Enantioselective Dissipation, Residue, and Risk Assessment of Diniconazole Enantiomers in Four Kinds of Fruits

Unreasonable application of pesticides may result in residues in the environment and foods. Chiral pesticides consist of two or more enantiomers, which may exhibit different behaviors. This Review intends to provide progress on the enantioselective residues of chiral pesticides in foods. Among the main chiral analytical methods, high performance liquid chromatography (HPLC) is the most frequently utilized. Most chiral pesticides are utilized as racemates; however, due to enantioselective dissipation, bioaccumulation, biodegradation, and chiral conversion, enantiospecific residues have been found in the environment and foods. Some chiral pesticides exhibit strong enantioselectivity, highlighting the importance of evaluation on an enantiomeric level. However, the occurrence characteristics of chiral pesticides in foods and specific enzymes or transport proteins involved in enantioselectivity needs to be further investigated. This Review could help the production of some chiral pesticides to single-enantiomer formulations, thereby reducing pesticide consumption as well as increasing food production and finally reducing human health risks.

Section: Cultivation Processmentioning

confidence: 96%

Section: ■ Cultivation Processmentioning

confidence: 99%

Enantioselective Behaviors of Chiral Pesticides and Enantiomeric Signatures in Foods and the Environment

Wang

Jiang

et al. 2023

“…Based on the supercritical fluid chromatographytandem mass spectrometry method, S-diniconazole was preferentially degraded in fruits. 13 The bioactivity of Smandipropamid was 118−592 times greater than that of Rmandipropamid against six plant pathogens. 14 S-Triticonazole had greater acute toxicity to non-target aquatic and terrestrial organisms.…”

Section: ■ Introductionmentioning

confidence: 96%

“…Many studies have reported a stereoselective phenomenon of chiral fungicides in environmental media and organisms. Based on the supercritical fluid chromatography-tandem mass spectrometry method, S -diniconazole was preferentially degraded in fruits . The bioactivity of S -mandipropamid was 118–592 times greater than that of R -mandipropamid against six plant pathogens …”

Section: Introductionmentioning

confidence: 99%

Enantioselective Degradation and Bioactivity Mechanism of a New Chiral Fungicide Fluindapyr in Paddy Ecosystems

Tong

Meng

et al. 2023

Fluindapyr is a novel chiral succinate dehydrogenase inhibitor used to control fungal diseases. The enantioselective effects of fluindapyr in paddy ecosystems are unknown. We developed a new chiral determination method of fluindapyr using ultrahigh performance liquid chromatography tandem mass spectrometry. The absolute configuration of the fluindapyr enantiomers was identified by an electron circular dichroism model. A new husk-based biochar material was used to optimize and establish a QuEchERs method for paddy soil determination. Under anaerobic conditions, the half-lives of R-fluindapyr and S-fluindapyr in paddy soil were 69.6 and 101.8 days, respectively. R-fluindapyr degraded more rapidly than S-fluindapyr. S-fluindapyr was 87.8 times more active against Rhizoctonia solani than R-fluindapyr. The enantioselective bioactivity mechanism was illustrated by molecular docking between the fluindapyr enantiomers and SDH of R. solani. The binding powers of R-fluindapyr and S-fluindapyr to proteins were −32.12 and − 42.91 kcal/mol, respectively. This study reports the stereoselectivity of fluindapyr about determination, degradation, bioactivity, and its mechanism. It provides a foundation for an in-depth study of fluindapyr at the enantiomer level.

“…In agricultural production, pesticides are widely used to control pathogenic bacteria, pests, and weeds to ensure high crop quality and yield and play a vital role in the development of human civilization. 1 As a new class of systematic fungicides developed in the past few years, succinate dehydrogenase inhibitors (SDHIs) can inhibit a wide variety of plant phytopathogenic fungi and have been widely used in biological control. 2 SDHI-type fungicides have attracted increasing attention because of their unique structure, high activity, and broad fungicidal spectrum.…”

Section: Introductionmentioning

confidence: 99%

Absolute Configuration, Enantioselective Bioactivity, and Mechanism Study of the Novel Chiral Fungicide Benzovindiflupyr

Chen

Xiang

Yuan

et al. 2023

Benzovindiflupyr has gained increasing attention as a new chiral succinate dehydrogenase inhibitor fungicide; however, its determination, bioactivity, and mechanism at the enantiomeric level are very limited. In the present study, optical rotation determination and X-ray single-crystal diffraction results identified that the absolute configurations were (+)-(1R,4S)-benzovindiflupyr and (−)-(1S,4R)-benzovindiflupyr. A quantitative determination method for enantiomers was established using high-performance liquid chromatography tandem mass spectrometry (HPLC–MS/MS) for pesticide detection. The stereoselective bioactivity assay indicated that (−)-(1S,4R)-benzovindiflupyr exhibited greater potency than (+)-(1R,4S)-benzovindiflupyr against seven phytopathogenic fungi. Molecular docking analysis showed that (−)-(1S,4R)-benzovindiflupyr possessed a stronger binding affinity to succinate dehydrogenase than (+)-(1R,4S)-benzovindiflupyr. The binding modes between enantiomers and the mutant with H272(B) predicted that the phytopathogenic fungi with H272(B) of succinate dehydrogenase mutation would not be resistant to benzovindiflupyr enantiomers. This study provides a basis for residue evaluation, risk assessment, and the safe application of benzovindiflupyr at the enantiomer level.