Stereoselectivity in Toxicity and Acetylcholinesterase Inhibition by the Optical Isomers of Papthion® and Papoxon

Ohkawa, Hideo; Mikami, Nobuyoshi; Kasamatsu, Kiyoshi; Miyamoto, Junshi

doi:10.1080/00021369.1976.10862314

Cited by 4 publications

(3 citation statements)

References 2 publications

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“…The deuterium was incorporated into M+, but not into [(Me0)2P(0)SCH]+. Therefore, M-7 was confirmed as PAP oxon acid (5). By MC compound 12, (Me0)2P(0)SCH2SCH(Ph)000-Me, was not detected, thus further confirming the absence of PAP phosphinyl disulfide formation.…”

Section: Phosphinyl Disulfidesupporting

confidence: 48%

New Metabolites of Phenthoate in Mammalian Systems

et al. 1984

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Twelve transformation products from phenthoate (PAP)[(CH30)2P(S)SCH(Ph)000C2H5]were identified by using intact mice, rat lliver subcellular fractions and peracid. Other than those previously reported, five products were newly found: (CH30)2P(0)SCH(Ph)000H by mice and microsome-NADPH system (mfo), CH3S(0)CH(Ph)000H by mice, HOCH(Ph)-000C2H5 by mice, mfo and cytosol, (CH3S)(CH30)P(0)SCH(Ph)000C2H5(PAP S-isomer) by mfo and (CH30)2P(0)SSCH(Ph)000C2H5 (phosphinyl disulfide) by peracid oxidation. Based on the identification of the products, the initial modifications seem to occur in five ways on PAP: i) hydrolysis of carboxy ethyl ester; ii) demethylation; iii) formation of phosphorus oxythionate; iv) cleavage of C-S bond; and v) isomerization. Further modifications result in various products. Twenty-three unidentified metabolites were found. PAP S-isomer by mfo and phosphinyl disulfide by peracid oxidation are considered to be produced in mice, but their instability does not allow their finding.

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Section: Phosphinyl Disulfidesupporting

confidence: 48%

New Metabolites of Phenthoate in Mammalian Systems

et al. 1984

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“…D-Papthion is more toxic to mosquitoes, rice stem borers, and mice than the L-isomer. In contrast, L-papthion is more toxic to houseflies, and less toxic to mice and other insects than the D-isomer [6]. The S-(-)-enantiomers of methamidophos and acephate are more acutely toxic and stronger anticholinesterases than the R-(+)-enantiomers [7].…”

Section: Introductionmentioning

confidence: 83%

Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Qin

Wang

et al. 2007

J of Separation Science

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Twenty chiral pesticides were tested, of which seven samples were directly separated by HPLC using cellulose tris-3,5-dimethyl carbamate (CDMPC) chiral stationary phase under RP conditions. The influence of mobile phase composition and column temperatures from 0 degrees C to 40 degrees C on the separations were investigated. The mobile phases were methanol/water or ACN/water at a flow rate of 0.8 mL/min with UV detection at 230 or 210 nm. Epoxiconazole, terallethrin, benalaxyl, and diclofopmethyl were observed to obtain the baseline separation under suitable conditions and other pesticides pyriproxyfen, lactofen, and quizalofop-ethyl were separated partially. The retention factors (k) and selectivity factor (alpha) for the enantiomers of most investigated pesticides decreased upon increasing the temperature except for the selectivity factors (alpha) of pyriproxyfen in methanol/water. The ln alpha - 1/T plots for racemic chiral pesticides were linear at the range of 0-40 except for that of pyriproxyfen enantiomers in methanol/water and the chiral separations were controlled by enthalpy. Better separations were not always at low temperature. The elution orders of the eluting enantiomers were determined by a circular dichroism (CD) detector.

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“…In general, the (+)-enantiomer was more toxic than the (-)-form to most organisms except houseflies. Housefly head acetylcholine esterase (ChE) differed from bovine erythroxyte ChE and rice stem borer enzyme in sensitivity towards the enantiomers of papthion and papoxon (13).…”

Section: (-)-mentioning

confidence: 99%

Terminal Residues of Organophosphorus Pesticides

Greenhalgh¹

2016

IUPAC Standards Online

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Current data about the degradation of organophosphorus pesticides in animal, plant and soil substrates and the environment are summarized in this report. Comparative metabolic and chemical studies with racemic and optically active enantiomers are reviewed. These reactions piovide an understanding of the stereochemistry involved in the oxidation of the P=S moiety, which is the main in-vivo activating reaction for organophosphorus insecticides. ANIMALS The metabolism of 1C-triazophos [0,0-diethyl O-(1-phenyl-1 ,2,-triazol-3-yl) phosphorothioate was studied in rats after single and repeated oral doses. Four days after the single dose, 76.3% of the total radioactivity had been excreted in the urine and 21.o% in the feces. After the daily application of 12 doses, 69-83.i-% of the labeled material was eliminated in the urine and 3o.9-18.1% in the feces by day 16. Elimination was markedly slower following prolonged application of the insecticide. Unchanged triazophos and 1-phenyl-1,2+-triazol-3-ol were found in the feces, whilst the urine contained urea (ca. 85% of the urinary activity), the glucuronides of 1-phenyl-1,2,1i-triazol-3-ol (ca. 3%), 1-phenylsemicarbazide (ca. 5%) and semicarbazide (ca. 5%) and two unidentified metabolites (1).

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Stereoselectivity in Toxicity and Acetylcholinesterase Inhibition by the Optical Isomers of Papthion® and Papoxon

Cited by 4 publications

References 2 publications

New Metabolites of Phenthoate in Mammalian Systems

New Metabolites of Phenthoate in Mammalian Systems

Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Terminal Residues of Organophosphorus Pesticides

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