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clethodim (Select) Pesticide Tolerances 6/95

[Federal Register: June 28, 1995 (Volume 60, Number 124)]
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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)-(<plus-minus>)-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: opp-docket@epamail.epa.gov. 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: 
                    miller.joanne@epamail.epa.gov.
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)-(<plus-minus>)-
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 weight 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 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-Docket@epamail.epa.gov
    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 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)-(<plus-minus>)-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)-(<plus-
minus>)-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:
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                                                              Parts per 
                         Commodity                             million  
------------------------------------------------------------------------
                                                                        
Onions (dry bulb)..........................................         0.20
Sugar beet, roots..........................................         0.20
Sugar beet, tops...........................................         0.50
                                                                        
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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)-(<plus-minus>)-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)-(<plus-
minus>)-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
                                                                        
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