Diflufenzopyr

334.28

334.28

600-910-3

DTXSID8034538

Off-white powder, solid|Off-white solid

2933399090

103.68000

3.06760

0.24 g/cm³ @ Temp: 25 °C

155 °C (decomp)

150 °C

1.612

1.88e-04 M|In water, 63 mg/L (pH 5), 5850 mg/L (pH 7), and 10546 mg/L (pH 9)

0-6°C

VP: 1.0X10-7 kPa at 20 °C and 25 °C|less than 1.3X10-5 Pa /7.50X10-8 mm Hg/ at 20 °C

LD50 in rats (mg/kg): >5000 orally; >5000 dermally; LC50 in rats (mg/l): 2.93 by inhalation; LC50 in rainbow trout, bluegill sunfish (mg/l): 106, 135 (Bowe).

Odorless

pKa = 3.18

US5648931

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Diflufenzopyr (January 28, 1999).[Available from, as of June 1, 2011: http://www.epa.gov/opprd001/factsheets/]

|Warning|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 156 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

For several good reasons, .... herbicides ... should be handled and applied only with full attention to safety measures that minimize personal contact. Many formulations contain adjuvants (stabilizers, penetrants, surfactants) that may have significant irritating and toxic effects. A number of premixed formulations contain two or more active ingredients; the companion pesticides may be more toxic than the principal herbicide. Good hygienic practice should not be disregarded just because a pesticide is reported to have a high LD50 in laboratory rodents. /Herbicides/

LD50 Rat oral >5000 mg/kg /Diflufenzopyr technical/|LD50 Rabbit dermal >5000 mg/kg|LD50 Rat oral (male) 4800 mg/kg /Diflufenzopyr manufacturing use product/|LD50 Rat oral (female) 3300 mg/kg /Diflufenzopyr manufacturing use product/

Diflufenzopyr's production may result in its release to the environment through various waste streams; it's 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 19 to 156(2) indicate that diflufenzopyr is expected to have very high mobility in soil(SRC). The pKa of diflufenzopyr is 3.18(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and ions do not volatilize. Diflufenzopyr is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <9.7X10-8 mm Hg at 20 °C(5). A biodegradation half-life in soil of 8-10 days(2) suggests that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 18 to 156(2) indicate that diflufenzopyr is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.18(3) indicates diflufenzopyr will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of 1.09(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). An aquatic biodegradation half-life of 25-26 days(2) suggests that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diflufenzopyr, which has a vapor pressure of less than 9.75X10-8 mm Hg at 20 °C(2), will exist primarily in the particulate phase in the ambient atmosphere. Particulate-phase diflufenzopyr may be removed from the air by wet and dry deposition(SRC). Diflufenzopyr contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).

The aqueous hydrolysis half-life of diflufenzopyr is 13 days at pH 5, 24 days at pH 7, and 26 days at pH 9. The photolysis half-life in water is 7 days at pH 5, 17 days at pH 7, and 13 days at pH 9. The photolysis half-life on soil is 14 days(1).

An estimated BCF of 3 was calculated for diflufenzopyr(SRC), using an experimental log Kow of 1.09(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Diflufenzopyr has measured Koc values of 18 to 156(1). According to a classification scheme(2), these Koc values suggest that diflufenzopyr is expected to have very high mobility in soil.

A pKa of 3.18(1) indicates diflufenzopyr will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. Diflufenzopyr is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <9.7X10-8 mm Hg(2).

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

Following oral administration /in rats/, Diflufenzopyr was partially absorbed and rapidly eliminated; 20-40% of the dose was eliminated in urine and 49-79% in feces. By contrast, intravenously dosed rats excreted 61-89% of the dose in urine. Elimination /half-time/ in urine and feces was 6 hr.|A metabolism study of diflufenzopyr was conducted in laying hens and lactating goats. The data showed diflufenzopyr was rapidly eliminated from the animals. With a feeding level of 10 ppm in the diet, residue levels in edible tissues, milk, and eggs were less than 0.12 ppm. ...|Wistar rats were administered (14)C-labeled Diflufenzopyr (SAN 835 H phenyl-labeled: radiochemical purity > 98%; pyridinyllabeled: radiochemical purity > 98%; unlabeled test article purity = 99.4%) according to each of four protocols: 1) a single i.v. dose at 1 mg/kg, 2) a single oral dose at 10 mg/kg, 3) a single oral dose at 1000 mg/kg, 4) fourteen daily oral doses of unlabeled test article at10 mg/kg followed by a single oral dose of labeled compound at 10 mg/kg. For protocols 1, 2 and 3, five males and five females were monitored according to each of 3 schedules: a) until sacrifice at 72 hrs post-dosing, b) until sacrifice at 24 hrs post-dosing, c) bile-duct cannulated animals followed until sacrifice at 48 hrs post-dosing. For the repeated dosing protocol, five males and five females were sacrificed at 24 hrs and 72 hrs after dosing with the labeled test article. Intravenous administration led to rapid elimination in the urine of between approximately 58 and 68% of both labeled forms by 7 hrs, and between 70 and 90% by 72 hrs. Of the approximate 7-20% excreted in the feces, almost all was a result of bilary excretion. Oral dosing at both 10 and 1000 mg/kg resulted in elimination of both labels mainly through the feces (approximately 55-80% by 72 hrs). Excretion in the urine accounted for approximately 20-39%, with approximately 3-10% excreted in the bile. Tissue retention at 72 hrs was low after either intravenous or oral dosing, being 0.37% or less for the phenyl-labeled compound (highest in blood) and 0.04% or less for the pyridinyl compound (highest in kidney and liver). The percent absorption for both labeled compounds, calculated by dividing the amount of labeled compound excreted in the urine after oral dosing by the amount excreted in the urine after i.v. dosing, was between 30 and 50%, with no difference between the 10 and 1000 mg/kg dose levels. ... There were no significant differences in test article absorption, elimination, tissue distribution or metabolism by males versus females. Likewise, high and low dose levels gave similar results, suggesting no saturation for absorption or elimination. There was less tissue retention of the pyridinyl-labeled compound and greater retention of the phenyl-labeled compound in the blood. Lastly, single versus multiple dosing showed that the test article did not bioaccumulate or induce metabolizing enzymes.

Metabolite analysis of the urine, bile and feces was conducted by TLC, HPLC, mass spectrometry and NMR spectroscopy. Unaltered test article was the major labeled compound in all excreta. Major metabolic reactions included cyclization, hydrolysis and hydroxylation, yielding 7 major metabolites (M1, M2, M5, M6, M9, M10 and M19). M19, M10 and M9 were also identified in excreta from goats and hens, and in corn silage.

Wistar rats were administered (14)C-labeled Diflufenzopyr (SAN 835 H phenyl-labeled: radiochemical purity > 98%; pyridinyllabeled: radiochemical purity > 98%; unlabeled test article purity = 99.4%) ... Elimination rates followed a one compartmental model, yielding an average half-time of 6.3 hrs for all groups combined. Elimination rates were not different between dose levels, or between the two different labels.

/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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 ... . Anticipate seizures 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

diflufenzopyr

Wettable granular|Premix Partners: Dicamba; Nicosulfuron|99% Technical product (acid); 93% manufacturing use product (sodium salt); wettable granular end use product containing 21.4% sodium diflufenzopyr and 55% sodium dicamba.|Diflufenzopyr Technical Herbicide (Basf Corporation) Diflufenzopyr 99.1%

Use rates on field corn range from 4 to 8 ounces of formulated product ... the maximum number of applications per season is two with a total of no more than 10 ounces product.

Adequate enforcement methodology (gas chromatography) is available to enforce the tolerance expression.|Residues by GC/MS. In soil by HPLC/UV-GC/MS.

Agrochemicals -> Herbicides