[Federal Register Volume 60, Number 124 (Wednesday, June 28, 1995)]
[Rules and Regulations]
[Pages 33358-33360]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 95-15579]
[[Page 33358]]
ENVIRONMENTAL PROTECTION AGENCY
40 CFR Parts 180 and 186
[PP 4F4340 and FAP 5H5722/R2146; FRL-4961-7]
RIN 2070-AB78
Clethodim; Pesticide Tolerances
AGENCY: Environmental Protection Agency (EPA).
ACTION: Final rule.
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SUMMARY: These regulations establish tolerances for the residues of the
herbicide clethodim [(E)-()-2-[1-[[(3-chloro-2-
propenyl)oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-
cyclohexen-1-one] and its metabolites containing the 5-(2-
ethylthiopropyl)-cyclohexen-3-one and 5-(2-ethylthiopropyl)-5-
hydroxycyclohexen-3-one moieties and their sulphoxides and sulphones,
expressed as clethodim, in or on the raw agricultural commodities sugar
beet roots at 0.20 ppm; sugar beet tops at 0.50 ppm; and onions (dry
bulb) at 0.20 ppm; and in or on the food additive commodity sugar beet
molasses at 2.0 ppm. Valent U.S.A. Corp. submitted petitions for these
regulations that establish maximum permissible levels for residues of
the herbicide in or on the commodities.
EFFECTIVE DATE: These regulations become effective June 28, 1995.
ADDRESSES: Written objections, identified by the document control
number, [PP 4F4340 and FAP 5H5722/R2146], may be submitted to: Hearing
Clerk (1900), Environmental Protection Agency, Rm. M3708, 401 M St.,
SW., Washington, DC 20460. Fees accompanying objections shall be
labeled ``Tolerance Petition Fees'' and forwarded to: EPA Headquarters
Accounting Operations Branch, OPP (Tolerance Fees), P.O. Box 360277M,
Pittsburgh, PA 15251. A copy of any objections and hearing requests
filed with the Hearing Clerk should be identified by the document
control number and submitted to: Public Response and Program Resources
Branch, Field Operations Division (7506C), Office of Pesticide
Programs, Environmental Protection Agency, 401 M St., SW., Washington,
DC 20460. In person, bring copy of objections and hearing requests to
Rm. 1132, CM #2, 1921 Jefferson Davis Hwy., Arlington, VA 22202.
A copy of objections and hearing requests filed with the Hearing
Clerk may also be submitted electronically by sending electronic mail
(e-mail) to: [email protected]. Copies of objections and
hearing requests must be submitted as an ASCII file avoiding the use of
special characters and any form of encryption. Copies of objections and
hearing requests will also be accepted on disks in WordPerfect in 5.1
file format or ASCII file format. All copies of objections and hearing
requests in electronic form must be identified by the docket number [PP
4F4370 and FAP 5H5722/R2146]. No Confidential Business Information
(CBI) should be submitted through e-mail. Electronic copies of
objections and hearing requests on this rule may be filed online at
many Federal Depository Libraries. Additional information on electronic
submissions can be found below in this document.
FOR FURTHER INFORMATION CONTACT: By mail: Joanne I. Miller, Product
Manager (PM-23), Registration Division (7505C), Environmental
Protection Agency, 401 M St., SW. Washington, DC 20460. Office location
and telephone number: Rm. 237, CM #2, 1921 Jefferson Davis Highway,
Arlington, VA 22202, (703)-305-7830; e-mail:
[email protected].
SUPPLEMENTARY INFORMATION: In the Federal Register of November 2, 1994
(59 FR 54906), EPA issued a notice announcing that Valent U.S.A. Corp.,
1333 North California Blvd., Walnut Creek, CA, had submitted a
pesticide petition (PP 4F4340) to EPA under section 408 of the Federal
Food, Drug, and Cosmetic Act (21 U.S.C. 346a), proposing to amend 40
CFR part 180 by establishing tolerances for residues of the herbicide
clethodim and its metabolites containing the 2-cyclohexen-1-one moiety
in or on sugar beet, roots, at 0.2 ppm, sugar beet, tops, 0.2 ppm, and
onion (dry bulb) at 0.5 ppm. On March 13, 1995, Valent subsequently
submitted a revision to PP 4F4340 to amend the proposed tolerances on
sugar beet, tops from 0.20 to 0.50 ppm and onions (dry bulb) from 0.50
to 0.20 ppm. In addition, EPA issued a notice, published in the Federal
Register of May 3, 1995 (60 FR 21816), which announced that Valent had
submitted a food additive petition (FAP 5H5722) to EPA under section
409 of the Federal Food, Drug, and Cosmetic Act (FFDCA) (21 U.S.C.
348), proposing to amend 40 CFR part 186 by establishing a regulation
to permit the residues of the herbicide clethodim [(E)-()-
2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-5-[2-(ethylthio)propyl]-
3-hydroxy-2-cyclohexen-1-one] and its metabolites containing the 5-(2-
ethylthiopropyl)cyclohexen-3-one and 5-(2-ethylthiopropyl)-5-
hydroxycyclohexen-3-one moieties and their sulphoxides and sulphones,
expressed as clethodim, in or on sugar beet molasses at 2.0 ppm.
There were no comments or requests for referral to an advisory
committee received in response to the notices of filing.
The data submitted in the petition and other relevant material have
been evaluated. The toxicology data described below were considered in
support of these tolerances and food additive regulations.
1. Several acute toxicology studies placing the technical-grade
herbicide in Toxicity Category III.
2. A 2-year rat chronic toxicity/carcinogenicity study found the
compound to be noncarcinogenic to rats under the conditions of the
study. The systemic no-observed-effect level (NOEL) was 500 ppm
(approximately 19 mg/kg/day), and the systemic lowest-observed-effect
level (LOEL) was 2,500 ppm (approximately 100 mg/kg/day) based on the
observed body wight gain, the increases in liver weights, and the
presence of centrilobular hepatic hypertrophy.
3. An 18-month mouse carcinogenicity study which showed the
compound to be noncarcinogenic to mice under the conditions of the
study. The systemic NOEL was 200 ppm (8 mg/kg/day), and the systemic
LOEL was 1,000 ppm (50 mg/kg/day) based on treatment-related effects on
survival, red cell mass, absolute and relative liver weights, and
microscopic findings in liver and lung.
4. A 1-year feeding study in dogs with a systemic NOEL of 1 mg/kg/
day in both sexes and an LOEL of 75 mg/kg/day based on increased
absolute and relative liver weights, and alteration and clinical
chemistry.
5. A developmental toxicity study in rats with a developmental and
maternal NOEL and LOEL of 100 and 350 mg/kg/day, respectively. The NOEL
and LOEL for developmental toxicity were based on reductions in fetal
body weight and increases in skeletal anomalies.
6. A developmental toxicity study in rabbits with a maternal
toxicity NOEL and LOEL of 25 and 100 mg/kg/day, respectively. Maternal
toxicity was manifested as clinical signs of toxicity and reduced
weight gain and food consumption during treatment. Developmental
toxicity was not observed, and therefore the developmental toxicity
NOEL was 300 mg/kg/day (HDT).
7. A two-generation reproduction study in the rat with parental
toxicity NOEL and LOEL of 500 and 2,500 ppm (51 and 263 mg/kg/day),
respectively, based on reductions in body weight in males, and
decreased food consumption [[Page 33359]] in both generations. The NOEL
for reproductive toxicity was 2,500 ppm (263 mg/kg/day, HDT).
8. A mutagenicity test with Salmonella Ames assay showed
nonmutagenicity in three strains. Clethodim imine sulfone was negative
for reverse gene mutation in Salmonella and E. coli exposed up to
10,000 ug/plate with or without activation. Clethodim was negative for
chromosomal damage in bone marrow cells of rats treated orally up to
toxic dose (1,500 mg/kg).
The Office of Pesticide Programs' Health Effects Division's
Carcinogenicity Peer Review Committee (CPRC) has classified clethodim
in Group E carcinogen (no evidence of carcinogenicity) under the
Agency's ``Guidelines for Carcinogen Risk Assessment,'' published in
the Federal Register of September 24, 1986 (51 FR 33992). In its
evaluation, CPRC gave consideration to the weight change in the 2-year
feeding study in rats and the 18-month feeding study in mice.
The Reference dose (RfD) is established at 0.01 mg/kg body weight/
day based on a NOEL of 1.0 mg/kg/body weight/day from the 1-year
feeding study in dogs and an uncertainty factor of 100. Using
anticipated residues and 100 percent crop treated, the Anticipated
Residue Contribution (ARC) from the current action is estimated at
0.00087 mg/kg/body weight/day for the general population, or 8.7
percent of the RfD for the general U.S. population. The ARC for the
most exposed subgroups is 0.002527 mg/kg body weight/day for nonnursing
infants (less than 1 year old) and 0.001776 mg/kg body weight/day for
children (1 to 6 years old), or 25.27 and 17.76 percent of the RfD,
respectively. Therefore, no appreciable risk is expected from chronic
dietary intake since the RfD is not exceeded for either the general
population or any subgroup.
The nature of the residue is adequately understood for the purposes
of the tolerance.
An adequate analytical method is available for enforcement
purposes. A common moiety analytical method for tolerance enforcement
(gas chromatography with a flame photometric detector in the sulfur
mode) was satisfactorily tested and is available. This method, however,
cannot distinguish between clethodim and sethoxydim, a closely related
herbicide with tolerances established under 40 CFR 180.412. A compound-
specific confirmatory method (HPLC with a UV detector) that can
distinguish between derivatives of clethodim and sethoxydim was
confirmed.
The enforcement methodology has been submitted to the Food and Drug
Administration for publication in the Pesticide Analytical Manual,
Vol.II (PAM II). Because of the long lead time for publication of the
method in PAM II, the analytical methodology is being made available in
the interim to anyone interested in pesticide enforcement when
requested for: Calvin Furlow, Public Response and Program Resources
Branch, Field Operations Division (7506C), Office of Pesticide
Programs, Environmental Protection Agency, 401 M St., SW., Washington,
DC 20460. Office location and telephone number: Rm. 1132, CM #2, 1921
Jefferson Davis Hwy., Arlington, VA 22202, (703)-305-5232.
The pesticide is considered useful for the purpose for which the
tolerances are sought, and the tolerances are capable of achieving the
intended physical or technical effect. There are currently no actions
pending against the registration of this chemical.
Based on the information and data considered, the Agency has
determined that the tolerances established by amending 40 CFR parts 180
and 186 will protect the public health and that use of the pesticide in
accordance with the terms of the proposed food additive tolerance will
be safe. Therefore, the tolerances are established as set forth below.
Any person adversely affected by this regulation may, within 30
days after publication of this document in the Federal Register, file
written objections to the regulation and may also request a hearing on
those objections. Objections and hearing requests must be filed with
the Hearing Clerk, at the address given above (40 CFR 178.20). A copy
of the objections and/or hearing requests filed with the Hearing Clerk
should be submitted to the OPP docket for this rulemaking. The
objections submitted must specify the provisions of the regulation
deemed objectionable and the grounds for the objections (40 CFR
178.25). Each objection must be accompanied by the fee prescribed by 40
CFR 180.33(i). If a hearing is requested, the objections must include a
statement of the factual issue(s) on which a hearing is requested, the
requestor's contentions on such issues, and a summary of any evidence
relied upon by the objector (40 CFR 178.27). A request for a hearing
will be granted if the Administrator determines that the material
submitted show the following: There is genuine and substantial issue of
fact; there is a reasonable possibility that available evidence
identified by the requestor would, if established, resolve one or more
of such issues in favor of the requestor, taking into account
uncontested claims or facts to the contrary; and resolution of the
factual issues(s) in the manner sought by the requestor would be
adequate to justify the action requested (40 CFR 178.32).
A record has been established for this rulemaking under docket
number [PP 4F4340 and FAP 5H5722/R2146] (including objections and
hearing requests submitted electronically as described below). A public
version of this record, including printed, paper versions of electronic
comments, which does not include any information claimed as CBI, is
available for inspection from 8 a.m. to 4:30 p.m., Monday through
Friday, excluding legal holidays. The public record is located in Room
1132 of the Public Response and Program Resources Branch, Field
Operations Division (7506C), Office of Pesticide Programs,
Environmental Protection Agency, Crystal Mall #2, 1921 Jefferson Davis
Highway, Arlington, VA.
Written objections and hearing requests, identified by the document
control number [PP 4F4340 and FAP 5H5722/R2146], may be submitted to
the Hearing Clerk (1900), Environmental Protection Agency, Rm. 3708,
401 M St., SW., Washington, DC 20460.
A copy of electronic objections and hearing requests filed with the
Hearing Clerk can be sent directly to EPA at:
opp-D[email protected]
A copy of electronic objections and hearing requests filed with the
Hearing Clerk must be submitted as an ASCII file avoiding the use of
special characters and any form of encryption.
The official record for this rulemaking, as well as the public
version, as described above will be kept in paper form. Accordingly,
EPA will transfer any objections and hearing requests received
electronically into printed, paper form as they are received and will
place the paper copies in the official rulemaking record which will
also include all objections and hearing requests submitted directly in
writing. The official rulemaking record is the paper record maintained
at the address in ``ADDRESSES'' at the beginning of this document.
Under Executive Order 12866 (58 FR 51735, October 4, 1993), the
Agency must determine whether the regulatory action is ``significant''
and therefore subject to all the requirements of the Executive Order
(i.e., regulatory Impact Analysis, review by the Office of Management
and Budget (OMB)). Under section 3(f), the order defines
``significant'' as those actions likely to lead to a rule (1) having an
annual effect [[Page 33360]] of the economy of $100 million or more, or
adversely and materially affecting a sector of the economy,
productivity, competition, jobs, the environment, public health or
safety, or State, local or tribal governments or communities (also
known as ``economically significant''); (2) creating serious
inconsistency or otherwise interfering with an action taken or planned
by another agency; (3) materially altering the budgetary impacts of
entitlement, grants, user fees, or loan programs; or (4) raising novel
legal or policy issues arising of legal mandates, the President's
priorities, or the principles set forth in the Executive Order.
Pursuant to the terms of this Executive Order, EPA has determined
that this rule is not ``significant'' and is therefore not subject to
OMB review.
Pursuant to the requirements of the Regulatory Flexibility Act
(Pub. L. 96-354, 94 Stat. 1164, 5 U.S.C. 601-612), the Administrator
has determined the regulations establishing new tolerances or raising
tolerance levels or establishing exemptions from tolerance requirements
do not have a significant economic impact on a substantial number of
small entities. A certification statement to this effect was published
in the Federal Register of May 4, 1981 (46 FR 24950).
List of subjects in 40 CFR Parts 180 and 186
Environmental protection, Administrative practice and procedure,
Agricultural commodities, Feed additives, Pesticides and pests,
Reporting and recordkeeping requirements.
Dated: June 9, 1995.
Peter Caulkins,
Acting Director, Registration Division, Office of Pesticide Programs.
Therefore, 40 CFR parts 180 and 186 are amended as follows:
PART 180--[AMENDED]
1. In part 180:
a. The authority citation for part 180 continues to read as
follows:
Authority: 21 U.S.C. 346a and 371.
b. In Sec. 180.458, by designating the existing text as paragraph
(a) and adding new paragraph (b), to read as follows:
Sec. 180.458 Clethodim ((E)-()-2-[1-[[(3-chloro-2-
propenyl)oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-
cyclohexen-1-one); tolerances for residues.
(a) * * *
(b) Tolerances are established for the herbicide clethodim [(E)-(
)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-5-[2-
(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one] and its metabolites
containing the 5-(2-ethylthiopropyl)cyclohexen-3-one and 5-(2-
ethylthiopropyl)-5-hydroxycyclohexen-3-one moieties and their
sulphoxides and sulphones, expressed as clethodim tolerance residues
for the following raw agricultural commodities:
------------------------------------------------------------------------
Parts per
Commodity million
------------------------------------------------------------------------
Onions (dry bulb).......................................... 0.20
Sugar beet, roots.......................................... 0.20
Sugar beet, tops........................................... 0.50
------------------------------------------------------------------------
PART 186--[AMENDED]
2. In part 186:
a. The authority citation for part 186 continues to read as
follows:
Authority: 21 U.S.C. 348.
b. In Sec. 186.1075, by revising the section heading, designating
the existing text as paragraph (a), and adding new paragraph (b), to
read as follows:
Sec. 186.1075 Clethodim ((E)-()-2-[1-[[(3-chloro-2-
propenyl)oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-
cyclohexen-1-one).
(a) * * *
(b) Tolerances are established for the herbicide clethodim [(E)-(
)-2-[1-[[(3-chloro-2-propenyl)oxy]imino]propyl]-5-
[2(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one] and its metabolites
containing the 5-(2-ethylthiopropyl)cyclohexen-3-one and 5-(2-
ethylthiopropyl)-5-hydroxycyclohexen-3-one moieties and their
sulphoxides and sulphones, expressed as clethodim tolerance residues
for the following feeds:
------------------------------------------------------------------------
Parts per
Commodity million
------------------------------------------------------------------------
Sugar beet, molasses....................................... 2.0
------------------------------------------------------------------------
[FR Doc. 95-15579 Filed 6-27-95; 8:45 am]
BILLING CODE 6560-50-F