[Federal Register Volume 84, Number 187 (Thursday, September 26, 2019)]
[Rules and Regulations]
[Pages 50761-50763]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2019-20525]



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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2018-0194; FRL-9998-87]


Cyclaniliprole; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes tolerances for residues of 
cyclaniliprole in or on multiple commodities that are identified and 
discussed later in this document. ISK Biosciences Corporation requested 
these tolerances under the Federal Food, Drug, and Cosmetic Act 
(FFDCA).

DATES: This regulation is effective September 26, 2019. Objections and 
requests for hearings must be received on or before November 25, 2019 
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-2018-0194, 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), West William Jefferson Clinton 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: Michael Goodis, Director, Registration 
Division (7505P), Office of Pesticide Programs, Environmental 
Protection Agency, 1200 Pennsylvania Ave. NW, Washington, DC 20460-
0001; main telephone number (703) 305-7090; email address: 
RDFRNotices@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. 
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://www.ecfr.gov/cgi-bin/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 Guidelines.''

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-2018-0194 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 
November 25, 2019. 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-2018-0194, 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 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 
20460-0001.
     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.html. 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 Tuesday, July 24, 2018 (83 FR 34968) 
(FRL-9980-31), 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 7F8651) by ISK Biosciences Corporation, 7470 Auburn Rd, 
Suite A, Concord, OH 44077. The petition requested that 40 CFR 180.694 
be amended by establishing tolerances for residues of the insecticide 
cyclaniliprole, 3-bromo-N-[2-bromo-4-chloro-6-[[(1-
cyclopropylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-
pyrazole-5-carboxamide, in or on the following commodities: Citrus 
fruit (crop group 10-10) at 0.5 parts per million (ppm); tuberous & 
corm vegetables (crop group 1C) at 0.01 ppm; and berry & small fruit 
(crop subgroup 13-07A, 13-07B, 13-07E except grape, and 13-07G) at 1.5 
ppm. That document referenced a summary of the petition prepared by ISK 
Biosciences Corporation, the registrant, which is available 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 is 
establishing tolerances that vary from the levels requested as allowed 
by section 408(d)(4)(A)(i) of FFDCA. The reason for these changes are 
explained in Unit IV.D.

III. Aggregate Risk Assessment and Determination of Safety

    Section 408(b)(2)(A)(i) of FFDCA allows EPA to establish a 
tolerance (the legal limit for a pesticide chemical residue in or on a 
food) only if EPA determines that the tolerance is ``safe.'' Section 
408(b)(2)(A)(ii) of FFDCA defines ``safe'' to mean that ``there is a 
reasonable certainty that no harm will result from aggregate exposure 
to the pesticide chemical residue, including all anticipated dietary 
exposures and all other exposures for which there is reliable 
information.'' This includes

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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 cyclaniliprole including 
exposure resulting from the tolerances established by this action. 
EPA's assessment of exposures and risks associated with cyclaniliprole 
is summarized as follows.
    EPA has evaluated the available toxicity data and considered its 
validity, completeness, and reliability as well as the relationship of 
the results of the studies to human risk. EPA has also considered 
available information concerning the variability of the sensitivities 
of major identifiable subgroups of consumers, including infants and 
children.
    No single or repeated dose study performed by any route of exposure 
produced an adverse effect following cyclaniliprole exposure at dose 
levels below, at, or above the limit dose (1,000 milligrams/kilogram/
day (mg/kg/day)). Although the oral toxicity studies in dogs were 
conducted at approximately a third of the limit dose, no adverse 
effects were seen. It is unlikely that cyclaniliprole would produce 
adverse liver effects, if tested at higher doses in dogs as a 
structurally related chemical, chlorantraniliprole, was tested up to 
the limit dose in dogs and did not demonstrate liver effects. There is 
no evidence that cyclaniliprole produces increased susceptibility with 
prenatal or postnatal exposures. Cyclaniliprole is considered not 
likely to be carcinogenic based on no increase in treatment-related 
tumor incidence in carcinogenicity studies in rats and mice and no 
genotoxicity.
    Specific information on the studies received for cyclaniliprole as 
well as the no-observed-adverse-effect-level (NOAEL) from the toxicity 
studies can be found at http://www.regulations.gov in document, 
``Cyclaniliprole: Human Health Risk Assessment for the Proposed New 
Uses on Bushberry Subgroup 13-07B; Caneberry Subgroup 13-07A; Citrus 
Fruit Crop Group 10-10; Low Growing Berry Subgroup 13-07G; Small Fruit 
Vine Climbing (except Grape) Subgroup 13-07E; and Tuberous and Corm 
Vegetables Crop Subgroup 1C.'', dated October 17, 2018 in docket ID 
number EPA-HQ-OPP-2018-0194.
    Based on the review of the available cyclaniliprole toxicological 
studies, no toxicity endpoints or points of departure were selected for 
risk assessment. Based on the toxicological profile of cyclaniliprole, 
EPA has concluded that the FFDCA requirements to retain an additional 
safety factor for protection of infants and children and to consider 
cumulative effects do not apply. Section 408(b)(2)(C) requires an 
additional tenfold margin of safety in the case of threshold risks, 
which cyclaniliprole does not present. Section 408(b)(2)(D)(v) requires 
consideration of information concerning cumulative effects of 
substances that have a common mechanism of toxicity, which 
cyclaniliprole does not have.
    There is a potential for exposure to cyclaniliprole residues via 
food and drinking water based on existing uses and the proposed uses 
for cyclaniliprole application directly to growing crops. These 
applications can also result in cyclaniliprole reaching surface and 
ground water, both of which can serve as sources of drinking water. 
Moreover, there are no proposed uses in residential settings; 
therefore, there are no anticipated residential exposures.
    Determination of safety. Based on the available data indicating a 
lack of adverse effects from exposure to cyclaniliprole, 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 cyclaniliprole.

IV. Other Considerations

A. Analytical Enforcement Methodology

    Adequate enforcement methods have been proposed for plants (Method 
JSM0269) and livestock commodities (Method JSM0277). For plants and 
livestock, cyclaniliprole residues are extracted using acetonitrile, 
cleaned up and analyzed by liquid chromatography with tandem mass 
spectrometry (LC-MS/MS). The validated limit of quantitation (LOQ) was 
0.01 ppm for plants and livestock commodities. All concurrent 
recoveries of cyclaniliprole at the fortification level of 0.01 ppm in 
the field trials and processing studies were within the acceptable 
range of 70-120%. The method is considered suitable for enforcement 
purposes. Adequate independent laboratory validation (ILV) and adequate 
radio-validation studies were conducted for the methods.

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 cyclaniliprole.

C. Revisions to Petitioned-For Tolerances

    Tolerances were requested for citrus fruit (crop group 10-10) at 
0.5 ppm; tuberous & corm vegetables (crop group 1C) at 0.01 ppm; and 
berry & small fruit (crop subgroup 13-07A, 13-07B, 13-07E except grape, 
and 13-07G) at 1.5 ppm.
    EPA considered commodity definitions and additional information 
provided by ISK Biosciences Corporation, including field trial residues 
that were adjusted by proportionality to reflect the proposed used 
pattern and used the Organization for Economic Cooperation and 
Development (OECD) statistical calculation procedures to determine the 
appropriate tolerance value which resulted in a different tolerance 
value for each of these subgroups than what the petitioner requested.
    EPA is establishing separate subgroup tolerances for fruit, citrus, 
group 10-10, in anticipation of the establishment of subgroup MRLs by 
Codex, rather than a single group MRL. For citrus fruit crop group 10-
10, EPA is establishing tolerances for orange subgroup 10-10A at 0.4 
ppm, lemon/lime subgroup 10-10B at 0.3 ppm, and grapefruit subgroup 10-
10C at 0.2 ppm. Based on processing studies, EPA is further 
establishing tolerances for fruit, citrus, group 10-10, oil at 30 ppm 
in accordance with its regulatory requirement to establish tolerances 
for processed commodities made necessary by the use of the

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pesticide on the commodities in the underlying crop group.
    For tuberous & corm vegetables (crop group 1C), EPA is establishing 
the tolerance at 0.01 ppm. Based on processing information and in 
accordance with 40 CFR 180.40(f), EPA is further establishing a 
tolerance for potato (wet peel) at 0.06 ppm.
    For the berries, the registrant proposed tolerances as berry and 
small fruit (Crop Subgroups 13-07A, 13-07B, 13-07E (except grape), and 
13-07G at 1.5 ppm. HED is recommending for individual crop subgroup 
tolerances, with the tolerance level based on the representative 
commodities for the specific subgroups. For the berry and small fruit 
subgroups, EPA is establishing the tolerance for caneberry subgroup 13-
07A at 0.8 ppm; bushberry subgroup 13-07B at 1.5 ppm; fruit, small vine 
climbing (except grape) subgroup 13-07E at 1 ppm; and berry, low 
growing, subgroup 13-07G at 0.4 ppm.

V. Conclusion

    Although the lack of toxicity supports a safety finding for an 
exemption from the requirement of tolerance for all crops, EPA is 
establishing tolerances for residues resulting from direct applications 
to certain commodities because the petitioner requested them for 
international trade purposes. Tolerances are established for residues 
of cyclaniliprole, 3-bromo-N-[2-bromo-4-chloro-6-[[(1- 
cyclopropylethyl)amino]carbonyl] phenyl]-1-(3-chloro-2-pyridinyl)-
1Hpyrazole-5-carboxamide in or on orange subgroup 10-10A at 0.4 ppm; 
lemon/lime subgroup 10-10B at 0.3 ppm; grapefruit subgroup 10-10C at 
0.2 ppm; and fruit, citrus, group 10-10, oil at 30 ppm; vegetable, 
tuberous and corm, subgroup 1C at 0.01 ppm; and potato, wet peel at 
0.06 ppm; caneberry subgroup 13-07A at 0.8 ppm; bushberry subgroup 13-
07B at 1.5 ppm; fruit, small, vine climbing, except grape, subgroup 13-
07E at 1 ppm; and berry, low growing, subgroup 13-07G at 0.4 ppm.

VI. Statutory and Executive Order Reviews

    This action establishes tolerances under FFDCA section 408(d) 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 action has been 
exempted from review under Executive Order 12866, this action 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), nor is it considered a 
regulatory action under Executive Order 13771, entitled ``Reducing 
Regulations and Controlling Regulatory Costs'' (82 FR 9339, February 3, 
2017). This action 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 action 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 action. In addition, this 
action does not impose any enforceable duty or contain any unfunded 
mandate as described under Title II of the Unfunded Mandates Reform Act 
(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 (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: September 10, 2019.
Michael Goodis,
Director, Registration Division, Office of Pesticide Programs.
    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.  180.694, add alphabetically the following commodities to 
the table in paragraph (a) to read as follows:


Sec.  180.694  Cyclaniliprole; tolerances for residues.

    (a) * * *

------------------------------------------------------------------------
                                                               Parts per
                          Commodity                             million
------------------------------------------------------------------------
 
                                * * * * *
Berry, low growing, subgroup 13-07G.........................         0.4
Bushberry subgroup 13-07B...................................         1.5
Caneberry subgroup 13-07A...................................         0.8
 
                                * * * * *
Fruit, citrus, group 10-10, oil.............................          30
 
                                * * * * *
Fruit, small, vine climbing, except grape, subgroup 13-07E..           1
 
                                * * * * *
Grapefruit subgroup 10-10C..................................         0.2
 
                                * * * * *
Lemon/lime subgroup 10-10B..................................         0.3
 
                                * * * * *
Orange subgroup 10-10A......................................         0.4
Potato, wet peel............................................        0.06
 
                                * * * * *
Vegetable, tuberous and corm, subgroup 1C...................        0.01
------------------------------------------------------------------------

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[FR Doc. 2019-20525 Filed 9-25-19; 8:45 am]
 BILLING CODE 6560-50-P


