PMID: 16509319Mar 3, 2006Paper

Nucleophilic substitution reactions of chlorpyrifos-methyl with sulfur species

Environmental Science & Technology
Tong Wu, Urs Jans

Abstract

Chlorpyrifos-methyl is widely used in the control of insects on certain stored grain, including wheat, barley, oats, rice, and sorghum. The reactions of chlorpyrifos-methyl with hydrogensulfide/bisulfide (H2S/HS-), polysulfides (Sn(2-)), thiophenolate (PhS-), and thiosulfate (S2O3(2-)) were examined in well-defined aqueous solutions over a pH range from 5 to 9. The rates are first-order in the concentration of the different reduced sulfur species. The resulting data indicate that chlorpyrifos-methyl undergoes a S(N)2 reaction with the reduced sulfur species. The transformation products indicate that the nucleophilic substitution of reduced sulfur species occurs at the carbon atom of a methoxy group to form the desmethyl chlorpyrifos-methyl. The formation of trichloropyridinol, a minor degradation product, could be attributed entirelyto hydrolysis. The reaction of chlorpyrifos-methyl with thiophenolate leads to the formation of the corresponding methylated sulfur compound. The resulting pseudo-first-order rate constant for chlorpyrifos-methyl with bisulfide yielded a second-order rate constant of 2.2 (+/- 0.1) x 10(-3) M(-1) s(-1). The determined second-order rate constants show that the reaction of chlorpyrifos-methyl with HS- ...Continue Reading

References

Feb 7, 2001·Journal of Agricultural and Food Chemistry·A Dannenberg, S O Pehkonen
May 25, 2002·Environmental Science & Technology·K A Lippa, A L Roberts
Jul 9, 2002·Environmental Science & Technology·J A PerlingerW Angst
Mar 20, 2003·Journal of Agricultural and Food Chemistry·Urs Jans, M Hasan Miah

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Citations

Mar 23, 2011·Chemosphere·Dickens Saint-HilaireUrs Jans
Oct 7, 2016·Environmental Science. Processes & Impacts·Rachel M AdamsYu-Ping Chin
Jan 1, 2014·Geochemical Transactions·George R Helz
Dec 12, 2018·Ecotoxicology and Environmental Safety·Hongxia LiuZunyao Wang
Apr 29, 2010·The Journal of Organic Chemistry·Natalia M RougierElba I Buján
Jan 14, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·M S Bootharaju, T Pradeep
Dec 12, 2017·Journal of Agricultural and Food Chemistry·Saumil ChristianUrs Jans

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