Document ID: EPA-HQ-OPP-2008-0217-0003
Agency: epa
Document Type: Rule
Title: Isoxaflutole; Pesticide Tolerances
Posted Date: 2008-12-12T05:00Z

[Federal Register: December 12, 2008 (Volume 73, Number 240)]
[Rules and Regulations]               
[Page 75605-75609]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr12de08-12]                         

-----------------------------------------------------------------------

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.

-----------------------------------------------------------------------

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

[[Page 75606]]

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: Joanne Miller, Registration Division 
(7505P), Office of Pesticide Programs, Environmental Protection Agency, 
1200 Pennsylvania Ave., NW., Washington, DC 20460-0001; telephone 
number: (703) 305-6224; e-mail address: miller.joanne@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.

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 (703) 305-5805.

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.

[[Page 75607]]

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

[[Page 75608]]

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: (410) 305-2905; e-mail 
address: residuemethods@epa.gov.

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

[[Page 75609]]

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
------------------------------------------------------------------------

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

BILLING CODE 6560-50-S