Pyraflufen-ethyl

269.79400

413.18

603-347-1

XOC9Q2DLMI

DTXSID8034871

Fine, cream-colored powder|Pale brown, crystalline

80.26000

-0.85600

1.5g/cm3

126-127 °C

445.4ºC

223.2ºC

1.546

In xylene 41.7-43.5, acetone 167-182, methanol 7.39, ethyl acetate 105-111 (all in g/L, 20 °C)|In water, 8.2X10-2 mg/L at 20 °C

Store in a cool place. Do not contaminate water, food or feed by storage or disposal. /ET Herbicide/Defoliant (a.i. 2.5%); ET 2%SC Herbicide/Defoliant/|Storage: store in original container and keep closed. Store in a cool, dry place. /ET-751 Technical (a.i. 97.9%)/

3.97E-08mmHg at 25°C

Henry's Law constant = 8.1X10-5 Pa-cu m/mol (est)

pKa = 2.9 (est)

Hydroxyl radical reaction rate constant = 4.23X10-11 cu cm/molec-sec at 25 °C (est)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Open dumping is prohibited. Pesticide Disposal: Pesticide wastes are toxic. Improper disposal of excess pesticide, pesticide spray or rinsate is a violation of Federal law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste representative at the nearest EPA Regional Office for guidance. Container Disposal: DO NOT reuse empty container. Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in sanitary landfill, or incineration, or if allowed by state and local authorities, by burning. If burned, stay out of smoke. /ET Herbicide/Defoliant (a.i. 2.5%); ET 2% SC Herbicide/Defoliant/|Pesticide Disposal: Do not contaminate water, food or feed by storage or disposal. Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. Container Disposal: Completely empty liner by shaking and tapping sides to loosen clinging particles. Empty residue into formulalation equipment. Then dispose of liner in a sanitary landfill or by incineration, if allowed by state and local authorities. If drum is contaminated and cannot be resused, dispose of in the manner required by law. /ET-751 Technical (a.i. 97.9%)/|Do not discharge effluent containing this product directly into lakes, streams, ponds, estuaries, oceans ora ny other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge. Do not discharge effluent containing this product to sewer systems without previously notifying the local sewage treatment plant authority. For guidance, contact your State Water Board or Regional Office of the EPA. Do not contaminate water when disposing of equipment washwaters. /ET-751 Technical (a.i. 97.9%)/

|Warning|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501

Applicators and other handlers must wear long-sleeved shirt and long pants, chemical resistant (such as nitrile or butyl) gloves, shoes plus socks, protective eyewear, chemical resistant headgear for overhead exposure. When handlers use closed systems, enclosed cabs, or aircraft in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides (40 CFR 170.240 (d) (4-6), the handler PPE requirements may be reduced or modified as specified in the WPS. /ET Herbicide/Defoliant (a.i. 2.5%)/|Applicators and other handlers must wear long-sleeved shirt and long pants, shoes plus socks, and chemical-resistant gloves. When handlers use closed systems, enclosed cabs, or aircraft in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides (40 CFR 170.240 (d) (4-6), the handler PPE requirements may be reduced or modified as specified in the WPS. /ET 2% SC Herbicide/Defoliant/

Do not allow the spray solution to dry in the application equipment. ... Immediately following application, clean all equipment thoroughly with detergent or a spray tank cleaner and water... Drain sprayer tank, hoses, and spray boom and thoroughly rinse with clean water the inside of the spray tank, sprayer hoses, boom, and nozzles to remove any sediment or residues. Fill the tank half full with clean water, add the appropriate detergent... Fill tank to capacity and operate the sprayer with agitation for 15 minutes... Drain the sprayer tank, lines, and booms. Rinse the tank with clean water and flush through the hoses, boom, and nozzles. Remove and clean spray nozzles, tips, and screens. Dispose of all cleaning solutions, rinsate, and washwaters in accordance with Federal, state, and local regulations. /ET Herbicide/Defoliant (a.i. 2.5%); ET 2%SC Herbicide/Defoliant/

If inhaled move person to fresh air. If person is not breathing, call 911 or an ambulance, then give artificial respiration ... Call a poison control center or doctor for further treatment advice. If swallowed call poison control center or doctor immediately for treatment advice. Have person sip a glass of water if able to swallow. Do not induce vomiting unless told to do so by the poison control center or doctor. Do not give anything by mouth to an unconscious person. /ET-751 Technical (a.i. 97.9%); ET Herbicide/Defoliant (a.i. 2.5%)/|Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /ET Herbicide/Defoliant (a.i. 2.5%); ET 2% SC Herbicide/Defoliant/|Users should wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /ET Herbicide/Defoliant (a.i. 2.5%); ET 2%SC Herbicide/Defoliant/|Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. PPE required for early entry to treated areas ... is coveralls, chemical resistant (such as nitrile or butyl) gloves, shoes plus socks, and protective eyewear. ... Only certified applicators are permitted to apply ET for turf and ornamental sites.... Use Restrictions: ... Do not apply this product through any type of irrigation system. /ET Herbicide/Defoliant (a.i 2.5%); ET 2%SC Herbicide/Defoliant/|For more Preventive Measures (Complete) data for PYRAFLUFEN-ETHYL (9 total), please visit the HSDB record page.

Harmful if absorbed through skin. Causes moderate eye irritation. /ET-751 Technical (a.i. 97.9%)/

Pyraflufen-ethyl's production may result in its release to the environment through various waste streams; its use as a herbicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 3.49(2) and a regression-derived equation(3), indicates that pyraflufen-ethyl is expected to have low mobility in soil(SRC). Volatilization of pyraflufen-ethyl from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 7.9X10-10 atm-cu m/mole(2). Pyraflufen-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.2X10-10 mm Hg(2). Biodegradation data were not available(SRC, 2007).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 3.49(2) and a regression-derived equation(3), indicates that pyraflufen-ethyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 7.9X10-10 atm-cu m/mole(2). According to a classification scheme(4), an estimated BCF of 97(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Pyraflufen-ethyl is stable in water at pH 4, has a half-life of 13 days at pH 7, and is rapidly hydrolyzed at pH 9(2). An aqueous photolysis half-life of 30 days has been reported(2). Biodegradation data were not available(SRC, 2007).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyraflufen-ethyl, which has a vapor pressure of 1.2X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase pyraflufen-ethyl may be removed from the air by wet or dry deposition(SRC). Pyraflufen-ethyl contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(3). An aqueous photolysis half-life of 30 days has been reported(2).

Pyraflufen-ethyl is stable in water at pH 4, has a half-life of 13 days at pH 7, and is rapidly hydrolyzed at pH 9(1). Pyraflufen-ethyl contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(2). An aqueous photolysis half-life of 30 days has been reported(1).

An estimated BCF of 97 was calculated in fish for pyraflufen-ethyl(SRC), using a log Kow of 3.49(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Koc of pyraflufen-ethyl is estimated as 1,900(SRC), using a log Kow of 3.49(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that pyraflufen-ethyl is expected to have low mobility in soil.

The Henry's Law constant for pyraflufen-ethyl is 7.9X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pyraflufen-ethyl is expected to be essentially nonvolatile from water surfaces(2). Pyraflufen-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.2X10-10 mm Hg(1).

Occupational exposure to pyraflufen-ethyl may occur through inhalation and dermal contact with this compound at workplaces where pyraflufen-ethyl is produced or used. (SRC)

Pyraflufen-ethyl was readily absorbed and excreted within 96 hours following a single or repeated oral dose of 5 mg/kg (plasma t1/2 of 3 to3.5 hours). However, at a dose of 500 mg/kg, absorption was saturated as indicated by Cmax values which did not reflect the 100- fold dose differential (2.7 to 2.8 Fg eq/g for the low-dose group and 100 to 107 Fg eq-hr/g for the high-dose group). Following single or multiple oral low doses (5 mg/kg) of pyraflufen ethyl, urinary excretion accounted for 27 to 33% of the administered radioactivity suggesting that a multiple exposure regimen did not affect the absorption/excretion processes. Urinary excretion was reduced to only 5 to 7% following a single 500 mg/kg dose. Excretion via the feces accounted for the remainder of the administered radioactivity in all treatment groups. Analysis of biliary excretion following a single 5 mg/kg dose showed that 36% of the administered dose appeared in the bile. Based upon the excretion data, total bioavailability of a low dose was approximately 56%. Biliary excretion data were not available for a high-dose group which prevented a definitive assessment of bioavailability. Excretory patterns did not exhibit gender-related variability. However, plasma and blood clearance was more rapid in females than in males as shown by plasma/blood radioactivity time-course and the greater AUC values for males (32.3 vs 18.4 Fg eq-hr/g for the low-dose group and 2,738 vs 1,401 Fg eq-hr/g for the high-dose group). Radioactivity concentrations indicated tissue concentrations at or near detection limits (generally <0.01 Fg eq/g and never exceeding 0.02 Fg eq/g) at 96 hours postdose for any tissues. Therefore, neither pyraflufen-ethyl nor its metabolites appear to undergo significant sequestration. Tissue burden data following compound administration did not suggest a specific target beyond those tissues, namely liver and kidney, which are associated with absorption and elimination of orally administered xenobiotics.[EPA 40 CFR Part 180

5 Sprague-Dawley rats per sex received a single oral gavage dose of [Phenyl- U-14C] ET-751 at 5 mg/kg. Immediately after dosing, each animal was transferred to a glass metabolism cage. Urine and feces were collected at 24 hour intervals through 96 hours. ... Metabolites in urine and feces were evaluated by high performance liquid chromatography (HPLC) and 2-D thin layer chromatography. ... Metabolites were identified in urine and feces ... As with [Pyrazole-5-14C] ET-751, the proposed metabolic pathways were ester hydrolysis and N-demethylation on the pyrazole ring 1 position and hydrolysis of the ether bond on 5 position of the phenyl ring to phenol and methylation to the methoxy moiety.|20 male Sprague-Dawley rats received non-labelled ET-751 Technical by oral gavage at 5 mg/kg/day for 14 days. On the 15th day, they received a single oral gavage dose of [Pyrazole-5- 14C] ET-751 at 5 mg/kg. ... Metabolites in urine, feces, plasma, and gastrointestinal contents were identified using high performance liquid chromatography (HPLC). At 96 hours, the total values were 26.66% and 64.44% for urine and feces respectively. ... At 96 hours, concentrations were at or below the limits of detection in all samples. Metabolites in urine, feces, and plasma were identified ... The proposed metabolic pathways were ester hydrolysis and N-demethylation on the pyrazole ring 1 position and hydrolysis of the ether bond on 5 position of the phenyl ring to phenol and methylation to the methoxy moiety.|6 male Sprague-Dawley rats with cannulated bile ducts received a single oral gavage dose of [Pyrazole-5-14C] ET-751 at 5 mg/kg. ... High performance liquid chromatography was used to identify metabolites. 17.90% (feces), 19.66% (urine) and 36.09% (bile) of dosed radioactivity were excreted during 48 hours post-dosing. 13.86% was found in the gastrointestinal contents and 2.86% in the gastrointestinal tract at 48 hours. Absorption from oral administration was estimated as 55.75% (urine and bile content combined). Metabolites in urine, feces, gastrointestinal tract, and gastrointestinal contents were identified ... Proposed metabolic pathways were ester hydrolysis and N-demethylation on the 1 position of the pyrazole ring and hydrolysis of the ether bond on the 5 position of the phenyl ring to the phenolic hydroxy moiety.|5 Sprague-Dawley rats per sex per group received a single dose of [Pyrazole-5-14C] ET-751 at 5 or 500 mg/kg followed by sacrifice 3, 6, 9, 24, 96, or 168 hours later. ... Metabolites were identified in urine, plasma, and feces ... Proposed metabolic pathways were ester hydrolysis and N-demethylation on the pyrazole ring 1 position and hydrolysis of the ether bond on the 5 position of the phenyl ring to phenol and methylation to the methoxy moiety.

/SIGNS AND SYMPTOMS/ Corrosive. Causes irreversible eye damage. Harmful if absorbed through skin. /ET Herbicide/Defoliant (a.i. 2.5%)/|/SIGNS AND SYMPTOMS/ Harmful if absorbed through skin. Causes moderate eye irritation. /ET-751 Technical (a.i. 97.9%)/|/GENOTOXICITY/ Duplicate cultures of human (male) whole blood lymphocytes (stimulated for 48 hours with PHA) were exposed to ET-751 Technical (97.6% pyraflufen-ethyl), in the presence and absence of rat liver S9, at 0 (DMSO), 650, 1300, and 2600 ug/mL in two assays. Non-activated cultures were exposed for 19 or 43 hours; cultures with activation for 3 hours and harvested 16 or 40 hours later. One thousand lymphocytes per culture were scored for metaphases (mitotic index) and one hundred metaphases were examined for aberrations. Test article precipitation was reported in all cultures treated at 2600 ug/mL. No increase in aberrant metaphases. Positive controls were functional.

ET-751 TECHNICAL: 97.9% Ethyl 2-chloro-5-(4-chloro-(5-difluoromethoxy)-1-methyl-1H-pyra zol-3-yl)-4-fluorophenoxyacetate|ET HERBICIDE/DEFOLIANT: 2.5% Ethyl 2-chloro-5-(4-chloro-(5-difluoromethoxy)-1-methyl-1H-pyra zol-3-yl)-4-fluorophenoxyacetate|ET 2% SC HERBICIDE/DEFOLIANT: 2.0% Ethyl 2-chloro-5-(4-chloro-(5-difluoromethoxy)-1-methyl-1H-pyra zol-3-y)]-4-fluorophenoxyacetate

Conditions .. for this proposed use ... The following data are being required by the Agency to complete the database requirements prior to approval of an unconditional registration of pyraflufen-ethyl on cotton: Product label contain a statement limiting use to commercial applicators only so that possible use by homeowners on residential turf would be minimized and/or include a restriction prohibiting use by homeowners for the turf and ornamental use sites. Proposed uses in farmyards, farm buildings, fence lines, dry ditches and ditch banks be removed from the label due to the potential for residues to contact food sources in these use sites. The label for pyraflufen ethyl should clearly state the allowable number of applications per season.[EPA 40 CFR Part 180

Nichino America, Inc. has submitted a petition method validation (PMV) and an independent laboratory validation for a Gas Chromatography/Mass Spectometry (GC/MS) method proposed for the enforcement of tolerances for residues of pyraflufen ethyl and its acid metabolite, E-1((2-chloro-5-(4- chloro-5-difluoromethoxy-1-methyl-1Hpyrazol- 3-yl)-4-fluorophenoxyacetic acid).[EPA 40 CFR Part 180

Agrochemicals -> Herbicides|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Pyraflufen-ethyl has known environmental transformation products that include Pyraflufen-ethyl metabolite E-1, Pyraflufen-ethyl metabolite E-11, Pyraflufen-ethyl metabolite E-2, Pyraflufen-ethyl metabolite E-3, and Pyraflufen-ethyl metabolite E-9.