Document ID: EPA-HQ-OPP-2008-0813-0003
Agency: epa
Document Type: Rule
Title: Tembotrione; Pesticide Tolerances
Posted Date: 2009-09-18T04:00Z

[Federal Register: September 18, 2009 (Volume 74, Number 180)]
[Rules and Regulations]               
[Page 47891-47894]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr18se09-6]                         

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2008-0813; FRL-8431-5]

 
Tembotrione; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation revises the tolerances for residues of the 
herbicide tembotrione, including its metabolites and degradates, in or 
on corn, sweet forage; corn, sweet, stover; and corn, sweet, kernel 
plus cob with husks removed. Bayer CropScience requested these 
tolerances under the Federal Food, Drug, and Cosmetic Act (FFDCA).

DATES: This regulation is effective September 18, 2009. Objections and 
requests for hearings must be received on or before November 17, 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-2008-0813. 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:  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

[[Page 47892]]

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 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-2008-0813 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 November 17, 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-2008-0813, 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 December 3, 2008 (73 FR 73651) (FRL-
8391-3), 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 
8F7452) by Bayer CropScience, 2 T.W. Alexander Drive, Research Triangle 
Park, NC 27709. The petition requested that 40 CFR 180.634 be amended 
by revising tolerances for combined residues of the herbicide 
tembotrione and its metabolites in or on corn, sweet, kernel plus cob 
with husks removed from 0.04 to 0.01 parts per million (ppm); corn, 
sweet, forage from 1.0 ppm to 0.09 ppm; and corn, sweet, stover from 
1.2 ppm to 0.15 ppm. 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 
determined that the proposed tolerances should be revised as follows: 
corn, sweet, forage at 0.35 ppm; corn, sweet, stover at 0.60 ppm. EPA 
has also determined that the tolerance for corn, sweet, kernel plus cob 
with husks removed is acceptable at the proposed level of 0.01 ppm but 
that compliance with the tolerance level is to be determined by 
measuring only parent tembotrione. The reasons for these changes are 
explained in Unit IV.C.

III. Aggregate Risk Assessment and Determination of Safety

    Section 408(b)(2)(A)(i) of FFDCA allows EPA to establish a 
tolerance (the legal limit for a pesticide chemical residue in or on a 
food) only if EPA determines that the tolerance is ``safe.'' Section 
408(b)(2)(A)(ii) of FFDCA defines ``safe'' to mean that ``there is a 
reasonable certainty that no harm will result from aggregate exposure 
to the pesticide chemical residue, including all anticipated dietary 
exposures and all other exposures for which there is reliable 
information.'' This includes exposure through drinking water and in 
residential settings, but does not include occupational exposure. 
Section 408(b)(2)(C) of FFDCA requires EPA to give special 
consideration to exposure of infants and children to the pesticide 
chemical residue in establishing a tolerance and to ``ensure that there 
is a reasonable certainty that no harm will result to infants and 
children from aggregate exposure to the pesticide chemical residue. . . 
.''
    Consistent with section 408(b)(2)(D) of FFDCA, and the factors 
specified in section 408(b)(2)(D) of FFDCA, EPA has reviewed the 
available scientific data and other relevant information in support of 
this action. EPA has sufficient data to assess the hazards of and to 
make a determination on aggregate exposure for the petitioned-for 
tolerances for residues of the herbicide tembotrione and its 
metabolites and degradates, in or on corn, sweet, kernel plus cob with 
husks removed at 0.01 ppm; corn, sweet, forage at 0.35 ppm; and corn, 
sweet, stover at 0.60 ppm. EPA's assessment of exposures and risks 
associated with establishing tolerances follows.
    In the Federal Register of September 28, 2007 (72 FR 55078) (FRL-
8148-2) the Agency published a final rule establishing tolerances for 
combined residues of tembotrione and its M5 metabolite in or on corn, 
sweet, kernel plus cob with husks removed at 0.04 ppm; corn, sweet, 
forage at 1.0 ppm; and corn, sweet stover at 1.2 ppm. When the Agency 
conducted the risk assessment in support of the September 2007 
tolerance action, it considered the use of tembotrione on corn (field 
and sweet), incorporating potential residues of tembotrione and its 
metabolites in or on corn commodities and secondary residues of 
tembotrione in livestock commodities from consumption of treated 
feedstuffs, including corn forage. Residues of tembotrione on corn and 
livestock commodities were assumed to be present at tolerance levels. 
Since EPA considered the residues of tembotrione on corn, sweet, kernel 
plus cob with husks removed; corn, sweet, forage; and corn, sweet, 
stover at a higher level in its most recent risk assessments, reducing 
the tolerances on sweet corn commodities will reduce the estimated 
aggregate exposures resulting from use of tembotrione. While it is true 
that lowering the tolerances will reduce the estimated exposure to 
tembotrione, changes have occurred in toxicology data requirements for 
pesticides since the 2007 risk assessment was completed which could 
impact the Food Quality Protection Act (FQPA) safety factor (SF) for 
tembotrione, currently retained at 10X for acute and chronic dietary 
risk assessment. EPA's assessment of the new data requirements as they 
relate to the FQPA safety factor for tembotrione is discussed below.
    EPA began requiring acute and subchronic neurotoxicity testing and

[[Page 47893]]

functional immunotoxicity testing of all food and non-food use 
pesticides on December 26, 2007 (40 CFR part 158 subpart F). Acute and 
subchronic neurotoxicity studies in rats, as well as a developmental 
neurotoxicity (DNT) study in rats are available for tembotrione and 
were considered by EPA in its 2007 aggregate risk assessment and FQPA 
safety factor determination. Immunotoxicity data are not available for 
tembotrione. In the absence of specific immunotoxicity studies, EPA has 
evaluated the available tembotrione toxicity data to determine whether 
an additional database uncertainty factor is needed to account for 
potential immunotoxicity. The decreased absolute and relative thymus 
weights observed in female rats in the subchronic oral toxicity study 
were not corroborated with histopathological changes, and there were no 
thymus effects in other subchronic, chronic and carcinogenicity studies 
in rats. Therefore, the thymus weight changes in this study are 
spurious effects and not indicative of immunotoxicity. The increased 
incidence of minimal extramedullary hematopoeisis of the spleen in the 
rat offspring of the reproduction toxicity study and the anemia seen in 
the mice in the carcinogenicity study are indicators of toxicity to the 
hematopoietic system and not indicators of frank immunotoxicity. No 
other effects on organs of the immune system were seen, and the 
toxicity profile clearly indicates the eye, liver and kidneys to be the 
target organs for tembotrione-induced toxicity. Additionally, 
tembotrione does not belong to a class of chemicals (e.g., the 
organotins, heavy metals, or halogenated aromatic hydrocarbons) that 
would be expected to be immunotoxic in laboratory animals. Therefore, 
the Agency does not believe that conducting immunotoxicity testing will 
result in doses lower than those currently used for overall risk 
assessments (0.8 milligrams/kilograms/day (mg/kg/day) for acute and 
0.04 mg/kg/day for repeated exposures) and an additional uncertainty 
factor is not needed to account for potential immunotoxicity. Based on 
these considerations, EPA concludes that no uncertainty factors are 
required in addition to those used in the 2007 risk assessment for 
tembotrione.
    Therefore, based on the risk assessments discussed in the final 
rule published in the Federal Register of September 28, 2007, 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 tembotrione residues.

IV. Other Considerations

A. Analytical Enforcement Methodology

    An Adequate enforcement methodology, liquid chromatography/mass 
spectroscopy (LC/MS/MS) method 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) 305-905; e-mail address: 
residuemethods@epa.gov.

B. International Residue Limits

    There is neither a Codex proposal, nor Canadian or Mexican limits 
for residues of tembotrione and its metabolites in or on crops or 
livestock commodities.

C. Revisions to Petitioned-For Tolerances

    The submitted data support the following revised tolerances for 
residues of tembotrione in or on sweet corn commodities: Corn, sweet, 
kernel plus cob with husks removed at 0.01 ppm; corn, sweet, forage at 
0.35 ppm; corn, sweet, stover at 0.60 ppm. EPA revised the tolerance 
levels for corn, sweet, forage and stover from those proposed by the 
registrant based on analyses of the residue field trial data using the 
Agency's Tolerance Spreadsheet in accordance with the Agency's Guidance 
for Setting Pesticide Tolerances Based on Field Trial Data. There were 
no detectable residues of tembotrione in corn, sweet, kernel plus cob 
with husks removed; and metabolism data for tembotrione show that while 
M5 is a major metabolite in forage and stover, it was present at less 
then 1% of the Total Radioactive Residue (TRR) in corn grain. Based on 
the results of these field trial and metabolism studies, the tolerance 
for corn, sweet, kernel plus cob with husks removed is being 
established at the limit of quantitation (0.01 ppm) for tembotrione.
    Tolerances for tembotrione are currently expressed in terms of ``2-
[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-
1,3-cyclohexanedione, and its metabolite, 2-[2-chloro-4-
(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-4,6-
dihydroxy-1,3-cyclohexanedione.'' EPA is revising the tolerance 
expression for existing tolerances and the new tolerances on sweet corn 
commodities to clarify the chemical moieties that are covered by the 
tolerances and specify how compliance with the tolerances is to be 
measured. The revised tolerance expression makes clear that the 
tolerances cover ``residues of tembotrione, including its metabolites 
and degradates,'' and that compliance with the tolerance levels for all 
commodities except corn, sweet, kernel plus cob with husks removed, 
will be determined by measuring only the sum of tembotrione, 2-[2-
chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-
1,3-cyclohexanedione and its metabolite, 2-[2-chloro-4-
(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy) methyl]benzoyl]-4,6-
dihydroxy-1,3-cyclohexanedione, calculated as the stoichiometric 
equivalent of tembotrione. Compliance with the tolerance level for 
corn, sweet, kernel plus cob with husks removed will be determined by 
measuring only tembotrione.
    EPA has determined that it is reasonable to make this change final 
without prior proposal and opportunity for comment, because public 
comment is not necessary, in that the change has no substantive effect 
on the tolerances, but rather is merely intended to clarify the 
existing tolerance expression.

V. Conclusion

    Therefore, tolerances are revised for residues of the herbicide 
tembotrione, including its metabolites and degradates, in or on corn, 
sweet, kernel plus cob with husks removed at 0.01 ppm; corn, sweet, 
forage at 0.35 ppm; and corn, sweet, stover at 0.60 ppm. Compliance 
with the tolerance levels specified for corn, sweet, forage and stover 
is to be determined by measuring only the sum of tembotrione, 2-[2-
chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-
1,3-cyclohexanedione and its metabolite, 2-[2-chloro-4-
(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy) methyl]benzoyl]-4,6-
dihydroxy-1,3-cyclohexanedione, calculated as the stoichiometric 
equivalent of tembotrione, in or on the commodities. Compliance with 
tolerance level for corn, sweet, kernel plus cob with husks removed, 
will be determined by measuring only tembotrione.

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

[[Page 47894]]

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: September 8, 2009.
Lois Rossi,
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. Section 180.634 is amended as follows:
    a. By revising the introductory text of paragraph (a) and 
redesignating it as paragraph (a)(1).
    b. In the table to newly redesignated paragraph (a)(1) by revising 
the entries for corn, sweet, forage, and corn, sweet, stover, and by 
removing the entry for corn, sweet, kernel plus cob with husks removed.
    c. By adding paragraph (a)(2).
The revised and added text reads as follows:

Sec.  180.634  Tembotrione; tolerances for residues.

    (a) * * * (1) Tolerances are established for residues of the 
herbicide tembotrione, including its metabolites and degradates, in or 
on the commodities listed in the table to this paragraph. Compliance 
with the tolerance levels specified below is to be determined by 
measuring only the sum of tembotrione, 2-[2-chloro-4-(methylsulfonyl)-
3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione and its 
metabolite, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy) 
methyl]benzoyl]-4,6-dihydroxy-1,3-cyclohexanedione, calculated as the 
stoichiometric equivalent of tembotrione, in or on the following 
commodities.

------------------------------------------------------------------------
                      Commodity                        Parts per million
------------------------------------------------------------------------
                                * * * * *
Corn, sweet, forage..................................               0.35
Corn, sweet, stover..................................               0.60
                                * * * * *
------------------------------------------------------------------------

    (2) Tolerances are established for residues of the herbicide 
tembotrione, including its metabolites and degradates, in or on the 
commodities listed in the table to this paragraph. Compliance with the 
tolerance levels specified below is to be determined by measuring only 
tembotrione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-
trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione in or on the 
following commodities.

------------------------------------------------------------------------
                      Commodity                        Parts per million
------------------------------------------------------------------------
Corn, sweet, kernel plus cob with husks removed......               0.01
------------------------------------------------------------------------

* * * * *

[FR Doc. E9-22519 Filed 9-17-09; 8:45 am]

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