17321-47-0

Usage

Uses

Used in Pesticide Industry:
O,O-Dimethyl phosphoramidothioate is used as a pesticide for its ability to control and eliminate various pests that can damage crops and gardens. Its insecticidal properties make it effective against a wide range of insects, helping to protect plants and increase agricultural productivity.
Used in Insecticide Industry:
In the insecticide industry, O,O-Dimethyl phosphoramidothioate is used to control and prevent infestations of insects in various settings, such as homes, commercial buildings, and public spaces. Its potent insecticidal action helps to eliminate insects that can cause damage, spread diseases, or be a nuisance.

InChI:InChI=1/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2/p+4

Upstream product

• 2524-03-0 dimethyl chlorothiophosphate 
• 124-41-4 sodium methylate 
• 65960-90-9 (2R)-3,4c-dimethyl-5c-phenyl-2-thioxo-2λ⁵-[1,3,2]oxazaphospholidin-2r-ylamine 

Downstream Products

• 10265-92-6 Mio 
• 42072-27-5 O,O-dimethyl N-acetylphosphoramidothioate 
• 1229042-25-4 O,O-dimethyl-N-[2,2,2-trichloro-1-(4-phenoxyphenylamino)ethyl] phosphoramidothioate 
• 1229042-18-5 O,O-dimethyl-N-[2,2,2-trichloro-1-(3-chlorophenylamino)ethyl] phosphoramidothioate 
• 1229042-16-3 O,O-dimethyl-N-[2,2,2-trichloro-1-(4-chlorophenylamino)ethyl] phosphoramidothioate 
• 1229042-14-1 O,O-dimethyl-N-(2,2,2-trichloro-1-phenylaminoethyl)phosphoramidothioate 
• 1229042-21-0 O,O-dimethyl-N-[2,2,2-trichloro-1-(4-methylphenylamino)ethyl] phosphoramidothioate 
• 1229042-15-2 O,O-dimethyl-N-[2,2,2-trichloro-1-(4-flurophenylamino)ethyl] phosphoramidothioate 
• 1229042-23-2 O,O-dimethyl-N-[2,2,2-trichloro-1-(2-methylphenylamino)ethyl] phosphoramidothioate 
• 1438853-60-1 O,O-dimethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonylcarbamoylphosphoramidothioate 
• 1438853-61-2 O,O-dimethyl 3-(trifluoromethyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonylcarbamoylphosphoramidothioate 

Relevant academic research and scientific papers

Spermine production process

The invention provides an environment-friendly spermine production process which comprises the following steps: mixing O, O-dimethylthiophosphoryl chloride with a solvent to form a uniform solution, introducing ammonia gas to react for 1-10 hours at the reaction temperature of 5-30 DEG C, and when the content of O, O-dimethylthiophosphoryl chloride in a reaction solution is analyzed to be less than 0.1% by sampling, filtering out ammonium chloride solids from the reaction solution to obtain a filtrate, namely the O, O-dimethyl thiophosphoric amide solution which can be directly used for methamidophos production. The process solves the problem of difficult treatment of wastewater in the ammonia water amination method in the prior art; according to the production process method, adopted production equipment is simple, the process flow is greatly simplified, energy consumption and production cost can be reduced, the produced by-product ammonium chloride can be sold, and the production process is environmentally friendly and economical.

PROCESS FOR PREPARATION OF THIOPHOSPHORYL CHLORIDE AND ACEPHATE

The present invention discloses an improved process for preparation of acephate and intermediates thereof. More particularly, the present invention relates to a process for preparation of thiophosphoryl chloride useful for commercial production of pesticides and pharmaceutically active compounds.

Preparation method of O, O '-dimethyl thiophosphamide

The invention discloses a preparation method of O, O '-dimethyl thiophosphoric amide. The method comprises the following steps: adding water and O, O '-dimethyl thiophosphoryl chloride into a reactioncontainer, stirring, introducing liquid ammonia at a set temperature to enable the mass ratio of the water in the reaction container to the introduced liquid ammonia to be 1: (0.30-0.35) for ammoniation reaction, and stopping introducing the liquid ammonia when the pH value of reaction liquid reaches 8-9; after the reaction is finished, carrying out liquid-solid separation, separating out a water-phase liquid, an organic-phase liquid and a white ammonium chloride solid, and introducing the separated water-phase liquid into a reaction container for cyclic utilization; and distilling the organic phase liquid to recover the solvent, thereby obtaining O, O '-dimethyl thiophosphoric amide. According to the method, the ammonia ratio of a reaction system is increased, the speed is high, the reaction is complete, no wastewater is discharged, the yield is high and the quality is good.

PROCESS FOR PREPARATION OF O, O-DIMEHYL PHOSPHORAMIDOTHIOATE AND N-(METHOXY-METHYLSULFANYLPHOSPHORYL) ACETAMIDE

Preparation of O,O-dimethyl phosphoramidothioate and O,O-dimethyl phosphoroamidothioate. A process of making O,O-dimethyl phosphoroamidothioate is described including reacting sulfur with PCl3 to form PSCl3, reacting the PSCl3 formed with methanol to form O-methyl phosphorodichloridothioate, and reacting the O-methyl phosphorodichloridothioate formed with methyl lye to form O,O-dimethyl phosphorochloridothioate in solution in CH2Cl2, and reacting the O,O-dimethyl phosphorochloridothioate formed with sodium hydroxide and ammonium hydroxide to form O,O-dimethyl phosphoroamidothioate in solution in CH2Cl2. Reacting the O,O-dimethyl phosphoroamidothioate formed with catalytic dimethyl sulfate to form methamidophos, and reacting the methamidophos formed with acetic anhydride to form N-(methoxy-methylsulfanylphosphoryl) acetamide is also described. Throughout the process, the O,O-dimethyl phosphorochloridothioate and the O,O-dimethyl phosphoroamidothioate formed are maintained in solution in CH2Cl2 at all times.

Synthesis, spectroscopic characterization and structure-activity relationship of some phosphoramidothioate pesticides

In this work, some phosphoramidothioates (PATs) with the general formula of (CH3O)2P(S)X and (CH3O)(CH3S)P(O)X, where, X = NH2 (1 & 6), NH(CH3) (2 & 7), N(CH3)2 (3 & 8), N(Et)2 (4 & 9), (CH3CH2O)2P(S)NH(CH3) (5) and (CH3CH2O)(CH3CH2S)P(O)NH(CH 3) (10), were synthesized and characterized by 31P, 31P{1H}, 13C and 1H NMR spectroscopy. The ability of the compounds to inhibit AChE was predicted by PASS software (version 1.193). They were also experimentally evaluated by a modified Ellman's assay. The structure-activity relationship (SAR) between IC50 and some physico-chemical properties such as lipophilicity (logP), electronic and steric effects of the compounds was studied. The logP values were experimentally determined by the shake-flask (gas chromatography) method. Inhibitory potency for the compounds 1-10 was 1 (3.38 mM) > 2 (3.97 mM) > 3 (4.75 mM) > 4 (6.00 mM) > 5 (5.51 mM) > 6 (0.07 mM) > 7 (0.23 mM) > 8 (0.39 mM) > and 9 (0.55 mM) > 10 (0.51 mM), respectively. IC50 and logP parameters of the P=O moiety were more than the P=S moiety in PAT analogues.

Synthesis and characterization of O,S-dimethylphosphoramidothioate and N-acetyl O,S-dimethylphosphoramidothioate

O,S-Dimethylphosphoramidothioate (methamidophos) and N-acetyl O,S-dimethylphos- phoramidothioate (acephate) were synthesized by new methods to investigate the structure-activity study of acetyl cholinesterase (AChE) inhibition through the parameters of logP,δ 31P, and IC 50. After their characterization by NMR (31P, 31P{1H}, 13C, and 1H), IR, and mass spectroscopy, logP and δ31P (31P chemical shift in NMR) were used to evaluate lipophilicity and electronical properties. The logP values for methamidophos and acephate were experimentally determined by the GC-shake-flask method, and the ability of the compounds to inhibit human AChE was evaluated by a modified Ellman's assay. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Development of an enzyme-linked immunosorbent assay for the detection of the organophosphorus insecticide acephate

A competitive indirect enzyme-linked immunosorbent assay (ciELISA) for the organophosphorus insecticide acephate, O,S-dimethyl acetylphosphoramidothioate, was developed using a polyclonal antibody. Five different haptens mimicking the analyte were synthesized and conjugated with the carrier proteins bovine serum albumin (BSA) and keyhole limpet hemocyanin (KLH) by the N-hydroxysuccinimide active ester and diazotization methods. Polyclonal antibodies raised against hapten - KLH conjugates in rabbits and hapten - BSA conjugates as coating antigens were screened and selected for the assay in the homologous and heterologous ELISA systems. The effects of various assay conditions such as detergent, organic solvents, pH, and preincubation of the mixture of the polyclonal antibody and the analyte on the sensitivity were evaluated. The IC50 value for acephate was 25 ng/mL in an optimized heterologous system using hapten-4 - BSA as a coating antigen and a polyclonal antibody no. 8377 against hapten-1 - KLH, showing the detection range of 5-140 ng/mL and the lowest detection limit of 2 ng/mL. The cross-reactivities of the structurally related organophosphorus insecticides, including the major metabolite of the analyte, methamidophos, were less than 1%. Recoveries from the analyte-fortified tap water, mulberry leaves, and lettuce samples in the assay were in the range of 72-121% by simple extraction, concentration, and dilution. These results indicate that the ELISA could be a convenient and supplemental analytical tool for monitoring acephate residues in environmental and agricultural samples.