| | 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 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 limits | NIOSH 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 System | Mevinphos (7786-34-7) |
| | MEVINPHOS Usage And Synthesis |
| Description | Pure 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 Properties | Mevinphos is a pale yellow to orange highboiling
liquid. Weak odor. The carrier solvent may change
the physical properties listed here. | | Chemical Properties | Phosdrin 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.
| | Uses | Mevinphos is a pesticide used in the protection of crops. Insecticide. | | Uses | Insecticide and acaricide. | | Uses | Contact insecticide and acaricide for control of chewing insects and spider mites in
fruits, vegetables and ornamentals. | | Definition | ChEBI: 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 Description | Pale yellow to orange liquid, with a weak odor. Used as an insecticide and acaricide on vegetables, alfalfa, deciduous fruits and nuts. | | Air & Water Reactions | Hydrolyzes rapidly as MEVINPHOS dissolves in water. | | Reactivity Profile | Organophosphates, 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. | | Hazard | Toxic by ingestion, inhalation, and skinabsorption; use may be restricted; cholinesteraseinhibitor. Questionable carcinogen. | | Health Hazard | MEVINPHOS 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 Hazard | A 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 Hazard | Fire 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 Uses | Insecticide, 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 name | AI3-22374®; APAVINPHOS®; CASWELL
No. 160B®; CENTURY-CIDE®[C]; COMPOUND
2046®; DURHAM®[C]; EXCELCIDE®[C]; GESFID®;
GESTID®; PD 5®; HELENA PHOSDRIN®[C] | | Contact allergens | Sensitization to mevinphos (also named Duraphos,
Phosdrin, and Phosfene), an organophosphate cholinesterase
inhibitor that is used as an insecticide, was
rarely reported. | | Safety Profile | Poison 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 Exposure | Those engaged in the manufacture,
formulation, and application of this super toxic contact and
systemic insecticide and acaricide. | | Environmental Fate | Plant. 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). | | Shipping | UN3018 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 evaluation | Acute 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. | | Incompatibilities | Decomposes 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 Disposal | Mevinphos 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 |
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