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 M
1 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
Crystalline solid. Almost insoluble in
water; soluble in common organic solvents.
Chemical Properties
Methidathion is a colorless crystalline solid.
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.
Production Methods
The industrial synthesis of methidathion begins with the preparation of the 1,3,4-thiadiazole ring. This heterocyclic core is synthesised by cyclising appropriate hydrazine and carboxylic acid derivatives, followed by methoxylation to introduce the methoxy group at the 5-position. The resulting thiadiazole intermediate is then reacted with O,O-dimethyl phosphorodithioic chloride, a reactive phosphorus-containing compound, under controlled conditions to form the phosphorodithioate ester linkage. The reaction is typically carried out in organic solvents like toluene or xylene, with temperature and pH carefully regulated to ensure high yield and minimal by-products.
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
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.
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.
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.
Mechanism of action
Non-systemic with contact and stomach action. Acetylcholinesterase (AchE) inhibitor.
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
Potential Exposure
Those involved in the manufacture, formulation, and application of this nonsystemic insecticide.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Speed in removing material from skin is of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Keep victim quiet and maintain normal body temperature. Effects may be delayed; keep victim under observation.
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 PS
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; DT
50 in soil
is 3–18 d.
storage
Color Code—Blue: Health Hazard/Poison: Store in a secure poison location. Prior to working with this chemical you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, well-ventilated area.
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 DT
50 for hydrolysis at pH
13 (25 °C) was 30 min (PM).
Toxicity evaluation
The acute oral LD
50 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.
Incompatibilities
None listed
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.
References
[1] BAYO F. Insecticides Mode of Action in Relation to Their Toxicity to Non-Target Organisms[J]. Journal of Environmental and Analytical Toxicology, 2012, 13 1: 1-9. DOI:
10.4172/2161-0525.s4-002[2] R. J. HART. EFFICIENCY AND SAFETY OF METHIDATHION APPLIED AS A POUR-ON SYSTEMIC INSECTICIDE FOR CONTROL OF CATTLE LICE[J]. Australian Veterinary Journal, 1979, 55 12: 575-579. DOI:
10.1111/j.1751-0813.1979.tb07050.x[3] JANE C.F. CHANG William R C James A Walberg. One-year dietary toxicity study with methidathion in beagle dogs[J]. Fundamental and Applied Toxicology, 1992, 19 2: Pages 307-314. DOI:
10.1016/0272-0590(92)90165-e[4] TURHAN YAVUZ. Cardiotoxicity in rats induced by methidathion and ameliorating effect of vitamins E and C.[J]. Human & Experimental Toxicology, 2004, 23 7: 323-329. DOI:
10.1191/0960327104ht456oa
Pesticide Type
Insecticide; Acaricide
