Separation and aquatic toxicity of enantiomers of the organophosphorus insecticide trichloronate

Liu, Weiping; Lin, Kunde; Gan, Jianying

doi:10.1002/chir.20323

Cited by 49 publications

(40 citation statements)

References 15 publications

(13 reference statements)

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“…[5][6][7][8][12][13][14]32,33 In this investigation, satisfactory resolution of salithion enantiomers was achieved on all of the three CSPs of derivative cellulose and amylase we selected, among which the Chiralpak AD column offered the highest a of more than 1.20 suggesting a baseline resolution. 34 Moreover, the chiral recognition ability of Chiralpak AD also seems better than that of Chiralcel OB and Chiralpak OT(1), the two columns that have been used to separate salithion enantiomers previously.…”

Section: Results and Discussion Enantiomer Separation And Identificationmentioning

confidence: 98%

“…Recently, increasing studies have demonstrated that enantioselectivity also exists in the in vivo acute aquatic toxicity of chiral OPs. [5][6][7]9,10,[12][13][14] Salithion ((RS)-2-methoxy-4H-1,3,2 k 5 benzodioxaphosphorin 2-sulfide), an organophosphorus pesticide, which was first synthesized in 1963, is used for control of a broad spectrum of insect pests in orchards or vegetables. 15,16 In recent years, because of its high efficacy, low cost, and capacity to control pyrethrin-resistant pests, 17 salithion has been considered as an effective alternative of the highly toxic OPs in China.…”

Section: Introductionmentioning

confidence: 99%

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Separation and toxicity of salithion enantiomers

Zhou¹,

Lin²,

Li³

et al. 2009

Chirality

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Enantioseletive toxicities of chiral pesticides have become an environmental concern recently. In this study, we evaluated the enantiomeric separation of salithion on a suite of commercial chiral columns and assessed the toxicity of enantiomers toward butyrylcholinesterase and Daphnia magna. Satisfactory separations of salithion enantiomers could be achieved on all tested columns, that is, Chiralcel OD, Chiralcel OJ, and Chiralpak AD column. However, the Chiralpak AD column offered the best separation and was chosen to prepare micro-scale of pure salithion enantiomers for subsequent bioassays. The first and second enantiomers eluted on the Chiralpak AD column were further confirmed to be (-)-S-salithion and (+)-R-salithion, respectively. The half inhibition concentrations to butyrylcholinesterase of racemate, (+)-R-salithion, and (-)-S-salithion were 33.09, 2.92, and 15.60 mg/l, respectively, showing (+)-R-enantiomer being about 5.0 times more potent than its (-)-S-form. However, the median lethal concentrations (96 h) of racemate, (+)-R-salithion, and (-)-S-salithion toward D. magna were 3.54, 1.10, and 0.36 microg/l, respectively, suggesting that (-)-S-salithion was about 3.0 times more toxic than (+)-R-form. Racemic salithion was less toxic than either of the enantiomers in both bioassays, suggesting that antagonistic interactions might occur between the enantiomers during the toxication action. This work reveals that the toxicity of salithion toward butyrylcholinesterase and D. magna is enantioselective, and this factor should be taken into consideration in the environmental risk assessment of salithion.

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Section: Results and Discussion Enantiomer Separation And Identificationmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Separation and toxicity of salithion enantiomers

Zhou¹,

Lin²,

Li³

et al. 2009

Chirality

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“…Similar to our finding (compounds 3 and 5), the in vivo toxicities of fenamiophos, 32 leptophos, 33 and methanmidophos 11 to D. magna arose primarily from their (1)-enantiomer. In contrast, the toxicity to D. magna of the other three chiral OPs, fonofos, profenofos 4 and trichoronate, 12 was primarily from their (2)-enantiomers. The toxicities of these OPs were enantioselective.…”

Section: Enantioselectivity In Aquatic Toxicitymentioning

confidence: 78%

“…11 The acute aquatic toxicity of trichloronate to D. magna was also found to be selective that the (2)-form was 8-11 times more toxic than its (1)-form, while the racemate showed intermediate toxicity. 12 A series of 1-(substituted phenoxyacetoxy)alkylphosphonate herbicides have been synthesized. They possess notable herbicidal activities, [13][14][15][16] some of which are the inhibitors of PDHc E1.…”

Section: Introductionmentioning

confidence: 99%

Separation and aquatic toxicity of enantiomers of 1‐(substituted phenoxyacetoxy)alkylphosphonate herbicides

Zhou

Zhao

et al. 2007

Chirality

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A series of organophosphorous compounds (OPs), 1-(substituted phenoxyacetoxy)alkylphosphonates containing a chiral carbon atom, show notable herbicidal activities. In this study, the enantioselective separation and biological toxicity of all these compounds were investigated. The enantioselective separation on the columns of Chiralpak AD, Chiralpak AS, Chiralcel OD, and Chiralcel OJ were compared under various chromatographic conditions. All the analytes investigated obtained baseline resolution (R(s) > 1.5) on Chiralpak AD column, which showed best chiral separation capacity. Further investigation was carried out on Chiralpak AD to evaluate the influence of the mobile phase composition and column temperature. The effect of the structural features on discrimination was also examined. The resolved enantiomers were distinguished by their signs of circular dichroism. The acute aquatic toxicity of enantiomers and racemate to Daphnia magna (D. magna) were assessed. The in vivo assays showed that compound 3 was about 2-148.5 times more toxic than the other four analogues to D. magna. The racemates of compounds 3 and 5 showed intermediate toxicity compare to their enantiomers, while those of compounds 1, 2, and 4 showed synergistic or antagonistic effect. These results suggest that the biological toxicity of chiral OPs to nontarget organisms is enantioselective and therefore should be evaluated with their pure enantiomers.

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“…[56][57][58] Recently, enantiomeric separation and quantification of various chiral pesticides by highperformance liquid chromatography and capillary electrophoresis have been reported by various researchers. [59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75] The general advantages of ICP-MS detection for chiral pesticide determinations in complex environmental samples have been reported. 76) Scientists determined the S and R isomers of metolachlor (3) in water by enantioselective enzyme immunoassay.…”

Section: Chiral Separationsmentioning

confidence: 99%

Chiral pesticides

Sekhon

2009

J. Pestic. Sci.

106

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The enantiomers of chiral pesticides are often metabolized at different rates. In agriculture, the preferred chiral form of a pesticide is more effective at lower application rates or more specific toward a targeted pest. Other advantages of chiral pure pesticides include greater environmental safety, reduced cost, greater specificity and extended patent life. Recent progress in optical resolution, asymmetric synthesis and biocatalysis of chiral pesticides has been described. Techniques to separate enantiomers with chiral HPLC and GC columns, electrophoresis and mass spectrometry have been reported. Chiral chase is actively pursuing asymmetric hydrogenation for the manufacture of a pure single-enantiomer pesticide. Enantioselectivity occurs in pesticidal activities toward target organisms as well as non-targeted organisms. There is a need to characterize both enantiomers of chiral pesticides in order to have an accurate understanding of their distribution and fate in the environment. Enantiomeric analysis can be useful in this aim and this is an important consideration in the risk assessment of pesticides. Use of only the target-active enantiomer of pesticides should be encouraged as it will reduce the pollutant load, provided it has no adverse impact on non-target organisms.

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Separation and aquatic toxicity of enantiomers of the organophosphorus insecticide trichloronate

Cited by 49 publications

References 15 publications

Separation and toxicity of salithion enantiomers

Separation and toxicity of salithion enantiomers

Separation and aquatic toxicity of enantiomers of 1‐(substituted phenoxyacetoxy)alkylphosphonate herbicides

Chiral pesticides

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