PROPETAMPHOS Chemical Properties

Melting point:

<25℃

Boiling point:

bp0.005 87-89°

Density 

1.1294 g/cm³ (20 ºC)

vapor pressure 

1.9×10^-3Pa (20°C)

refractive index 

nD20 1.495

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

Water Solubility 

110 mg l^-1(24°C)

pka

0.94±0.70(Predicted)

Merck 

13,7907

BRN 

1979853

Stability:

Light Sensitive, Moisture Sensitive

EPA Substance Registry System

Propetamphos (31218-83-4)

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-50/53

Safety Statements 

37-45-60-61

RIDADR 

3018

WGK Germany 

3

RTECS 

GQ4750000

HazardClass 

6.1(b)

PackingGroup 

II

HS Code 

29299090

Hazardous Substances Data

31218-83-4(Hazardous Substances Data)

Toxicity

LD50 orally in male rats: 82 mg/kg (Berg, Gothe)

PROPETAMPHOS Usage And Synthesis

Description

Propetamphos technical is a yellowish, oily liquid at room temperature and a moderately toxic acaricide and insecticide. It is sparingly soluble in water, but very soluble in acetone, chloroform, ethanol, and hexane. U.S. EPA has classified propetamphos both as a GUP and RUP, indicating that its handling should be done by certified, qualified, and applicators. Propetamphos is used to control cockroaches, flies, ants, ticks, moths, fleas, and mosquitoes in households and where vector eradication is necessary to protect public health. It is also used in veterinary applications to combat parasites such as ticks, lice, and mites in livestock. The formulations of propetamphos include aerosols, emulsified concentrates, liquids, and powders. In veterinary applications, the insecticide is used for the control of ticks, lice, and mites in livestock. Commercial products include aerosols, emulsified concentrates, liquids, and powders.

Chemical Properties

Propetamphos technical is a yellowish, oily liquid at room temperature and a moderately toxic acaricide and insecticide. It is sparingly soluble in water, but very soluble in acetone, chloroform, ethanol, and hexane. The US EPA has classifi ed propetamphos as a GUP and RUP, indicating that its handling should be done by certifi ed, qualifi ed applicators. Propetamphos is used for the control of cockroaches, fl ies, ants, ticks, moths, fl eas, and mosquitoes in households and where vector eradication is necessary to protect public health. It is also used in veterinary applications to combat parasites, such as ticks, lice, and mites in livestock. The formulations of propetamphos include aerosols, emulsifi ed concentrates, liquids, and powders. Commercial products include aerosols, emulsifi ed concentrates, liquids, and powders.

Uses

Insecticide.

Uses

Propetamphos is used to control household and public health pests, especially cockroaches, clothes moths and ants. It is also used for the control of ectoparasites (mites, lice and ticks).

Uses

Propetamphos may be used as an analytical reference standard for the determination of the analyte in human tissues, fruits and crops by various chromatography techniques.

Definition

ChEBI: Propetamphos is a phosphoramidate ester, an organophosphate insecticide and an isopropyl ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an agrochemical. It is functionally related to an isopropyl 3-hydroxybut-2-enoate.

General Description

Yellow oily liquid. Non corrosive. Used as an insecticide.

Air & Water Reactions

Water soluble.

Reactivity Profile

An organophosphate derivative. Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Health Hazard

Propetamphos is a moderately toxic organophosphate insecticide. It inhibits the cholinesterase enzyme in animals and humans leading to overstimulation of the CNS. Prolonged period of exposures to high concentrations of propetamphos cause poisoning with symptoms that include, but are not limited to, nausea, headache, dizziness, confusion, numbness, tingling sensations, incoordination, tremor, abdominal cramps, sweating, blurred vision, breathing diffi culty, unconsciousness, and convulsions, slow heart beat, respiratory paralysis, and death. There is no evidence to suggest that propetamphos causes mutagenic, teratogenic, or carcinogenic effects in animals or humans.

Agricultural Uses

Fungicide, Insecticide: Propetamphos is used indoors for the control of structural insects, e. g., ants, cockroaches, fleas, and termites. It is applied in indoor residential, medical, commercial, and industrial buildings, and in food service

Trade name

BLOTIC®; OVIDIP®; SAFROTIN®[C]; SAN-52139®; SANDOZ®52139; SERAPHOS®; TSAR®; VEL-4283®; ZOECON®

Safety Profile

Poison by ingestion. Moderately toxic by skin contact. When heated to decomposition it emits very toxic fumes of POx, SOx, and NOx.

Carcinogenicity

There was no significant treatment- related increase in the incidence of any tumor type of cancer among male rats given diets with 0, 6, 12, and 120 ppm (0, 0.376, 0.632, and 5.891 mg/kg/day (males) and, 0, 0.412, 0.689, and 7.602 mg/kg/day (females), respectively) for 24 months . In females, there was an increase in pancreatic islet cell adenomas at all dose levels compared to controls. A significant decrease in body weight was observed in both sexes at the high dose.
When propetamphos was administered to mice via the diet at dose levels of 0, 0.5, 1.0, 6.0, and 21 mg/kg/day for 91 weeks, there was no apparent increase in the incidence of tumors in either sex at dose levels that caused significant cholinesterase inhibition . There was no adverse effect on survival of males, but high-dose females had a higher mortality rate than control females and a shorter survival time. There were no adverse effects on body weight or bodyweight gain in either sex.

Metabolic pathway

The major pathways of propetamphos detoxification in insect tissue and in the mouse differ, with the principal route in insects being glutathione conjugation but O-demethylation in the mouse. Oxidative or hydrolytic cleavage of the P-O-crotonyl linkage to yield isopropyl acetoacetate, which is hydrolysed and further metabolised to CO₂, is also an important route. As with mevinphos, which also contains a crotonyl ester group, de-esterification is not an important detoxification route in animals and no propetamphos carboxylic acid has been detected in the animal experiments which have been reported.

Metabolism

Propetamphos administered in animals is rapidly metabolized and excreted mainly via urine and exhaled air. The major pathways of detoxication in mammals are O-demethylation and cleavage of the P?O-vinyl linkage to give isopropyl acetoacetate, which is finally metabolized to carbon dioxide. Hydrolysis of the carboxylic ester bond is also involved. Activation by oxidative desulfuration also occurs.

Toxicity evaluation

The acute oral LD₅₀ for rats is 59.5–119 mg/kg. Inhalation LC50 (4 h) for rats is 0.69 (female) and >1.5 (male) mg/L air. NOEL (2 yr) for rats is 6 mg/kg diet (0.3 mg/kg/d).

Degradation

The hydrolytic DT₅₀, values at pH 3, 6 and 9 were 11 days, 1 year and 41 days respectively. Propetamphos is stable to light and no degradation was detected after 70 hours of exposure to sunlight (PM).

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