| Identification | More | [Name]
Phosmet | [CAS]
732-11-6 | [Synonyms]
CEKUMET
FOSDAN
imidan
IMIDAN (TM)
IMIDITHION
IMIDN
INOVAT
N-[MERCAPTOMETHYL]-PHTHALIMIDE-S-[O,O-DIMETHYL PHOSPHORODITHIOATE]
O,O-DIMETHYL PHTHALIMIDO-METHYL-PHOSPHOROTHIOLOTHIONATE
O,O-DIMETHYL S-PHTHALIMIDOMETHYL DITHIOPHOSPHATE
O,O-DIMETHYL-S-PHTHALIMIDO METHYL-PHOSPHORODITHIOATE
PHOSMET
Phosphorodithioic acid S-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl] O,O-dimethyl ester
Phthalimidomethyl-0，0-dimethyl phosphorodithioate
PHTHALOPHOS
PMP
PROLATE
R-1504
(O,O-Dimethyl-phthalimidiomethyl-dithiophosphate)
Decemthion | [EINECS(EC#)]
211-987-4 | [Molecular Formula]
C11H12NO4PS2 | [MDL Number]
MFCD00055501 | [Molecular Weight]
317.32 | [MOL File]
732-11-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Phosmet is a white crystalline solid | [Melting point ]
72.5°C | [Boiling point ]
412.6±47.0 °C(Predicted) | [density ]
1.03 g/cm3 | [vapor pressure ]
6.5×10-5 Pa (25°C) | [Fp ]
>100 °C | [storage temp. ]
0-6°C
| [solubility ]
Chloroform: Slightly Soluble,Methanol: Slightly Soluble | [form ]
solid | [pka]
-2.63±0.20(Predicted) | [Water Solubility ]
25 mg l-1 (25°C) | [BRN ]
264869 | [LogP]
2.780 | [CAS DataBase Reference]
732-11-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Phosmet(732-11-6) | [EPA Substance Registry System]
732-11-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn;N,N,Xn | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2811 | [WGK Germany ]
3 | [RTECS ]
TE2275000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [Safety Profile]
A human poison by
ingestion. Poison experimentally by
inhalation and ingestion routes. Moderately
toxic by skin contact. Human systemic
effects by inhalation: lachqmation,
somnolence, and olfaction effects.
Experimental teratogenic and reproductive
effects. Mutation data reported. When
heated to decomposition it emits very toxic
fumes of NOx, POx, and SOx. See also
ESTERS. | [Hazardous Substances Data]
732-11-6(Hazardous Substances Data) | [Toxicity]
LD50 in male, female rats (mg/kg): 113, 160 orally (Gaines) |
| Hazard Information | Back Directory | [General Description]
Off-white crystalline solid with an offensive odor. Used as an insecticide and acaricide. | [Reactivity Profile]
Organophosphates, such as PHOSMET, 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. Storage above 113 F, may lead to decomposition. [EPA, 1998]. | [Health Hazard]
PHOSMET is an organophosphorus pesticide. This material is very toxic; the probable oral lethal dose for humans is 50-500 mg/kg, or between 1 teaspoon and 1 oz. for a 150 lb. person. It is a cholinesterase inhibitor and has central nervous system effects. Oral lethal doses in humans have been reported at 50 mg/kg. | [Potential Exposure]
An organophosphorus insecticide and acaricide. | [Fire Hazard]
(Non-Specific--Organophosphorus Pesticide, n.o.s.). Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Storage above 113F, may lead to decomposition. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Speed in removing material from skin is of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and/or slurry of activated charcoal in water; and induce vomiting. Do not make an unconscious person vomit. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. Transport to a health care facility. | [Shipping]
UN2783 Organophosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1Poisonous materials, Technical Name Required. | [Incompatibilities]
Organothiophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrideds and active metals. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Not compatible with other pesticides under alkaline conditions. Contact with water, steam or moisture forms phthalic acids. Slightly corrosive to metals in the presence of moisture. | [Description]
Phosmet is an organophosphate insecticide and acaricide.1,2,3 It reduces apple damage by a large variety of insects, including apple maggots, codling moths, and obliquebanded leafrollers when used as either a border or cover spray at a concentration of 1.9 kg AI/hectare.2 Phosmet is effective in controlling S. scabiei in pigs when applied as a 20% pour-on solution.3 It is toxic to rats via oral administration (LC50 = 230 mg/kg).4 Formulations containing phosmet have been used in the control of insects and mites in agriculture. | [Waste Disposal]
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. 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. Small amounts may be decomposed with hypochlorite. For large amounts, incineration with effective gas scrubbing is recommended. | [Uses]
Insecticide, acaricide. | [Uses]
Nonsystemic acaricide and insecticide used on citrus, fruit, grape and potato crop | [Uses]
Phosmet is used as a pesticide to protect crops and vegetation. Insecticide. | [Uses]
Phosmet is used to control a wide range of insects and mites in
fruit, potatoes, sweet potatoes, vines, cotton and many other crops. It is
also used as a veterinary ectoparasiticide. | [Definition]
ChEBI: Phosmet is an organic thiophosphate, an organothiophosphate insecticide and a member of phthalimides. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is functionally related to a N-(hydroxymethyl)phthalimide. | [Agricultural Uses]
Insecticide, Acaricide: Phosmet is a non-systemic insecticide used on both
plants and animals. It is mainly used on apple trees for
control of coddling moth, though it is also used on a wide
range of crops including alfalfa, nuts, grapes, blueberries,
peas, potatoes, fruit crops, ornamentals, and vines for the
control of aphids, suckers, mites, fire ants and fruit flies.
The compound is also an active ingredient in some dog
collars. It is used as an insecticide on swine and cattle.
U.S. Maximum Allowable Residue Levels for Phosmet
[40 CFR 180.261 (a)]: Alfalfa 40 ppm; almond, hulls
10 ppm; apple 10 ppm; apricot 5 ppm; blueberry 10 ppm;
cattle, fat 0.2 ppm; cattle, meat 0.2 ppm; cattle, meat byproducts
0.2 ppm; cherry 10 ppm; cotton, undelinted
seed 0.1 ppm; crabapple 20 ppm; cranberry 10 ppm; fruit,
stone, group 12 5 ppm; goat, fat 0.2 ppm; goat, meat0.2 ppm; goat, meat byproducts 0.2 ppm; grape 10 ppm;
hog, fat 0.2 ppm; hog, meat 0.2 ppm; hog, meat byproducts
0.2 ppm; horse, fat 0.2 ppm; horse, meat 0.2 ppm; horse,
meat byproducts 0.2 ppm; kiwifruit 25 ppm; nectarine
5 ppm; nuts 0.1 ppm; pea 0.5 ppm; pea, field, hay 10 ppm;
pea, field, vines 10 ppm; peach 10 ppm; pear 10 ppm; pistachio
0.1 ppm; plum, prune, fresh 5 ppm; potato 0.1 ppm;
sheep, fat 0.2 ppm; sheep, meat 0.2 ppm; sheep, meat byproducts
0.2 ppm; sweet potato, roots 10 ppm. Regional
registration, as defined in section 180.1(n) [40 CFR
180.261 (c)]: Crabapple 20 ppm; pistachio 0.1 ppm. | [Trade name]
Trade Names: APPA®; DECEMTHION®; DELPHOS
®; FESDAN®; FIREBAN®; FTALOPHOS®;
IMIDAN®; KEMOLATE®; PERCOLATE®; PMC®;
PROLATE®[C]; R 1504®; SAFIDON®; SMIDAN®;
STARBAR CATTLE DUST®[C]; STAUFFER R 1504®;
VET-KEM®; ZEOCON® | [Carcinogenicity]
No treatment-related increases
in tumor incidence occurred in rats given a diet with 0, 20, 40,200, or 400 ppm (400 ppm terminated at 12 months) (equivalent
to 0, 1.1, 1.8, 9.4, and 23 mg/kg/day in males and 0, 1.1,
2.1, 10.9, and 27 mg/kg/day in females) for 2 years .
When mice were given diets with 0, 5, 25, or 100 ppm
phosmet (approximately 0.75, 3.75, or 15.0 mg/kg/day) for
2 years, there was an increased incidence of hepatocellular
tumors in males and mammary gland tumors in
females . | [Environmental Fate]
Soil. In soils, phosmet is rapidly hydrolyzed to phthalimide (Camazano and Martin,
1980; Sánchez Camazano and Sánchez Martin, 1983). The rate of hydrolysis is greater in
the presence of various montmorillonite clays and chloride salts. The calculated hydrolysis
half-lives of phosmet in the presence of calcium, barium, copper, magnesium and nickel
montmorillonite clays were 0.084, 0.665, 10.025, 16.926 and 28.738 days, respectively.
Similarly, the half-lives of phosmet in the presence of copper, calcium, magnesium and
barium chlorides were <0.020, 5.731, 10.680 and 12.242 days, respectively. In comparison,
the hydrolysis of phosmet in a neutral water solution was 46.210 days (Sánchez Camazano
and Sánchez Martin, 1983)
Plant. In plants, phosmet is degraded to nontoxic compounds (Hartley and Kidd, 1987).
Dorough et al. (1966) reported the half-life in Bermuda grass was 6.5 days. Half-life values
ranged from 1.2 to 6.5 days (Dorough et al., 1966; Leuck and Bowman
Chemical/Physical. Emits toxic fumes of phosphorus, nitrogen and sulfur oxides when
heated to decomposition (Sax and Lewis, 1987). Though no products were identified, the
hydrolysis half-lives at 20°C were 7.0 days and 7.1 hours at pH 6.1 and pH 7.4, respectively.
At 37.5°C and pH 7.4, the hydrolysis is 1.1 hours (Freed et al., 1979) | [Metabolic pathway]
The main degradative route of phosmet metabolism in plants and animals
is similar with the compound being hydrolysed via attack on the carbonyl
group of the phthaloyl moiety, yielding phthalamic acid which is further
hydrolysed and decarboxylated to benzoic acid. It should be noted,
however, that the studies on which the evidence for these metabolites
is based are old and used paper chromatography for the main
analytical evidence. A rather later study in rats identified N-hydroxymethylphthalimide
and phthalimide as metabolites, implying a degradative
hydrolytic route via attack on the N-methylene carbon atom.
Oxidative desulfuration to the active acetylcholinesterase inhibitor
phosmet oxon predominates over hydrolysis in insects and is responsible
for the selectivity of the compound. | [Metabolism]
Orally administered
phosmet in mammals is rapidly degraded to
phthalamic acid, phthalic acid, and phthalic acid derivatives,
and the metabolites are excreted in the urine.
Oxidative desulfuration to the oxon predominates over
hydrolysis in insects. It is rapidly degraded in plants
and soils. | [Degradation]
Phosmet is relatively stable in acid media but it is hydrolysed under basic
conditions. The half-lives at pH values 4.5, 7 and 8.3 were 13 days, <12
hours and <4 hours, respectively (PM). Phosmet was hydrolysed under
basic conditions to phthalamic acid (2), phthalic acid (3) and O,Odimethyl
phosphorodithioate (4) indicating that nucleophic attack by
OH-occurs preferentially on the phthalimido carbonyl group rather than
on phosphorus (Menn et al., 1965) (Scheme 1). The photolysis of an ether
solution of phosmet irradiated in a quartz tube by unfiltered UV light
from a mercury vapour lamp was investigated by Tanabe ef al. (1974).
Photoproducts were separated by silica gel column chromatography and
characterised by GLC, TLC, MS and 1H NMR spectroscopy in comparison
with authenticated reference standards. Two major photoproducts were
identified as N-methylphthalimide (5) and N-methoxymethylphthalimide
(6) (Scheme 1) in addition to a large number of minor products which
were not characterised. The use of a Pyrex filter to remove light below
286 nm reduced the rate of photolysis but not the nature of the products.
N-Methoxymethylphthalimide (6) was the main product when phosmet
was irradiated by sunlight in thin films on silica gel TLC plates or in dilute
aqueous solution [personal communication by McBain and Menn (1973),
in Tanabe et al., 1974]. | [Toxicity evaluation]
The acute oral LD50 for rats is 113–160 mg/kg. Inhalation LC50
(1 h) for rats is 2.76 mg/L air. NOEL (2 yr) for rats
is 40 mg/kg/d. ADI is 0.01 mg/kg bw. |
| Questions And Answer | Back Directory | [Chemical Properties]
Phosmet is an off-white crystalline solid with an offensive odour.It is very soluble in acetone, xylene, methanol, benzene, toluene, and methyl isobutyl ketone; in kerosene. Phosmet is combustible and susceptible in the presence of strong reducing agents and hydrides. It forms highly toxic and flammable phosphine gas. On partial oxidation by oxidising agents, phosmet releases toxic phosphorus oxides. On heating and/or burning, phosmet decomposes and produces toxic fumes including nitrogen oxides, phosphorous oxides, and sulphur oxides.
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