Fomesafen - CAS No. 72178-02-0
Fomesafen sodium - CAS No. 108731-70-0
 
 

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Abstracts
Fomesafen Adverse Effects
Fomesafen sodium Adverse Effects

ACTIVITY: Herbicide (Diphenyl ether)

CAS Name for Fomesafen: 5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide

Structure for Fomesafen:

Fomesafen
Adverse Effects
:

Blood
Body Weight Decrease
Bone
Cancer: Possible Human Carcinogen - LIVER
Liver
Stomach

Fomesafen, sodium
Adverse Effects:

Cancer: Possible Human Carcinogen - LIVER

 

 

Fomesafen
Environmental Effects
:

Phototoxic Pesticide.

Potential ground water contaminant

Fomesafen, sodium
Environmental Effects:

As of Dec 2003: No data available

 

Regulatory Information
(only comprehensive for the US)
Fomesafen Fomesafen, sodium
US EPA Registered: Yes Yes 
US EPA PC Code: 123802 123802 
California Chemical Code  - 5086 
US Tolerances: CFR 180.433 CFR 180.433 
US EPA Permit Date
and Registrant:
1987, ICI   -
European Commission:

Not allowed to be used as an active ingredient after July 25, 2003, with the following exceptions:

France - Soybean, bean
Italy - Soybean, bean, pea
UK - Pea, bean, lupin .

 --
Registered use in (includes only a limited list of countries)

Canada, Hungary, South Africa, Tanzania, UK, US

Canada:
Dry beans, Lima beans, Snap beans, Soybeans

US
US Maximum Residue Levels

In 2003, the US Code of Federal Regulations (CFR) listed both Fomesafen and the Sodium salt of fomesafen with a tolerance of 0.05 ppm on Soybean.

The 2004 CFR did not list Fomesafen, only the sodium salt.

US:
Soybean

Over the years EPA has granted several Emergency Exemptions for the use of "Fomesafen."

Other Information
Molecular Formula: C15H10Cl F3 N2O6S C15H10ClF3N2O6S Na  
Entry Year: 1977  -
Inventing Company: Zeneca  -
Manufacturers: Syngenta Zeneca, BASF 
Other Names: Flexstar
Reflex
Tornado
Twister
Typhoon
PP 021
Flexstar
FLEX
Reflex
Tornado
Twister
Typhoon
BAS 530 04
 
Of special interest:

PAN Data for Fomesafen
PAN Data for Fomesafen, sodium 

Also Fomesafen, sodium: PAN Bad Actor for Acute toxicity

EPA released the following documents on March 28, 2007 (for more documents, see the Federal Register entry below):
Fomesafen Summary Document. (45 pages)
EPA-HQ-OPP-2006-0239-0003

Fomesafen: HED Registration Review Problem Formulation Document (February 28, 2007). This document describes the scope of work necessary to support the registration review. (8 pages) EPA-HQ-OPP-2006-0239-0004

Human Health Documents for Registration Review

Fomesafen: HED Registration Review Problem Formulation Document (February 28, 2007). This document describes the scope of work necessary to support the registration review. (8 pages) EPA-HQ-OPP-2006-0239-0004

Fomesafen Sodium: Human Health Risk Assessment for a Proposal to Amend Use on Soybeans, and Proposals to Add Uses on Cotton, Dry Bean, and Snap Bean, PC Code: 123802, Petition Nos: 1E6228, 9F50568, 6E4653, DP Barcode D325797 (February 28, 2006). This document describes all the human health risks from the use of fomesafen. (59 pages) EPA-HQ-OPP-2006-0239-0005

6 EFED Problem Formulation for Fomesafen Registration Review (Transmittal Memo) (February 13, 2007). This is the transmittal memo for the ecological risk problem formulation. (1 page) EPA-HQ-OPP-2006-0239-0006

Registration Review – Ecological Risk Assessment Problem Formulation for Fomesafen This document describes the ecological risk problem formulation. (25 pages) EPA-HQ-OPP-2006-0239-0007

Ecological Risk Assessment for New Uses of Fomesafen on Cotton (DP 302766), Snap beans (DP 314014), and Dry Beans (DP 314112) (January 30, 2007) This is the transmittal memo for the Ecological Risk Assessment. (4 pages) EPA-HQ-OPP-2006-0239-0008

Ecological Risk Assessment for Use of Fomesafen on Cotton (DP302766), Snap Beans (DP314014) and Dry Beans (DP314112) (January 2006). This document describes the toxicity of fomesafen to animals and plants in the environment. (55 pages) EPA-HQ-OPP-2006-0239-0009

Material Safety Data Sheets & Labels
2005 - Schedule for Reregistration & Tolerance Reassessment (RED) is expected to be November 2005. Contact at EPA: Stephanie Plummer (703) 305-0076; plummer.stephanie@epa.gov . According to EPA:
Through the pesticide reregistration and tolerance reassessment programs, EPA is assessing risks and making risk management decisions for older pesticides. These decisions are summarized in documents known as REDs, IREDs, and TREDs. By making decisions according to the schedule below, EPA will meet its statutory deadlines for completing reregistration and tolerance reassessment.
Some of the decision dates presented in the schedule may change due to the dynamic nature of the review process. Any pesticide decisions that are not completed during the current fiscal year will be rescheduled for the following year. EPA is committed to meeting its reregistration and tolerance reassessment deadlines.
http://www.epa.gov/pesticides/reregistration/decision_schedule.htm
Fomesafen.  November 26, 2002 - European Commission: one of 320 pesticides to be withdrawn in July 2003. However, specific exemptions for continued use of Fomesafen have been allowed on Soybean, bean in France; Soybean, bean, pea in Italy; and Pea, bean, lupin in the U.K. "Some 320 substances used in plant protection products (PPPs) including insecticides, fungicides and herbicides are to be withdrawn from the market by 25 July 2003 as part of the European Commission's new approach to the evaluation of active substances in plant protection products. This aims to improve safeguards to ensure that all such products in use are safe for the environment and human health. Users, wholesalers and retailers of plant protection products will need to be aware of whether the products they use or sell are likely to be withdrawn, so as to prevent them being left with stocks of unusable material. Those concerned should contact their national authority to check the authorisation status for any particular product. The Regulation (n 2076/2002 of 20 November 2002), with the list of the 320 substances, has now been published in the Offical Journal. Ref: MIDDAY EXPRESS. News from the Press and Communication Service's midday briefing.  
TOXNET profile from Hazardous Substances Data Bank 
Novemer 21, 2001 - Fomesafen, Schedule No. 1288. Canada Food and Drug Regulations: Maximum Residue Limit of 0.05 ppm in Lima beans; approved by Canada's Pest Management Regulatory Agency (PMRA), of Health Canada 
March 7, 2001 - Phototoxic Pesticides: US EPA Memo Requesting Phototoxicity Study Protocol for Light-Dependent Peroxidizing Herbicides 

May 24, 2000 - Cancer Assessment Document. Evaluation of the Carcinogenic Potential of Diclofop-Methyl. (Second Review). Final Report. Cancer Assessment Review Committee, Health Effects Division, US EPA Office of Pesticide Programs. "There are eight diphenyl ethers that are structurally similar to diclofop-methyl. Of the chemicals, fomesafen sodium, haloxyfop-methyl (Verdict), oxyfluorfen, acifluorfen sodium, nitrofen, and lactofen were reviewed in the initial CPRC report. All of these chemicals induced liver adenomas and carcinomas in rats and/or mice..." Organofluorine pesticides highlighted in red 

US Map of Pesticide Use: 1992-1995 
October 2001- Fomesafen sodium. Glossary of Pesticide Chemicals. A listing of pesticides subject to analysis of residues in foods and feeds by the US Food and Drug Administration. 
Abstracts 
Fomesafen (CAS No. 72178-02-0). 2000 Toxic Release Inventory: Brief Summary. 

Rationale for US EPA to add Fomesafen (CAS No. 072178-02-0)
to the Toxic Release Inventory

Decreased plasma cholesterol and triglycerides and increased liver weights (reversible at 7 days post-treatment) were observed at 50 mg/kg/day (only dose tested) when administered in the diet of rats for 4 weeks. In a 90-day rat study, dietary administration of 5 mg/kg/day (LOEL) produced alterations in lipid metabolism and increases in liver weight. The NOEL was 0.25 mg/kg/day. In a 26-week dog study, dietary administration of 25 mg/kg/day (LOEL) produced alterations in lipid metabolism and liver changes (changes not defined). The NOEL was 1 mg/ kg/day. Liver toxicity (increased liver masses, discolored hepatocytes, and pigmented Kupffer cells) was observed in a 2-year rat feeding study at 50 mg/kg/day (LOEL). The NOEL was 5 mg/kg/day. Metabolism studies have shown that fomesafen accumulates in the liver. EPA believes that there is sufficient evidence for listing fomesafen on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(B) based on the available hepatic toxicity data for this chemical.
Ref: USEPA/OPP. Support Document for the Addition of Chemicals from Federal Insecticide, Fungicide, Rodenticide Act (FIFRA) Active Ingredients to EPCRA Section 313. U. S. Environmental Protection Agency, Washington, DC (1993). As cited by US EPA in: Federal Register: January 12, 1994. Part IV. 40 CFR Part 372. Addition of Certain Chemicals; Toxic Chemical Release Reporting; Community Right-to-Know; Proposed Rule.



US Federal Register

•• Note: Due to length, the following is a partial list. Click here to see full list of FR entries.

Published Date Docket Identification Number Details

September 12, 2007

EPA-HQ-OPP-2007-0097

Tolerance Actions. FINAL RULE. EPA is inceasing the following tolerances for fomesafen from 0.025 to 0.05 ppm in order to harmonize with the Canadian MRLs in support of North American Free Trade Agreement (NAFTA) (see June 2007 proposal):

Bean, dry - 0.05 ppm
Bean, snap, succulent - 0.05 ppm

June 6, 2007 EPA-HQ-OPP-2007-0097

Proposed Tolerance Action. EPA is proposing to modify certain tolerances for fomesafen.

-- Currently, the tolerance in 40 CFR 180.433(a) for residues of fomesafen in/on bean, dry and bean, snap, succulent are each 0.025 ppm (May 3, 2006 (71 FR 25945) (FRL-8062-6). The Canadian
MRL is 0.05 ppm bean, dry and bean, snap, succulent. EPA proposes increasing the tolerances in 40 CFR 180.433(a) for residues of fomesafen in/on bean, dry and bean, snap, succulent from 0.025 to 0.05 ppm in order to harmonize with the Canadian MRLs in support of North American Free Trade Agreement (NAFTA). The Agency determined that the increased tolerances are safe; i.e., there is a reasonable certainty that no harm will result from aggregate exposure to the pesticide chemical residue.

-- A RED for fomesafen was not needed because it was registered after November 1, 1984 and not subject to reregistration eligibility, and its tolerances were reassessed prior to completion of a TRED, such that a RED for fomesafen was no longer needed because EPA made a safety finding which reassessed its tolerances according to FQPA standards.

Commodity Current Tolerance Proposed Tolerance
bean, dry 0.025 ppm 0.05 ppm
bean, snap, succulent 0.025 ppm 0.05 ppm
March 28, 2007 EPA-HQ-OPP-2006-0239

Pesticide Registration Review; New Docket Opened for Review and Comment. 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 fomesafen. Comments must be received on or before June 26, 2007.

Fomesafen Summary Document. (45 pages)
EPA-HQ-OPP-2006-0239-0003
Human Health Documents for Registration Review
Fomesafen: HED Registration Review Problem Formulation Document (February 28, 2007). This document describes the scope of work necessary to support the registration review. (8 pages) EPA-HQ-OPP-2006-0239-0004
Fomesafen Sodium: Human Health Risk Assessment for a Proposal to Amend Use on Soybeans, and Proposals to Add Uses on Cotton, Dry Bean, and Snap Bean, PC Code: 123802, Petition Nos: 1E6228, 9F50568, 6E4653, DP Barcode D325797 (February 28, 2006).
This document describes all the human health risks from the use of fomesafen. (59 pages)
EPA-HQ-OPP-2006-0239-0005
6 EFED Problem Formulation for Fomesafen Registration Review (Transmittal Memo) (February 13, 2007).
This is the transmittal memo for the ecological risk problem formulation. (1 page)
EPA-HQ-OPP-2006-0239-0006
Registration Review – Ecological Risk Assessment Problem Formulation for Fomesafen
This document describes the ecological risk problem formulation. (25 pages)
EPA-HQ-OPP-2006-0239-0007
Ecological Risk Assessment for New Uses of Fomesafen on Cotton (DP 302766), Snap beans (DP 314014), and Dry Beans (DP 314112) (January 30, 2007)
This is the transmittal memo for the Ecological Risk Assessment. (4 pages)
EPA-HQ-OPP-2006-0239-0008
Ecological Risk Assessment for Use of Fomesafen on Cotton (DP302766), Snap Beans (DP314014) and Dry Beans (DP314112) (January 2006).
This document describes the toxicity of fomesafen to animals and plants in the environment. (55 pages)
EPA-HQ-OPP-2006-0239-0009
Appendices for the EFED Ecological Risk Assessment (ERA) for new uses of fomesafen on cotton, snap beans, dry beans
Appendix A – Environmental Fate Studies. (5 pages)
EPA-HQ-OPP-2006-0239-0010
Appendix B – PRZM EXAMS Output. (11 pages)
EPA-HQ-OPP-2006-0239-0011
Appendix C - TREX Output, (2 pages)
EPA-HQ-OPP-2006-0239-0012

Appendix D - TerrPlant Output.
EPA-HQ-OPP-2006-0239-0013
Use docket search at the Federal Register. See pieces of this document here and here

Appendix E - Ecological Effects Data. (12 pages)
EPA-HQ-OPP-2006-0239-0014
Appendix F - EIIS Output. (2 pages)
EPA-HQ-OPP-2006-0239-0015
Appendix G - RQ Method and LOCs. (2 pages)
EPA-HQ-OPP-2006-0239-0016
Appendix H-1 – Endangered and Threatened Species. (26 pages)
EPA-HQ-OPP-2006-0239-0017
Appendix H-2 – ES Exclusion Chart. (1 page)
EPA-HQ-OPP-2006-0239-0018
Use and Usage Information for Registration Review
Fomesafen Screening-Level Usage Analysis (SLUA) (November 24, 2006)
This document provides the available estimates of pesticide usage data for fomesafen that is used on agricultural crops in the United States. (4 pages)
EPA-HQ-OPP-2006-0239-0019
Appendix A (November 22, 2006)
This table list the food/feed and non-food/non-feed uses eligible for reregistration. (1 page)
EPA-HQ-OPP-2006-0239-0020
Tolerance Salt of Fomesafen Summary Report
This document list the tolerances established for fomesafen. (1 page)
EPA-HQ-OPP-2006-0239-0021
Fomesafen Registrations
This document lists the pending and active registrations for fomesafen. (7 pages)
EPA-HQ-OPP-2006-0239-0022
Incident Reports for Fomesafen
Review of Fomesafen Incident Reports
This document reports poisoning incident data on the active ingredient Fomesafen. (4 pages)
EPA-HQ-OPP-2006-0239-0023
Ecological Incident Summary for Registration Review Snapshot. (1 page)
EPA-HQ-OPP-2006-0239-0024
Incident Report (Part A) (November 15, 2006). (3 pages)
EPA-HQ-OPP-2006-0239-0025
August 25, 2006 EPA-HQ-OPP-2006-0659 Pesticide Emergency Exemptions; Agency Decisions and State and Federal Agency Crisis Declarations
-- Fomesafen on snap or dry beans in Arkansa, Delaware, Indiana, Maine, Maryland, Michigan, Minnesota, Missouri, Oklahoma
June 7, 2006 EPA-HQ-OPP- 2006-0387

Pesticide Emergency Exemptions; Agency Decisions and State and
Federal Agency Crisis Declarations
.

-- New York: EPA authorized the use of fomesafen on dry and snap beans to control broadleaf weeds; June 1, 2006 to August 30, 2006.
-- Pennsylvania: Specific: EPA authorized the use of fomesafen on snap beans to control broadleaf weeds; June 1, 2006 to August 30, 2006.

May 3, 2006 EPA-HQ-OPP-2006-0073 IR-4 and Syngenta Crop Protection. Pesticide tolerance. FINAL RULE.
-- Bean, dry at 0.025 ppm
-- Bean, snap, succulent at 0.025 ppm
-- Cotton, gin byproducts at 0.025 ppm
-- Cotton, undelinted seed at 0.025ppm
-- Soybean at 0.05 ppm
March 1, 2006

EPA-HQ-OPP-2006-0073

and

Pesticide petition numbers (PP)

1E6228, 6E4653, and 9F5068

IR-4 & SYNGENTA. New Tolerance. PPs 1E6228, 6E4653, and 9F5068. Interregional Research Project No. 4 (IR-4) and Syngenta Crop Protection, Inc. proposes to establish tolerances for residues of the herbicide sodium salt of fomesafen in or on food commodities

PP# Commodity PPM
PP 1E6228 dry beans 0.025
PP 6E4653 snap beans
9F5068 cotton seed and cotton gin byproducts

An analytical method using chemical derivatization followed by gas chromatography (GC) with Nitrogen-Phosphorus detection (NPD) has been developed and validated for residues of fomesafen in snap/dry beans, cotton seed and cotton gin byproducts, as well as for other crops. After homogenization, the samples are extracted with acidified acetonitrile. After addition of water and additional acid, the extract was submitted to liquid/liquid partition. The residue is transferred to dichloromethane followed by acetone and derivatized with iodomethane in the presence of anhydrous potassium carbonate. A silica gel column cleanup is done with dichloromethane:hexane as the eluent. The final extract is transferred to toluene and analyzed by GC/NPD. The limit of quantitation is 0.025 ppm.

 
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