Document ID: EPA-HQ-OPP-2007-0312-0003
Agency: epa
Document Type: Rule
Title: Triflumizole; Pesticide Tolerances
Posted Date: 2009-06-03T04:00Z

[Federal Register: June 3, 2009 (Volume 74, Number 105)]
[Rules and Regulations]               
[Page 26536-26543]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr03jn09-8]                         

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2007-0312; FRL-8414-6]

 
Triflumizole; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes tolerances for combined residues 
of triflumizole and its metabolites containing the 4-chloro-2-
trifluoromethylaniline (FA-1-1) moiety, calculated as the parent 
compound, in or on leafy greens subgroup 4A, except spinach; Brassica, 
head and stem, subgroup 5A; Brassica, leafy greens, subgroup 5B; 
cilantro leaves; Swiss chard; pineapple; papaya; black sapote; 
canistel; mamey sapote; mango; sapodilla; star apple; hops, dried 
cones; and turnip greens. Interregional Research Project Number 4 (IR-
4) requested these tolerances under the Federal Food, Drug, and 
Cosmetic Act (FFDCA). This regulation also deletes the following time-
limited tolerances, as permanent tolerances supersede them: Collards, 
kale and mustard greens, as residues on these commodities will be 
covered by the Brassica, leafy greens, subgroup 5B tolerance; broccoli, 
since residues will be covered by the Brassica, head and stem, subgroup 
5A tolerance; dandelion leaves and parsley leaves, since residues will 
be covered by the leafy greens subgroup 4A tolerance; Swiss chard and 
turnip greens, as the time-limited tolerances will be superseded by 
permanent tolerances; and coriander leaves, as the cilantro leaves 
tolerance supersedes it and is the preferred commodity definition.

DATES: This regulation is effective June 3, 2009. Objections and 
requests for hearings must be received on or before August 3, 2009, 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-2007-0312. 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: Laura Nollen, Registration Division 
(7505P), Office of Pesticide Programs, Environmental Protection Agency, 
1200 Pennsylvania Ave., NW., Washington, DC 20460-0001; telephone 
number: (703) 305-7390; e-mail address: nollen.laura@epa.gov.

SUPPLEMENTARY INFORMATION:

I. General Information

A. Does this Action Apply to Me?

    You may be potentially affected by this action if you are an 
agricultural producer, food manufacturer, or pesticide manufacturer. 
Potentially affected entities may include, but are not limited to those 
engaged in the following activities:
     Crop production (NAICS code 111).
     Animal production (NAICS code 112).
     Food manufacturing (NAICS code 311).
     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.

[[Page 26537]]

B. How Can I Access Electronic Copies of this Document?

    In addition to accessing electronically available documents at 
http://www.regulations.gov, you may access this Federal Register 
document electronically through the EPA Internet under the ``Federal 
Register'' listings at http://www.epa.gov/fedrgstr. You may also access 
a frequently updated electronic version of EPA's tolerance regulations 
at 40 CFR part 180 through the Government Printing Office's e-CFR cite 
at http://www.gpoaccess.gov/ecfr.

C. Can I File an Objection or Hearing Request?

    Under section 408(g) of FFDCA, 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-2007-0312 in the subject line on the first 
page of your submission. All requests must be in writing, and must be 
mailed or delivered to the Hearing Clerk as required by 40 CFR part 178 
on or before August 3, 2009.
    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 that is described in ADDRESSES. Information not marked 
confidential pursuant to 40 CFR part 2 may be disclosed publicly by EPA 
without prior notice. Submit this copy, identified by docket ID number 
EPA-HQ-OPP-2007-0312, by one of the following methods:
     Federal eRulemaking Portal: http://www.regulations.gov. 
Follow the on-line instructions for submitting comments.
     Mail: Office of Pesticide Programs (OPP) Regulatory Public 
Docket (7502P), Environmental Protection Agency, 1200 Pennsylvania 
Ave., NW., Washington, DC 20460-0001.
     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. Petitions for Tolerance

    In the Federal Register of June 27, 2007 (72 FR 35237) (FRL-8133-
4), EPA issued a notice pursuant to section 408(d)(3) of FFDCA, 21 
U.S.C. 346a(d)(3), announcing the filing of a pesticide petition (PP 
7E7183) by IR-4, Rutgers, The State University of New Jersey, 500 
College Road East, Suite 201 W, Princeton, NJ 08540. The petition 
requested that 40 CFR 180.476 be amended by establishing a tolerance 
for combined residues of the fungicide triflumizole, 1-(1-((4-chloro-2-
(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1 H-imidazole, and its 
metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, 
calculated as the parent compound, in or on Brassica, leafy greens, 
subgroup 5B at 20.0 parts per million (ppm). That notice referenced a 
summary of the petition prepared on behalf of IR-4 by Chemtura USA 
Corporation, the registrant, which is available to the public in the 
docket, http://www.regulations.gov. There were no comments received in 
response to the notice of filing.
    In the Federal Register of February 6, 2008 (73 FR 6964) (FRL-8350-
9), EPA issued a notice pursuant to section 408(d)(3) of FFDCA, 21 
U.S.C. 346a(d)(3), announcing the filing of pesticide petitions (PP 
7E7258 and 7E7286) by IR-4. The petition requested that 40 CFR 180.476 
be amended by establishing tolerances for combined residues of the 
fungicide triflumizole, and its metabolites containing the 4-chloro-2-
trifluoromethylaniline moiety, calculated as the parent compound, in or 
on food commodities for PP 7E7258: Leafy greens subgroup 4A, except 
spinach, at 35 ppm; cilantro, leaves at 35 ppm; Swiss chard at 18 ppm; 
pineapple at 4.0 ppm; papaya at 2.5 ppm; sapote, black at 2.5 ppm; 
canistel at 2.5 ppm; sapote, mamey at 2.5 ppm; mango at 2.5 ppm; 
sapodilla at 2.5 ppm; star apple at 2.5 ppm; and hop, dried cones at 
50.0 ppm; and for PP 7E7286: Brassica, head and stem, subgroup 5A at 
5.0 ppm. That notice referenced a summary of the petition prepared on 
behalf of IR-4 by Chemtura USA Corporation, the registrant, which is 
available to the public in the docket, http://www.regulations.gov. 
There were no comments received in response to this notice of filing.
    In the Federal Register of May 16, 2008 (73 FR 28461) (FRL-8361-6), 
EPA issued a notice pursuant to section 408(d)(3) of FFDCA, 21 U.S.C. 
346a(d)(3), announcing the amendment of pesticide petition (PP 7E7258) 
by IR-4. The petition requested that 40 CFR 180.476 be amended by 
additionally establishing a tolerance for combined residues of the 
fungicide triflumizole, and its metabolites containing the 4-chloro-2-
trifluoromethylaniline moiety, calculated as the parent compound, in or 
on the food commodity turnip, greens at 40 ppm. That notice referenced 
a summary of the petition prepared on behalf of IR-4 by Chemtura USA 
Corporation, the registrant, which is available to the public in the 
docket, http://www.regulations.gov. There were no comments received in 
response to this notice of filing.
    Based upon review of the data supporting these petitions, EPA has 
determined that some of the proposed tolerance levels should be 
increased and has also revised the tolerance expression. The reasons 
for these changes are explained in Unit IV.D.

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 the petitioned-for 
tolerances for combined residues of triflumizole, and its metabolites 
containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as 
the parent compound, on leafy greens subgroup 4A, except spinach at 35 
parts per million (ppm); Brassica, head and stem, subgroup 5A at 8.0 
ppm; Brassica, leafy greens, subgroup 5B at 40.0 ppm; cilantro

[[Page 26538]]

leaves at 35 ppm; Swiss chard at 18 ppm; pineapple at 4.0 ppm; papaya 
at 2.5 ppm; black sapote at 2.5 ppm; canistel at 2.5 ppm; mamey sapote 
at 2.5 ppm; mango at 2.5 ppm; sapodilla at 2.5 ppm; star apple at 2.5 
ppm; hop, dried cones at 50.0 ppm; and turnip greens at 40 ppm. EPA's 
assessment of exposures and risks associated with establishing 
tolerances 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.
    Triflumizole has low acute toxicity via the oral, dermal, and 
inhalation routes. It is a mild eye irritant and dermal sensitizer, but 
is not a dermal irritant. The primary target organ affected by 
triflumizole is the liver. Liver effects were seen in rat and mouse 
subchronic and chronic/carcinogenicity studies. Subchronic effects 
included increased absolute and relative liver weights, accumulation of 
fat droplets, and slight hepatocyte centrilobular swelling. With 
increased length of exposure, the types of microscopic lesions noted 
increased in number and severity. Chronic effects included hepatocyte 
fatty vacuolization; hepatocyte hypertrophy, focal inflammation, and 
necrosis; fatty degeneration; eosinophilic foci of hepatocyte 
alteration; hepatic nodules; bile duct hyperplasia; and hyaline 
degeneration/fibrosis of the bile duct. The dog was less sensitive to 
the effects of triflumizole. In the dog chronic study, effects included 
increased liver weights, increased serum alkaline phosphatase levels, 
and a macroscopic hepatic lobular pattern and granular texture. A very 
mild, macrocytic anemia was also noted and was most likely secondary to 
liver effects.
    A special microsomal enzyme induction study showed that 
triflumizole can induce hepatic microsomal enzymes when administered 
orally at high doses. Kidney weights were increased in the rat and 
mouse also, but the only pathology seen microscopically was in the rat 
chronic/carcinogenicity study in which cortical cysts were noted. Other 
organ effects were observed microscopically at the highest dose tested 
(HDT) in the chronic rat study, which mainly involved cystic or 
hyperplastic lesions in endocrine glands and/or lymph nodes. Body 
weight decrements were noted in the rat and/or mouse subchronic, 
chronic and carcinogenicity studies and the developmental and 
reproduction studies.
    Long-term dietary administration of triflumizole did not result in 
an overall treatment-related increase in incidence of tumor formation 
in rats or mice. Based upon the lack of evidence of carcinogenicity in 
rats and mice, EPA classified triflumizole as ``not likely to be 
carcinogenic to humans'' by all routes of exposure. Further, 
triflumizole did not show evidence of mutagenicity in in vitro or in 
vivo studies.
    Signs of neurotoxicity were seen in the acute oral toxicity studies 
in the rat and mouse and an acute inhalation study in the rat. 
Neurotoxic signs were also observed in the acute neurotoxicity study 
based on functional-observational-battery (FOB) findings (neuromuscular 
impairment) and decreased locomotor activity. By day 8 of the 
observation period treated males and females were comparable to the 
controls. Although there was a statistically significant increase in 
hindlimb splay of low-dose females, this effect does not appear to be 
of great toxicological significance, since no other FOB effects were 
observed in low-dose females. No evidence of neurotoxicity was seen in 
the rat subchronic oral toxicity study or the mouse subchronic oral 
toxicity and carcinogenicity studies.
    In oral rat developmental studies, fetal effects (decreased numbers 
of viable fetuses, increased dead or resorbed fetuses, increased 
numbers of late resorptions, decreased fetal body weight and increased 
incidences of cervical ribs) were seen at the same doses where less 
severe maternal effects were noted (decreases in body weight gain and 
food consumption and increases in placental, spleen and liver weights). 
Fetal effects in the rabbit developmental study (decreased 24-hour 
survival, increased fetal and litter incidences of lumbar ribs and 
decreased placental weights) were noted at the same dose as maternal 
toxic effects (decreased food consumption, and decreased placental 
weights). In a multi-generation study in rats, offspring effects 
included decreased pup weights, survival indices, and litter sizes in 
both F3 litters, reduced litter size in the F1a litter, increased 
total-litter mortality in the F3a litter, and developmental effects in 
the F1b and F2b progeny. Reproductive toxicity, manifested as increased 
gestation length, was increased at the high dose.
    Specific information on the studies received and the nature of the 
adverse effects caused by triflumizole 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 ``Triflumizole: Second Amended Human 
Health Risk Assessment for Proposed Uses on Leafy Greens (Subgroup 4A) 
Except Spinach, Head and Stem Brassica (Subgroup 5A), Cilantro, Swiss 
Chard, Pineapple, Papaya, Black Sapote, Canistel, Mamey Sapote, Mango, 
Sapodilla, Star Apple, and Hops'' pages 51-55 in docket ID number EPA-
HQ-OPP-2007-0312.

B. Toxicological Endpoints

    For hazards that have a threshold below which there is no 
appreciable risk, a toxicological point of departure (POD) is 
identified as the basis for derivation of reference values for risk 
assessment. The POD may be defined as the highest dose at which no 
adverse effects are observed (the NOAEL) in the toxicology study 
identified as appropriate for use in risk assessment. However, if a 
NOAEL cannot be determined, the lowest dose at which adverse effects of 
concern are identified (the LOAEL) or a Benchmark Dose (BMD) approach 
is sometimes used for risk assessment. Uncertainty/safety factors (UFs) 
are used in conjunction with the POD to take into account uncertainties 
inherent in the extrapolation from laboratory animal data to humans and 
in the variations in sensitivity among members of the human population 
as well as other unknowns. Safety is assessed for acute and chronic 
dietary risks by comparing aggregate food and water exposure to the 
pesticide to the acute population adjusted dose (aPAD) and chronic 
population adjusted dose (cPAD). The aPAD and cPAD are calculated by 
dividing the POD by all applicable UFs. Aggregate short-, intermediate-
, and chronic-term risks are evaluated by comparing food, water, and 
residential exposure to the POD to ensure that the margin of exposure 
(MOE) called for by the product of all applicable UFs is not exceeded. 
This latter value is referred to as the Level of Concern (LOC).
    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 
greater than that expected in a lifetime. For more information on the 
general principles EPA uses in risk characterization and a complete 
description of the risk assessment

[[Page 26539]]

process, see http://www.epa.gov/pesticides/factsheets/riskassess.htm.
    EPA identified an acute effect for the general population 
(neuromuscular impairment and decreased locomotor activity seen in the 
rat acute neurotoxicity study) and for females 13 to 49 years old 
(decreased numbers of viable fetuses, increased dead or resorbed 
fetuses, increased numbers of late resorptions, decreased fetal body 
weight, and increased incidence of cervical ribs in the rat 
developmental toxicity study that are presumed to occur after a single 
exposure). The aPAD for the general population has been established at 
0.25 milligrams/kilogram/day (mg/kg/day); whereas, the aPAD for females 
13 to 49 years old is lower (0.1 mg/kg/day) due to the more sensitive 
endpoint on which it is based.
    In previous risk assessments for triflumizole, the chronic 
reference dose (cRfD) for the general population was derived from the 
NOAEL of 1.5 mg/kg/day from the multi-generation rat reproduction 
study. However, the Registrant requested that the Agency consider 
historical control data in relation to the rat reproductive study. 
Based on evaluation of the historical control data it was determined 
that the NOAEL should be 3.5 mg/kg/day (previously classified as the 
LOAEL). The NOAEL of 3.5 mg/kg/day was based on decreased pup body 
weight, mortality, reduced litter size and increased incidence of 
hydroureter and space between the body wall and organs observed at 8.5 
mg/kg/day (NOAEL= 3.5 mg/kg/day). In addition, gestation length was 
increased in the dams of F1a, F2a, and F3a intervals at the LOAEL of 
8.5 mg/kg/day (NOAEL = 3.5 mg/kg/day).
    Based on a re-evaluation of the toxicity database, it was 
determined that the most suitable endpoint for the derivation of a cRfD 
was a LOAEL of 3.5 mg/kg/day (a NOAEL was not determined) identified in 
a chronic rat study and based on liver toxicity. The revised NOAEL of 
3.5 mg/kg/day in the rat reproduction study would not be protective of 
potential liver toxicity associated with triflumizole. It was 
determined that the LOAEL of 3.5 mg/kg/day from the Combined Chronic 
Toxicity/Carcinogenicity (based on liver effects) was protective with 
an additional safety factor.
    A summary of the toxicological endpoints for triflumizole used for 
human risk assessment can be found at http://www.regulations.gov in 
document ``Triflumizole: Second Amended Human Health Risk Assessment 
for Proposed Uses on Leafy Greens (Subgroup 4A) Except Spinach, Head 
and Stem Brassica (Subgroup 5A), Cilantro, Swiss Chard, Pineapple, 
Papaya, Black Sapote, Canistel, Mamey Sapote, Mango, Sapodilla, Star 
Apple, and Hops'' pages 30-32 in docket ID number EPA-HQ-OPP-2007-0312.

C. Exposure Assessment

    1. Dietary exposure from food and feed uses. In evaluating dietary 
exposure to triflumizole, EPA considered exposure under the petitioned-
for tolerances as well as all existing triflumizole tolerances in 40 
CFR 180.476. EPA assessed dietary exposures from triflumizole 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.
    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 
tolerance level residues and 100 percent crop treated (PCT) for all 
existing and new uses of triflumizole.
    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 used average field 
trial residues as anticipated residues (ARs) for apple, grape, pear, 
cherry, cucurbit, strawberry, leafy greens (subgroup 4A) except 
spinach, head and stem Brassica (subgroup 5A), cilantro, Swiss chard, 
pineapple, papaya, black sapote, canistel, mamey sapote, mango, 
sapodilla, star apple and hops. For all other commodities, the 
assessment used tolerance level residues. The EPA used PCT information 
for apples, cantaloupes, cherries, cucumbers, grapes, hazelnuts 
(filberts), honeydew melons, pears, pumpkins, squash, strawberries and 
watermelons. 100 PCT information was used for the remaining registered 
and proposed uses.
    iii. Cancer. Based on absence of significant tumor increases in two 
rodent carcinogenicity studies, EPA has classified triflumizole as 
``not likely to be carcinogenic to humans;'' therefore, a quantitative 
exposure assessment to evaluate cancer risk is unnecessary.
    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.
    The Agency used PCT information for chronic assessments as follows:
    Apples 20%; Cantaloupe 10%; Cherries 15%; Cucumbers 5%; Grapes 5%; 
Hazelnuts (Filberts) 15%; Honeydew melons 15%; Pears 40%; Pumpkin 5%; 
Squash 1%; Strawberry 15%; and Watermelon 5%.
    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 recent 6 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 one. 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

[[Page 26540]]

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 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 triflumizole 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 triflumizole in drinking water. These simulation models 
take into account data on the physical, chemical, and fate/transport 
characteristics of triflumizole. 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) for surface water and Screening Concentration in 
Ground Water (SCI-GROW) models for ground water, the estimated drinking 
water concentrations (EDWCs) of triflumizole and its metabolites 
containing the 4-chloro-2-trifluoromethyl aniline moiety for surface 
water are estimated to be 37.4 parts per billion (ppb) for acute 
exposures; 15.8 ppb for chronic exposures for non-cancer assessments. 
For ground water, the EDWCs for all of the above exposure scenarios are 
estimated to be 3.11 ppb.
    Modeled estimates of drinking water concentrations were directly 
entered into the dietary exposure model. For acute dietary risk 
assessment, the water concentration value of 37 ppb was used to assess 
the contribution to drinking water. For chronic dietary risk 
assessment, the water concentration of value 16 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).
    Triflumizole is currently registered for use on ornamental plants 
including trees, shrubs and vines in residential areas. Since 
residential applications of triflumizole are to be made by commercial 
applicators, residential handler exposures are not expected to occur. 
In addition, post-application exposures of adults and children from 
this use have been determined to be negligible. Therefore, a 
residential exposure assessment is not necessary for triflumizole and 
was not conducted.
    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 triflumizole to share a common mechanism of 
toxicity with any other substances, and triflumizole does not appear to 
produce a toxic metabolite produced by other substances. For the 
purposes of this tolerance action, therefore, EPA has assumed that 
triflumizole 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 website 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 prenatal and postnatal 
toxicity database for triflumizole includes prenatal developmental 
toxicity studies in rats and rabbits and a multi-generation 
reproduction toxicity study in rats. There is no evidence of increased 
quantitative or qualitative susceptibility of rabbit fetuses following 
in utero exposure to triflumizole. Although 24-hour fetal survival was 
reduced in this study, 24-hour fetal survival is more an indicator of 
fetal endurance after being removed from the womb rather than a 
measurement of treatment-related effects on fetal viability and, thus, 
is not appropriate to use to ascertain fetal susceptibility. In the 
multi-generation rat reproduction study, reproductive toxicity 
(increased gestation length and increased vaginal bleeding and 
dystocias) was increased at the high dose. However, these effects may 
be a result of endocrine effects on the reproductive system. Comparison 
of offspring toxicity to reproductive toxicity is more appropriate to 
evaluate susceptibility because the increased gestation length in the 
dams is a true parental effect and may affect the dam or the offspring; 
therefore, there is no increased susceptibility of offspring following 
prenatal and postnatal exposure in the rat reproduction study.
    There was evidence of increased qualitative susceptibility 
following in utero exposure of rats in a developmental study. 
Developmental toxicity resulted in decreased pup viability, increased 
dead or resorbed fetuses and an increased incidence of cervical ribs at 
doses that resulted in less severe maternal toxicity (decreases in body 
weight gain and food consumption and increases in placental, spleen and 
liver weights). There are no residual uncertainties for developmental 
toxicity, and the use of the developmental NOAEL and the endpoint for 
the acute reference dose (aRfD) for females 13-49 is considered 
protective of the prenatal toxicity following an acute dietary 
exposure.
    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 for all repeated exposure scenarios and 1X 
for single

[[Page 26541]]

exposure scenarios. That decision is based on the following findings.
    i. The toxicity database for triflumizole is complete except for 
immunotoxicity testing. Recent changes to 40 CFR part 158 make 
immunotoxicity testing (OPPTS Guideline 870.7800) required for 
pesticide registration; however, the existing data are sufficient for 
endpoint selection for exposure/risk assessment scenarios, and for 
evaluation of the requirements under the FQPA. In the toxicity database 
for triflumizole, there was some indication of possible immunotoxicity 
in the form of non-neoplastic lesions, characterized as dilated cyctic 
sinuses in the thymic lymph node following dietary administration for 2 
years. However, these lesions were seen only in male rats at the HDT 
and only at the termination of the study. This indicates that these 
lesions are non-specific, are due to the age of the rats, and thus are 
not attributable to frank immunotoxicity. There were no other 
corroborative changes, such as changes in the thymus weights, in this 
study or in the thymus and spleen in the other studies (i.e., 
subchronic and chronic studies in dogs). Moreover, triflumizole belongs 
to the imidazole class of compounds, which are not known to be 
immunotoxicants. Based on the considerations in this unit, the Agency 
does not believe that conducting the immunotoxicity study will result 
in a dose less than the point of departure already used in this risk 
assessment and an additional database uncertainty factor for potential 
immunotoxicity does not need to be applied.
    ii. There is no need for a developmental neurotoxicity (DNT) study 
or additional UFs to account for neurotoxicity based on the following 
considerations:
    Signs of neurotoxicity were observed in the acute neurotoxicity 
study based on FOB findings (neuromuscular impairment) and decreased 
locomotor activity. By day 8 of the observation period treated males 
and females were comparable to the controls. Although there was a 
statistically significant increase in hindlimb splay of low-dose 
females, this effect does not appear to be of great toxicological 
significance, as no other FOB effects were observed in low-dose 
females. In a combined subchronic oral toxicity/subchronic 
neurotoxicity study there was no evidence of neurotoxicity at any dose 
tested. Further, there were no signs of neurotoxicity and no 
indications of increased susceptibility of in utero rats or rabbits or 
offspring in the developmental and reproduction studies for 
triflumizole. There was evidence of qualitative toxicity in the rat 
developmental toxicity study, but only at doses that were maternally 
toxic. The evidence does not support the need for a developmental 
neurotoxicity study. This conclusion is supported by:
     No neurotoxic signs noted in the rat subchronic study at 
any dose;
     No neurotoxic signs in the adult or offspring in the 
developmental and reproduction studies; and
     No neurotoxicity noted in any developmental toxicity 
study.
    iii. There is no evidence that triflumizole results in increased 
susceptibility in in utero rats or rabbits in the prenatal 
developmental studies or in young rats in the 2-generation reproduction 
study. Although there is evidence of increased qualitative 
susceptibility in the prenatal developmental study in rats, the Agency 
did not identify any residual uncertainties after establishing toxicity 
endpoints, traditional UFs for single exposure scenarios, and an 
additional 3X SF for repeated exposures to triflumizole (to address 
concerns for the use of a LOAEL instead of a NOAEL to derive the cRfD.
    iv. The chronic POD is derived from the use of a LOAEL (based on 
liver toxicity; aseosinophilic foci in male rats and fatty vacuolation 
and inflammation and necrosis in female rats) established in the 
combined chronic toxicity/carcinogenicity study in rats. Although use 
of a LOAEL as a POD raises uncertainty, here the uncertainty is 
relatively low indicating that a 3X FQPA safety factor will be 
adequate. That conclusion is based on the following weight of evidence 
considerations:
     The most sensitive endpoint in the target organ (liver) 
for this class of compounds (imidazole fungicide) is used for assessing 
chronic risk;
     There is low concern for the observed effects since the 
lesions did not progress into malignancy;
     The response was marginal at the LOAEL;
     The available data do not show this chemical to be a 
potent toxicant, as clear NOAELs were established following dietary 
administrations in all other studies, such as the 2-generation 
reproduction study in rat (3.5 mg/kg/day); subchronic rat (15.3 mg/kg/
day) and mouse (33.1 mg/kg/day) studies; chronic dog study (10 mg/kg/
day); and mouse carcinogenicity (16.2 mg/kg/day) study; and
     The extrapolated NOAEL of 1.2 mg/kg/day is supported by a 
comparable NOAEL (2.5 mg/kg/day) used to derive the cRfD for a 
structurally-related chemical (Imazalil).
    Based on these weight-of-evidence considerations, EPA is confident 
that the 3X FQPA SF is adequate to address the concerns for the lack of 
a NOAEL in the rat combined chronic toxicity/carcinogenicity study and 
that the cRfD would not underestimate dietary risk from chronic 
exposure to triflumizole. Specific information regarding the additional 
FQPA safety factor for chronic exposure to triflumizole can be found at 
http://www.regulations.gov in document ``Triflumizole: A Short History 
of the Chronic Endpoint'' in docket ID number EPA-HQ-OPP-2007-0312.
    v. There are no residual uncertainties identified in the exposure 
databases. The acute dietary food exposure assessments were performed 
based on 100 PCT and tolerance-level residues. The chronic dietary food 
exposure assessment utilized tolerance-level residues or anticipated 
residues that are based on reliable field trial data. For several 
currently registered commodities, the chronic assessment also utilized 
PCT data that have a valid basis and are considered to be reliable. EPA 
made conservative (protective) assumptions in the ground and surface 
water modeling used to assess exposure to triflumizole in drinking 
water. At this time, residential exposure of infants and children is 
expected to be negligible from the use of triflumizole. These 
assessments will not underestimate the exposure and risks posed by 
triflumizole.

E. Aggregate Risks and Determination of Safety

    EPA determines whether acute and chronic pesticide exposures are 
safe by comparing aggregate exposure estimates to the aPAD and cPAD. 
The aPAD and cPAD represent the highest safe exposures, taking into 
account all appropriate SFs. EPA calculates the aPAD and cPAD by 
dividing the POD by all applicable UFs. For linear cancer risks, EPA 
calculates the probability of additional cancer cases given the 
estimated aggregate exposure. Short-term, intermediate-term, and 
chronic-term risks are evaluated by comparing the estimated aggregate 
food, water, and residential exposure to the POD to ensure that the MOE 
called for by the product of all applicable UFs is not exceeded.
    1. Acute risk. An acute aggregate risk assessment takes into 
account exposure estimates from acute dietary consumption of food and 
drinking water. Using the exposure assumptions discussed in this unit 
for acute

[[Page 26542]]

exposure, EPA performed separate acute risk assessments for females 13 
to 49 years old and for the general population, including infants and 
children, based on different endpoints and aPADs. For females aged 13-
49, acute dietary exposure to triflumizole from food and water will 
occupy 67% of the aPAD chosen for that population subgroup. For the 
general population and population subgroups other than females aged 13-
49, acute dietary exposure to triflumizole is greatest for children 1-2 
years old. That subgroup will occupy 40% of the applicable aPAD.
    2. Chronic risk. Using the exposure assumptions described in this 
unit for chronic exposure, EPA has concluded that chronic exposure to 
triflumizole from food and water will utilize 44% 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 
triflumizole is not expected.
    3. Short-term and intermediate-term risk. Short-term and 
intermediate-term aggregate exposure takes into account short-term and 
intermediate-term residential exposure plus chronic exposure to food 
and water (considered to be a background exposure level). Although 
triflumizole is registered for commercial use on ornamentals in 
residential areas, this use is not expected to result in significant 
short-term or intermediate-term exposures of adults or children. 
Therefore, the short-term and intermediate-term aggregate risk is the 
sum of the risk from exposure to triflumizole through food and water 
and will not be greater than the chronic aggregate risk.
    4. Aggregate cancer risk for U.S. population. Based on the absence 
of significant tumor increases in two rodent carcinogenicity studies, 
triflumizole was classified as ``not likely to be carcinogenic to 
humans,'' and is not expected to pose a cancer risk to humans.
    5. 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 triflumizole residues.

IV. Other Considerations

A. Analytical Enforcement Methodology

    An adequate Gas Chromatography/Nitrogen Phosphorus Detector (GC/
NPD) method is available in Pesticide Analytical Methods (PAM) Vol. II 
(Method I, section 180.476) for determining the combined residues of 
triflumizole and its metabolites containing the FA-1-1 moiety in plant 
commodities. The method limit of quantitation (LOQ) is 0.5 ppm for 
plant commodities.

B. International Residue Limits

    There are no Codex, Canadian or Mexican maximum residue limits 
(MRLs) established for residues of triflumizole in or on commodities 
associated with this petition.

C. Revisions to Petitioned-For Tolerances

    Based upon review of the data supporting the petition, EPA revised 
the proposed tolerances for the following commodities: Brassica, leafy 
greens, subgroup 5B from 20 ppm to 40 ppm; and Brassica, head and stem, 
subgroup 5A from 5.0 ppm to 8.0 ppm. EPA revised the tolerance levels 
based on analysis of the residue field trial data using the Agency's 
Tolerance Spreadsheet in accordance with the Agency's Guidance 
Italicize Guiidance for Setting Pesticide Tolerances Based on Field 
Trial Data. EPA also revised the tolerance expression to clarify 1. 
That, as provided in FFDCA section 408(a)(3), the tolerance covers 
metabolites and degradates of triflumizole not specifically mentioned; 
and 2. That compliance with the specified tolerance levels is to be 
determined by measuring only the specific compounds mentioned in the 
tolerance expression. This change was made to both the tolerance 
expressions for plant commodities and animal commodities because it 
makes no substantive change to the meaning of the tolerance but rather 
only clarifies the existing language.

V. Conclusion

    Therefore, tolerances are established for combined residues of 
triflumizole, 1-(1-((4-chloro-2-(trifluoromethyl)phenyl)imino)-2-
propoxyethyl)-1 H -imidazole, and its metabolites containing the 4-
chloro-2-trifluoromethylaniline moiety, calculated as the parent 
compound, in or on leafy greens subgroup 4A, except spinach at 35 ppm; 
Brassica, head and stem, subgroup 5A at 8.0 ppm; Brassica, leafy 
greens, subgroup 5B at 40.0 ppm; cilantro, leaves at 35 ppm; Swiss 
chard at 18 ppm; pineapple at 4.0 ppm; papaya at 2.5 ppm; sapote, black 
at 2.5 ppm; canistel at 2.5 ppm; sapote, mamey at 2.5 ppm; mango at 2.5 
ppm; sapodilla at 2.5 ppm; star apple at 2.5 ppm; hop, dried cones at 
50.0 ppm; and turnip, greens at 40 ppm.

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

[[Page 26543]]

Unfunded Mandates Reform Act of 1995 (UMRA) (Public Law 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: May 22, 2009.
Daniel J. Rosenblatt,
Acting Director, Registration Division, Office of Pesticide Programs.

0
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
Section 180.476 is amended by revising the introductory text for 
paragraph (a)(1); by alphabetically adding the following commodities to 
the table in paragraph (a)(1); by revising the introductory text for 
paragraph (a)(2); and by removing the entries for Broccoli; Collards; 
Coriander, leaves; Dandelion, leaves; Kale; Mustard, greens; Parsley, 
leaves; Swiss chard; and Turnip, greens from the table in paragraph (b) 
to read as follows:

Sec.  180.476  Triflumizole; tolerances for residues

    (a) General. (1) Tolerances are established for residues of the 
fungicide triflumizole, including its metabolites and degradates, in or 
on the commodities listed in the table below. Compliance with the 
tolerance levels specified below is to be determined by measuring only 
the parent compound triflumizole, 1-(1-((4-chloro-2-
(trifluoromethyl)phenyl)imino)-2-propoxyethyl )-1 H -imidazole, and its 
metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, 
calculated as stoichiometric equivalent of the parent compound.

------------------------------------------------------------------------
                   Commodity                        Parts per million
------------------------------------------------------------------------
                                * * * * *
Brassica, head and stem, subgroup 5A...........                      8.0
Brassica, leafy greens, subgroup 5B............                       40
Canistel.......................................                      2.5
                                * * * * *
Cilantro, leaves...............................                       35
                                * * * * *
Hop, dried cones...............................                       50
Leafy greens subgroup 4A, except spinach.......                       35
Mango..........................................                      2.5
Papaya.........................................                      2.5
                                * * * * *
Pineapple......................................                      4.0
Sapodilla......................................                      2.5
Sapote, black..................................                      2.5
Sapote, mamey..................................                      2.5
Star apple.....................................                      2.5
                                * * * * *
Swiss chard....................................                       18
Turnip, greens.................................                       40
                                * * * * *
------------------------------------------------------------------------

    (2) Tolerances are established for residues of the fungicide 
triflumizole, including its metabolites and degradates, in or on the 
commodities of animal origin listed in the table below. Compliance with 
the tolerance levels specified below is to be determined by measuring 
only the parent compound triflumizole, 1-(1-((4-chloro-2-
(trifluoromethyl)phenyl)imino)-2-propoxyethyl )-1 H -imidazole, the 
metabolite 4-chloro-2-hydroxy-6-trifluoromethylaniline sulfate, and 
other metabolites containing the 4-chloro-2-trifluoromethylaniline 
moiety, calculated as the parent compound.
* * * * *
[FR Doc. E9-12949 Filed 6-2-09; 8:45 am]

BILLING CODE 6560-50-S