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30560-19-1

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30560-19-1 Usage

Description

Different sources of media describe the Description of 30560-19-1 differently. You can refer to the following data:
1. 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.
2. 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.

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.

Chemical Properties

Different sources of media describe the Chemical Properties of 30560-19-1 differently. You can refer to the following data:
1. White Solid
2. 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.
3. Colorless crystalline solid (80% or more pure) or white powder (technical). Has an odor of rotten cabbage or mercaptans (like sulfur).

Uses

Different sources of media describe the Uses of 30560-19-1 differently. You can refer to the following data:
1. Contact and systemic insecticide for control of sucking and chewing insects in cotton, ornamentals, forestry, tobacco, fruits, vegetables and other crops
2. 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.
3. Acephate is used to control a wide range of sucking and chewing insects in a large number of crops.

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.

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.

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?

Biological Activity

Anticholinesterase insecticide that produces cholinotoxicity. Displays weak inhibition of rat acetylcholinesterase (AChE) but potently inhibits cockroach AChE.

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.

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.

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 phosphoramidothioatChemical/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.

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

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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 30560-19-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,0,5,6 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 30560-19:
(7*3)+(6*0)+(5*5)+(4*6)+(3*0)+(2*1)+(1*9)=81
81 % 10 = 1
So 30560-19-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7)

30560-19-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name acephate

1.2 Other means of identification

Product number -
Other names 75 SP

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Insecticide
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:30560-19-1 SDS

30560-19-1Synthetic route

acetamide
60-35-5

acetamide

phosphorochloridothioic acid,O,S-dimethyl ester
3711-50-0

phosphorochloridothioic acid,O,S-dimethyl ester

Acephate
30560-19-1

Acephate

Conditions
ConditionsYield
With triethylamine In toluene at 5 - 30℃; for 5h; Reagent/catalyst; Temperature; Concentration;84%
With hydrogenchloride In water for 14h; Reflux;102 g
acetamide
60-35-5

acetamide

dimethyl chlorothiophosphate
2524-03-0

dimethyl chlorothiophosphate

Acephate
30560-19-1

Acephate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 60℃;63%
calcium salt of O,S-dimethyl-N-acetylphosphoroamidothioate

calcium salt of O,S-dimethyl-N-acetylphosphoroamidothioate

Acephate
30560-19-1

Acephate

acetic anhydride
108-24-7

acetic anhydride

Acephate
30560-19-1

Acephate

Conditions
ConditionsYield
With sulfuric acid Heating;
With sulfuric acid In dichloromethane at 60 - 70℃; for 2.5h; Large scale;
With sulfuric acid at 35 - 45℃; for 2.5h; Large scale;4826 kg
O,O-dimethyl N-acetylphosphoramidothioate
42072-27-5

O,O-dimethyl N-acetylphosphoramidothioate

dimethyl sulfate
77-78-1

dimethyl sulfate

Acephate
30560-19-1

Acephate

Conditions
ConditionsYield
In dichloromethane Heating;
Acephate
30560-19-1

Acephate

C3H7NO3PS(1-)*Na(1+)

C3H7NO3PS(1-)*Na(1+)

Conditions
ConditionsYield
With sodium iodide In acetone for 4h; Heating;100%
ethanol
64-17-5

ethanol

Acephate
30560-19-1

Acephate

A

methanesulfonic acid
75-75-2

methanesulfonic acid

B

Acetyl-phosphoramidic acid ethyl ester methyl ester

Acetyl-phosphoramidic acid ethyl ester methyl ester

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid
Acephate
30560-19-1

Acephate

demethylthioacephate
82452-61-7

demethylthioacephate

Conditions
ConditionsYield
With water; triethylamine; 3-chloro-benzenecarboperoxoic acid
With 3,3-dimethyldioxirane In water-d2; acetone for 24h;
Acephate
30560-19-1

Acephate

A

methanesulfonic acid
75-75-2

methanesulfonic acid

B

sec-butyl methanesulfonate
16156-54-0

sec-butyl methanesulfonate

C

demethylthioacephate
82452-61-7

demethylthioacephate

D

Acetyl-phosphoramidic acid sec-butyl ester methyl ester

Acetyl-phosphoramidic acid sec-butyl ester methyl ester

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acidA n/a
B n/a
C 52 % Spectr.
D 48 % Spectr.
Acephate
30560-19-1

Acephate

Barium Salt of O,S-Dimethyl-N-Acetylphosphoroamidothioate

Barium Salt of O,S-Dimethyl-N-Acetylphosphoroamidothioate

Conditions
ConditionsYield
With barium dihydroxide In dichloromethane
Acephate
30560-19-1

Acephate

Sodium Salt of O,S-Dimethyl-N-acetylphosphoroamidothioate

Sodium Salt of O,S-Dimethyl-N-acetylphosphoroamidothioate

Conditions
ConditionsYield
With sodium carbonate In methanol
Acephate
30560-19-1

Acephate

calcium salt of O,S-dimethyl-N-acetylphosphoroamidothioate

calcium salt of O,S-dimethyl-N-acetylphosphoroamidothioate

Conditions
ConditionsYield
With calcium hydroxide In methanol
Acephate
30560-19-1

Acephate

tin(IV) chloride
7646-78-8

tin(IV) chloride

N-(O,S-dimethylphosphoryl)acetamide stannic chloride complex
183606-67-9

N-(O,S-dimethylphosphoryl)acetamide stannic chloride complex

Conditions
ConditionsYield
solvent: CH2Cl2 or pentane; Sn-compd. addn. (dropwise) to soln. of ligand; ppt. filtration off, washing with solvent; elem. anal.;
Acephate
30560-19-1

Acephate

phosphoramidic acid monomethyl ester
19255-94-8

phosphoramidic acid monomethyl ester

Conditions
ConditionsYield
With 10 wt% La2O3/Bi2O3 doped silver orthophosphate for 2h; Kinetics; Photolysis;

30560-19-1Relevant articles and documents

PROCESS FOR PREPARATION OF THIOPHOSPHORYL CHLORIDE AND ACEPHATE

-

Page/Page column 25, (2021/04/23)

The present invention discloses an improved process for preparation of acephate and intermediates thereof. More particularly, the present invention relates to a process for preparation of thiophosphoryl chloride useful for commercial production of pesticides and pharmaceutically active compounds.

A heterogeneous reaction

-

Paragraph 0125; 0126, (2017/02/24)

The invention discloses a highly selective novel reaction with an important application value in organic phosphorus synthesis methodology. The reaction can be applied in important pesticide commodities of acephate, glyphosate, glufosinate-ammonium, chloramine phosphorus, profenofos, and the like. With the reaction, innovative technical synthetic routes can be designed. With the reaction, standards of clean production technologies can be satisfied, and the production cost is greatly reduced compared to existing technical routes.

Synthesis and characterization of O,S-dimethylphosphoramidothioate and N-acetyl O,S-dimethylphosphoramidothioate

Ghadimi,Mousavi,Rahnama,Rahimi

scheme or table, p. 347 - 354 (2010/07/03)

O,S-Dimethylphosphoramidothioate (methamidophos) and N-acetyl O,S-dimethylphos- phoramidothioate (acephate) were synthesized by new methods to investigate the structure-activity study of acetyl cholinesterase (AChE) inhibition through the parameters of logP,δ 31P, and IC 50. After their characterization by NMR (31P, 31P{1H}, 13C, and 1H), IR, and mass spectroscopy, logP and δ31P (31P chemical shift in NMR) were used to evaluate lipophilicity and electronical properties. The logP values for methamidophos and acephate were experimentally determined by the GC-shake-flask method, and the ability of the compounds to inhibit human AChE was evaluated by a modified Ellman's assay. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

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