Monocrotophos Identifiers CAS number PubChem ChemSpider KEGG ChEBI Jmol-3D images Image 1 Properties Molecular formula C7H14NO5P Molar mass 223.2 g/mol Density 1.33 g/cm³ Melting point
120 °C at .0005 mmHg
(what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Monocrotophos is an organophosphate insecticide. It is acutely toxic to birds and humans, and for that reason has been banned in the U.S. and many other countries. Widespread bird kills, especially of Swainson's Hawks, have resulted from the use of monocrotophos.
The pesticide is now out of patent, and is produced by at least 15 manufacturers, although Novartis still produces an estimated 40% of total annual production. Monocrotophos is also manufactured and exported by companies in India, China, Brazil and Argentina. In India, for example, DowElanco makes monocrotophos in a joint venture with the Indian company NOCIL.
Uses and Usage
The total sales monocrotophos comprise roughly 3% (by price, or volume?) of all insecticide products (internationally?). It is registered in approximately 60 countries. Eight of these, accounting for 60% of sales, require detailed data on performance, chemistry, safety and environmental aspects. The remaining 40% are in countries which require only assessments, summaries, or very limited data. The product was withdrawn from use in the US. In the European Union it is registered in Austria, France, Spain, Italy and Greece.
While mainly applied against cotton pests, it is used on citrus, olives, rice, maize, sorghum, sugar cane, sugar beet, peanuts, potatoes, soya beans, vegetables, ornamentals and tobacco.
Use on Crops Imported to the United States
While the use of monocrotophos (mcp) is forbidden on crops grown in the United States, crops that have been grown with it are still directly imported to the US for consumption. Below is a partial and not-exhaustively researched list of these foods. It is in no way intended as an indictment of the places listed, but rather as a resource for people to both better inform their personal choices, and increase awareness of the continued usage of this highly toxic compound. Its impacts will always be most profound on the regions and inhabitants of the regions in which it is used.
- Latin America: Coffee, bananas, melons, green beans, tomatoes, bell peppers, strawberries,
Monocrotophos is classified WHO Ib, highly hazardous, and has been responsible for deaths resulting from accidental or intentional exposure. It is highly toxic orally, as well by inhalation or absorption through the skin. Early symptoms of poisoning may include excessive sweating, headache, weakness, giddiness, nausea, vomiting, hypersalivation, abdominal cramps, diarrhea, blurred vision and slurred speech. Inhalation or skin contact may increase the susceptibility to the pesticide without showing immediate symptoms. The acute oral toxicity for rats (LD50) is 23mg/kg (males) and 18 mg/kg (females). The acute dermal toxicity for a rats is 354 mg/kg. Tests on rabbits indicate it is irritating to eyes and causes reversible corneal opacity: reports on human health indicate eye contact will cause pain, bleeding, tears, pupil constriction and blurred vision.
Severe poisoning will affect the central nervous system, producing inco-ordination, slurred speech, loss of reflexes, weakness, fatigue, involuntary muscle contractions, twitching, tremors of the tongue or eyelids and eventually paralysis of the body extremities and the respiratory muscles. In severe cases there may also be involuntary defecation or urination, psychosis, irregular heart beat, unconsciousness, convulsions and coma. Ingestion of 120 mg monocrotophos can be fatal.
Like other OPs, monocrotophos is a potent cholinesterase inhibitor. The no effect level (NOEL) is 0.03 mg/kg in rats. It is slightly irritating to the skin and mildly irritating to the eyes(12,13).
Monocrotophos has also been shown to cause delayed neuropathy. A study in Egypt of farmers using OPs, including monocrotophos, found that 50% of the workers showed signs of neurological effects such as superficial or deep sensory loss and decrease or lost reflexes in their ankle or ankle and knee. (See Pesticides Trust OP fact sheet for more data on neurological effects.)
Monocrotophos is not carcinogenic in rats at 0.45 mg/kg/day, the highest dose tested. No significant carcinogenic lesions were observed when rats were exposed to monocrotophos aerosol at concentrations from 97-308 mg/m3 for one hour.
Researchers have generated a rat reproductive (and offspring) NOEL of 2.7 ppm, evidenced by decreased fertility, pup viability and weight, partly attributed to depressed maternal lactation.
Teratogenicity (birth defects)
Rats which received doses of 2 mg/kg per day of monocrotophos produced foetuses with lower than average length and weight and maternal toxicity in the form of reduced body weight gain in pregnancy at 1.0 mg/kg. No teratogenic effects were found at 2 mg /kg/day in rats, the highest dose tested.
Nerve growth factor(50 ng/ml) induced functional differentiation in PC12 cells has been reported. The studies have been carried out showing mitochondria mediated apoptosis in PC12 cells exposed to monocrotophos. A significant induction in reactive oxygen species, lipid peroxides, and the ratio of glutathione disulfide/reduced glutathione was observed in cells exposed to selected doses of Monocrotophos. Following the exposure of PC12 cells to MCP, the levels of protein and mRNA expression of Caspase-3, Caspase-9, Bax, p53, P21, Puma, and cytochrome-c were significantly upregulated, whereas the levels of Bcl2, Bclw, and Mcl1 were down regulated. TUNEL assay, DNA laddering, and micronuclei induction show that long-term exposure of PC12 cells to MCP at higher concentration (10-5 M) decreases the number of apoptotic events due to an increase in the number of necrotic cells. MCP-induced translocation of Bax and cytochrome-c proteins between the cytoplasm and mitochondria confirmed the role of monocrotophos in mitochondrial membrane permeability. Mitochondria mediated apoptosis induction was confirmed by the increased activity of caspase cascade. These apoptotic changes could be correlated with elevated levels of expression of selected cytochrome P450s (CYP1A1/1A2, 2B1/2B2, 2E1) in PC12 cells exposed to Monocrotophos (10−5 M).
Key health issues
Concerns about the safety of monocrotophos has led to its inclusion in the Prior Informed Consent (PIC) procedure (see page 16 for more on PIC). Governments are informed that formulations which exceed 600 g/litre of active ingredient may not be safe because of their impact on human health under conditions of use in developing countries. Governments which wish to prohibit these formulations can notify the PIC secretariat. Their decisions will be circulated to exporting countries.
Many incidents in developing countries have been linked to monocrotophos. It is often difficult to trace an incident to a particular active ingredient: frequently a 'block' of pesticides commonly used in a region may be linked to a survey indicating occupational and other health impacts in the area. Monocrotophos has been pointed to as a cause, in the following:
- Brazil, Parana State Monocrotophos caused 107 of 412 reported incidents analysed in 1990, and the toxicology centre and health clinics also noted 1,650 incidents involving monocrotophos between 1982 and 1991.
- Paraguay In a region where monocrotophos is one of the most commonly used active ingredients there have been numerous cases of pesticide poisoning; monocrotophos was identified as the cause of paralysis in children in cotton-growing areas by the Ministry of Public Health and Welfare which found that 2-3 weeks of frequent exposure caused paralysis in children and acute poisoning in adults.
- Egypt In a cotton growing region of Egypt the health of 14 farmers who spray was compared with a control group from the same region. Monocrotophos is widely used and 61% of those surveyed showed symptoms of chronic pesticide poisoning.
- Philippines, Cordillera region Monocrotophos was one of the pesticides widely used by farmers in a survey that found all farmers suffered some adverse health effects.
- Indonesia In observations of 906 spray operations of 214 farmers commonly using monocrotophos and other OPs, over a three-month period, researcher found a significant increase-from two to fiftyfold-in the symptoms of pesticide toxicity during the spraying period. Of these spray operations, 21% brought on three or more neurobehavioural and intestinal signs of poisoning.
Fate in the environment
The EU has classified monocrotophos as dangerous for the environment. Monocrotophos has a half life of 14-21 days at pH9 and 25˚C, with the rate decreasing at lower pH's and increasing at higher temperatures. Degradation on soil exposed to natural sunlight is rapid (half life less than 7 days) and on dark control samples is slower (half-life approximately 30 days). Monocrotophos is mobile in soil, and although it degrades rapidly it may possess potential for groundwater contamination.
Monocrotophos is one of the most toxic pesticides to birds and is extremely toxic other wildlife, highly toxic to bees. It is toxic to shrimps and crabs, moderately toxic for fish and non-toxic for microorganisms. The acute LD50 for birds ranges from 0.9-6.7 mg/kg body weight, and for honey bees 33-84 µg/bee.
There are numerous reports of avian mortality attributed to monocrotophos. The most recent occurred in Argentina, where an estimated 20,000 hawks died over an area of approximately 200km by 250 km in 1996. More than 700 dead hawks were found in one roost. Ornithologists suggested that monocrotophos used against grasshopper pests in the region was responsible, with hawks affected by direct exposure to the spray or secondary poisoning through eating contaminated grasshoppers. Scientists from Canada and the US had observed that smaller numbers of hawks were returning after migrating to South America. Miniature satellite transmitters attached to hawks led to the discovery. The major manufacturer, Novartis, joined meetings which agreed not to use monocrotophos in the region and encouraged other local distributors to stop selling the pesticide. A campaign to inform farmers was also supported by Novartis.
OPs do not have long persistence and are generally found at low levels in food. Monocrotophos is not used in the UK, and testing imported food in 1996 found low levels (0.03 mg/kg) in one sample of dried currants (of eight tested) imported from Greece. Testing by UK food industry sources found monocrotophos residues in dwarf beans (0.07 mg/kg). Maximum residue limits have been set in some products in the range of 0.02-1 mg/kg, and the acceptable daily take is 0.0006 mg/kg body weight.
Monocrotophos and some of its metabolites have been identified in the milk, muscle, and liver of cows and in the milk of goats following ingestion of this chemical.
Pre-harvest intervals have been set in several countries and are generally in the order of 7-15 days for vegetables and potatoes, maize and citrus and 28-30 days for other crops.
White fly resistance has caused plague-like outbreaks on cotton crops. Records over time show that resistance to monocrotophos of the Colorado potato beetle on Long Island, US, appeared more quickly than to almost any other pesticide, within one year of introduction.
Ways to reduce exposure
Full protective clothing should be worn, including a respirator when mixing and spraying tall crops. Use of flaggers should be avoided. All equipment and protective clothing should be washed thoroughly after use and clothing should be laundered separately from family clothing. Unprotected workers should be kept out of treated areas for 48 hours. Manufacture, formulation, agricultural use and disposal of monocrotophos should be carefully managed to minimize contamination of the environment.
In view of the high toxicity of monocrotophos, it should not be considered in hand-applied ULV spraying practices.
Monocrotophos is a widely used, and extremely dangerous insecticide. It has now been included in the PIC procedure, in recognition of the health problems caused by formulations with a high percentage of the active ingredient. Its low cost and many applications will present a challenge to users looking for safer alternatives, or measures which will protect health.
- Germany May not be handled by adolescents and pregnant and nursing women.
- Indonesia Monocrotophos was banned for use in rice in 1986 because of insect resistance and certain formulations phased out in 1994.
- Kuwait Severely restricted: to use on plants up to the flowering stage only.
- Malaysia Registration for use only on coconut and oil palm by trunk injection.
- Philippines In 1990 the Fertilizer and Pesticide Authority issued Circular No. 01, which included a severe restriction on monocrotophos for use only in bean fly control. A six month phase out period took effect from 29 September 1993.
- Sri Lanka Severely restricted. Import prohibited since July 1995.
- USA Voluntarily withdrawn by the registrant in 1989. Before withdrawal it could be used only by certified applicators. No remaining uses are allowed. Main concern is toxicity to non-target species, especially birds.
Cholinergics Receptor ligandsAgonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium bromide • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • PD-0298029 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium bromide • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • Anatoxin-a • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • Xenon
Reuptake inhibitorsPlasmalemmalCHT InhibitorsVAChT Inhibitors Enzyme inhibitorsChAT inhibitors1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • CatabolismAChE inhibitorsReversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil
Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)BChE inhibitorsCymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.
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