MEVINPHOS

MEVINPHOS Basic information
Product Name:MEVINPHOS
Synonyms:Methyl 3-(dimethoxyphosphinyloxy)crotonate;Methyl-3-(dimethoxyphosphinato)-2-butenoate;methyl3-(dimethoxyphosphinyloxy)crotonate;Methyl3-[(dimethoxyphosphinyl)oxy]-2-bu-tenoate;methyl3-hydroxy-alpha-crotonatedimethylphosphate;Mevinfos;Mevinox;Mevinphos (alpha+beta)
CAS:7786-34-7
MF:C7H13O6P
MW:224.15
EINECS:232-095-1
Product Categories:
Mol File:7786-34-7.mol
MEVINPHOS Structure
MEVINPHOS Chemical Properties
Melting point 13.95℃
Boiling point 115-117℃ (2 Torr)
density 1.25 g/cm3 (20℃)
vapor pressure 2.2 x 10-3 mmHg at 20 °C, 5.7 at 29 °C (Freed et al., 1977)
refractive index 1.4494 (589.3 nm 20℃)
Fp -18 °C
storage temp. APPROX 4°C
solubility Miscible with acetone, benzene, chloroform, ethanol, ketones, toluene, and xylene. Soluble in carbon disulfide and kerosene (50 g/L) (Windholz et al., 1983; Worthing and Hance, 1991).
form liquid (rough estimate)
color Colorless to pale yellow liquid with a weak odor
Water Solubility Miscible (Gunther et al., 1968)
Exposure limitsNIOSH REL: TWA 0.01 ppm, STEL 0.03 ppm, IDLH 4 ppm; OSHA PEL: 0.1 mg/m3; ACGIH TWA: TLV 0.01 ppm, STEL 0.03 ppm.
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
EPA Substance Registry SystemMevinphos (7786-34-7)
Safety Information
Hazard Codes T+,N,Xn,F
Risk Statements 27/28-50/53-67-65-38-11-20
Safety Statements 23-28-36/37-45-60-61-62
RIDADR 3018
RTECS GQ5250000
HazardClass 6.1(a)
PackingGroup I
HS Code 29199000
Hazardous Substances Data7786-34-7(Hazardous Substances Data)
ToxicityLD50 in female, male rats (mg/kg): 3.7, 6.1 orally; 4.2, 4.7 dermally (Gaines)
IDLA4 ppm
MSDS Information
MEVINPHOS Usage And Synthesis
DescriptionPure mevinphos is a colourless liquid, while technical grade mevinphos is a pale yellow liquid with a very mild odour. It is soluble in water but very soluble in alcohols, ketones, chlorinated hydrocarbons, aromatic hydrocarbons, and many organic solvents. It is both an insecticide and acaricide. The U.S. EPA grouped mevinphos as an RUP, and hence it should be purchased and used only by certified and trained pesticide applicators. It is not registered for use in many countries including the United States. Mevinphos is used to control a broad spectrum of insects, including aphids, grasshoppers, leaf-hoppers, cutworms, caterpillars, and many other insects on a wide range of field, forage, vegetable, and fruit crops. It is also an acaricide that kills or controls mites and ticks. It acts quickly both as a contact insecticide, acting through direct contact with target pests, and as a systemic insecticide, which becomes absorbed by plants on which insects feed.
Chemical PropertiesMevinphos is a pale yellow to orange highboiling liquid. Weak odor. The carrier solvent may change the physical properties listed here.
Chemical PropertiesPhosdrin is a stable, colourless, spontaneously flammable pyrophoric liquid with weak odour. It is combustible and incompatible with strong oxidising agents, corrosive to cast iron, some stainless steels, and brass.
UsesMevinphos is a pesticide used in the protection of crops. Insecticide.
UsesInsecticide and acaricide.
UsesContact insecticide and acaricide for control of chewing insects and spider mites in fruits, vegetables and ornamentals.
DefinitionChEBI: Mevinphos is a dialkyl phosphate and an organophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide, an agrochemical and an avicide. It is functionally related to a methyl 3-hydroxybut-2-enoate.
General DescriptionPale yellow to orange liquid, with a weak odor. Used as an insecticide and acaricide on vegetables, alfalfa, deciduous fruits and nuts.
Air & Water ReactionsHydrolyzes rapidly as MEVINPHOS dissolves in water.
Reactivity ProfileOrganophosphates, such as MEVINPHOS, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
HazardToxic by ingestion, inhalation, and skinabsorption; use may be restricted; cholinesteraseinhibitor. Questionable carcinogen.
Health HazardMEVINPHOS is super toxic; the probable oral lethal dose for humans is less than 5 mg/kg, or a taste (less than 7 drops) for a 150-lb. person. It has direct and immediate effects whether it is swallowed, inhaled, or absorbed through the skin.
Health HazardA severely acute toxicant by all routes;cholinesterase inhibitor; absorbed throughthe skin, lungs, and mucous membranes;more toxic by subcutaneous or intravenousroutes than by an intraperitoneal route; toxicsymptoms include headache, weakness,blurred vision, diarrhea, and tightness inthe chest; signs of severe poisoning aresweating, salivation, lacrimation, constrictionof the pupils, depression, tremor, and convulsions; oral LD50 value (mice): 4 mg/kg;skin LD50 value (mice): 12 mg/kg; exposure limit: TLV-TWA 0.01 (~0.1 mg/m3)(ACGIH, MSHA, and OSHA).
Fire HazardFire may produce irritating or poisonous gases. Runoff from fire control may give off poisonous gases and also cause pollution. When heated to decomposition, MEVINPHOS emits toxic fumes of phosphorus oxides. Avoid strong oxidizers. Avoid temperatures above 77-86F, sources of heat, fire, free flames or spark-generating equipment.
Agricultural UsesInsecticide, Acaricide: Mevinphos is an organophosphate insecticide used to control a broad spectrum of insects, including aphids, grasshoppers, leafhoppers, cutworms, caterpillars, and many other insects on a wide range of field, forage, vegetable, and fruit crops. It is also an acaricide that kills or controls mites and ticks. It acts quickly both as a contact insecticide, acting through direct contact with target pests, and as a systemic insecticide which becomes absorbed by plants on which insects feed. Not approved for use in EU countries. Not registered for use in the U.S.
Trade nameAI3-22374®; APAVINPHOS®; CASWELL No. 160B®; CENTURY-CIDE®[C]; COMPOUND 2046®; DURHAM®[C]; EXCELCIDE®[C]; GESFID®; GESTID®; PD 5®; HELENA PHOSDRIN®[C]
Contact allergensSensitization to mevinphos (also named Duraphos, Phosdrin, and Phosfene), an organophosphate cholinesterase inhibitor that is used as an insecticide, was rarely reported.
Safety ProfilePoison by ingestion, inhalation, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: peripheral motor nerve recording changes. An insecticide. When heated to decomposition it emits toxic fumes of POx.
Potential ExposureThose engaged in the manufacture, formulation, and application of this super toxic contact and systemic insecticide and acaricide.
Environmental FatePlant. In plants, mevinphos is hydrolyzed to phosphoric acid dimethyl ester, phosphoric acid and other less toxic compounds (Hartley and Kidd, 1987). In one day, the compound is almost completely degraded in plants (Cremlyn, 1991). Casida et al. (1956) proposed two degradative pathways of mevinphos in bean plants and cabbage. In the first degradative pathway, cleavage of the vinyl phosphate bond affords methylacetoacetate and acetoacetic acid which may be precursors to the formation of the end products dimethyl phosphoric acid, methanol, acetone and carbon dioxide. In the other degradative pathway, direct hydrolysis of the carboxylic ester would yield vinyl phosphates as intermediates. The halflife of mevinphos in bean plants was 12 hours (Casida et al., 1956). In alfalfa, the halflife was 17 hours (Huddelston and Gyrisco, 1961).
Chemical/Physical. The reported hydrolysis half-lives of cis-mevinphos and transmevinphos at pH 11.6 are 1.8 and 3.0 hours, respectively (Casida et al., 1956). The volatility half-lives for the cis and trans forms at 28°C were 21 and 24 hours, respectively (Casida et al., 1956). Worthing and Hance (1991) reported that at pH values of 6, 7, 9 and 11, the hydrolysis half-lives were 120 days, 35 days, 3.0 days and 1.4 hours, respectively (Worthing and Hance, 1991).
Emits toxic phosphorus oxide fumes when heated to decomposition (Lewis, 1990).
ShippingUN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2783 Organophosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material.
Toxicity evaluationAcute oral LD50 for rats is 3–12 mg/kg.Inhalation LC50 (1 h) for rats is 0.125 mg/L air. No ill effects were observed in rats receiving 4 mg/kg diet (0.2 mg/kg/d) for 2 yr. ADI is 1.5 μg/kg b.w. In comparison with the Z-isomer, E-mevinphos is a more effective insecticide and is detoxified more quickly in plants but more slowly in animals.
IncompatibilitiesDecomposes in heat (below boiling point @ 300℃) producing phosphoric acid and phosphorous oxides fumes. Strong oxidizers may cause release of toxic phosphorus oxides. Organophosphates, in the presence of strong reducing agents such as hydrides, may form highly toxic and flammable phosphine gas. Keep away from alkaline materials. Corrosive to cast iron, some stainless steels and brass. Attacks some forms of plastics, rubber and coatings.
Waste DisposalMevinphos is 50% hydrolyzed in aqueous solutions at an unspecified temperature in 1.4 hours at pH 11, 35 days at pH 7; and 120 days at pH 6. Thermal decomposition is rapidly accomplished by lime sulfur. Mevinphos may also incinerated. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
MEVINPHOS Preparation Products And Raw materials
Raw materialsSulfuryl chloride-->Methyl acetoacetate-->Trimethyl phosphite-->CREAM-->Methyl 2-chloroacetoacetate
alpha-mevinpho CIS-MEVINPHOS SOLUTION 100UG/ML IN ACETONITRILE 1ML DIMETHYLPHOSPHINIC ACID CIS-MEVINPHOS SOLUTION 100UG/ML IN MTBE 1ML DIMETHYL PHOSPHATE MEVINPHOS SOLUTION 100 NG/MYL IN TRANS-MEVINPHOS PESTANAL 50 MG,beta-mevinpho GOLD MEVINPHOS

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