Butonate

327.519

327.53

204-778-4

17872

DTXSID5041697

Colorless, somewhat oily liquid

2931900045

61.8

1.71 (est)

1.3742

129 °C @ Press: 0.5 Torr

277.2ºC

1.47

In water, 290 mg/L at 25 deg C (est)

Must be stored in its sealed original containers, in well-aired, fresh and dry storehouses or in shaded and possibly well-aired places.

1.1X10-4 mm Hg at 25 deg C (est)

Slight ester odor

Henry's Law constant = 3.0X10-10 atm-cu m/mol at 25 °C (est)

Low smell & staining properties /Technical/|Wt/gal 11.5 lb|Hydroxyl radical reaction rate constant = 7.5X10-12 cu cm/molec-sec at 25 °C (est)

Stable in neutral or acid aqueous solution; unstable in aqueous alkali.

P264, P270, P301+P312, P330, P501

H302

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

Toxicology Review: Residue Reviews 46: 1 (1973)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Wear self-contained breathing apparatus; wear full protective clothing. /Organophosphorus pesticides/

Do not extinguish fire unless flow can be stopped; use water in flooding quantities as fog; solid streams of water may be ineffective; cool all affected containers with flooding quantities of water; apply water from as far a distance as possible; use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides/

Avoid breathing vapors; keep upwind; avoid bodily contact with the material; wash away any material which may have contacted the body with copious amounts of water, or soap and water. /Organophosphorus pesticides/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

LD50 Rat oral 1000 mg/kg|LD50 Rat dermal 7000 mg/kg|LD50 Rat ip 700 mg/kg|LD50 Rat sc 3000 mg/kg|For more Non-Human Toxicity Values (Complete) data for BUTONATE (14 total), please visit the HSDB record page.

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

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a structure estimation method(2), indicates that butonate is expected to have low mobility in soil(SRC). Volatilization of butonate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Butonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-4 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a structure estimation method(2), indicates that butonate 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 3.0X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4.1(SRC), from an estimated log Kow of 1.7(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). When butonate (1.5 kg/ha) was applied to a forest as the preparation Fekama A25, the butonate concentration in a creek in that forest was 1000 ug/L immediately after application, 0.1 ug/L after 6 hours, and 0.02 to 0.05 ug/L after 72 hours(8). At 150 to 250 hours post butonate application, the butonate degradation products trichlorfon and dichlorvos were present in the water at 2 to 3 and 0.06 to 0.08 ug/L, respectively(8). Eutrophic carp ponds containing plankton were treated with 400-1000 ug butonate. The half-life range of butonate in the pond water was found to be 46.5 to 108.7 hours(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butonate, which has an estimated vapor pressure of 1.1X10-4 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 butonate 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 4.3 days(SRC), calculated from its rate constant of 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butonate may be removed from the air by wet or dry deposition(SRC). Butonate is susceptible to direct photolysis by sunlight and the photolysis products of an aqueous solution of butonate exposed to UV light were found to be vinyl butonate, chlorophos, DDVP, and HCl(4).

The rate constant for the vapor-phase reaction of butonate with photochemically-produced hydroxyl radicals has been estimated as 7.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 4.7X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 4.7 years, 170 days, and 17 days at pH values of 7, 8, and 9, respectively(2). In a aqueous environment hydrolysis study, butonate was found to hydrolyze to the hydroxy deriviative chlorophos in acid media (pH 1.9 to 5) and dehydrochlorination occurred in alkaline media (pH 7.4 to 9.4) to produce vinyl butonate(3). Butonate is susceptible to direct photolysis by sunlight and the photolysis products of an aqueous solution of butonate exposed to UV light were found to be vinyl butonate, chlorophos, DDVP, and HCl(4).

An estimated BCF of 4.1 was calculated for butonate(SRC), using an estimated log Kow of 1.7(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of butonate can be estimated to be 1,100(SRC). According to a classification scheme(2), this estimated Koc value suggests that butonate is expected to have low mobility in soil.

The Henry's Law constant for butonate is estimated as 3.0X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that butonate is expected to be essentially nonvolatile from water surfaces(2). Butonate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Butonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Spraying 45 mg butonate/cow after morning milking gave residues of 0.03-0.1 mg/kg in milk from evening milking and equal residues of butonate metabolite, trichlorfon.

Occupational exposure and general population exposure should be low or non-existent since butonate is no longer produced or used in the United States. In the past, butonate was applied directly to the environment as an insecticide and exposure to this compound was primarily in the workplace where butonate was produced or used. (SRC)|... Toxic by inhalation, skin absorption, and/or ingestion. /Organophosphorus pesticide/

MEDICATION: Anthelmintic (schistosoma)|MEDICATION (VET): Formerly Anthelminic for horses|MEDICATION (VET): Orally, for horses other than sucklings and young weanlings for removal of bots (Gastrophilus intestinalis, G. nasalis) and ascarids (Parascaris equorum). ... /Butonate/ and its metabolites in milk are rapidly broken down by pasteurization into non-toxic substances. ... Shows promise as a pour-on insecticide for lactating cows.|MEDICATION (VET): Anthelmintic (nematodes); ectoparasiticide

VET: Do not use in conjunction with or within few days of (before and after) any other cholinesterase inhibiting compound ... /or/ phenothiazine/s/ ...Do not administer to sick, debilitated, or colicky horses or those whose meat is ...for ...food.

... The MAC is 2 mg/cu m. The half-life of butonate in fruits and vegetables is 0.5-1.5 days. The necessary waiting period after treatment is 3-7 days for general-purpose crops, and 10 days for crops to be used in baby food and dietetic preparations.

In plants, butonate was metabolized by deacylation via trichlorphon and demethyltrichlorphon with dichlorvos as minor metabolite and by demethylation via demethylbutonate.|In the liver and blood of warm blooded animals, butonate was degraded primarily by hydrolysis of P-C bond with formation of dimethylphosphate. Small amount of the desmethylbutonate also formed in blood in vitro. Butonate was also hydrolyzed by fish. In insects, the organic acid was removed by esterase action and trichlorofon (Dipterex) was formed, which in turn was metabolized to DDVP.|In aq nonbiological media, butonate was degraded at pH less than 5.5 to trichlorphon, demethyltrichlorphon, and demethylbutonate, at pH greater than 5.5 preferably to vinylbutonate, demethylbutonate, and demethylvinylbutonate with traces of trichlorphon.|The effects of Phosphorus containing insecticides and their metabolites on blood cholinesterase activity were measured by determining the change in pH during hydrolysis of acetylcholine. Naled, dichlorvos, and trichlorfon were stronger inhibitors than butonate.|For more Metabolism/Metabolites (Complete) data for BUTONATE (6 total), please visit the HSDB record page.

The half-life of butonate in fruits and vegetables is 0.5-1.5 days.|It's half-life in blood stream of cattle is only about 3-4 min.|T/2 on apples and plums was 1.5 days; on cherries, 0.5 days.|/LABORATORY ANIMALS: Acute Exposure/ Male mice were given ... 10 mg/kg butonate intraperitoneally. Tthe half life in liver was about 2 hours. ...

Parathion and its relatives are known to inhibit enzyme cholinesterase in all parts of the body by phosphorylating the active site. Toxic signs and symptoms are regarded as indirect consequences of this enzyme inactivation. /Parathion/

Basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway control may be needed. 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 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. Administer activated charcoal ... . /Organophosphates and Related Compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). ... . Treat seizures with adequate atropinization and correction of hypoxia. Rarely is diazepam necessary ... . For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and Related compounds/|Airway protection. Insure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/|Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. ... Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. ... The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for BUTONATE (17 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ 1. Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis ... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain ... Mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. ... 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction, or all three. /Parathion/.|/OTHER TOXICITY INFORMATION/ Its relatively low mammalian toxicity is attributed to rapid hydrolysis of the butyl and phosphate ester groupings.

butonate

T 113|TRIBUFON|ENT-20852|PEDIX-BUTONATE|For more Formulations/Preparations (Complete) data for BUTONATE (7 total), please visit the HSDB record page.

...It is compatible with non-alkaline pesticides.|Gels for control of equine endoparasites contain butonate, a thickening agent, acid scavenger, and others.|Anthelmintic for horses (Vet) /SRP66: Former use/

PRODUCT ANALYSIS BY POLAROGRAPHY (PA GIANG & RL CASWELL, J AGRIC FOOD CHEM 157, 5, 753), OR BY POTENTIOMETRIC TITRATION OF THE CHLORIDE ION RESULTING FROM HYDROLYSIS WITH ETHANOLIC ETHANOLAMINE (CIPAC HANDBOOK, 1970, 1, 684)... /TRICHLORFON/|TRICHLORFON DETERMINATION IN ALFALFA BY GC/THERMIONIC FLAME IONIZATION DETECTION; LIMIT OF DETECTION: 0.02 MG/KG /ZWEIG G, SHERMA J; IN: ANALYTICAL METHODS FOR PESTICIDES AND PLANT GROWTH REGULATORS, ZWEIG G ED, VOL VI, NEW YORK ACADEMIC PRESS, 387-392 (1972)/ IN VEGETABLES BY GC/MICROCOULOMETRIC DETECTION; LIMIT OF DETECTION; 0.1 MG/KG, IN MILK BY GC/ELECTRON CAPTURE DETECTION 0.01 MG/KG, IN ANIMAL TISSUE BY GC/ELECTRON CAPTURE DETECTION; LIMIT OF DETECTION 0.1 MG/KG /MARKUS JR, PUMA B; ED, PESTICIDE ANALYTICAL MANUAL: METHODS FOR INDIVIDUAL PESTICIDE RESIDUES, VOL 2, WASHINGTON DC, USFDA, PESTICIDE REG SEC 120,198 (1970)/. /TRICHLORFON/|Butonate with its metabolites trichlorfon, vinylbuonate and DDVP were extracted from rice grain with Me2CO and from soil with Me2CO-0.05 N CaCl2 (1:1), reextracted with CHCl3, which also was used for extraction from water, and introduced in Me2CO into a gas chromatograph. Trichlorfon was determined by gas adsorption chromatography on polysorb-1, and other components by gas chromatography on chromaton N-AW, using the N carrier gas and a constant recombination rate detector. In both cases the column temp was 180 degrees. TLC on Silufol, using the Me2CO-H2O solvent system gave satisfactory separation. Detection threshold was 0.5 mug for trichlorfon and 0.1-0.2 mug for other components, when AgNO3 was used for visualization in UV.