Fenthion
Names | |
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Preferred IUPAC name
O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate | |
Other names
• Dimethoxy-[3-methyl-4-(methylthio)phenoxy]-thioxophosphorane
• O,O-Dimethyl O-[3-methyl-4-(methylthio)phenyl] phosphorothioate • O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioate | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.000.211 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H15O3PS2 | |
Molar mass | 278.33 g/mol |
Appearance | colorless, almost odorless liquid; 95-98% pure fenthion is a brown oily liquid with a weak garlic odor |
Density | 1.250 g/cm3 (at 20 °C / 4 °C) |
Melting point | 7 °C (45 °F; 280 K) |
Boiling point | 87 °C (189 °F; 360 K) at 0.01 mmHg |
54-56 ppm (at 20 °C) | |
Solubility in glyceride oils, methanol, ethanol, ether, acetone, and most organic solvents, especially chlorinated hydrocarbons | soluble |
Vapor pressure | 4 • 10−5 mmHg (at 20 °C) |
Pharmacology | |
QP53BB02 (WHO )
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Hazards | |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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none[2] |
REL (Recommended)
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None established[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).
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Fenthion is an
Uses
Fenthion is a contact and stomach insecticide used against many biting insects. It is particularly effective against fruit flies, leaf hoppers, cereal bugs, stem borers, mosquitoes, animal parasites, mites, aphids, codling moths, and weaver birds. It has been widely used in sugar cane, rice, field corn, beets, pome and stone fruit, citrus fruits, pistachio, cotton, olives, coffee, cocoa, vegetables, and vines.[3]
Based on its high toxicity on birds, fenthion has been used to control weaver birds and other pest-birds in many parts of the world. Fenthion is also used in cattle, swine, and dogs to control lice, fleas, ticks, flies, and other external parasites.[3][4][5]
Amid concerns of harmful effects on environment, especially birds,
Some common trade names for fenthion are Avigel, Avigrease, Entex, Baytex, Baycid, Dalf, DMPT, Mercaptophos, Prentox, Fenthion 4E, Queletox, and Lebaycid.[3] Fenthion is available in dust, emulsifiable concentrate, granular, liquid concentrate, spray concentrate, ULV, and wettable powder formulations.
Synthesis
Fenthion can be synthesized by condensation of 4-methylmercapto-m-cresol and
Health effects
Fenthion exposure to general population is quite limited based on its bioavailability. Common form of fenthion exposure is occupation related, and occurs through dermal contact or inhalation of dust and sprays.[6] Another likely means of contamination is through ingestion of food, especially, if it has been applied quite recently with fenthion. So far, ingestion is the most likely severe poisoning case on humans and animals.[1] To avoid this, crops applied with fenthion should be allowed enough degradation time before harvesting. Normally, two to four weeks time is enough depending upon the type of crop.
Fenthion poisoning is consistent with symptoms of other organophosphate effects on human health. Primarily, the effect is cholinesterase inhibition.
Acute toxicity
Acute poisoning of fenthion results in miosis (pinpoint pupils), headache, nausea/vomiting, dizziness, muscle weakness, drowsiness, lethargy, agitation, or anxiety. If the poisoning is moderate or severe, it results in chest tightness, breathing difficulty, hypertension, abdominal pain, diarrhea, heavy salivation, profuse sweating, or fasciculation.[4][6]
Chronic toxicity
Chronic effect of fenthion has not been reported.[6]
Environmental effects
Despite short half-life in the environment, fenthion toxicity is highly significant to birds and estuarine/marine invertebrates.
Degradation in nature
Photodegradation and biodegradation are common mechanisms of fenthion degradation in the environment. In the atmosphere, vapor phase fenthion reacts rapidly with photochemically produced hydroxyl radicals, and its half-life is about 5 hours. In soil and water, photodegradation is again predominant mechanism if there is enough presence of sunlight. Under normal aquatic environment, half-life of fenthion in water is 2.9 to 21.1 days.[1] It may be photodynamically, chemically or biologically degraded. The degradation mechanisms can be hydrolysis, oxidation, and/or alkylation-dealkylation, which are dependent on the presence of light, temperature, alkali, or enzymatic activity.[7]
In soil, fenthion degradation ranges from four to six weeks and it occurs through photodegradation as well as anaerobic or non-photolytic organisms. However, soil particles strongly adsorb fenthion making it less susceptible to percolate with water through the soil.[6]
Regulation
The examples and perspective in this section may not represent a worldwide view of the subject. (April 2017) |
India
Fenthion was used in India for more than 30 years as a larvicide for control of mosquito larvae. The compound was on the review list of Central Insecticide Board in India and they decided to ban the product due to high toxicity for usage. The product cannot be manufactured in India after January 2017. The government of India has released the Gazzetta notification with that effect of banning many toxic insecticides such as fenthion and DDVP.[8]
Australia
Fenthion and dimethoate were widely used to combat the Queensland fruit fly (Bactrocera tryoni), a species that has caused more than $28.5 million a year in damage to Australian fruit crops. However, it was banned in 2011 due to safety concerns.[9] Other insecticides and control techniques are being investigated to control the spread of this pest.
References
- ^ a b c d e HSDB. (2003). Hazardous Substance Data Bank: Fenthion. National Library of Medicine: National Toxicology Program. Available at http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB Accessed April 29, 2009.
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0285". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c d e EXTOXNET. (2003). Pesticide information Profile for Fenthion. Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. Available at http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenthion-ext.html Accessed April 25, 2009.
- ^ a b c USEPA. (2001). Interim Reregeistration Eligibility Decision for Fenthion. United States Environmental Protection Agency. Available at http://www.epa.gov/pesticides/reregistration/REDs/0290ired.pdf Accessed April 25, 2009.
- ^ APVMA. (2005). Fenthion Review - Frequently asked questions. Australian Pesticides and Veterinary Medicines Authority. Available at http://www.apvma.gov.au/chemrev/fenthion_faq.shtml Archived 2009-05-19 at the Wayback Machine Accessed April 26, 2009.
- ^ a b c d e ASTDR. (2005). Toxicologic Information about Insecticides Used for Eradicating Mosquitoes (West Nile Virus Control). Department of Health and Human Services: Agency for Toxic Substances and Disease Registry. Available at [1] Accessed April 25, 2009.
- S2CID 39628676.
- ^ "DRAFT ORDER - Banning of Pesticides Order, 2016".
- ISSN 0261-2194.
External links
- Fenthion in the Pesticide Properties DataBase (PPDB)