Stereoselective effects of chiral epoxiconazole on the metabolomic and lipidomic profiling of leek

Wang, Jishi; Zhao, Liuqing; Liu, Xiaowei; He, Zhimin

doi:10.1016/j.foodchem.2022.134962

Cited by 4 publications

(3 citation statements)

References 37 publications

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“…reported that chiral epoxiconazole had the enantioselective effect on the metabolome and lipidome of the target crop leek. The order of the degree of influence was (+)‐epoxiconazole > racemate epoxiconazole > (−)‐epoxiconazole 10 . Compared with a pair of enantiomers, the racemate triticonazole promoted the growth and development of wheat at the flowering stage, and improved the grain yield and processing quality 11 .…”

Section: Introductionmentioning

confidence: 99%

“…The order of the degree of influence was (+)-epoxiconazole > racemate epoxiconazole > (−)-epoxiconazole. 10 Compared with a pair of enantiomers, the racemate triticonazole promoted the growth and development of wheat at the flowering stage, and improved the grain yield and processing quality. 11 Therefore, exploring the impact of chiral pesticides on target crops can help guide the correct application of different enantiomers at the stereoselective level, and reduce the amount of chiral pesticides.…”

Section: Introductionmentioning

confidence: 99%

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Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato

Deng

et al. 2023

Pest Management Science

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BACKGROUND: In order to promote the green development of agriculture, it is important to study the enantioselective effect of chiral pesticides. The bioactivity of the chiral fungicide penthiopyrad (PEN) racemate and enantiomers against phytopathogens, toxicity to non-target organisms, effect on tomato fruit growth and maturation, and environmental fate in tomato cultivation were evaluated at an enantioselective level in this study. RESULTS:The results indicated that at the same efficacy, the optically pure S-(+)-PEN could lower the dosage of racemate by 20-96%. The S-enantiomer had low toxicity to earthworms. Besides, the S-(+)-PEN did not cause significant abiotic stress to the tomato and increased fruit fresh weight and size via modulating the contents of plant hormones. However, the content of hydrogen peroxide (H 2 O 2 ), superoxide (O 2 − ) and malondialdehyde in the R-enantiomer treatment group was significantly higher than the control group. The effect of the racemate on tomato fruit was between the enantiomers. Furthermore, compared to R-(−)-PEN and racemate, the S-enantiomer degraded more quickly in tomato fruit, leaves, and soil, reducing the danger of human exposure. CONCLUSION:The S-enantiomer is highly effective and less toxic. The development of enantiomer pure S-(+)-PEN products might be an efficient and low-risk strategy. The results lay the foundation for comprehensive evaluation and proper application of PEN.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato

Deng

et al. 2023

Pest Management Science

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“…In this paper, the synthesis of epoxiconazole was chosen as a typical indirect epoxidation of highly hindered substituted olefins. Epoxiconazole is a famous broad-spectrum fungicide commonly used in agricultural production and its effect inhibits synthesizing pathogenic ergosterol and hinders the pathogenic cell wall from forming . It is an effective preventative measure against leaf spots, mildew, and spotting for bananas, green onions, garlic, celery, kidney beans, melons, asparagus, peanuts, sugar beets, and other crops. , The indirect epoxidation synthesis of fluconazole is carried out using triazolene as the raw material, using hydrogen peroxide and maleic anhydride to react to generate peroxy acid for epoxidation, as shown in Scheme .…”

Section: Introductionmentioning

confidence: 99%

Study on Reaction Mechanism and Process Safety for Epoxidation

Cheng,

Wei,

Ming

et al. 2023

ACS Omega

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The reaction mechanism and process safety for epoxidation were investigated in this study. 1-(2-Chlorophenyl)-2-(4-fluorophenyl)-3-(1,2,4-triazole) propene (triazolene), a typical representative of high steric olefinic compounds, was chosen as the raw material. In addition, hydrogen peroxide was chosen as the oxygen source in the reaction. Online Raman spectroscopy combined with high-performance liquid chromatography (HPLC) was used for the process monitoring analysis. The results of this study indicated that the epoxidation process is exothermic, and the apparent reaction heat was 1340.0 kJ·kg –1 (measured by the mass of triazolene). The heat conversion rate was 39.7% immediately after hydrogen peroxide dosing to a triazolene and maleic anhydride mixture solution in chloroform. This result indicated that a considerable amount of heat is accumulated during the epoxidation reaction, which leads to a potential high safety concern. The study of the reaction mechanism showed that maleic anhydride reacts with hydrogen peroxide quickly to form maleic acid peroxide, which is controlled by hydrogen peroxide feeding, and the formed maleic acid peroxide further reacts with triazolenes slowly, which is a kinetically controlled reaction. Decomposition kinetics studies revealed that the temperatures corresponding to the time of maximum reaction rate for 8 and 24 h are T D24 = 89.9 °C and T D8 = 104.1 °C, respectively.

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Comprehensive effects of thiamethoxam from contaminated soil on lettuce growth and metabolism

Li,

Yin,

Kang

et al. 2024

Environmental Pollution

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Stereoselective effects of chiral epoxiconazole on the metabolomic and lipidomic profiling of leek

Cited by 4 publications

References 37 publications

Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato

Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato

Study on Reaction Mechanism and Process Safety for Epoxidation

Comprehensive effects of thiamethoxam from contaminated soil on lettuce growth and metabolism

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