86-50-0

Basic information

• Product Name: AZINPHOS-METHYL
• Synonyms: S-(3,4-DIHYDRO-4-OXOBENZO[D]-[1,2,3]-TRIAZINE-3-YL-METHYL)O,O-DIMETHYL PHOSPHORODITHIOATE;O,O-DIMETHYL-S-[4-OXO-1,2,3-BENZOTRIAZIN-3(4H)-YLMETHYL]PHOPHORODITHIOATE;O,O-DIMETHYL-S-[4-OXO-1,2,3-BENZOTRIAZIN-3(4H)-YLMETHYL]PHOSPHORODITHIOATE;R1582;1,2,3-Benzotriazin-4(3H)-one, 3-(mercaptomethyl)-, O,O-dimethyl phosphorodithioate;1,2,3-benzotriazin-4(3h)-one,3-(mercaptomethyl)-,o,o-dimethylphosphorodith;1,2,3-benzotriazin-4(3h)-one,3-(mercaptomethyl)-,o,o-dimethylphosphorodithio;2,3-benzotriazin-4(3h)-one
• CAS NO: 86-50-0
• Molecular Formula: C₁₀H₁₂N₃O₃PS₂
• Molecular Weight: 317.32
• EINECS: 201-676-1
• Product Categories: NULL
• Mol File: 86-50-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 73℃
• Boiling Point: 421.3 °C at 760 mmHg
• Flash Point: 208.6 °C
• Appearance: /solid
• Density: 1.44 g/cm3 (20℃)
• Vapor Pressure: 2.64E-07mmHg at 25°C
• Refractive Index: 1.6115 (589.3 nm 76℃)
• Storage Temp.: 0-6°C
• PKA: -2.60±0.20(Predicted)
• Water Solubility: 28 mg l-1(20 °C)
• Merck: 13,915
• BRN: 280476
• CAS DataBase Reference: AZINPHOS-METHYL(CAS DataBase Reference)
• NIST Chemistry Reference: AZINPHOS-METHYL(86-50-0)
• EPA Substance Registry System: AZINPHOS-METHYL(86-50-0)

Safety Data

• Hazard Codes: T+,N
• Statements: 24-26/28-43-50/53-28
• Safety Statements: 28-36/37-45-60-61
• RIDADR: 2783
• WGK Germany: 3
• RTECS: TE1925000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 86-50-0(Hazardous Substances Data)

Usage

Description

AZINPHOS-METHYL, also known as Glycerol, is an organic compound that serves as a versatile building block in various industries. It is a colorless, odorless, and viscous liquid with a sweet taste. Its unique molecular structure, featuring three hydroxyl groups, allows it to form hydrogen bonds and participate in numerous chemical reactions, making it a valuable raw material in different applications.
Used in Agricultural Industry:
AZINPHOS-METHYL is used as a nonsystemic insecticide and acaricide for the control of insect pests in blueberry, grape, maize, vegetable, cotton, and citrus crops. It effectively targets a wide range of both sucking and chewing insects and spider mites, ensuring the protection and yield of these crops.
Used in Fruit Industry:
AZINPHOS-METHYL is used as an insecticide for fruit, with its application potentially being restricted due to its potential impact on the environment and human health. It helps in controlling pests that can damage the fruit, thus maintaining the quality and quantity of the produce.

Air & Water Reactions

Insoluble in water. What little amount is solubilized will readily hydrolyze.

Reactivity Profile

The BPS Pesticide incident in Helena resulted in an explosion and death of three firemen. The burning of a 1,000 pound sack of Azinphos Methyl or the flashing of Maneb which was present on the facility may have caused the explosion. Azinphos Ethyl may behave similarly. At elevated temperatures, AZINPHOS-METHYL will decompose generating toxic gases.

Hazard

A poison, cholinesterase inhibitor. Absorbed by skin. Questionable carcinogen.

Health Hazard

Azinphos methyl is extremely toxic, the probable lethal oral dose for humans being from 5 to 50 mg/kg body weight (just seven drops). Different solvents used in the preparation and commercial formulations of azinphos methyl further change the toxicological properties. The symptoms of poisoning include, but are not limited to, excessive sweating, headache, weakness, giddiness, nausea, hypersalivation, vomiting, stomach pains, blurred vision, slurred speech, and muscle twitching, and with advanced time and poisoning, chest tightness, vomiting, cramps, convulsion, coma, loss of refl exes and loss of sphincter control, respiratory failure, unconsciousness, or death. Reports have indicated that azinphos methyl causes no delayed neurotoxicity. Azinphos methyl has been classifi ed as a tumorigen. After accidental or intentional exposure to azinphos methyl, occupational workers exhibit over stimulation of the nervous system, rapid twitching and paralysis of muscles, and death.

Health Hazard

Acute: extremely toxic. Probable oral lethal dose in humans is 5-50 mg/kg, or between 7 drops and 1 teaspoon for a 70 kg (150 lb.) person. A potent cholinesterase inhibitor which can cause death.

Health Hazard

Cholinesterase inhibitor; a severely acutetoxicant; delayed effects may be observedafter several hours; toxic symptoms simi-lar to other organophosphorus compounds;exposure may cause headache, dizziness,blurred vision, and muscle spasms. Othertoxic symptoms include vomiting, abdomi-nal pain, diarrhea, seizures, and shortness ofbreath; ingestion of 5–10 g could be fatalto adult humans; oral LD50 value (mice):15 mg/kg, rats 7 mg/kg; LC50 inhalation(rat): 69 mg/m3/1h.

Fire Hazard

Some of the formulations may burn, but none of them ignite easily. Container may explode in the heat of the fire. Rapidly hydrolyzed by cold alkali or cold acid. Unstable at temperatures above 390F.

Trade name

ACIFON?; AZINPHOS-METHYL GUTHION?; BAY 9027?; BAYER 17147?; CARFENE?; COTNION-METHYL?; CRYSTHION 2 L?; CRYSTHYON?; DBD?; GOTHNION?; GUSATHION?; GUSATHION M?; GUTHION?; R 1582?

Safety Profile

Poison by inhalation, ingestion, skin contact, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. See also PARATHION and ESTERS. When heated to decomposition it emits very toxic fumes of POx, SOx, and NOx.

Carcinogenicity

In a 2 year study dogs received azinphos-methyl technical (purity not stated) in the diet at 0, 5, 20, or 50 ppm . After 36 weeks, the 20 ppm and 50 ppm dose groups were given 50 and 100 ppm, respectively, upon lack of toxic symptoms. After 57 weeks, the 100 ppm dose group was elevated to 150 ppmand after 84weeks to 300 ppm. No evidence of carcinogenicity was observed.When azinphos-methyl was fed to mice at 0, 5, 20, or 40 ppm (about 0.79, 3.49, 11.33 (males); 0.98, 4.12, 14.30 (females)) for 2 years, no compound-related toxicity or evidence of cancer occurred .

Environmental Fate

Biological. Mixed cultures of microorganisms obtained from soil, raw sewage, acti vated sludge, and settled sludge were all able to degrade azinphosmethyl. When this dithioate pesticide was incubated in a stirred flask containing a mixed culture for 4 days, the concentration decreased from 99 to 40 mg/L (Barik et al., 1984).Soil. The principal degradation products in soil and by selected soil microorganisms are benzazimide, thiomethylbenzazimide, bis(benzazimidylmethyl)disulfide and anthra nilic acid. Benzazimide is further transformed only by Pseudomonas sp. DSM 50When radiolabeled azinphos-methyl was incubated in soil, 50 and 93% of the applied amount degraded to carbon dioxide after 44 and 197 days, respectively (Engelhardt et al., 1984). The presence of benzamide, salicylic acid and 14CO2 from [carbonyl-14C]- anIn a dry soil (2–3% moisture content), the half-lives were 484, 88 and 32 days at 6, 25 and 40°C, respectively. In a soil containing 50% moisture, the half-lives were much shorter, i.e., 64, 13 and 5 days at 6, 25 and 40°C, respectively (Yaron et al., 1974).Azinphos-methyl will not leach to any great extent in soil (Helling, 1971). Staiff et al. (1975) studied the persistence of azinphos-methyl in a test plot over an 8-year period. At the end of the eighth year, virtually no azinphos-methyl was detected 30 c

Metabolic pathway

In the apple tree, 14C-azinphos methyl is metabolized to a small degree and, by the cell culture, 71% of the applied activity consists of unchanged azinphos methyl and its oxon is identified as a metabolite in a small amount. Two major metabolites are identified in the aqueous phase of the peel extract and in the cell extracts of the cell cultures. The major one is a conjugate of mercaptomethylbenzazimide with 2-(1- glucopyranosyl)propionic acid, and the minor one is monodesmethylazinphos methyl. In rats, following the administration of a single dose of azinphos methyl, the major radioactivity is eliminated in the expired air within 48 h. The metabolites in the urine result from the cleavage of P-S-C and P-O-CH3 bonds yielding O,O-dimethyl phosphorothioic acid together with mercaptomethylbenzamide and mono-O- demethylated azinphos methyl, respectively.

storage

Azinphos methyl only should be handled by trained occupational workers/personnel wearing proper protective clothing. Azinphos methyl should always be stored and transported in clearly labeled impermeable containers under lock and key. Its storage area should be secure from access by unauthorized persons and children. Occupational workers must be properly informed that no food or drink should be stored in the storage areas.

Degradation

Azinphos-methyl is rapidly hydrolysed in alkaline and acidic media. It rapidly photodegrades on soil surfaces and in water (PM). The hydrolysis of [14C-carbonyl]azinphos-methywl as studied in buffered aqueous solution, pH 6-11 and the decomposition products were analysed by 2D TLC co-chromatography and GLC with authenticated standards after seven days incubation. The compound was relatively stable between pH 6 and 9 but at pH 10-11 it was largely decomposed. The decomposition products were identified as 3-methylbenzazimide (2), bis-3-methylbenzazimide disulfide (3), benzazimide (4), azinphos-methyl oxon (5) and anthranilic acid (6). The proportion of the oxon was appreciable at pH 9-10 but at pH 11 it was a minor component of the mixture. When [14C-carbonyl]azinphos-methyl was subjected to elevated temperatures on a glass surface in the dark for seven days it was found to thermally degrade at appreciable rates at 50°C and above. The five degradation products, which had also been found in the hydrolysis experiments, were identified as products of thermal decomposition with the addition that the intermediate 3-(thiomethyl)benzazimide (7) was also characterised as well as the disulfide (3). Degradation was more rapid in heated water than on glass. When [14C-carbonyl]azinphos-methyl was subjected to irradiation as a water suspension or as a thin film by UV light (254 nm), sunlight and red and yellow filtered light (intensities unrecorded) for up to 12 hours the compound was rapidly degraded by the UV light with 95% being decomposed after 60 min. Red or yellow light caused no photolysis and sunlight irradiation of a thin film on glass caused some photodecomposition. Photolysis products identified in the UV-irradiated samples were 3-methylbenzazimide (2), bis-3- methylbenzazimide disulfide (3), benzazimide (4) and anthranilic acid (6) in addition to four water-soluble products which were not identified. Only benzazimide (4) and bis-3-methylbenzazimide disulfide (3) were identified in the sunlight-irradiated sample (Liang and Lichtenstein, 1972).Routes for the hydrolysis, thermal decomposition and photolysis of azinphos-methyl are shown in Scheme 1.

Precautions

Heptachlor decomposes on heating above 160°C, producing toxic fumes including hydro- gen chloride. It reacts with strong oxidants and attacks metal. During use and handling of liquid and powder formulations of heptachlor, occupational workers should wear protec- tive neoprene or PVC gloves, cotton overalls, rubber boots, and a face shield or dust mask. Heptachlor should be kept stored in locked buildings.

InChI:InChI=1/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3

Upstream product

• 24310-40-5 3-(hydroxymethyl)benzotriazin-4(3H)-one 
• 90-16-4 1,2,3-benzotriazin-4(3H)-one 
• 24310-41-6 3-chloromethyl-1,2,3-benzotriazin-4(3H)-one 

Relevant articles and documents

PESTICIDAL COMPOSITIONS

Composition for controlling insects and representatives of the order Acarina, which comprises a combination of variable amounts of one or more compounds of the formula in which A is an unsubstituted or, depending on the possibility of substitution on the ring system, mono- to tetrasubstituted, aromatic or non-aromatic monocyclic or bicyclic heterocyclic radical, in which the substituents of A can be chosen from the group consisting of C1-C3alkyl, C1-C3alkoxy, halogen, halo-C1-C3alkyl, cyclopropyl, halocyclopropyl, C2-C3alkenyl, C2-C3alkynyl, halo-C2-C3alkenyl, halo-C2-C3alkynyl, halo-C1-C3alkoxy, C1-C3alkylthio, Halo-C1-C3alkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro; R is hydrogen, C1-C6alkyl, phenyl-C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl or C2-C6alkynyl; and X is N—NO2 or N—CN, in the free form or in salt form, if appropriate tautomers, in the free form or salt form, and one or more of the compounds (I) to (CLXXXIV) mentioned according to the invention and at least one auxiliary. A method of controlling pests, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compound of the formula (A) for the preparation of the composition, are described.

Macrocyclic plant acaricides

Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.