Piprotal

456.576

456.57

C01EGF4W4Q

195166

DTXSID0042296

2932999099

73.8

4.11370

1.03 g/cm³ @ Temp: 25 °C

190-200 °C @ Press: 2 x 10^-3 Torr

197.6ºC

1.492

In water, 186 mg/L 25 °C (est)

4.21X10-10 mm Hg at 25 °C (est)

Henry's Law constant = 1.52X10-15 atm-cu m/mol at 25 °C (est)

When heated to decomposition it emits acrid smoke and irritating fumes

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.

Occupational exposure and general population exposure should be low or non-existent since piprotal is no longer produced or used. (SRC)

IDENTIFICATION AND USE: Piprotal is a former synergist for pyrethrum and carbamate insecticides, which is discontinued. HUMAN STUDIES: Although piprotal is not a serious toxic hazard to man, large doses may, by inhibiting detoxification mechanism, render a person temporarily susceptible to other chemical insults that would normally be tolerated with ease. ANIMAL STUDIES: The effects of piprotal on oxidative phosphorylation were investigated in vitro in mitochondria isolated from the livers of male rats. Piprotal inhibited state 3 respiration and the ADP/oxygen ratio. The effects of insecticide synergists were assayed with respect to in vivo inhibition on two hydroxylating systems of mouse liver microsomes, using dimethylaminopyrine and hexobarbital as substrates. Piprotal showed weak inhibition.

The duration of the hexobarbital (HB) sleeping times (HST) and the acute toxicities of 10 organophosphorus insecticides were determined in male Swiss-Webster-mice. All compounds were given intraperitoneally. The HST, at a dose of 125 milligrams per kilogram (mg/kg) HB was measured by recording the duration between loss and recovery of the righting reflex. Acute toxicities were determined over a 24 hour period following administration of several doses of each compound. Enzymatic cleavage of parathion and methyl-parathion were assayed in-vitro on mouse liver after pretreatment with 400 mg/kg piperonyl-butoxide (PB) and tropital (TP). The HSTs were significantly increased when HB was given 12 hours or less after a single intraperitoneal dose of 200 mg/kg PB, but were decreased when HB was administered 24 or 48 hours after PB. When a single dose of 6.25 mg/kg PB was given, it prolonged HST at 30 minutes after the synergist was given, but a dose of 100 mg/kg PB was required to significantly shorten the HST at 48 hours after the synergist was given. Similar dose related effects on HST were found with TP treated mice except that 4 fold greater doses were required to produce equivalent shortening or prolongation of HST. Mice were protected against the acute toxicities of methyl-parathion, guthion and dimethoate 1 hour following the administration of 400mg/kg PB, but they were more susceptible to parathion and ethyl-guthion toxicity at the same dose. Mice became more susceptible to dimethoate 48 hours after PB administration, but were protected against the other compounds at this time. The cleavage of parathion and methyl-parathion by the mouse liver enzymes was inhibited at 1 hour after PB administration, but was increased at 48 hours. The authors discuss the possible mechanism of interaction of the synergists and the insecticides.

LD50 Rat oral about 4400 mg/kg

Proptal's former production and use as an insecticide synergist(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 190(SRC), determined from a structure estimation method(2), indicates that piprotal is expected to have moderate mobility in soil(SRC). Volatilization of piprotal from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Piprotal is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.2X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2018).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 190(SRC), determined from a structure estimation method(2), indicates that piprotal 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 1.5X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 75(SRC), from an estimated log Kow of 3.35(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), piprotal, which has an estimated vapor pressure of 4.2X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase piprotal may be removed from the air by wet and dry deposition(SRC). Piprotal does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Piprotal is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Piprotal does not contain chromophores that absorb at wavelengths >290 nm(1) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 75 was calculated in fish for piprotal(SRC), using an estimated log Kow of 3.35(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of piprotal can be estimated to be 190(SRC). According to a classification scheme(2), this estimated Koc value suggests that piprotal is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for piprotal is estimated as 1.5X10-15 atm-cu m/mole(SRC) developed using a fragment constant estimation method(1). This Henry's Law constant indicates that piprotal is expected to be essentially nonvolatile from water and moist soil surfaces(2). Piprotal is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.2X10-10 mm Hg(SRC), determined from a fragment constant method(1).

When Tropital was fed to mice, rats or hamsters, degradation occurred primarily at the side chain with excretion of metabolites in the urine.|... mice excreted 98% of ... /oral/ dose of Tropital in the urine ...|Methylenedioxphenyl synergists, piperonyl butoxide, Tropital and octachlorodipropyl ether are used as synergists for a variety of pesticides as well as functioning as inhibitors of the epoxidation of aldrin to dieldrin. the nature of the biliary and urinary metabolites following single i.v. administration of the synergists as well as their mode of separation and detection is illustrated. The rate of elimination of the biliary metabolites, although high, does not reach a rapid peak followed by a rapid decline, but suggests prolonged elimination of the metabolites from the body into the bile. ...

Methylenedioxphenyl synergists, piperonyl butoxide, Tropital and octachlorodipropyl ether are used as synergists for a variety of pesticides as well as functioning as inhibitors of the epoxidation of aldrin to dieldrin. the nature of the biliary and urinary metabolites following single i.v. administration of the synergists as well as their mode of separation and detection is illustrated. The rate of elimination of the biliary metabolites, although high, does not reach a rapid peak followed by a rapid decline, but suggests prolonged elimination of the metabolites from the body into the bile. ...|When Tropital was fed to mice, rats or hamsters, degradation occurred primarily at the side chain with excretion of metobolites in the urine. Some metabolism of the methylene dioxide to carbon dioxide also occurred. The glycine and glucuronate conjugates were found. Rats, mice and rabbits, admin Tropital orally, metabolized the Tropital to piperonal, piperonylic acid, N-piperonyglycine and two unidentified acid cmpd. When piperonylic acid was fed to mice, both the free acid and glycine conjugate were observed. After incubation of tropital with mouse liver microsomes and NADPH2, Tropital was degraded to piperonylic acid via piperonal.|The metabolism of methylenedioxyphenyl (MDP) compounds was studied in mammals. The purpose of the study was to investigate the mechanism and significance of demethylation of MDP and similar compounds in relation to the metabolism and mode of action of commercial synergist chemicals such as piperonyl-butoxide and tropital. Male Swiss-Webster-mice, Sprague-Dawley-rats, or hamsters were administered 13 carbon-14 labeled MDP compounds such as tropital, piperonal, piperonyl-alcohol, piperonylic-acid, safrole, dihydrosafrole, or piperonyl-butoxide. Urine, feces, and expired air were collected for 48 hours for carbon-14 assay. Carbon-14 activity in the intestine, liver, and carcass was determined. Urine samples were analyzed for metabolites. Compounds such as dihydrosafrole, safrole, myristicin, and piperonyl-butoxide were largely metabolized by oxidation of the methylene group of the MDP moiety to yield radiolabeled carbon-dioxide. The radiolabel ultimately appearing as carbon-dioxide was first liberated as radioactive formate. Carbon-dioxide was not an important route of elimination in the metabolism of piperonyl-alcohol, piperonal, piperonylic-acid, and tropital. Their metabolites were excreted primarily in the urine. No marked species difference was noted in carbon-14 tissue distribution after dosing with tropital and piperonyl-butoxide. Oxidation or conjugation of the side chain was the major metabolic pathway for tropital, piperonal, piperonyl-alcohol, and piperonylic-acid. Urinary metabolites of piperonyl-butoxide included many compounds lacking the MDP moiety and small amounts of 6-propyl-piperonylic-acid and its glycine conjugate. Urinary metabolites of tropital included glycine and glucuronic-acid conjugates of piperonylic-acid. In an in-vitro experiment, radiolabeled piperonyl-butoxide, tropital, safrole, and other MDP compounds were incubated with mouse liver microsomes and were assayed for metabolites. Metabolites such as formate and catechols were detected. The authors conclude that demethylation of the MDP moiety is the major metabolic pathway in mammals given piperonyl-butoxide, safrole, dihydrosafrole and myristicin.

/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 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 TKO /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. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Discontinued by McLaughlin Gormley King Co|Pesticide /Former US/