5598-13-0

Usage

Reactivity Profile

A chlorinated organophosphate derivative. Organophosphates 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. Chlorpyrifos-methyl is incompatible with strong acids and bases.

Health Hazard

Exposures to chlorpyrifos-methyl cause excessive salivation, sweating, rhinorrhea and tearing, muscle twitching, blurred vision/dark vision, slurred speech, weakness, tremor, incoordination, headache, dizziness, nausea, vomiting, abdominal cramps, diarrhea, respiratory depression, tightness in chest, wheezing, productive cough, fl uid in lungs, and pin-point pupils. In cases of severe exposure and poisoning, chlorpyrifos-methyl causes seizures, incontinence, respiratory depression, loss of consciousness, respiratory paralysis, and death. Exposures to chlorpyrifos-methyl cause cholinesterase inhibition in workers, and the systemic toxicity includes body weight loss, decreased food consumption, and liver, kidney, and adrenal pathology

Trade name

DOWCO-217?; NOLTRAN?; RELDAN?; RELDANE? , STORCIDE?; ZERTELL?

Safety Profile

Moderately toxic by ingestion, intraperitoneal, and skin contact routes. A skin irritant. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Cl-, NOx POx and SOxA pesticide.

Potential Exposure

Chlorpyrifos-methyl is a general use organophosphate insecticide for use on stored grain (for protection of stored food, feed oil, and seed grains against injury from stored grain weevils, moths, borers, beetles, and mealworms including granary weevil, rice weevil, red flour beetle, confused flour beetle, saw-toothed grain beetle, Indian meal moth, and Angoumois grain moth, lessor grain borers), seed treatment, grain bin, and warehouse.

Incompatibilities

Strong oxidizers, strong acids, and alkalies. 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. Corrosive to copper, brass, iron, and tin plate.

Waste Disposal

Chlorpyrifos-methyl is 50% hydrolyzed in aqueous methanol solution @ pH 6 in 1930 days; and in 7.2 days at pH 9.96. Spray mixtures of <1% concentration are destroyed with an excess of 5.25% sodium hypochlorite in ,30 minutes @ 100°C; and in 24 hours @ 30°C. Concentrated (61.5%) mixtures are essentially destroyed by treatment with 100:1 volumes of the above sodium hypochlorite solution and steam in 10 minutes. 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

Precautions

Workplaces should have adequate washing facilities at all times during handling and these should be close to the site of handling. Eating, drinking, and smoking should be prohibited during handling and before washing after handling. Containers of chlorpyrifosmethyl should be kept away from foodstuffs, animal feed and their containers, and out of reach of children

InChI:InChI=1/C7H7Cl3NO3PS/c1-12-15(16,13-2)14-7-5(9)3-4(8)6(10)11-7/h3H,1-2H3

Synthetic route

sodium salt of 3,5,6-trichloropyridine-2-ol + ethyl methyl chlorothiophosphate (71348-06-6, 13289-13-9) → O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0)

Conditions	Yield
In ethanol at 50℃; for 5h; Temperature;	96.2%

dimethyl chlorothiophosphate (2524-03-0) + sodium salt of 3,5,6-trichloropyridine-2-ol → O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0)

Conditions	Yield
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;	93.4%

3,5,6-trichloropyridin-2 ol (6515-38-4) + dimethylthiophosphoric acid (1112-38-5) → O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0)

Conditions	Yield
With water; sodium hydroxide In acetonitrile at 25℃; for 6h; pH=9.14; Equilibrium constant; Solvent;

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) → Fospirate (5598-52-7)

Conditions	Yield
With monoperoxyphthalic acid; magnesium salt In dichloromethane for 12h; Heating;	44%

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) + 3-mercaptopropionic acid (107-96-0) → 3-[3,5-Dichloro-6-(dimethoxy-thiophosphoryloxy)-pyridin-2-ylsulfanyl]-propionic acid

Conditions	Yield
With potassium hydroxide In ethanol for 1h; Heating;	3.5%

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) → thiophosphoric acid O-methyl ester O'-(3,5,6-trichloro-pyridin-2-yl) ester + O-(3,5,6-trichloropyridin-2-yl) O,O-dihydrogenphosphorothioate

Conditions	Yield
CuCl2*2H2O In methanol; water pH=3.5 - 7.0; Kinetics; Further Variations:; Catalysts; Hydrolysis;

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) → 3,5,6-trichloropyridin-2 ol (6515-38-4)

Conditions	Yield
With sodium phosphate buffer; hydrogen sulfide; sodium chloride In methanol at 25℃; pH=5.9; Kinetics; Further Variations:; pH-values; var. hydrogen sulfide concentration;
With C54H36N6NiO10S2 In aq. phosphate buffer at 30℃; for 0.833333h;

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) → 3,5,6-trichloropyridin-2 ol (6515-38-4) + dimethylthiophosphoric acid (1112-38-5)

Conditions	Yield
With bacterial phosphotriesterase wild-type OpdA In methanol at 37℃; pH=8.5; Enzyme kinetics;
With water; sodium hydroxide In acetonitrile at 25℃; for 6h; Kinetics; Mechanism; Equilibrium constant; Solvent; Concentration; Reagent/catalyst; pH-value;

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) → monomethyl thiophosphate (1111-99-5)

Conditions	Yield
With 4-methyl-morpholine In water at 45℃; for 24h; pH=10;

O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (5598-13-0) → 3,5,6-trichloropyridin-2 ol (6515-38-4) + Fospirate (5598-52-7) + dimethylphosphoric acid (813-78-5) + dimethylthiophosphoric acid (1112-38-5)

Conditions	Yield
With air In acetonitrile for 3.91667h; Kinetics; Reagent/catalyst; Solvent; UV-irradiation;

Upstream product

• 6515-38-4 3,5,6-trichloropyridin-2 ol 
• 1112-38-5 dimethylthiophosphoric acid 
• 71348-06-6 ethyl methyl chlorothiophosphate 
• 2524-03-0 dimethyl chlorothiophosphate 

Downstream Products

• 6515-38-4 3,5,6-trichloropyridin-2 ol 
• 1112-38-5 dimethylthiophosphoric acid 
• 5598-52-7 Fospirate 
• 813-78-5 dimethylphosphoric acid 
• 1111-99-5 monomethyl thiophosphate 

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Terahertz sensing of Chlorpyrifos-methyl (cas 5598-13-0) using metamaterials07/15/2019

By squeezing electromagnetic energy into small volumes near a metal-dielectric interface, plasmonics provide many routes to enhance and manipulate light-matter interactions, which presents new strategies for signal enhancing technologies. As an extension of the ideas of plasmonics to the teraher...detailed

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The effects of inherent minerals in biochars and low molecular weight organic acids (LMWOAs) on chlorpyrifos and chlorpyrifos-methyl adsorption by biochars are unclear. We examined the sorption of chlorpyrifos and chlorpyrifos-methyl onto giant reed-derived biochars before and after deashing or ...detailed

Relevant academic research and scientific papers

Preparation methods of methyl ethyl thiophosphoryl chloride and methyl ethyl chlorpyrifos

The invention provides a preparation method of methyl ethyl thiophosphoryl chloride and relates to the field of chemical synthesis. Thiophosphoryl chloride is adopted as an initial raw material and reacts with ethyl alcohol to obtain an intermediate A; the intermediate A reacts with sodium methoxide to obtain the methyl ethyl thiophosphoryl chloride. The preparation method is simple to operate, raw materials are easy to obtain, reaction conditions are mild, and the methyl ethyl thiophosphoryl chloride can be obtained with high efficiency and high yield only through the simple two-step reaction. The invention further provides a preparation method of methyl ethyl chlorpyrifos; the methyl ethyl thiophosphoryl chloride is prepared by adopting the preparation method of the methyl ethyl thiophosphoryl chloride and then reacts with sodium trichloro pyridinol to obtain the methyl ethyl chlorpyrifos. The preparation method is simple and convenient to operate and low in requirements for equipment and can realize the scale production of the methyl ethyl chlorpyrifos.

Investigation on the acylation of heterocyclic alcoholate anions with O,O-dialkyl phosphorochloridothioate in water solvent

The acylation of some heterocyclic alcoholate anions with O,O-dialkyl phosphorochloridothioate has been investigated. Higher yields and fewer byproducts were achieved in water at 50 °C by employing an effective phase-transfer catalyst (PTC) (benzyl triethylammonium chloride [BTEAC]), acylation catalyst (AC) (4-dimethylaminopyridine), and surfactant (sodium dodecyl sulfate), under weakly basic (pH 9.5～10) conditions. This reaction can also be applied to synthesize other insecticides with excellent yields.

Reactivity of the insecticide chlorpyrifos-methyl toward hydroxy! and perhydroxyl ion. Effect of cyclodextrins

The reactivity of Chlorpyrifos-Methyl (1) toward hydroxyl ion and the α-nucleophile, perhydroxyl ion was investigated in aqueous basic media. The hydrolysis of 1 was studied at 25° C in water containing 10% ACN or 7% 1,4-dioxane at NaOH concentrations between 0.01 and 0.6m; the second-order rate constant is 1.88 × 10-2m-1 s-1 in 10% ACN and 1.70 × 10-2m-1 s-1 in 7% 1,4-dioxane. The reaction with H2O2 was studied in a pH range from 9.14 to 12.40 in 7% 1,4-dioxane/H2O; the second-order rate constant for the reaction of HOO ion is 7.9 m-1 s-1 whereas neutral H2O2 does not compete as nucleophile. In all cases quantitative formation of 3,5,6-trichloro-2-pyridinol (3) was observed indicating an SN2(P) pathway. The hydrolysis reaction is inhibited by α-, β-, and γ-cyclodextrin showing saturation kinetics; the greater inhibition is produced by γ-cyclodextrin. The reaction with hydrogen peroxide is weakly inhibited by α- and β-cyclodextrin (β-CD), whereas g-cyclodextrin produces a greater inhibition and saturation kinetics. The kinetic data obtained in the presence of β-or γ-cyclodextrin for the reaction with hydroxyl or perhydroxyl ion indicate that the main reaction pathway for the cyclodextrin-mediated reaction is the reaction of HO- or HOO- ion with the substrate complexed with the anion of the cyclodextrin. The inhibition is attributed to the inclusion of the substrate with the reaction center far from the ionized secondary OH groups of the cyclodextrin and protected from external attack of the nucleophile. Sucrose also inhibits the hydrolysis reaction but the effect is independent of its concentration. Copyright

Condensation products

Formamidine compounds of the formula EQU1 or WHEREIN R1 represents a substituted or unsubstituted phenyl radical, R2 represents hydroogen, alkyl, alkenyl or alkinyl and R3 represents acyl their manufacture and their use in pest control.