Mevinphos

HCID 9560CAS 298-01-1

Grundinformationen

Standard-SMILES
COC(=O)C=C(C)OP(=O)(OC)OC
InChIKey
GEPDYQSQVLXLEU-UHFFFAOYSA-N
Summenformel
C7H13O6P
Durchschnittliche Molmasse
224,15 g/mol
Monoisotopische Masse
224,04497477

Überblick

Mevinphos is a pale yellow to orange liquid, with a weak odor. Used as an insecticide and acaricide on vegetables, alfalfa, deciduous fruits and nuts. (EPA, 1998) May be found in the form of a dry mixture where the liquid is absorbed onto a dry carrier.

Namen und Bezeichner

Bevorzugter Name
Mevinphos
IUPAC
methyl 3-dimethoxyphosphoryloxybut-2-enoate

Namen und Synonyme

7786-34-7DTXSID2032683MeniteDuraphosPD 5 (pesticide)ApavinphosGestidFosdrine14ZYO4IKXTMethyl 3-(dimethoxyphosphinoyloxy)but-2-enoateDimethyl 2-methoxycarbonyl-1-methylvinyl phosphateMethyl 3-hydroxy-alpha-crotonate dimethyl phosphate
Weitere Namen anzeigen
O,O-Dimethyl 1-carbomethoxy-1-propen-2-yl phosphateCHEBI:387253-((Dimethoxyphosphinyl)oxy)-2-butenoic acid methyl esterDTXCID40809716O,O-Dimethyl-O-2-methoxycarbonyl-1-methyl-vinyl-phosphatCrotonic acid, 3-hydroxy-, methyl ester, dimethyl phosphateNSC-46470Phosphoric acid, dimethyl ester, ester with methyl 3-hydroxycrotonate

Datenbank-Bezeichner

CAS
298-01-1、7786-34-7
PubChem CID
9560
DTXSID
DTXSID2032683
EC Number
206-051-7、232-095-1

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
71,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
6
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesBoiling point
Pesticides · 3 Einträge

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

LogP · 3 Einträge

log Kow = 0.13

1.2

0.55

Odor · 2 Einträge

Weak odor

Weak odor.

Density · 5 Einträge

1.25 at 68 °F (EPA, 1998) - Denser than water; will sink

1.25 @ 20 °C/4 °C

Relative density (water = 1): 1.25

0.0029 mmHg at 70 °F

1.25

Color/Form · 2 Einträge

PALE YELLOW LIQUID

Pale-yellow to orange liquid.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H300+H310 (81.2%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Hazard Traits - Environmental tox

Regulation (EC) No 1107/2009 (amended)

Mevinphos is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 2-Butenoic acid, 3-[(dimethoxyphosphinyl)oxy]-, methyl ester: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

Fire may produce irritating or poisonous gases. Runoff from fire control may give off poisonous gases and also cause pollution. When heated to decomposition, it emits toxic fumes of phosphorus oxides. Avoid strong oxidizers. Avoid temperatures above 77-86F, sources of heat, fire, free flames or spark-generating equipment. (EPA, 1998)

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 1 Eintrag

This material 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. (EPA, 1998)

Hazards Summary · 1 Eintrag

It is applied 1-10 days before harvest; it dissipates quickly. [HSDB] Skin sensitization occurs rarely. [Kanerva, p. 1817] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Isolate hazard area, stay upwind; ventilate closed spaces before entering, wear protective clothing and positive breathing apparatus. Remove and isolate contaminated clothing.

Use powder, water spray, foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Wear protective gloves when administering first aid. Refer immediately for medical attention.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

First Aid · 2 Einträge

Warning: Effects may be delayed. Caution is advised. Vital signs should be monitored closely.

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs and strong oxidants. Keep in a well-ventilated room. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection · 2 Einträge

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

0.09 [mg/m3]

Fire Fighting Procedures · 2 Einträge

If material is on fire or involved in a fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities ofwater. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. keep run-off water out of sewers and water sources.

Extinguishant: Alcohol foam, dry chemical, or carbon dioxide.

Toxikologische Informationen

Treatment · 1 Eintrag

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 2 Einträge

PHOSDRIN OR TRICHLORPHON AT CONCN OF 20 & 100 UG/ML OF CULTURE FLUID HAVE ACTIVITY SIMILAR TO DICHLORVOS, IN THAT THEY LOWERED THE LEVEL OF AFLATOXIN PRODUCED BY ASPERGILLUS FLAVUS & CAUSED FORMATION OF SEVERAL ANTHRAQUINONE PIGMENTS.

Treatment of rats with chlorpromazine (CPZ) did not modify cholinesterase activity in brain, skeletal muscle, myocardium, lung, liver, and kidney. CPZ slightly potentiated the effects of mevinphos.

Target OrgansEyes, skin, respiratory system, central nervous system, cardiovascular system, blood cholinesterase
Health Effects · 1 Eintrag

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Ecotoxicity Values · 5 Einträge

LD50 ANAS PLATYRHYNCHOS (MALLARD) ORAL 4.63 MG/KG (95% CONFIDENCE LIMIT 3.57-6.00 MG/KG), 5-7 MO OLD FEMALES

LD50 PHASIANUS COLCHICUS (PHEASANT) ORAL 1.37 MG/KG (95% CONFIDENCE LIMIT 0.951-1.98 MG/KG), 3-4 MO OLD MALES

LD50 TYMPANUCHUS PHASIANELLUS (SHARP TAILED GROUSE) ORAL 1.34 MG/KG (95% CONFIDENCE LIMIT 0.695-2.57 MG/KG), ADULT MALES

LC50 SALMO GAIRDNERI 0.00006 ML/L/48 HR

For more Ecotoxicity Values (Complete) data for MEVINPHOS (25 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: If released in soil, mevinphos may leach, especially in sand soils. As the clay content of the soil increases, adsorption may increase, especially when the organic content of the soil is not low. According to the Pesticides Property Database and another investigator, the field half-life of mevinphos is 3 days(2,3). In experiments in which mevinphos (10, 100, and 1000 ppm) was applied to a silty clay soil (0.5% OC, pH 5.5) and a sandy clay soil (0.6% OC, pH 6.9) at field capacity moisture and incubated at room temperature, the rate of decay was essentially first order with average rate constants of 0.0526/day in the acid soil and 0.05503/day in the neutral soil. The half-life of mevinphos was 13 days in both soils at all concn levels(1). No mevinphos was detectible in a calcareous-argillaceous (1.48% organic matter, pH 8.0) soil 8 days after application(5). In lab experiments performed with five Sacramento Delta soils, mevinphos disappeared from clay and muck soils within 48 hr and in peat soil within 10 hr(4). In peat/sand soil and sand, 16 and 12% of the initial residues remained at the end of the experiment (144 hr). In all cases, degradation was initially greater in the natural soils than autoclaved soils.

AQUATIC FATE: If released in water, mevinphos would slowly hydrolyze, especially in alkaline waters. At ambient temperatures, its half-lives are 120, 35, and 3 days at pH 6, 7, and 9, respectively(1). It would not be expected to volatilize or adsorb to sediment(SRC). The rate of loss of mevinphos in a model evaporation pond, pH 8.2 at 22 degC, was determined to be 0.0016/hr (half-life 18 days) by daily sampling over a seven day period(2). EPA's EXAMs model predicts that after 42 days, when 97% of the pesticide has been dissipated, 99.7% of the loss would be due to hydrolysis and 0.1% to volatilization(2).

ATMOSPHERIC FATE: If mevinphos is released into the atmosphere as an aerosol during spraying, it will be removed by gravitational settling. Vapor-phase mevinphos will react with photochemically-produced hydroxyl radicals resulting in an estimated atmospheric half-life of 4.5 hr(1). At night or when pollution levels are high, reaction with ozone will also contribute to mevinphos' degradation in air.

Regulatorische Informationen

FIFRA RequirementsClassified for restricted use, limited to use by or under the direct supervision of a certified applicator. ... All emulsifiable concentrates and liquid concentrates. Psycodid filter fly formulations, and 2% dusts.
CERCLA Reportable Quantities · 2 Einträge

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4(section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Mevinphos is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Clean Water Act RequirementsDesignated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance.
State Drinking Water Guidelines(FL) FLORIDA 1.8 ug/l

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

ELECTRORETINOGRAPHIC RESULTS INDICATE THAT MEVINPHOS PERTURBS RETINAL FUNCTIONING OF WHITE MOUSE BY ACTING (1) DIRECTLY ON THE PHOTORECEPTORS; (2) BY SYNAPTOLYTIC EFFECT DUE TO INHIBITION OF CHOLINESTERASES; (3) BY DAMAGE OF THE BIPOLAR &/OR THE GANGLION NEURONS.

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase. ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/

The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/

Metabolism/Metabolites · 6 Einträge

IN PRESENCE OF MOUSE LIVER ENZYMES & GLUTATHIONE, CIS-PHOSDRIN WAS DEGRADED TO CIS-DESMETHYL PHOSDRIN & S-METHYLGLUTATHIONE. WHEN TRANS-ISOMER WAS TESTED, DIMETHYLPHOSPHATE WAS OBTAINED.

/PHOSDRIN/ ... WAS DECOMP IN PLANTS BY ... ENZYMATIC HYDROLYSIS OF CARBOXYLIC ESTER TO FORM CORRESPONDING FREE ACID, ... FOLLOWED BY CLEAVAGE OF VINYL PHOSPHATE BOND & DECARBOXYLATION. FINDING OF DESMETHYL PHOSDRIN ACID IN SOME STUDIES INDICATED ... AT LEAST TWO PATHS FOR DEGRADATION OF PHOSDRIN IN PLANTS.

Mouse liver homogenates degraded trans-phosdrin at a faster rate than cis-phosdrin. Most of the degrading activity was found in the supernatant fraction. After loss of most of the activity by dialysis, addition of reduced glutathione restored the activity fully. A product of glutathione reaction with trans-phosdrin was identified as methyl glutathione. Dimethyl phosphate was also observed.

WHEN LABELED PHOSDRIN WAS FED TO COWS ... ALL RADIOACTIVITY IN FECES WAS PRESENT AS HYDROLYSIS PRODUCTS. DIMETHYL PHOSPHORIC ACID WAS IDENTIFIED IN URINE FROM A COW TREATED WITH PHOSDRIN & IN HUMAN PLASMA INCUBATED WITH PHOSDRIN.

For more Metabolism/Metabolites (Complete) data for MEVINPHOS (7 total), please visit the HSDB record page.

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

MeSH Pharmacological Classification · 2 Einträge

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

Absorption, Distribution and Excretion · 5 Einträge

WHEN LABELED PHOSDRIN WAS FED TO COWS, BLOOD LEVELS OF PHOSDRIN METABOLITES REACHED A PEAK BETWEEN 2 & 4 HR AFTER ADMIN & BLOOD WAS ESSENTIALLY FREE ... WITHIN 24 HR. WITHIN 3 DAYS, 77% OF ADMIN DOSE WAS EXCRETED. HALF THIS WAS EXCRETED VIA URINE WITHIN 12 HR.

The concn of mevinphos found in samples taken at autopsy from a man who had died within 45 minutes after drinking the compound were: stomach wall, 3,400 ppm; blood, 360 ppm; liver, 240 ppm; brain, 3 ppm; skeletal muscle, 86 ppm; kidney, 20 ppm; and urine 8 ppm. Inhibition of blood cholinesterase was essentially complete.

In cases of moderate poisoning associated with occupational exposure to mevinphos, the concentration of dimethylphosphate ... in urine samples collected during the first 12 hours after onset was 0.4 ppm. The concentration declined rapidly until about 36 hours after onset, and excretion was essentially complete within about the first 50 hours.

Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/

For more Absorption, Distribution and Excretion (Complete) data for MEVINPHOS (10 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 5 Einträge

Used to kill insects on vegetables, alfalfa, fruits, and nuts; [HSDB]

Farming (Pesticides) [Category: Industry]

CONTROLS APHIDS, MITES, GRASSHOPPERS, CUTWORMS, LEAFHOPPERS, CATERPILLARS, & MANY OTHER INSECTS ON BROAD RANGE OF FIELD, FORAGE, VEGETABLE & FRUIT CROPS. DISSIPATES QUICKLY; APPLICATION BEFORE HARVEST INTERVAL 1-10 DAYS, DEPENDING ON CROP & DOSAGE.

It is a contact and systemic acaricide and insecticide with short residual activity. It is effective against beetles and mites at 200- 300 g/ha, caterpillars at 250-500 g/ha, sap-feeding insects at 125-250 g/ha.

This is a man-made compound that is used as a pesticide.

U.S. Exports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Imports · 2 Einträge

(1972) No Data

(1974) 1.78X10+7 GRAMS (PRINCPL CUSTMS DISTS)

Consumption Patterns · 4 Einträge

ABOUT 60% USED ON VEGETABLES; THE BALANCE ON ALFALFA & DECIDUOUS FRUITS & NUTS (1974)

Lettuce, 30.4%; All vegetables, 73%; Cereals, 1.3%; Fruits, 4.7%; Non-cereal forage and feed crops, 20.8% (1984) /California use, calculated from table/

(1974) 3.6X10+8 GRAMS (CONSUMPTION)

(1984) 1.06X10+8 g /Used in California/

Methods of ManufacturingREACTION OF TRIMETHYL PHOSPHITE WITH METHYL 2-CHLORO-3-OXYBUTYRATE
Formulations/Preparations · 5 Einträge

EMULSIFIABLE CONCENTRATES (EC) (100 OR 240 G/L), SOLUBLE LIQUID (100 OR 240 G/L)

APAVINPHOS

CIS-PHOSDRIN

CMDP

For more Formulations/Preparations (Complete) data for MEVINPHOS (12 total), please visit the HSDB record page.

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