Diazinon
- Iupac Name：diethoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane
- CAS No.: 333-41-5
- Molecular Weight：304.345
- Modify Date.: 2022-11-29 10:34
- Introduction: Diazinon is a non-systemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon functions as the inhibitor of acetylcholinesterase (AChE), which breaks down the neurotransmitter acetylcholine (ACh) into [choline] and an acetate group. The inhibition of the AChE causes an abnormal accumulation of ACh in the synaptic cleft. However, recent studies have shown that diazinon and other kinds of organophosphate can cause neural toxicity through causing oxidative stress in the neural cells.
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1. Names and Identifiers
- 1.1 Name
- Diazinon
- 1.2 Synonyms
AG-500 Anti Antigal (VAN) Antlak basudin Bazudin Dazzel Diazinon AG500 Dicid dimpylate dyzol EINECS 206-373-8 Exodin G 301 MFCD00036204 O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidinyl) phosphorothioate O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioate O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) thiophosphate O,O-Diethyl O-(2-isopropyl-6-methylpyrimidin-4-yl) phosphorothioate O,O-diethyl O-[6-methyl-2-(1-methylethyl)-4-pyrimidinyl] phosphorothioate O,O-diethyl O-[6-methyl-2-(propan-2-yl)pyrimidin-4-yl] phosphorothioate O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate O,O-Diethyl-O-(2-isopropyl-6-methyl-4-pyrimidinyl)thiophosphat O,O-diethylO-(2-isopropyl-6-methyl-4-pyrimidinyl)thiophosphate O,O-diethylO-(2-isopropyl-6-methyl-4-pyrimidinyl)-thiophosphate O,O-diethylO-(2-isopropyl-6-methyl-4-pyrimidinyl)thio-phosphate O,O-Diethyl-O-(2-isopropyl-6-methylpyrimidin-4-yl)thiophosphat O,O-DIETHYL-O-[2-ISOPROPYL-4-METHYL-6-PYRIMIDYL]PHOSPHOROTHIOATE o,o-diethylo-6-methyl-2-isopropyl-4-pyrimidinylphosphorothioate o,o-dietil-o-(2-isopropil-4-metil-pirimidin-6-il)-monotiofosfato O-2-Isopropyl-4-methylpyrimidyl-O,O-diethyl phosphorothioate o-2-isopropyl-4-methylpyrimidyl-o,o-diethylphosphorothioate Phosphorothioic acid, O,O-diethyl O-[6-methyl-2- (1-methylethyl)-4-pyrimidinyl] ester Phosphorothioic acid, O,O-diethyl O-[6-methyl-2-(1-methylethyl)-4-pyrimidinyl] ester pt265 Thiophosphate de O,O-diéthyle et de O-(2-isopropyl-6-méthyl-4-pyrimidinyle)
- 1.3 CAS No.
- 333-41-5
- 1.4 CID
- 3017
- 1.5 EINECS(EC#)
- 206-373-8
- 1.6 Molecular Formula
- C12H21N2O3PS (isomer)
- 1.7 Inchi
- InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3
- 1.8 InChkey
- FHIVAFMUCKRCQO-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C
- 1.10 Isomers Smiles
- CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C
2. Properties
- 2.1 Density
- 1.117
- 2.1 Melting point
- >120℃ (dec.)
- 2.1 Boiling point
- < 25 °C
- 2.1 Refractive index
- 1.595
- 2.1 Flash Point
- 82 to 105° F (commercial solutions) (NTP, 1992)
- 2.1 Precise Quality
- 304.10100
- 2.1 PSA
- 95.37000
- 2.1 logP
- 4.23530
- 2.1 Solubility
- Slightly soluble. 0.004 g/100 mL
- 2.2 AnalyticLaboratory Methods
- Method: NIOSH 5600, Issue 1; Procedure: gas chromatography, flame photometric detection; Analyte: diazinon;; Matrix: air; Detection Limit: 0.04 ug/sample.
- 2.3 Appearance
- Liquid; light to dark brown. Sinks in water. Commercial solutions can contain ethanol/xylene/acetone with a flash point in the range 82-105° F.
- 2.4 Autoignition Temperature
- > 400 deg C. /Diazinon 50W/
- 2.5 Carcinogenicity
- Among 23,106 male applicatorsparticipating in the Agricultural Health Study whoreported using diazinon, there was an increased risk withexposure to diazinon for lung cancer, leukemia, and allcancer sites combined, although the small number of casesobserved makes these estimates unreliable .
- 2.6 Color/Form
- Colorless liquid
- 2.7 Decomposition
- When heated to decomposition it emits very toxic fumes of /phosphorus oxides, sulfur oxides, and nitrogen oxides/.
- 2.8 HenrysLawConstant
- 1.13e-07 atm-m3/mole
- 2.9 Odor
- Faint ester-like odor
- 2.10 Physical
- Liquid; light to dark brown. Sinks in water;. Commercial solutions can contain ethanol;/xylene/acetone; with a flash point in the range 82-105° F.
- 2.11 pKa
- 1.21±0.30(Predicted)
- 2.12 Water Solubility
- H2O: Slightly soluble . 0.004 g/100 mL
- 2.13 Spectral Properties
- Index of refraction: 1.4978-1.4981 @ 20 deg C/D
Intense mass spectral peaks: 179 m/z (100%), 137 m/z (94%), 152 m/z (85%), 304 m/z (64%)
MASS: 4834 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
- 2.14 Stability
- SENSITIVE TO OXIDN ABOVE 100 DEG C; DEGRADATION ABOVE 120 DEG C
- 2.15 StorageTemp
- APPROX 4°C
3. Use and Manufacturing
- 3.1 Agricultural Uses
- Insecticide, Acaricide: Diazinon is the most widely used pesticide byhomeowners on lawns, and is one of the most widely usedpesticide ingredients for application around the home andin gardens. It is used to control insects and grub worms.It is a nonsystemic organophosphate insecticide used tocontrol cockroaches, silverfish, ants, and fleas in residential,non-food buildings. Bait is used to control scavengeryellow jackets in the western U.S. It is used on homegardens and farms to control a wide variety of suckingand leaf-eating insects. It is used on rice, fruit trees,sugarcane, corn, tobacco, potatoes and on horticulturalplants, and is also an ingredient in pest strips. Diazinonhas veterinary uses against fleas and ticks. It is availablein dust, granules, seed dressings, wettable powder, andemulsifiable solution formulations. In 1988, there were500 different products containing diazinon on the market,and used in such products as agricultural sprays andgranules, animal ear tags, household sprays and dust andveterinary products. Not approved for use in EU countries.A U.S. EPA restricted Use Pesticide (RUP). TheU.S. EPA initiated a program to phase out all non-agriculturaluses of diazinon commencing in March, 2001. Manycommercial outdoor uses of diazinon have been canceledor restricted to licensed pesticide applicators because ofits known toxicity to birds and aquatic life. Diazinon ishighly toxic to bees and very highly toxic to birds, fishand aquatic invertebrates. Diazinon was canceled for useon golf courses and sod farms in 1988 because of its highrisk to birds
- 3.2 Definition
- ChEBI: A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.
- 3.3 Environmental Fate
- Biological. Sethunathan and Yoshida (1973a) isolated a Flavobacterium sp. (ATCC 27551) from rice paddy water that metabolized diazinon as the sole carbon source. Diazinon was readily hydrolyzed to 2-isopropyl-4-methyl-6-hydroxypyrimidine under aerobic conditions but less rapidly under anaerobic conditions. This bacterium as well as enrichment cultures isolated from a diazinon-treated rice field mineralized the hydrolysis product to carbon dioxide (Sethunathan and Pathak, 1971; Sethunathan and Yoshida, 1973). Rosenberg and Alexander (1979) demonstrated that two strains of Pseudomonas grew on diazinon and produced diethyl phosphorothioate as the major end product. The rate of microbial degradation increased in the presence of an enzyme (parathion hydrolase), produced by a mixed culture of Pseudomonas sp. (Honeycutt et al., 1984).Soil. Hydrolyzes in soil to 2-isopropyl-4-methyl-2-hydroxypyrimidine, diethylphosphorothioic acid, carbon dioxide (Getzin, 1967; Lichtenstein et al., 1968; Sethunathan and Yoshida, 1969; Sethunathan and Pathak, 1972; Bartsch, 1974; Wolfe et al., 1976; Somasundaram and Coats, 1991) and tetraethylpyrophosphate (Paris and Lewis, 1973). The half-life of diazinon in soil was observed to be inversely proportional to temperature and soil moisture content (Getzin, 1968). Seven months after diazinon was applied on a sandy loam (2 kg/ha), only 1% of the total applied amount remained and 10% was detected in a peat loam (Suett, 1971).The reported half-life in soil is 32 days (Jury et al., 1987). Reported half-lives in soil following incubation of 10 ppm diazinon in sterile sand loam, sterile organic soil, nonsterile sandy loam and nonsterile organic soil are 12.5, 6.5, <1 and 2 weeks, respectively (Miles et al., 1979). The reported half-life of diazinon in sterile soil at pH 4.7 was 43.8 days (Sethunathan and MacRae, 1969). Major metabolites identified were diethyl thiophosphoric acid, 2-isopropyl-4-methyl-6-hydroxypyrimidine and carbon dioxide (Konrad et al., 1967). When soil is sterilized, the persistence of diazinon increased more so than changes in soil moisture, soil type or rate of application (Bro-Rasmussen et al., 1968). The halflives for diazinon in flooded soil incubated in the laboratory ranged from 4 to 17 days with an average half-life of 10 days (Sethunathan and MacRae, 1969; Sethunathan and Yoshida, 1969; Laanio et al., 1972). The mineralization half-life for diazinon in soil was 5.1 years (Sethunathan and MacRae, 1969; Sethunathan and Yoshida, 1969).The half-lives of diazinon in a sandy loam, clay loam and an organic amended soil under nonsterile conditions were 66–1,496, 49–1,121 and 14–194 days, respectively, while under sterile conditions the half-lives were 57–1,634, 46–1,550 and 14–226 days, respectively (Schoen and Winterlin, 1987).In a silt loam and sandy loam, reported Rf values were 0.86 and 0.88, respectively (Sharma et al., 1986).Surface Water. In estuarine water, the half-life of diazinon ranged from 8.2 to 10.2 days (Lacorte et al., 1995).Groundwater. According to the U.S. EPA (1986) diazinon has a high potential to leach to groundwater.Plant. Diazinon was rapidly absorbed by and translocated in rice plants. Metabolites identified in both rice plants and a paddy soil were 2-isopropyl-4-methyl-6-hydroxypyrimidine (hydrolysis product), 2-(1¢-hydroxy-1¢-methyl)ethyl-4-methyl-6-hydroxypyrimidine and other polar compounds (Laanio et al., 1972). Oxidizes in plants to diazoxon (Ralls et al., 1966; Laanio et al., 1972; Wolfe et al., 1976) although 2-isopropyl-4-methyl- 6-pyrimidin-6-ol was identified in bean plants (Kansouh and Hopkins, 1968) and as a hydrolysis product in soil (Somasundaram et al., 1991) and water (Suffet et al., 1967). Five days after spraying, pyrimidine ring-labeled 14C-diazinon was oxidized to oxodiazinon which was then hydrolyzed to 2-isopropyl-4-methylpyrimidin-6-ol which in turn, was further metabolized to carbon dioxide (Ralls et al., 1966). Diazinon was transformed in field-sprayed kale plants to form hydroxydiazinon {O,O-diethyl-O-[2-(2¢-hydroxy-2¢-propyl)- 4-methyl-6-pyrimidinyl] phosphorothioate} which was not previously reported (Pardue et al., 1970).
- 3.4 General Description
- Diazinon is available in the form of a colourless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agriculture and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, and crops and household pests like flies, fleas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes such as nitrogen oxides, phosphorus oxides, and sulphur oxides. It reacts with strong acids and alkalis with possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classified as a RUP. Depending on the type of formulation, diazinon is classified as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.
- 3.5 GHS Classification
- Signal: Warning
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
Precautionary Statement Codes
P264, P270, P273, P301+P312, P330, P391, and P501
- 3.6 Methods of Manufacturing
- Methanol, hydrogen chloride and isobutyronitrile are reacted to form the corresponding imidate hydrochloride; treated with ammonia and converted into the corresponding amidine.?Then, under basic conditions, amidine is condensed with ethyl acetoacetate to obtain pyrimidinol (4-hydroxy-2-isopropyl-6-methylpyrimidine).?Pyrimidinol is heated to reflux in the presence of sodium carbonate in benzene or toluene, diethylthiophosphoryl chloride and copper nitrate are added, and condensation is obtained to obtain diazinon.
- 3.7 Potential Exposure
- roducers, formulators and applicatorsof this nonsystemic pesticide and acaricide. Diazinon isused in the United States on a wide variety of agriculturalcrops, ornamentals, domestic animals; lawns and gardens;and household pests.
- 3.8 Shipping
- UN2783 Organophosphorus pesticides, solid,toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- 3.9 Usage
- Insecticide.
- 3.10 Waste Disposal
- Diazinon is hydrolyzed inacid media about 12 times as rapidly as parathion, andat about the same rate as parathion in alkaline media. Inexcess water this compound yields diethylthiophosphoricacid and 2-isopropyl-4-methyl-6-hydroxypyrimidine. Withinsufficient water, highly toxic tetraethyl monothiopyropho-sphate is formed. Therefore, incineration would be a prefer-able ultimate disposal method with caustic scrubbing ofthe incinerator effluent. In accordance with 40CFR165,follow recommendations for the disposal of pesticides andpesticide containers. Must be disposed properly by follow-ing package label directions or by contacting your local orfederal environmental control agency, or by contactingyour regional EPA office.
4. Safety and Handling
- 4.1 Symbol
- GHS02;GHS07;GHS09;
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- DANGER
- 4.1 Risk Statements
- R22;R50/53
- 4.1 Safety Statements
- S24/25;S60;S61
- 4.1 Packing Group
- III
- 4.1 Octanol/Water Partition Coefficient
- log Kow = 3.81
- 4.2 Fire Hazard
- Not flammable. POISONOUS GASES ARE PRODUCED WHEN HEATED. Oxides of sulfur and of phosphorus are generated in fires.
- 4.3 Other Preventative Measures
- The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed or replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
If material not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
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.
- 4.4 Hazard Class
- 6.1(b)
- 4.4 Hazard Declaration
- H225; H302; H312; H319; H332; H411
- 4.4 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./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount.
- 4.5 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Hydrolysis: Diazinon is hydrolyzed in acid media. In excess water this cmpd yields diethylthiophosphoric acid and 2-isopropyl-4-methyl-6-hydroxypyrimidine. With insufficient water, highly toxic tetraethyl monothiopyrophosphate is formed.
Alkaline hydrolysis leads to complete degradation. The alkaline salt of diethylthiophosphoric acid and the 2-isopropyl-4-methyl-6-hydroxypyrimidine formed are considerably less toxic than diazinon. Acid hydrolysis: Complete degradation in large excess of water, same hydrolysis products are obtained as in alkaline hydrolysis. However, highly toxic tetraethyl dithio- and thiopyrophosphates have been found with insufficient water in acid medium. Oxidation leads to complete degradation but the diazoxon formed is equally toxic. For the decontamination of diazinon containers, the triple rinse and drain procedure developed by the National Agricultural Chemicals Association (NACA) is recommended. "Triple rinse" means the flushing of containers three times, each time using a volume of the normal diluent equal to approx 10% of the container's capacity and adding the rinse liquid to the spray mixture or disposing of it by a method prescribed for disposing of the pesticide. The use of a rinse soln containing caustic soda and detergent may also be considered. Recommendable methods: Hydrolysis & incineration. Peer-review: Large amt should be incinerated in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
The following wastewater treatment technologies have been investigated for diazinon: Concentration process: Biological treatment.
The following wastewater treatment technologies have been investigated for diazinon: Concentration process: Reverse osmosis.
- 4.6 DOT Emergency Guidelines
- /GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire: CAUTION: All these products have a very low flash point. Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Spill or Leak: Fully encapsulating, vapor protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Small spills: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth 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. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading . Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth 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. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Organophosphorus pesticide, liquid, poisonous; Organophosphorus pesticide, liquid, toxic; Organophosphorus pesticide, solid, poisonous; Organophosphorus pesticide, solid, toxic/
- 4.7 RIDADR
- UN 2783/2810
- 4.7 Fire Fighting Procedures
- If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.)
- 4.8 FirePotential
- PRACTICALLY NONFLAMMABLE.
- 4.9 Safety Profile
- Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Mildly toxic by inhalation. Human systemic effects by ingestion: changes in motor activity, muscle weakness, and sweating. Experimental teratogenic and reproductive effects. A skin and severe eye irritant. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, POx, and SOx.
- 4.10 Caution Statement
- P201-P280-P301 + P312 + P330-P308 + P313
- 4.10 Formulations/Preparations
- BASUDIN 5G (GRANULES 50 G AI/KG); BASUDIN 10; BASUDIN WP (400 G AI/KG) SEED DRESSING- BASUDIN 50SD. FOR VETERINARY USE NEOCIDOL 60, NUCIDOL 60- EMULSIFIABLE CONCENTRATE CONTAINING 60% ACTIVE INGREDIENT NEUCIDOL 40 WP.
Dust; emulsifiable and oil solutions; granules; seed dressings; ULV; wettable powder.
0.5% /FOR/ TOPICAL APPLICATION; IN PVC PELLETS.
Granule, wettable powder, emulsifiable concentrate, dustable powder, dry seed treatment, smoke tablet, capsule suspension, cold fogging concentrate
- 4.11 Incompatibilities
- Reaction with nitrosating agents (e.g.,nitrites, nitrous gases, nitrous acid) capable of releasing carci-nogenic nitrosamines. Hydrolyzes slowly in water and diluteacid. Reacts with strong acids and alkalis with possible forma-tion of highly toxic tetraethyl thiopyrophosphates.Incompatible with copper-containing compounds. Contactwith oxidizers may cause the release of phosphorous oxides.Contact with strong reducing agents, such as hydrides; maycause the formation of flammable and toxic phosphine gas.
- 4.12 WGK Germany
- 3
- 4.12 RTECS
- TF3325000
- 4.12 Protective Equipment and Clothing
- Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
- 4.13 Reactivities and Incompatibilities
- REACTS WITH STRONG ACID & ALKALI.
Strong acids & alkalis, copper containing compounds [Note: Hydrolyzes slowly in water & dilute acid].
- 4.14 Safety
-
Safety Information of Diazinon (CAS NO.333-41-5):
Hazard Codes: Xn
;N
Risk Statements: R22;R50/53???
R22:Harmful if swallowed.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: S24/25;S60;S61?
S24:Avoid contact with skin.?
S25:Avoid contact with eyes.?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
- 4.15 Specification
-
?Diazinon , its CAS NO. is 333-41-5, the synonyms are O,O-Diethyl O-2-isopropyl-4-methyl-6-pyrimidyl thiophosphate ; ?O,O-Diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate .
- 4.16 Toxicity
- Oral-rat LD50: 66 mg/kg; Oral-Mouse LD50: 17 mg/kg
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P273 Avoid release to the environment. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P391 Collect spillage. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
333-41-5Total: 3 Synthesis Route
-
|
|
 |
|
Literatures:
Zhurnal Obshchei Khimii, , vol. 26, p. 808; engl. Ausg. S. 925
Zeitschrift fuer Analytische Chemie, , vol. 147, p. 173,182
DE910652 , ;
Organiceskie Insektofungicidy i Gerbicidy S. 108, 111; C.A. 1961 3600
Bulletin de la Societe Chimique de France, , p. 459
Trudy 1. Konf. fosfororg. Soedin. KazanChem.Abstr., , p. 50,51
Trudy 1. Konf. fosfororg. Soedin. KazanChem.Abstr., , p. 393
Journal of Organic Chemistry, , vol. 21, p. 685
Chimia, , vol. 8, p. 221,223
Yield: null
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-
-
9. Other Information
- 9.0 Merck
- 13,3019
- 9.1 BRN
- 273790
- 9.2 Description
- Diazinon is a non-systemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon functions as the inhibitor of acetylcholinesterase (AChE), which breaks down the neurotransmitter acetylcholine (ACh) into [choline] and an acetate group. The inhibition of the AChE causes an abnormal accumulation of ACh in the synaptic cleft. However, recent studies have shown that diazinon and other kinds of organophosphate can cause neural toxicity through causing oxidative stress in the neural cells.
- 9.3 Description
- Diazinon is a broad-spectrum insecticide that is active against approximately 120 species of insects and pests.1 It is metabolized into the cholinesterase inhibitors monothionotetraethyl pyrophosphate, dithionotetraethyl pyrophosphate, and triethylthionophosphate in vivo, which induce vomiting, fasciculation with muscular twitching, paralysis, and death (LD50 = 125 mg/kg) in rats. Diazinon induces formation of capsular adhesion in the kidneys and ulcer formation in the duodenum of dogs as well as mucosal erosion and serosal seepage in the intestines of mini pigs. Formulations containing diazinon were previously used as agricultural pesticides.
- 9.4 Chemical Properties
- Diazinon is available as a colorless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agricultural and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, crops pests, and household pests like fl ies, fl eas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes, such as nitrogen oxides, phosphorous oxides, and sulfur oxides. It reacts with strong acids and alkalis with the possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classifi ed as an RUP. Depending on the type of formulation, diazinon is classifi ed as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.
- 9.5 Chemical Properties
- Diazinon is a combustible, colorless, oily liquid. Faint amine odor. Technical grade is pale to dark brown. Commercial formulations may use carrier solvents which can change the physical properties listed here.
- 9.6 Uses
- Insecticide.
- 9.7 Uses
- insecticide, cholinesterase inhibitor
- 9.8 Uses
- A cholinesterase inhibitor; a nonsystemic organophosphate insecticide.
- 9.9 Uses
- Nonsystemic contact insecticide used against flies, aphids and spider mites in soil, fruit, vegetables and ornamentals.
- 9.10 Uses
- Diazinon is used to control a wide range of sucking and chewing insects and mites in a very wide range of crops and is also used as a veterinary ectoparasiticide.
- 9.11 Definition
- ChEBI: A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.
- 9.12 General Description
- Diazinon is available in the form of a colourless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agriculture and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, and crops and household pests like flies, fleas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes such as nitrogen oxides, phosphorus oxides, and sulphur oxides. It reacts with strong acids and alkalis with possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classified as a RUP. Depending on the type of formulation, diazinon is classified as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.
- 9.13 Air & Water Reactions
- The neat compound is susceptible to oxidation and should be protected from prolonged exposure to air . Insoluble in water.
- 9.14 Health Hazard
- LIQUID: POISONOUS IF SWALLOWED. Irritating to skin and eyes.
- 9.15 Health Hazard
- Humans are exposed to diazinon during manufacture and professional applications. Diazinon causes poisoning with symptoms such as headache, dizziness, nausea, weakness, feelings of anxiety, vomiting, pupillary constriction, convulsions, respiratory distress or labored breathing, unconsciousness, muscle cramp, excessive salivation, respiratory failure, and coma.
- 9.16 Health Hazard
- Cholinesterase inhibitor; moderately toxic byingestion and skin absorption; ingestion ofapproximately large quantities of 10–15 gcan produce cholinergic effects in adulthuman; poisoning symptoms include headache, dizziness, weakness, blurred vision,pinpoint pupils, salivation, muscle spasms,vomiting abdominal pain, and respiratorydepression; LD50 values in experimentalanimals show wide variation.
LD50 oral (rat): within the range 100–300mg/kg
LD50 oral (guinea pig): 250 mg/kg.
- 9.17 Fire Hazard
- Not flammable. POISONOUS GASES ARE PRODUCED WHEN HEATED. Oxides of sulfur and of phosphorus are generated in fires.
- 9.18 Agricultural Uses
- Insecticide, Acaricide: Diazinon is the most widely used pesticide by homeowners on lawns, and is one of the most widely used pesticide ingredients for application around the home and in gardens. It is used to control insects and grub worms. It is a nonsystemic organophosphate insecticide used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Bait is used to control scavenger yellow jackets in the western U.S. It is used on home gardens and farms to control a wide variety of sucking and leaf-eating insects. It is used on rice, fruit trees, sugarcane, corn, tobacco, potatoes and on horticultural plants, and is also an ingredient in pest strips. Diazinon has veterinary uses against fleas and ticks. It is available in dust, granules, seed dressings, wettable powder, and emulsifiable solution formulations. In 1988, there were 500 different products containing diazinon on the market, and used in such products as agricultural sprays and granules, animal ear tags, household sprays and dust and veterinary products. Not approved for use in EU countries. A U.S. EPA restricted Use Pesticide (RUP). The U.S. EPA initiated a program to phase out all non-agricultural uses of diazinon commencing in March, 2001. Many commercial outdoor uses of diazinon have been canceled or restricted to licensed pesticide applicators because of its known toxicity to birds and aquatic life. Diazinon is highly toxic to bees and very highly toxic to birds, fish and aquatic invertebrates. Diazinon was canceled for use on golf courses and sod farms in 1988 because of its high risk to birds
- 9.19 Trade name
- AG-500?; AI3-19507?; ALFA-TOX?[C]; ANTIGAL?; ANTLAK?; BASUDIN?; BAZUDEN?; CASWELL No. 342?; DACUTOX?; DASSITOX?; DAZZEL?; DIAGRAN?; DIANON?; DIATERR-FOS?; DIAZAJET?; DIAZATOL?; DIAZIDE?; DIAZINON AG 500 WBC?; DIAZINONE?; DIAZITOL?; DIAZOL?; DICID?; DIMPYLATE?; DIPOFENE?; DIZIKTOL?; DIZINON?[C]; DRAWIZON?; DYMET?; DYZOL?); D.Z.N.?; EXODIN?; FEZUDIN?; FLYTROL?; G 301?; G-24480?; GALESAN?; GARDENTOX?; GEIGY 24480?; KAYAZINON?; KAYAZOL?; NEOCIDOL? (OIL); NEOCIDOL?; NIPSAN?; NUCIDOL?; OLEODIAZINON?; ROOT GUARD; SAROLEX?[C]; SPECTRACIDE?; SROLEX?; SUZON?
- 9.20 Safety Profile
- Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Mildly toxic by inhalation. Human systemic effects by ingestion: changes in motor activity, muscle weakness, and sweating. Experimental teratogenic and reproductive effects. A skin and severe eye irritant. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, POx, and SOx.
- 9.21 Potential Exposure
- roducers, formulators and applicators of this nonsystemic pesticide and acaricide. Diazinon is used in the United States on a wide variety of agricultural crops, ornamentals, domestic animals; lawns and gardens; and household pests.
- 9.22 Carcinogenicity
- Among 23,106 male applicators participating in the Agricultural Health Study who reported using diazinon, there was an increased risk with exposure to diazinon for lung cancer, leukemia, and all cancer sites combined, although the small number of cases observed makes these estimates unreliable .
- 9.23 Environmental Fate
- Biological. Sethunathan and Yoshida (1973a) isolated a Flavobacterium sp. (ATCC 27551) from rice paddy water that metabolized diazinon as the sole carbon source. Diazinon was readily hydrolyzed to 2-isopropyl-4-methyl-6-hydroxypyrimidine under aerobic conditions but less rapidly under anaerobic conditions. This bacterium as well as enrichment cultures isolated from a diazinon-treated rice field mineralized the hydrolysis product to carbon dioxide (Sethunathan and Pathak, 1971; Sethunathan and Yoshida, 1973). Rosenberg and Alexander (1979) demonstrated that two strains of Pseudomonas grew on diazinon and produced diethyl phosphorothioate as the major end product. The rate of microbial degradation increased in the presence of an enzyme (parathion hydrolase), produced by a mixed culture of Pseudomonas sp. (Honeycutt et al., 1984).
Soil. Hydrolyzes in soil to 2-isopropyl-4-methyl-2-hydroxypyrimidine, diethylphosphorothioic acid, carbon dioxide (Getzin, 1967; Lichtenstein et al., 1968; Sethunathan and Yoshida, 1969; Sethunathan and Pathak, 1972; Bartsch, 1974; Wolfe et al., 1976; Somasundaram and Coats, 1991) and tetraethylpyrophosphate (Paris and Lewis, 1973). The half-life of diazinon in soil was observed to be inversely proportional to temperature and soil moisture content (Getzin, 1968). Seven months after diazinon was applied on a sandy loam (2 kg/ha), only 1% of the total applied amount remained and 10% was detected in a peat loam (Suett, 1971).
The reported half-life in soil is 32 days (Jury et al., 1987). Reported half-lives in soil following incubation of 10 ppm diazinon in sterile sand loam, sterile organic soil, nonsterile sandy loam and nonsterile organic soil are 12.5, 6.5, <1 and 2 weeks, respectively (Miles et al., 1979). The reported half-life of diazinon in sterile soil at pH 4.7 was 43.8 days (Sethunathan and MacRae, 1969). Major metabolites identified were diethyl thiophosphoric acid, 2-isopropyl-4-methyl-6-hydroxypyrimidine and carbon dioxide (Konrad et al., 1967). When soil is sterilized, the persistence of diazinon increased more so than changes in soil moisture, soil type or rate of application (Bro-Rasmussen et al., 1968). The halflives for diazinon in flooded soil incubated in the laboratory ranged from 4 to 17 days with an average half-life of 10 days (Sethunathan and MacRae, 1969; Sethunathan and Yoshida, 1969; Laanio et al., 1972). The mineralization half-life for diazinon in soil was 5.1 years (Sethunathan and MacRae, 1969; Sethunathan and Yoshida, 1969).
The half-lives of diazinon in a sandy loam, clay loam and an organic amended soil under nonsterile conditions were 66–1,496, 49–1,121 and 14–194 days, respectively, while under sterile conditions the half-lives were 57–1,634, 46–1,550 and 14–226 days, respectively (Schoen and Winterlin, 1987).
In a silt loam and sandy loam, reported Rf values were 0.86 and 0.88, respectively (Sharma et al., 1986).
Surface Water. In estuarine water, the half-life of diazinon ranged from 8.2 to 10.2 days (Lacorte et al., 1995).
Groundwater. According to the U.S. EPA (1986) diazinon has a high potential to leach to groundwater.
Plant. Diazinon was rapidly absorbed by and translocated in rice plants. Metabolites identified in both rice plants and a paddy soil were 2-isopropyl-4-methyl-6-hydroxypyrimidine (hydrolysis product), 2-(1￠-hydroxy-1￠-methyl)ethyl-4-methyl-6-hydroxypyrimidine and other polar compounds (Laanio et al., 1972). Oxidizes in plants to diazoxon (Ralls et al., 1966; Laanio et al., 1972; Wolfe et al., 1976) although 2-isopropyl-4-methyl- 6-pyrimidin-6-ol was identified in bean plants (Kansouh and Hopkins, 1968) and as a hydrolysis product in soil (Somasundaram et al., 1991) and water (Suffet et al., 1967). Five days after spraying, pyrimidine ring-labeled 14C-diazinon was oxidized to oxodiazinon which was then hydrolyzed to 2-isopropyl-4-methylpyrimidin-6-ol which in turn, was further metabolized to carbon dioxide (Ralls et al., 1966). Diazinon was transformed in field-sprayed kale plants to form hydroxydiazinon {O,O-diethyl-O-[2-(2￠-hydroxy-2￠-propyl)- 4-methyl-6-pyrimidinyl] phosphorothioate} which was not previously reported (Pardue et al., 1970).
- 9.24 Metabolic pathway
- The main route of diazinon metabolism in soil, plants and animals is through cleavage of the P-O-pyrimidine group to yield 2-isopropyl-4- methyl-6-hydroxypyrimidine. As with most other phosphorothioates, loss of the pyrimidinyl function in mammalian metabolism probably occurs either through oxidative desulfuration of the thiono group, catalysed by microsomal mixed function oxidases, to give diazoxon followed by hydrolysis catalysed by an A-esterase, or via an oxidative mechanism catalysed by a mixed function oxidase acting directly on diazinon. In the first case the second product is diethyl phosphate and in the second, diethyl phosphorothioate (Yang et al., 1971). Further metabolism then leads to hydroxylation of the methyl and isopropyl groups on the pyrimidine ring. This oxidative metabolism may the act on the pyrimidinol, diazoxon or diazinon itself, the last of which seems to be important in mammalian and avian liver and gives rise to metabolites which still have anticholinesterase or latent anticholinesterase activity.
- 9.25 Metabolism
- The main biodegradation pathway in mammals, plants, and soils is pyrimidinyl ester bond cleavage; the principal metabolites are diethyl phosphorothioate and diethyl phosphate. Degradation in the environment involves oxidation to diazoxon and hydrolysis.
- 9.26 Shipping
- UN2783 Organophosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- 9.27 Toxicity evaluation
- The acute oral LD50 for rats and mice are 1250 and 80–135 mg/kg. Inhalation LC50 (4 h) for rats is >2330 mg/m3 air. NOEL (2 yr) for rats is 0.06 mg/kg/d.
- 9.28 Degradation
- Diazinon(1) is stable at neutral pH but is slowly hydrolysed in alkaline solutions and rapidly at acidic pH values (PM). Hydrolysis products were identified as the pyrimidinol (2) and diethyl phosphorothioate (3) (PSD, 1991).
When diazinon was dissolved in a water/soil suspension and irradiated with UV light, Mansour et al. (1997) demonstrated that one of the products was iso-diazinon (4) formed via a thiono-thiolo rearrangement (see Scheme 1).
- 9.29 Incompatibilities
- Reaction with nitrosating agents (e.g., nitrites, nitrous gases, nitrous acid) capable of releasing carci- nogenic nitrosamines. Hydrolyzes slowly in water and dilute acid. Reacts with strong acids and alkalis with possible forma- tion of highly toxic tetraethyl thiopyrophosphates. Incompatible with copper-containing compounds. Contact with oxidizers may cause the release of phosphorous oxides. Contact with strong reducing agents, such as hydrides; may cause the formation of flammable and toxic phosphine gas.
- 9.30 Waste Disposal
- Diazinon is hydrolyzed in acid media about 12 times as rapidly as parathion, and at about the same rate as parathion in alkaline media. In excess water this compound yields diethylthiophosphoric acid and 2-isopropyl-4-methyl-6-hydroxypyrimidine. With insufficient water, highly toxic tetraethyl monothiopyropho- sphate is formed. Therefore, incineration would be a prefer- able ultimate disposal method with caustic scrubbing of the incinerator effluent . In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by follow- ing package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
- 9.31 Precautions
- Workers should avoid eye contact with diazinon, wear chemical safety glasses or goggles, protective clothing or equipment, wear waterproof boots, long-sleeved shirts, long pants, and a hat. Workers should avoid contamination of food and feed, wash thoroughly after handling and before eating or smoking. In fact, occupational workers should avoid eating, drinking, or smoking in areas of work with the chemical.
- 9.32 References
- Uner, N, et al. "Effects of diazinon on acetylcholinesterase activity and lipid peroxidation in the brain of Oreochromis niloticus." Environmental Toxicology & Pharmacology 21.3(2006):241.
Shishido, Takashi, K. Usui, and J. I. Fukami. "Oxidative metabolism of diazinon by microsomes from rat liver and cockroach fat body." Pesticide Biochemistry & Physiology 2.1(1972):27-38.
Giordano, G, et al. "Organophosphorus insecticides chlorpyrifos and diazinon and oxidative stress in neuronal cells in a genetic model of glutathione deficiency." Toxicology & Applied Pharmacology 219.2-3(2007):181.
- 9.33 Storage Conditions
- Methanol, hydrogen chloride and isobutyronitrile are reacted to form the corresponding imidate hydrochloride; treated with ammonia and converted into the corresponding amidine.?Then, under basic conditions, amidine is condensed with ethyl acetoacetate to obtain pyrimidinol (4-hydroxy-2-isopropyl-6-methylpyrimidine).?Pyrimidinol is heated to reflux in the presence of sodium carbonate in benzene or toluene, diethylthiophosphoryl chloride and copper nitrate are added, and condensation is obtained to obtain diazinon.
- 9.34 Storage features
- The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
10. Computational chemical data
- Molecular Weight: 304.345g/mol
- Molecular Formula: C12H21N2O3PS
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 304.10105071
- Monoisotopic Mass: 304.10105071
- Complexity: 307
- Rotatable Bond Count: 7
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 6
- Topological Polar Surface Area: 85.6
- Heavy Atom Count: 19
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceBzMAJAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgAAACAADQihlwIzlJYIERCgASZiZACAgCkhIqABGCA2bBiALgBAycIEFAhOABrAQCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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