Carfentrazone-ethyl

412.19

412.19

603-291-8

DTXSID4032532

Viscous yellow-orange liquid

62.2

3.36

1.457 g/cu cm at 20 deg C

-22.1 °C

352.5 °C

>110°C

1.574

Solubility in toluene 0.9 g/mL at 20 deg C,1.06 g/mL at 25 deg C, 1.2 g/mL at 25 deg C. Solubility in hexane 0.03 g/mL at 20 deg C, 0.05 g/mL at 25 deg C, 0.05 g/mL at 30 deg C. Miscible in all proportions with acetone, ethanol, ethyl acetate, methylene chloride.

0-6°C

1.20X10-7 mm Hg at 25 deg C

Faint petroleum odor

pH of 1% aqueous solution = 5.8

Henry's Law constant = 3.0X10-9 atm-cu m/mol at 25 °C (est)

179.54 Ų [M+H]+

Hydroxyl radical reaction rate constant = 5.0X10-12 cu cm/molecule-sec at 25 °C (est)

UN30829/PG3

50/53

60-61

DA8343383

N

Hydrolytic DT50 3.6 hr (pH 9), 8.6 days (pH 7), stable (pH 5). Aqueous photolytic DT50 8 days.

P273-P501

H410

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|For End-Use Products the following language should be stated: "Carfentrazone-ethyl is very toxic to aquatic plants and moderately toxic to fish. Do not apply directly to water, to areas where surface water is present or to intertidal areas below the high water mark, except as specified on this label. Do not contaminate water when disposing of equipment washwaters."|For Manufacturing-use products the following language should be stated: "Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans or public waters unless this product is specifically identified and addressed in an NPDES permit. Do not discharge effluent containing this product to sewer systems without previously notifying the sewage treatment plant authority. For guidance, contact your State Water Board or Regional office of the EPA."

|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|Aggregated GHS information provided by 164 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]|Danger|H331: Toxic if inhaled [Danger Acute toxicity, inhalation]|P261, P271, P273, P304+P340, P311, P321, P391, P403+P233, P405, and P501|H373: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]|P260, P273, P314, P391, and P501

Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Handle with gloves.|Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Where risk assessment shows air-purifying respirators ar appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Wear self contained breathing apparatus for fire fighting if necessary.

Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas...|Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.

IDENTIFICATION AND USE: Carfentrazone-ethyl is a viscous yellow-orange liquid with a faint petroleum odor. It is registered for pesticide use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. It is used as a postemergent, contact herbicide for controlling broadleaf weeds; as a defoliant in cotton; and it provided a good control of hazelnut shoots. It is also used for turf and ornamentals. HUMAN EXPOSURE AND TOXICITY: There is no published data available on the toxicity in humans. ANIMAL STUDIES: Ninety-day subchronic feeding studies resulted in decreases in body weight, reductions in food consumption and histopathological lesions in rats; liver pathology in mice; and decrease in the rate of weight gain in females and an increase in urinary porphyrins in both sexes of dogs. Carfentrazone-ethyl was found to be non-carcinogenic when administered for 18 months to mice at dietary intake doses of 0, 10, 110 and 1090 mg/kg/day for males and 0, 12, 119 and 1296 mg/kg/day for females and in a 2-year rat chronic toxicity/carcinogenicity study conducted in rats at intake levels of 0, 2, 9, 37 and 188 mg/kg/day for males and 0, 3, 12, 49 and 242 mg/kg/day for females. A developmental toxicity study in rabbits was conducted at gavage dose levels of 0, 10, 40, 150 and 300 mg/kg/day. Evidence of treatment-related maternal toxicity consisted of unthriftiness and emaciation in two does at 300 mg/kg/day. There were no treatment-related mortalities or gross pathological findings. No effects on body weight, body weight change, or organ weight data were identified at any treatment level. A two-generation reproduction study in the rat was conducted with dietary levels of 0, 8.6, 42.4, 127, 343 mg/kg/day for males, and 0, 9.5, 47.8, 142, and 387 mg/kg/day for females. There was no systemic toxicity demonstrated at dose levels of less than/equal to 1500 ppm. There were no treatment related clinical signs of toxicity or increases in mortality at any dose levels. There were no clinical signs of toxicity reported for the pups of either generation. Carfentrazone-ethyl was negative for genotoxicity in two reverse gene mutation assays (Salmonella typhimurium), both with and without metabolic activation. Mammalian cell forward gene mutation assay in CHO cells in vitro yielded negative results both with and without activation. An in vitro chromosomal aberration assay yielded positive results under non-activated conditions following doses of 3.75, 12.5, 37.5 and 125 ug/mL. There were consistent and statistically significant increased incidences of cells with aberrations at 125 ug/mL, the highest dose tested in the absence of metabolic activation.

LD50 Rat (female) oral 5143 mg/kg|LD50 Rat dermal >4000 mg/kg|LC50 Rat inhalation 5.09 mg/L/4 hr

Carfentrazone-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), Koc values of 15-35 at pH 5.5 and 750 (pH not specified)(2) indicate that carfentrazone-ethyl is expected to have very high mobility in acid soil and low mobility in neutral or basic soils(SRC). Volatilization of carfentrazone-ethyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 1.2X10-7 mm Hg(2), and water solubility, 22 mg/L(2). Carfentrazone-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Measured half-lives of carfentrazone-ethyl in Beijing and Jilin, China soil samples collected during a wheat field dissipation study were reported as 5.8 and 3.8 hours, respectively(3). The route of dissipation was not reported(3), however, based on other field studies, chemical hydrolysis is expected to be the primary route of degradation(4-5). These degradation rates indicating that biodegradation is not expected to compete with the hydrolysis of carfentrazone-ethyl, especially under neutral or basic conditions(4-5).|TERRESTRIAL FATE: Dissipation and residues of carfentrazone-ethyl were measured after field application in Beijing and Jilin, China, at respective rates of 120 and 600 g/100 sq m (g/hm2)(1). The half-life for carfentrazone-ethyl was 5.8 and 3.8 hours at the respective locations(1).[Table#6866]|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 750(2) indicates that carfentrazone-ethyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.2X10-7 mm Hg(2), and water solubility, 22 mg/L(2). Carfentrazone-ethyl had reported hydrolysis half-lives of 131 and 3.4 hours at respective pH values of 7.09 and 9.09(4). Only 43% of the substance was hydrolyzed after 830 hours at pH 5.17(4). According to a classification scheme(5), an estimated BCF of 77(SRC), from its log Kow of 3.36(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). The half-lives of carfentrazone-ethyl in the water layer above aquatic sediments ranged from 1.0-1.5 days in a separate study(7). Chemical hydrolysis was the primary route of degradation, indicating that biodegradation is not expected to compete with the hydrolysis of carfentrazone-ethyl, especially under neutral or basic conditions(4,7).|AQUATIC FATE: The degradation of radio labeled carfentrazone-ethyl was tested in flooded sediment (silty clay loam and clay loam soils)(1). Following application to the water layer, the radioactivity slowly transferred to the sediment layer. Percent radioactivity in the aqueous layers fell from 83-90% at zero time to 70-80% after 30 days while percent radioactivity in the soil layers rose from 4-6% at day zero to 13-19% after 30 days. primary degradation pathway was chemical hydrolysis to carfentrazone-chloropropionic acid which is then further degraded to carfentrazone -cinnamic, -propionic, -benzoic and 3-(hydroxymethyl)-carfentrazone-benzoic acids. The concentration of radio-labeled carfentrazone-ethyl (CF-E) and its major degradation product, carfentrazone-chloropropionic acid (CF-CIPAc), are reported below in two types of soil(1).[Table#6867]|For more Environmental Fate (Complete) data for CARFENTRAZONE-ETHYL (6 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of carfentrazone-ethyl with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis half-lives of 131 and 3.4 hours were measured for carfentrazone-ethyl at respective pHs of 7.09 and 9.09(2). Only 43% of the substance was hydrolyzed after 830 hours at pH 5.17(2). The primary hydrolysis degradation pathway for carfentrazone-ethyl is to carfentrazone-chloropropionic acid which is then further degraded to a series of acidic products(2). Carfentrazone-ethyl was considered largely stable to direct UV photosynthesis in aqueous pH7 buffer with a half-life of 113 hours (dark control 128 hours)(2). A direct aqueous photolysis half-life of 8 days has also been reported(3-4).

An estimated BCF of 77 was calculated in fish for carfentrazone-ethyl(SRC), using a log Kow of 3.36(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).

A Koc value of 750 (pH not specified) and 15-35 at pH 5.5 have been reported(1). According to a classification scheme(2), these Koc values suggest that carfentrazone-ethyl is expected to have very high mobility in acid soil and low mobility in neutral or basic soils(SRC).

The Henry's Law constant for carfentrazone-ethyl is estimated as 3.0X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 1.2X10-7 mm Hg(1), and water solubility, 22 mg/L(1). This Henry's Law constant indicates that carfentrazone-ethyl is expected to be essentially nonvolatile from moist soil or water surfaces(2). Carfentrazone-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Carfentrazone-ethyl was not detected (detection limit 0.050 ppm) in commercially grown hops(1).

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

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

A metabolism study in rats indicated that approximately 72.4-87% of the administered dose of carefentrazone-ethyl was rapidly absorbed and excreted in the urine within 24 hr after dosing.

A metabolism study in rats indicated ...the major metabolites in both the urine and feces were F8426-chloropropionic acid (48.4-66.06%). The proposed metabolic pathway appeared to be the conversion of the parent compound by hydrolysis of the ester moiety to form F8426-chloropropionic acid, followed by oxidative hydroxylation of the methyl group to form 3-hydroxymethyl-F8426-chloropropionic acid, or dehydrochlorination to form F8426-cinnamic acid.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilation if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Esters and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

((14)C)carfentrazone-ethyl

The National Pesticide Information Retrieval System (NPIRS) identifies 5 companies with active labels for products containing the chemical carfentrazone-ethyl. To view the complete list of companies, product names and percent carfentrazone-ethyl in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.|Aim 50 DF Herbicide (FMC Corp, Agricultural Products Group): Active Ingredient: Carfentrazone-ethyl 50.0%.|Cyclone Star (Syngenta Crop Protection, LLC): Active ingredient: Paraquat dichloride 30.1%; Carfentrazone-ethyl 22.3%.|Mon 78481 Herbicide (Monsanto Company): Active ingredient: Glycine, N-(phosphonomethyl)- potassium salt 44.76%; Carfentrazone-ethyl 0.19%.|For more Formulations/Preparations (Complete) data for CARFENTRAZONE-ETHYL (34 total), please visit the HSDB record page.

Analytical Enforcement Methodology: There is a practical analytical method for detecting and measuring levels of carfentrazone-ethyl and its metabolites in or on food with a limit of detection that allows monitoring of food with residues at or above the levels set in these tolerances. The proposed analytical method for determining residues is hydrolysis followed by gas chromatographic separation.

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

Carfentrazone-ethyl has known environmental transformation products that include 3-hydroxymethyl-F8246-propionic acid, 3-hydroxymethyl-F8426-benzoic acid, 3-hydroxymethyl-F8426-chloropropionic acid, F8246-dicarboxylic acid, F8426-benzoic acid, F8426-chloropropionic acid, F8426-cinnamic acid, F8426-propionic acid, FMC185655 , Methoxy-F8246-despropionate, and alpha,2-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorobenzenepropanoic acid.