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| | Methidathion Basic information |
| | Methidathion Chemical Properties |
| Melting point | 39-40°C | | Boiling point | 347.7±52.0 °C(Predicted) | | density | 1.51 g/cm3 | | vapor pressure | 2.5×10-4 Pa (20 °C) | | Fp | 100 °C | | storage temp. | 0-6°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | -4.17±0.40(Predicted) | | form | solid | | color | Colourless | | Water Solubility | 0.024 g/100 mL | | BRN | 619915 | | Stability: | Air Sensitive, Moisture Sensitive | | CAS DataBase Reference | 950-37-8(CAS DataBase Reference) | | NIST Chemistry Reference | Methidathion(950-37-8) | | EPA Substance Registry System | Methidathion (950-37-8) |
| | Methidathion Usage And Synthesis |
| Description | Methidation is used as an insecticide. Cross-sensitivity
was described to dichlorvos. | | Description | Methidathion is an organophosphate insecticide that inhibits insect cholinesterase. It reduces cattle lice (L. vituli, D. bovis, and H. eurysternus) infestation by 99.1% when administered topically at a dose of 3.5 mg/kg. Methidathion is selectively toxic to lice over cattle, only inhibiting cattle plasma acetylcholinesterase activity by 20% with no effect on survival when administered topically at a dose of 24 mg/kg. It increases sister chromatid exchange (SCE) in a concentration-dependent manner and induces cell cycle arrest at the M1 phase in V79 cells when used at a concentration of 40 μg/ml. Dietary administration of methidathion (1.4-4.7 mg/kg) increases alanine aminotransferase, aspartate aminotransferase, sorbitol dehydrogenase, and alkaline phosphatase activity, inhibits cholinesterase, and induces chronic liver inflammation in male beagle dogs. It also induces loss of striation and myocytolysis of cardiomyocytes and reduces serum cholinesterase activity in rats when administered orally at a dose of 5 mg/kg. | | Chemical Properties | Methidathion is a colorless crystalline solid. | | Chemical Properties | Crystalline solid. Almost insoluble in
water; soluble in common organic solvents. | | Chemical Properties | Methidathion is a colorless crystalline pesticide at room temperature. It is sparingly soluble in water, but very soluble in octanol, ethanol, xylene, acetone, and cyclohexane. Methidathion is a non-systemic organophosphorous insecticide and acaricide with stomach and contact action. It is used to control a variety of insects and mites on crops and fruit plants. Methidathion is highly toxic to animals and humans. The US EPA grouped methidathion as a class I toxic substance and as an RUP. | | Uses | Methidathion is used to control a wide range of insects in many
different crops. | | Uses | Insecticide and acaricide. | | Uses | Insecticide, acaricide. | | Uses | Methidathion is an organophosphate insecticide and was examined for human health and toxicological concerns. | | Definition | ChEBI: Methidathion is an organic thiophosphate and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is functionally related to a 5-methoxy-1,3,4-thiadiazol-2(3H)-one. | | General Description | Methidathion is a colourless crystalline pesticide at room temperature. It is sparingly soluble in water but very soluble in octanol, ethanol, xylene, acetone, and cyclohexane.
| | Air & Water Reactions | Stable in neutral or weak acid solution. Hydrolyzed by alkali. [EPA, 1998]. | | Reactivity Profile | Organophosphates, such as Methidathion, 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. | | Hazard | Toxic by ingestion, a cholinesterase
inhibitor. | | Health Hazard | Methidathion is poisonous to humans. Its toxic effects are by action on the nervous system. Human volunteers ingesting 0.11 mg/kg/day for 6 weeks had no clinical effects. | | Health Hazard | Acute and prolonged exposures to methidathion cause poisoning in animals and humans. The symptoms include, but are not limited to, nausea, vomiting, cramps, diarrhea, salivation, headache, dizziness, muscle twitching, diffi culty breathing, blurred vision, and tightness in the chest, pulmonary edema, respiratory depression, and respiratory paralysis. Acute exposures to high concentrations of methidathion cause intense breathing problems, including paralysis of the respiratory muscles. | | Fire Hazard | (Non-Specific -- Organophosphorus Pesticide, n.o.s.) Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Stable in neutral or weak acid solution. Hydrolyzed by alkali. | | Agricultural Uses | Insecticide: A U.S. EPA restricted Use Pesticide (RUP). Not approved for use in EU countries
. There are no residential
uses for methidathion. Methidathion is a non-systemic organophosphate insecticide and acaricide with stomach and
contact action. The compound is used to control a variety
of insects and mites in many crops such as nuts, artichokes,
olives, cotton, fruits, vegetables, tobacco, alfalfa, and sunflowers, and also in greenhouses and on rose cultures. It is
especially useful against scale insects. | | Trade name | CIBA-GEIGY® GS 13005®;
COBRACIDE®; FISONS NC® 2964; GEIGY® 13005; GS-13005®; SOMONIC®; SOMONIL®; SURPRACIDE®;
SUPRATHION®; ULTRACID®; ULTRACIDE® | | Contact allergens | Methidation is an organophosphorus compound used as an insecticide. Cross-sensitivity was described to Dichlorvos. | | Safety Profile | Poison by ingestion and
skin contact. Moderately toxic by inhalation.
Human mutation data reported. Human
systemic effects: coma, lachrymation, miosis.
A severe eye irritant. An insecticide. When
heated to decomposition it emits very toxic
fumes of NOx, POx, and SOx | | Carcinogenicity | In a chronic toxicity/carcinogenicity study, rats were fed
diets with 0, 4, 40, or 100 ppm methidathion (equivalent to 0,
0.16, 1.72, or 4.91 mg/kg/day (males) and 0, 0.22, 2.20, or
6.93 mg/kg/day (females)) for 2 years, and there was no
evidence of carcinogenicity in either males or females .
Body weight decreases occurred in both sexes at the highest
dose throughout the study. | | Environmental Fate | Photolytic. When methidathion in an aqueous buffer solution (25°C and pH 7.0) was
exposed to filtered UV light (l >290 nm) for 24 hours, 17% decomposed to 5-methoxy-
3H-1,3,4-thiadiazol-2-one. At 50°C, 56% was degraded after 24 hours. Degradation
occurred via hydrolysis of the thiol bond of the phosphorodithioic ester. Under acidic and
alkaline conditions, hydrolytic cleavage occurred at the C-S and P-S bonds, respectively
(Burkhard and Guth, 1979). Smith et al. (1978) demonstrated that methidathion degraded
to methidathion oxon at a faster rate in six air-dried soils than in moist soils. Half-lives
for methidathion in the air-dried soils ranged from 19 to 110 days. In addition, methidathion
degraded faster in an air-dried soil exposed to ozone (half-lives 2.5 to 7.0 days).
Chemical/Physical. Emits toxic fumes of phosphorus, nitrogen and sulfur oxides when
heated to decomposition (Sax and Lewis, 1987). Methidathion oxon was also found in
fogwater collected near Parlier, CA (Glotfelty et al., 1990). It was suggested | | Metabolic pathway | The main route of methidathion metabolism in animals and plants is via
hydrolysis or oxidation (or hydrolysis of the oxon) to yield the 3-
thiomethyl-5-methoxy-1,3,4-thiadiazoldee rivative. This may either lose
methanethiol to yield the methoxy-1,3,4thiadiazolinone or be conjugated
as the cysteine derivative via a route involving desmethylmethidathion
(in plants). In plants and mammals an additional route involves the
methylation of the thiomethyl methoxy-1,3,4-thiadiazolinone derivative
by S-adenosylmethionine followed by oxidation to the corresponding
sulfoxide and sulfone which are excreted in the urine in mammals.
Another route of detoxification in insects, plants and mammals is via
demethylation of the 5-methoxy group of the 1,3,4-thiadiazolinone ring
to form a metabolite which may be conjugated in plants. As is common
with many phosphorothioates, the active acetylcholinesterase inhibitor,
methidaoxon, is usually detected in metabolism studies but at very low
concentration due to its rapid rate of hydrolysis. | | Metabolism | The principal degradation route is similar
both in animals and plants, that is, cleavage of the P?S
bond via oxidative desulfuration (activation) to the oxon
followed by hydrolysis to O,O-dimethyl hydrogen phosphorothioate
and the 3-thiomethyl-5-methoxythiadiazole
derivative, which is further degraded or conjugated.
Methidathion is rapidly degraded in soil; DT50 in soil
is 3–18 d. | | Shipping | Color code—Blue: Health Hazard/Poison: Store in
a secure poison location. Prior to working with this chemical, personnel should be trained on its proper handling and
storage. Store in tightly closed containers in a cool, wellventilated area | | Degradation | Methidathion is rapidly hydrolysed in alkaline solution but it is relatively
stable in neutral and slightly acidic media. The DT50 for hydrolysis at pH
13 (25 °C) was 30 min (PM). | | Toxicity evaluation | The acute oral LD50 for rats is 25–54 mg/kg. Inhalation LC50
(4 h) for rats is 3.6 mg/L air. NOEL (2 yr) for rats is
4 mg/kg diet (0.2 mg/kg/d). ADI is 1 μg/kg b.w. Methidathion
administered to animals is rapidly metabolized
and excreted. | | Waste Disposal | Treat with strong alkali, mix
with soil and bury in the case of small quantities.
For large quantities, use incineration with effluent gas
scrubbing | | Precautions | Occupational workers should be very careful during use and chemical management of methidathion. As this chemical substance is a highly toxic pesticide, it has been grouped by the US EPA as toxicity class I. The containers and labels of the products should bear the signal word DANGER. Methidathion is an RUP, except for use in nurseries, and on saffl ower and sunfl owers. |
| | Methidathion Preparation Products And Raw materials |
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