 
malpositioned caudal, costal cartilage 11 long). In New Zealand White 
rabbits, maternal effects consisted of mortality/moribundity in 
conjunction with minimal food consumption at 200 mg/kg/day. Fetal 
effects once again occurred at all doses tested (>=10 mg/kg/day). The 
sole fetal effect at the lowest dose tested was the appearance of the 
27th presacral vertebrae. There were two studies in Himalayan rabbits. 
In both studies, maternal effects consisted of macroscopic findings in 
the stomach wall and an increased incidence of post-implantation loss 
at the 250 mg/kg/day dose level. In the first study, fetal effects 
occurred starting at 50 mg/kg/day and consisted of skeletal variations 
(increased incidence of the 27th prepelvic vertebra and malpositioned 
pelvic girdle). In the second study, the increased quantitative fetal 
susceptibility was not observed due to a change in the dose selection. 
Fetal effects occurred at 250 mg/kg/day and consisted of external, 
visceral, and skeletal abnormalities, and visceral variations, 
skeletal, bone and cartilage variations. In total, the effects in these 
studies are consistent with effects of other chemicals in this class.
    In the two-generation reproductive study in rats, ocular toxicity 
occurred in parents and offspring and there was no increased offspring 
susceptibility of any kind. Reproductive effects included changes in 
sperm parameters, and a decrease of precoital interval.
    To determine the mechanism for the thyroid hyperplasia observed in 
the chronic/carcinogenicity study in rats, two mode-of-action studies 
were performed. In the in vitro study, bicyclopyrone was negative for 
thyroid peroxidase inhibition. The results from the in vivo study 
suggested that the observed thyroid hyperplasia was the result of 
increased metabolism of thyroid hormones indicated by (1) decreased 
plasma T3 and T4 levels, (2) increased thyroid follicular cell 
hypertrophy, (3) increased liver weights associated, and (4) increased 
hepatocellular centrilobular hypertrophy and increased hepatic uridine 
diphosphate glucuronyl transferase (UDPGT) activities.
    Bicyclopyrone is categorized as having low acute lethality via all 
routes of administration (Categories III and IV). Bicyclopyrone 
produces minimal eye irritation and mild acute inhalation toxicity 
(Toxicity Category IV).
    Specific information on the studies received and the nature of the 
adverse effects caused by bicyclopyrone as well as the lowest-observed-
adverse-effect-level (LOAEL) from the toxicity studies can be found at 
http://www.regulations.gov in document titled ``Bicyclopyrone: Human 
Health Risk Assessment for the Section 3 Registration Action on Corn 
and the Establishment of Permanent Tolerances for Residues in/on Corn 
and Imported Sugarcane'' at pp. 30-37 in docket ID number EPA-HQ-OPP-
2014-0355.

B. Toxicological Points of Departure/Levels of Concern

    Once a pesticide's toxicological profile is determined, EPA 
identifies toxicological points of departure (POD) and levels of 
concern to use in evaluating the risk posed by human exposure to the 
pesticide. For hazards that have a threshold below which there is no 
appreciable risk, the toxicological POD is used as the basis for 
derivation of reference values for risk assessment. PODs are developed 
based on a careful analysis of the doses in each toxicological study to 
determine the dose at which no adverse effects are observed (the NOAEL) 
and the lowest dose at which adverse effects of concern are identified 
(the LOAEL). Uncertainty/safety factors are used in conjunction with 
the POD to calculate a safe exposure level--generally referred to as a 
population-adjusted dose (PAD) or a reference dose (RfD)--and a safe 
margin of exposure (MOE). For non-threshold risks, the Agency assumes 
that any amount of exposure will lead to some degree of risk. Thus, the 
Agency estimates risk in terms of the probability of an occurrence of 
the adverse effect expected in a lifetime. For more information on the 
general principles EPA uses in risk characterization and a complete 
description of the risk assessment process, see http://www.epa.gov/pesticides/factsheets/riskassess.htm.
    A summary of the toxicological endpoints for bicyclopyrone used for 
human risk assessment is shown in Table 1 of this unit.

[[Page 22651]]

 Table 1--Summary of Toxicological Doses and Endpoints for Bicyclopyrone for Use in Human Health Risk Assessment
----------------------------------------------------------------------------------------------------------------
                                    Point of departure
        Exposure/scenario            and uncertainty/     RfD, PAD, LOC for     Study and toxicological effects
                                      safety factors       risk assessment
----------------------------------------------------------------------------------------------------------------
Acute dietary (Females 13-49       LOAEL = 10 mg/kg/day  Acute RfD = 0.01 mg/ Prenatal Developmental Study (New
 years of age).                    UFA = 10x...........   kg/day.              Zealand White Rabbits).
                                   UFH = 10x...........  aPAD = 0.01 mg/kg/   Developmental LOAEL = 10 mg/kg/day
                                   FQPA SF/UFL = 10x...   day.                 based on skeletal variations (the
                                                                               appearance of the 27th presacral
                                                                               vertebrae).
Acute dietary (General population  No endpoint
 including infants and children).   attributable to a
                                    single dose and
                                    appropriate for the
                                    U.S. general
                                    population was seen
                                    in the
                                    bicyclopyrone
                                    toxicological
                                    database;
                                    therefore, an acute
                                    dietary point of
                                    departure for the
                                    general U.S.
                                    population was not
                                    established.
Chronic dietary (All populations)  LOAEL= 10 mg/kg/day.  Chronic RfD =        Carcinogenicity Study (rat).
                                   UFA = 10x...........   0.00028 mg/kg/day.  LOAEL = 0.28/0.35 mg/kg/day (Male/
                                   UFH = 10x...........  cPAD = 0.00028 mg/    Female) based on a dose dependent
                                   FQPA SF/UFL = 10x...   kg/day.              increase in the incidence of
                                                                               opaque eyes and corneal damage in
                                                                               both sexes compared to controls,
                                                                               an increased incidence of thyroid
                                                                               follicular hyperplasia in males,
                                                                               and an increased incidence of
                                                                               chronic progressive nephropathy
                                                                               in the kidneys of males.
Dermal Short- (1-30 days) and      LOAEL = 10 mg/kg/day  LOC for MOE = 1000.  Prenatal Developmental Study (New
 Intermediate-Term (1-6 months).   DAF = 20.44%........                        Zealand White Rabbits).
                                   UFA = 10x...........                       Developmental LOAEL = 10 mg/kg/day
                                   UFH = 10x...........                        based on skeletal variations (the
                                   FQPA SF/UFL = 10x...                        appearance of the 27th presacral
                                                                               vertebrae).
Inhalation Short- (1-30 days) and  LOAEL = 10 mg/kg/day  LOC for MOE = 1000.  Prenatal Developmental Study (New
 Intermediate-Term (1-6 months).   UFA = 10x...........                        Zealand White Rabbits).
                                   UFH = 10x...........                       Developmental LOAEL = 10 mg/kg/day
                                   FQPA SF/UFL = 10x...                        based on skeletal variations (the
                                                                               appearance of the 27th presacral
                                                                               vertebrae.
Cancer (Oral, dermal, inhalation)  Classification:
                                    ``Suggestive
                                    evidence of
                                    cancer'' based on
                                    the presence of
                                    rare ocular tumors
                                    in male rats.
                                    Quantification of
                                    bicyclopyrone's
                                    carcinogenic
                                    potential is not
                                    required. A non-
                                    linear approach
                                    (i.e., RfD) will
                                    adequately account
                                    for all chronic
                                    toxicity, including
                                    carcinogenicity
                                    that could result
                                    from exposure to
                                    bicyclopyrone.
----------------------------------------------------------------------------------------------------------------
FQPA SF = Food Quality Protection Act Safety Factor. LOAEL = lowest-observed-adverse-effect-level. LOC = level
  of concern. mg/kg/day = milligram/kilogram/day. MOE = margin of exposure. PAD = population adjusted dose (a =
  acute, c = chronic). RfD = reference dose. UFA = extrapolation from animal to human (interspecies). UFH =
  potential variation in sensitivity among members of the human population (intraspecies). UFL = use of a LOAEL
  to extrapolate a NOAEL.

C. Exposure Assessment

    1. Dietary exposure from food and feed uses. In evaluating dietary 
exposure to bicyclopyrone, EPA considered exposure under the 
petitioned-for tolerances. EPA assessed dietary exposures from 
bicyclopyrone in food as follows:
    i. Acute exposure. Quantitative acute dietary exposure and risk 
assessments

[[Page 22652]]

are performed for a food-use pesticide, if a toxicological study has 
indicated the possibility of an effect of concern occurring as a result 
of a 1-day or single exposure. Such effects were identified for 
bicyclopyrone. In estimating acute dietary exposure, EPA used food 
consumption information from the United States Department of 
Agriculture (USDA) 2003-2008 Nationwide Continuing Surveys of Food 
Intake by Individuals (CSFII). The acute dietary analysis was conducted 
for bicyclopyrone assuming tolerance level residues, default processing 
factors, and 100% crop treated (CT) information.
    ii. Chronic exposure. In conducting the chronic dietary exposure 
assessment EPA used the food consumption data from the USDA 2003-2008 
CSFII. The chronic dietary exposure assessment was conducted for 
bicyclopyrone assuming average field trial residues for crops, 
tolerance-level residues for livestock commodities, default processing 
factors, and 100% CT information.
    iii. Cancer. Based on the data summarized in Unit III.A., EPA has 
concluded that bicyclopyrone should be classified as ``suggestive 
evidence of cancer'' based on the presence of rare ocular tumors in 
male rats. Quantification of bicyclopyrone's carcinogenic potential is 
not required. A non-linear approach (i.e., RfD) will adequately account 
for all chronic toxicity, including carcinogenicity that could result 
from exposure to bicyclopyrone. Using EPA's non-linear approach, the 
1000X combined uncertainty factor used to calculate the cRfD/cPAD for 
the chronic dietary assessment, generates a dose which is 100,000-fold 
lower than the dose at which the ocular tumors were observed and is 
thus protective of their potential formation.
    2. Dietary exposure from drinking water. The Agency used screening 
level water exposure models in the dietary exposure analysis and risk 
assessment for bicyclopyrone in drinking water. These simulation models 
take into account data on the physical, chemical, and fate/transport 
characteristics of bicyclopyrone. Further information regarding EPA 
drinking water models used in pesticide exposure assessment can be 
found at http://www.epa.gov/oppefed1/models/water/index.htm.
    The Surface Water Concentration Calculator (SWCC) computer model 
was used to generate surface water Estimated Drinking Water 
Concentrations (EDWCs), while the Pesticide Root Zone Model for 
Groundwater (PRZM-GW) and the Screening Concentration in Ground Water 
(SCI-GROW) models were used to generate groundwater EDWCs.
    The maximum acute and chronic surface water EDWCs associated with 
bicyclopyrone use on corn were 2.87 and 0.857 [micro]g/L, respectively. 
For groundwater sources of drinking water, the maximum acute and 
chronic EDWCs of bicyclopyrone in shallow groundwater from PRZM-GW were 
3.76 and 3.23 [mu]g/L, respectively. EDWCs of 0.00376 ppm and 0.00323 
ppm were used in the acute and chronic analyses, respectively.
    3. From non-dietary exposure. The term ``residential exposure'' is 
used in this document to refer to non-occupational, non-dietary 
exposure (e.g., for lawn and garden pest control, indoor pest control, 
termiticides, and flea and tick control on pets). Bicyclopyrone is not 
registered for any specific use patterns that would result in 
residential exposure.
    4. Cumulative effects from substances with a common mechanism of 
toxicity. Section 408(b)(2)(D)(v) of FFDCA requires that, when 
considering whether to establish, modify, or revoke a tolerance, the 
Agency consider ``available information'' concerning the cumulative 
effects of a particular pesticide's residues and ``other substances 
that have a common mechanism of toxicity.''
    There are marked differences among species in the ocular toxicity 
associated with bicyclopyrone's mechanism of toxicity, the inhibition 
of HPPD. Ocular effects following treatment with HPPD inhibitor 
herbicides are seen in the rat but not in the mouse. Monkeys also seem 
to be recalcitrant to the ocular toxicity induced by HPPD inhibition. 
One explanation for this species-specific response in ocular opacity 
may be related to species differences in the clearance of tyrosine. A 
metabolic pathway exists to remove tyrosine from the blood that 
involves the liver enzyme tyrosine aminotransferase (TAT). In contrast 
to rats where ocular toxicity is observed following exposure to HPPD-
inhibiting herbicides, mice and humans are unlikely to achieve the 
levels of plasma tyrosine necessary to produce ocular opacities because 
the activity of TAT in these species is much greater compared to rats.
    HPPD inhibitors (e.g., nitisinone) are used as an effective 
therapeutic agent to treat patients suffering from rare genetic 
diseases of tyrosine catabolism. Treatment starts in childhood but is 
often sustained throughout patient's lifetime. The human experience 
indicates that a therapeutic dose (1 mg/kg/day dose) of nitisinone has 
an excellent safety record in infants, children, and adults and that 
serious adverse health outcomes have not been observed in a population 
followed for approximately a decade. Rarely, ocular effects are seen in 
patients with high plasma tyrosine levels; however, these effects are 
transient and can be readily reversed upon adherence to a restricted 
protein diet. This observation indicates that an HPPD inhibitor in and 
of itself cannot easily overwhelm the tyrosine-clearance mechanism in 
humans.
    Therefore, exposures to environmental residues of HPPD-inhibiting 
herbicides are unlikely to result in the high blood levels of tyrosine 
and ocular toxicity in humans due to an efficient metabolic process to 
handle excess tyrosine. The EPA continues to study the complex 
relationships between elevated tyrosine levels and biological effects 
in various species. In the future, assessments of HPPD-inhibiting 
herbicides may consider more appropriate models and cross species 
extrapolation methods. EPA has not conducted cumulative risk assessment 
with other HPPD inhibitors.

D. Safety Factor for Infants and Children

    1. In general. Section 408(b)(2)(C) of FFDCA provides that EPA 
shall apply an additional tenfold (10X) margin of safety for infants 
and children in the case of threshold effects to account for prenatal 
and postnatal toxicity and the completeness of the database on toxicity 
and exposure unless EPA determines based on reliable data that a 
different margin of safety will be safe for infants and children. This 
additional margin of safety is commonly referred to as the FQPA Safety 
Factor (SF). In applying this provision, EPA either retains the default 
value of 10X, or uses a different additional safety factor when 
reliable data available to EPA support the choice of a different 
factor.
    2. The FQPA SF is retained at 10X for all exposure scenarios based 
on use of a LOAEL for the points of departure. The toxicology database 
for bicyclopyrone is adequate for characterizing toxicity and 
quantification of risk for food and non-food uses; however, a LOAEL 
from the New Zealand white rabbit developmental and chronic/
carcinogenicity rat toxicity studies has been used as the POD for 
several scenarios.
    There is no evidence of neurotoxicity in either of the 
neurotoxicity screening batteries, but there are effects in the chronic 
dog study. The level of concern is low, however, since the study and 
POD chosen for the chronic dietary exposure scenario is protective of 
these

[[Page 22653]]

effects. There is evidence of increased quantitative fetal 
susceptibility following in utero exposure in both rats and rabbits; 
however, these effects are well characterized and the selected 
endpoints are protective of the observed fetal effects. Lastly, there 
are no residual uncertainties in the exposure database.

E. Aggregate Risks and Determination of Safety

    EPA determines whether acute and chronic dietary pesticide 
exposures are safe by comparing aggregate exposure estimates to the 
acute PAD (aPAD) and chronic PAD (cPAD). For linear cancer risks, EPA 
calculates the lifetime probability of acquiring cancer given the 
estimated aggregate exposure. Short-, intermediate-, and chronic-term 
risks are evaluated by comparing the estimated aggregate food, water, 
and residential exposure to the appropriate PODs to ensure that an 
adequate MOE exists.
    Because there are no uses for bicyclopyrone that may result in 
residential exposures, the aggregate risk consists only of food and 
water.
    1. Acute risk. Using the exposure assumptions discussed in this 
unit for acute exposure, the acute dietary exposure from food and water 
to bicyclopyrone will occupy 2.9% of the aPAD for females 13-49 years 
old, the population group receiving the greatest exposure.
    2. Chronic risk. Using the exposure assumptions described in this 
unit for chronic exposure, EPA has concluded that chronic exposure to 
bicyclopyrone from food and water will utilize 91% of the cPAD for 
children 1-2 years old the population group receiving the greatest 
exposure. There are no residential uses for bicyclopyrone.
    3. Short-term risk. A short-term adverse effect was identified; 
however, bicyclopyrone is not registered for any use patterns that 
would result in short-term residential exposure. Short-term risk is 
assessed based on short-term residential exposure plus chronic dietary 
exposure. Because there is no short-term residential exposure and 
chronic dietary exposure has already been assessed under the 
appropriately protective cPAD (which is at least as protective as the 
POD used to assess short-term risk), no further assessment of short-
term risk is necessary, and EPA relies on the chronic dietary risk 
assessment for evaluating short-term risk for bicyclopyrone.
    4. Intermediate-term risk. An intermediate-term adverse effect was 
identified; however, bicyclopyrone is not registered for any use 
patterns that would result in intermediate-term residential exposure. 
Intermediate-term risk is assessed based on intermediate-term 
residential exposure plus chronic dietary exposure. Because there is no 
intermediate-term residential exposure and chronic dietary exposure has 
already been assessed under the appropriately protective cPAD (which is 
at least as protective as the POD used to assess intermediate-term 
risk), no further assessment of intermediate-term risk is necessary, 
and EPA relies on the chronic dietary risk assessment for evaluating 
intermediate-term risk for bicyclopyrone.
    5. Aggregate cancer risk for U.S. population. A non-linear approach 
(i.e., RfD) will adequately account for all chronic toxicity, including 
carcinogenicity that could result from exposure to bicyclopyrone.
    6. Determination of safety. Based on these risk assessments, EPA 
concludes that there is a reasonable certainty that no harm will result 
to the general population, or to infants and children from aggregate 
exposure to bicyclopyrone residues.

IV. Other Considerations

A. Analytical Enforcement Methodology

    Adequate enforcement methodology liquid chromatography-mass 
spectroscopy/mass spectroscopy (LC-MS/MS) methods for tolerance 
enforcement have been developed and independently validated. For all 
matrices and analytes, the level of quantification (LOQ), defined as 
the lowest spiking level where acceptable precision and accuracy data 
were obtained, was determined to be 0.01 ppm for each of the common 
moieties, SYN503780 and CSCD686480, for a combined LOQ of 0.02 ppm is 
available to enforce the tolerance expression.
    The method may be requested from: Chief, Analytical Chemistry 
Branch, Environmental Science Center, 701 Mapes Rd., Ft. Meade, MD 
20755-5350; telephone number: (410) 305-2905; email address: 
residuemethods@epa.gov.

B. International Residue Limits

    In making its tolerance decisions, EPA seeks to harmonize U.S. 
tolerances with international standards whenever possible, consistent 
with U.S. food safety standards and agricultural practices. EPA 
considers the international maximum residue limits (MRLs) established 
by the Codex Alimentarius Commission (Codex), as required by FFDCA 
section 408(b)(4). The Codex Alimentarius is a joint United Nations 
Food and Agriculture Organization/World Health Organization food 
standards program, and it is recognized as an international food safety 
standards-setting organization in trade agreements to which the United 
States is a party. EPA may establish a tolerance that is different from 
a Codex MRL; however, FFDCA section 408(b)(4) requires that EPA explain 
the reasons for departing from the Codex level. The Codex has not 
established a MRL for bicyclopyrone.

C. Response to Comments

    Seven comments were received in response to the September 5, 2014 
notice of filing. Three of the comments were relevant to bicyclopyrone, 
the other four comments were relevant to other actions that were 
batched together with bicyclopryone in the same Federal Register 
document. The commenters noted that pesticides and bicyclopyrone pose a 
risk to pollinators. The agency has determined that bicyclopyrone is 
moderately to practically non-toxic to young adult honey bees (Apis 
mellifera) on an acute exposure basis.
    One comment was received in response to the February 11, 2015 
corrected notice of filing for the import tolerance on sugarcane 
petition. This comment was associated with an action that was batched 
together with bicyclopyrone in the same Federal Register document and 
was not relevant to bicyclopyrone.

D. Revisions to Petitioned-For Tolerances

    The proposed tolerance levels for most corn (field, pop, and sweet) 
raw agricultural commodities (RAC) differ slightly from those being set 
by the EPA. Although both the registrant and EPA have used the OECD 
(Organization for Economic Cooperation and Development) calculation 
procedures to obtain tolerance levels, EPA only included data from 
trials conducted according to the proposed label directions. The 
registrant proposed a tolerance level for sugarcane, cane below the 
method LOQ (0.01 ppm); the appropriate level is at the LOQ (0.02 ppm). 
EPA's tolerance levels for livestock meat byproducts were based on the 
highest tissue-to-feed ratio calculated from the dose closest to 
maximum dietary burdens. As residues are expected in both liver and 
kidney, the appropriate RAC is ``meat byproducts.'' Per EPA policy, 
tolerances are set for all ruminants, not just cattle. EPA made 
numerous changes in the commodity definitions and revisions to the 
tolerance expression in order to conform to current Agency policy.

[[Page 22654]]

V. Conclusion

    Therefore, tolerances are established for residues of the herbicide 
bicyclopyrone in or on corn, field, forage at 0.30 ppm; corn, field, 
grain at 0.02 ppm; corn, field, stover at 0.40 ppm; corn, pop, grain at 
0.02 ppm; corn, pop, stover at 0.40 ppm; corn, sweet, forage at 0.40 
ppm; corn, sweet, kernel plus cob with husks removed at 0.03 ppm; corn, 
sweet, stover at 0.70 ppm; sugarcane, cane at 0.02 ppm; cattle, meat 
byproducts at 1.5 ppm; goat, meat byproducts at 1.5 ppm; sheep, meat 
byproducts at 1.5 ppm; horse, meat byproducts at 1.5 ppm; and hog, meat 
byproducts at 0.15 ppm

VI. Statutory and Executive Order Reviews

    This action establishes tolerances under FFDCA section 408(d) in 
response to a petition submitted to the Agency. The Office of 
Management and Budget (OMB) has exempted these types of actions from 
review under Executive Order 12866, entitled ``Regulatory Planning and 
Review'' (58 FR 51735, October 4, 1993). Because this action has been 
exempted from review under Executive Order 12866, this action is not 
subject to Executive Order 13211, entitled ``Actions Concerning 
Regulations That Significantly Affect Energy Supply, Distribution, or 
Use'' (66 FR 28355, May 22, 2001) or Executive Order 13045, entitled 
``Protection of Children from Environmental Health Risks and Safety 
Risks'' (62 FR 19885, April 23, 1997). This action does not contain any 
information collections subject to OMB approval under the Paperwork 
Reduction Act (PRA) (44 U.S.C. 3501 et seq.), nor does it require any 
special considerations under Executive Order 12898, entitled ``Federal 
Actions to Address Environmental Justice in Minority Populations and 
Low-Income Populations'' (59 FR 7629, February 16, 1994).
    Since tolerances and exemptions that are established on the basis 
of a petition under FFDCA section 408(d), such as the tolerance in this 
final rule, do not require the issuance of a proposed rule, the 
requirements of the Regulatory Flexibility Act (RFA) (5 U.S.C. 601 et 
seq.), do not apply.
    This action directly regulates growers, food processors, food 
handlers, and food retailers, not States or tribes, nor does this 
action alter the relationships or distribution of power and 
responsibilities established by Congress in the preemption provisions 
of FFDCA section 408(n)(4). As such, the Agency has determined that 
this action will not have a substantial direct effect on States or 
tribal governments, on the relationship between the national government 
and the States or tribal governments, or on the distribution of power 
and responsibilities among the various levels of government or between 
the Federal Government and Indian tribes. Thus, the Agency has 
determined that Executive Order 13132, entitled ``Federalism'' (64 FR 
43255, August 10, 1999) and Executive Order 13175, entitled 
``Consultation and Coordination with Indian Tribal Governments'' (65 FR 
67249, November 9, 2000) do not apply to this action. In addition, this 
action does not impose any enforceable duty or contain any unfunded 
mandate as described under Title II of the Unfunded Mandates Reform Act 
(UMRA) (2 U.S.C. 1501 et seq.).
    This action does not involve any technical standards that would 
require Agency consideration of voluntary consensus standards pursuant 
to section 12(d) of the National Technology Transfer and Advancement 
Act (NTTAA) (15 U.S.C. 272 note).

VII. Congressional Review Act

    Pursuant to the Congressional Review Act (5 U.S.C. 801 et seq.), 
EPA will submit a report containing this rule and other required 
information to the U.S. Senate, the U.S. House of Representatives, and 
the Comptroller General of the United States prior to publication of 
the rule in the Federal Register. This action is not a ``major rule'' 
as defined by 5 U.S.C. 804(2).

List of Subjects in 40 CFR Part 180

    Environmental protection, Administrative practice and procedure, 
Agricultural commodities, Pesticides and pests, Reporting and 
recordkeeping requirements.

    Dated: April 17, 2015.
William Jordan,
Acting Director, Office of Pesticide Programs.

    Therefore, 40 CFR chapter I is amended as follows:

PART 180--[AMENDED]

0
1. The authority citation for part 180 continues to read as follows:

    Authority:  21 U.S.C. 321(q), 346a and 371.

0
2. Add Sec.  180.682 to subpart C to read as follows:

Sec.  180.682  Bicyclopyrone; tolerances for residues.

    (a) General. (1) Tolerances are established for residues of the 
herbicide bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-
(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), 
including its metabolites and degradates, in or on the commodities in 
the table below. Compliance with the tolerance levels specified below 
is to be determined by measuring only the sum of the common moieties 
SYN503780 (2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-
pyridinecarboxylic acid) and CSCD686480 (2-[(2-hydroxyethoxy)methyl]-6-
(trifluoromethyl)-3-pyridinecarboxylic acid), calculated as the 
stoichiometric equivalent of bicyclopyrone, in or on the commodities.

------------------------------------------------------------------------
                                                               Parts per
                          Commodity                              million
------------------------------------------------------------------------
Corn, field, forage..........................................       0.30
Corn, field, grain...........................................       0.02
Corn, field, stover..........................................       0.40
Corn, pop, grain.............................................       0.02
Corn, pop, stover............................................       0.40
Corn, sweet, forage..........................................       0.40
Corn, sweet, kernel plus cob with husks removed..............       0.03
Corn, sweet, stover..........................................       0.70
Sugarcane, cane \1\..........................................       0.02
Cattle, meat byproducts......................................       1.5
Goat, meat byproducts........................................       1.5
Sheep, meat byproducts.......................................       1.5
Horse, meat byproducts.......................................       1.5
Hog, meat byproducts.........................................       0.15
------------------------------------------------------------------------
\1\ There are no U.S. Registrations on Sugarcane as of March 13, 2015.

    (2) [Reserved].
    (b) [Reserved].

[FR Doc. 2015-09482 Filed 4-22-15; 8:45 am]
 BILLING CODE 6560-50-P