Phosphorothionates structure

Casida, J.E. and LJ. Lawrence. 1985. Structure-activity correlations for interactions of bicyclophosphorus esters and some polychlorocycloalkane and pyrethroid insecticides with the brain-specific t-butylcyclo-phosphorothionate receptor. Environ. Health Perspec. 61 123-132. 

Figure 18.9 gives the structural formulas of some typical phosphorothionate esters and the general formula of this type of organophosphate insecticide. 

Mundy, R.L., Bowman, M.C., Fanner, J.H., Haley, T.J. (1978) Quantitative structure-activity study of a series of substituted 0,0-dimethyl 0-(p-nitrophenyl) phosphorothionates and O-analogues. Arch. Toxicol. 41, 111-123. 

Synonyms Bayer E-605 Corthion 0,0-Diethyl-O-(p-nitrophenyl) phosphorothioate Diethyl 4-nitrophenyl phosphorothionate DNTP DDPP Ethyl parathion AC 3422 Alkron Aileron Aphamite Corothion E-605 ENT 15108 Etilon Fosferno 50 Niran Nitrostigine Orthophos Panthion Paramar Paraphos Parathene Para-wet Pethion Phoskil Rhodiatox Soprathion Stathion Sulphos Thiophos Chemical/Pharmaceutical/Other Class Organo-phosphorus insecticide Chemical Structure ... 

OP.v are unstable in aqueous solution and even more so in blood owing to the presence of esterase. After ingestion, OP.v decompose in the human body to yield alkyl phosphates. Typical degradation products are dimethyl phosphate (DMP), dimethyl phosphorothionate (DMTP), dimethyl phosphorodithioate (DMDTP), diethyl phosphate (DEP), diethyl phosphorothionate (DETP) and diethylphosphorodithioate (DEDTP), which are formed by the hydrolysis of the ester bond in the OP molecule. In Figure 9.5 the chemical structures of the respective alkylphosphates are shown. ... 

Two of the transformation products that demonstrate increased potency were the demethylated products of urea herbicides (3-(3-chloro-p-tolyl)-l-methylurea and N-desmethyl-isoproturon), whilst 3,5,6-trichloro-2-pyridinol and 3-methyl-4-nitrophenol are transformation products from OP insecticides that have had the ethylated and methylated phosphorothionate moiety cleaved from their structure, respectively. 

The Ph2PS radical is produced by Jlf-irradiation of diphenylthiophos-phine, and under y-irradiation trichlorosilane brings about the desulphura-tion of phosphine sulphides to phosphines and of phosphorothionates to phosphites. Chloramine-T has been found to be a useful oxidant for distinguishing between a variety of structural units, particularly in phosphorus-sulphur compounds. ... 

The relationship between the chemical structure and toxicity of various coumarin insecticides and anthelmintics are compiled (Table 3.13), and for comparison, some other related compounds are also tabulated. The mammalian toxicity of these compounds is moderate, and their selective action on insects is coimected with differences in metabolism. In mammals these chemicals are probably rapidly metabolised by hydrolysis between the aromatic and phosphate groups, whereas in insects by slow oxidation of the phosphorothionate to phos-... 

Phosphorothionate esters such as parathion, for which the structural formula is, are effective as insecticides because they. ... 

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