[Federal Register Volume 76, Number 66 (Wednesday, April 6, 2011)]
[Rules and Regulations]
[Pages 18899-18906]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2011-7774]


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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2009-0636; FRL-8864-3]


Indaziflam; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes tolerances for residues of 
indaziflam in or on multiple commodities which are identified and 
discussed later in this document. Bayer CropScience LP requested these 
tolerances under the Federal Food, Drug, and Cosmetic Act (FFDCA).

DATES: This regulation is effective April 6, 2011. Objections and 
requests for hearings must be received on or before June 6, 2011, 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: EPA has established a docket for this action under docket 
identification (ID) number EPA-HQ-OPP-2009-0636. All documents in the 
docket are listed in the docket index available at http://www.regulations.gov. Although listed in the index, some information is 
not publicly available, e.g., Confidential Business Information (CBI) 
or other information whose disclosure is restricted by statute. Certain 
other material, such as copyrighted material, is not placed on the 
Internet and will be publicly available only in hard copy form. 
Publicly available docket materials are available in the electronic 
docket at http://www.regulations.gov, or, if only available in hard 
copy, at the OPP Regulatory Public Docket in Rm. S-4400, One Potomac 
Yard (South Bldg.), 2777 S. Crystal Dr., Arlington, VA. The Docket 
Facility is open from 8:30 a.m. to 4 p.m., Monday through Friday, 
excluding legal holidays. The Docket Facility telephone number is (703) 
305-5805.

FOR FURTHER INFORMATION CONTACT: Bethany Benbow, Registration Division 
(7505P), Office of Pesticide Programs, Environmental Protection Agency, 
1200 Pennsylvania Ave., NW., Washington, DC 20460-0001; telephone 
number: (703) 347-8072; e-mail address: <a href="/cdn-cgi/l/email-protection#17757279757860397572637f76796e5772677639707861"><span class="__cf_email__" data-cfemail="6103040f030e164f03041509000f18210411004f060e17">[email protected]</span></a>.

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. 
Potentially affected entities may include, but are not limited to those 
engaged in the following activities:

    <bullet> Crop production (NAICS code 111).

[[Page 18900]]

    <bullet> Animal production (NAICS code 112).
    <bullet> Food manufacturing (NAICS code 311).
    <bullet> Pesticide manufacturing (NAICS code 32532).

    This listing is not intended to be exhaustive, but rather to 
provide a guide for readers regarding entities likely to be affected by 
this action. Other types of entities not listed in this unit could also 
be affected. The North American Industrial Classification System 
(NAICS) codes have been provided to assist you and others in 
determining whether this action might apply to certain entities. If you 
have any questions regarding the applicability of this action to a 
particular entity, consult the person listed under FOR FURTHER 
INFORMATION CONTACT.

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 e-CFR site at http://www.gpoaccess.gov/ecfr.

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-2009-0636 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 6, 2011. 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 that does not contain any 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 a copy of 
your non-CBI objection or hearing request, identified by docket ID 
number EPA-HQ-OPP-2009-0636, by one of the following methods:
    <bullet> Federal eRulemaking Portal: http://www.regulations.gov. 
Follow the on-line instructions for submitting comments.
    <bullet> Mail: Office of Pesticide Programs (OPP) Regulatory Public 
Docket (7502P), Environmental Protection Agency, 1200 Pennsylvania 
Ave., NW., Washington, DC 20460-0001.
    <bullet> Delivery: OPP Regulatory Public Docket (7502P), 
Environmental Protection Agency, Rm. S-4400, One Potomac Yard (South 
Bldg.), 2777 S. Crystal Dr., Arlington, VA. Deliveries are only 
accepted during the Docket Facility's normal hours of operation (8:30 
a.m. to 4 p.m., Monday through Friday, excluding legal holidays). 
Special arrangements should be made for deliveries of boxed 
information. The Docket Facility telephone number is (703) 305-5805.

II. Summary of Petitioned-For Tolerance

    In the Federal Register of January 6, 2010 (75 FR 864) (FRL-8801-
5), EPA issued a notice pursuant to section 408(d)(3) of FFDCA, 21 
U.S.C. 346a(d)(3), announcing the filing of two pesticide petitions (PP 
9F7589 and PP 9E7588) by Bayer CropScience LP, 2 T.W. Alexander Dr., 
Research Triangle Park, NC 27709. The petition requested that 40 CFR 
part 180 be amended by adding a section for the herbicide indaziflam 
and establishing tolerances therein for residues of indaziflam, N-
[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-
1,3,5-triazine-2,4-diamine, in or on fruit, citrus, group 10; fruit, 
pome, group 11; fruit, stone, group 12; nut, tree, group 14; pistachio; 
grape; and olive; each at 0.01 parts per million (ppm) and almond, 
hulls at 0.20 ppm (PP 9F7589). Additionally, Bayer CropScience LP 
requested an import tolerance for sugarcane, sugar, refined at 0.01 ppm 
(PP 9E7588). That notice referenced a summary of the petitions prepared 
by Bayer CropScience LP, the registrant, which is available in the 
docket, http://www.regulations.gov. There were no comments received in 
response to the notice of filing.
    Based upon review of the data supporting the petitions, EPA has 
modified the petitioner's request by lowering the proposed tolerance 
level for almond, hulls from 0.20 ppm to 0.15 ppm. EPA is also revising 
the proposed commodity term, ``Sugarcane, sugar, refined'' to read 
``Sugarcane, refined sugar.'' Additionally, EPA is revising the citrus 
and pome fruit crop group names and the requested tolerance expression. 
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 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 section 408(b)(2)(D) of FFDCA, and the factors 
specified in section 408(b)(2)(D) of FFDCA, 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 indaziflam including 
exposure resulting from the tolerances established by this action. 
EPA's assessment of exposures and risks associated with indaziflam 
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 toxicology database for indaziflam is complete and adequate for 
selecting toxicity endpoints for risk assessment. The scientific 
quality of the data is relatively high, and the toxicity is well-
characterized for all types of effects, including potential 
developmental, reproductive, immunologic and neurologic toxicity.
    Indaziflam has low acute toxicity via the oral, dermal, and 
inhalation routes of exposure. It is not irritating to the eye or skin 
and is not a dermal sensitizer.
    The nervous system is a target for indaziflam in rats and dogs. In 
the dog degenerative neuropathology of the brain, spinal cord and 
sciatic nerve was reported in the dog following both subchronic and 
chronic oral exposure. Neuropathology in the dog was the most sensitive 
effect and was selected as the risk assessment endpoint for all

[[Page 18901]]

repeated exposure scenarios. In the rat, histopathology of the brain 
and pituitary pars nervosa was observed following chronic exposure. 
Clinical signs of neurotoxicity were observed in both species in 
several studies, including rat adult and developmental neurotoxicity 
studies. Decreased motor activity observed in the rat acute 
neurotoxicity study was selected as the appropriate endpoint for 
assessing acute oral exposures.
    In addition to the neurological system, chronic exposure was 
associated with degenerative renal effects in the rat and mouse, 
hypertrophy (considered adaptive), increased macrovacuolation and 
multinucleated hepatocytes in the rat liver, increased follicular cell 
hypertrophy and colloid alteration in the rat thyroid, degeneration in 
rat reproductive tissues including atrophied seminal vesicles (males), 
and in female mice, blood-filled ovarian cysts/follicles (females) and 
gastric lesions. Thyroid and gastric effects were also observed 
following subchronic exposure of the rat. Decreased body weight gains 
were generally observed in the available subchronic and chronic 
studies. No systemic toxicity was observed in a 28-day dermal toxicity 
study in the rat.
    Developmental effects in offspring were absent or limited to doses 
that also caused systemic toxicity in the adult. In the rat 
developmental toxicity study, decreased fetal weight was observed in 
the presence of maternal effects that included decreased body weight 
and clinical signs of toxicity. No developmental effects were observed 
in rabbits up to maternally toxic dose levels. Decreased pup weight and 
delays in sexual maturation (preputial separation in males and vaginal 
patency in females) were observed in the rat 2-generation reproductive 
toxicity study, along with clinical signs of toxicity, at a dose 
causing parental toxicity that included clinical signs and decreased 
weight gain. In the developmental neurotoxicity study, transiently 
decreased motor activity (PND 21 only) in male offspring was observed 
and was considered a potential neurotoxic effect. It was observed at a 
dose that also caused clinical signs of neurotoxicity along with 
decreased body weight in maternal animals.
    There was no evidence of carcinogenicity observed in the 2-year 
dietary rat or mouse carcinogenicity bioassays and no evidence of 
genotoxicity in mutagenicity studies (reverse gene mutation in 
bacteria, forward gene mutation in mammalian cells) or in vitro and in 
vivo chromosomal aberration assays. Based on the lack of evidence of 
carcinogenicity or genotoxicity, the Agency classified indaziflam as 
``not likely to be carcinogenic to humans.''
    Specific information on the studies received and the nature of the 
adverse effects caused by indaziflam, 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 document ``Indaziflam: Human health risk 
assessment for use in citrus, stone, and pome fruits; grapes; tree 
nuts; pistachios; olives; and sugar cane (imported refined sugar),'' p. 
41 in docket ID number EPA-HQ-OPP-2009-0636.

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 NOAEL are observed and the LOAEL which 
adverse effects of concern are identified. 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 indaziflam used for human 
risk assessment is shown in the table below of this unit.

   Table--Summary of Toxicological Doses and Endpoints for Indaziflam for Use in Human Health Risk Assessment
----------------------------------------------------------------------------------------------------------------
                                     Point of departure and
         Exposure/scenario             uncertainty/safety    RfD, PAD, LOC for risk    Study and toxicological
                                             factors               assessment                  effects
----------------------------------------------------------------------------------------------------------------
Acute dietary (General population    NOAEL = 50 mg/kg/day..  Acute RfD = 0.5 mg/kg/  Acute oral neurotoxicity in
 including females 13-49 years of    UFA = 10x.............   day.                    the rat. LOAEL = 100 mg/kg/
 age and infants and children).      UFH = 10x.............  aPAD = 0.5 mg/kg/day..   day based on decreased
                                     FQPA SF = 1x..........                           motor and locomotor
                                                                                      activity in females.
----------------------------------------------------------------------------------------------------------------
Chronic dietary (All populations)..  NOAEL = 2 mg/kg/day...  Chronic RfD = 0.02 mg/  Chronic oral (dietary)
                                     UFA = 10x.............   kg/day.                 toxicity in the dog. LOAEL
                                     UFH = 10x.............  cPAD = 0.02 mg/kg/day.   = \6/7\ mg/kg/day M/F,
                                     FQPA SF = 1x..........                           based on nerve fiber
                                                                                      degenerative lesions in
                                                                                      the brain, spinal cord and
                                                                                      sciatic nerve.
----------------------------------------------------------------------------------------------------------------
Incidental oral short-term (1 to 30  NOAEL= 7.5 mg/kg/day..  LOC for MOE = 100.....  Subchronic oral (gavage) in
 days) and intermediate-term (1 to   UFA = 10x.............                           the dog. LOAEL = 15 mg/kg/
 6 months).                          UFH = 10x.............                           day based on axonal
                                     FQPA SF = 1x..........                           degenerative microscopic
                                                                                      findings in the brain,
                                                                                      spinal cord and sciatic
                                                                                      nerve.
----------------------------------------------------------------------------------------------------------------

[[Page 18902]]

 
Dermal short-term..................  Dermal (or oral) study  LOC for MOE = 100.....  Subchronic oral (gavage) in
(1 to 30 days) and intermediate-      NOAEL = 7.5 mg/kg/day                           the dog. LOAEL = 15 mg/kg/
 term (1 to 6 months).                (dermal absorption                              day based on axonal
                                      rate = 7.3%).                                   degenerative microscopic
                                     UFA = 10x.............                           findings in the brain,
                                     UFH = 10x.............                           spinal cord and sciatic
                                     FQPA SF = 1x..........                           nerve.
----------------------------------------------------------------------------------------------------------------
Inhalation short-term (1 to 30       Inhalation (or oral)    LOC for MOE = 100.....  Subchronic oral (gavage) in
 days) and intermediate-term (1 to    study NOAEL= 7.5 mg/                            the dog. LOAEL = 15 mg/kg/
 6 months).\1\                        kg/day (inhalation                              day based on axonal
                                      absorption rate =                               degenerative microscopic
                                      100%).                                          findings in the brain,
                                     UFA = 10x.............                           spinal cord and sciatic
                                     UFH = 10x.............                           nerve.
                                     FQPA SF = 1x..........
----------------------------------------------------------------------------------------------------------------
Cancer (Oral, dermal, inhalation)..    Classification: ``Not Likely to be Carcinogenic to Humans'' based on the
                                        absence of significant tumor increases in the two-year dietary rat and
                                                                   mouse bioassays.
----------------------------------------------------------------------------------------------------------------
UFA = extrapolation from animal to human (interspecies). UFH = potential variation in sensitivity among members
  of the human population (intraspecies). FQPA SF = Food Quality Protection Act Safety Factor. PAD = population
  adjusted dose (a = acute, c = chronic). RfD = reference dose. MOE = margin of exposure. LOC = level of
  concern.
\1\ EPA selected a point of departure from an oral study to assess short-term residential handler inhalation
  risks for indaziflam. While it is possible that extrapolation of an inhalation endpoint from an oral study may
  sometimes underestimate inhalation risk, in this case the Agency believes the risk assessment is protective of
  adult handlers. MOEs calculated for residential handlers ranged from 3,000 to 510,000, thus providing an ample
  margin of safety to account for any uncertainties in route-to-route extrapolation. Further, the contribution
  of residential inhalation exposure to aggregate risk is small.

C. Exposure Assessment

    1. Dietary exposure from food and feed uses. In evaluating dietary 
exposure to indaziflam, EPA considered exposure under the petitioned-
for tolerances. There are no tolerances currently established for 
indaziflam. EPA assessed dietary exposures from indaziflam 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 indaziflam. In estimating acute 
dietary exposure, EPA used food consumption information from the United 
States Department of Agriculture (USDA) 1994-1996 and 1998 Nationwide 
Continuing Surveys of Food Intake by Individuals (CSFII). As to residue 
levels in food, EPA assumed that residues are present in all 
commodities at the tolerance level and that 100% of commodities are 
treated with indaziflam. DEEM-FCID, Version 2.03 default concentration 
factors were used to estimate residues of indaziflam in processed 
commodities with the exception of the empirically derived raisin 
processing factor of 2.8x.
    ii. Chronic exposure. In conducting the chronic dietary exposure 
assessment EPA used the food consumption data from the USDA 1994-1996 
and 1998 CSFII. As to residue levels in food, EPA assumed that residues 
are present in all commodities at the tolerance level and that 100% of 
commodities are treated with indaziflam. DEEM-FCID, Version 2.03 
default concentration factors were used to estimate residues of 
indaziflam in processed commodities with the exception of the 
empirically derived raisin processing factor of 2.8x.
    iii. Cancer. Based on the results of carcinogenicity studies in 
rats and mice, EPA classified indaziflam as ``Not Likely to be 
Carcinogenic to Humans'' therefore, a dietary exposure assessment for 
the purpose of assessing cancer risk is unnecessary.
    iv. Anticipated residue and percent crop treated (PCT) information. 
EPA did not use anticipated residue or PCT information in the dietary 
assessment for indaziflam. Tolerance level residues and 100 PCT were 
assumed for all food commodities.
    2. Dietary exposure from drinking water. The residues of concern in 
drinking water include indaziflam and its degradates: Triazine 
indanone, indaziflam-carboxylic acid, indaziflam-olefin, indaziflam-
hydroxyethyl, fluoroethyl-diaminotriazine (FDAT), and 
dihydroaminotriazine (a degradate of FDAT). The Agency used screening 
level water exposure models in the dietary exposure analysis and risk 
assessment for indaziflam and its degradates in drinking water. These 
simulation models take into account data on the physical, chemical, and 
fate/transport characteristics of indaziflam and its degradates. 
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 
indaziflam and its degradates for acute exposures are estimated to be 
84 parts per billion (ppb) for surface water and 3.7 ppb for ground 
water. The chronic exposures for non-cancer assessments are estimated 
to be 26 ppb for surface water and 3.7 ppb for ground water.
    Modeled estimates of drinking water concentrations were directly 
entered into the dietary exposure model. For acute dietary risk 
assessment, the water concentration value of 84 ppb was used to assess 
the contribution to drinking water. For chronic dietary risk 
assessment, the water concentration of value 26 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). Indaziflam

[[Page 18903]]

is currently registered for the following uses that could result in 
residential exposures: Residential turfgrass and recreational areas. 
EPA assessed residential exposure using the following assumptions: 
There is a potential for short-term exposure of homeowners applying 
products containing indaziflam on home lawns. There is also a potential 
for short- and intermediate-term post-application exposure of adults 
and children entering lawn and recreation areas, including golf 
courses, which have been treated with indaziflam. Indaziflam post-
application inhalation exposures are expected to be negligible due to 
its low vapor pressure, low application rates, and the types of 
application equipment used (i.e., hand-held equipment that is not 
likely to generate a vapor). Therefore, a quantitative post-application 
inhalation exposure assessment was not considered necessary. EPA 
assessed the following residential exposure scenarios:
    i. Short-term dermal and inhalation exposures of residential 
handlers using various types of application equipment and formulation 
types on the proposed residential use sites;
    ii. Short-term post-application dermal exposures of adults and 
children entering treated turf areas; and
    iii. Short-term postapplication incidental oral exposures of 
children from contact with treated turfgrass.
    Since the doses and endpoints selected to assess short- and 
intermediate-term exposures are the same, a separate quantitative 
intermediate-term assessment was not completed; the short-term risk 
assessments are protective of intermediate-term risks.
    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.''
    EPA has not found indaziflam to share a common mechanism of 
toxicity with any other substances. Indaziflam and its metabolite 
fluoroethyldiaminotriazine (FDAT) contain a triazine moiety within 
their chemical structures. Several triazine herbicides were determined 
by EPA to have a common mechanism of toxicity based on their ability to 
disrupt the hypothalamic-pituitary-gonadal axis (U.S. EPA, 2002). The 
triazine common mechanism group (TCMG) includes atrazine, simazine, 
propazine, and the metabolites desethyl-s-atrazine (DEA), deisopropyl-
s-atrazine (DIA), and diaminochlorotriazine (DACT). Indaziflam and its 
metabolite FDAT were considered for incorporation into the TCMG by EPA 
based on structure; indaziflam, FDAT, and the TCMG members contain a 
common triazine moiety. However, EPA determined that it would not be 
appropriate to include indaziflam and FDAT in the TCMG for the 
following reasons:
    i. The structure of indaziflam and FDAT are unique in that they 
contain a fluoroethyl group at the 2-position of the triazine ring, 
whereas the TCMG members contain a chlorine substituent at the 2-
position of the triazine ring and;
    ii. Indaziflam and FDAT do not elicit the same toxicological 
responses shared by the TCMG members. The TCMG members cause an 
increase in mammary gland tumors in rats and multiple developmental 
effects such as attenuation of the luteinizing hormone surge, altered 
pregnancy outcome, and delayed preputial separation. Although delayed 
sexual maturation was observed in the rat reproductive toxicity study, 
the effects occurred only at the highest dose. None of the other 
effects associated with the TCMG members were observed in the 
carcinogenicity, developmental, or reproductive guideline studies for 
indaziflam. In a non-guideline study, FDAT delayed vaginal patency in a 
dose-dependent manner. However, none of the other characteristic 
developmental effects of the TCMG members were observed, and this 
effect only occurred at higher doses compared to DACT. Therefore, 
unlike other pesticides for which EPA has followed a cumulative risk 
approach based on a common mechanism of toxicity, EPA found that 
neither indaziflam nor its metabolite FDAT have a common mechanism of 
toxicity with any other substances, and indaziflam does not appear to 
produce a toxic metabolite produced by other substances. For the 
purposes of this tolerance action, therefore, EPA has assumed that 
indaziflam does not have a common mechanism of toxicity with other 
substances. For information regarding EPA's efforts to determine which 
chemicals have a common mechanism of toxicity and to evaluate the 
cumulative effects of such chemicals, see EPA's Web site at http://www.epa.gov/pesticides/cumulative.

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 pre- and post-natal 
toxicity database for indaziflam includes guideline rat and rabbit 
developmental toxicity studies, a 2-generation reproduction toxicity 
study in rats and a developmental neurotoxicity study in rats. As 
discussed in Unit III.A., there was no evidence of increased pre- or 
post-natal susceptibility of fetuses or offspring in any of these 
studies.
    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 1x. That decision is based on the following 
findings:
    i. The toxicity database for indaziflam is considered complete and 
includes acceptable developmental toxicity studies in rats and rabbits, 
a 2-generation reproductive toxicity study in rats, a developmental 
neurotoxicity in rats, acute and subchronic neurotoxicity screening 
studies in rats, and an immunotoxicity study.
    ii. There is no evidence that indaziflam results in increased pre- 
or post-natal susceptibility of rats or rabbits in the prenatal 
developmental studies of rats in the 2-generation reproduction study, 
or of rats in the developmental neurotoxicity study.
    iii. There are no significant residual uncertainties in the 
exposure databases. The final report on the stability of indaziflam in 
frozen storage and processing data for citrus oil were only recently 
submitted by the petitioner and are currently undergoing full review at 
the Agency; however, based on a preliminary screening of the data, EPA 
does not expect these studies to have a measurable impact on exposure 
estimates for indaziflam.
    a. Storage stability. Preliminary information from the study 
indicates that indaziflam is stable in frozen

[[Page 18904]]

storage over a 25-26 month period, well beyond the 17-month period that 
samples from the residue field trials were stored frozen prior to 
analysis.
    b. Citrus oil processing data. Although all citrus commodities from 
submitted field trials and a processing study have total residues below 
the method limit of quantitation (LOQ) at a 5x exaggerated application 
rate, data were required for the processed commodity citrus oil due to 
the extremely high theoretical concentration factor (1000x). Citrus oil 
was not analyzed during the originally submitted processing study. Data 
from the recently submitted study indicate that indaziflam residues 
concentrate in citrus oil at approximately 11.7x compared to those in 
citrus raw agricultural commodities (RACs). Based on this preliminary 
concentration factor, the total residues in citrus oil are still 
estimated to be less than the LOQ. Therefore, EPA believes that the 
tolerance of 0.01 ppm (the LOQ) for citrus fruit is adequate to cover 
residues in citrus oil, as no finite residues would be expected in 
citrus oil even at exaggerated rates.
    The dietary food exposure assessments were performed assuming 
tolerance-level residues and 100 PCT for all commodities. EPA made 
conservative (protective) assumptions in the ground and surface water 
modeling used to assess exposure to indaziflam in drinking water. EPA 
used similarly conservative assumptions to assess post-application 
exposure of children including incidental oral exposure of toddlers. 
These assessments will not underestimate the exposure and risks posed 
by indaziflam.

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. An acute aggregate risk assessment takes into 
account acute exposure estimates from dietary consumption of food and 
drinking water. Using the exposure assumptions discussed in this unit 
for acute exposure, the acute dietary exposure from food and water to 
indaziflam will occupy 3% of the aPAD for infants, less than 1 year 
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 
indaziflam from food and water will utilize 10% of the cPAD for 
infants, less than 1 year 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 
indaziflam 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). Indaziflam 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 indaziflam.
    Using the exposure assumptions described in this unit for short-
term exposures, EPA has concluded the combined short-term food, water, 
and residential exposures result in aggregate MOEs of 2,400 for adults 
and 1,300 for children. For adults, EPA aggregated short-term 
residential handler inhalation and dermal exposure with chronic dietary 
exposure from food and water. For children, EPA aggregated short-term 
dermal and incidental oral residential exposures plus chronic dietary 
exposure from food and water. Because EPA's level of concern for 
indaziflam is for MOEs below 100, 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). Since the doses and endpoints selected to assess short- and 
intermediate-term exposures to indaziflam are the same, a separate 
quantitative intermediate-term assessment was not completed; the short-
term risk assessments are protective of both short- and intermediate-
term risks.
    5. Aggregate cancer risk for U.S. population. Based on the lack of 
evidence of carcinogenicity in two adequate rodent carcinogenicity 
studies, indaziflam is not expected to pose a cancer risk to humans.
    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 indaziflam residues.

IV. Other Considerations

A. Analytical Enforcement Methodology

    Adequate enforcement methodology (liquid chromatography/mass 
spectrometry/mass spectrometry (LC/MS/MS) Method DH-003-P07-02) is 
available to enforce the tolerance expression. The method is able to 
determine, separately, residues of indaziflam and FDAT. 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; e-mail address: <a href="/cdn-cgi/l/email-protection#562433253f3223333b33223e3932251633263778313920"><span class="__cf_email__" data-cfemail="abd9ced8c2cfdecec6cedfc3c4cfd8ebcedbca85ccc4dd">[email protected]</span></a>.

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 U.N. 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 an MRL for indaziflam.

C. Revisions to Petitioned-For Tolerances

    EPA is lowering the almond, hulls tolerance proposed at 0.20 ppm to 
0.15 ppm based on analysis of the field trial data using the Agency's 
NAFTA-harmonized tolerance/MRL calculator in accordance with the 
Guidance for Setting Pesticide Tolerances Based on Field Trial Data. 
EPA is also revising the proposed commodity term, ``Sugarcane, sugar, 
refined'' to read ``Sugarcane, refined sugar'' to agree with the 
Agency's Food and Feed Vocabulary. Additionally, EPA is revising the 
requested tolerance expression to clarify the chemical moieties that 
are covered by the tolerances and specify how compliance with the 
tolerances is to be measured. The revised tolerance expression makes 
clear that the

[[Page 18905]]

tolerances cover residues of the herbicide indaziflam, including its 
metabolites and degradates, but that compliance with the tolerance 
levels is to be determined by measuring only indaziflam, N-[(1R,2S)-
2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-
triazine-2,4-diamine, in or on the commodities.
    EPA was petitioned for tolerances on citrus fruit group 10 and pome 
fruit group 11. In the Federal Register of December 8, 2010 (75 FR 
76284) (FRL-8853-8), EPA issued a final rule that revised the crop 
grouping regulations. As part of this action, EPA expanded and revised 
the existing citrus fruit group 10 and pome fruit group 11. Changes to 
crop group 10 included adding the specialty commodities Australian 
desert lime, Australian finger lime, Australian round lime, Brown River 
finger lime, Japanese summer grapefruit, Mediterranean mandarin, Mount 
White lime, New Guinea wild lime, Russell River lime, sweet lime, 
Tachibana orange, Tahiti lime, tangelo, tangor, trifoliate orange, and 
uniq fruit; creating subgroups; revising the representative 
commodities; and naming the new crop group citrus fruit group 10-10. 
Changes to crop group 11 included adding the specialty commodities 
azarole, medlar, Asian pear, Chinese quince, Japanese quince, and 
tejocote; creating subgroups; revising the representative commodities; 
and naming the new crop group pome fruit group 11-10. EPA indicated in 
the December 8, 2010 final rule as well as the earlier January 6, 2010 
proposed rule (75 FR 807) (FRL-8801-2) that, for existing petitions for 
which a Notice of Filing had been published, the Agency would attempt 
to conform these petitions to the rule. Therefore, consistent with this 
rule, EPA has assessed exposure to the herbicide, indaziflam, assuming 
use under the revised crop groups. Because revising the requested crop 
groups to the updated crop groups did not result in a risk of concern, 
EPA is proposing to establish tolerances for indaziflam residues on 
citrus fruit group 10-10 and pome fruit group 11-10.

 V. Conclusion

    Therefore, tolerances are established for residues of the herbicide 
indaziflam, including its metabolites and degradates, in or on fruit, 
citrus, group 10-10 at 0.01 ppm; fruit, pome, group 11-10 at 0.01 ppm; 
fruit, stone, group 12 at 0.01 ppm; nut, tree, group 14 at 0.01 ppm; 
pistachio at 0.01 ppm; almond, hulls at 0.15 ppm; grape at 0.01 ppm; 
olive at 0.01 ppm; and sugarcane, refined sugar at 0.01 ppm. Compliance 
with the tolerance levels is to be determined by measuring only 
indaziflam, N-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-
fluoroethyl)-1,3,5-triazine-2,4-diamine, in or on the commodities.

VI. Statutory and Executive Order Reviews

    This final rule establishes tolerances under section 408(d) of 
FFDCA 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 section 408(d) of FFDCA, 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 section 408(n)(4) of FFDCA. 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) (Pub. L. 104-4).
    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), Public Law 104-113, section 12(d) (15 U.S.C. 272 
note).

VII. Congressional Review Act

    The Congressional Review Act, 5 U.S.C. 801 et seq., generally 
provides that before a rule may take effect, the agency promulgating 
the rule must submit a rule report to each House of the Congress and to 
the Comptroller General of the United States. 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 this final rule in the Federal 
Register. This final rule 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: March 23, 2011.
Steven Bradbury,
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. Section 180.653 is added to read as follows:


Sec.  180.653  Indaziflam; tolerances for residues:

    (a) General. Tolerances are established for residues of the 
herbicide indaziflam, N-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-
yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine, including its 
metabolites and degradates, in or on the commodities in the following 
table. Compliance with the tolerance levels specified in the table 
below is to be determined by

[[Page 18906]]

measuring only indaziflam, in or on the commodity.

------------------------------------------------------------------------
                                                              Parts per
                         Commodity                             million
------------------------------------------------------------------------
Almond, hulls..............................................         0.15
Fruit, citrus, group 10-10.................................         0.01
Fruit, pome, group 11-10...................................         0.01
Fruit, stone, group 12.....................................         0.01
Grape......................................................         0.01
Nut, tree, group 14........................................         0.01
Olive......................................................         0.01
Pistachio..................................................         0.01
Sugarcane, refined sugar \1\...............................         0.01
------------------------------------------------------------------------
\1\ Tolerance without a corresponding U.S. registration.

    (b) Section 18 emergency exemptions. [Reserved]
    (c) Tolerances with regional registrations. [Reserved]
    (d) Indirect or inadvertent residues. [Reserved]

[FR Doc. 2011-7774 Filed 4-5-11; 8:45 am]
BILLING CODE 6560-50-P


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