Diazinon

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Diazinon
Diazinon-Structural Formula V1.svg
Diazinon-Molecule-3D-balls-by-AHRLS.png
Names
Preferred IUPAC name
O,O-Diethyl O-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl] phosphorothioate
Other names
Diethoxy-[(2-isopropyl-6-methyl-4-pyrimidinyl)oxy]-thioxophosphorane
Basudin
Diazide
Spectracide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.795 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3 Yes check.svgY
    Key: FHIVAFMUCKRCQO-UHFFFAOYSA-N Yes check.svgY
  • S=P(OCC)(OCC)Oc1nc(nc(c1)C)C(C)C
Properties
C12H21N2O3PS
Molar mass 304.34 g·mol−1
AppearanceColorless to dark brown liquid
Odor faint, ester-like
Density 1.116-1.118 g/cm3 at 20 °C [1]
Boiling point decomposes [2]
40 mg/L [3]
log P 3.81 (octanol/water) [4]
Pharmacology
QP53AF03 ( WHO )
Hazards
Flash point 82 °C; 180 °F; 355 K [2]
NIOSH (US health exposure limits):
PEL (Permissible)
none [2]
REL (Recommended)
TWA 0.1 mg/m3 [skin] [2]
IDLH (Immediate danger)
N.D. [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diazinon (IUPAC name: O,O-Diethyl O-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl] phosphorothioate, INN - Dimpylate), a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company (later Novartis and then Syngenta). It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks [5] but it is still approved for agricultural uses. An emergency antidote is atropine. [6]

Contents

Specific Health Risks: Routes of contact for Diazinon include breathing it, consuming it, or contact with skin. The negative health effects when in contact with Diazinon includes eye watering, drool or runny nose, not having any appetite, throwing up, intense coughing, abdominal pain, or even stiffness in various muscles/paralysis [7] . Headaches can also be health risks [8] . Some other physiological effects include pinpoint pupils, increased heart rate, seizures, or even coma. Larger exposure to diazinon is known to yield these risks. If it is a smaller exposure, the symptoms may be reduced such as just a runny nose or some eye watering [9] . One thing to note is that while Diazinon has many different health risks, the EPA has not categorized it as a carcinogen [10] .

History

Diazinon was developed in 1952 by the Swiss company Ciba-Geigy (now Novartis) to replace the formerly dominant insecticide DDT. In 1939, the chemist Paul Hermann Müller from the then-independent Geigy company had discovered that DDT was effective against malaria-bearing insects. This capability made use of DDT important enough that Müller even received the 1948 Nobel Prize in Medicine.[ citation needed ]

However, as the decades following the award passed, DDT was found to be such an environmental danger that developed countries and eventually world-level organizations banned the insecticide for all purposes except for combating disease-vector insects, leading Ciba-Geigy to research alternatives.[ citation needed ]

Diazinon became available for mass use in 1955, while DDT production tapered. Before 1970, diazinon had issues with contaminants in its solution; but by the 1970s, alternative purification methods were used to reduce the residual, unwanted materials. [ citation needed ]

After this processing improvement, diazinon became an all-purpose, indoor-and-outdoor, commercial pest control product. In 2004, the US outlawed residential use of diazinon when the EPA determined that its ability to damage the nervous system posed a risk to human health (especially the health of children). [5] The chemical is still used for industrial agricultural purposes.

Synthesis

According to the German Patent bureau, the industrial synthesis of diazinon is as follows:

β-isobutyrylaminocrotonic acid amine was cyclized with NaOR (R is either a hydrogen or aliphatic chain of 1 to 8 carbons) in a mixture of 0 to 100% by weight of water and an alcohol having 1 to 8 carbon atoms, above 90°C (but below the boiling point of the mixture used). Sodium pyrimidinolate was precipitated out in an inert solvent, such as benzene, with simultaneous removal of the water formed. The potassium salt is then reacted with diethylthiophosphoryl chloride by heating for several hours. When the reaction finished, the potassium chloride formed was washed with water and the solvent was removed under reduced pressure leaving diazinon.[ citation needed ]

Metabolism and mechanism of action

Diazinon functions as an acetylcholinesterase (AChE) inhibitor. This enzyme breaks down the neurotransmitter acetylcholine (ACh) into choline and an acetate group. [11] The inhibition of AChE causes an abnormal accumulation of ACh in the synaptic cleft.[ citation needed ]

When diazinon enters the body, it is oxidatively decomposed to diazoxon, an organophosphate compound that is much more poisonous than diazinon; it mainly causes the inhibition of AChE. [12] The conversion of diazinon to diazoxon (Reaction 1) is performed by the liver microsomal enzyme system and requires O2 and NADPH. Diazinon can also be decomposed via oxidation in the liver (Reaction 2). Both reactions are possible, and likely are catalyzed nonspecifically by the same mixed function oxidase. Diazoxon is further broken down by hydrolases in the microsomal and other subcellular functions within the liver (Reaction 3). Mammals metabolize diazoxon with a half-life of 2 to 6 weeks. Insects lack this hydrolysis step, which allows the toxic substance to accumulate rapidly; the detoxification of diazoxon is processed through the microsomal mixed function oxidase system. Although not fully understood, it is believed that this is the cause for the selectivity of diazinon against insects. After the hydrolysis or oxidation diazinon is broken down further (Reaction 4).[ citation needed ]

The mechanism, described above of the biotransformation of Diazinon Diazinon Biotransformation Mechanism.pdf
The mechanism, described above of the biotransformation of Diazinon

Removal of diazinon

To date, several methods such as electrochemistry, adsorption, enzymatic biodegradation, and photocatalysis have been tested for the elimination of diazinon from aqueous solutions. The removal of organophosphates (OPE) from water by adsorption techniques is regarded as one of the competitive methods because of its simple operation and low cost. Development of new adsorbents with high adsorption capacities is very important for removal of the OPE pollutants in the environment. [13]

Banning of Diazinon

During the Clinton Era, President Clinton signed a tougher pesticide law in 1996. Diazinon was banned from use as an agricultural insecticide. At the time 80% of United States could find Diazinon in their residential products. In fact it still may be in use in certain households, as it is still used and considered legal in 14 states including California. Yet with the ban starting in 2004, having had 20 years pass, states which have accepted that ban have had hardware stores and other suppliers report that they have "ran out" of products with diazinon. These states which continue to use Diazinon is their products consider their risks low, yet its greatest affect is through inhalation and skin contact. Certain environmental groups continue to protest these states which still continue its use. [14]

Toxicity and effects on animals

Diazinon is considered to be of relatively high toxicity for vertebrates. The common method of administering diazinon is absorption although inhalation is possible as well. The observed toxification symptoms conform to other acetylcholinesterase inhibitors. Symptoms are as follows:

Lethal DoseObservations
LD50
  • 214 mg•kg−1 (human, oral, TDLo) (2,3)
  • 66 mg•kg−1 (rat, oral, LD50) (2,4)
  • 17 mg•kg−1 (mouse, oral, LD50) (2,5)

On the other hand, in regard to chronic toxicity, the WHO/FAO joint committee on pesticide residues gives the admissible daily intake (ADI) to be 0.005 mg/kg of body weight, while the Australian Pesticides and Veterinary Medicine authority gives the no-observed-adverse-effect-level (NOAEL) to be 0.02 mg/kg of body weight for adults.

Symptoms in humans

Intoxication of diazinon produces the following signs and symptoms:

Typically treatments will vary depending on exposure and method of administration of the toxin. Critical biomarkers such as urine samples, blood content and heart rates are measured while detoxifying the patient. Common treatments for patients with diazinon poisoning include:

Patients that continue to improve over the first 4 to 6 hours (after medical treatment) usually recover unscathed. Prolonged treatment often is needed to reverse the poisoning, including intensive care hospitalization and long-term therapy. Some toxicity may persist for weeks or months, or even longer.[ citation needed ]

Efficacy and side effects

Diazinon is a contact insecticide which kills insects by altering normal neurotransmission within the nervous system of the insect. As mentioned above, diazinon inhibits the enzyme acetylcholinesterase (AChE), which hydrolyzes the neurotransmitter acetylcholine (ACh) in cholinergic synapses and neuromuscular junctions. This results in abnormal accumulation of ACh within the nervous system. Diazinon, although a thiophosphoric ester, shares a common mechanism of toxicity with other organophosphate insecticides such as chlorpyrifos, malathion and parathion, and is not very effective against the organophosphate-resistant insect populations.[ citation needed ]

Symptoms of acute diazinon exposure develop in minutes to hours following exposure, depending on the exposure pathway. The initial symptoms of humans are nausea, dizziness, salivation, headache, sweating, lacrimation, and rhinorrhea. The symptoms can progress to vomiting, abdominal cramps, diarrhea, muscle twitching, weakness, tremor, a lack of coordination and miosis. Furthermore, some studies have even reported some psychiatric side effects including memory loss, confusion, and depression.[ citation needed ]

Because diazinon is fat soluble, there is potential for delayed toxicity if significant amounts of diazinon are stored in fatty tissues. Intermediate syndrome generally occurs within 24–96 hours after exposure. Intermediate syndrome in humans is characterized by difficulty breathing and muscular weakness, often in the face, neck and proximal limb muscles. Cranial nerve palsies and depressed tendon reflexes have also been reported.[ citation needed ]

Studies have suggested that exposure to some organophosphate pesticides can result in long-term neurological problems including organophosphate-induced delayed neuropathy (weakness or paralysis as well as paresthesia in the extremities); however, reports of these symptoms following diazinon exposures are rare. Human who have been poisoned show increased levels of serum amylase and glucose as well as elevated urinary diastase levels accompanied by symptoms considered to be indicative of acute pancreatitis.[ citation needed ]

A study found that 10% of 21 typically developing children show 2-isopropyl-6-methyl-4-pyrimidinol (IMPy, a metabolite of diazinon) in molars. Molars from the two oldest subjects contained the largest concentrations of IMPy. And this concentration in molars may be a biomarker of perinatal exposure and during molar formation. [16]

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides have the potential to significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.

<span class="mw-page-title-main">Parathion</span> Chemical compound

Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. The basic structure is shared by parathion methyl.

<span class="mw-page-title-main">Malathion</span> Chemical compound

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

<span class="mw-page-title-main">Chlorfenvinphos</span> Chemical compound

Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

<span class="mw-page-title-main">Chlorpyrifos</span> Chemical compound

In organic chemistry, chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.

<span class="mw-page-title-main">Ethion</span> Chemical compound

Ethion (C9H22O4P2S4) is an organophosphate insecticide. Ethion is known to affect a neural enzyme called acetylcholinesterase and prevent it from working.

<span class="mw-page-title-main">Azinphos-methyl</span> Chemical compound

Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan. Like other pesticides in this class, it owes its insecticidal properties to the fact that it is an acetylcholinesterase inhibitor. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

<span class="mw-page-title-main">Dichlorvos</span> Insect killing chemical, organophosphate

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961 and has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. Since 1988, dichlorvos cannot be used as a plant protection product in the EU.

<span class="mw-page-title-main">Phosmet</span> Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

<span class="mw-page-title-main">Organophosphate poisoning</span> Toxic effect of pesticides

Organophosphate poisoning is poisoning due to organophosphates (OPs). Organophosphates are used as insecticides, medications, and nerve agents. Symptoms include increased saliva and tear production, diarrhea, vomiting, small pupils, sweating, muscle tremors, and confusion. While onset of symptoms is often within minutes to hours, some symptoms can take weeks to appear. Symptoms can last for days to weeks.

<span class="mw-page-title-main">Chlorethoxyfos</span> Chemical compound

Chlorethoxyfos is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is registered for the control of corn rootworms, wireworms, cutworms, seed corn maggot, white grubs and symphylans on corn. The insecticide is sold under the trade name Fortress by E.I. du Pont de Nemours & Company.

<span class="mw-page-title-main">Disulfoton</span> Chemical compound

Disulfoton is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is manufactured under the name Di-Syston by Bayer CropScience. Disulfoton in its pure form is a colorless oil but the technical product used in vegetable fields is dark and yellowish with a sulfur odor. Disulfoton is processed as a liquid into carrier granules, these granules are mixed with fertilizer and clay to be made into a spike, designed to be driven into the ground. The pesticide is absorbed over time by the roots and translocated to all parts of the plant. The pesticide acts as a cholinesterase inhibitor and gives long lasting control.

<span class="mw-page-title-main">Propoxur</span> Chemical compound

Propoxur (Baygon) is a carbamate non-systemic insecticide, produced from catechol, and was introduced in 1959. It has a fast knockdown and long residual effect, and is used against turf, forestry, and household pests and fleas. It is also used in pest control for domestic animals, Anopheles mosquitoes, ants, gypsy moths, and other agricultural pests. It can also be used as a molluscicide.

<span class="mw-page-title-main">Sulfotep</span> Chemical compound

Sulfotep (also known as tetraethyldithiopyrophosphate and TEDP) is a pesticide commonly used in greenhouses as a fumigant. The substance is also known as Dithione, Dithiophos, and many other names. Sulfotep has the molecular formula C8H20O5P2S2 and belongs to the organophosphate class of chemicals. It has a cholinergic effect, involving depression of the cholinesterase activity of the peripheral and central nervous system of insects. The transduction of signals is disturbed at the synapses that make use of acetylcholine. Sulfotep is a mobile oil that is pale yellow-colored and smells like garlic. It is primarily used as an insecticide.

<span class="mw-page-title-main">Ethoprophos</span> Chemical compound

Ethoprophos (or ethoprop) is an organophosphate ester with the formula C8H19O2PS2. It is a clear yellow to colourless liquid that has a characteristic mercaptan-like odour. It is used as an insecticide and nematicide and it is an acetylcholinesterase inhibitor.

<span class="mw-page-title-main">Terbufos</span> Chemical compound

Terbufos is a chemical compound used in insecticides and nematicides. It is part of the chemical family of organophosphates. It is a clear, colourless to pale yellow or reddish-brown liquid and sold commercially as granulate.

<span class="mw-page-title-main">Parathion methyl</span> Chemical compound

Parathion methyl, or methyl parathion, is an organophosphate insecticide, possessing an organothiophosphate group. It is structurally very similar to parathion-ethyl. It is not allowed for sale and import in nearly all countries around the world, while a few allow it under subject to specified conditions only.

Carbamate poisoning is poisoning due to exposure to carbamates, which are commonly sold as pesticides around the world. In most respects, it is similar to organophosphate poisoning, though typically less severe or requiring a larger amount of the chemical before symptoms appear.

References

  1. ↑ Budavari, S., ed. (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck. p. 508.
  2. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0181". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Sharom, M.S.; Miles, J.R.W.; Harris, C.R.; McEwen, F.L. (1980). "Behaviour of 12 insecticides in soil and aqueous suspensions of soil and sediment". Water Research. 14 (8): 1095–100. Bibcode:1980WatRe..14.1095S. doi:10.1016/0043-1354(80)90158-X.
  4. ↑ Hansch, Corwin; Leo, Albert; Hoekman, David (1995). Exploring QSAR: Volume 2: Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society. p. 106. ISBN   978-0-8412-2991-4.
  5. 1 2 Cone, Marla (1 Jan 2005). "EPA Takes Pest Killer Diazinon Off the Shelves". Los Angeles Times. Retrieved 2 Jul 2020.
  6. ↑ Geller, Robert J.; Lopez, Gaylord P.; Cutler, Stephen; Lin, Diana; Bachman, George F.; Gorman, Susan E. (2003). "Atropine availability as an antidote for nerve agent casualties: Validated rapid reformulation of high-concentration atropine from bulk powder". Annals of Emergency Medicine. 41 (4): 453–6. doi:10.1067/mem.2003.103. PMID   12658242.
  7. ↑ "Diazinon General Fact Sheet". npic.orst.edu. Retrieved 2024-03-14.
  8. ↑ Dahlgren, J. G.; Takhar, H. S.; Ruffalo, C. A.; Zwass, M. (2004). "Health effects of diazinon on a family". Journal of Toxicology. Clinical Toxicology. 42 (5): 579–591. doi:10.1081/clt-200026979. ISSN   0731-3810. PMID   15462149.
  9. ↑ "Diazinon | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.
  10. ↑ "Diazinon | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.
  11. ↑ "Diazinon Technical Fact Sheet". National Pesticide Information Center. NPIC. Retrieved 31 May 2019.
  12. ↑ Kretschmann, Andreas; et al. (2011). "Mechanistic Toxicodynamic Model for Receptor-Mediated Toxicity of Diazoxon, the Active Metabolite of Diazinon, in Daphnia magna". Environmental Science & Technology. 45 (11): 4980–4987. Bibcode:2011EnST...45.4980K. doi:10.1021/es1042386. PMID   21539304. S2CID   31463849.
  13. ↑ Amani, M. A; Latifi, A. M; Tahvildari, K; Karimian, R (2017). "Removal of diazinon pesticide from aqueous solutions using MCM-41 type materials: Isotherms, kinetics and thermodynamics". International Journal of Environmental Science and Technology. 15 (6): 1301–1312. doi:10.1007/s13762-017-1469-x. S2CID   104194226.
  14. ↑ Cone, Marla (2005-01-01). "EPA Takes Pest Killer Diazinon Off the Shelves". Los Angeles Times. Retrieved 2024-03-14.
  15. ↑ www.apvma.gov.au(PDF) https://web.archive.org/web/20130419083945/http://www.apvma.gov.au/products/review/docs/diazinon_hh_tox_part_2.pdf. Archived from the original (PDF) on 2013-04-19.{{cite web}}: Missing or empty |title= (help)
  16. ↑ Camann, David E.; Schultz, Stephen T.; Yau, Alice Y.; Heilbrun, Lynne P.; Zuniga, Michelle M.; Palmer, Raymond F.; Miller, Claudia S. (March 2013). "Acetaminophen, pesticide, and diethylhexyl phthalate metabolites, anandamide, and fatty acids in deciduous molars: potential biomarkers of perinatal exposure". Journal of Exposure Science and Environmental Epidemiology. 23 (2): 190–196. doi: 10.1038/jes.2012.71 . ISSN   1559-0631. PMID   22805989.
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