Stereoselective uptake and distribution of the chiral neonicotinoid insecticide, Paichongding, in Chinese pak choi (Brassica campestris ssp. chinenesis)

Wang, Haiyan; Liu, Ruyang; Fu, Qiuguo; Zhang, Sufen; Cai, Zhiqiang; Li, Juying; Zhao, Xiao‐Jun; Ye, Qingfu; Wang, Wei; Li, Zhong

doi:10.1016/j.jhazmat.2013.09.054

Cited by 32 publications

(21 citation statements)

References 37 publications

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“…21 Wang et al found that after foliar application, no stereoselective absorption was observed among the enantiomers of paichongding, whereas significant stereoselective translocation in plants was observed between its epimers. 11 Thus, information on the stereoselective degradation and environmental behavior of paichongding as well as its metabolites (e.g., the metabolic pathways) is crucial for assessing environmental and human health safety. The objective of this study was to elucidate the degradation pathways of paichongding in soil, with an emphasis on the identification of incomplete degradation products and stereoselective degradation, by using 14 C labeling and LC-MS/MS.…”

Section: ■ Introductionmentioning

confidence: 99%

Stereoselective Degradation and Transformation Products of a Novel Chiral Insecticide, Paichongding, in Flooded Paddy Soil

Zhang

et al. 2016

J. Agric. Food Chem.

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Paichongding is a chiral neonicotinoid insecticide currently marketed as racemate against sucking and biting insects. Under anaerobic condition, all paichongding stereoisomers underwent appreciable degradation in soil during 100 days of incubation, with estimated t values between 0.18 and 3.15 days. Diastereoselectivity in paichongding degradation was observed, with enantiomers (5S,7R)- and (5R,7S)-paichongding being more preferentially degraded in soils than enantiomers (5R,7R)- and (5S,7S)-paichongding. The half-lives of (5R,7R)- and (5S,7S)-paichongding were 3.05 and 3.15 days, respectively, as compared to 0.18 day for (5R,7S)- and (5S,7R)-paichongding. A total of nine intermediates were identified, of which depropylated paichongding was the predominant metabolite and appeared to be stable and recalcitrant to further degradation. Paichongding is degraded via denitration, depropylation, nitrosylation, demethylation, hydroxylation, and enol-keto tautomerism, producing chiral and biologically active products. These findings could have implications for environmental risk and food safety evaluations.

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Section: ■ Introductionmentioning

confidence: 99%

Stereoselective Degradation and Transformation Products of a Novel Chiral Insecticide, Paichongding, in Flooded Paddy Soil

Zhang

et al. 2016

J. Agric. Food Chem.

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“…Paichongding (IPP, 1-((6-chloropydidin-3-yl) methyl)-7-methyl-8-nitro-5propoxy-1,2,3,5,6,7-hexahydroimidazo[1, 2-α-]-pyridine) is a novel nitromethylene neonicotinoid recently developed by the East China University of Science and Technology in China (Zhao et al 2010;Fu et al 2013a, b;Li et al 2013;Wang et al 2013;Zhang et al 2013;Cai et al 2015b). IPP is different from the traditional neonicotinoids as it is the antagonist of the postsynaptic nicotinic acetylcholine receptors (nAChRs) of insects.…”

Section: Introductionmentioning

confidence: 99%

“…Several reports have mainly focused on its photodegradation in aqueous solution, translocation in Youdonger (Brassica campestris subsp. Chinensis, Chinese cabbage), IPP metabolism, extractable and bound residue, and transformation in soils (Zhao et al 2010;Fu et al 2013a, b;Li et al 2013;Wang et al 2013;Zhang et al 2013;Cai et al 2015b, c). The effect of IPP on soil microbial communities in aerobic soils has not been reported until now.…”

Section: Introductionmentioning

confidence: 99%

Impact of the novel neonicotinoid insecticide Paichongding on bacterial communities in yellow loam and Huangshi soils

Cai

Wang

et al. 2015

Environ Sci Pollut Res

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Insecticides are widely sprayed in modern agriculture for ensuring the crop yield, which could also lead to contamination and insecticide residue in soils. Paichongding (IPP) is a novel neonicotinoid insecticide and was developed recently in China. Soil bacterial community, diversity, and community composition vary widely depending on environmental factors. As for now, little is known about bacterial species thriving, bacterial community diversity, and structure in IPP-spraying soils. In present study, IPP degradation in yellow loam and Huangshi soils was investigated, and bacterial communities and diversity were examined in soil without IPP spray and with IPP spray through pyrosequencing of 16S ribosomal RNA (rRNA) gene amplicons. The degradation ratio of IPP at 60 days after treatment (DAT) reached 51.22 and 34.01 % in yellow loam and Huangshi soil, respectively. A higher richness of operational taxonomic units (OTUs) was found in yellow loam soil (867 OTUs) and Huangshi soil (762 OTUs) without IPP spray while OUTs were relatively low in IPP-spraying soils. The community composition also differed both in phyla and genus level between these two environmental conditions. Proteobacteria, Firmicutes, Planctomycetes, Chloroflexi, Armatimonadetes, and Chlorobi were stimulated to increase after IPP application, while IPP inhibited the phyla of Bacteroidetes, Actinobacteria, and Acidobacteria.

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“…Of a list of 1,693 pesticides compiled by Ulrich et al [4], 482 (28%) were found to be chiral. Since it is well known that chiral pesticide enantiomers can differ greatly in their biological efficacy, toxicity, and environmental fate, improving the existing knowledge on the enantioselectivity of processes determining the fate of chiral pesticides in the environment is considered a current research opportunity [5][6][7][8]. Despite this, many studies on chiral pesticides do not yet explicitly account for individual stereoisomers, implicitly and incorrectly assuming that enantiomers have identical environmental behavior [9,10].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective sorption of the chiral fungicide metalaxyl on soil from non-racemic aqueous solutions: Environmental implications

Celis

Gámiz

Facenda

et al. 2015

Journal of Hazardous Materials

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Mechanisms governing the enantioselectivity of the processes that determine the behavior of chiral pollutants in the environment need to be better understood. Understanding these mechanisms should help improve predictions of the hazards and risks chiral compounds can pose to people and the environment. We report the results of batch sorption experiments indicating that the sorption of the chiral fungicide metalaxyl on soil from non-racemic initial solutions was enantioselective. While from a racemic initial solution the two enantiomers of metalaxyl were sorbed on the soil to the same extent, increasing the fraction of R-enantiomer in the initial solution led to enhanced sorption of this enantiomer and to reduced sorption of the S-enantiomer. Considering the shape of the sorption isotherms (S-type) and the sorption behavior of model sorbents, we attributed this effect to molecular interactions between metalaxyl enantiomer species at the sorbed state, where R-R metalaxyl interactions appeared to be more favorable than R-S metalaxyl interactions. We discuss important environmental implications of the proposed mechanism, such as those related to the fact that the biological degradation of metalaxyl is known to be an enantioselective process that can yield non-racemic residues in soils shortly after application of the fungicide as a racemic mixture.

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Stereoselective uptake and distribution of the chiral neonicotinoid insecticide, Paichongding, in Chinese pak choi (Brassica campestris ssp. chinenesis)

Cited by 32 publications

References 37 publications

Stereoselective Degradation and Transformation Products of a Novel Chiral Insecticide, Paichongding, in Flooded Paddy Soil

Stereoselective Degradation and Transformation Products of a Novel Chiral Insecticide, Paichongding, in Flooded Paddy Soil

Impact of the novel neonicotinoid insecticide Paichongding on bacterial communities in yellow loam and Huangshi soils

Enantioselective sorption of the chiral fungicide metalaxyl on soil from non-racemic aqueous solutions: Environmental implications

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