| Identification | Back Directory | [Name]
Orthene | [CAS]
30560-19-1 | [Synonyms]
75sp
75 SP
Ortril
ORTRAN
kitron
LANCER
ASATAF
ACEVOL
Ortean
Orthen
re12420
ORTHENE
Oxthene
Acephat
ent27822
AIMTHENE
ACEPHATE
RE 12420
LUCID(R)
Aceprate
ENT 27822
ORTHENE(R)
CEKUCEFATE
RACETACIFAT
ORTHENE(TM)
ortho 12420
ortho124120
Orthene-755
ORTHO 124120
acetamidophos
Acephate E.C.
chevronorthene
chevronre12,420
Chevron re 12,420
ACEPHATETECHNICAL
ACEPHATE SOLUTION
ACEPHATE, 1GM, NEAT
ACEPHATE, 250MG, NEAT
Acephate soluble powder
Acephate Solution, 100ppm
Acephate 250mg [30560-19-1]
acephate (bsi,iso,ansi,esa,jmaf)
Acephate ,orthene,Ortran,Tornado
o,S-Dimethyl acetylamidothiophosphate
O，S-Dimethylacetylphosphoroamidothioate
O,S-DIMETHYL ACETYLPHOSPHOR-AMIDOTHIOATE
ACEPHATE PESTANAL (O,S-DIMETHYL ACETYLPH
O,S-Dimethyl-N-acetylphosphoraminothionate
O,S-DimethylL n-Acetylphosphoramidothioate
O,S-DIMETHYL N-ACETYL-PHOSPHORAMIDOTHIOATE
N-(Methoxy(methylthio)phosphinoyl)acetamide
Acetylphosphoramidothioic acid O,S-dimethyl
O，S-dimethyl-N-acethyl phosphoramidothioate
N-(Methoxy-methylsulfanylphosphoryl)acetamide
acetylphosphoramidothioicacido,s-dimethylester
Acetylphosphoramidothioic acid O,S-dimethyl ester
Phosphoramidothioicacid,acetyl-,O,S-dimethylester
Acetylaminothiophosphonic acid O,S-dimethyl ester
phosphoramidothioicacid,n-acetyl-,o,s-dimethylester
N-Acetyl-phosphoramidothioic acid O,S-dimethyl ester
Phosphoramidothioic acid, acetyl-, O,S-dimethyl ester
acephate (ISO) O S-dimethyl acetylphosphoramidothioate
ACEPHATE SOLUTION 100 NG/MYL IN ACETONIT RILE, PESTANAL
Phosphoramidothioic acid, N-acetyl-, O,S-dimethyl ester | [EINECS(EC#)]
250-241-2 | [Molecular Formula]
C4H10NO3PS | [MDL Number]
MFCD00055361 | [MOL File]
30560-19-1.mol | [Molecular Weight]
183.17 |
| Chemical Properties | Back Directory | [Description]
Acephate is an organophosphate foliar spray insecticide of moderate persistence with residual
systemic activity. It is a contact and systemic insecticide and very effective against a large
number of crop pests such as alfalfa looper, aphids, armyworms, bagworms, bean leaf beetle,
bean leafroller, black grass bugs, bollworm, budworm, and cabbage looper. Acephate is a
colourless to white solid organophosphate insecticide. Exposures to acephate cause poisoning
to animals and humans. Acephate inhibits acetylcholine esterase (AchE), the essential nervous
system enzyme, and causes characteristic organophosphate poisoning. The symptoms
of toxicity include, but are not limited to, headache, nervousness, blurred vision, weakness,
nausea, fatigue, stomach cramps, diarrhoea, difficulty in breathing, chest pain, sweating,
pinpoint pupils, tearing, salivation, clear nasal discharge and sputum, vomiting, muscle
twitching, muscle weakness, and, in severe poisoning, convulsions, respiratory depression,
coma, and death. Acephate causes cholinesterase inhibition leading to overstimulation,
respiratory paralysis, and death. The U.S. EPA classified acephate as Group C, meaning a
possible human carcinogen, and therefore requires judicious handling and management. | [Appearance]
Colorless crystalline solid (80% or more pure) or white powder (technical). Has an odor of rotten cabbage or mercaptans (like sulfur). | [Melting point ]
93°C | [density ]
1.35 | [vapor pressure ]
2.26 x 10-4 Pa (24 °C) | [Fp ]
2 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
Chloroform: Soluble; DMSO: Soluble; Water: Soluble | [form ]
solid | [pka]
11.00±0.46(Predicted) | [Water Solubility ]
readily soluble | [Merck ]
13,32 | [BRN ]
1936365 | [InChI]
InChI=1S/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7) | [InChIKey]
YASYVMFAVPKPKE-UHFFFAOYSA-N | [SMILES]
P(NC(C)=O)(SC)(OC)=O | [NIST Chemistry Reference]
Acephate(30560-19-1) | [EPA Substance Registry System]
Phosphoramidothioic acid, acetyl-, O,S-dimethyl ester(30560-19-1) |
| Hazard Information | Back Directory | [Chemical Properties]
Acephate is an organophosphate foliar spray insecticide of moderate persistence with
residual systemic activity. It is a contact and systemic insecticide and very effective against
a large number of crop pests, such as alfalfa looper, aphids, armyworms, bagworms, bean
leafbeetle, bean leafroller, blackgrass bugs, bollworm, budworm, and cabbage looper. | [Chemical Properties]
White Solid | [Uses]
Contact and systemic insecticide | [Definition]
ChEBI: A phosphoramide that is methamidophos in which one of the hydrogens is replaced by an acetyl group. | [General Description]
A white solid. Used as a contact and systemic insecticide. | [Air & Water Reactions]
Soluble in water. | [Reactivity Profile]
A thiophosphate ester. Organothiophosphates 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. | [Biological Activity]
Anticholinesterase insecticide that produces cholinotoxicity. Displays weak inhibition of rat acetylcholinesterase (AChE) but potently inhibits cockroach AChE. | [Health Hazard]
Acephate is a colorless to white, solid organophosphate insecticide. Exposures to acephate
cause poisoning to animals and humans. Acephate inhibits acetylcholine esterase (AchE),
the essential nervous system enzyme, and causes characteristic organophosphate poi-
soning. The symptoms of toxicity include, but are not limited to, headache, nervousness,
blurred vision, weakness, nausea, fatigue, stomach cramps, diarrhea, diffi
culty breathing,
chest pain, sweating, pin-point pupils, tearing, salivation, clear nasal discharge and spu-
tum, vomiting, muscle twitching, muscle weakness, and in severe poisonings, convulsions, respiratory depression, coma, and death. Acephate causes cholinesterase inhibition lead-
ing to overstimulation, respiratory paralysis, and death. | [Potential Exposure]
Acephate is a general use contact and systemic insecticide. Banned in the EU for use as a biocide and agricultural insecticide. Used on green- and limabeans, Brussels sprouts, cauliflower, celery, cotton, cottonseed, cranberries, head lettuce, macadamia nuts, peanuts, bell-and nonbell peppers, peppermint, spearmint, tobacco, and soybeans (Special Local Need Registration required in Mississippi and Texas only). Also used to control cockroach (spot treatment only) in residential and industrial buildings and insect control in forests, and on ornamental plants and to target armyworms, aphids, beetles, bollworms, borers, budworms, cankerworms, crickets, cutworms, fire ants, fleas, grasshoppers, leafhoppers, loopers, mealybugs, mites, moths, roaches, spiders, thirps, wasps, weevils, whiteflies, etc. banned for use in the EU. | [First aid]
Treatment for organophosphate poisoning consists of thorough decontamination, cardiorespiratory support, and administration of the antidotes atropine and pralidoxime. In cases of severe poisoning, diazepam, an anticonvulsant, should also be administered. Antidotes should be administered as prevention even if the diagnosis is in doubt. Speed in removing material from eyes and skin is of extreme importance. Eyes: Contact can cause dangerous amounts of these chemicals to be quickly absorbed through the mucous membrane into the bloodstream. Immediately and gently flush eyes with plenty of warm or cold water (NO hot water) for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Skin: Get medical aid. Dermal contact can cause dangerous amounts of these chemicals to be absorbed into the bloodstream. Wearing the appropriate PPE equipment and respirator for organophosphate pesticides, immediately flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Shampoo hair promptly if contaminated. The removed, contaminated clothing and shoes should be double-bagged and left in Hot Zone for later disposal by hazardous materials experts. Skin may also be decontaminated with diluted hypochlorite solution. Inhalation: Get medical aid. Do not contaminate yourself. Wearing the appropriate PPE equipment and respirator for organophosphate pesticides, immediately remove the victim from the contaminated area to fresh air. If the victim is not breathing, administer artificial respiration. Do not use mouth-tomouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. If breathing is difficult, administer oxygen through bag/mask apparatus until medical help arrives. Do not leave victim unattended. Ingestion: Call poison control. Loosen all clothing. Never give anything by mouth to an unconscious person. If victim is unconscious or having convulsions, do nothing except keep victim warm. Get medical aid. Transfer promptly to a medical facility. In cases of ingestion, do not induce vomiting. If the victim isalert and asymptomatic, administer a slurry of activated charcoal at a dose of 1 g/kg (infant, child, and adult dose). A soda can and straw may be of assistance when offering charcoal to a child. In some cases you may be specifically instructed by poison control to induce vomiting by way of 2 tablespoons of syrup of ipecac (adult) washed down with a cup of water. Do NOT give activated charcoal before or with ipecac syrup. | [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 material | [Incompatibilities]
May react with strong oxidizers such as chlorates, peroxides, nitrates, etc. In the presence of strong reducing agents such as hydrides, organophosphates form highly toxic and flammable phosphine gas. Contact with oxidizers can cause the release of toxic oxides of phosphorus. 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).
| [Waste Disposal]
Alkaline hydrolysis or incineration. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. | [Agricultural Uses]
Insecticide: Acephate is a general use contact and systemic
insecticide. Not approved for use in EU countries.
Actively registered in the U.S., homeowner use for lawns
is discontinued except for treatment of fire ant mounds.
Other indoor treatment has been discontinued. Used on
green and lima beans, Brussels sprouts, cauliflower, celery, cotton, cottonseed, cranberries, head lettuce, macadamia nuts, peanuts, bell-and non-bell peppers, peppermint,
spearmint, tobacco, and soybeans (Special Local Need
Registration required in Mississippi and Texas only). Also
used to control cockroach (spot treatment only) in residential and industrial buildings and insect control in forests, and on ornamental plants and to target armyworms,
aphids, beetles, bollworms, borers, budworms, cankerworms, crickets, cutworms, fire ants, fleas, grasshoppers,
leafhoppers, loopers, mealybugs, mites, moths, roaches,
spiders, thirps, wasps, weevils, whiteflies, etc. | [Trade name]
ACECAP SYSTEMIC INSECTICIDE
IMPLANTS®; ACEFAL 75 PS®; ACEHERO®;
ACEPHATE 97 EG®; ACEPHATE 75SP®; ACEPHATE
PCO SP INSECTICIDE®; ACESUL®; ACE-TOX®;
ACHERO®; ACIFAT®; ADDRESS®; AIMTHENE®;
AMCOTHENE®; ASATAF®; ASIFY®; ATTACK®;
CHEVRON RE 12420®; CLEAN CROP ACEPHATE 80
DF SEED PROTECTORANT®; DREXEL ACEPHATE 75
WSP®; DREXEL ACEPHATE PCO SP INSECTICIDE®;
FATEL®; FORPHATE®, FORWARD®; KITRON®;
KORANDA® (acephate + fenvelerate); LANCER®;
ORCEPHATE®; ORTHENE®; ORTHENE 755®;
Acephate 3
ORTHO 12420®; ORTRAN®; ORTRIL®; PACE®;
PAYLOAD®; PILARTHENE®; PINPOINT®; PRECISE
ACEPHATE®; RACET®; RE 12420®; SAPHATE®; 75
SP®; VALENT ORTHENE TECHNICAL®; VEGFRU
TARGET® | [Carcinogenicity]
Acephate showed no evidence of
carcinogenicity among rats given diets with 0, 5, 50, or
700 ppm (equivalent to about 0, 0.25, 2.5, and 35.0 mg/kg/
day, respectively) for 28 months . | [Environmental Fate]
Soil. In aerobic and anaerobic soils, methamidophos and carbon dioxide were identified
as the major soil metabolites (Hartley and Kidd, 1987). The estimated half-life in soil is
3 days (Wauchope, 1988)
Plant. Acephate is quickly absorbed, translocated and transformed in pine seedlings
(Werner, 1974) and cotton plants (Bull, 1979). The chemical was metabolized via cleavage
of the amide bond to form methamidophos (O,S-dimethyl phosphoramidothioat
Chemical/Physical. Emits toxic fumes of phosphorus, nitrogen and sulfur oxides when
heated to decomposition (Sax and Lewis, 1987) | [Metabolic pathway]
Acephate is a systemic insecticide with a very favourable mammalian
toxicity. The initial reaction of the biotransformation of acephate is by
hydrolysis to the active acetylcholinesterase inlubitor methamidophos. In
every case where the metabolism of acephate has been studied in biological
systems, the production of methamidophos has been demonstrated;
however, the amount of this presumed active metabolite varies
greatly from organism to organism. In mammals, which are relatively
insensitive to the insecticide, the primary route of stage I metabolism is
mainly degradative via O-demethylation to give des-O-methylacephate.
Further metabolism in mammals and birds leads to incorporation of the
molecule into proteins, carbohydrates and lipids as well as to excretion.
Conjugates have not been identified. | [Degradation]
Acephate is relatively stable to hydrolysis, with DT50s of 60 hours at pH 9
and 710 hours at pH 3 and 40 °C (PM).
Chukwudebe et al. (1984) studied the breakdown of acephate in 0.1M
Tris-HCl buffer at pH 7.2, 8.1 and 8.6 at 37 °C. The hydrolysis products
were analysed by GLC with FID for acephate and methamidophos and
TLC separation and GLC analysis for the other products. Authenticated
standards [methamidophos (2), des-O-methylacephate (3), des-S-methylacephate
(4) and O,S-dimethyl phosphorothioate (5)] were used to
calibrate the analysis. The major metabolite at all pH values was O,S-dimethyl
phosphorothioate (5). This reached a maximum concentration
of 40-55% in 1-3 days depending on pH. Its concentration then declined
as it was itself hydrolysed. The hydrolysis of acephate was strongly
biphasic, with hydrolysis becoming very slow after about 2 days. The
amounts of methamidophos (2) (3%) and des-S-methylacephate (4) (10%)
produced after 7 days were minor. Major and minor routes for the
hydrolysis of methamidophos are shown in Scheme 1. | [Toxicity evaluation]
Although methamidophos is highly toxic to mammals
(LD50 mice = 27 mg/kg), the acetylation causes a dramatic
decrease in the mammalian toxicity; the acute oral
LD50 values of acephate for mice and rats are 361 and
945 mg/kg, respectively. Inhalation LC50 is >15 mg/L air.
In 2 years of feeding trials, dogs showed depression of
cholinesterase at 100 mg/kg diet (5 mg/kg/d) (maximum
dose level). ADI is 0.03 mg/kg. |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,F | [Risk Statements ]
22-36-20/21/22-11 | [Safety Statements ]
2-36-36/37-16 | [RIDADR ]
UN1648 3/PG 2 | [WGK Germany ]
2 | [RTECS ]
TB4760000 | [HS Code ]
29299040 | [Safety Profile]
Poison by ingestion.
Moderately toxic by skin contact and
inhalation. Human mutation data reported.
When heated to decomposition it emits very
toxic fumes of NOx, POx, and SOx. See also
ESTERS. | [Hazardous Substances Data]
30560-19-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 700 mg/kg (Magee, 1973) |
| Questions And Answer | Back Directory | [Description]
Acephate(also known as Orthene) is a kind of organophosphate foliar insecticide which can be used for the treatment of leaf miners, caterpillars, sawflies and thrips in crops and aphides in vegetables and horticulture. It is one of the 10 most important organophosphate insecticides in the 1990s, and is still being widely used today. It takes effect through inhibiting the activity of acetylcholinesterase (Ache) after being metabolically converted to methamidophos. Since it can’t be converted to methamidophos, it is thought to cause no effect on animals and human beings.
| [Toxicity and health effects]
Acephate is a colorless to white, solid organophosphate insecticide. Exposures to acephate cause poisoning to animals and humans. Acephate inhibits acetylcholine esterase (AchE), the essential nervous system enzyme, and causes characteristic organophosphate poisoning. The symptoms of toxicity include, but are not limited to, headache, nervousness, blurred vision, weakness, nausea, fatigue, stomach cramps, diarrhea, diffi culty breathing, chest pain, sweating, pin-point pupils, tearing, salivation, clear nasal discharge and sputum, vomiting, muscle twitching, muscle weakness, and in severe poisonings, convulsions,respiratory depression, coma, and death. Acephate causes cholinesterase inhibition leading to overstimulation, respiratory paralysis, and death.
| [Acephate and carcinogenicity]
The US EPA classified acephate as Group C, meaning a possible human carcinogen.
| [References]
[1] Mahajna, Mahmoud, G. B. Q. And, and J. E. Casida. "Acephate Insecticide Toxicity: Safety Conferred by Inhibition of the Bioactivating Carboxyamidase by the Metabolite Methamidophos." Chemical Research in Toxicology 10.1(1997): 64-9.
[2] Danka, Robert G., et al. "Doses and residues of acephate baits used to eradicate undesirable honey bees: A hazard assessment." Bulletin of Environmental Contamination & Toxicology 47.3(1991): 422.
[3] Wang, X., et al. "Environmental behavior of the chiral organophosphorus insecticide acephate and its chiral metabolite methamidophos: enantioselective transformation and degradation in soils. " Environmental Science & Technology 47.16(2013): 9233-9240.
[4] EXTOXNET. 1995. Acephate. Pesticide Information Profi les. Extension Toxicology Network. Cornell University, Ithaca, NY (updated 2001).
[5] Routt, R.J. and Roberts, J.R. 1999. Organophosphate insecticides. Recognition and Management of Pesticide Poisonings. US Environmental Protection Agency, National Technical Information Service (US EPA 735-R-98-003; pp. 55–57), Washington, DC.
[6] Tomlin, C.D.S. (ed.). 2008. The Pesticide Manual, 15th ed. British Crop Protection Council (BCPC). Blackwell Scientifi c, Hampshire, U.K.
US Environmental Protection Agency (US EPA). 1987. Acephate. Pesticide Fact Sheet. National Technical Information Service. US EPA, Washington, DC.
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