Fluometuron
CAS No. 2164-17-2
 
 

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Adverse Effects
Abstracts

ACTIVITY: Herbicide (phenylurea)

CAS Name: N,N-dimethyl-N?-[3-(trifluoromethyl)phenyl]urea

Structure:

Adverse Effects:

Adverse Effects:
Ataxia
Blood
Body Weight Decrease
Bone
Brain
Cancer: Possible Human Carcinogen: Lung,
Lymphocytic lymphomas, (Liver?)
CNS
Endocrine: Pituitary
Endocrine: Testicular
Eye
Kidney
Leukemia
Liver
Lung
Reproductiv/Developmental
Spleen
Environmental

Contamination Incident:

July 2, 2004. Australia. Crash kills crops. Herbicide scattered over field of canola.

Environmental Effects:

Groundwater pollutant. The significant cancer risk contributors have been identified as drinking water (direct and indirect, all sources), and several rotational crops with wheat (flour), soybean (oil), and rice (white) having the highest contributions.

Acute risks to birds, mammals, and endangered species.

In its March 2005 reassessment, EPA noted that several key studies regarding risks to animals and fish have not been submitted by the registrant, Makhteshim-Agan.

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes 
US EPA PC Code: 035503 
California Chemical Code 166 
US Tolerances: CFR 180.229
CFR 186.3350
 
FDA LMS Code: 701 
Registered use in
(includes only a limited list of countries)

Australia, India, US
Africa: Burkina Faso, Cape Verde, Chad, Gambia, Guinea-Bissau, Mali, Mauritania, Niger, Senegal, South Africa, Tanzania
US Maximum Residue Levels permitted in food commodities

Cotton, undelinted seed

Other Information
Molecular Formula: C10H11 F3 N2O  
Entry Year:

1960 

Marketed in the US in 1960 (NTP, page 1)
First registered in the US in May 1974 by Ciba

Inventing Company: Ciba 
Manufacturers:

2005: Agan Chemical Manufactures, Ltd.

The US Agent for Agan is
Makhteshim-Agan of North America, Inc.

Previous manufacturer : Novartis 

Other Names: Approved for use in the US as of February 2005:
Meturon 4L, Meturon SODF, Cotoran@ 4L, Cotoran@ 80 DF, Fluometuron SOW, Fluometuron 80DF, Fluometuron 4L, Fluometuron + MSMA, Drexel CroakTMFluometuron + MSMA, Flo-Met 4L, Flo-Met 80DF, Cotoran@ + MSMA with Surfactant, Cotoran@ SOW, Cotoran@ SOW, Cotoran@ 4L, Cotoran@ DF, Cotoran@ Accu-Pak
See
Herbicide Products
Manufacture site:

CHINA: Wenzhou Zhenan Medicine Factory, No. 26 Tutian Road, Yangfushan Industry Zone, Wenzhou, Zhejiang 325003
ISRAEL: Agan Chemical, Ashdod
SWITZERLAND: formerly: Novartis, Monthey
SWITZERLAND: As of April 2003: Syngenta Crop Protection Monthey AG, Monthey
FRANCE: Rhone Poulenc, Le Pont de Claix
AUSTRIA: Nufarm, Linz
ITALY: Industria Prodotti Chemici, Novate Milanese
HUNGARY: EMV North-Hungarian Chemical Works Co., Sajobabony
 

Of special interest:
PAN Data 
Material Safety Data Sheets & Labels
2005 - Schedule for Reregistration & Tolerance Reassessment (RED) is expected to be September 2005. Contact at EPA: Kylie Rothwell (703) 308-8055; rothwell.kylie@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

July 2, 2004. Crash kills crops. Herbicide scattered over field of canola. By Sam Edmund, regional reporter. Herald Sun Melbourne (Australia).

TOXNET profile from Hazardous Substances Data Bank 
1994 Pesticide Information Profile. EXTOXNET. 
Abstracts 
1989 - Summary of Toxicology Data. California Department of Food and Agriculure, Medical Toxicology Branch. 
1983 - Summary of Data Reported and Evaluation - International Agency for Research on Cancer 
1980 - National Toxicology Program (NTP) Bioassay 
US Map of Pesticide use - 1992 - 1995
1990-1993 - Cotton pesticide usage in the US, 1990-1993 - USGS. Trifluralin (# 2); Fluometuron (#3); Norflurazon (# 9) 
See 3-(Trifluoromethyl)phenyl urea, a breakdown product
Occurrence of Cotton Pesticides in Surface Water - The major herbicides and their metabolites that have been detected in surface water of the Mississippi Embayment. The most-detected compound was fluometuron (see table). The demethyl metabolites, demethylfluo-meturon and demethylnorflurazon, were also commonly detected.  
February 2000 - Hungary's Pesticide Industry produces the fluorinated pesticides: Benefin (BENFLURALIN); Flufenzin; Fluometuron; Trifluralin. Hungary's pesticide industry includes partnerships with DuPont, Rhone Poulenc, and the American CEDAR group. Hungary's Ministry of Economic Affairs. 
2000 Toxic Release Inventory: Brief Summary.
See also: 3-Trifluoromethyl aniline - used as an intermediate in the production of Fluometuron
Herbicide Products - partial list 

EPA DOCUMENTS. The following documents were made available in the Federal Register docket:
0024-0029: January 31, 2007
all the rest: April 6, 2005
Docket No. Title Date
EPA-HQ-OPP-2004-0372-0024 Revised drinking water assessment and EFED’s Response to Exponent, Inc. “SCI-GROW Modeling for Fluometuron and Its Primary Metabolite, Desmethyl Fluometuron; and NAWQA Monitoring Data on Fluometuron
- 18 pages
Sept 27, 2005
EPA-HQ-OPP-2004-0372-0025 Impacts Assessment for Fluometuron
- 20 pages
Sept 26, 2005
EPA-HQ-OPP-2004-0372-0026 Refined Fluometuron Percent Crop Treated and Percentage of National Soybean, Corn, and Wheat Crops Rotated with Fluometuron-Treated Cotton (62 pages)
- 62 pages
Aug 9, 2005
EPA-HQ-OPP-2004-0372-0027 Addendum to Refined Fluometuron Percent Crop Treated
- 17 pages
Sept 21, 2005
EPA-HQ-OPP-2004-0372-0028 Usage report in Support of Reregistration for the herbicide Fluometuron Sept 14, 2005
EPA-HQ-OPP-2004-0372-0029 Fluometuron: Revised acute, chronic, and cancer dietary exposure assessments for the Reregistration Eligibility Decision (RED) document
- 41 pages
Sept 27, 2005
OPP-2004-0372-0002 

Overview of Fluometuron Risk Assessment
- 16
pages

March 30, 2005
OPP-2004-0372-0003 

Reader's Guide to Fluometuron 
- 3
pages

March 29, 2005
OPP-2004-0372-0004  Fluometuron Use Closure Memorandum.
- 2
pages
July 9, 2004
OPP-2004-0372-0005 

Table 1. Maximum Fluometuron Use Rates and Management Practices by Crop Based on Current Labels 
- 2
pages

April 6, 2004
OPP-2004-0372-0006 

Table A2. Food/Feed Use Patterns Summary for Fluometuron 
- 4
pages

April 6, 2004
OPP-2004-0372-0007  Screening Level Estimates of Agricultural Uses of Fluometuron (SLUA) 
- 2
pages
March 16, 2004
OPP-2004-0372-0008  Fluometuron: Revised HED Risk Assessment for Phase III of the Reregistration Eligibility Decision
- 66
pages
Feb 1, 2005
OPP-2004-0372-0009  Revised Environmental Fate and Ecological Risk Assessment of Fluometuron 
- 224
pages
Feb 22, 2005
OPP-2004-0372-0010  Fluometuron Drinking Water Assessment for the Human Effects Division (HED) Reregistration Eligibility Decision Document 
- 28
pages
Dec 3, 2004
OPP-2004-0372-0011 Phase 2 Response to Error Comments for Fluometuron RED (HED Risk Assessment)
- 3
pages
Feb 1, 2005
OPP-2004-0372-0012 Makhteshim's Review of the Health Effects Division Fluometuron Draft Science Chapter 
- 2
pages
Jan 13, 2004
OPP-2004-0372-0013  Makhteshim's Review of the Fluometuron Environmental Fate and Effects Science Chapter - 4 pages Dec 2, 2004
OPP-2004-0372-0014  EFED response to Registrant's 30 day Error Correction Comments on Fluometuron RED
- 6
pages
Feb 22, 2005
OPP-2004-0372-0015 Cotton Council Meeting notes
- 1
page
Aug 21, 2004
OPP-2004-0372-0016  Fluometuron. Acute, Chronic, and Cancer Dietary Exposure Assessments for the Reregistration Eligibility Decision (RED) Document  
- 34
pages
Nov 30, 2004
OPP-2004-0372-0017 Fluometuron: Occupational Exposure Assessment for the Reregistration Eligibility Decision Document 
- 38
pages
Dec 7, 2004
OPP-2004-0372-0018  Fluometuron. Summary of Product Chemistry for the Reregistration Eligibility Decision (RED) Document.
- 12
pages
Nov 3, 2004
OPP-2004-0372-0019 

Fluometuron. Summary of Analytical Chemistry and Residue Data for the Reregistration Eligibility Decision (RED) Document
- 38
pages

Nov 30, 2004
OPP-2004-0372-0020  Fluometuron Request for Information and Mitigation Proposals Phase 3 of 4-Phase Process
- 3
pages
March 30, 2005 

Pesticide use rates estimated from the past 10 years indicate that the fluometuron use rates are dropping considerably. This reduction in use of fluometuron is likely due to available glyphosate resistant cotton (Roundup Ready@). Pesticide use rates compiled by the National Center for Food and Agricultural Policy from pesticide use information
from 1990-1993 and 1995 indicated a total of 4,500.857 pounds of fluometuron use in the U.S.
A more recent screening level estimate conducted by the EPA for the agricultural uses of fluometuron
from 1998 to 2002 indicate 2.400.000 pounds with a 20% average percent crop treated on cotton in the U.S.
Additionally, the registrant indicated that by their records, the annual usage of fluometuron has dropped dramatically in the last 4 years from approximately 3.7 million pounds in 2000 to approximately 1 million pounds in 2003. (Page 2)
Ref. February 1, 2005. US EPA: Fluometuron: Revised HED Risk Assessment for Phase III of the Reregistration Eligibility Decision. Docket Identification Number: OPP-2004-0372-0008. 
http://www.fluorideaction.org/pesticides/fluometuron.opp-2004-0372-0008.pdf

Twelve of the 26 most widely used pesticides in the U.S. are classified as possible or probable carcinogens by the EPA based on studies of laboratory animals, with an annual use that totals 380 million pounds. (atrazine (C=possible), metolachlor (C), metarn sodium (B2=probable), dichloropropene (B2), cyanazine (C), pendimethalin (C), trifluralin (C), acetochlor (B2), chlorothalonil (likely), mancozeb (B2), fluometuron (C), and parathion (C)... [Journal of Pesticide Reform, Summer 1999, at 5]
Ref: Testimony of the Maine Organic Farmers and Gardeners Association in support of L.D. 1540: "An Act to Ensure that the State Board of Pesticides Control has Sufficient Resources to Provide Accurate Information About the Use of Pesticides in the State"
-- Note from FAN: Trifluralin, cited above, is another fluorinated pesticide.


US Federal Register

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

Date Published Docket Identification Number Details
January 31, 2007 EPA-HQ-OPP-2004-0372

Fluometuron Reregistration Eligibility Decision. This notice announces the availability of EPA's Reregistration Eligibility Decision (RED) for the pesticide fluometuron. The Agency's risk assessments and other related documents also are available in the fluometuron Docket. Fluometuron is a phenylurea herbicide that is used only on cotton. "Opportunities for public comment were offered at the initial docket opening in April 2005 and as this decision was being developed. Further, issues related to fluometuron were resolved through consultations with stakeholders. The Agency therefore is issuing the fluometuron RED without a comment period."

Docket No. Title Date
EPA-HQ-OPP-2004-0372-0024 Revised drinking water assessment and EFED’s Response to Exponent, Inc. “SCI-GROW Modeling for Fluometuron and Its Primary Metabolite, Desmethyl Fluometuron; and NAWQA Monitoring Data on Fluometuron
- 18 pages
Sept 27, 2005
EPA-HQ-OPP-2004-0372-0025 Impacts Assessment for Fluometuron
- 20 pages
Sept 26, 2005
EPA-HQ-OPP-2004-0372-0026 Refined Fluometuron Percent Crop Treated and Percentage of National Soybean, Corn, and Wheat Crops Rotated with Fluometuron-Treated Cotton (62 pages)
- 62 pages
Aug 9, 2005
EPA-HQ-OPP-2004-0372-0027 Addendum to Refined Fluometuron Percent Crop Treated
- 17 pages
Sept 21, 2005
EPA-HQ-OPP-2004-0372-0028 Usage report in Support of Reregistration for the herbicide Fluometuron Sept 14, 2005
EPA-HQ-OPP-2004-0372-0029 Fluometuron: Revised acute, chronic, and cancer dietary exposure assessments for the Reregistration Eligibility Decision (RED) document
- 41 pages
Sept 27, 2005

August 3, 2005 OPP-2005-0201

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

Section 3 registrations canceled for non-payment of the 2005
maintenance fee are shown in the following table 2:

Table 2.--Section 3 Registrations Canceled for Non-Payment of
Maintenance Fee

Registration no. Product Name
066222-00031 Cotoran 80w Herbicide

 
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