[Federal Register Volume 61, Number 116 (Friday, June 14, 1996)]
[Rules and Regulations]
[Pages 30167-30170]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 96-15194]



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ENVIRONMENTAL PROTECTION AGENCY
40 CFR Part 180

RIN 2070-AB78
[PP 4F4278/R2239; FRL-5377-7]


Triflusulfuron Methyl; Pesticide Tolerance

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final Rule.

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SUMMARY: This document establishes time-limited tolerances for residues 
of the herbicide triflusulfuron methyl, methyl 2-[[[[[4-
(dimethylamino)-6-(2,2,2-trifluroroethoxy)-1,3,5-triazin-2-
yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, in or on the raw 
agricultural commodities sugar beet tops and sugar beet roots. Because 
additional time is needed for the petitioner to submit additional 
product chemistry data for an updated manufacturing process, the Agency 
is granting the tolerances for sugar beet root and top with a 3-year 
expiration date. E.I. duPont de Nemours Company requested these 
tolerances in a petition submitted to EPA pursuant to the Federal Food, 
Drug, and Cosmetic Act (FFDCA).
EFFECTIVE DATE: June 14, 1996.

ADDRESSES: Written objections and hearing requests, identified by the 
docket number, [PP PP 4F4278/R2239], 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 Office 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 docket 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 request 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 
must submitted as an ACSII file avoiding the use of special characters 
and any firm of encryption. Copies of objections and hearing requests 
will also be accepted on disks in Word Perfect in 5.1 file format or 
ASCII file format. All copies of objections and hearing requests in 
electronic hearing requests in electronic form must be identified by 
the docket number [PP 4F4278/R2239]. 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, Robert J. Taylor, Product 
Manager (PM 25), Registration Division (7505C), Office of Pesticide 
Programs, Environmental Protection Agency, 401 M St., SW, Washington, 
DC 20460. Office location and telephone number: Rm. 241, CM #2, 1921 
Jefferson Davis Hwy., Arlington, VA 22202, (703) 305-6027; e-mail: 
[email protected].
SUPPLEMENTARY INFORMATION: EPA issued a notice, published in the 
Federal Register of August 17, 1995 (60 FR 42884) (FRL-4963-7) which 
announced that E.I. DuPont de Nemours Co., Barley Mill Plaza, Walkers 
Mill Building 37, Post Office Box 80038, Wilmington, DE 19880-0038, had 
submitted a pesticide petition (PP 4F4278) which proposed to amend 40 
CFR part 180 by establishing a regulation to permit residues of the 
herbicide triflusulfuron methyl (methyl 2-[[[[[4-(dimethylamino)-6-
(trifluoroethoxy)-1,3.5-(triazin-2-yl]amino]carbonyl]amino] sulfonyl]-
3-methylbenzoate) in or on the raw agricultural commodities sugar beet 
root and sugar beet top at 0.05 ppm. No comments or request for 
referral to an advisory committee were received in response to this 
notice of filing.
    The scientific data submitted in the petitions and other relevant 
material have been evaluated. The toxicological data considered in 
support of the proposed tolerances are listed below.
    1. Several acute toxicology studies placing technical grade 
triflusulfuron methyl in toxicity Category III for acute dermal 
toxicity and primary eye irritation and toxicity Category IV for acute 
oral toxicity, acute inhalation toxicity and primary dermal irritation. 
Technical triflusulfuron methyl was not a skin sensitizer.
    2. An acute neurotoxicity screening battery with rats fed dosages 
of 500, 1,000 or 2,000 milligrams/kilograms/day (mg/kg/day) with a no-
observed-effect level (NOEL) of 2,000 mg/kg/day (limit dose).
    3. A 21-day dermal toxicity study with rabbits fed dosages of 50, 
300, or 1,000 mg/kg/day with a systemic toxicity NOEL equal to or 
greater than 1,000 mg/kg for males and females and a dermal toxicity 
NOEL equal to or greater than 1,000 mg/kg/day for males and females.
    4. A subchronic neurotoxicity study with rats fed dosages of 0, 
6.1, 46.1, 92.7, or 186.2 mg/kg/day (males) or 7.1, 51.6, 104.1 or 
205.2 mg/kg/day (females) with a NOEL of 92.7 mg/kg/day (males) and 7.1 
mg/kg/day (females) based on decreased body weight/body weight gain at 
the lowest observed effect level (LOEL) of 186.2 mg/kg/day (males) and 
51.6 mg/kg/day (females).
    5. A 1 year oral toxicity study with dogs fed dosages of 1.0, 26.9, 
111.6 mg/kg/day (males) and 1.2, 27.7, and 95.5 mg/kg/day (females) 
with a NOEL of 26.9 mg/kg/day (males) based on increases in alkaline 
phosphatase; liver weight, and incidence of minimal centrilobular 
hepatocellular hypertrophy at the LOEL of 111.6 (males) and a NOEL of 
27.7 mg/kg/day (females) based on increased liver weight and increased 
incidence of minimal centrilobular hepatocellular hypertrophy at the 
LOEL of 95.5 mg/kg/day (females).
    6. In an 18-month carcinogenicity study mice were fed dosages of 
1.37, 20.9, 349 and 1,024 mg/kg/day (males) and 1.86, 27.7, 488 and 
1,360 mg/kg/day (females). Male mice had statistically significant 
positive trends for hepatocellular adenomas and for combined adenoma/
carcinoma (driven entirely by adenomas) at 349 and 1,024

[[Page 30168]]

mg/kg/day. These increases were not significant in pair-wise 
comparisons with control groups and were determined not to be 
carcinogenic effects by the Carcinogenicity Peer Review Committee 
(CPRC).
    7. In the combined chronic toxicity/carcinogenicity study rats were 
fed dosages of 0, 0.406, 4.06, 30.6 and 64.5 mg/kg/day (males) and 0, 
0.546, 5.47, 41.5, and 87.7 mg/kg/day (females). Male rats had a 
significant increasing trend and significant differences in pair-wise 
comparisons of the 30.6 and 64.5 mg/kg/day dose groups with controls 
for interstitial cell ademonas. This effect was determined to be a 
carcinogenic effect by the CPRC. No carcinogenic effects were noted in 
females up to and including 87.7 mg/kg/day (highest dose tested (HDT)). 
The LOEL for chronic toxicity is 30.6 mg/kg/day (males) and 41.5 mg/kg/
day (females) based on decreased body weight and body weight gain, 
alterations in the hematology parameters (males predominately) and an 
increased incidence of interstitial cell hyperplasia in males. The NOEL 
for chronic toxicity is 4,06 mg/kg/day (males) and 5.47 mg/kg/day 
(females). This value is adjusted to the lowest concentration level of 
the chemical at this dosage (60%) resulting in NOELs 2.44 mg/kg/day 
(males) and 3.28 mg/kg/day (females).
    8. In a developmental study rats were fed dosages of 0, 30, 120, 
350, and 1,000 mg/kg/day with a developmental NOEL equal to or greater 
than 1,000 mg/kg/day (HDT) and a maternal toxicity NOEL of 120 mg/kg/
day with a LOEL of 350 mg/kg/day based on reduced body weight gain in 
the 350 and 1,000 mg/kg/day animals, reduced food consumption in the 
1,000 mg/kg/day animals and lower food efficiency in the 350 and 1,000 
mg/kg/day groups.
    9. In a developmental study rabbits were fed dosages of 0, 15, 90, 
270, and 800 mg/kg/day with a NOEL for developmental toxicity of 90 mg/
kg/day with a LOEL of 270 mg/kg/day based on the increase in abortions 
and a decrease in mean fetal body weight. The NOEL for maternal 
toxicity is 90 mg/kg/day with a LOEL of 270 mg/kg/day based on maternal 
death and abortions, an increase in clinical signs noted in the mid-
high and high dose groups, decreased food efficiency and increased post 
mortem finding describing gastrointestinal effects.
    10. In a two-generation rat reproduction study rats were fed 
dosages of 0, 0.588, 5.81, 44.0 and 89.5 mg/kg/day (males) and 0, 
0.764, 7.75, 58 and 115 mg/kg/day (females) with a reproductive 
toxicity NOEL equal to or greater than 89.5 and 115 mg/kg/day for males 
and females, respectively, based on the absence of reproductive effects 
in rats at the highest dose level. The NOEL for systemic toxicity was 
5.81 and 7.75 for males and females, respectively, based on decreased 
body weight/body weight gain and food efficiency in males and females, 
and decreased weights of offspring from the Fo generation on days 14 
and 21 post-partum at 44.0 and 58.0 mg/kg/day in males and females 
respectively.
    11. Mutagenicity data submitted for the parent compound, 
triflusulfuron methyl included a reverse mutation assay (Ames Test) 
which was negative at concentrations up to 1,000 g/plate, the 
highest level tested; a Salmonella typhimurium plate incorporation 
assay which was negative at concentration up to 3,000 g/plate, 
the highest level tested; and a CHO/HPRT assay which was negative at 
concentrations up to 2,000 mg/kg/day, the highest level tested. A 
chromosomal aberration/human lymphocyte assay was positive in the 
presence of metabolic activation at concentrations greater than or 
equal to 1,500 g/ml. A second chromosomal aberration/human 
lymphocyte assay was positive in the presence of metabolitic activation 
at concentrations of 2,000 g/ml. Results in the absence of 
metabolic activation were inconclusive for both chromosomal aberration 
studies. The mouse bone marrow micronucleus test was negative at doses 
up to 5,000 mg/kg, the highest dose level tested. In three Salmonella 
typhimurium plate incorporation assays metabolites of triflusulfuron 
methyl were negative up to 5,000 g/plate, the highest level 
tested.
    12. A series of in vivo and in vitro studies were conducted in male 
rats to investigate the mechanism by which triflusulfuron methyl 
induces Leydig cell tumors in the testes. The studies demonstrated that 
triflusulfuron methyl produces a dose dependent decrease in the 
aromatase activity in vitro. However, the effects of the chemical on 
the enzyme in vivo are not conclusive since no inhibition of activity 
at extremely high dose levels after a 2-week exposure period were 
observed. Further, the hypothesis that this effect is mediated by a 
chronic depression in estradiol altering the negative feedback 
mechanism for LH upon the Leydig cells of the testes has been suggested 
but not clearly demonstrated. A trend but not pairwise statistical 
significance has been shown for either the 750 or 1,500 ppm serum 
levels of testosterone or estradiol after 1 year of exposure. In 
addition, no elevation in serum levels of LH were noted at either dose 
level.
    The Carcinogenicity Peer Review Committee (CPRC) of Health Effects 
Division (HED) has evaluated the rat and mouse cancer studies on 
triflusulfuron methyl along with other short term toxicity studies, 
mutagenicity studies and structure activity relationships. The CPRC 
agreed that triflusulfuron methyl should be classified as a Group C-
possible human carcinogen and that for the purpose of risk 
characterization the Reference Dose (RfD) approach should be used for 
quantification of human risk.
    This decision was based on evidence of highly significant, dose-
related increase in the incidence of interstitial cell adenomas in the 
rat at two doses. Evidence of a hormonal basis for these tumors was 
suggestive, but not conclusive. There was some evidence of clastogenic 
activity for triflusulfuron methyl which needs further study. A DNA 
damage/repair test in germ cells (e.g. alkaline elution assay) is being 
requested to clarify this. The evidence from structurally related 
analogs was mixed, of 12 chemicals in this class (sulfonylureas), 
primisulfuron methyl, prosulfuron, and tribenuron methyl have been 
associated with carcinogenic activity in rodents. The RfD approach for 
risk quantification was chosen because the tumors (testicular 
interstitial cell) were benign.
    Based on an NOEL of 2.44 mg/kg bwt/day in the 2 year rat feeding 
study, and using a 100-fold safety factor, the reference dose RfD for 
triflusulfuron methyl is calculated to be 0.024 mg/kg bwt/day. The 
theoretical maximum residue contribution (TMRC) for these tolerances is 
0.000017 mg/kg/day which represents 0.069% of the RfD for the overall 
U. S. population. For U. S. subgroup population, children aged 1 to 6, 
the TMRC for these tolerances is 0.000041 which represents 0.17% of the 
RfD assuming residue levels are at established tolerances and that 100 
percent of the crop is treated. No other tolerances are published for 
triflusulfuron methyl.
    Data desirable but lacking for this chemical include additional 
product chemistry data on an updated manufacturing process and a DNA 
damage/repair test on germ cells. The Agency is granting the tolerances 
for sugar beet top and sugar beet root with a 3-year expiration date to 
allow the petitioner E.I. DuPont de Nemours Company to provide the 
additional product chemistry data.
    There are currently no regulations against the registration of this 
chemical for use on sugar beets. Even though triflusulfuron methyl is 
classified as a C-carcinogen, EPA believes that the

[[Page 30169]]

establishment of these tolerances will not pose an unreasonable risk to 
humans as a result of dietary exposure. The establishment of these 
tolerances utilize less than 1% (0.069%) of the RfD.
    The pesticide is useful for the purpose for which the tolerances 
are sought. The nature of the residue in plants and animals is 
adequately understood for the purposes of establishing these 
tolerances. Adequate analytical methodology (high pressure liquid 
chromatography (HPLC) using a C-8 or C-18 reverse phase analytical 
column) is available for enforcement purposes. Because of the long 
lead-time from establishing tolerances to publication, the enforcement 
methodology is being made available in the interim to anyone interested 
in pesticide enforcement. Request by mail from Calvin Furlow, Public 
Response Program Resources Branch, Field Operations Division (H7506C), 
Office of Pesticide Programs, Environmental Protection Agency, 401 M 
Street, SW., Washington DC 20460. Office location and telephone number: 
Rm. 1130A, CM #2, 1921 Jefferson Davis Hwy, Arlington, VA 22202. No 
detectable secondary residues are expected in milk; eggs; meat, fat, 
and meat byproducts of cattle, goats, hogs, horses, sheep, or poultry 
from this use.
    Based on the information and data considered, the Agency has 
determined that the tolerances established by amending 40 CFR part 180 
would protect the public health. Therefore, EPA is establishing the 
tolerances 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 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 each such issue, 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 shows the following: There is a 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 issue(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 4F4278/R2239] (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 docket 
number [PP 4F4278/R2239], 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 describes 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 a paper record maintained at 
the Virginia 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 review by the Office Of Management and Budget 
(OMB) and the requirements of the Executive Order. Under section 3(f), 
the order defines a ``significant regulatory action'' as an action that 
is likely to result in a rule (1) having an annual effect on 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 referred to as 
``economicallysignificant''); (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 the rights and obligation of 
recipients thereof; or (4) raising novel legal or policy issues arising 
out of legal mandates, the President`s priorities, or the principles 
set forth in this Executive Order. Pursuant to the terms of the 
Executive Order, EPA has determined that this rule is not 
``significant'' and is therefore not subject to OMB review.
    This action does not impose any enforceable duty, or contain any 
``unfunded mandates'' as described in Title II of the Unfunded Mandates 
Reform Act of 1995 (Pub. L. 104-4), or require prior consultation as 
specified by Executive Order 12875 (58 FR 58093, October 28, 1993), 
entitled Enhancing the Intergovernmental Partnership; or special 
consideration as required by Executive Order 12898 (59 FR 7629, 
February 16, 1994).
    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 that 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 Part 180

    Environmental protection, Administrative practice and procedure, 
Agricultural commodities, Food additive, Pesticides and pests, 
Reporting and recordkeeping requirements.

    Dated: June 3, 1996.

Daniel M. Barolo,
Director, Office of Pesticide Programs.
    Therefore, 40 CFR Part 180 is amended as follows:

PART 180--[AMENDED]

    1. The authority citation for part 180 continues to read as 
follows:
    Authority: 21 U.S.C. 346a and 371.



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    2. By adding Sec. 180.492 to subpart C to read as follows;


Sec. 180.492  Triflusulfuron Methyl; Tolerances for Residues

    Tolerances to expire as shown in the table below are established 
for residues of the herbicide, triflusulfuron methyl, methyl 2-[[[[[4-
(dimethylamino)-6-(2,2,2-trifluorothoxy)-1,3,5-triazin-2-
yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, in or on the raw 
agricultural commodities:

------------------------------------------------------------------------
                                      Parts per                         
             Commodity                 million        Expiration date   
------------------------------------------------------------------------
Sugar beet, root...................         0.05  June 14, 1999.        
Sugar beet, top....................         0.05  June 14, 1999.        
------------------------------------------------------------------------


[FR Doc. 96-15194 Filed 6-13-96; 8:45 am]
BILLING CODE 6560-50-F