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Vamidothion

Vamidothion structure

Vamidothion 

structure
  • CAS No:

    2275-23-2

  • Formula:

    C8H18NO4PS2

  • Chemical Name:

    Vamidothion

  • Synonyms:

    Phosphorothioic acid,O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-oxoethyl]thio]ethyl] ester;Phosphorothioic acid,O,O-dimethyl ester,S-ester with 2-[(2-mercaptoethyl)thio]-N-methylpropionamide;RP 9895;O,O-Dimethyl S-[2-(1-methylcarbamoylethylthio)ethyl] phosphorothioate;Dimethyl S-[2-(1-methylcarbamoylethylthio)ethyl] phosphorothiolate;Kilval;Vamidoate;Vamidothion;Bamidothion;80966-70-7

  • Categories:

    Agrochemicals  >  Insecticides

Description

ChEBI: An organic thiophosphate that is N-methyl-2-[(2-sulfanylethyl)sulfanyl]propanamide in which the thiol group has been converted to the corresponding O,O-dimethyl thiophoshate. Formerly used as an inse ticide and acaricide, it is no longer approved for use within the European Union.


COLOURLESS CRYSTALS.


Vamidothion is an organic thiophosphate that is N-methyl-2-[(2-sulfanylethyl)sulfanyl]propanamide in which the thiol group has been converted into the corresponding O,O-dimethyl thiophoshate. Formerly used as an insecticide and acaricide, it is no longer approved for use within the European Union. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide, an agrochemical, an antibacterial agent and an antifungal agent. It is an organic thiophosphate and an organothiophosphate insecticide. It derives from a 2-((2-hydroxyethyl)sulfanyl)-N-methylpropionamide.

Vamidothion Basic Attributes

287.34

287.34

218-894-8

0758

2783

DTXSID7042510

Colorless needles|White crystalline

Characteristics

115

0.16 (est)

COLOURLESS CRYSTALS.

1.2±0.1 g/cm3

46-48 °C

2 °C

1.508

Solubility in water: very good

0-6°C

negligible at room temperature

Oral-rat LD50: 64 mg/kg; Oral-Mouse LD50: 40 mg/kg

Decompose toxic phosphorus oxide, sulfur oxide, nitrogen oxide gas by heating

Henry's Law constant = 8.60X10-16 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 5.77X10-11 cu cm/molec-sec at 25 °C (est)

Non-corrosive

Safety Information

III

6.1(b)

UN 2811

2

21-25-50-36-20/21/22-11

36/37-45-61-16

TF7900000

T;N,N,T,Xn,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Undergoes slight decomposition at room temperature, but solutions in organic solvents (methyl ethyl ketone, cyclohexanone) are stable. Decomposed in strong acidic or alkaline media.

P210-P280-P305 + P351 + P338

H225-H302 + H312 + H332-H319

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.

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P280, P301+P310, P302+P352, P312, P321, P322, P330, P363, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 41 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P312, P304+P340, P309+P311, P312, P314, P321, P322, P330, P363, P405, and P501

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. 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, liquid, NOS/|If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use foam, dry chemical. or carbon dioxide. /Organophosphorus pesticides, solid, NOS/

Environmental considerations: Land spill: Dig a pit, pong, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, solid, NOS/|Environmental considerations: Water spill: use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, solid, NOS/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, solid, NOS/|Environmental considerations: Land spill: Dig a pit, pong, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. /Organophosphorus pesticides, liquid, NOS/|For more Cleanup Methods (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/|Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, liquid, NOS/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, solid, NOS/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for VAMIDOTHION (16 total), please visit the HSDB record page.

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.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Do NOT wash away into sewer. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. Exposure at high levels could cause death. Cholinesterase inhibition. The effects may be delayed. Medical observation is indicated.

Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.

NO open flames.

PREVENT DISPERSION OF DUST! IN ALL CASES CONSULT A DOCTOR!

Use ventilation (not if powder), local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Toxicity

most toxic

ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/

LD50 Rat oral 64 mg/kg|LD50 Mice oral 40 mg/kg|LD50 Mice dermal 1500 mg/kg|LD50 Guinea pig oral 85 mg/kg|For more Non-Human Toxicity Values (Complete) data for VAMIDOTHION (10 total), please visit the HSDB record page.

Vamidothion's former production and use in the US as an acaricide and insecticide(1) may have resulted in its direct release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 810(SRC), determined from a structure estimation method(2), indicates that vamidothion is expected to have low mobility in soil(SRC). Volatilization of vamidothion from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.6X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Vamidothion is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-6 mm Hg(SRC), determined from a fragment constant method(4). Vamidothion is expected to biodegrade in the environment based on an observed half-life of 1-1.5 days in soil at 22 °C(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 810(SRC), determined from a structure estimation method(2), indicates that vamidothon 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 8.6X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.16(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Vamidothion is expected to biodegrade in the environment based on an observed half-life of 1-1.5 days in soil at 22 °C(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vamidothion, which has an estimated vapor pressure of 1.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Vapor-phase vamidothion 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 2.8 days(SRC), calculated from its rate constant of 5.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase vamidothion may be removed from the air by wet or dry deposition(SRC). Vamidothion, present at a concn of 100 mg/L in distilled water with 2-4% methanol, degraded only 2% after 6 hours during an aqueous photolysis test which used a suntest apparatus consisting of a xenon arc lamp emitting 300-800 nm of light(4), suggesting that vamidothion is not susceptible to direct photolysis(SRC).

The rate constant for the vapor-phase reaction of vamidothion with photochemically-produced hydroxyl radicals has been estimated as 5.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Vamidothion is expected to undergo aqueous hydrolysis under environmental conditions(2). A hydrolysis half-life of 36.5 days at 30 °C and at a pH of 4.5 was observed(2), which corresponds to a half-life of about 91 days at 20 °C(SRC), using a factor change of 2.5 based on the 10 deg temperature difference(3). The aqueous hydrolysis half-life of vamidothion in a pH 6.9 buffered ethanol-water solution (20:80) was determined to be 25.4 hours at 70 °C(4). Over the pH range of 3.0 to 7.0, the hydrolysis rate of phosphate esters is relatively constant although the rate generally increases at pH 7.0 and increases significantly (several fold to an order of magnitude) at pH 9.0(5). Based on these data, vamidothion is expected to undergo hydrolysis at least to some degree in most waters, and will do so much more quickly in warm, alkaline waters(SRC). Vamidothion, present at a concn of 100 mg/L in distilled water with 2-4% methanol, degraded only 2% after 6 hours during an aqueous photolysis test which used a suntest apparatus consisting of a xenon arc lamp emitting 300-800 nm of light(6). However, after 5% of acetone was added as a photosensitizer, the remainder of the vamidothion degraded 80, 70, 62, 56, 34, 17, and 5% after 30, 60, 90, 120, 180, 240, and 300 minutes, respectively(6). Based on these data, aqueous photolysis is not expected to be an important environmental fate process(SRC).

An estimated BCF of 3.2 was calculated for vamidothion(SRC), using an estimated log Kow of 0.16(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 vamidothion can be estimated to be 810(SRC). According to a classification scheme(2), this estimated Koc value suggests that vamidothion is expected to have low mobility in soil.

The Henry's Law constant for vamidothion is estimated as 8.6X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that vamidothion is expected to be essentially nonvolatile from water surfaces(2). Vamidothion is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-6 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: Vamidothion has been detected in surface water resources in The Netherlands(1).

A Danish study conducted by the Danish Pesticide Monitoring Program from 1995-1996 analyzed for, but did not detect, vamidothion in food commodities such as cereal, fruits, vegetables, bran, fish, and animal products(1).

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/

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

Drug Information

Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/|The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/|... The organophosphorus insecticides are, in contrast to the chlorinated insecticides, rapidly metabolized & excreted and are not appreciably stored in body tissues. /Organophosphorus insecticides/|Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/|For more Absorption, Distribution and Excretion (Complete) data for VAMIDOTHION (7 total), please visit the HSDB record page.

Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus cmpd/ to the corresponding phosphoric and phosphonic acids ... The cytochrome P450s are responsible for converting the inactive phosphorothioates containing a phosphorus sulfur (thiono) bond to phosphorates with a phosphorus-oxygen bond, resulting in their activation. These mixed-function oxidases also play a role in deactivation of certain organophosphorus agents. /Anticholinesterase agents/|These chemicals are detoxified by cytochrome p450-mediated monooxygenases in the liver, but some metabolites are more toxic than parent cmpd ... Metabolites usually are detected from 12 to 48 hr postexposure. /Organophosphate cmpd/|... Metabolized in plants to the corresponding sulfoxide which is of similar activity to vamidothion but of greater persistence.|In mammals and insects, demethylation and hydrolysis to phosphoric acid.|For more Metabolism/Metabolites (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation followed by depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/|The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 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. Administer activated charcoal ... . /Organophosphates 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. Monitor cardiac rhythm and treat arrhythmias if 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 and consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). USE UNDER DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam or lorazepam may be necessary ... . Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and related compounds/|Emergency and supportive measures. Caution: Rescuers and health-care providers must take measures to prevent direct contact with the skin or clothing of contaminated victims, because secondary contamination and serious illness may result, especially with potent pesticides or nerve agents. 1. Maintain an open airway and assist ventilation if necessary. Pay careful attention to respiratory muscle weakness because sudden respiratory arrest may occur. This is often preceded by increasing weakness of neck flexion muscles. In intubation is required, a nondepolarizing agent should be used because the effect of succinylcholine will be extended secondary to the inhibition of PChE. Administer supplemental oxygen. 2. Treat hydrocarbon pneumonitis, seizures, and coma if they occur. Seizures should be treated with benzodiazepines such as diazepam. 3. Observe asymptomatic patient for at least 8-12 hours to rule out delayed-onset symptoms, especially after extensive skin exposure of ingestion of a highly fat-soluble agent. /Organophosphorus and carbamate compounds/|Specific drugs and antidotes. Specific treatment includes the antimuscarinic agent atropine and the enzyme reactivator pralidoxime. 1. Give atropine... until signs of atropinization are present (decreased secretion and wheezing, increased hear rate). The most clinically important indication for continued atropine administration is persistent wheezing or bronchorrhea. Tachycardia is not a contraindication to more atropine. Note: Atropine will reverse muscarinic but not nicotinic effects. 2. Pralidoxime (2-PAM, Protopam) is a specific antidote that acts to regenerate the enzyme activity at all affected sites prior to aging. Other oximes include obidoxime and HI-6. Oximes may be less effective against dimethyl compounds compared with diethyl agents. a. Pralidoxime should be given immediately to reverse muscular weakness and fasciculations: ... . It is most effective if started early, before irreversible phosphorylation of the enzyme, but may still be effective if given later, particularly after exposure to highly lipid-soluble compounds. It is unclear how long oxime therapy should be continued, but it seems reasonable to continue it for 24 hr after the patient becomes asymptomatic. b. Pralidoxime generally is not recommended for carbamate intoxication, because in such cases the cholinesterase inhibition is spontaneously reversible and short-lived. However, if the exact agent is not identified and the patient has significant toxicity, pralidoxime should be given empirically. /Organophosphorus and carbamate compounds/|For more Antidote and Emergency Treatment (Complete) data for VAMIDOTHION (6 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ Eighteen people using vamidothion on crops were examined. The concentration of the product in air was 0.024 mg/cu m 50 meters away from the point of application. Symptoms recorded were a very slight drop in pulse rate and arterial blood pressure in 8 subjects. For 10 minutes, a reduction of 4-11% in blood cholinesterase was observed.|/SIGNS AND SYMPTOMS/ Organophosphate insecticides ... are potent cholinesterase enzyme inhibitors that act by interfering with the metabolism of acetylcholine, which results in accumulation of acetylcholine at neuroreceptor transmission sites. Exposure produces a broad spectrum of clinical effects indicative of massive overstimulation of the chlorinergic system, including muscarinic effects (parasympathetic), nicotinic effects (sympathetic and motor), and CNS effects. These effects present clinically as feeling of headache, weakness, dizziness, blurred vision, psychosis, respiratory difficulty, paralysis, convulsions, and coma. Typical findings are given by the mnemonic "SLUD." which stands for salivation, lacrimation, urination, and defecation. A small percentage of patients may fail to demonstrate miosis, a classic diagnostic hallmark. Onset of clinical manifestation of organophosphate poisoning usually occurs within 12 hours of exposure. /Organophosphate insecticides/|/SIGNS AND SYMPTOMS/ A follow up study of 232 people three years after a history of organophosphorus pesticide poisoning disclosed only one person with slight residual blurring of vision that might have been related to the earlier poisoning, though at the time of poisoning over one third of the people had blurring, which lasted only a day or two after exposure was discontinued. The possible exceptional case had findings suggestive of basilar artery insufficiency, rather than effects of poisoning. /Organophosphorus pesticide poisoning/|/SIGNS AND SYMPTOMS/ The duration of illness depends on the severity of poisoning, since several months may be required for cholinesterase activity to return to normal levels. Symptoms of mild to moderate organophosphate poisoning usually resolve by 1 month. A follow up study of pesticide workers who developed acute organophosphate poisoning revealed that episodes of headache, visual disturbances, nausea, and vomiting persisted 10 weeks after the acute episode, but the effect of reexposure to organophosphates could not be evaluated. /Organophosphate pesticide/|For more Human Toxicity Excerpts (Complete) data for VAMIDOTHION (11 total), please visit the HSDB record page.

Kilval

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Pupillary constriction, muscle cramp, excessive salivation. Sweating. Nausea. Dizziness. Laboured breathing. Convulsions. Unconsciousness.


MAY BE ABSORBED! See Inhalation.

Vamidothion Use and Manufacturing

Methods of Manufacturing

Vamidothion is produced by reaction of O,O-dimethylphosphoric acid chloride with the sodium salt of N-methylcarbamylethylmercaptoethanethiol.|... 2-Chloroethanol (ethylene chlorohydrin) is reacted with ethyl 2-mercapto propionate giving ethyl-2-(2-hydroxyethylthio)propionate. That intermediate is, in turn treated successively with methylamine and thionyl chloride to give 2-(2-chloroethylthio)-N-methylpropionamide. Condensation with O,O-dimethylphosphorothioate gives vamidothion.

Uses

Vamidothion is a phosphorothioic insecticide for apples and potatoes.

Emulsifiable solution.|Emulsifiable concentrate|Soluble concentrate (400 g ai/l)

The WHO Recommended Classification of Pesticides by Hazard identifies Vamidothion (technical grade) as Class IB: highly hazardous; Main Use: insecticide.|Not registered for use /in the United States/; Registered in many countries for cotton, hop, orchards, rice, sugarcane, vegetables, ornamentals; leafhoppers on rice.

Product analysis by hplc or glc ... Residues determined by glc

Agrochemicals -> Acaricides, Insecticides

Computed Properties

Molecular Weight:287.3
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:287.04148740
Monoisotopic Mass:287.04148740
Topological Polar Surface Area:115
Heavy Atom Count:16
Complexity:256
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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