Dichlorvos
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IUPAC name
2,2-Dichlorovinyl dimethyl phosphate
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Other names
DDVP, Vapona[1]
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Identifiers | |
3D model (
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.000.498 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C4H7Cl2O4P | |
Molar mass | 220.97 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dichlorvos (2,2-dichlorovinyl dimethyl phosphate, commonly abbreviated as an DDVP[1]) 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. It has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects.[2] Since 1988, dichlorvos cannot be used as a plant protection product in the EU.[3]
Use
Dichlorvos is effective against mushroom flies,
Properties
Dichlorvos is a colourless liquid
Mechanism of action
Dichlorvos, like other organophosphate insecticides, inhibits acetylcholinesterase, associated with the nervous systems of insects. Evidence for other modes of action, applicable to higher animals, have been presented.[7][8] It is claimed to damage DNA of insects.[9]
Regulation
The
Between 2000 and 2013, thirty-one cases of acute dichlorvos pest strip-related illness were reported to the National Institute for Occupational Safety and Health (NIOSH) sentinel system. 65% of the 31 cases involved DDVP misuse contrary to instructions and safety labels.[16] Common violations included pest strip use in occupied, poorly-ventilated living areas (e.g., kitchens, bedrooms), lack of skin protection, cutting and tearing strips, and using a heater and fan to accelerate vapor dissemination from strips.
Production
Dichlorvos can be produced by dehydrochlorinating trichlorfon in an aqueous alkali at 40-50 °C. It is also produced by the reaction of trimethyl phosphate and chloral.[17] As of 1990, it is produced in Argentina, Brazil, Germany, India, Israel, Japan, the Republic of Korea, Mexico, the USA, Switzerland, Sweden, Spain, and the Netherlands.[18]
Environment
Dichlorvos enters the air, water, and soil when it is used and manufactured. It also can enter the environment when waste containing dichlorvos is disposed of in landfills. Dichlorvos is soluble in water, so it dissolves when it enters a body of water. Dichlorvos evaporates into the air easily, but is broken down by water vapor such as humidity. It does not bind to soil, but dichlorvos is broken down slower in soil than in the air. The broken down products are far less harmful than dichlorvos is. Dichlorvos is not stored in plants, animals, or humans.[19]
Safety
People can be exposed to dichlorvos in the workplace by breathing it in, skin absorption, swallowing it, and eye contact. The Occupational Safety and Health Administration (OSHA) has set the legal limit (permissible exposure limit) for dichlorvos exposure in the workplace as 1 mg/m3 over an 8-hour workday. The National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 1 mg/m3 over an 8-hour workday. At levels of 100 mg/m3, dichlorvos is immediately dangerous to life or health (IDLH).[20]
Treatment Technology
Different physicochemical methods have been developed for the removal of DDVP from contaminated environments, and microbial degradation is regarded as a promising method to solve several harmful residuals caused by DDVP. The biodegradation mechanism of many OPs has been studied deeply, especially for the methyl parathion, whose degradation genes and enzymes were cloned and purified. There is a need to select more useful strains, since only a few bacteria have been studied thoroughly in relation to the functional enzymes and genes.[21]
Effects on humans
Since it is an
It is also known to affect DNA replication in bacteria.[22]
Dose | Organism | Time |
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15 mg/m3 | rat | 4 h |
13 mg/m3 | mouse | 4 h |
Dose | Organism | Route |
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100 mg/kg | dog | oral |
61 mg/kg | mouse | oral |
10 mg/kg | rabbit | oral |
17 mg/kg | rat | oral |
Acute Effects
The substance is irritating to the skin the substance may cause effects on the nervous system by a cholinesterase inhibiting effect exposure above the OEL could cause death. The effects may be delayed. Medical observation is indicated[24]
Tests involving acute exposure of rats, mice, and rabbits have demonstrated dichlorvos to have high to extreme acute toxicity from oral or dermal exposure and extreme acute toxicity from inhalation[25]
Long-Term Effects
Prolonged contact with skin may cause dermatitis and skin sensitization.[24] If drinking water contaminated by dichlorvos is ingested long-term it may cause oral cancer.[25]
Reproductive/Developmental Effects
There is no information available on the reproductive or developmental effects of dichlorvos in humans. In studies conducted with rat models, birth defects in fetal rats were observed. Mouse models also demonstrated sperm abnormalities. However, studies with other animal subjects found no birth defects.[26]
In popular culture
Dichlorvos is mentioned in
See also
- Metrifonate (converts into dichlorvos)
- Naled (can convert into dichlorvos)
References
- ^ a b "Dichlorvos". Haz-Map. U.S. National Library of Medicine. August 2015. Archived from the original on 2019-06-24. Retrieved 2015-10-13.
- .
- ^ "Which Pesticides are Banned in Europe?" (PDF). pan-europe.info. April 2008.
- PMID 4576326.
- ^ Entry on Dichlorvos. at: Römpp Online. Georg Thieme Verlag, retrieved 2014-02-07.
- ^ a b c d e Record of Dichlorvos in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2017-01-10.
- PMID 18049927.
- PMID 17936460.
- PMID 20148102.
- PMID 9693077.
- ^ "Dichlorvos (DDVP): Deletion of Certain Uses and Directions". U.S. Environmental Protection Agency: Office of Pesticide Programs. April 19, 1995. pp. 19580–19581.
Docket Control Number OPP-38511
- ^ Wines M (11 September 2014). "Pesticide Levels in Waterways Have Dropped, Reducing the Risks to Humans". The New York Times.
- ^ Brooks M (May 17, 2010). "Organophosphate Pesticides Linked to ADHD". Medscape.
- PMID 20478945.
- .
- ISSN 1059-1028. Retrieved 2024-03-14.
- )
- PMID 1842580, retrieved 2024-03-14
- ^ "Dichlorvos | Public Health Statement | ATSDR". wwwn.cdc.gov. Retrieved 2024-03-14.
- ^ a b NIOSH Pocket Guide to Chemical Hazards. "#0202". National Institute for Occupational Safety and Health (NIOSH).
- PMID 34071247.
- ^ "Preferential Effect of Dichlorvos(Vapona) on Bacteria Deficient in DNA Polymerase" (PDF). Cancer Research.
- ^ a b "Dichlorvos". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "ICSC 0690 - DICHLORVOS". www.ilo.org. Retrieved 2024-03-14.
- ^ a b "Dichlorvos" (PDF). EPA's integrated risk information system (IRIS). EPA. January 2000.
- ^ "Dichlorvos" (PDF). January 2000. Retrieved March 14, 2024.
- LCCN 72-79705.
External links
- Extension Toxicology Network - Pesticide Information Profiles - Dichlorvos (last maintained 1996)
- CDC - NIOSH Pocket Guide to Chemical Hazards
- Australian Pesticides & Veterinary Medicines Authority Chemical Review Program - Dichlorvos
- Material Safety Data Sheet (MSDS) for Dichlorvos
- Raeburn P (August 2006). "Slow-acting". Scientific American. 295 (2): 26. PMID 16866280.
- BBC News: Insecticide ban amid cancer fears