Piperalin

330.25

330.25

222-455-6

DTXSID7032634

Viscous amber liquid

2933399090

29.5

4.31 (pH 5, 7, 9; 21 deg C)

1.18 g/cm³

208 °C (decomp)

156-157 °C @ Press: 20 Torr

76 °C

1.534

In water, 20 mg/l, temp not specified

Slightly musty straw odor

A 50% slurry has a pH of 9.0

pKa = 8.9 (in 66% DMF)

71.1 °C (freezing point)

UN30829/PG3

38-50/53

60-61

DG7700000

Xi,N

Stable to heat, to metal and metal ions for 28 days at 50 deg C and stable in storage at room temperature up to about seven years.

P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, P501

H315

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Piperalin EPA 738-R-94-033 September 1994. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 6, 2003: http://www.epa.gov/pesticides/reregistration/status.htm]

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, and P501|Aggregated GHS information provided by 127 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

LD50 Rat (female) oral 800 mg/kg[|LD50 Rat (male) oral 1419 mg/kg[|LD50 Rabbit dermal >5850 mg/L[

/BIRDS and MAMMALS/ Avian and mammalian species will not be significantly exposed to piperalin through the consumption of insect and plant food material containing residues of the chemical... . Based on the available acute toxicity data, piperalin is practically non-toxic to birds. In addition, no significant exposure is expected from the greenhouse use of this chemical... .|/AQUATIC SPECIES/ Based on the available acute toxicity data, piperalin is highly toxic to fish and moderately toxic to aquatic invertebrates. Exposure to nontarget fish and aquatic invertebrates is not expected to occur from the proposed use of the chemical... . No significant risks to endangered species are expected from the greenhouse use of piperalin.

Piperalin's production may result in its release to the environment through various waste streams; it's use as a fungicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Piperalin has a pKa of 8.9(2) indicating that this compound will exist primarily as a cation under environmental conditions(SRC). Based on a classification scheme(1), Koc values ranging from 5000 to 45,000(2) indicate that piperalin is expected to be immobile in soil(SRC). Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(7). Volatilization from moist soil surfaces is not expected to be an important fate process for ionized piperalin(SRC). Volatilization of the neutral species from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Piperalin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-5 mm Hg(SRC), determined from a fragment constant method(4). Hydrolysis, particularly in alkaline soils, may be an important fate process(SRC); half-lives of 4.8 hours, 16.4 days, and 714 days were reported for piperalin at pH values of 9, 7, and 5, respectively(5). Major hydrolysis products (both microbial and chemical) are dichlorobenzoic acid and 3-(2-methylpiperi-dino)propyl alcohol(5). Piperalin is slowly biodegraded with an aerobic half-life range of 96 to 100 days in a sandy loam soil (pH 5.5)(5). If piperalin is initially subjected to aerobic biodegradation followed by anaerobic conditions, half-lives of 33.8 and 38.1 days are reported for the anaerobic portion of the study(5). A field dissipation half-life of 30 days has been reported(6).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 5000 to 45,000(2), indicate that piperalin is expected to adsorb to suspended solids and sediment(SRC). The pKa of piperalin is 8.9(8), indicating that this compound will primarily exist in cation form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). Volatilization from water surfaces is not expected to be an important fate process for ionized piperalin(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 420(SRC) for the neutral species, from a log Kow of 4.31(7), suggests the potential for bioconcentration of the neutral species in aquatic organisms is high (SRC). Hydrolysis, particularly in alkaline waters, may be an important fate process(SRC); half-lives of 4.8 hours, 16.4 days, and 714 days were reported for piperalin at pH values of 9, 7, and 5, respectively(8). Major hydrolysis products are dichlorobenzoic acid and 3-(2-methylpiperi-dino)propyl alcohol(8). Although biodegradation studies conducted in water environments are not available, piperalin is slowly biodegraded with an aerobic half-life range of 96 to 100 days in a sandy loam soil (pH 5.5)(8). Under anaerobic conditions using the same soil, biodegradation proceeds more quickly(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), piperalin, which has an estimated vapor pressure of 1.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase piperalin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.3 hours(SRC), calculated from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase piperalin may be removed from the air by wet and dry deposition(SRC).

Hydrolysis half-lives of 4.8 hours, 16.4 days, and 714 days were measured at pH 9, 7, and 5, respectively, at 25 °C; dichlorobenzoic acid and 3-(2-methylpiperidino)propyl alcohol were reported as the major degradates of this process(1). Photolysis half-lives of >30 days and 35 days(first-order rate constants of <0.023 and 0.02 per day) in water and soil, respectively, were reported for piperalin(2). The rate constant for the vapor-phase reaction of piperalin with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(3). This corresponds to an atmospheric half-life of about 3.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(3).

The pKa of piperalin is 8.9(4), indicating that this compound will primarily exist as a cation in the environment. An estimated BCF of 420 was calculated for the neutral species of piperalin(SRC), using a log Kow of 4.31(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration of the neutral species in aquatic organisms is high(SRC).

5.01e+03 L/kg|Measured Koc values of 5000, 9600(Kd=27.6, 0.5% organic matter, pH 7.7, sand soil), 7,700 (Kd=62.3, 1.4% organic matter, pH 5.7, sandy loam soil), 29,300 (Kd=305, 1.8% organic matter, pH 6.5, loam soil), and 45,000 (Kd=520, 2.0% organic matter, pH 6.9, clay loam soil) have been reported(1). According to a classification scheme(2), these Koc values suggest that piperalin is expected to be immobile in soil. The pKa of piperalin is 8.9(4), indicating that this compound will primarily exist as a cation and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(3).

The pKa of piperalin is 8.9(4), indicating that this compound will primarily exist in cation form in the environment. Volatilization from moist soil or water surfaces is not expected to be an important fate process for ionized piperalin(SRC). The Henry's Law constant for the neutral species is estimated as 2.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1) indicating that nonionized piperalin is expected to be essentially nonvolatile from water(2) and moist soil surfaces(SRC). Piperalin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to piperalin may occur through dermal contact with this compound at workplaces where piperalin is produced or used. (SRC)

Piperalin is a fungicide used for the control of powdery mildews on ornamentals... /and/ is a potent inhibitor of growth and ergosterol biosynthesis in sporidia of Ustilago maydis...|Microdochium nivale, a wheat pathogenic filamentous fungus, appeared to be ... sensitive in in vivo laboratory assays to ... piperalin ... . It accumulated 8-sterols when grown in the presence of ... /piperilin/ ... Thus, in M. nivale, /piperilin/... seemed to be /a/ ... good inhibitor of the sterol 8 7-isomerase. This hypothesis was then confirmed by sterol 8 7-isomerase inhibition assays in cell-free enzyme systems.

Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

USEPA/OPP Pesticide Code 097003; Trade Names: Pipron.

Agrochemicals -> Fungicides|FUNGICIDES