Stereoisomeric separation and toxicity of the nematicide fosthiazate.

Kunde Lin, Feng Zhang, Shanshan Zhou, Weiping Liu, Jay Gan, Zhiyan Pan

Research Center of Environmental Science, Zhejiang University of Technology, Hangzhou 310032, China.

Environmental toxicology and chemistry / SETAC 2007 Nov

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Considerable attention has been paid to the enantiomeric resolution and toxicity of some chiral organophosphorous pesticides (OPs) with one asymmetric center, but research concerning chiral OPs with two asymmetric centers is still limited. In the present study, the stereoisomeric separation and toxicity of fosthiazate, a chiral OP with two asymmetric centers on phosphorus and carbon atoms, was investigated. All four stereoisomers of fosthiazate were separated successfully with a Chiralpak(R) AD [amylase tris(3,5-dimethyl-phenyl carbamate)] column on high-performance liquid chromatography. The resolved isomers and the pairs of enantiomers were further distinguished using a circular dichroism detector and an optical rotation detector, designating the first (pk1) and third (pk3) eluted peaks as one pair of enantiomers and the second (pk2) and fourth (pk4) peaks as the other pair. The developed method was used to prepare microquantities of individual stereoisomers that were used for in vitro and in vivo bioassays. The inhibition potencies of the stereoisomers against acetylcholinesterase of Electrophorus electricus were slightly stereoselective, with a maximum difference of 1.4-fold among the isomers. A 3.1-fold difference, however, was observed in the acute toxicity of isomers to Daphnia magna. The 48-h toxicity of isomers to D. magna followed the order pk1 > pk2 > pk4 > racemate approximately pk3. The stereoselective toxicity to D. magna found in fosthiazate suggests that the environmental safety of fosthiazate should be evaluated on the basis of its individual isomers.

Citation

Kunde Lin, Feng Zhang, Shanshan Zhou, Weiping Liu, Jay Gan, Zhiyan Pan. Stereoisomeric separation and toxicity of the nematicide fosthiazate. Environmental toxicology and chemistry / SETAC. 2007 Nov;26(11):2339-44