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Home> Encyclopedia >   /  Agrochemicals & Pesticides  /  Insecticide  /  Agrochemical Intermediates  /  Organic Intermediate  /  Herbicide
Acephate structure
Acephate structure

Acephate

Iupac Name:N-[methoxy(methylsulfanyl)phosphoryl]acetamide
CAS No.:30560-19-1
Molecular Weight:183.162
Introduction: 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.
1. Names and Identifiers
1.1 Name
Acephate
1.2 Synonyms

acetylphosphoramidothioicacido,s-dimethylester Chevron re 12,420 chevronorthene chevronre12,420 ENT 27822 ent27822 N-(Methoxy(methylthio)phosphinoyl)acetamide o,S-Dimethyl acetylamidothiophosphate

1.3 CAS No.
30560-19-1
1.4 CID
1982
1.5 EINECS(EC#)
250-241-2
1.6 Molecular Formula
C4H10NO3PS (isomer)
1.7 Inchi
InChI=1S/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7)
1.8 InChkey
YASYVMFAVPKPKE-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(=O)NP(=O)(OC)SC
1.10 Isomers Smiles
CC(=O)NP(=O)(OC)SC
2. Properties
3.1 Density
1.35
3.2 Melting Point
93℃
3.3 Boiling Point
2 °C
3.4 Vapour
2.26 x 10-4 Pa (24 °C)
3.5 Refractive Index
1.475
3.6 Flash Point
2?°C
3.7 Appearance
White crystalline powder
3.8 Carcinogenicity
The US EPA classified acephate as Group C, meaning a possible human carcinogen.
3.9 Chemical Properties
White Solid
3.10 Color/Form
Colorless crystals
Colorless to white solid
3.11 pKa
11.00±0.46(Predicted)
3.12 Stability
Relatively
3.13 StorageTemp
APPROX 4°C
3.14 Water Solubility
Very soluble (slightly soluble in acetone and alcohol)
3. Use and Manufacturing
4.1 Agricultural Uses
Insecticide: Acephate is a general use contact and systemicinsecticide. Not approved for use in EU countries.Actively registered in the U.S., homeowner use for lawnsis discontinued except for treatment of fire ant mounds.Other indoor treatment has been discontinued. Used ongreen 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 NeedRegistration required in Mississippi and Texas only). Alsoused 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.
4.2 Definition
ChEBI: A phosphoramide that is methamidophos in which one of the hydrogens is replaced by an acetyl group.
4.3 Environmental Fate
Soil. In aerobic and anaerobic soils, methamidophos and carbon dioxide were identifiedas the major soil metabolites (Hartley and Kidd, 1987). The estimated half-life in soil is3 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 cleavageof the amide bond to form methamidophos (O,S-dimethyl phosphoramidothioatChemical/Physical. Emits toxic fumes of phosphorus, nitrogen and sulfur oxides whenheated to decomposition (Sax and Lewis, 1987)
4.4 General Description
A white solid. Used as a contact and systemic insecticide.
4.5 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.
4.6 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.
4.7 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
4.8 Usage
Contact and systemic insecticide for control of sucking and chewing insects incotton, ornamentals, forestry, tobacco, fruits, vegetables and other crops
4.9 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. Acephate Preparation Products And Raw materials Raw materials
4. Safety and Handling
5.1 Hazard Codes
Xn
5.2 Risk Statements
R22
5.3 Safety Statements
S2;S36
5.4 HazardClass
6.1
5.5 PackingGroup
I; II; III
5.6 Transport
50kgs
5.7 Cleanup Methods
Environmental considerations- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, liquid and solid, NOS/
Environmental considerations- water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid and solid, NOS/
Environmental considerations- air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid and solid, NOS/
5.8 DisposalMethods
Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/
Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/
SMALL SPILL: Sweep up material and place in disposable container. ... LARGE SPILL: Clean up spills immediately, observing precautions in Exposure Controls/ Personal Protection section. Vacuum with machines equipped with high efficiency filters or sweep up material and place in a disposable container. Scrub contaminated area with detergent and water using a stiff broom. Pick up liquid with Oil Dry, cat litter, clay, rags or other absorbent and place in a disposable container. /Orthene Fire Ant Killer 1 (50% acephate)/
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.
5.9 Fire Fighting Procedures
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/
If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/
5.10 Formulations/Preparations
BONIDE SYSTEMIC INSECTICIDE GRANULES Active Ingredient 1.5% Acephate
DEXOL SYSTEMIC PLANT CARE Active Ingredient 1.5% Acephate
MULTITUDE 75WSP INSECTICIDE Active Ingredient 75.0% Acephate
ORTHENE SYSTEMIC ROSE & FLOWER CARE and ORTHENE GRANUALS Active Ingredient 1.5 % Acephate
ORTHENE SYSTEMIC INSECT CONTROL Active Ingredient 9.40% Acephate
ORTHO SYSTEMIC ROSE & FLORAL SPRAY Active Ingredient 0.1% Resmethrin, 0.25% Acephate, 0.10% Triforine
ISOTOX INSECT KILLER FORMULA IV active ingredient 8.0% Acephate, 0.50% Fenbutatin-oxide
ORTHO ORTHENE FIRE ANT KILLER FORMULA II Active Ingredient 50.0% Acephate
WHITMIRE MICRO-GEN PT 1320 TR Active Ingredient 12.0% Acephate
WHITMIRE TC 136 Active Ingredient 1.5% Acephate,1.0% Fenpropathrin
BORER-STOP ECOTAB Active Ingredient 97% Acephate
ACE-JET Active Ingredient 97.4% Acephate
PRECISE ACEPHATE Active Ingredient 4.0% Acephate
LANCER TECHNICAL Active Ingredient 98.3% Acephate
CHEMINOVA ACEPHATE 90SP Active Ingredient 90% Acephate
Soluble powder, granules.
Technical product (80-90% pure)
25% soluble powder, 75% suspension, 0.25-1% pressurized sprays; various granular formulations.
Wettable powder, soluble powder, soluble extruded pellets, granular, and liquid formulations
Technical grade is 97% pure
5.11 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).
5.12 Octanol/Water Partition Coefficient
log Kow = -0.85
5.13 Other Preventative Measures
... NOTES TO PHYSICIAN: This material contains a cholinesterase inhibitor. Measurement of blood cholinesterase activity may be useful in monitoring exposure. If signs and/or symptoms of cholinesterase inhibition appear, atropine sulfate is antidotal. ... PROTOPAM is also antidotal and may be used in conjunction with atropine but should not be used alone. /Orthene Fire Ant Killer 1 (50% acephate)/
In order to mitigate occupational risks, the following risk mitigation measures are necessary: Formulate all soluble powder formulations into water soluble bags, except for soluble powders sold for fire ant, harvester ant, or hopper box seed treatment uses. Limit the 1 pound active ingredient per acre (lb ai/A) cotton aerial application rate to cotton grown in California and Arizona; reduce the maximum aerial application rate for cotton to 0.75 ai/A for all other areas of the United States. Delete aerial application to turf. Require enclosed cockpits and mechanical flagging for all aerial applications. Reduce maximum sod farm and golf course turf application rates (non-granular formulations) to 3 lb ai/A and 4 lb ai/A, respectively. Reduce maximum application rates for greenhouse floral and foliage plant crops, and outdoor floral and ground covers to 1 lb ai per 100 gallons water (not to exceed 0.75 lb ai/A for cut flowers and 1.0 lb ai/A for other ornamentals). Delete the application of acephate by low pressure handwand to treat trees, shrubs, and outdoor flora; for the control of wasps; and for perimeter treatment by PCOs. Delete the use of granular formulations to be applied by belly grinder, shaker can, or by hand to trees, shrubs, and 12" pots. Add personal protective equipment to end use product labels for workers who mix and load, and/or apply acephate.
In order to mitigate residential postapplication risk, the following risk mitigation measures are necessary: Delete residential indoor uses. Delete all turfgrass uses (except golf course, sod farm, and spot or mound treatment for ant control). Establish a 3 day pre-harvest interval (PHI) for the harvesting of sod.
Keep out of reach of children. Avoid contact with mouth, skin, and eyes.
In case of damage to, or leaking from containers of this material, contact the Pesticide Safety Team Network at (800) 424-9300. /Organophosphorus pesticide, solid not otherwise specified, (cmpd & prepn) (insecticide, other than agricultural, not elsewhere classified); Organophosphorus pesticide, liq, not otherwise specified (cmpd & prepn) (agricultural insecticides, not elsewhere classified, liq), (insecticides, other than agricultural, not otherwise classified), and (agricultural insecticides, not elsewhere classified, liq); Organophosphorus pesticide, solid, not otherwise specified (cmpd & prepn) (insecticides, other than agricultural, not elsewhere classified); and (agricultural insecticides, not elsewhere classified, other than liq)/
The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed ... each time when it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Organophosphorus pesticides/
In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/
Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/
Small packages of pesticides are preferable for individual application in order to limit the quantities to be weighed & metered. A special vessel with long stirring rod for dilution & suspension of the poison must be available in order to reduce manual handling to a minimum. The strict observance of hygiene rules--no smoking & no food intake during work. Thorough washing with soap after work, changing protective clothing before going home--is of utmost importance. /Organophosphorus pesticides/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning. /Organophosphorus pesticides/
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, flammable, toxic/
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, liquid, NOS/
Personnel protection: Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. /Organophosphorus pesticides, liquid, flammable, toxic/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, solid, NOS/
5.14 Protective Equipment and Clothing
Workers handling and applying organophosphate pesticides (opp) must ... be given personal protective equipment comprising overalls made of a tight fabric or polyvinyl chloride, gloves, and rubber boots. They must wear a respirator with an activated-carbon gas filter cartridge affording protection for a determined number of working hours. The eyes should be protected by goggles. The signalmen for aerial dusting operations should be equipped with a hat and cape made of polyvinyl chloride or a fabric impregnated with a water repellent. /Pesticides, organophosphorus/
PERSONAL PROTECTION EYES AND FACE: For application of product in accordance with label instructions, no special eye protection is needed. Handling of the product is not likely to present an eye exposure concern during normal handling. In the event of an accidental discharge of the material during manufacture or handling which could cause eye contact, workers should wear goggles or a face shield. SKIN: Wear protective clothing when handling or applying this product including long pants, long sleeved shirt, socks, shoes, and chemical resistant gloves. RESPIRATORY: No special respiratory protection is normally required. However, if operating conditions create airborne concentrations which exceed the recommended exposure standards, the use of an approved respirator is required. /Orthene Fire Ant Killer 1(50% acephate)/
Personnel protection ... Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, flammable, toxic/
Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Organophosphorus pesticides, liquid and solid, NOS/
5.15 Safety

when exposure to acephate,it will have a slight irritation to eyes and skin.
Hazard Codes:? Xn,F
Acephate's Risk Statements:
22:Harmful if swallowed?
36:Irritating to the eyes?
20/21/22:? Harmful by inhalation, in contact with skin and if swallowed
Acephate's Safety Statements:
2:Keep out of the reach of children?
36:Wear suitable protective clothing?
36/37:Wear suitable protective clothing and gloves?
16:? Keep away from sources of ignition - No smoking?
RIDADR? UN1648 3/PG 2

5.16 Skin, Eye, and Respiratory Irritations
Organophosphorus cmpd can produce dermal irritation but most are weak sensitizers. /Organophosphorus cmpd/
5.17 Toxicity

when acephate heated to decomposition,it emits toxic fumes of phosphorus, NITROGEN, and SULFUR oxides.
RTECS? TB4760000

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Precursor and Product
9. Computational chemical data
  • Molecular Weight:183.162g/mol
  • Molecular Formula:C4H10NO3PS
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:183.01190135
  • Monoisotopic Mass:183.01190135
  • Complexity:172
  • Rotatable Bond Count:3
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:4
  • Topological Polar Surface Area:80.7
  • Heavy Atom Count:10
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:1
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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