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Dimethoate is a widely used
organophosphate In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered ...
insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...
and
acaricide Acaricides are pesticides that kill members of the arachnid subclass '' Acari'', which includes ticks and mites. Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields. Termi ...
. It was patented and introduced in the 1950s by
American Cyanamid American Cyanamid Company was an American manufacturing conglomerate. It began as a fertilizer company and added many additional lines of business before merging with American Home Products in 1994. The combined company sold off most of its di ...
. Like other organophosphates, dimethoate is an
acetylcholinesterase inhibitor Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level an ...
which disables
cholinesterase The enzyme cholinesterase (EC 3.1.1.8, choline esterase; systematic name acylcholine acylhydrolase) catalyses the hydrolysis of choline-based esters: : an acylcholine + H2O = choline + a carboxylate Several of these serve as neurotransmitte ...
, an
enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
essential for
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain, spinal cord and retina. The CNS is so named because the brain integrates the received information and coordinates and influences the activity o ...
function. It acts both by contact and through ingestion. It is readily absorbed and distributed throughout plant tissues, and is degraded relatively rapidly. One of the breakdown products of dimethoate is omethoate, a potent cholinesterase inhibitor, is ten times more toxic than its parent compound.


Uses

Dimethoate is a general use insecticide for combatting insects such as aphids, mites, beetles, weevils, and leafhoppers. Dimethoate is formulated as emulsifiable concentrates or wettable powders to be applied primarily as foliar sprays. The majority of the approximately 800.000 kg (1.8 million pounds) of dimethoate used annually in the U.S. is accounted for by applications on alfalfa, wheat, cotton, and corn crops. In 2005, dimethoate usage was cancelled in the U.S. for use on apples, broccoli raab, cabbage, collards, grapes, head lettuce, and spinach due to being identified as significant dietary risk contributors. Dimethoate also has applications as a form of botfly and mite control in livestock. As of 2000, dimethoate is cancelled for usage in residential and non-agriculture applications in the U.S


Environment

Dimethoate is relatively non-persistent, but highly mobile in the environment due to its high solubility in water and low adsorption in soil. The half-life of dimethoate in soil has been shown to range from 2.5 to 31 days depending on the type of soil and its moisture content. The half-life of dimethoate is shorter in moist soil due the action of microbial degradation. Breakdown of dimethoate by hydrolysis in water is highly dependent on temperature and pH, with the half-life ranging from 12 to 423 days.


Health effects


Routes of exposure

Exposure of the general population to dimethoate and its breakdown product omethoate can happen through consumption of contaminated food or water. Workers involved in the application or manufacture of dimethoate are typically exposed through contact with skin, or through inhalation of aerosols and dust.


Acute exposure in humans

In mammals, dimethoate has an LD50 of 150 mg/kg bodyweight in mice and 400 mg/kg bodyweight in rats. Acute exposure through oral, dermal, or inhalation routes can cause symptoms such as diarrhea, nausea, sweating, blurred vision, difficulty breathing, and slowed heartbeat. Relapse situations where the patient appears to have stabilized before getting worse have been associated with higher exposure doses. Respiratory ailments, cholinesterase inhibitor exposure, impaired cholinesterase production, or liver malfunction can play a role in potentiating toxicity.


Chronic exposure in humans

Chronic exposure to dimethoate can result in symptoms such as disorientation, irritability, impaired memory and concentration, nightmare, and speech difficulties. Chronic exposure as also been associated with nausea, loss of appetite, and malaise. Under normal conditions the chances of teratogenic, mutagenic, or carcinogenic effects from chronic exposure are low.


Fruit fly control efforts

The Queensland fruit fly, or ''
Bactrocera tryoni ''Bactrocera tryoni'', the Queensland fruit fly, is a species of fly in the family Tephritidae in the insect order Diptera. ''B. tryoni'' is native to subtropical coastal Queensland and northern New South Wales. They are active during the day, b ...
'', is a tephritid fly species that has caused more than $28.5 million a year in damage to Australian fruit crops. In order to combat infestation, farmers treated crops with dimethoate and
fenthion Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as mo ...
. In 2011 the Australian Pesticides and Veterinary Medicines Authority (APVMA) banned the use of dimethoate containing products on food producing plants in home gardens, as well as on a variety of fruits, berries, cucurbits, and vegetables. In September 2023, due to concerns that dimethoate and omethoate levels were exceeding acceptable maximum residue limits on avocados and mangoes, the APVMA issued a 12-month suspension notice on the use of dimethoate containing compounds as a post-harvest dip to control fruit flies on certain tropical fruits, including avocados and mangoes.


Trade names

Dimethoate is sold under various trade names, including Cygon, De-fend, Rogor, Rogodan, Rogodial, Roxion, Dimetate, Devigon, Dicap, Dimet, and B-58.


Poisoning incidents

In late October 2020 a Bulgarian farmer, a previous jackpot winner of the national 'toto' lottery drank a glass of the Russian B-58 brand, as of early November 2020 he is hospitalised in a comatose condition, he has a history of psychiatric issues but it is currently unknown whether the incident was accidental or intentional.


References


External links


EPA Report on Dimethoate
Acetylcholinesterase inhibitors Organophosphate insecticides Phosphorodithioates Carboxamides {{Carbohydrate-stub