[Federal Register Volume 78, Number 221 (Friday, November 15, 2013)]
[Rules and Regulations]
[Pages 68741-68748]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2013-27147]


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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2012-0427; FRL-9392-1]


Tebuconazole; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes tolerances for residues of 
tebuconazole in or on the fruiting vegetable group 8-10 and amends the 
existing tolerances for barley grain and the cucurbit vegetable group 
9. Interregional Research Project Number 4 (IR-4) requested this 
tolerance and amendment under the Federal Food, Drug, and Cosmetic Act 
(FFDCA).

DATES: This regulation is effective November 15, 2013. Objections and 
requests for hearings must be received on or before January 14, 2014, 
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-2012-0427, 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), EPA West 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: Lois Rossi, Registration Division 
(7505P), Office of Pesticide Programs, Environmental Protection Agency, 
1200 Pennsylvania Ave. NW., Washington, DC 20460-0001; telephone 
number: (703) 305-7090; email address: [email protected].

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 
Printing Office's eCFR 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-2012-0427 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 
January 14, 2014. 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-2012-0427, 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.htm. 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 August 22, 2012 (77 FR 50661) (FRL-9358-
9), 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 
2E8012) by Interregional Research Project Number 4 (IR-4), 500 College 
Road East, Suite 201W., Princeton, NJ 08540. The petition requested 
that 40 CFR 180.474 be amended by establishing tolerances for residues 
of the fungicide tebuconazole, alpha-[2-(4-chlorophenyl)ethyl]-alpha-
(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol, including its 
metabolites and degradates, in or on barley, grain at 0.3 parts per 
million (ppm); vegetable, cucurbit group 9 at 0.4 ppm; and vegetable, 
fruiting group 8-10 at 1.3 ppm. The petition also requested the removal 
of the established tolerance, in or on vegetable, fruiting, group 8 at 
1.3 ppm once the proposed tolerance for vegetable, fruiting group 8-10 
at 1.3 ppm, has been established since the proposed new tolerance will 
supersede the existing tolerance. That document referenced a summary of 
the petition prepared by Bayer CropScience, the registrant, which is 
available in the docket, http://www.regulations.gov. There were no 
comments received in response to the notice of filing.

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

[[Page 68742]]

reliable information.'' This includes 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 tebuconazole including exposure 
resulting from the tolerances established by this action. EPA's 
assessment of exposures and risks associated with tebuconazole 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.
    Tebuconazole has low acute toxicity by the oral and dermal routes 
of exposure and moderate toxicity by the inhalation route. It is not a 
dermal sensitizer nor a dermal irritant; however, it is slightly to 
mildly irritating to the eye. The primary target organs of tebuconazole 
toxicity are the liver, the adrenals, the hematopoietic system, and the 
nervous system. Effects on these target organs were seen in both rodent 
and non-rodent species. In addition, ocular lesions were seen in dogs 
(including lenticular degeneration and increased cataract formation) 
following subchronic or chronic exposure.
    Oral administration of tebuconazole caused developmental toxicity 
in all species evaluated (rat, rabbit and mouse), with the most 
prominent effects in the nervous system. The developmental toxicity 
studies, including the developmental neurotoxicity study, demonstrated 
an increase in susceptibility in developing fetuses both quantitatively 
and qualitatively.
    Tebuconazole was classified as a Group C possible human carcinogen, 
based on an increase in the incidence of hepatocellular adenomas, 
carcinomas, and combined adenomas/carcinomas in male and female mice. 
This classification is generally used for chemicals with limited 
evidence of carcinogenicity in animals in the absence of human data. 
EPA has determined that quantification of risk using a non-linear 
approach, i.e., reference dose (RfD), for tebuconazole will adequately 
account for all chronic toxicity, including carcinogenicity, that could 
result from exposure to tebuconazole. That conclusion is based on the 
following considerations: (1) No carcinogenic response was seen in 
either sex in an acceptable rat cancer study; (2) the tumors found in 
the mouse are commonly seen in the mouse; (3) both tumors types were 
found only at the high dose, which was considered to be excessive for 
carcinogenicity testing based on the non-neoplastic findings; and (4) 
tebuconazole is not mutagenic.
    Specific information on the studies received and the nature of the 
adverse effects caused by tebuconazole as well as the no-observed-
adverse-effect-level (NOAEL) and the lowest-observed-adverse-effect-
level (LOAEL) from the toxicity studies can be found at http://www.regulations.gov in docket ID number EPA-HQ-OPP-2012-0427 on pages 
33-36 of the document titled ``Tebuconazole: Human Health Risk 
Assessment for Tolerance Increases Based on Submission of Condition of 
Registration Requirements for Barley and Cantaloupe; and Crop Group 
Expansion for Fruiting Vegetable Crop Group 8-10.''

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 tebuconazole used for 
human risk assessment is shown in Table 1 of this unit.

 Table 1--Summary of Toxicological Doses and Endpoints for Tebuconazole for Use in Human Health Risk Assessment
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                                Point of departure
       Exposure/scenario         and  uncertainty/  RfD, PAD, LOC for       Study and toxicological effects
                                  safety factors     risk  assessment
----------------------------------------------------------------------------------------------------------------
Acute dietary (General          LOAEL = 8.8 mg/kg/  Acute RfD = 0.029  Developmental Neurotoxicity Study--Rat.
 population including infants    day.                mg/kg/day.         LOAEL = 8.8 mg/kg/day based on decreases
 and children).                 UFA = 10x.........  aPAD = 0.029 mg/    in body weights, absolute brain weights,
                                UFH = 10x.........   kg/day.            brain measurements and motor activity in
                                FQPA SF (UFL) = 3x                      offspring.
Chronic dietary (All            LOAEL = 8.8 mg/kg/  Chronic RfD =      Developmental Neurotoxicity Study--Rat.
 populations).                   day.                0.029 mg/kg/day.   LOAEL = 8.8 mg/kg/day based on decreases
                                UFA = 10x.........  cPAD = 0.029 mg/    in body weights, absolute brain weights,
                                UFH = 10x.........   kg/day.            brain measurements and motor activity in
                                FQPA SF (UFL) = 3x                      offspring.
Incidental oral short-term (1   LOAEL = 8.8 mg/kg/  LOC for MOE = 300  Developmental Neurotoxicity Study--Rat.
 to 30 days).                    day.                                   LOAEL = 8.8 mg/kg/day based on decreases
                                UFA = 10x.........                      in body weights, absolute brain weights,
                                UFH = 10x.........                      brain measurements and motor activity in
                                FQPA SF (UFL) = 3x                      offspring.

[[Page 68743]]

 
Dermal short-term (1 to 30      Oral study LOAEL =  LOC for MOE = 300  Developmental Neurotoxicity Study--Rat.
 days).                          8.8mg/kg/day                           LOAEL = 8.8 mg/kg/day based on decreases
                                 (dermal                                in body weights, absolute brain weights,
                                 absorption rate =                      brain measurements and motor activity in
                                 13%.                                   offspring.
                                UFA = 10x.........
                                UFH = 10x.........
                                FQPA SF (UFL ) =
                                 3x.
Inhalation short-term (1 to 30  Oral study LOAEL =  LOC for MOE = 300  Developmental Neurotoxicity Study--Rat.
 days).                          8.8 mg/kg/day.                         LOAEL = 8.8 mg/kg/day based on decreases
                                UFA = 10x.........                      in body weights, absolute brain weights,
                                UFH = 10x.........                      brain measurements and motor activity in
                                FQPA SF (UFL) = 3x                      offspring.
                               ---------------------------------------------------------------------------------
Cancer (Oral, dermal,           Classification: Group C- possible human carcinogen based on statistically
 inhalation).                    significant increase in the incidence of hepatocellular adenoma, carcinoma, and
                                 combined adenoma/carcinomas in both sexes of NMRI mice. The chronic risk
                                 assessment is considered to be protective of any cancer effects; therefore, a
                                 separate quantitative cancer risk assessment is not required.
----------------------------------------------------------------------------------------------------------------
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. NOAEL = no-observed-adverse-effect-
  level. PAD = population adjusted dose (a = acute, c = chronic). RfD = reference dose. UF = uncertainty factor.
  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 tebuconazole, EPA considered exposure under the petitioned-
for tolerances as well as all existing tebuconzole tolerances in 40 CFR 
180.474. EPA assessed dietary exposures from tebuconazole in food as 
follows:
    i. Acute exposure. Quantitative acute dietary exposure and risk 
assessments 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 tebuconazole. In estimating acute 
dietary exposure, EPA used food consumption information from the United 
States Department of Agriculture (USDA) 2003-2008 National Health and 
Nutrition Examination Survey, What We Eat in America, (NHANES/WWEIA). 
As to residue levels in food, a somewhat refined, acute probabilistic 
dietary exposure assessment was conducted for all existing food uses of 
tebuconazole. EPA assumed tolerance levels residues for some 
commodities and used field trial and USDA PDP data for others. EPA also 
assumed 100% crop treated levels for most commodities and used percent 
crop treated (PCT) data for other commodities as described in Unit 
III.C.1.iv. below.
    ii. Chronic exposure. In conducting the chronic dietary exposure 
assessment, EPA used the food consumption data from the 2003-2008 
NHANES/WWEIA. As to residue levels in food, a somewhat refined chronic 
dietary exposure assessment was conducted for all existing food uses of 
tebuconazole. EPA assumed tolerance levels residues for some 
commodities and used field trial and USDA PDP data for others. EPA also 
assumed 100% crop treated levels for most commodities and used PCT data 
for other commodities as described in Unit III.C.1.iv. below.
    iii. Cancer. The Agency determined that cancer dietary risk 
concerns due to long-term consumption of tebuconazole residues are 
adequately addressed by the chronic dietary exposure analysis using the 
reference dose; i.e., the chronic dietary risk assessment is considered 
to be protective of any cancer effects, and therefore, a separate 
cancer dietary exposure analysis was not performed.
    iv. Anticipated residue and PCT information. Section 408(b)(2)(E) 
of FFDCA authorizes EPA to use available data and information on the 
anticipated residue levels of pesticide residues in food and the actual 
levels of pesticide residues that have been measured in food. If EPA 
relies on such information, EPA must require pursuant to FFDCA section 
408(f)(1) that data be provided 5 years after the tolerance is 
established, modified, or left in effect, demonstrating that the levels 
in food are not above the levels anticipated. For the present action, 
EPA will issue such Data Call-Ins as are required by FFDCA section 
408(b)(2)(E) and authorized under FFDCA section 408(f)(1). Data will be 
required to be submitted no later than 5 years from the date of 
issuance of these tolerances.
    Section 408(b)(2)(F) of FFDCA states that the Agency may use data 
on the actual percent of food treated for assessing chronic dietary 
risk only if:
     Condition a: The data used are reliable and provide a 
valid basis to show what percentage of the food derived from such crop 
is likely to contain the pesticide residue.
     Condition b: The exposure estimate does not underestimate 
exposure for any significant subpopulation group.
     Condition c: Data are available on pesticide use and food 
consumption in a particular area, the exposure estimate does not 
understate exposure for the population in such area.
    In addition, the Agency must provide for periodic evaluation of any 
estimates used. To provide for the periodic evaluation of the estimate 
of PCT as required by FFDCA section 408(b)(2)(F), EPA may require 
registrants to submit data on PCT.
    For the acute assessment, the Agency estimated the PCT for existing 
uses as follows:
    Grapes: 25%; grape, raisin: 25%; nectarine: 25%; peach: 20%; 
peanuts: 45%.
    For the chronic assessment, the Agency estimated the PCT for 
existing uses as follows:
    Grapes: 15%; grape, raisin: 15%; nectarine: 20%; peach: 15%; 
peanuts: 35%.
    In most cases, EPA uses available data from United States 
Department of Agriculture/National Agricultural Statistics Service 
(USDA/NASS), proprietary market surveys, and the National Pesticide Use 
Database for the chemical/crop combination for the most

[[Page 68744]]

recent 6-7 years. EPA uses an average PCT for chronic dietary risk 
analysis. The average PCT figure for each existing use is derived by 
combining available public and private market survey data for that use, 
averaging across all observations, and rounding to the nearest 5%, 
except for those situations in which the average PCT is less than 1. In 
those cases, 1% is used as the average PCT and 2.5% is used as the 
maximum PCT. EPA uses a maximum PCT for acute dietary risk analysis. 
The maximum PCT figure is the highest observed maximum value reported 
within the recent 6 years of available public and private market survey 
data for the existing use and rounded up to the nearest multiple of 5%.
    The Agency also used 2006 PCT information for tebuconazole on the 
following uses for the acute dietary assessment (apples, 44%; apricots 
56%; cherries, (babyfood), 42%; cherries (all other food forms), 100%; 
corn, sweet, 22%; hops 64%; plum 26%; turnip 68%) and for the chronic 
dietary assessment (apples, 41%; apricots, 43%; cherries, (babyfood), 
37%; cherries (all other food forms), 66%; corn, sweet, 14%; hops, 64%; 
plum, 24%; turnip, 44%). For further explanation of EPA's process for 
developing these PCT estimates, see the 2011 final rule for 
tebuconazole tolerances (76 FR 54127) (August 31, 2011) and its 
supporting documents.
    Subsequently, EPA considered the maximum and average PCT estimates 
for tebuconazole from the most recent (2011) screening level usage 
analysis available. Based on that information, EPA concludes that its 
risk assessments do not underestimate the overall actual PCT for uses 
of tebuconazole or exposure from the use of tebuconazole.
    The Agency believes that the three conditions discussed in Unit 
III.C.1.iv. have been met. With respect to Condition a, PCT estimates 
are derived from Federal and private market survey data, which are 
reliable and have a valid basis. The Agency is reasonably certain that 
the percentage of the food treated is not likely to be an 
underestimation. As to Conditions b and c, regional consumption 
information and consumption information for significant subpopulations 
is taken into account through EPA's computer-based model for evaluating 
the exposure of significant subpopulations including several regional 
groups. Use of this consumption information in EPA's risk assessment 
process ensures that EPA's exposure estimate does not understate 
exposure for any significant subpopulation group and allows the Agency 
to be reasonably certain that no regional population is exposed to 
residue levels higher than those estimated by the Agency. Other than 
the data available through national food consumption surveys, EPA does 
not have available reliable information on the regional consumption of 
food to which tebuconazole may be applied in a particular area.
    2. Dietary exposure from drinking water. The Agency used screening 
level water exposure models in the dietary exposure analysis and risk 
assessment for tebuconazole in drinking water. These simulation models 
take into account data on the physical, chemical, and fate/transport 
characteristics of tebuconazole. 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.
    Based on the Pesticide Root Zone Model/Exposure Analysis Modeling 
System (PRZM/EXAMS) and Screening Concentration in Ground Water (SCI-
GROW) models, the estimated drinking water concentrations (EDWCs) of 
tebuconazole for acute exposures are estimated to be 96.6 parts per 
billion (ppb) for surface water and 1.56 ppb for ground water and for 
chronic exposures are estimated to be 59 ppb for surface water and 1.56 
ppb for ground water.
    Modeled estimates of drinking water concentrations were directly 
entered into the dietary exposure model. For the acute dietary risk 
assessment a distribution of 30-year daily surface water concentrations 
was estimated for the EDWCs of tebuconazole. For chronic dietary risk 
assessment, the water concentration of value 59 ppb was used to assess 
the contribution to drinking water.
    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).
    Tebuconazole is currently registered for the following uses that 
could result in residential exposures: Turf, flower gardens, trees, 
ornamentals, and pressure-treated wood. EPA assessed residential 
exposure using the following assumptions: For residential handlers, 
exposure is expected to be short-term. Intermediate-term exposures are 
not likely because of the intermittent nature of applications by 
homeowners. Dermal and inhalation exposures were combined since the 
same endpoint and point of departure (POD) is used for both routes of 
exposure. Residential dermal and incidental oral post-application 
exposure was assessed for adults and children golfing, working in 
gardens, and performing physical activities on pressure-treated wood 
after application of tebuconazole may receive exposure to tebuconazole 
residues. Post-application exposure is expected to be short-term in 
duration. Further information regarding EPA standard assumptions and 
generic inputs for residential exposures may be found at http://www.epa.gov/pesticides/trac/science/trac6a05.pdf.
    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.''
    Tebuconazole is a member of the triazole-containing class of 
pesticides, the conazoles. Although conazoles act similarly in plants 
by inhibiting ergosterol biosynthesis, there is not necessarily a 
relationship between their pesticidal activity and their mechanism of 
toxicity in mammals. Structural similarities do not constitute a common 
mechanism of toxicity. Evidence is needed to establish that the 
chemicals operate by the same, or essentially the same, sequence of 
major biochemical events. In conazoles, however, a variable pattern of 
toxicological responses is found; some are hepatotoxic and 
hepatocarcinogenic in mice. Some induce thyroid tumors in rats. Some 
induce developmental, reproductive, and neurological effects in 
rodents. Furthermore, the conazoles produce a diverse range of 
biochemical events, including altered cholesterol levels, stress 
responses, and altered DNA methylation. It is not clearly understood 
whether these biochemical events are directly connected to their 
toxicological outcomes. Thus, there is currently no conclusive data to 
indicate that conazoles share common mechanisms of toxicity and EPA is 
not following a cumulative risk approach based on a common mechanism of 
toxicity for the conazoles. For information regarding EPA's procedures 
for cumulating effects from substances found to have a common mechanism 
of toxicity, see EPA's Web site at http://www.epa.gov/pesticides/cumulative.
    Tebuconazole is a triazole-derived pesticide. This class of 
compounds can form the common metabolite 1,2,4-triazole and two 
triazole conjugates (triazolylalanine and triazolylacetic acid). To 
support existing tolerances and to establish new tolerances for

[[Page 68745]]

triazole-derivative pesticides, including tebuconazole, EPA conducted a 
human health risk assessment for exposure to 1,2,4-triazole, 
triazolylalanine, and triazolylacetic acid resulting from the use of 
all current and pending uses of any triazole-derived fungicide. The 
risk assessment is a highly conservative, screening-level evaluation in 
terms of hazards associated with common metabolites (e.g., use of a 
maximum combination of uncertainty factors) and potential dietary and 
non-dietary exposures (i.e., high end estimates of both dietary and 
non-dietary exposures). In addition, the Agency retained the additional 
10X FQPA safety factor for the protection of infants and children. The 
assessment includes evaluations of risks for various subgroups, 
including those comprised of infants and children. The Agency's 
complete risk assessment is found in the propiconazole reregistration 
docket at http://www.regulations.gov, docket ID number EPA-HQ-OPP-2005-
0497.
    An updated dietary exposure and risk analysis for the common 
triazole metabolites 1,2,4-triazole (T), triazolylalanine (TA), 
triazolylacetic acid (TAA), and triazolylpyruvic acid (TP) was 
conducted and completed in May 2013, in association with a registration 
request for several other triazole fungicides. That analysis concluded 
that risk estimates were below the Agency's level of concern for all 
population groups. After addition of tolerances associated with this 
action to the exposure analyses, the increased tolerances for 
tebuconazole in/on barley, grain and vegetables, cucurbits, group 9 
along with the crop group conversion covered by this action do not 
significantly http://www.regulations.gov by searching for the following 
titles and docket numbers: ``Common Triazole Metabolites: Updated 
Aggregate Human Health Risk Assessment to Address The New Section 3 
Registrations For Use of Prothioconazole on Bushberry Crop Subgroup 13-
07B, Low Growing Berry, Except Strawberry, Crop Subgroup 13-07H, and 
Cucurbit Vegetables Crop Group 9; Use of Flutriafol on Coffee; and 
Ipconazole on Crop Group 6'' (located in docket ID number EPA-HQ-OPP-
2012-0876); ``Common Triazole Metabolites: Updated Dietary (Food + 
Water) Exposure and Risk Assessment to Address the Revised Tolerance 
for Residues of Fenbuconazole in Peppers'' (docket ID number EPA-HQ-
OPP-2012-0520).

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. Prenatal and postnatal sensitivity. The toxicity database for 
tebuconazole includes prenatal developmental toxicity studies in three 
species (mouse, rat, and rabbit), a reproductive toxicity study in 
rats, acute and subchronic neurotoxicity studies in rats, and a 
developmental neurotoxicity study in rats. The data from prenatal 
developmental toxicity studies in mice and a developmental 
neurotoxicity study in rats indicated an increased quantitative and 
qualitative susceptibility following in utero exposure to tebuconazole. 
The NOAELs/LOAELs for developmental toxicity in these studies were 
found at dose levels less than those that induce maternal toxicity or 
in the presence of slight maternal toxicity. There was no indication of 
increased quantitative susceptibility in the rat and rabbit 
developmental toxicity studies, the NOAELs for developmental toxicity 
were comparable to or higher than the NOAELs for maternal toxicity. In 
all three species, however, there was indication of increased 
qualitative susceptibility. For most studies, minimal maternal toxicity 
was seen at the LOAEL (consisting of increases in hematological 
findings in mice, increased liver weights in rabbits and rats, and 
decreased body weight gain/food consumption in rats) and did not 
increase substantially in severity at higher doses. However, there was 
more concern for the developmental effects at each LOAEL, which 
included increases in runts, increased fetal loss, and malformations in 
mice; increased skeletal variations in rats; and increased fetal loss 
and frank malformations in rabbits. Additionally, more severe 
developmental effects (including frank malformations) were seen at 
higher doses in mice, rats and rabbits. In the developmental 
neurotoxicity study, maternal toxicity was seen only at the high dose 
(decreased body weights, body weight gains, and food consumption, 
prolonged gestation with mortality, and increased number of dead 
fetuses), while offspring toxicity (including decreases in body weight, 
brain weight, brain measurements and functional activities) was seen at 
all doses.
    Available data indicated greater sensitivity of the developing 
organism to exposure to tebuconazole, as demonstrated by increases in 
qualitative sensitivity in prenatal developmental toxicity studies in 
rats, mice, and rabbits, and by increases in both qualitative and 
quantitative sensitivity in the developmental neurotoxicity study in 
rats with tebuconazole. However, the degree of concern is low because 
the toxic endpoints in the prenatal developmental toxicity studies were 
well characterized with clear NOAELs established and the most sensitive 
endpoint, which is found in the developmental neurotoxicity study, has 
been used for overall risk assessments. Therefore, there are no 
residual uncertainties for prenatal and/or postnatal susceptibility.
    3. Conclusion. EPA has determined that reliable data show the 
safety of infants and children would be adequately protected if the 
FQPA SF were reduced to 3x. That decision is based on the following 
findings:
    i. The toxicity database for tebuconazole is considered complete. 
An immunotoxicity study in rats has been submitted to the Agency and 
the study is currently under review. With preliminary evaluation, 
tebuconazole tested up to 1,000 ppm (78.4 milligrams/kilogram/day (mg/
kg/day) produced no immunotoxicity under the conditions of this study.
    ii. Tebuconazole demonstrated neurotoxicity in the acute 
neurotoxicity study in rats; the LOAEL of 100 mg/kg/day was based on 
increased motor activity in male and female rats and decreased 
footsplay in female rats. Malformations indicative of nervous system 
development disruption were seen in developmental toxicity studies in 
mice, rats, and rabbits. Neurotoxicity was also seen in offspring in 
the developmental neurotoxicity study in rats. The LOAEL of 8.8 mg/kg/
day was based on decreases in body weights, decreases in absolute brain 
weights, changes in brain morphometric parameters, and decreases in 
motor activity. A NOAEL could not be established. However, the LOAEL 
(8.8 mg/kg/day) was employed as the point of departure in assessing the 
risk for all exposure scenarios, and the FQPA SF is retained as a 
UFL (i.e., use of a LOAEL to extrapolate a NOAEL). A 
Benchmark Dose (BMD) analysis of the datasets relevant to the adverse 
offspring effects

[[Page 68746]]

(decreased body weight and brain weight) seen at the LOAEL in the DNT 
study was conducted. All of the BMDLs (benchmark dose limit) modeled 
successfully on statistically significant effects are 1-2X lower than 
the LOAEL. The results also indicate that an extrapolated NOAEL is not 
likely to be 10X lower than the LOAEL and that use of an UFL 
of 3X would not underestimate risk. Therefore, the analysis supports 
reducing the UFL from 10X to 3X. Using an UFL of 
3X in risk assessment (8.8 mg/kg/day / 3x = 2.9 mg/kg/day) is further 
supported by other studies in the tebuconazole toxicity database: Those 
studies with the lowest NOAELs were a developmental toxicity study in 
mice at 3 mg/kg/day and a chronic toxicity study in dogs at 2.9 mg/kg/
day, with effects being seen at respective LOAELs of 10 and 4.5 mg/kg/
day.
    iii. Although there is qualitative evidence of increased 
susceptibility in the prenatal developmental studies in rats, the 
Agency did not identify any residual uncertainties after establishing 
toxicity endpoints and traditional UFs to be used in the risk 
assessment of tebuconazole. The degree of concern for residual 
uncertainties for prenatal and/or postnatal toxicity is low.
    iv. There are no residual uncertainties identified in the exposure 
databases. EPA utilized a tiered approach in estimating exposure to 
tebuconazole. While some refinements were incorporated into dietary and 
residential exposure calculations, EPA is confident that the aggregate 
risk from exposure to tebuconazole in food, water and residential 
pathways will not be underestimated. The acute and chronic dietary 
exposure assessments incorporated refined estimates of residues in food 
commodities from reliable field trial data reflecting maximum use 
conditions, recent monitoring data from USDA's Pesticide Data Program 
(PDP), and relevant market survey data on the percentage of crops 
treated. Estimated concentrations of tebuconazole in drinking water 
were incorporated into the chronic dietary analysis as the upper bound 
point estimate and into the probabilistic acute dietary analysis as a 
distribution. For the residential exposure pathway (ornamentals, golf 
course turf, and treated wood products), potential exposure resulting 
from tebuconazole outdoor uses in the residential setting was assessed 
using screening-level inputs that assumes an adult or child will come 
in contact with turf and other surfaces immediately after application.

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.
    1. Acute risk. Using the exposure assumptions discussed in this 
unit for acute exposure, the acute dietary exposure from food and water 
to tebuconazole will occupy 55% of the aPAD for children 12 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 
tebuconazole from food and water will utilize 14% of the cPAD for 
children 1-2 years old, the population group receiving the greatest 
exposure. Based on the explanation in Unit III.C.3., regarding 
residential use patterns, chronic residential exposure to residues of 
tebuconazole is not expected.
    3. Short-term risk. Short-term aggregate exposure takes into 
account short-term residential exposure plus chronic exposure to food 
and water (considered to be a background exposure level).
    Tebuconazole is currently registered for uses that could result in 
short-term residential exposure, and the Agency has determined that it 
is appropriate to aggregate chronic exposure through food and water 
with short-term residential exposures to tebuconazole.
    Using the exposure assumptions described in this unit for short-
term exposures, EPA has concluded the combined chronic food, water, and 
short-term residential exposures result in aggregate MOEs of 1,500 for 
adult handlers; 400 for children 11-16 years old (post-application); 
360 for children 6-11 years old (post-application); 310 for adults 
(post-application); and 330 for children 3-5 years old (post-
application). Because EPA's level of concern for tebuconazole is a MOE 
of 300 or below, these MOEs are not of concern.
    4. Intermediate-term risk. Intermediate-term aggregate exposure 
takes into account intermediate-term residential exposure plus chronic 
exposure to food and water (considered to be a background exposure 
level).
    An intermediate-term adverse effect was identified; however, 
tebuconazole 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 
tebuconazole.
    5. Aggregate cancer risk for U.S. population. Tebuconazole has been 
classified as a possible human carcinogen based on statistically 
significant increase in the incidence of hepatocellular adenoma, 
carcinoma, and combined adenoma/carcinomas in both sexes of NMRI mice. 
The Agency has determined that the chronic risk assessment is 
considered to be protective of any cancer effects; therefore, a 
separate quantitative cancer risk assessment is not required
    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 tebuconazole residues.

IV. Other Considerations

A. Analytical Enforcement Methodology

    Adequate enforcement methodology (Gas Chromatography/Nitrogen 
Phosphorus Detector (GC/NPD)) 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: 
[email protected].

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).

[[Page 68747]]

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.
    Codex MRLs have been established for residues of tebuconazole in or 
on barley grain at 2 ppm. The Codex MRLs are based on field trials 
conducted in Europe with a maximum of two foliar applications and a 
pre-harvest interval (PHI) of 28 days. The U.S. tolerance of 0.3 ppm 
for barley grain is based on field trials conducted in the U.S. and 
Canada on barley as a single application with a 30-day PHI. The U.S. 
use pattern has a total seasonal application rate 25% of that of 
Europe. This explains the large difference in the recommended U.S. 
tolerance and the Codex MRL, and thus, harmonization is not possible.
    Codex MRLs are established on cucumber (0.15 ppm), summer squash 
(0.2 ppm), and melons (except watermelon) (0.15 ppm), which are crops 
included in EPA crop group vegetable, cucurbit, group 9. The Codex MRLs 
are based on field trials conducted in Europe with a maximum of four 
foliar applications and a PHI of 3 days for cucumbers and squash and 7 
days for melon. The U.S. tolerance for vegetable, cucurbit, group 9 is 
based on field trials conducted in the U.S. on cucumber, summer squash, 
and melons where tebuconazole was applied three times with a 2-8 day 
PHI. A tolerance of 0.4 ppm is recommended for cucurbit vegetables 
using the OECD statistical calculation procedures. Harmonization cannot 
be achieved since Codex MRLs are established on individual crops rather 
than on crop groups and have lower MRLs.
    Codex MRLs are established for sweet peppers (1 ppm), and tomatoes 
(0.7 ppm), which are crops included in EPA's crop grouping of 
vegetable, fruiting, group 8-10. The Codex MRLs are based on field 
trials conducted in Europe with a maximum of three foliar applications 
and a PHI of 3-7 days. The U.S. tolerance (1.3 ppm) was based on field 
trials conducted in the U.S. on bell peppers, non-bell peppers, and 
tomatoes where tebuconazole was applied as six broadcast foliar 
applications with a 6-7 day PHI. Harmonization cannot be achieved since 
Codex MRLs are established on individual crops rather than on crop 
groups and have lower MRLs.

V. Conclusion

    Therefore, a tolerance is established for residues of tebuconazole, 
alpha-[2-(4-chlorophenyl)ethyl]-alpha-(1,1-dimethylethyl)-1H-1,2,4-
triazole-1-ethanol, including its metabolites and degradates, in or on 
the vegetable, fruiting group 8-10 at 1.3 ppm. The existing tolerance 
for barley, grain is modified from 0.15 ppm to 0.3 ppm; and the 
existing tolerance for vegetable, cucurbit group 9 is modified from 
0.09 ppm to 0.4 ppm. Also, due to the establishment of the crop group 
tolerance for the vegetable, fruiting, group 8-10, the existing 
tolerances on okra and the vegetable, fruiting, group 8 are removed as 
unnecessary.

VI. Statutory and Executive Order Reviews

    This final rule 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 final rule has 
been exempted from review under Executive Order 12866, this final rule 
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 final rule 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 final rule 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 final rule. In addition, 
this final rule does not impose any enforceable duty or contain any 
unfunded mandate as described under Title II of the Unfunded Mandates 
Reform Act of 1995 (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 of 1995 (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: October 30, 2013.
Lois Rossi,
Director, Registration Division, 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. In Sec.  180.474, the table in paragraph (a) is amended by:
0
a. Revising the entries for ``Barley, grain'', and ``Vegetable, 
cucurbit, group 9.''
0
b. Removing the entries for ``Okra'' and ``Vegetable, fruiting, group 
8.''

[[Page 68748]]

0
c. Adding alphabetically the commodity ``Vegetable, fruiting, group 8-
10.''
    The amendments read as follows:


Sec.  180.474  Tebuconazole; tolerances for residues.

    (a) * * *

------------------------------------------------------------------------
                                                              Parts per
                         Commodity                             million
------------------------------------------------------------------------
 
                                * * * * *
Barley, grain..............................................          0.3
 
                                * * * * *
Vegetable, cucurbit, group 9...............................          0.4
Vegetable, fruiting, group 8-10............................          1.3
 
                                * * * * *
------------------------------------------------------------------------

* * * * *
[FR Doc. 2013-27147 Filed 11-14-13; 8:45 am]
BILLING CODE 6560-50-P