AZINPHOS-METHYL
- CAS No.
- 86-50-0
- Chemical Name:
- AZINPHOS-METHYL
- Synonyms
- Azinphos;AZIN;Guthion;s-ester;azinphose methyl;1,2,3-Benzotriazin-4(3H)-one, 3-(mercaptomethyl)-, O,O-dimethyl phosphorodithioate;R1582;ACIFON;Carfene;Cotneon
- CBNumber:
- CB0204970
- Molecular Formula:
- C10H12N3O3PS2
- Molecular Weight:
- 317.32
- MOL File:
- 86-50-0.mol
- Modify Date:
- 2024/3/14 15:18:25
| Melting point | 73℃ |
|---|---|
| Boiling point | 421.3±55.0 °C(Predicted) |
| Density | 1.44 g/cm3 (20℃) |
| vapor pressure | 5.0 x 10-7 Pa (20 °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) |
| form | solid |
| color | Crystals or brown, waxy solid |
| Merck | 13,915 |
| BRN | 280476 |
| Exposure limits | NIOSH REL: 0.2 mg/m3; OSHA PEL: TWA 0.2 mg/m3; ACGIH TLV: TWA 0.2 mg/m3. |
| InChIKey | CJJOSEISRRTUQB-UHFFFAOYSA-N |
| LogP | 2.750 |
| CAS DataBase Reference | 86-50-0(CAS DataBase Reference) |
| EPA Substance Registry System | Azinphos-methyl (86-50-0) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS06,GHS09 |
|---|---|
| Signal word | Danger |
| Hazard statements | H300+H330-H311-H317-H410 |
| Precautionary statements | P260-P264-P273-P280-P302+P352+P312-P304+P340+P310 |
| Hazard Codes | T+,N |
| Risk Statements | 24-26/28-43-50/53-28 |
| Safety Statements | 28-36/37-45-60-61 |
| RIDADR | 2783 |
| OEB | C |
| OEL | TWA: 0.2 mg/m3 [skin] |
| WGK Germany | 3 |
| RTECS | TE1925000 |
| HazardClass | 6.1(a) |
| PackingGroup | II |
| Toxicity | LD50 in female rats (mg/kg): 11 orally; 220 dermally (Gaines) |
| IDLA | 10 mg/m3 |
AZINPHOS-METHYL Chemical Properties,Uses,Production
Chemical Properties
Pure azinphos-methyl is a colorless-to-white odorless crystalline solid. Azinphos-methyl is subject to hydrolysis and decomposes with gas evolution at elevated temperatures.Soluble in methanol, ethanol, propylene glycol, xylene, and other organic solvents; slightly soluble in water (33 mg/L).
Uses
Azinphos-methyl is used to control a wide range of both sucking and chewing insects and spider mites in a wide range of crops.
Definition
ChEBI: A member of the class of benzotriazines that is 1,2,3-benzotriazine substituted by an oxo group at position 4 and a [(dimethoxyphosphorothioyl)sulfanyl]methyl group at position 3.
General Description
Azinphos methyl is a colorless brown, waxy or white crystalline solid dissolved in a liquid carrier. AZINPHOS-METHYL is used as a pesticide. AZINPHOS-METHYL is added to water to create a water emulsifiable liquid. AZINPHOS-METHYL is toxic by inhalation, skin absorption, and/or ingestion. AZINPHOS-METHYL is heavier than and insoluble in water.
Technical-grade guthion is a cream to yellowbrown granular solid. Guthion is poorly soluble in water. Pure guthion is a colourless to white odourless crystalline solid. Technical-grade guthion is a cream to yellow-brown granular solid.
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
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.
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.
Agricultural Uses
Insecticide, Acaricide: Not approved for use in EU countries. Azinphosmethyl liquids with a concentration greater than 13.5% are classified as a U.S. Restricted Use Pesticides (RUP) Insecticide used to control certain chewing and sucking insects in forestry settings, on fruits and fruit trees, vines, nuts, vegetables, cereals, maize, cotton, ornamentals, soy beans, tobacco, rice, coffee, sugar cane, and other crops. Also used as an intermediate in the manufacture, formulation and application of insecticides and acaricides. There are 31 global suppliers.
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 50
When 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]- an
In 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.
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.
AZINPHOS-METHYL Preparation Products And Raw materials
Raw materials
Preparation Products
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