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Tebupirimfos

Tebupirimfos structure

Tebupirimfos 

structure
  • CAS No:

    96182-53-5

  • Formula:

    C13H23N2O3PS

  • Chemical Name:

    Tebupirimfos

  • Synonyms:

    Phosphorothioic acid,O-[2-(1,1-dimethylethyl)-5-pyrimidinyl] O-ethyl O-(1-methylethyl) ester;MAT 7484;BAY-MAT 7484;Tebupirimphos;Tebupirimfos;Phostebupirim

  • Categories:

    Agrochemicals  >  Insecticides

Description

Phostebupirim is an amber-to-brown liquid. Phostebuprim hydrolyzes under alkaline conditions.Soluble in water at 5.5 mg/mL; completely miscible with all solvents tested at 20°C.


AMBER OR BROWN LIQUID.


Tebupirimfos is an organic thiophosphate and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It derives from a 2-tert-butylpyrimidin-5-ol.

Tebupirimfos Basic Attributes

318.37

318.37

1767

3018

DTXSID1032482

Amber to brown liquid

2933599012

Characteristics

85.6

4.2

0.59-0.67 g/cm³

152 °C

171℃

1.514

Solubility in water at 20°C: very poor

2-8°C

Vapour pressure, Pa at 20°C: 0.04 (negligible)

Safety Information

I

6

UN28106.1/PG1

3

26/27/28-50/53

28-36/37-45-60-61

TF8750000

T+,N

Separated from food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

Hydrolysed under alkaline conditions.

P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501

H300

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.

USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Phostebupirim. EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of July 24, 2003: http://www.epa.gov/pesticides/reregistration/status.htm]

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.) /Organophosphorus pesticides, solid, toxic/|If material on fire or involved in fire: 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, dry chemical or carbon dioxide. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic/

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, 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, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/

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, toxic/|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, toxic/|Personnel protection: Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. /Organophosphorus pesticides, liquid, flammable, toxic/|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, toxic|For more Preventive Measures (Complete) data for TEBUPIRIMFOS (8 total), please visit the HSDB record page.

/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 TEBUPIRIMFOS (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: complete protective clothing and face shield. Do NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Store and dispose of according to local regulations.

Separated from food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

Cholinesterase inhibition. The substance may cause effects on nervous system.

Cholinesterase inhibition. This may result in nervous system impairment.

NO open flames.

PREVENT GENERATION OF MISTS! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust.

Protective gloves. Protective clothing.

Wear face shield in combination with breathing protection.

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

Toxicity

LD50 Rat (male) oral 2.9-3.6 mg/kg|LD50 Rat (female) oral 1.3-1.8 mg/kg|LD50 Mouse (male) oral 14.0 mg/kg|LD50 Mouse (female) oral 9.3 mg/kg|For more Non-Human Toxicity Values (Complete) data for TEBUPIRIMFOS (8 total), please visit the HSDB record page.

Tebupirimfos's production may result in its release to the environment through various waste streams(SRC); it's use as an insecticide(1) may result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1845(SRC), determined from a structure estimation method(2), indicates that tebupirimfos is expected to have low mobility in soil(SRC). Volatilization of tebupirimfos from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-6 atm-cu m/mole derived from its vapor pressure, 3.75X10-5 mm Hg(4), and water solubility, 5.5 mg/l(4). Tebupirimfos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). The half-lives of tebupirimfos in aerobic and anaerobic soil metabolism studies were reported as 343 and 279 days, respectively(5). The degradation products observed were desisopropyltebupirimfos, desethyltebupirimfos, t-butylhydroxypyrimidine, and the S-ethyl isomer of isopropyltebupirimfos(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1845(SRC), determined from a structure estimation method(2), indicates that tebupirimfos is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.8X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 3.75X10-5 mm Hg(4), and water solubility, 5.5 mg/l(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 and 174 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 334(SRC), from an estimated log Kow of 4.19(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The half-life of tebupirimfos was calculated as 194 days in a pond water/soil mesocosm maintained under anaerobic conditions(8). The aqueous photolysis half-life of tebupirimfos was reported as 31 hours(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tebupirimfos, which has an estimated vapor pressure of 3.75X10-5 mm Hg at 20 °C (2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tebupirimfos 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 hours(SRC), calculated from its rate constant of 1.13X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Tebupirimfos was reported to have an aqueous photolysis half-life of 31 hours(4), suggesting direct photolysis may occur in the atmosphere.

The rate constant for the vapor-phase reaction of tebupirimfos with photochemically-produced hydroxyl radicals has been estimated as 1.13X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Tebupirimfos is hydrolyzed under alkaline conditions(2), but the rate of hydrolysis is not known. The aqueous photolysis half-life of tebupirimfos was reported as 31 hours(3).

An estimated BCF of 334 was calculated for tebupirimfos(SRC), using an estimated log Kow of 4.19(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tebupirimfos can be estimated to be 1845(SRC). According to a classification scheme(2), this estimated Koc value suggests that tebupirimfos is expected to have low mobility in soil(SRC).

The Henry's Law constant for tebupirimfos is estimated as 2.8X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 3.75X10-5 mm Hg(1), and water solubility, 5 mg/l(1). This Henry's Law constant indicates that tebupirimfos is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 15 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 174 days(SRC). Tebupirimfos's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Tebupirimfos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

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

Secondary exposure of children through contact with their parents' contaminated clothing can also occur. /Organophosphorus pesticides/

Drug Information

A rat metabolism study demonstrated that the insecticide was readily absorbed, distributed, metabolized, and excreted and that bioaccumulation and retention of the compound and/or its metabolites are low in rats. In vivo and in vitro metabolism studies indicate that the insecticide is metabolized by mixed function oxidases to O-[2-(1,1-dimethylethyl)-5-pyrimidinyl] O-ethyl-O-(1-methylethyl) phosphorothioate (OMAT), an oxygen analog, which is rapidly hydrolyzed to 2-(1,1-dimethylethyl)-5-hydroxypyrimidine (TPHP) and excreted as the glucuronide conjugate of TBHP, a major metabolite representing 60-74% of the administered radioactivity.|Metabolism occurs principally by oxidation, hydrolysis by esterases, and by transfer of portions of the molecule to glutathione. Oxidation of organophosphorus insecticides may result in more or less toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products, that are, in most cases, of low toxicity. Hydrolytic and transferase reactions affect both the thioates and their oxons. /Organophosphorus Pesticides/

Organophosphorus insecticides exert their acute effects in both insects and mammals by inhibiting acetylcholinesterase (AChE) in the nervous system with subsequent accumulation of toxic levels of acetylcholine (ACh), which is a neurotransmitter. In many cases, the organophosphorylated enzyme is fairly stable, so that recovery from intoxication may be slow. /Organophosphorus Pesticides/

Fresh air, rest. Refer immediately for medical attention.


Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.


Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Airway protection. Ensure 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. Depending on the severity of poisoning, doses of atropine ranging from very low to...high... . The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. 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. Favorable response to a test dose of atropine can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe poisonings. The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. ...Do not administer atropine or pralidoxime prophylactically to workers exposed to organophosphate pesticides. Prophylactic dosage with either atropine or pralidoxime may mask early signs and symptoms of organophosphate poisoning and thus allow the worker to continue exposure and possibly progress to more severe poisoning. Atropine itself may enhance the health hazards of the agricultural work setting: impaired heat loss due to reduced sweating and impaired ability to operate mechanical equipment due to blurred vision. This can be caused by mydriasis, one of the effects of atropine. /Organophosphate pesticides/|Glycopyrolate has been studied as an alternative to atropine and found to have similar outcomes using continuous infusion. Ampules of... glycopyrolate were added to... saline and this infusion was titrated to the desired effects of dry mucous membranes and heart rate above 60 beats/min. During this study, atropine was used as a bolus for a heart rate less than 60 beats/min. The other apparent advantage to this regimen was a decreased number of respiratory infections. This may represent an alternative when there is a concern for respiratory infection due to excessive and difficult to control secretions, and in the presence of altered level of consciousness where the distinction between atropine toxicity or relapse of organophosphate poisoning is unclear. /Organophosphate pesticides/|Pralidoxime. Before administration of pralidoxime, draw a blood sample (heparinized) for cholinesterase analysis (since pralidoxime tends to reverse the cholinesterase depression). Administration pralidoxime (Protopam, 2-PAM), a cholinesterase reactivator, in cases of severe poisoning by organophosphate pesticides in which respiratory depression, muscle weakness, and/or twitching are severe. When administered early (usually less than 48 hours after poisoning) pralidoxime relieves the nicotinic as well as the muscarinic effects of poisoning. Pralidoxime works by reactivating the cholinesterase and also by slowing the "aging" process of phosphorylated cholinesterase to a non-reactivatable form. ... Dosage of pralidoxime may be repeated in 1-2 hours, then at 10-12 hour intervals if needed. In very severe poisonings, dosage rates may be doubled. Repeated doses of pralidoxime are usually required. In cases that involve continuing absorption of organophosphate (as after ingestion of large amounts), or continuing transfer of highly lipophilic organophosphate from fat into blood, it may be necessary to continue administration of pralidoxime for several days beyond the 48 hour post-exposure interval usually cited as the limit of its effectiveness. ... Blood pressure should be monitored during administration because of the occasional occurrence of hypertensive crisis. Administration should be slowed or stopped if blood pressure rises to hazardous levels. Be prepared to assist pulmonary ventilation mechanically if respiration is depressed during or after pralidoxime administration. If intravenous injection is not possible, pralidoxime may be given by deep intramuscular injection. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for TEBUPIRIMFOS (17 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Signs and symptoms of acute intoxication by organophosphorus insecticides include muscarinic, nicotinic, and central nervous system (CNS) manifestations. Symptoms may develop rapidly, or there may be a delay of several hours after exposure before they become evident. The delay tends to be longer in the case of more lipophilic compounds, which also require metabolic activation. Symptoms may increase in severity for more than one day and may last for several days. In severe cases, respiratory failure is a dominant effect. /Organophosphorus Pesticides/|/SIGNS AND SYMPTOMS/ Phostebupirim can cause cholinesterase inhibition in humans; that is, it can overstimulate the nervous system causing nausea, dizziness, confusion, and at very high exposures (e.g., accidents, major spills), respiratory paralysis and death.|/SIGNS AND SYMPTOMS/ Principal effects /of anticholinesterases as toxic components of insecticides/ on eye, whether from local contact or systemic poisoning, are miosis and spasm of accommodation for near vision. /Anticholinesterases/

phostebupirim

The substance can be absorbed into the body in hazardous amounts by ingestion, through the skin and by inhalation.

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


MAY BE ABSORBED! See Inhalation.

Tebupirimfos Use and Manufacturing

Uses

Tebupirimfos is an organophosphorous insecticide developped for soil application.

Mixtures: 'Aztec' (+ cyfluthrin) (Amvac, Bayer)|Granules|Aztec 2.1% Granular Insecticide, Aztec 4.67% Granular Insecticide

The WHO Recommended Classification of Pesticides by Hazard identifies Tebupirimfos (technical grade) as Class IA: extremely hazardous; Main Use: insecticide.

Computed Properties

Molecular Weight:318.37
XLogP3:4.2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:318.11670077
Monoisotopic Mass:318.11670077
Topological Polar Surface Area:85.6
Heavy Atom Count:20
Complexity:339
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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