[Federal Register: December 12, 2008 (Volume 73, Number 240)]
[Rules and Regulations]
[Page 75605-75609]
[DOCID:fr12de08-12]

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2008-0217; FRL-8393-1]

Isoxaflutole; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation amends the pesticide tolerance for
isoxaflutole by removing isoxaflutole's benzoic acid metabolite (RPA
203328) from the established tolerance expression and revising downward
tolerance levels for isoxaflutole in or on field corn. Bayer
CropScience requested these tolerances under the Federal Food, Drug,
and Cosmetic Act (FFDCA).

DATES: This regulation is effective December 12, 2008. Objections and
requests for hearings must be received on or before February 10, 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-2008-0217. 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<PHONE_NUMBER>.

FOR FURTHER INFORMATION CONTACT: Joanne Miller, Registration Division
(7505P), Office of Pesticide Programs, Environmental Protection Agency,
1200 Pennsylvania Ave., NW., Washington, DC 20460-0001; telephone
number:<PHONE_NUMBER>; e-mail address<EMAIL_ADDRESS>
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.

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 pilot e-CFR
site 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-2008-217 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 February 10, 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-2008-217, 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<PHONE_NUMBER>.

II. Petition for Tolerance

    In the Federal Register of April 16, 2008 (73 FR 20632) (FRL-8359-
1), 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
8F7328) by Bayer CropScience, 2 T.W. Alexander Drive, Research Triangle
Park, NC 27709. The petition requested that the tolerance for
isoxaflutole at 40 CFR 180.537 be amended by removing the benzoic acid
metabolite (RPA 203328) from the established tolerance expression and
revising downward the tolerance levels for the following raw
agricultural commodities: Corn, field, grain; corn, field, forage; and
corn, field, stover. The proposed level for each of these tolerances is
0.02 parts per million (ppm). Bayer CropScience requested that the
tolerance for isoxaflutole be amended based on the results of several
toxicology studies submitted for the benzoic acid metabolite,
demonstrating RPA 203328 is not of toxicological concern. That notice
referenced a summary of the petition prepared by Bayer CropScience 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.
    Based upon review of the data supporting the petition, EPA has
revised the proposed tolerance level for the combined residues of
isoxaflutole and its metabolite RPA 202248, calculated as the parent
compound, in or on corn, field, forage from 0.02 ppm to 0.04 ppm.
Adequate crop field trial data with isoxaflutole showed quantifiable
residues of isoxaflutole and RPA 202248 in field corn forage. These
residues were found only in samples from a single trial and no residues
were found in field corn grain or stover in any of the trials. Because
the combined residues of isoxaflutole and RPA 202248 in that forage
sample were at 0.029 ppm, a tolerance of 0.04 ppm is necessary for
forage. Additionally, in light of the revised, and significantly lower,
tolerances for isoxaflutole on field corn commodities, EPA reassessed
the necessity for tolerances for isoxaflutole on meat, milk, poultry,
and egg commodities. Meat, milk, poultry, and egg tolerances are
necessary for a pesticide if pesticide residues in such commodities are
likely following consumption by livestock of feed commodities bearing
pesticide residues. Using the new tolerances and existing animal
feeding studies with isoxaflutole, EPA determined that there was no
reasonable expectation of finite isoxaflutole residues in livestock as
the maximum residues expected are well below the limit of detection of
the analytical enforcement method. Accordingly, EPA is revoking the
existing isoxaflutole meat, milk, and egg tolerances as unnecessary.

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 the combined residues of isoxaflutole and its metabolite
RPA 202248, calculated as the parent compound, in or on corn, field,
forage at 0.04 ppm; corn, field, grain at 0.02 ppm; and corn, field,
stover at 0.02 ppm. EPA's assessment of exposures and risks associated
with establishing tolerances follows.

A. Removal of the Benzoic Acid Metabolite RPA 203328

    The previous risk assessment concluded that RPA 203328 could not be
excluded from the risk assessment and tolerance expression based on a
developmental endpoint of parent isoxaflutole until an acceptable rat
developmental toxicity study was submitted to the EPA. Additional
toxicity studies have been performed on the metabolite RPA 203328 since
the last risk assessment, including an acceptable developmental
toxicity study on RPA 203328. No evidence of teratogenicity was
observed in this study and based on this data EPA concluded that the
developmental toxicity observed with isoxaflutole is not due to RPA
203328. EPA thus determined that the residues of concern for both the
tolerance expression and risk assessment are isoxaflutole and RPA
202248.

B. Safety of Isoxaflutole Tolerances

    EPA's last tolerance rulemaking with regard to isoxaflutole
occurred on September 23, 1998. (63 FR 50773) (FRL-6029-3). In that
action, isoxaflutole tolerances were established for combined residues
of isoxaflutole and its metabolites RPA 202248 and RPA 203328,
calculated as the parent compound, in or on the following raw
agricultural commodities: Corn, field, forage at 1.0 ppm; corn, field,
grain at 0.20 ppm; and corn, field, stover at 0.50 ppm. Tolerances were
established for the combined residues of isoxaflutole and its
metabolite RPA 202248, calculated as the parent compound, in or on the
following raw agricultural commodities: Cattle, fat at 0.20 ppm;
cattle, liver at 0.50 ppm; cattle, meat at 0.20 ppm; cattle, meat
byproducts, except liver at 0.10 ppm; egg at 0.01 ppm; goat, fat at
0.20 ppm; goat, liver at 0.50 ppm; goat, meat at 0.20 ppm; goat, meat
byproducts, except liver at 0.10 ppm; hog, fat at 0.20 ppm; hog, liver
at 0.50 ppm; hog, meat at 0.20 ppm; hog, meat byproducts, except liver
at 0.10 ppm; horse, fat at 0.20 ppm; horse, liver at 0.50 ppm; horse,
meat at 0.20 ppm; horse, meat byproducts, except liver at 0.10 ppm;
milk at 0.02 ppm; poultry, fat at 0.20 ppm; poultry, liver at 0.30 ppm;
poultry, meat at 0.20 ppm; sheep, fat at 0.20 ppm; sheep, liver at 0.50
ppm; sheep, meat at 0.20 ppm; and sheep, meat byproducts, except liver
at 0.10 ppm.
    In the 1998 tolerance action, EPA assumed that the residues of
concern in field corn were isoxaflutole and its metabolites RPA 202248
and RPA 203328. As explained in this unit, however, EPA has now
determined that only the parent isoxaflutole and the RPA 202248
metabolite pose a risk of concern. Thus, the risk assessment done in
conjunction with the 1998 rulemaking, which showed isoxaflutole
exposure to be safe, greatly overstates isoxaflutole exposure in
comparison to the revised tolerances. First, as to exposure through
human foods produced from field corn (e.g., corn meal, corn oil), the
levels of isoxaflutole residues of concern in such foods are an order
of magnitude lower than previously assumed. Second, as to meat, milk,
poultry, and eggs from livestock consuming isoxaflutole-treated field
corn, EPA has concluded that there is no reasonable expectation of
combined residues of isoxaflutole and RPA 202248 in such commodities.
Accordingly, there is essentially no human exposure to isoxaflutole
residues in meat, milk, poultry, and eggs from use of isoxaflutole on
field corn. For these reasons, the 1998 risk assessment is a very
conservative assessment of the potential risk from use of isoxaflutole
on field corn. Refer to the Federal Register of September 23, 1998 (63
FR 50773) (FRL-6029-3), available at http://www.regulations.gov, for a
detailed discussion of the 1998 isoxaflutole aggregate risk assessments
and determination of safety.
    Since the 1998 rulemaking, EPA has received a developmental
neurotoxicity study with isoxaflutole. Although EPA has required that
the study to be redone due to a lack of morphometric analyses of the
brain, the maternal and offspring no observed adverse effect levels
(NOAELs) in the study were otherwise identified as 25 milligram/
kiligram/day (mg/kg/day). This value is above the Point of Departure
(POD) used in assessing acute and chronic risk in the 1998 risk
assessment. There, EPA used a lowest observed adverse effect level
(LOAEL) of 5 mg/kg/day as the POD for acute risks and a NOAEL of 2 mg/
kg/day as the POD for chronic risks. Thus, these new data do not
suggest that isoxaflutole is more toxic than was assumed in the 1998
assessment. Further, it should be noted that in assessing isoxaflutole
risk, EPA applied an additional safety factor of 30X for the protection
of infants and children in addressing acute risks and an additional
safety factor of 10X for the protection of infants and children in
addressing chronic risks. These additional safety factors were used to
address the absence of a developmental neurotoxicity study and reliance
on a LOAEL. In another development occurring since the 1998 rulemaking,
EPA has noted, in tolerance rulemakings for several other pesticides
that pesticides such as isoxaflutole which inhibit the liver enzyme 4-
hydroxyphenylpyruvate dioxygenase (HPPD) may operate through a common
mechanism of toxicity. To address this issue, EPA has conducted a
cumulative screening assessment for these pesticides and concluded
that, even if there is common mechanism for HPPD-inhibition, cumulative
exposure from these pesticides does not raise a risk concern. Refer to
the Federal Register of February 20, 2008 (73 FR 9221) (FRL-8344-7).
Further cumulative analysis is unnecessary for this action because of
EPA's conclusion that the revised isoxaflutole tolerances result in
substantially lower isoxaflutole exposure than previously assumed.
    Accordingly, taking into account the prior risk assessment for
isoxaflutole, EPA's revised analysis of the level of human exposure
from use of

isoxaflutole on field corn, the developmental neurotoxicity study, and
EPA's screening analysis of HPPD-inhibiting pesticides, EPA concludes
that there is a reasonable certainty that no harm will result to the
general population, and to infants and children, from aggregate
exposure to isoxaflutole residues.

IV. Other Considerations

A. Analytical Enforcement Methodology

    A practical analytical method has been developed for detecting and
quantifying levels of isoxaflutole and RPA 202248 in or on raw
agricultural commodities obtained from field corn. This method allows
monitoring of these commodities with residues at or above the levels
proposed. Quantification of analytes as individual components is
performed by daughter-ion detection using liquid chromatography/mass
spectroscopy (LC/MS/MS). The limit of quantification (LOQ) for all
analytes is 0.01 ppm. The proposed analytical enforcement method to
determine isoxaflutole-derived residues in plants has been validated by
an independent laboratory.
    Adequate enforcement methodology LC/MS/MS is available to enforce
the tolerance expression. The method may be requested from: Chief,
Analytical Chemistry Branch, Environmental Science Center, 701 Mapes
Rd., Ft. Meade, MD 20755-5350; telephone number:<PHONE_NUMBER>; e-mail
address<EMAIL_ADDRESS>
B. International Residue Limits

    There are no Codex, Canadian, or Mexican maximum residue limits
(MRLs) established for residues of isoxaflutole in crop or livestock
commodities.

V. Conclusion

    Therefore, EPA has revised tolerances for the combined residues of
isoxaflutole and its metabolites RPA 202248 and RPA 203328, calculated
as the parent compound, in or on corn, field, forage at 0.04 ppm; corn,
field, grain at 0.02 ppm; and corn, field, stover at 0.02 ppm; and has
removed the benzoic acid metabolite (RPA 203328) from the established
tolerance expression. EPA has removed the established tolerances for
the combined residues of isoxaflutole and its metabolite RPA 202248,
calculated as the parent compound, in or on cattle, fat at 0.20 ppm;
cattle, liver at 0.50 ppm; cattle, meat at 0.20 ppm; cattle, meat
byproducts, except liver at 0.10 ppm; egg at 0.01 ppm; goat, fat at
0.20 ppm; goat, liver at 0.50 ppm; goat, meat at 0.20 ppm; goat, meat
byproducts, except liver at 0.10 ppm; hog, fat at 0.20 ppm; hog, liver
at 0.50 ppm; hog, meat at 0.20 ppm; hog, meat byproducts, except liver
at 0.10 ppm; horse, fat at 0.20 ppm; horse, liver at 0.50 ppm; horse,
meat at 0.20 ppm; horse, meat byproducts, except liver at 0.10 ppm;
milk at 0.02 ppm; poultry, fat at 0.20 ppm; poultry, liver at 0.30 ppm;
poultry, meat at 0.20 ppm; sheep, fat at 0.20 ppm; sheep, liver at 0.50
ppm; sheep, meat at 0.20 ppm; and sheep, meat byproducts, except liver
at 0.10 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 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: December 3, 2008.
Donald R. Stubbs,
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
2. In Sec.  180.537, paragraph (a) is revised to read as follows:

Sec.  180.537  Isoxaflutole; tolerances for residues

    (a) General. Tolerances are established for the combined residues
of

isoxaflutole 5-cyclopropyl-4-(2-methylsulfonyl-4-
trifluoromethylbenzoyl) isoxazole and its metabolite 1-(2-
methylsulfonyl-4-trifluoromethylphenyl)-2-cyano-3-cyclopropyl propan-
1,3-dione (RPA 202248), calculated as the parent compound, in or on the
following raw agricultural commodities:

------------------------------------------------------------------------
              Commodity                        Parts per million
------------------------------------------------------------------------
Corn, field, forage.................                                0.04
Corn, field, grain..................                                0.02
Corn, field, stover.................                                0.02
------------------------------------------------------------------------

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[FR Doc. E8-29467 Filed 12-11-08; 8:45 am]

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