Trifenmorph

329.443

329.43

215-812-2

H1IL51K9CW

DTXSID6042492

Crystals from ethanol|Colorless crystalline solid

29349990

12.5

4.21 (est)

1.0859 (rough estimate)

174-176 °C

467.03°C (rough estimate)

126.5ºC

1.5614 (estimate)

At 20 deg C (g/L): carbon tetrachloride 300; chloroform 450; tetrachloroethylene 255

2.8X10-8 mm Hg at 25 deg C (est)

LD50 orally in rats: 1200-2000 mg/kg (Boyce)

Henry's Law constant = 1.32X10-10 atm-cu m/mol at 25 °C (est)

Stable to heat and alkali but hydrolyzed by mild acidic conditions to morpholine and triphenylmethanol|Light brown crystals, 90-95% pure /Technical grade/|Hydroxyl radical reaction rate constant = 1.54X10-10 cu cm/molec-sec at 25 °C (est)

Non-corrosive

III

6.1(b)

3249

22-50/53

60-61

Xn,N

IT IS STABLE TO HEAT & ALKALIES, BUT IS HYDROLYZED BY MILD ACID CONDITIONS TO MORPHOLINE & TRIPHENYLMETHANOL. SLIGHT DECOMPOSITION OCCURS IN UV LIGHT.

P264, P270, P273, P301+P312, P330, P391, P501

H302

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.|Residues in containers should be emptied in a diluted form into a deep pit taking care to avoid ground waters. The empty container may be decontaminated by rinsing two or three times with water and detergent and scrubbing the sides. The hands should be protected during this work. Decontaminated containers should not be used for any other purpose.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501

When opening a container and when mixing, protective impermeable boots, clean overalls, impermeable gloves and a respirator should be worn.|Closed systems and forced ventilation may be required to reduce, as much as possible, the exposure of workers to the chemical.

Mixing, if not mechanical, should always be carried out with a paddle of appropriate length. Avoid contact with mouth and eyes. Before eating, drinking or smoking, hands and other exposed skin should be thoroughly washed with alkaline soap.|Keep /technical trifenmorph/ away from foodstuffs and animal feeds.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

LD50 Rat dermal 1000 mg/kg bw|LD50 Mouse oral 700-4800 mg/kg|LD50 Rat oral 1200-1600 mg/kg (in organic solvents)|LD50 Rat oral 100-200 mg/kg (in chlorinated solvents)

/AQUATIC SPECIES/ Fish were killed in canals treated for 6 hr with frescon to yield concentration of 0.1 ppm.|/AQUATIC SPECIES/ ... Aquatic micro-flora and -fauna were uneffected at 0.2 ppm.|/AQUATIC SPECIES/ /Trifenmorph/ above 0.03 ppm /may be/ harmful to fish.|/OTHER TOXICITY INFORMATION/ /N-tritylmorpholine/ is highly specific, being harmless to plants, insects, and most vertebrates, though it is moderately toxic to some species of fish.

Trifenmorph's former production may have resulted in its release to the environment through various waste streams; its former use as a molluscicide(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.7X10+5(SRC), determined from a structure estimation method(2), indicates that trifenmorph is expected to be immobile in soil(SRC). Volatilization of trifenmorph from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Trifenmorph is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). In soil within a few weeks, trifenmorph is aerobically converted to triphenyl methanol which undergoes slow hydroxylation(5).|TERRESTRIAL FATE: Half of N-tritylmorpholine applied to soil was lost in 1 to 4 weeks.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.7X10+5(SRC), determined from a structure estimation method(2), indicates that trifenmorph 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 1.3X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 280(SRC), from an estimated log Kow of 4.21(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Under mild acid conditions, trifenmorph is hydrolyzed to morpholine and triphenylmethanol(3). Biodegradation is not an important environmental fate process in water(SRC) based on the slow rate reported for soil(7).|AQUATIC FATE: The fate of the molluscicide trifenmorph (N-tritylmorpholine) following its use in irrigation systems to control the intermediate hosts of schistosomes was studied by laboratory and field experiments. Laboratory studies with 14C-trifenmorph indicated that bean plants did not take up detectable residues when the soil in which they were grown was irrigated with water containing trifenmorph in concentrations likely to occur in the field. These laboratory studies have been complemented by field irrigation studies of growing crops in southern Africa and the Sudan. Residues of trifenmorph and its breakdown product triphenylmethanol could not be detected in the crops and the limit of detectability was 0.01-0.02 ppm. These results indicate that residues are not likely to be present in irrigated crops following the treatment of the irrigation water systems with trifenmorph(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trifenmorph, which has an estimated vapor pressure of 2.8X10-8 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 trifenmorph 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 2.5 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase trifenmorph may be removed from the air by wet or dry deposition(SRC). Slight decomposition occurs in UV light(4).

The rate constant for the vapor-phase reaction of trifenmorph with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate of hydrolysis of 14C-trifenmorph is dependent on the pH of the water (relatively high at low pH values of <7.0) and concentration of the compound(2). Under mild acidic conditions, trifenmorph is hydrolyzed to morpholine and triphenylmethanol(4). Mud and sediment gradually adsorb trifenmorph and carbinol(3). Slight decomposition occurs in UV light(3).|The rate of hydrolysis of 14C-trifenmorph is dependent on the pH of the water (relatively high at low pH values of <7.0) and concentration of the compound(1).

An estimated BCF of 280 was calculated in fish for trifenmorph(SRC), using an estimated log Kow of 4.21(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).|Sarotherodon mossambicus /Mozambique talapia/, juvenile, exhibited a bioconcentration factor of 1,300 after 55 hr.|Bioconcentration factor = 5,600 (calculated from water solubility by regression equations). /From table/

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trifenmorph can be estimated to be 3.7X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that trifenmorph is expected to be immobile in soil.|KOC = 37,500 (calculated from water solubility by regression equations). /From table/

The Henry's Law constant for trifenmorph is estimated as 1.3X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trifenmorph is expected to be essentially nonvolatile from water and moist soil surfaces(2). Trifenmorph is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-8 mm Hg(SRC), determined from a fragment constant method(3).

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

In dogs, rats and mice /trifenmorph/ was rapidly metabolized by gastrointestinal enzymes to triphenylcarbinol, and morpholine. Triphenylcarbinol was absorbed slowly and it was oxidized by hepatic systems to para-hydroxyphenyldiphenylcarbinol and also, ortho- and meta-hydroxytriphenylcarbinols to a lesser extent. Morpholine was rapidly absorbed and excreted in the urine unchanged as a glucuronic acid conjugate. Triphenylcarbinol and its hydroxy derivatives were found in urine and feces as free compounds and in three glucuronide fractions; diglucuronides, carbinol-group glucuronide and phenolic-groups glucuronides. In (14)C-labelled tracer dose studies no (14)CO2 was respired and, after 96 hours only 3% of the radioactivity remained in the carcass.

Rats and dogs were given (14)C labeled frescon as single oral doses. Frescon rapidly hydrolyzed to triphenylcarbinol and morpholine in the stomach. Morpholine was rapidly absorbed and excreted largely unchanged though some was degraded. Triphenylcarbinol was absorbed slowly and oxidized to p-hydroxyphenyldiphenylcarbinol. Triphenylcarbinol and its p-hydroxy analog were found in urine, bile and feces, both free and conjugated with glucuronic acid. Traces of ortho- and meta-hydroxyphenyldiphenylcarbinol were detected both free and conjugated. There appeared to be three glucuronide fractions, possibly diglucuronides of hydroxytriphenylcarbinols, carbinol-group derived glucuronides and phenolic-group derived glucuronides.|Fish (S. mossambicus) were exposed to frescon for 22 hr. Analyses of fish indicated the presence of unchanged frescon and a small amount of morpholine. Similar results were observed when bile was analyzed.

... Tar impurities: 20 g/kg; volatile matter: 100 g/kg.

/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. /Organic bases/Amines 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 ventilations 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 ... . 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 patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines 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 as 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. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

Frescon

Trade Names: Frescon, WL 8008, Trifenmorph.|Emulsifiable concentrate.|Frescon Paste: active ingredient 50% N-tritylmorpholine.|FRESCON: (PRODUCT DISCONTINUED BY SHELL INTERNATIONAL CHEMICAL, LONDON)

World Health Organization has specified the chemical and physical requirements for technical trifenmorph WHO/SMT/5, 4-(triphenylmethyl)morpholine content: 900.0 g/kg; acidity: calculated as H2SO4 1 g/kg; water content: 1 g/kg; tar impurities: 20 g/kg; volatile matter: 100 g/kg.

Product analysis is by non-aqueous titration with a perchloric-acetic acid mixture ... or by HPLC. Residues may be determined colorimetrically with cyclohexane-sulfuric acid.|A colorimetric method has been developed for the determination of the molluscicide N-tritylmorpholine (Frescon, WL 8008) in water. The method is based on the production, from N-tritylmorpholine in strong acid, of the typical yellow colour of the tritylcarbonium ion. Two procedures are recommended for field use, neither of which distinguishes between N-tritylmorpholine and its hydrolysis product triphenylcarbinol (triphenylmethanol). A more precise laboratory procedure is described, by means of which both N-tritylmorpholine and triphenylcarbinol can be determined separately.|Analysis of products /is by/ extraction or dissolution in diethyl ether, clean-up by chromatography on a column of aluminum oxide using diethyl ether as eluent, evaporation of the solvent, & titration in chloroform & glacial acetic acid solution with perchloric acid (WHO Specifications for Pesticides, 226-229).

Agrochemicals -> Molluscicides