Triflumizole
CAS Nos. 68694-11-1 and 99387-89-0
US Federal Register
 
 

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Abstracts

ACTIVITY: Fungicide (azole)

Synonyms for Triflumizole [BSI:ISO] - CAS No. 68694-11-1
• (E)-4-Chloro-alpha,alpha,alpha-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine
• 1-(1-((4-Chloro-2-(trifluoromethyl)phenyl)imino)-2-propoxyethyl)-1H-imidazole
• 4-Chloro-alpha,alpha,alpha-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine

Structure for CAS No. 99387-89-0 Structure for CAS No. 68694-11-1


US Federal Register

Date Published Docket Identification Number Details
June 27, 2007 EPA-HQ-OPP-2007-0312

IR-4. Pesticide Petition. PP 7E7183. Proposal to establish a tolerance for residues of the fungicide triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound in or on food commodity

leafy Brassica (subgroup 5B)

This subgroup includes 8 commodities.
broccoli raab • cabbage, chinese bok choy • collards • kale • mizuna • mustard greens • mustard spinach • rape greens

20.0 ppm

The analytical method is suitable for analyzing crops for residues of triflumizole and its aniline
containing metabolites at the proposed tolerance levels. The analytical method has been independently validated. Residue levels of triflumizole are converted to FA-1-1 by acidic and alkaline reflux, followed by distillation. Residues are then extracted and subjected to solid phase extraction (SPE) purification. Detection and quantitation are conducted by a GC equipped with nitrogen phosphorus detector, electron capture detector or mass spectrometry detection. The LOQ of the method has been determined at 0.05 ppm for the combined residues of triflumizole and FA-1-1 in mustard greens. The enforcement methodology has been submitted to the Food and Drug Administration (FDA) for publication in the PAM II.

March 28, 2007 EPA-HQ-OPP-2006-0115

Pesticide Registration Review; New Docket Opened for Review and Comment. As directed by FIFRA section 3(g), EPA is periodically reviewing pesticide registrations to assure that they continue to satisfy the FIFRA standard for registration--that is, they can still be used without unreasonable adverse effects on human health or the environment. The implementing regulations establishing the procedures for registration review appear at 40 CFR part 155. A pesticide's registration review begins when the Agency establishes a docket for the pesticide's registration review case and opens the docket for public review and comment. At present, EPA is opening registration review for triflumizole. Comments must be received on or before June 26, 2007.

DOCUMENTS IN FEDERAL REGISTER DOCKET

Triflumizole Summary Document including Preliminary Work Plan Document (51 pages)
EPA-HQ-OPP-2006-0115-0003

List of Products Containing Triflumizole Pesticide Products Registered Under Section 3 of FIFRA (1 page)
EPA-HQ-OPP-2006-0115-0004
HEALTH EFFECTS DOCUMENTS
Review of Triflumizole Incidents Reports. August 15, 2006 (3 pages)
EPA-HQ-OPP-2006-0115-0005
Section 18 Specific Exemption for the Use of Triflumizole on Parsley, Dandelion, Swiss Chard, Collards, Kale, Kohlrabi, Mustard Greens, Chinese Napa Cabbage, Broccoli, Cilantro, and Turnip Greens in Texas. March 1, 2006. (12 pages)
EPA-HQ-OPP-2006-0115-0006
Triflumizole – Exposure/Risk Assessment for the FIFRA Section 18 Use of Triflumizole on Leafy Green Vegetable in Texas. February 1, 2006. (10 pages)
EPA-HQ-OPP-2006-0115-0007
Request for Permanent Tolerance for Residues of Triflumizole in/on Imported Greenhouse-Grown Tomatoes and Section 18 Specific Exemption for the Use of Triflumizole on Turnip Greens in Texas. May 26, 2005. (12 pages)
EPA-HQ-OPP-2006-0115-0008
Section 18 Specific Exemptions for the Use of Triflumizole on parsley, Dandelion, Swiss Chard, Collards, Kale, Kohlrabi, Mustard Greens, Chinese Napa Cabbage, Broccoli, and Cilantro. January 28, 2005. (14 pages)
EPA-HQ-OPP-2006-0115-0009
Triflumizole – Waiver Request for 28-Day Inhalation Study September 23, 2004. (3 pages)
EPA-HQ-OPP-2006-0115-0010
Triflumizole – Amendment to: Human Exposure and Risk Assessment for Proposed New Uses on Cherries, Hazelnuts, Cucurbits, Strawberries, Outdoor Ornamentals, and Institutional, Recreational and Residential Landscapes. April 26, 2002. (15 pages)
EPA-HQ-OPP-2006-0115-0011
Triflumizole in/on Strawberries, Cucurbit Vegetables, Cherries, and Hazelnuts. April 25, 2002. (44 pages)
EPA-HQ-OPP-2006-0115-0012
Minutes of 9/17/03 Chem SAC Meeting. 1/20/04. Render Food/Non-Food use Decision on the Proposed Use of Procure 50WS Fungicide to Treat Pineapple Seed Pieces. January 20, 2003. (1 page)
EPA-HQ-OPP-2006-0115-0013
HED SOP 2002.01 Standard Operating Procedure – Waiver Criteria for Multiple-Exposure Inhalation Toxicity Studies August 15, 2002. (7 pages)
EPA-HQ-OPP-2006-0115-0014
Triflumizole – Revised Report of the Hazard Identifiaction assessment Review committee. March 19, 2002. (30 pages)
EPA-HQ-OPP-2006-0115-0015
Triflumizole – Report of the FQPA Safety Factor Committee. March 21, 2002. (9 pages)
EPA-HQ-OPP-2006-0115-0016
Triflumizole. Issues to be Presented to the Health Effects Division (HED) Metabolism Assessment Review Committee (MARC) Meeting on 2/26/2002. February 26, 2002. (24 pages)
EPA-HQ-OPP-2006-0115-0017
ECOLOGICAL FATE & EFFECTS DOCUMENTS
Section 3 Request for Uses of Triflumizole on Foliage for Filberts. February 7, 2006. (130 pages)
EPA-HQ-OPP-2006-0115-0018
Tier 1 Drinking Water Assessment for Use of Triflumizole on Filberts. January 5, 2006. (8 pages)
EPA-HQ-OPP-2006-0115-0019
Tier 1 Estimated Drinking Water Concentrations for Triflumizole including Degradates. March 13, 2002. (14 pages)
EPA-HQ-OPP-2006-0115-0020
Section 3 Request for Use of Triflumizole (Chemical #128879) on Cherries, Strawberries, Cucurbits, and Ornamentals. May 21, 2001. (44 pages)
EPA-HQ-OPP-2006-0115-0021
Triflumizole Screening Level Estimated of Agricultural Uses March 29, 2006. (2 pages)
EPA-HQ-OPP-2006-0115-0022
Triflumizole Appendix A. October 26, 2006. (3 pages)
EPA-HQ-OPP-2006-0115-0023
August 23, 2006 EPA-HQ-OPP-2006-0461 Pesticide tolerance. FINAL RULE.
This regulation establishes time-limited tolerances for combined residues of triflumizole in or on turnip, greens. Additionally, this regulation increases the tolerance levels and extends time-limited tolerances for Chinese Napa cabbage, collards, coriander leaves (cilantro), kale, kohlrabi, mustard greens and parsley. Further, this regulation extends time-limited tolerances for broccoli, dandelion and Swiss chard.
Commodity
PPM
Expiration date
Broccoli
1.0
12/31/09
Cabbage, chinese, napa
20
12/31/09
Collards
20
12/31/09
Coriander, leaves
20
12/31/09
Dandelion, leaves
7.0
12/31/09
Kale
20
12/31/09
Kohlrabi
20
12/31/09
Mustard, greens
20
12/31/09
Parsley, leaves
20
12/31/09
Swiss chard
7.0
12/31/09
Turnip, greens
20
12/31/09
March 15, 2006 EPA-HQ-OPP-2006-0103

IR-4. Pesticide Tolerance. FINAL RULE. (Pesticide Petition 3E6535).
This regulation establishes a tolerance for combined residues of triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound in or on filberts at 0.05 ppm.

-- A summary of the toxicological endpoints for triflumizole used for human risk assessment is discussed in Unit VI.A. of the final rule published in the Federal Register - SEE BELOW - April 8, 2005.

-- Specific information on the studies received and the nature of the toxic effects caused by triflumizole as well as the no observed adverse effect level (NOAEL) and the lowest observed adverse effect level (LOAEL) from the toxicity studies published in the Federal Register - SEE BELOW - June 12, 2002.

Jan 18, 2006 EPA-HQ-OPP-
2005-0547
IR-4. Amendment to Existing Tolerance. PP 3E6535.
IR-4, 681 U.S. Highway #1 South, North Brunswick, NJ 08902, proposes to amend 40 CFR 180.476 by establishing tolerances for the combined residues of the fungicide triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety in or on the food commodity filberts at 0.05 parts per million (ppm). The analytical method is suitable for analyzing crops for residues of triflumizole and its aniline containing metabolites at the proposed tolerance levels. The analytical method has been independently validated. Residue levels of triflumizole are converted to FA-1-1 by acidic and alkaline reflux, followed by distillation. Residues are then extracted and subjected to SPE purification. Detection and quantitation are conducted by a gas chromatography equipped with nitrogen phosphorus detector, electron capture detector or mass spectrometry detector. The limit of quantitation of the method has been determined at 0.05 ppm for the combined residues of triflumizole and FA-1-1 in filberts. The enforcement methodology has been submitted to the Food and Drug Administration for publication in the Pesticide Analytical Manual, Vol. II (PAM II).
April 8, 2005 OPP-2005-0054

Pesticide Tolerances for Emergency Exemptions in TEXAS. FINAL RULE.
EPA, on its own initiative, in accordance with sections 408(e) and 408 (l)(6) of the Federal Food, Drug, and Cosmetic Act (FFDCA), 21 U.S.C. 346a, is establishing time-limited tolerances for combined residues of the fungicide triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound, in or on the following commodities.
Texas has declared a crisis exemption under FIFRA section 18 for the use of triflumizole in or on:

Commodity Parts per
million
Expiration/
revocation date
 
Broccoli 1.0 6/30/08
Cabbage, chinese, napa 9.0 6/30/08
Collards 9.0 6/30/08
Coriander, leaves (cilantro) 9.0 6/30/08
Dandelion, leaves 7.0 6/30/08
Kale 9.0 6/30/08
Kohlrabi 9.0 6/30/08
Mustard greens 9.0 6/30/08
Parsley, leaves 9.0 6/30/08
Swiss chard 7.0 6/30/08

Although these tolerances will expire and are revoked on June 30, 2008, under section 408(l)(5) of the FFDCA, residues of the pesticide not in excess of the amounts specified in the tolerances remaining in or on these commodities after that date will not be unlawful, provided the pesticide is applied in a manner that was lawful under FIFRA, and the residues do not exceed a level that was authorized by these tolerances at the time of that application.

In the Agency's previous triflumizole human health risk assessment, the following toxicity studies were determined to be data gaps:
• A 28-day rat inhalation study Guideline Number (GLN) 870.3465)),
• acute rat neurotoxicity study (GLN 870.6200), and
• subchronic rat neurotoxicity study (GLN 870.6200).

As acceptable acute and sub-chronic neurotoxicity studies have been submitted, the Agency has determined that the 3x UFDB should be removed from the acute and chronic RfDs. In addition, the FQPA SFC recommended a special FQPA SF [safety factor] be reduced to 1x. The Agency has re-evaluated the quality of the exposure and hazard data; and, based on these data, concluded that the special FQPA SF remain at 1x.

Conditions
The petitioner should submit adequate limited field rotational crop data on wheat at plant-back intervals longer than 120 days. Alternatively, the petitioner has the option of submitting a full set of residue field trials on all intended rotational crops other than leafy and root vegetables.

Excerpts from Table 1: Summary of Toxicological Dose and Endpoints for Triflumizole for Use in Human Risk Assessment:

Acute Dietary (females 13-50 years of age).
Developmental Toxicity Study - Rat
Developmental LOAEL = 35 mg/kg/day based on decreased numbers of viable fetuses,
increased dead or resorbed fetuses, increased numbers of late resorptions, decreased fetal body weight, and increased incidences of cervical ribs.

Acute Dietary (general U.S. population) (including infant and children).
Acute Neurotoxicity Study - Rat
LOAEL = 100 mg/kg/day based on functional observational battery findings (neuromuscular impairment) and decreased locomotor activity.

Chronic Dietary (all populations).
Multi-generation Reproduction Study - Rat
Reproductive LOAEL = 3.5 mg/kg/day based on increased gestation length in dams of the F3a interval.

Short-Term Oral (1-30 days) (Residential).
Multi-generation Reproduction Study - Rat
Reproductive LOAEL = 3.5 mg/kg/day based on increased gestation length in dams of the F3a interval.

Intermediate-Term Oral (1-6 months) (Residential).
Multi-generation Reproduction Study - Rat
LOAEL = 21 mg/kg/day, based on decreased body weight gain in pups during lactation and decreased body weight and body weight gain in parental animals.

Short-Term Dermal (1-30 days) (Occupational/Residential).
Multi-generation Reproduction Study - Rat
LOAEL = 21 mg/kg/day, based on decreased body weight gain in pups during lactation.

Intermediate- and Long-Term Dermal (1- 6 months and 6 month or longer) (Occupational/Residential).
Multi-generation Reproduction Study - Rat
LOAEL = 3.5 mg/kg/day based on increased gestation length in the dams of the F3a interval.

Short-Term Inhalation (1-30 days) (Occupational/Residential).
Multi-generation Reproduction Study - Rat
LOAEL = 21 mg/kg/day, based on decreased body weight gain in pups during lactation.

Intermediate- and Long-Term Inhalation (1-6 months and 6 month or longer)
(Occupational/Residential).
Multi-generation Reproduction Study - Rat
LOAEL = 3.5 mg/kg/day based on increased gestation length in the dams of the F3a interval.

Feb 23, 2005 OPP-2005-0037 Pesticide Emergency Exemptions.
Texas Department of Agriculture
Crisis: On December 21, 2004, for the use of triflumizole on parsley, dandelion, Swiss chard, collards, kale, kohlrabi, mustard greens, napa cabbage, and cilantro to control powdery mildew. This program is expected to end on October 1, 2005.

Feb 10, 2005

OPP-2005-0025

Removal of Expired Time-limited Tolerances for Emergency Exemptions. FINAL RULE.
The time-limited tolerance for filbert is being removed from Sec. 180.476 because it expired on June 30, 2004.
Aug 23, 2002 OPP-2002-0183

Pesticide Tolerance for Emergency Exemption; in or on Filbert at 0.05 ppm - for the state of Oregon only. FINAL RULE. Refer to the June 12, 2002 Federal Register document for a detailed discussion of the aggregate risk assessments and determination of safety. EPA relies upon that risk assessment and the findings made in the Federal Register document in support of this action - see excerpts below. This tolerance will expire and is revoked on June 30, 2004.

June 12, 2002 OPP-2002-0063

UNIROYAL -Pesticide Tolerance. FINAL RULE. This regulation establishes tolerances for the combined residues of triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound in or on cucurbit Group 9 vegetables (0.5 ppm), strawberries (2 ppm), sweet cherries (1.5 ppm) , and tart cherries (1.5 ppm).
-- 90-Day oral NOAEL = Males: toxicity rodents 15.3 mg/kg/day; (rat) Females: 17.2 mg/ kg/day LOAEL = Males: 176.5 mg/kg/day; Females: 217.9 mg/ kg/day based on increased kidney and liver weights and the accumulation of fat droplets in the liver.
-- Prenatal Maternal developmental in NOAEL = 10 mg/kg/ rodents (rat) day LOAEL = 35 mg/kg/ day based on decreased body weight gain and food consumption, and increased placental, spleen and liverweights. Developmental NOAEL = 10 mg/kg/ day LOAEL = 35 mg/kg/ day based on decreased numbers of viable fetuses, increased dead or resorbed fetuses, increased numbers of late resorptions, decreased fetal body weight, and increased incidences of cervical ribs.
-- Prenatal Maternal developmental in NOAEL = 50 mg/kg/ nonrodents day (rabbit) LOAEL = 100 mg/kg/ day based on decreased body weight gains, food consumption, and placental weights. Developmental NOAEL = 50 mg/kg/ day LOAEL = 100 mg/kg/ day based on decreased 24-hour survival, decreased placental weights, and increased fetal and litter incidences of lumbar ribs.
-- Reproduction and Parental/Systemic fertility effects NOAEL = 8.5 mg/kg/ (rat) day LOAEL = 21 mg/kg/ day based on decreased body weight and overall body weight gain, increased relative liver weights, and increased mortality in females. Reproductive NOAEL = not identified LOAEL = 3.5 mg/kg/ day based on increased gestation length in P. Offspring NOAEL = 8.5 mg/kg/ day LOAEL = 21 mg/kg/ day based on decreased pup body weight,survival indices, and litter sizes and a slight increased incidence of hydronephrosis in F1a pups.
-- Reproduction and Parental/Systemic fertility effects NOAEL = 8.5 mg/kg/ (rat) day LOAEL = not established Reproductive NOAEL = 1.5 mg/kg/ day LOAEL = 3.5 mg/kg/ day based on based on increased gestation length in dams of the F3a interval. Offspring NOAEL = 3.5 mg/kg/ day LOAEL = 8.5 mg/kg/ day based on decreased pup weights,survival indices, and litter sizes in both F3 litters, reduced litter size in the F1a litter, increased total-litter mortality in the F3a litter, and developmental effects in theF1b and F2b progeny.
-- Chronic toxicity NOAEL = Males: nonrodents (dog) 10.00 mg/kg/day; Females: 10.69 mg/ kg/day LOAEL = Males: 34.10 mg/kg/day; Females: 35.17 mg/ kg/day based on increased alkaline phosphatase activity and a mild, macrocytic anemia in males, increased absolute and relative liver weights in both sexes, and on macroscopic findings in the liver of both sexes.
-- Carcinogenicity NOAEL = Males: (mouse) 16.2 mg/kg/day; Females: 21.7 mg/ kg/day LOAEL = Males: 67.4 mg/kg/day; Females: 86.1 mg/ kg/day based on microscopic lesions of the liver. No evidence of carcinogenicity

Nov 14, 2001 OPP-181082
  • Denial of requests for Pesticide Emergency Exemptions. EPA denied the following:
  • Idaho: On June 26, 2001, EPA denied the use of triflumizole on sweet cherries to control powdery mildew. This request was denied because the claim of resistance to registered alternatives was not fully substantiated.
  • Oregon: On February 1, 2001, EPA denied the use of triflumizole on hazelnut to control Eastern Filbert Blight (EFB). This request was denied because the submission did not meet the criteria for an urgent, non-routine situation based on the availability of an effective alternative, tebuconazole, available under a FIFRA section 18 exemption.
  • Oregon: On February 1, 2001, EPA denied the use of triflumizole on hazelnut to control Eastern Filbert Blight (EFB). This request was denied because the submission did not meet the criteria for an urgent, non-routine situation based on the availability of an effective alternative, tebuconazole, available under a FIFRA section 18 exemption.
  • Utah: On June 26, 2001, EPA denied the use of triflumizole on cherries to control powdery mildew. This request was denied because the claim of resistance to registered alternatives was not fully substantiated.
  • Washington: On June 26, 2001, EPA denied the use of triflumizole on sweet cherries to control powdery mildew. This request was denied because the claim of resistance to registered alternatives was not fully substantiated.
July 6, 2001 PF-1031

UNIROYAL - Petition to establish a tolerance for residues in or on strawberries at 2.0 ppm, the cucurbit crop group at 0.5 ppm, and cherries at 2.0 ppm.

Oct 3, 1997 - FINAL NA Cut Roses. Exception Decisions to Early Entry Prohibition, Worker Protection Standard; Technical Amendment. - FINAL RULE. See Federal Register of Oct 30, 1996 below.
Oct 3, 1997- Proposed OPP-250121 Cut Roses. Pesticide Worker Protection Standard; Administrative Exception for Cut-Rose Hand Harvesting; Administrative Decision. Proposed Rule.
Augt 4, 1997 OPP-300523 Pesticides Subject to Tolerance Reassessment.
July 16, 1997 NA UNIROYAL - Request to voluntarily cancel certain pesticide registration for:
Terraguard 50W
. EPA Reg. No. 000400 OR-91-000
Oct 30, 1996 OPP-300164I Cut-Roses; Request for Exception to Worker Protection Standard's Prohibition of Early Entry into Pesticide-Treated Areas to Harvest Roses by Hand Cutting.
Nov 16, 1994 PP 6F3372
and
FAP 6H5497/R2085

UNIROYAL - Pesticide Tolerances and Feed Additive Regulations.- FINAL RULE. Tolerances are established for the combined residues of the fungicide triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety in or on the following raw agricultural commodities: Apples and Pears at 0.5 ppm; Grapes at 2.5 ppm; Meat and fat of horses, hogs, goats, sheep, and poultry at 0.05 ppm.

Tolerances are established for the combined residues of the fungicide triflumizole and its metabolites containing the 4-chloro-2-trifluoromethylaniline moiety, calculated as the parent compound, in or on the following processed feed commodities when present therein as a result of application to growing crops: Grape pomace at 15 ppm; Raisin waste at 10 ppm; Apple pomace at 2 ppm.

1993 NA

UNIROYAL - Petition to Establish Tolerances for the combined residues of the fungicide in or on the following commodities: apples at 0.1 ppm; cattle, fat, meat and meat byproducts (mbyp) at 0.05 ppm; grapes at 0.3 ppm; hogs, fat, meat and mbyp at 0.05 ppm; milk at 0.05 ppm; pears at 0.1 ppm; and poultry, eggs, fat, meat and mbyp at 0.05 ppm. Note. The Fed. Reg. does not have online access to its 1993 edition. This notice comes from the Pesticide Managment Education Program at Cornell U.

 
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