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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