Oxyfluorfen
CAS No. 42874-03-3
 
 

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Adverse Effects
Abstracts

ACTIVITY: Herbicide (Diphenyl ether)

CAS Name: 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene

Structure:

Adverse Effects:

Anemia
Blood
Body Weight Decrease
Bone
Brain

Cancer: Possible Human Carcinogen - LIVER
Endocrine: Adrenal
Endocrine: Pituitary
Endocrine: Thymus
Endocrine: Thyroid
Kidney
Liver
Spleen

Environmental Effects:

Highly Toxic to fish

Bioaccumulation Potential

Phototoxic. Oxyfluorfen may pose risks to animals not conveyed by standard guideline toxicity studies because its mode of action suggests it may be more toxic in the presence of light (phototoxic)

Sub-chronic and chronic risks to terrestrial birds and mammals present a serious concern. These toxic effects may be manifested as reproductive, developmental, and hemolytic consequences.

Contamination Incidents:

Aug 2000: Fifteen Mile Creek near the Dalles Dam, Oregon. Truck carring 20,000 pounds crashed into bridge spilling herbicide into creek yards from where it enters the Columbia River.

March 1996: Madera County, CA. Aerial drift onto 90-100 acres of almonds. Estimated damage $520,000 to $760,000.

May 1996: Desha County, AR. Aerial drift onto 160 acres of rice.

March 1996: Kern County, CA. Aerial drift onto 10 acres of oranges.

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes 
US EPA PC Codes: 111601 
288600
California Chemical Code 1973 
US Tolerances: CFR 180.381 
FDA LMS Code: 713 
US EPA Permit Date
and Registrant:
1979, Rohm & Haas 
Registered use in
(includes only a limited list of countries)

Australia, Canada, Hungary, India, New Zealand, Philippines, Portugal, South Africa, US 

Australia:
Grape

US Maximum Residue Levels permitted in food commodities
Permitted in or on 91 food commodities, including:
Artichoke, Avocado, Banana (inc Plantains), Blackberry, Broccoli, Cabbage, Cattle, Cauliflower, Chickpea seed, Cocoa bean, Coffee bean, Corn, Cotton, Egg, Feijjoa, Fig, Fruit (Pome & Stone group), Goat, Grape, Guava, Hog, Horse, Horseradish, Kiwifruit, Milk, Peppermint, Spearmint, Nuts (tree), Olive, Onion, Papaya, Persimmon, Pistachio, Pomegranate, Poultry, Raspberry, Sheep, Soybean, Taro, Walnut
 
Other Information
Molecular Formula: C15H11Cl F3 NO4 
Entry Year: 1974 
Inventing Company: Rohm & Haas  
Manufacturers: Rohm & Haas 
Other Names: Goal, Koltar, RH-2915 
Manufacture sites: ISRAEL:
Agan Chemical,

Ashdod 77102


US:
Rohm & Haas, Philadelphia Pennsylvania 19137
 
Of special interest:
PAN Data 
Material Safety Data Sheets & Labels
Jan 23, 2006: Conservation Group Moves for Court Order Restricting Use of 66 Pesticides in Core Red-Legged Frog Habitat.
San Francisco, Calif. – The Center for Biological Diversity (CBD) in a legal motion today asked a U.S. District Court to protect the threatened California red-legged frog (Rana aurora draytonii) from 66 of the most toxic and persistent pesticides authorized for use in California, by creating pesticide-free buffer zones around the frog’s core habitat and by requiring consumer hazard warnings so that all Californians may learn how to protect frogs. [Oxyfluorfen was one of the 66 pesticides.]
In response to a lawsuit filed by CBD against the U.S. Environmental Protection Agency (EPA) in April of 2002, the District Court found in September of 2005 that the EPA violated the Endangered Species Act (ESA) by registering pesticides for use without considering how they might impact the continued existence of the red-legged frog. The motion for “injunctive relief” delivered today asks the court to protect the frog from pesticides in or adjacent to aquatic frog habitat designated as core recovery areas, until the EPA completes a formal consultation with the U.S. Fish and Wildlife Service (USFWS) on the impacts of the pesticides on red-legged frogs, as required under the ESA... CBD is asking the Court to impose a three-year schedule for the EPA to determine whether the 66 pesticides may affect the red-legged frog and to complete formal consultations with USFWS to ensure the pesticides are not jeopardizing the frog or contributing to its decline. To minimize harm to frogs during the consultation process, the motion asks for an injunction on use of the pesticides around aquatic features and upland habitats within the frog’s core recovery areas, as designated by USFWS in the agency’s Recovery Plan for the California Red-legged Frog. This injunction would also apply buffer areas for terrestrial and aerial pesticide applications, affecting approximately 7 percent of the current range of the frog and less than 1 percent of the area of California. CBD is also requesting that the EPA conduct monitoring for pesticides in three of the recovery areas to determine whether the buffers are effectively protecting the frog, inform pesticide users about the injunction, and post point-of-sale notifications warning consumers about harmful effects these pesticides may have on the frog...
June 30, 2005: Re-evaluation of Oxyfluorfen. PACR2005-03. Canada Pest Management Regulatory Agency.
October 30, 2002: US EPA's Reregistration Eligibility Decision (RED) document 
Oct 30, 2002 - RED Fact Sheet (short). US EPA.
October 30, 2002: Background documents for US EPA's RED at:
- We list a few of these documents below:

• Jan 11, 2002 - Overview of Oxyfluorfen Risk Assessment

• Dec 18, 2001 - Revised Human Health Risk Assessment.

• Dec 11, 2001 - Revised Environmental Fate and Effects Division Preliminary Risk Assessment for the Oxyfluorfen RED

• Aug 8, 2001 - Toxicology chapter for RED document.

• March 7, 2001 - Phototoxic Pesticides: 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
 
August 22, 2000 - Spill in Washington. Initial report (as of 8/22/00) - 8,000 to 16,000 pounds of the herbicide Oxyfluorfen Cause: A semi-trailer truck carrying the herbicide crashed and caught fire.
US Map of Pesticide Use - 1992-1995 
2000 Toxic Release Inventory. Brief Summary.
Abstracts 
One of 8 fluorinated pesticides used to cultivate grapes in Australia. 
April 2000 - Food and Drug Administration Pesticide Residue Monitoring. - Table 3. Pesticides detectable by methods used in 1999 regulatory monitoring. 
October 2001 - Glossary of Pesticide Chemicals. A listing of pesticides subject to analysis of residues in foods and feeds by the US Food and Drug Administration.  

Rationale for US EPA to add Oxyfluorfen to the Toxic Release Inventory

Oxyfluorfen is a phenoxyphenyl-type herbicide. Several chronic oral toxicity studies suggest that oxyfluorfen may be hepatotoxic. Hepatic effects (e.g. increased absolute liver weight, necrosis, regeneration, and hyperplastic nodules) were observed in mice fed diets containing greater than 3 mg/kg/day oxyfluorfen for 20 months (the NOEL was 0.3 mg/kg/day). Based on these findings, an oral RfD value of 0.003 mg/kg/ day was derived. This study was supported by other chronic feeding studies that demonstrated increases in liver weight, alkaline phosphatase activity, and bile pigmented hepatocytes (the LOEL was 15 mg/kg/day; the NOEL was 2.5 mg/kg/day) in dogs, and minimal hypertrophy of centrilobular hepatocytes (the LOEL was 40 mg/kg/day; the NOEL was 2 mg/kg/day) in rats. EPA believes that there is sufficient evidence for listing oxyfluorfen on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(B) based on the hepatotoxic effects of this chemical.

The estimated chronic MATC values for fish and daphnids are 9 ppb and 20 ppb oxyfluorfen, respectively. The estimated log Kow is 6.1. EPA believes that there is sufficient evidence for listing oxyfluorfen on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(C) based on the environmental toxicity data and potential for bioaccumulation for this chemical.

Ref: USEPA/OPPT. Support Document for the Health and Ecological Toxicity Review of TRI Expansion Chemicals. 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.


Use Profile

Oxyfluorfen is a diphenyl-ether herbicide used for broad spectrum pre- and post-emergent control of annual broadleaf and grassy weeds in a variety of tree fruit, nut, vine, and field crops. The largest agricultural markets in terms of total pounds active ingedient are wine grapes and almonds. There are also non-agricultural ornamental and forestry uses. Oxyfluorfen is also used for weed control in landscapes, patios, driveways, and similar areas in residential sites.
Ref: Oct 30, 2002 - RED Fact Sheet. US EPA.

From 1992 to 1997 the use of oxyfluorfen increased by 54%, from an estimated 458,000 pounds active ingredient in 1992 to an estimated 705,000 lbs active ingredient in 1997 (Gianessi and Silvers, 2000). Much of this increase was driven by changes in usage on four agricultural crops. An estimated 2% of broccoli acreage in California was treated with oxyfluorfen in 1992; that estimate increased to 15% of broccoli acreage in California in 1997. Treated acreage of Texas onions increased from 15% to 100% and treated acreage of California onions increased from 55% to 67% between 1992 to 1997. Much of this increase in treated broccoli and onion acreage was due to the end of production of DCPA (a pre-emergence herbicide). An estimated 12% of cotton acreage in Louisiana was treated with oxyfluorfen in 1992; that estimate increased to 20% of cotton acreage in Louisiana in 1997. This change was attributed to the adoption of planting a "stale" seedbed (similar to conventional planting, except a “burndown” herbicide, such as oxyfluorfen, is required to remove weeds). Use on California pistachio acreage increased from an estimated 44% to 62% between 1992 and 1997. During this time interval, the total acreage in pistachios increased by 78%, thus resulting in a large total poundage increase in oxyfluorfen usage.
Ref: US EPA. Revised Environmental Fate and Effects Division Preliminary Risk - December 11, 2001.


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 19, 2007 EPA-HQ-OPP-2007-0036

Tolerance Actions. FINAL RULE. EPA is modifying certain tolerances for the herbicide oxyfluorfen and is establishing new tolerances.

• SEE all tolerances

New tolerances are:
-- Corn, pop, grain - 0.05 ppm
-- Peppermint, tops - 0.05 ppm
-- Spearmint, tops - 0.05 ppm

New Emergency Exemptions are:
Grass, forage - 0.05 ppm
Grass, hay - 0.05 ppm
Grass, seed screenings - 0.05 ppm

Revised tolerances are:
Hog, fat - from 0.05 to 0.01 ppm
Hog, meat byproducts - from 0.05 to 0.01 ppm
Hog, meat - from 0.05 to 0.01 ppm
Horse, fat - from 0.05 to 0.01 ppm
Horse, meat byproducts - from 0.05 to 0.01 ppm
Horse, meat - from 0.05 to 0.01 ppm
Milk - from 0.05 to 0.01 ppm
Poultry, fat - from 0.05 to 0.2 ppm
Poultry, meat byproducts - from 0.05 to
0.01 ppm
Poultry, meat - from 0.05 to 0.01 ppm
Sheep, fat - from 0.05 to 0.01 ppm
Sheep, meat byproducts - from 0.05 to 0.01 ppm
Sheep, meat - from 0.05 to 0.01 ppm

EPA is revising the commodity terminology in 40 CFR 180.381(a) from cocoa bean, dried bean to cacao bean, dried bean..

May 2, 2007 EPA-HQ-OPP-2007-0036

Proposed Tolerance Action. EPA is proposing to modify certain tolerances for the herbicide oxyfluorfen and is proposing to establish new tolerances. The regulatory actions proposed in this document are in follow-up to the Agency's reregistration program under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), and tolerance reassessment program under the Federal Food, Drug, and Cosmetic Act (FFDCA) section 408(q). EPA has issued a post-FQPA REDs for oxyfluorfen.

Comments must be received on or before July 2, 2007.

Based on available data that showed residues of oxyfluorfen as high as 0.03 ppm in or on mint hay, EPA determined that the tolerance on mint hay (peppermint and spearmint) should be decreased from 0.1 to 0.05 ppm. Therefore, the Agency is proposing in 40 CFR 180.381(a) to revise the commodity terminology for mint hay into separate tolerances on peppermint, tops and spearmint, tops and decrease each tolerance to 0.05 ppm.

Based on available exaggerated (5x to 7x MTDB) cattle feeding data that showed residues of oxyfluorfen as high as < 0.003 ppm in milk, 0.007 ppm in fat, < 0.003 ppm in meat, < 0.003 ppm in kidney, and < 0.003 ppm in liver, EPA expected residues below the LOQ (0.01 ppm) in milk, fat, meat, and meat byproducts at the 1x MTDB for cattle. The Agency determined that the tolerances on milk and the fat, meat and meat byproducts of cattle, goats, hogs, horses, and sheep should be set at the LOQ and decreased from 0.05 to 0.01 ppm. Therefore, EPA is proposing in 40 CFR 180.381(a) to decrease the tolerances on milk; cattle, fat; cattle, meat; cattle, meat byproducts; goat, fat; goat, meat; goat, meat byproducts; hog, fat; hog, meat; hog, meat byproducts; horse, fat; horse, meat; horse, meat byproducts; sheep, fat; sheep, meat; and sheep, meat byproducts to 0.01 ppm.

Based on available exaggerated (2.0x MTDB) poultry feeding data that showed residues of oxyfluorfen as high as 0.024 ppm in eggs, 0.163 ppm in fat, 0.004 ppm in meat, and 0.006 ppm in liver, EPA expected residues of 0.012 ppm in egg, 0.082 ppm in fat, 0.002 ppm in meat, and 0.003 ppm in liver at the 1x MTDB for poultry. The Agency determined that the tolerances should be decreased on egg from 0.05 to 0.03 ppm, meat and meat byproducts from 0.05 to 0.01 ppm, and increased on fat from 0.05 to 0.2 ppm. Therefore, EPA is proposing in 40 CFR 180.381(a) to decrease the tolerances on egg to 0.03 ppm, poultry, meat to 0.01 ppm, poultry, meat byproducts to 0.01 ppm, and increase the tolerance on poultry, fat to 0.2 ppm. The Agency determined that the increased tolerance is safe; i.e., there is a reasonable certainty that no harm will result from aggregate exposure to the pesticide chemical residue. Based on available data that showed oxyfluorfen residues from use of oxyfluorfen on grass grown for seed in Oregon and Washington were not detectable (< 0.03 ppm) in or on grass forage, hay, and seed screenings, EPA determined that the reassessed animal commodity tolerances are adequate to cover any residue contribution from regional registration uses of oxyfluorfen on grasses grown for seed and tolerances should be established on grass forage, hay, and seed screenings at 0.05 ppm. Therefore, the Agency is proposing to establish tolerances in 40 CFR 180.381(c) on grass, forage; grass, hay; and grass, seed screenings; each at 0.05 ppm.

In addition, EPA is proposing to revise commodity terminology in 40 CFR 180.381 to conform to current Agency practice as follows:

``banana (including plantain)'' to ``banana''
``coffee, bean'' to ``coffee, bean, green;'' `
`corn, grain'' to ``corn, field, grain'' and ``corn, pop, grain;''
``onion, dry bulb'' to ``onion, bulb;''
``taro, corm and leaves'' to ``taro, corm'' and ``taro, leaves.

Moreover, it should be noted that use of oxyfluorfen on plantains is covered by the existing tolerance at 0.05 ppm for banana under 40 CFR 180.1(g), and there is no need to establish a separate tolerance on plantains at 0.05 ppm. Also, because use of oxyfluorfen on garlic is covered by the existing tolerance at 0.05 ppm for onion bulb under 40 CFR 180.1(g), there is no need to establish a separate tolerance on garlic at 0.05 ppm as had been recommended in the RED.

April 13, 2007 EPA-HQ-OPP-2007-0005

Notice of Receipt of Requests to Voluntarily Cancel Certain Pesticide Registrations.

Registration No. Product Name Registrant
062719 AZ-00-0001 Goal 2XL Herbicide Dow Agrosciences LLC 9330 Zionsville Rd 308/2E,
Indianapolis IN 46268-1054
September 1, 2006 EPA-HQ-OPP-2006-0702 Request for Public Comment on Proposed Stipulated Injunction Involving 66 Pesticides and the California Red-legged Frog. Center for Biological Diversity vs EPA .
June 28, 2006 EPA-HQ-OPP-2006-0084 Notice of Receipt of Requests to Voluntarily Cancel Certain Pesticide Registrations.
Registration numbers Product Name Registrant

062719 OR-96-0037
062719 OR-97-0008
062719 WA-96-0034
062719 WA-97-0024

Goal (r) 2XL Herbicide Dow Agrosciences LLC
9330 Zionsville Rd 308/2E,
Indianapolis, IN 462681054
 
 
August 17, 2005 OPP-2005-0222

Requests to Voluntarily Cancel Certain Pesticide Registrations.

Registration no. Product Name Registrants Requesting Voluntary Cancellation
000524-00520 Mon 78095 Herbicide Monsanto Co, Agent For:
Monsanto Co., 1300 I Street,
Nw, Suite 450 E., Washingt, DC
20005.
062719 OR-00-0028 Goal 2XL Herrbicide Dow Agrosciences LLC, 9330
Zionsville Rd 308/2e225,
Indianapol, IN 462681054. 
062719 OR-96-0036 Goal (r) 2XL Herbicide same
062719 WA-96-0033 Goal (r) 2XL Herbicide same
062719 WA-97-0013 Goal (r) 2XL Herbicide same
062719 WA-99-0035 Goal (r) 2XL Herbicide same
August 3, 2005 OPP-2005-0201

Cancellation of Pesticides for Non-payment of Year 2005 Registration Maintenance Fees.

Section 24(c) Registrations canceled for non-payment of the 2005
maintenance fee are shown in the following Table 1:

Table 1.--Section 24(c) Registrations Canceled for Non-Payment of Maintenance Fee

SLN no. Product Name
062719 CA-89-0012 Goal 1.6E Herbicide
062719 CA-95-0007 Goal 1.6E Herbicide
March 10, 2005 OPP-2005-0057 Requests to Voluntarily Cancel Certain Pesticide Registrations.
Unless a request is withdrawn by September 6, 2005, orders will be issued canceling these registrations. The Agency will consider withdrawal requests postmarked no later than September 6, 2005.
Chemical Name Registration No. Product Name Company Name and Address
Oxyfluorfen 062719 AZ-02-0003 Goal 2XL
Herbicide
Dow Agrosciences LLC, 9330
Zionsville Rd 308/2e225,
Indianapol, IN 462681054
Oxyfluorfen 062719 IN-96-0004 Goal (r) 2XL
Herbicide
same
Oxyfluorfen
062719 OR-00-0001 Goal 2XL
Herbicide
same
Oxyfluorfen
062719 SD-02-0002 Goal 2XL
Herbicide
same
Oxyfluorfen
062719 SD-02-0003 Goal 2XL
Herbicide
same
Oxyfluorfen
066222 OR-01-0026 Galigan 2E Makhteshim-Agan of North America Inc., 551 Fifth Ave.-
Ste 1100, New York, NY 10176
Oct 27, 2004 OPP-2004-0338 Cancellation of Pesticides for Non-payment of Year 2004 Registration Maintenance Fees.
Table 1.--Section 24(c) Registrations Canceled for Non-Payment of
Maintenance Fee
Name of Pesticide Product Name Registrant SLN No.
Oxyfluorfen Galigan 2E Makhteshim-Agan of North America Inc. 066222 OR-01-0025
Oxyfluorfen Galigan 2E Makhteshim-Agan of North America Inc. 066222 WA-01-0029
Feb 17, 2004 OPP-2004-0037

Availability of Court Orders in Washington Toxics Coalition v. EPA Litigation. The Order (with some exceptions) enjoins, vacates and sets aside EPA's authorization of certain pesticides' uses within 20 yards for ground applications and 100 yards for aerial applications, adjacent to salmon supporting waters in California, Oregon and Washington, effectively establishing buffer zones around those waters. This order applies to 38 pesticides, including the fluoridated
Diflubenzuron, Oxyfluorfen, Trifluralin.
The Court's January 22 Order, which carries an effective date of February 5, 2004, and other related materials, including the Court's previous Orders, are available at:
January 22, 2004
August 8, 2003
July 16, 2003
July 2, 2002

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

 
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