Diflufenzopyr
CAS No. 109293-97-2
Diflufenzopyr, sodium salt
CAS No. 109293-98-3
 
 

Return to Diflufenzopyr Adverse Effects

ACTIVITY: Herbicide (urea)

CAS Name for Diflufenzopyr: 2-[1-[[[(3,5-difluorophenyl)amino]carbonyl]hydrazono]ethyl]-3-pyridinecarboxylic acid

Structure for Diflufenzopyr:

Diflufenzopyr Adsverse Effects:

Anemia
Body Weight Decrease
Bone
Brain
Endocrine: Testicular
Endocrine: Thymus
Kidney
Lung
Spleen

Environmental:
A metabolite of diflufenzopyr known as M9 - persistent in soil and water.

Diflufenzopyr Diflufenzopyr, sodium salt
US EPA Registered: Yes US EPA Registered: Yes  
US EPA PC Code: 005108 US EPA PC Code: 005107 
California Chemical Code 5750 California Chemical Code 5751 
Registered use in
(includes only a limited list of countries)
 

Canada, US

Canada: Corn (field)

Registered use in
(includes only a limited list of countries)
 
US
US Tolerances: CFR 180.549 US Tolerances: -
US Maximum Residue Levels permitted in food commodities permitted in or on 31 food commodities, including:
Cattle, Corn, Goat, Grass, Hog, Horse, Milk, Sheep

US Maximum Residue Levels permitted in food commodities permitted in or on 31 food commodities, including:
Cattle, Corn, Goat, Grass, Hog, Horse, Milk, Sheep
 
Other Information
Molecular Formula: C15H12 F2 N4O3  Molecular Formula:  -
Entry Year: 1994  Entry Year: - 
Inventing Company: Sandoz  Inventing Company:  
Manufacturers: BASF  Manufacturers:  BASF 

Herbicide Products:

as of Dec 2003

Diflufenzopyr technical herbicide Herbicide Products:

as of Dec 2003 
Celebrity plus herbicide

Distinct herbicide

Sodium diflufenzopyr technical herbicide
Of special interest:
Diflufenzopyr Diflufenzopyr, sodium salt 
PAN Data PAN Data 
July 19, 2005 - Canada. Reduced-Risk Update. Report: RR2005-02. Canada Pest Management Regulatory Agency (PMRA).
See excerpted list of fluorinated pesticides.
March 4, 2005 - DISTINCT. Proposed Regulatory Decision Document PRDD2005-01. Pest Management Regulatory Agency. Ottawa, Canada. The herbicide Distinct contains 20% diflufenzopyr (109293-97-2) and 50% dicamba; may be used for pre-emergent through late postemergent application on field corn in Eastern Canada. Distinct is not for use on sweet corn or seed corn.
July 13, 2000 - Summary of Toxicology Data for Diflufenzopyr. CA EPA, Department of Pesticide Regulation, Medical Toxicology Branch.  
April 14, 1999 - Regulatory Note REG99-02. Canada Submission Management and Information Division, Pest Management Regulatory Agency.
January 28, 1999 - US EPA Fact Sheet - (pdf)
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. Also available at: http://vm.cfsan.fda.gov/~acrobat/pestglos.pdf
August 2001 - IR-4: New Products/Transitional Solution List - This list contains brief descriptions of numerous new pest control materials that have been introduced over the last several years. Additionally, it contains information on some "older" crop protection chemicals that are believed to have room for new uses. This List includes Diflufenzopyr  

Metabolites. Metabolism of diflufenzopyr in ruminants, poultry and the rat is similar to that which occurs in corn. Diflufenzopyr is partially metabolized to M5, which is further metabolized to M1, M9, M10, and M19 [page 75]
M1
8-methyl-5-hydroxy-pyrido(2,3-d)-pyridazine
M2
3,5-difluoroaniline
M5
6-((3,5-difluorophenyl) carbamoyl)-8-methyl-pyrido (2,3-d)-5-pyridazinone (carbamoyl phthalazinone)
M6
2-acetyl nicotinic acid
M8
N-(3,5-difluorophenyl)carbamate
M9
8-methylpyrido[2,3-d]pyridazine-2,5(1H, 6H)-dione (persistent in soil and water)
M10
8-hydroxymethyl-5(6H)pyrido[2,3-d]pyridazinone
M19
8-hydroxymethylpyrido[2,3-d]pyridazine-2,5(1H,6H)-dione
 

Ref: March 4, 2005 - DISTINCT. Proposed Regulatory Decision Document PRDD2005-01. Pest Management Regulatory Agency. Ottawa, Canada. The herbicide Distinct contains 20% diflufenzopyr (109293-97-2) and 50% dicamba


US Federal Register

•• Note: Not all entries are listed below. Click here to see all FR entries.

Date Published Docket Identification Number Details
October 5, 2007 No docket number

Notice of Availability of the Record of Decision for the Final Programmatic Environmental Impact Statement for Vegetation Treatments Using Herbicides on Bureau of Land Management Lands in 17 Western States. The fluorinated herbicides included for use are diflufenzopyr and fluridone. (Of the six herbicides rejected for use is the fluorinated mefluidide.) As part of the Proposed Action and this decision, the BLM also adopts the protocol for identifying, evaluating and approving herbicides. Copies of the Record of Decision are available in hard copy or CD upon request from Brian Amme, Nevada State Office, P.O. Box 12000, 1340 Financial Blvd., Reno, NV 89520, or via the Internet at the BLM National Web site http://www.blm.gov/. The Record of Decision is available for review in either hard copy or on compact disks (CDs) at all BLM State, District, and Field Office public rooms.

This national, FPEIS provides a comprehensive analysis of BLM's use of chemical herbicides in its various vegetation treatment programs related to hazardous fuels reduction; noxious weed, invasive terrestrial and aquatic plant species management; resource rehabilitation following catastrophic fires, and other disturbances. The FPEIS addresses human health and ecological risk for use of chemical herbicides on public lands and provides a cumulative impact analysis of the use of chemical herbicides in conjunction with other treatment methods. The decision area includes public lands administered by 11 BLM state offices: Alaska, Arizona, California, Colorado, Idaho, Montana (North Dakota/South Dakota), New Mexico (Oklahoma/Texas/Nebraska), Nevada, Oregon (Washington), Utah and Wyoming.

Draft PEIS, Part 1 AND Draft PEIS, Part 2. The PEIS provides a comprehensive programmatic NEPA document that addresses the primary controversial issue identified through scoping: the BLM’s continuing use and proposed increased use of herbicides in vegetation treatment programs that would implement the National Fire Plan and other related initiatives.

Draft PER describes the environmental effects of using non-herbicide treatment methods, including prescribed fire and mechanical, manual and biological controls, on vegetation, watersheds, and fish and wildlife habitat on surface lands administered by the BLM in the western United States, including Alaska.

Human Health Risk Assessment
Ecological Risk Assessment Protocol and Assessments
Draft Biological Assessment

Aug 29, 2002 OPP-2002-0220  IR-4; BASF. Pesticide Tolerances. FINAL RULE. This regulation establishes tolerances for combined residues of diflufenzopyr in or on corn, sweet, forage; corn, sweet, kernel plus cob with husks removed; and corn, sweet, stover at 0.05 ppm; corn, pop, grain and corn, pop, stover at 0.05 ppm; grass, forage at 22 ppm; and grass, hay at 7.0 ppm. This regulation also establishes time-limited tolerances for combined residues of diflufenzopyr in or on cattle, goat, hog, horse, and sheep meat at 0.60 ppm; cattle, goat, hog, horse, and sheep kidney at 4.0 ppm; cattle, goat, hog, horse, and sheep meat byproducts, except kidney at 0.50 ppm; cattle, goat, hog, horse, and sheep fat at 0.30 ppm; and milk at 3.0 ppm. The nature of the toxic effects caused by diflufenzopyr is discussed in the Final Rule on Diflufenzopyr published in the FR of January 28, 1999 - some excerpts:
-- In a subchronic feeding study in rats, male and female Wistar rats were fed test diets containing technical diflufenzopyr, purity 96%, at dose levels of 0, 1,000, 5,000, 10,000 and 20,000 ppm (equal to 0, 60.8, 352, 725 and 1,513 milligram/kilogram body weight/day (mg/kg bw/day) for males, and 0, 72.8, 431, 890 and 1,750 mg/kg bw/day for females) for a period of 13 weeks. decreased food intake (20,000 ppm, males only); slight increases in cholesterol (20,000 ppm, both sexes, and 10,000 ppm, males only) and ALAT (10,000 and 20,000 ppm, both sexes); and slightly lower chloride (20,000 ppm, both sexes). Histopathological findings were an increased incidence of foamy macrophages in the lungs in the 10,000 and 20,000 ppm groups, both sexes, and testicular atrophy in the 20,000 ppm group. Following the 4- week recovery period, the only treatment-related effects which showed partial or no evidence of recovery were foamy macrophages in the lungs and testicular atrophy.
-- In a subchronic toxicity study in dogs, diflufenzopyr (98% a.i.) was administered to beagle dogs (4/sex/dose) by feeding at dose levels of 0, 1,500, 10,000, or 30,000 ppm (0, 58, 403, or 1,131 mg/kg/ day for males; 0, 59, 424, or 1,172 mg/kg/day for females) for 13 weeks. The lowest adverse effect level (LOAEL) for this study is 10,000 ppm (403 mg/kg/day in males and 424 mg/kg/day in females), based on the occurrence of erythroid hyperplasia in the bone marrow, extramedullary hemopoiesis in the liver, and hemosiderin deposits in Kupffer cells.
-- In a chronic toxicity study in dogs, diflufenzopyr (98.1% a.i.) was administered to beagle dogs (4/sex/dose) by feeding at dose levels of 0, 750, 7,500, or 15,000 ppm (0, 26, 299, or 529 mg/kg/day for males; 0, 28, 301, or 538 mg/kg/day for females) for 52 weeks. The LOAEL for this study is 7,500 ppm (299 mg/kg/day for males and 301 mg/ kg/day for females), based on erythroid hyperplasia in the bone marrow in bone sections, reticulocytosis, and increased hemosiderin deposits in the liver, kidneys, and spleen.
-- In a developmental toxicity study, technical diflufenzopyr (98.1% a.i.) in 0.5% aqueous methyl cellulose was administered by gavage to 25 female Crl: CD BR VAF/Plus (Sprague Dawley) rats/dose at dose levels of 0, 100, 300, or 1,000 mg/kg/day from days 6 through 15 of gestation. The maternal NOAEL is 300 mg/kg/day and the maternal LOAEL is 1,000 mg/kg/day based on decreases in food consumption and weight gain. Developmental effects, characterized as significantly lower fetal body weights in males ( 5%) and skeletal variations, exhibited as incompletely ossified and unossified sternal centra and reduced fetal ossification sites for caudal vertebrae, were observed at 1,000 mg/kg/day.
-- In a developmental toxicity study, technical diflufenzopyr (98.1% a.i.) in 0.5% aqueous methyl cellulose was administered by gavage to 20 female New Zealand White Hra: (NZW)SPF rabbits/dose at dose levels of 0, 30, 100, or 300 mg/kg/day from days 6 through 19 of gestation. The maternal LOAEL is 100 mg/kg/day, based on minimal reductions in body weight gain with no reduction in food consumption and clinical signs of toxicity (abnormal feces). The maternal NOAEL is 30 mg/kg/day. Developmental effects, characterized as significant increases (p<ls-thn-eq>0.01) in the incidence of supernumerary thoracic rib pair ossification sites (12.74 vs. 12.54 for controls) occurred at the 300 mg/kg/day dose.
-- In a 2-generation reproduction study, technical diflufenzopyr (98.1% a.i.) was administered continuously in the diet to 26 Wistar rats/sex/dose at dose levels of 0, 500, 2,000 or 8,000 ppm in the diet (0, 27.3-42.2, 113.1-175.9, or 466.2-742.0 mg/kg/day). The systemic LOAEL is 2,000 ppm (113.1-175.9 mg/kg/day) based on reduced body weight gain, increased food consumption, and increased seminal vesicle weights. The systemic NOAEL is 500 ppm (27.3-42.2 mg/kg/day). The reproductive LOAEL is 8,000 ppm (466.2-742.0 mg/kg/day) based on lower live birth and viability indices, total pre-perinatal loss, reduced body weights and body weight gain during lactation, a higher proportion of runts, and a higher percentage of offspring with no milk in the stomach.
-- In an acute neurotoxicity study, diflufenzopyr (96.4% a.i.) was administered by gavage to Crl:CD BR rats (10/sex/group) at dose levels of 0, 125, 500 or 2,000 mg/kg. The rats were evaluated for reactions in functional observations and motor activity measurements at 3 hours, 7 days, and 14 days postdosing. Histopathological evaluation on the brain and peripheral nerves was assessed after day 14.
Diflufenzopyr had no definite impact on neurotoxic responses, although a few abnormalities were observed in the functional battery on the day of dosing. A decrease in immediate righting responses that was observed in several males in all treatment groups was not concentration- dependent. Nasal staining was observed in more rats in the 2,000 mg/kg treatment groups (6 males; 3 females), but was not considered a definite or significant response to treatment. Lower mean brain weights in all female treatment groups lacked associated macroscopic and microscopic histopathological changes, and were only 4-5% lower than the control brain weight. Mean locomotor activities for the 2,000 mg/kg female treatment groups were decreased on Days 7 (<difference> 27%, p < 0.05) and 14 (<difference>15%, not significant) after dosing, but the pattern of activity for the individual animals was similar to the individual controls over time...
-- Diflufenzopyr was tested up to cytotoxic dose levels and mutation frequencies were determined for dose levels selected on the basis of relativegrowth. Although initially declared positive by the then study director, application of more recent criteria for mutagenic responses has rendered the test article negative for forward gene mutation at the TK locus in mouse L5178Y cells in the presence and absence of S9 activation.

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