Flucarbazone-sodium
CAS No. 181274-17-9
 
 

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ACTIVITY: Herbicide (Triazolone)

Scientific Name: 4,5- dihydro-3-methoxy-4-methyl-5-oxo-N-[[2- (trifluoromethoxy)phenyl]sulfonyl]-1H-1,2,4-triazole-1-carboxamide, sodium salt

Flucarbazone-sodium breakdown product: 2-(Trifluoromethoxy)benzenesulfonamide (metabolite of MKH 6562) (CAS No. 37526-59-3)

N-desmethyl degradate: 4,5-dihydro-3-methoxy-5- oxo-N-[[2-( trifluoromethoxy)phenyl]sulfonyl]-1H-1,2,4-triazole-1- carboxamide

Structure for Flucarbazone:

Adverse Effects:

Body Weight Decrease
Bone
Endocrine: Thyroid
Endocrine: Uterus
Immunological effects
Liver
Stomach

Environmental Effects:

Potential to Contaminate Drinking Water

With chronic exposure, flucarbazone-sodium reduces fish growth at 2.75 ppm

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes
US EPA PC Code: 114009 
California Chemical Code 5803  
US Tolerances: CFR 180.562 
Registered use in
(includes only a limited list of countries)

Canada, UK, US

Canada: Wheat (durum)
Wheat (spring)

US Maximum Residue Levels permitted in food commodities
Permitted in or on 20 food commodities, including:
Cattle, Goats, Hogs, Horses, Milk, Sheep, Wheat (grain, hay, straw)
 
Other Information
Molecular Formula: C12H10 F3 N4O6S ´Na 
Manufacturers: Bayer, DuPont 
Other Names: Everest 70 WG,
Vulcano, K2,
MKH-6562,
SJO-0498
 
Of special interest:
PAN Data 
• new - Flucarbazone-sodium: Material Safety Data Sheets & Labels
July 19, 2005 - Canada. Reduced-Risk Update. Report: RR2005-02. Canada Pest Management Regulatory Agency (PMRA).
See excerpted list of fluorinated pesticides.
September 29, 2000 - Pesticide Fact Sheet. US EPA. 
September 19, 2001 - Canada Food and Drug Regulations - Amendment. Schedule 1256. Maximum Residue Limit of 0.01 ppm for Flucarbazone- sodium and its metabolite, for Wheat.  
March 12, 2001 - Active ingredient in K2 herbicide. - DuPONT press release 
See also: Flucarbazone
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. 
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: Flucarbazone-sodium  

US Federal Register

•• Note: The entries in the FR are too long to list here. Click here to see all the entries.

Date Pubished Docket Identification Number Details
December 22, 2006 EPA-HQ-OPP-2006-0935

Arysta LifeScience. Pesticide tolerance. FINAL RULE. This regulation establishes a tolerance for combined residues
of flucarbazone-sodium, 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2(trifluoromethoxy)phenyl] sulfonyl-1H-1,2,4-triazole 1-carboxamide, sodium salt and its N-desmethyl metabolite in or on
-- wheat, forage at 0.30 ppm
-- wheat, grain at 0.01 ppm
-- wheat, hay at 0.10 ppm
-- wheat, straw at 0.05 ppm;
and combined residues of flucarbazone-sodium and its metabolites converted to 2-(trifluoromethoxy) benzene sulfonamide and calculated as flucarbazone-sodium in or on
-- milk at 0.005 ppm
-- meat and meat byproducts (excluding liver) of cattle, goats, hogs, horses, and sheep at 0.01 ppm
-- liver of cattle, goats, hogs, horses, and sheep at 1.5 ppm.

October 20, 2006 EPA-HQ-OPP-2006-0789 Arysta LifeScience. Pesticide petition: 6F7112.
New Tolerance proposes to establish a tolerance for residues of flucarbazone sodium: in or on the raw agricultural commodities (RACs):
-- Wheat, forage at 0.30 ppm
-- Wheat, grain at 0.01 ppm
-- Wheat, hay at 0.10 ppm
-- Wheat, straw at 0.05 ppm

and combined residues of flucarbazone-sodium and its metabolites converted to 2-(trifluoromethoxy)benzene sulfonamide and calculated as flucarbazone-sodium in or on the RACs:
-- Milk at 0.005 ppm
-- Meat and meat byproducts except liver (cattle, goats, sheep, horses, hogs) at 0.01 ppm
-- Liver (cattle, goats, sheep, horses, hogs) at 1.50 ppm
Nov 9, 2005 OPP-2005-0254

Arysta LifeScience. Time-Limited Pesticide Tolerance. FINAL RULE. The time limited-tolerance previously issued September 29, 2000, will be extended for 13 months and will expire on November 30, 2006. A time-limited tolerance will be issued due to outstanding studies (independent laboratory validations of: Analytical Method for the Determination O-Desmethyl MKH 6562 (Metabolite of MKH 6562 in Soil by High Performance Liquid Chromatography Tandem Mass Spectrometry), Analytical Method for the Determination of MKH 6562 and Metabolites NODT (N,O-dimethyltriazolinone), Sulfonic Acid and Sulfonamide in Soil by High Performance Liquid Chromatography Tandem Mass Spectrometry, and Analytical Method for the Determination of MKH 6562 and Three Metabolites in Groundwater by High Performance Liquid Chromatography Tandem Mass Spectrometry) will be submitted to the Agency by the registrant in January 2006.

A summary of the toxicological endpoints for flucarbazone-sodium used for human risk assessment is discussed in final rule published in the Federal Register of September 29, 2000.

the estimated environmental concentrations (EECs) of flucarbazone-sodium for acute exposures are estimated to be 1.42 parts per billion (ppb) or surface water and 0.2 ppb for ground water. The EECs for chronic exposures are estimated to be 1.25 ppb for surface water and 0.2 ppb for ground water.

A default Maximum Residue Limit (MRL) of 0.01 ppm has been established in Canada for residues of flucarbazone-sodium and its N-desmethyl metabolite on wheat grain. This value is consistent with the
tolerance being established in the United States on wheat grain.

Sec. 180.562 Flucarbazone-sodium; tolerances for residues.
(a) General. (1) Time-limited tolerances are established for combined residues of the herbicide flucarbazone-sodium and its N-desmethyl metabolite in or on the following food commodities:
Commodity Parts per million Expiration/Revocation Date
Wheat, forage 0.30 11/30/06
Wheat, grain 0.01 11/30/06
Wheat, hay 0.10 11/30/06
Wheat, straw 0.05 11/30/06

(2) Time-limited tolerances are established for combined residues of the herbicide flucarbazone-sodium and its metabolites converted to 2-(trifluoromethoxy)benzene sulfonamide and calculated as flucarbazone-sodium in or on the following food commodities:

 

Commodity Parts per million Expiration/Revocation Date
Cattle, liver 1.50 11/30/06
Cattle, meat 0.01 11/30/06
Cattle, meat byproducts except liver. 0.01 11/30/06
Goat, liver 1.50 11/30/06
Goat, meat 0.01 11/30/06
Goat, meat byproducts except liver. 0.01 11/30/06
Hog, liver 1.50 11/30/06
Hog, meat 0.01 11/30/06
Hog, meat byproducts except liver. 0.01 11/30/06
Horse, liver 1.50 11/30/06

Horse, meat

0.01 11/30/06
Horse, meat byproducts except liver. 0.01 11/30/06
Milk 0.005 11/30/06
Sheep, liver 1.50 11/30/06
Sheep, meat 0.01 11/30/06
Sheep, meat byproducts except liver. 0.01 11/30/06
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
066330 ID-04-0005 Everest 70% Water Dispersible Granular Herbicide
066330 MN-04-0004 Everest 70% Water Dispersible Granular Herbicide
066330 ND-04-0002 Everest 70% Water Dispersible Granular Herbicide
066330 WA-04-0025 Everest 70% Water Dispersible Granular Herbicide
July 27, 2005 OPP-2005-0139

Arvesta Corporation - Pesticide Petition: PP 5F6949. Petition to establish pesticide tolerance. The proposed tolerance expression is parent flucarbazone-sodium and N-desmethyl flucarbazone-sodium.

An acute neurotoxicity screening study in rats established an overall NOAEL for males and females of 500 mg/kg based on transient neurobehavioral effects.
Reproductive and developmental toxicity. Himalayan rabbits were administered flucarbazone-sodium at levels of 0, 100, 300, 500, or 1,000 mg/kg/bwt by oral gavage days 6 through 28 post coitum in a test for developmental toxicity. A maternal NOAEL of 100 mg/kg bwt/day was established based on clinical findings, body weight loss, decreased feed consumption, gastrointestinal changes, increased liver weights, and fatty liver changes at 300 mg/kg bwt/day. The gestation rate NOAEL of 100 mg/kg bwt/day was based on one abortion (assessed as secondary due to maternal toxicity) at 300 mg/kg bwt/day. The NOAEL for fetal parameters of 300 mg/kg bwt/day was based on decreased fetal weights and delayed ossification at 500 mg/kg bwt/day.

Subchronic toxicity. A 28-day dermal rabbit study established a systemic NOAEL of >1,000 mg/kg bwt/day (the dermal limit dose) for males and females. The local dermal effects, skin thickening, seen at 1,000 mg/kg were regarded as a result of mechanical friction and of no toxicological relevance.

-- A 90-day rat feeding study defined a NOAEL at 250 ppm (17.6 mg/ kg bwt/day) for males and 1,000 ppm (101.7 mg/kg bwt/day) for females based on a decreased spleen weight in males at 1,000 ppm and on immunologic changes at 4,000 ppm in females.
-- A 90-day feeding study with male and female B6C3F1 mice established a NOAEL of 7,000 ppm (equivalent to >2,083, and 3,051 mg/kg bwt/day for males and females, respectively). The dose of 7,000 ppm was the HDT.
-- A 90-day dog feeding study at levels of 0, 1,000, 5,000, and 50,000 ppm established a NOAEL of 1,000 ppm (equivalent to 33.8 mg/kg bwt/day in males and 35.2 mg/kg bwt/day in females) based on decreased thyroxine levels and increased thyroxine-binding capacity, macroscopic and microscopic effects on the gastric mucosa and an eosinophilic hepatocellular cytoplasm occurring at 5,000 ppm and above. The liver enzyme induction at 1,000 ppm was assessed as a slight adaptive response in the detoxification process of flucarbazone-sodium but not as an adverse effect, due to the absence of clinical chemical changes that would indicate liver damage and due to the absence of any histopathologic liver changes at this dietary level.
--
A 28-day (6 hours/day; 5 days/week) subacute inhalation toxicity study was conducted with male and female Wistar rats exposed to mean actual concentrations of 5.2, 30.0, 180.1 and 513.3 mg/m3 air. A NOAEL of 5.2 mg/m3 air was established based on histopathological changes observed at 30 mg/m3 air and above.

To establish a tolerance for residues of flucarbazone-sodium: 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-[[2-(trifluoromethoxy)phenyl]sulfonyl]-1H-1,2,4-triazole 1-carboxamide, sodium salt; and its N-desmethyl metabolite in or on the raw agricultural commodities (RACs):
Commodity   Parts per million
Wheat, forage 0.30
Wheat, grain 0.01
Wheat, hay 0.10
Wheat, straw 0.05
And combined residues of flucarbazone-sodium and its metabolites converted to 2-(trifluoromethoxy)benzene sulfonamide and calculated as flucarbazone-sodium in or on the raw agricultural commodities:
Commodity    Parts per million
Milk 0.005
Meat and meat byproducts except liver
(cattle, goats, sheep, horses, hogs)
0.01
Liver (cattle, goats, sheep, horses, hogs) 1.50

•• Note: The entries in the FR are too long to list here. Click here to see all the entries.

 
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