3689-24-5

Basic information

• Product Name: SULFOTEP
• Synonyms: O,O,O',O'-TETRAETHYLDITHIOPYRO PHOSPHATE;THIOTEP;THIOTEPP(R);Thiodiphosphoric acid tetraethyl ester;TETRAETHYLDITHIO PYROPHOSPHATE;SULFOTEP;SULFOTEPP;BIS-O,O-DIETHYLPHOSPHOROTHIONIC ANHYDRID
• CAS NO: 3689-24-5
• Molecular Formula: C₈H₂₀O₅P₂S₂
• Molecular Weight: 322.32
• EINECS: 222-995-2
• Product Categories: INSECTICIDE;Agro-products;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 3689-24-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: <25℃
• Boiling Point: bp2 136-139°
• Flash Point: -18 °C
• Appearance: Clear colorless/Liquid
• Density: 1.2175 g/cm3 (20℃)
• Vapor Pressure: 1.7 x 10-4 at 20 °C (Windholz et al., 1983)
• Refractive Index: 1.5000 (589.3 nm 20℃)
• Storage Temp.: APPROX 4°C
• Solubility: Miscible with methyl chloride and most organic solvents (Worthing and Hance, 1991)
• Water Solubility: 30 mg/L at 20 °C (Worthing and Hance, 1991)
• Merck: 13,9056
• BRN: 1714019
• CAS DataBase Reference: SULFOTEP(CAS DataBase Reference)
• NIST Chemistry Reference: SULFOTEP(3689-24-5)
• EPA Substance Registry System: SULFOTEP(3689-24-5)

Safety Data

• Hazard Codes: T+,N,Xn,F
• Statements: 27/28-50/53-67-65-38-11
• Safety Statements: 23-28-36/37-45-60-61-62
• RIDADR: 1704
• WGK Germany: 3
• RTECS: XN4375000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 3689-24-5(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 3689-24-5 differently. You can refer to the following data:
1. Yellowliquid. Slightly soluble in water; soluble in most organic solvents.
2. Sulfotep is a yellow mobile liquid. Garliclike odor.

Uses

Different sources of media describe the Uses of 3689-24-5 differently. You can refer to the following data:
1. An organophosphate pesticide that is an inhibitor of acetylcholinesterase (AChE).
2. Insecticide; miticide.
3. Insecticide
4. Sulfotep is used to control aphids, thrips, mites and whiteflies in glasshouses by fumigation. It also used to control sciarid and phorid flies in mushrooms.

General Description

Tetraethyl dithiopyrophosphate and compressed gas mixture is a liquid charged with a gas. Tetraethyl dithiopyrophosphate is a yellow liquid. Its vapor is heavier than air. SULFOTEP is lethal by skin absorption and inhalation. Prolonged exposure of the containers to fire or heat may result in their violent rupturing and rocketing.

Reactivity Profile

Organothiophosphates, such as TETRAETHYL DITHIOPYROPHOSPHATE, 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. SULFOTEP is incompatible with the following: Strong oxidizers, iron [Note: Corrosive to iron.] .

Hazard

Toxic by ingestion, inhalation, and skin absorption; cholinesterase inhibitor; use may be restricted. Questionable carcinogen.

Safety Profile

Poison by ingestion, skin contact, inhalation, intramuscular, intraperitoneal, subcutaneous, and intravenous routes. A cholinesterase inhbitor type of insecticide. When heated to decomposition it emits toxic fumes of POx and SOx. See also PARATHION.

Potential Exposure

Sulfotep is used in greenhouse fumigant formulations for control of aphids, spider mites; thrips, whiteflies, etc.

Environmental Fate

Soil. Cleavage of the molecule yields diethyl phosphate, monoethyl phosphate and phosphoric acid (Hartley and Kidd, 1987).Chemical/Physical. Emits toxic oxides of sulfur and phosphorus oxides when heated to decomposition (Lewis, 1990).

Metabolic pathway

Sulfotep and related compounds may be formed photochemically from a number of phosphorodithioate and phosphorothioate insecticides including azinphos-methyl, chlorpyrifos, malathion, methidathion and phosalone (Abdelbagi and Gaston, 1998). Since sulfotep has a rather high mammalian toxicity, this may be of some toxicological sigruficance. Sulfotep is transformed in the environment via oxidative desulfuration to the highly active anti-cholinesterase compounds monosulfotep and tetraethyl pyrophosphate. It is deactivated by hydrolysis to O,O-diethyl phosphorothioate and diethyl phosphate.

Shipping

UN1704 (Sulfotep) Tetraethyl dithiopyrophosphate, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Degradation

Sulfotep is relatively slowly hydrolysed with DT50 values of 10.7,8.2 and 9.1 days at pH values 4,7 and 9 respectively (PM).

Toxicity evaluation

Sulfotep is formulated as fumigant. The acute oral LD50 for rats is about 10 mg/kg. Inhalation LC50 (4 h) for rats is about 0.05 mg/L air. NOEL (2 yr) for rats is 10mg/kg diet (0.5mg/kg/d). ADI is 1 μg/kg b.w. Sulfotep is activated by oxidative desulfuration to tetraethyl monothiopyrophosphate and pyrophosphate in the environment. Sulfotep administered to rats is quickly eliminated. The major elimination product is diethyl hydrogen phosphorothioate.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Hydrolyzes very slowly in aqueous solution. Attacks some forms of plastic, rubber and coating. Corrosive to iron.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Incineration with added flammable solvent in furnace equipped with afterburner and alkaline scrubber.

InChI:InChI=1/C8H20O6P2S/c1-5-11-15(9,12-6-2)14-16(10,13-7-3)17-8-4/h5-8H2,1-4H3

Synthetic route

3-chloro-2-methyl-quinolin-4-ol (31403-66-4, 83842-53-9) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Thiophosphoric acid O-(3-chloro-2-methyl-quinolin-4-yl) ester O',O''-diethyl ester (93516-24-6)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;	A n/a B 74%

3-Chlor-4-hydroxy-7-trifluormethylchinolin (65673-93-0) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Thiophosphoric acid O-(3-chloro-7-trifluoromethyl-quinolin-4-yl) ester O',O''-diethyl ester (93516-26-8)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;	A n/a B 72%

4-hydroxy-2-methylquinoline (607-67-0) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Quinothion (22439-40-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;	A n/a B 70%

7-chloro-4-hydroxylquinoline (86-99-7) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Thiophosphoric acid O-(7-chloro-quinolin-4-yl) ester O',O''-diethyl ester (93516-22-4)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;	A n/a B 69%

4(1H)-quinolinone (529-37-3) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Thiophosphoric acid O,O'-diethyl ester O''-quinolin-4-yl ester (93516-19-9)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;	A n/a B 66%

7-trifluoromethyl-quinolin-4-ol (322-97-4) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Thiophosphoric acid O,O'-diethyl ester O''-(7-trifluoromethyl-quinolin-4-yl) ester (93516-25-7)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;	A n/a B 65%

2,3-dimethylquinolin-4-ol (10352-60-0) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + Thiophosphoric acid O-(2,3-dimethyl-quinolin-4-yl) ester O',O''-diethyl ester (93644-61-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;	A n/a B 63%

diethyl phosphorochloridothioate (2524-04-1) + 4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one (58861-80-6) → sulfotep (3689-24-5) + (5-Methyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester (135492-37-4)

Conditions	Yield
With potassium carbonate In acetonitrile a) 1 h, 35 deg C, b) 4 h, 50 deg C;	A n/a B 63%

diethyl phosphorochloridothioate (2524-04-1) + 3,7-dichloroquinolin-4-ol (152210-26-9, 93516-30-4) → sulfotep (3689-24-5) + 3,7-Dichloro-1-ethyl-1H-quinolin-4-one (93516-27-9) + Thiophosphoric acid O-(3,7-dichloro-quinolin-4-yl) ester O',O''-diethyl ester (93516-23-5)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;	A n/a B 16% C 62%

5-benzyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (128070-22-4) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + (5-Benzyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester (135492-46-5)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	A n/a B 53%

3-chloro-quinolin-4-ol (58550-89-3) + diethyl phosphorochloridothioate (2524-04-1) → 3-chloro-1-ethyl-1H-quinolin-4-one (64965-21-5) + sulfotep (3689-24-5) + Thiophosphoric acid O-(3-chloro-quinolin-4-yl) ester O',O''-diethyl ester (93516-21-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;	A 17% B n/a C 52%

5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one (99822-19-2) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + (5-Isopropyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester (135492-43-2)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	A n/a B 52%

diethyl phosphorochloridothioate (2524-04-1) + 1,5-dimethyl-4,5-dihydro-1,2,4-triazine-6-one (135492-32-9) → sulfotep (3689-24-5) + (1,5-Dimethyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester (135492-38-5)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	A n/a B 50%

1,3,4,5-tetrahydro<1,2,4>triazin 6(2H)-one (76990-32-4) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + (6-Oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester (135492-34-1)

Conditions	Yield
With potassium carbonate In acetonitrile 1.) 35 deg C, 1 h, 2.) 50 deg C, 4 h;	A n/a B 45%

3-methylquinolin-4-ol (64965-46-4) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + 1-(O,O-Diethylphosphorothio)-3-methyl-4-oxo-1,4-dihydroquinoline (93516-28-0) + Thiophosphoric acid O,O'-diethyl ester O''-(3-methyl-quinolin-4-yl) ester (93516-20-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;	A n/a B 21% C 31%

5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one (99822-19-2) + O,O-dipropyl chlorothiophosphate (2524-05-2) → sulfotep (3689-24-5) + [6-(Dipropoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-dipropyl ester (134202-30-5)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	A n/a B 28%

5-isopropyl-4,5-dihydro-1,2,4-triazin-6-(1H)-one (99822-19-2) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5) + [6-(Diethoxy-thiophosphoryloxy)-5-isopropyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester (134202-29-2)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	A n/a B 25%

diethyl phosphorochloridothioate (2524-04-1) + 4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one (58861-80-6) → sulfotep (3689-24-5) + [6-(Diethoxy-thiophosphoryloxy)-5-methyl-5H-[1,2,4]triazin-4-yl]-phosphonothioic acid O,O-diethyl ester (134202-27-0)

Conditions	Yield
With potassium carbonate In acetonitrile 1.) 1 h, 35 deg C, 2.) 4 h, 50 deg C;	A n/a B 20%

pyridine (110-86-1) + Diethyl phosphate (598-02-7) + diethyl phosphorochloridothioate (2524-04-1) → Tetraethyl pyrophosphate (107-49-3) + tetraethyl thiopyrophosphate (645-78-3) + sulfotep (3689-24-5)

Conditions	Yield
das Natrium-Salz reagiert;

diethyl phosphorylchloridite (589-57-1) + sodium diethyl phosphite (2303-76-6, 118080-94-7) → sulfotep (3689-24-5)

Conditions	Yield
und Erhitzen des Reaktionsgemisches mit Schwefel;

O,O,O-triethyl phosphorothioate (126-68-1) → sulfotep (3689-24-5)

Conditions	Yield
With sulfuric acid

diphosphorous acid tetraethyl ester (21646-99-1) → sulfotep (3689-24-5)

Conditions	Yield
With sulfur at 160℃;

sodium diethyl phosphite (2303-76-6, 118080-94-7) + diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5)

Conditions	Yield
With Petroleum ether und anschliessenden Erwaermen mit Schwefel;

diethyl phosphorochloridothioate (2524-04-1) + O,O'-diethyl thiophosphoric acid (2465-65-8) → sulfotep (3689-24-5)

Conditions	Yield
With triethylamine

diethyl phosphorochloridothioate (2524-04-1) → sulfotep (3689-24-5)

Conditions	Yield
With pyridine; water

diethyl phosphorylchloridite (589-57-1) + phosphonic acid diethyl ester (762-04-9) → sulfotep (3689-24-5)

Conditions	Yield
With pyridine; sulfur; toluene

diphenylphosphinous acid methyl ester (4020-99-9) + bis(diethylphosphoryl)disulfide (4403-51-4) → O,O-diethyl S-methyl phosphorothioate (2404-05-9) + sulfotep (3689-24-5) + C16H20O4P2S + methyl diphenylphosphinate (1706-90-7)

Conditions	Yield
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Title compound not separated from byproducts;

tri-n-butyl phosphite (102-85-2) + bis(diethylphosphoryl)disulfide (4403-51-4) → tetraethyl thiopyrophosphate (645-78-3) + sulfotep (3689-24-5) + diethyl S-tert-butyl thiophosphate (7795-74-6) + C12H28O6P2S

Conditions	Yield
With trineopentyl phosphite In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts;
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts;

trineopentyl phosphite (14540-52-4) + bis(diethylphosphoryl)disulfide (4403-51-4) → sulfotep (3689-24-5) + C19H43O6P2S(1+)*C4H10O3PS(1-) + C19H43O6P2S(1+)*C4H10O3PS(1-)

Conditions	Yield
at -100 - -30℃; Mechanism;

bis(diethylphosphoryl)disulfide (4403-51-4) + 2-ethoxy-1,3,2-benzodioxaphosphole (10072-02-3) → O,O,S-triethyl phosphorothioate (1186-09-0) + tetraethyl thiopyrophosphate (645-78-3) + sulfotep (3689-24-5) + Thiophosphoric acid O,O'-diethyl ester O''-(2-oxo-2λ5-benzo[1,3,2]dioxaphosphol-2-yl) ester

Conditions	Yield
In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Further byproducts given. Title compound not separated from byproducts;

sulfotep (3689-24-5) → diethyl phosphorofluoridothioate (358-75-8)

Conditions	Yield
With hydrogen fluoride

Upstream product

• 2303-76-6 sodium diethyl phosphite 
• 2524-04-1 diethyl phosphorochloridothioate 
• 2465-65-8 O,O'-diethyl thiophosphoric acid 
• 589-57-1 diethyl phosphorylchloridite 
• 762-04-9 phosphonic acid diethyl ester 
• 64965-46-4 3-methylquinolin-4-ol 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 10352-60-0 2,3-dimethylquinolin-4-ol 
• 31403-66-4 3-chloro-2-methyl-quinolin-4-ol 
• 102-85-2 tri-n-butyl phosphite 
• 4403-51-4 bis(diethylphosphoryl)disulfide 
• 14540-52-4 trineopentyl phosphite 
• 152210-26-9 3,7-dichloroquinolin-4-ol 
• 110-86-1 pyridine 

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