Diazinon

Base Information

• Chemical Name: Diazinon
• CAS No.: 333-41-5
• Deprecated CAS: 27936-40-9,30583-38-1,65863-03-8,30583-38-1,65863-03-8
• Molecular Formula: C12H21N2O3PS
• Molecular Weight: 304.35
• Hs Code.: 29335990
• European Community (EC) Number: 206-373-8
• ICSC Number: 0137
• NSC Number: 755893,8938
• UN Number: 3018,2783
• UNII: YUS1M1Q929
• DSSTox Substance ID: DTXSID9020407
• Nikkaji Number: J3.278F
• Wikipedia: Diazinon
• Wikidata: Q411202
• NCI Thesaurus Code: C169912
• Metabolomics Workbench ID: 45800
• ChEMBL ID: CHEMBL388560
• Mol file: 333-41-5.mol

Synonyms:Dassitox;Topclip 40;Diazinon AG 500;diethoxy-(6-methyl-2-propan-2-yl-pyrimidin-4-yl)oxy-sulfanylidene-phosphorane;Sarolex;Diazol;Drawizon;O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidinyl) phosphorothioate;Isopropylmethylpyrimidyl diethyl thiophosphate;o, o-Dietil-o- (2-isopropil-4-metil-pirimidin-il)-monotiofosato(ITALIA N);Ektoband;Kleen-Dok;O-2-Isopropyl-4-methylpyrimidyl-O,O-diethyl phosphorothioate;Diazajet;Dimpylat;Phosphorothioic acid, O, O-diethyl O- (2-isopropyl-6-methyl-4-pyrimidinyl) ester;Topclip Blue Shield;O, O-Diethyl-O- (2-isopropyl-4-methyl-pyrimidin-6-yl)-monothiofosfaat( DUTCH);O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) thiophosphate;Basudin 10 G;Antigal;O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioate;Diazitol;Phosphorothioic acid, O,O-diethyl {O-[6-methyl-2-(1-methylethyl)-4-pyrimidinyl]} ester;O,O-Diethyl O-6-methyl-2-isopropyl-4-pyrimidinyl phosphorothioate;Phosphorothioic acid, O,O-diethyl O-[6-methyl-2- (1-methylethyl)-4-pyrimidinyl] ester;Galesan;Exodin;Cooper's Flystrike Powder;Dizictol;4-Pyrimidinol, 2-isopropyl-6-methyl-, O-ester with O,O-diethyl phosphorothioate;Bazudin;Delzinon;G-24480;Dimpylate;Knox-out;O, O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphate;Diazinone;Nedcidol;Disonex;Garden Tox;KFM Blowfly Dressing;Spectracide;Phosphorothioate, O,O-diethyl O-6- (2-isopropyl-4-methylpyrimidyl);Flytrol;Bazanon;Nucidol;Topclip Blue;

Chemical Property of Diazinon

Chemical Property:

• Appearance/Colour: light to dark brown liquid
• Vapor Pressure: 0.000228mmHg at 25°C
• Melting Point: >120 °C (dec.)
• Refractive Index: 1.595
• Boiling Point: 353.9 °C at 760 mmHg
• PKA: 1.21±0.30(Predicted)
• Flash Point: 167.9 °C
• PSA: 95.37000
• Density: 1.168 g/cm³
• LogP: 4.23530
• Storage Temp.: APPROX 4°C
• Water Solubility.: Slightly soluble. 0.004 g/100 mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 304.10105071
• Heavy Atom Count: 19
• Complexity: 307
• Transport DOT Label: Poison

Purity/Quality:

95% ^*data from raw suppliers

Diazinon ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, F
• Hazard Codes: Xn;N,N,Xn,F
• Statements: 22-50/53-36-20/21/22-11-51/53
• Safety Statements: 24/25-60-61-36-26-16-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and skin. The substance may cause effects on the nervous system. Cholinesterase inhibition. This may result in convulsions and respiratory depression. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms. This substance is probably carcinogenic to humans.
• 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. Diazinon is a broad-spectrum insecticide that is active against approximately 120 species of insects and pests. 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.
• Uses: Insecticide. insecticide, cholinesterase inhibitor A cholinesterase inhibitor; a nonsystemic organophosphate insecticide. Nonsystemic contact insecticide used against flies, aphids and spider mites in soil, fruit, vegetables and ornamentals. 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.

Technology Process of Diazinon

There total 9 articles about Diazinon which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.7%

→ `Diazinon` (333-41-5,65863-03-8)

Guidance literature:

Reference yield: 98.4%

sodium 2-isopropyl-6-methylpyrimidin-4-olate (63202-32-4) + diethyl phosphorochloridothioate (2524-04-1) → `Diazinon` (333-41-5,65863-03-8)

Guidance literature:

With dmap; N-benzyl-N,N,N-triethylammonium chloride; sodium dodecyl sulfate; potassium carbonate; In water; at 50 ℃; for 2.5h; pH=9.5 - 10;

DOI:10.1080/10426507.2012.702824

Reference yield: 87.3%

→ 6,6'-diazido-6,6'-dideoxy-1',2,3,3',4,4'-hexa-O-methylsucrose + `Diazinon` (333-41-5,65863-03-8)

Guidance literature:

upstream raw materials:

diethyl phosphorochloridothioate

sodium 2-isopropyl-6-methylpyrimidin-4-olate

2-isopropyl-6-methyl-4-pyrimidinol

sodium hydrogencarbonate

Downstream raw materials:

2-isopropyl-6-methyl-4-pyrimidinol

O,O'-diethyl thiophosphoric acid

ethyl N,N-diethylcarbamate

phosphonic acid diethyl ester

Refernces

• 1、 Churchill, Doreen,Cheung, Jason Chiu Fung,Park, Yong Sung,Smith, Vedene H.,VanLoon, Gary,Buncel, Erwin. "Complexation of diazinon, an organophosphorus pesticide, with α-, β-, and γ-cyclodextrin - NMR and computational studies". . p. 702 - 708. Retrieved 2006.
• 2、 Ge, Xin,Qian, Chao,Chen, Xinzhi. "Investigation on the acylation of heterocyclic alcoholate anions with O,O-dialkyl phosphorochloridothioate in water solvent". supporting information. p. 739 - 744. Retrieved 2013/07/25.
• 3、 -. "NOVEL MULTIMERIC MOLECULES, A PROCESS FOR PREPARING THE SAME AND THE USE THEREOF FOR MANUFACTURING MEDICINAL DRUGS". . . Retrieved 2010/06/16.