[Federal Register Volume 77, Number 234 (Wednesday, December 5, 2012)]
[Rules and Regulations]
[Pages 72223-72226]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2012-29248]



40 CFR Part 180

[EPA-HQ-OPP-2012-0202; FRL-9371-6]

Clodinafop-Propargyl; Pesticide Tolerance

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.


SUMMARY: This regulation reduces the established tolerance for residues 
of clodinafop-propargyl in or on wheat, grain. Syngenta Crop 
Protection, LLC requested this tolerance change under the Federal Food, 
Drug, and Cosmetic Act (FFDCA).

DATES: This regulation is effective December 5, 2012. Objections and 
requests for hearings must be received on or before February 4, 2013 
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: The docket for this action, identified by docket 
identification (ID) number EPA-HQ-OPP-2012-0202, is available at http://www.regulations.gov or at the Office of Pesticide Programs Regulatory 
Public Docket (OPP Docket) in the Environmental Protection Agency 
Docket Center (EPA/DC), EPA West Bldg., Rm. 3334, 1301 Constitution 
Ave. NW., Washington, DC 20460-0001. The Public Reading Room is open 
from 8:30 a.m. to 4:30 p.m., Monday through Friday, excluding legal 
holidays. The telephone number for the Public Reading Room is (202) 
566-1744, and the telephone number for the OPP Docket is (703) 305-
5805. Please review the visitor instructions and additional information 
about the docket available at http://www.epa.gov/dockets.

FOR FURTHER INFORMATION CONTACT: Mindy Ondish, Registration Division 
(7505P), Office of Pesticide Programs, Environmental Protection Agency, 
1200 Pennsylvania Ave. NW., Washington, DC 20460-0001; telephone 
number: (703) 605-0723; email address: [email protected].


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. 
The following list of North American Industrial Classification System 
(NAICS) codes is not intended to be exhaustive, but rather provides a 
guide to help readers determine whether this document applies to them. 
Potentially affected entities may include:
     Crop production (NAICS code 111).
     Animal production (NAICS code 112).
     Food manufacturing (NAICS code 311).
     Pesticide manufacturing (NAICS code 32532).

B. How can I get electronic access to other related information?

    You may access a frequently updated electronic version of EPA's 
tolerance regulations at 40 CFR part 180 through the Government 
Printing Office's e-CFR site at http://ecfr.gpoaccess.gov/cgi/t/text/text-idx?&c=ecfr&tpl=/ecfrbrowse/Title40/40tab_02.tpl. To access the 
OCSPP test guidelines referenced in this document electronically, 
please go to http://www.epa.gov/ocspp and select ``Test Methods and 

C. How can I file an objection or hearing request?

    Under FFDCA section 408(g), 21 U.S.C. 346a, any person may file an 
objection to any aspect of this regulation and may also request a 
hearing on those objections. You must file your objection or request a 
hearing on this regulation in accordance with the instructions provided 
in 40 CFR part 178. To ensure proper receipt by EPA, you must identify 
docket ID number EPA-HQ-OPP-2012-0202 in the subject line on the first 
page of your submission. All objections and requests for a hearing must 
be in writing, and must be received by the Hearing Clerk on or before 
February 4, 2013. Addresses for mail and hand delivery of objections 
and hearing requests are provided in 40 CFR 178.25(b).
    In addition to filing an objection or hearing request with the 
Hearing Clerk as described in 40 CFR part 178, please submit a copy of 
the filing (excluding any Confidential Business Information (CBI)) for 
inclusion in the public docket. Information not marked confidential 
pursuant to 40 CFR part 2 may be disclosed publicly by EPA without 
prior notice. Submit the non-CBI copy of your objection or hearing 
request, identified by docket ID number EPA-HQ-OPP-2012-0202, by one of 
the following methods:
     Federal eRulemaking Portal: http://www.regulations.gov. 
Follow the online instructions for submitting comments. Do not submit 
electronically any information you consider to be Confidential Business 
Information (CBI) or other information whose disclosure is restricted 
by statute.
     Mail: OPP Docket, Environmental Protection Agency Docket 
Center (EPA/DC), (28221T), 1200 Pennsylvania Ave. NW., Washington, DC 
     Hand Delivery: To make special arrangements for hand 
delivery or delivery of boxed information, please follow the 
instructions at http://www.epa.gov/dockets/contacts.htm.
    Additional instructions on commenting or visiting the docket, along 
with more information about dockets generally, is available at http://www.epa.gov/dockets.

II. Summary of Petitioned-for Tolerance

    In the Federal Register of October 17, 2012 (77 FR 63782) (FRL-
9366-2), EPA issued a document pursuant to FFDCA section 408(d)(3), 21 
U.S.C. 346a(d)(3), announcing the filing of a pesticide petition (PP 
1F7955) by Syngenta Crop Protection, LLC, P.O. Box 18300, Greensboro, 
NC 27419-8300. The petition requested that 40 CFR 180.559 be amended by 
lowering the established tolerance for residues of the herbicide 
clodinafop-propargyl in or on wheat, grain from 0.1 to 0.02 parts per 
million (ppm). That document referenced a summary of the petition 
prepared by Syngenta Crop Protection, LLC, the registrant, which is 
available in the docket, http://www.regulations.gov. Comments were 
received on the notice of filing. EPA's response to these comments is 
discussed in Unit IV.C. Finally, EPA is revising the tolerance

[[Page 72224]]

expression for the reasons 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 FFDCA section 408(b)(2)(D), and the factors 
specified in FFDCA section 408(b)(2)(D), 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 clodinafop-propargyl including 
exposure resulting from the tolerance established by this action. EPA's 
assessment of exposures and risks associated with clodinafop-propargyl 
    In the Federal Register of June 22, 2000 (65 FR 38765) (FRL-6590-
7), EPA published a final rule establishing tolerances for combined 
residues of the herbicide clodinafop-propargyl and its acid metabolite 
in or on wheat (forage, grain, hay, and straw) based upon EPA's 
conclusion that aggregate exposure to clodinafop-propargyl is safe for 
the general population, including infants and children. Since 2000, 
there have been no additional tolerance actions for clodinafop-
    This action decreases the established tolerance for residues of 
clodinafop-propargyl in or on the commodity wheat, grain from 0.1 to 
0.02 ppm, based upon a change to an enforcement method (Method MS 247) 
with a lower limit of quantitation (LOQ) on wheat grain than the 
current methods. Since an established tolerance is being reduced, which 
is expected to have no significant exposure effect, no new dietary 
exposure assessment, drinking water exposure assessment, or non-dietary 
exposure assessment was conducted.
    Except as supplemented by the information described in this unit, 
EPA is relying on the safety finding in the 2000 rulemaking and the 
risk assessment underlying that action in amending the tolerance for 
wheat grain. Further information regarding the safety finding for the 
last rulemaking can be found in the Federal Register of June 22, 2000, 
at http://www.epa.gov/fedrgstr/EPA-PEST/2000/June/Day-22/p15715.htm. 
Although significant new data have been received since the 2000 
rulemaking, as discussed in this unit, these data do not indicate that 
risk from exposure to clodinafop-propargyl were understated. To the 
contrary, these new data suggest that EPA's prior risk assessment 
overstated clodinafop-propargyl risks. Further information about EPA's 
risk assessment and determination of safety for this action can be 
found at http://www.regulations.gov in document ``Clodinafop-propargyl. 
Human Health Risk Assessment for Clodinafop-propargyl to Reduce the 
Established Tolerance on Wheat Grain'' in docket ID number EPA-HQ-OPP-
    For the 2000 rulemaking, the toxicity database for clodinafop-
propargyl was considered incomplete. Acute neurotoxicity, subchronic 
neurotoxicity, developmental neurotoxicity, and in vitro cytogenetic 
studies were required. The absence of these studies, along with 
quantitative and qualitative evidence of increased susceptibility, and 
evidence of potential endocrine disruption, led EPA to retain an 
additional safety factor for the protection of infants and children as 
provided by FFDCA section 408(b)(2)(C) (i.e., 10X for acute risk for 
females 13+ and chronic risk; 3X for acute risk for infants and 
children). With the exception of the cytogenetic studies, the required 
studies have since been submitted and found acceptable. Studies were 
submitted which removed mutagenicity concerns and thus the cytogenetic 
studies were no longer required.
    In all likelihood, the submission of these data will lead EPA to 
remove the additional safety factor for the protection of infants and 
children when it formally revises the clodinafop-propargyl risk 
assessment. The absence of these data was the primary reason for 
retaining that additional factor. Currently, there is a data gap for an 
immunotoxicity study. In 2007 changes to 40 CFR part 158 imposed new 
data requirements for immunotoxicity testing (OPPTS Guideline 870.7800) 
for pesticide registration. This study has not been submitted for 
clodinafop-propargyl. The absence of this study is unlikely to result 
in retention of an additional safety factor. EPA has only retained an 
additional safety factor when there is a data gap for immunotoxicity 
where the database shows clear evidence of immunotoxicity and 
immunotoxic effects were seen at the LOAEL that defined the point of 
departure (POD). For clodinafop-propargyl, there is evidence in the 
current toxicological database that clodinafop-propargyl may perturb 
immune function but this evidence is not strong and it did not affect 
the choice of the POD. In the subchronic oral toxicity study in rats, 
treatment-related effects were observed (37% decrease in thymus weight 
and increased thymic atrophy). Thymus effects were observed only in 
males at the highest treatment-dose (71 mg/kg/day), and were fully 
reversed after a 4-week recovery period. No thymus effects were 
observed in the chronic toxicity/carcinogenicity study in rats. No 
other indicators of structural immunotoxicity were observed in the 
current database. While an immunotoxicity study is required to complete 
the database, the absence of this study is not expected to alter the 
aRfD or cRfD for clodinafop-propargyl. Hence, by relying on the 2000 
risk assessment and the additional safety factors retained in that 
assessment, EPA has taken a conservative approach that is likely to 
overstate the estimated risk of clodinafop-propargyl.
    The EPA has determined that the results of the neurotoxicity 
studies adequately elucidate the hazard but do not affect EPA's 
derivation of clodinafop-propargyl's acute reference dose (aRfD) or 
chronic reference dose (cRfD). The NOAELs for adverse effects seen in 
the neurotoxicity studies are well above the NOAELs in the studies used 
as PODs. Thus, the PODs used in the risk assessment for the 2000 
rulemaking for clodinafop-propargyl, as well as the aRfD and the cRfD 
derived from those PODs, are protective of all effects, including 
neurotoxicity, observed in the neurotoxicity studies.
    Previously, EPA considered clodinafop-propargyl as likely to be 
carcinogenic to humans based on increased incidences of prostate tumors 
in male rats, ovarian adenomas in female rats, liver tumors in male and 
female mice, and blood vessel tumors in female mice and estimated 
cancer risk using a linear (non-threshold) approach. Since that time, 
additional data have been submitted, including a re-evaluation of the 
proliferative lesions in the rat ovary and prostate as well as

[[Page 72225]]

mode of action data for mouse liver tumors. In 2006, EPA revised its 
cancer determination on clodinafop-propargyl concluding that the 
evidence was no greater than suggestive of carcinogenic potential and 
thus did not support the finding that clodinafop-propargyl was likely 
to be carcinogenic to humans. That conclusion was based on the 
    1. Prostate tumors (driven mainly by adenomas) were seen in one sex 
(male) of one species (rat) at the high dose only.
    2. There is no mutagenicity concern for clodinafop-propargyl.
    3. The weight-of-evidence supports activation of peroxisome 
proliferator-activated receptor alpha (PPAR'') as the mode of action 
for clodinafop-induced hepatocarcinogenesis in mice. While the PPAR 
mode of action for liver tumors in mice is theoretically plausible in 
humans, hepatocarcinogenesis by this mode of action is quantitatively 
implausible and unlikely to take place in humans based on quantitative 
species differences in PPAR'' activation and toxicokinetics.
    4. Ovarian tumors in the rat and vascular tumors in the mouse were 
not considered to be treatment-related in the Second Report of the 
Cancer Assessment Review Committee.
    Given this limited evidence of carcinogenic effects in animals or 
effects unlikely to be relevant to humans, the use of a linear (non-
threshold) approach for assessing cancer risk is no longer appropriate. 
Instead, EPA has determined that the chronic threshold-based risk 
assessment (i.e., the cRfD approach) will be protective of any cancer 
    Based upon the 2000 rulemaking and the other information discussed 
in this unit, 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 clodinafop residues. EPA relies 
upon those risk assessments and the findings made in the Federal 
Register document in support of this action.

IV. Other Considerations

A. Analytical Enforcement Methodology

    An analytical method using high-performance liquid chromatography 
with tandem mass spectrometry detection (LC/MS/MS), Enviro-Test 
Laboratories Report No. MS 247 (Method MS 247) was submitted in support 
of reducing the tolerance for wheat grain.
    This LC/MS/MS method has a lower LOQ than the current HPLC-UV 
methods (REM 138.01 for clodinafop-propargyl and REM 138.10 for 
clodinafop) for the determination of residues of clodinafop-propargyl 
(CGA-184927) and its metabolite clodinafop (CGA-193469) in or on wheat 
commodities. Method MS 247 was adequately validated using fortified 
samples of wheat grain, forage, and straw.
    The current enforcement methods (REM 138.01 for clodinafop-
propargyl and REM 138.10 for clodinafop) can serve as confirmatory 
methods for Method MS 247 on wheat grain since they use a different 
detection system. Therefore, the LC/MS/MS Method MS 247 is adequate as 
an enforcement analytical method for determination of residues of 
clodinafop-propargyl and its metabolite clodinafop in wheat grain at 
0.02 ppm (0.01 ppm for each analyte). The methods referenced in this 
unit may be requested from: Chief, Analytical Chemistry Branch, 
Environmental Science Center, 701 Mapes Rd., Ft. Meade, MD 20755-5350; 
telephone number: (410) 305-2905; email address: 
[email protected].

B. International Residue Limits

    In making its tolerance decisions, EPA seeks to harmonize U.S. 
tolerances with international standards whenever possible, consistent 
with U.S. food safety standards and agricultural practices. EPA 
considers the international maximum residue limits (MRLs) established 
by the Codex Alimentarius Commission (Codex), as required by FFDCA 
section 408(b)(4). The Codex Alimentarius is a joint United Nations 
Food and Agriculture Organization/World Health Organization food 
standards program, and it is recognized as an international food safety 
standards-setting organization in trade agreements to which the United 
States is a party. EPA may establish a tolerance that is different from 
a Codex MRL; however, FFDCA section 408(b)(4) requires that EPA explain 
the reasons for departing from the Codex level.
    The Codex has not established MRLs for clodinafop-propargyl in or 
on any commodities.

C. Response to Comments

    EPA received an anonymous comment in response to the Notice of 
Filing that objected to the proposed tolerance petition. The commenter 
stated that the objection was to the ``Syngenta application to increase 
[the tolerance] from .01 to .02 ppm''. Because this action is to 
decrease the tolerance from 0.1 to 0.02 ppm, it is assumed that the 
commenter misinterpreted the proposed petition and would have no 
objections otherwise. The commenter made additional comments proposing 
to eliminate tolerances and pesticides altogether. The Agency 
understands the commenter's concerns and recognizes that some 
individuals believe that certain pesticide chemicals should not be 
permitted in our food. However, the existing legal framework provided 
by section 408 of the Federal Food, Drug and Cosmetic Act (FFDCA) 
states that tolerances may be set when persons seeking such tolerances 
or exemptions have demonstrated that the pesticide meets the safety 
standard imposed by that statute. When new or amended tolerances are 
requested for residues of a pesticide in food or feed, the Agency, as 
is required by section 408 of the FFDCA, estimates the risk of the 
potential exposure to these residues. The Agency has concluded after 
this assessment that there is a reasonable certainty that no harm will 
result from aggregate human exposure to clodinafop-propargyl.
    EPA received a second anonymous comment in response to the Notice 
of Filing which urged that regulations in general be stopped because 
they are killing small businesses. This comment is considered 
irrelevant to this action because the safety standard for approving 
tolerances under section 408 of FFDCA focuses on potential harm to 
human health and does not permit consideration of effects on any type 
of businesses.

D. Revisions to Petitioned-for Tolerances

    Finally, the EPA is revising the tolerance expression to:
    1. Clarify that, as provided in FFDCA section 408(a)(3), the 
tolerance covers metabolites and degradates of clodinafop-propargyl not 
specifically mentioned; and
    2. Clarify that compliance with the specified tolerance levels is 
to be determined by measuring only the specific compounds mentioned in 
the tolerance expression.

 V. Conclusion

    Therefore, the established tolerance for residues of clodinafop-
propargyl in or on wheat, grain is reduced from 0.1 to 0.02 ppm.

VI. Statutory and Executive Order Reviews

    This final rule establishes tolerances under FFDCA section 408(d) 
in response to a petition submitted to the Agency. The Office of 
Management and

[[Page 72226]]

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 FFDCA section 408(d), 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 FFDCA section 408(n)(4). 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) (2 U.S.C. 1501 et seq.).
    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) (15 U.S.C. 272 note).

VII. Congressional Review Act

    Pursuant to the Congressional Review Act (5 U.S.C. 801 et seq.), 
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 
the rule in the Federal Register. This action 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: November 27, 2012.
G. Jeffrey Herndon,
Acting Director, Registration Division, Office of Pesticide Programs.

    Therefore, 40 CFR chapter I is amended as follows:


1. The authority citation for part 180 continues to read as follows:

    Authority: 21 U.S.C. 321(q), 346a and 371.

2. In Sec.  180.559, in paragraph (a), revise the introductory text; 
and in the table, revise the entry for ``Wheat, grain'' to read as 

Sec.  180.559  Clodinafop-propargyl; tolerances for residues.

    (a) General. Tolerances are established for clodinafop-propargyl, 
including its metabolites and degradates, in or on the commodities in 
the following table. Compliance with the tolerance levels specified in 
the following table is to be determined by measuring only clodinafop-
propargyl [(2R)-2-[4-[(5-chloro-3-fluoro-2-
pyridinyl)oxy]phenoxy]propanoic acid, 2-propynyl ester] and its 
metabolite clodinafop [(2R)-2-[4-[(5-chloro-3-fluoro-2- 
pyridinyl)oxy]phenoxy]propanoic acid].

                                                             Parts per
                        Commodity                             million
                                * * * * *
Wheat, grain............................................            0.02
                                * * * * *

* * * * *
[FR Doc. 2012-29248 Filed 12-4-12; 8:45 am]