Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity

Li, Ziliang; Cong, Yun-Bo; Ma, Xiaojuan; Wei, Zhenyun; Cheng, Chun‐Sheng; Shi, Fa‐Nian; Li, Sanxi

doi:10.1002/ps.5928

Cited by 7 publications

(5 citation statements)

References 16 publications

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“…Besides, enantioselective bioactivity can be found in other chiral pesticides. Li et al found that (3 S ,5 R )-pyrisoxazole showed higher fungicidal activity than the other three isomers tested . Gao et al found that the fungicidal activity of R -oxathiapiprolin was 2.49–13.30 times greater than that of S -oxathiapiprolin .…”

Section: Resultsmentioning

confidence: 99%

“…Li et al found that (3S,5R)-pyrisoxazole showed higher fungicidal activity than the other three isomers tested. 32 Gao et al found that the fungicidal activity of R-oxathiapiprolin was 2.49−13.30 times greater than that of S-oxathiapiprolin. 33 In the realm of agricultural management, greater emphasis should be placed on the utilization of more effective enantiomers.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Screening for a Fenpropidin Enantiomer with High Activity and Low Toxicity

Li,

Zhao,

Zhou

et al. 2023

J. Agric. Food Chem.

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Fenpropidin has been extensively used for managing fungal diseases in different crops. There is a lack of literature on the enantioselective bioactivity and toxicity of fenpropidin. This study aims to explore the enantioselective bioactivity and toxicity of fenpropidin. R-Fenpropidin exhibited more potent bioactivity against seven plant pathogens than S-fenpropidin. R-Fenpropidin was more effective than S-fenpropidin in inhibiting sclerotial production, affecting mycelial growth and morphology, increasing cell membrane permeability, and decreasing the ergosterol content of Rhizoctonia solani. R-Fenpropidin exhibited a tighter binding affinity and formed hydrogen bonds with two target proteins. Fenpropidin also has enantioselective toxicity to Selenastrum capricornutum, with the toxicity of S-fenpropidin being seven times that of R-fenpropidin. S-Fenpropidin significantly reduced the content of the photosynthetic pigments. The results showed that R-fenpropidin was a highly active enantiomer with low toxicity. This study can provide a basis for the development of enantiomers with high activity and low toxicity.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Screening for a Fenpropidin Enantiomer with High Activity and Low Toxicity

Li,

Zhao,

Zhou

et al. 2023

J. Agric. Food Chem.

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“…XRD patterns were recorded utilizing a single-crystal X-ray diffractometer on a SuperNova CCD, operated at 0.8 mA and 50 kV employing Mo Kα radiation at 296.15 K. The constructions were resolved through a direct approach applying SHELXS and polished on F2 through full-matrix least-squares employing SHELXL [17]. Refinement details and crystallographic parameters are listed in Table S1.…”

Section: X-ray Crystallographic Analysismentioning

confidence: 99%

Study on the process of simultaneous oxidation of acyl chloride of novel insecticide tetrachlorantraniliprole using in situ FTIR

Cong¹,

Li²,

Hao³

et al. 2022

ScienceAsia

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The novel insecticide tetrachlorantraniliprole was synthesized utilizing 2,3,5-trichloropyridine as the starting material by a six-step route in 18% yield. The process of simultaneous oxidation and acyl chlorination was studied by in situ FTIR. The molecular structure of tetrachlorantraniliprole was identified by means of NMR, IR, MS, and X-ray diffraction analyses. The single crystal of tetrachlorantraniliprole was formed from toluene solvent, and exhibited monoclinic P2 1 /n group with crystal parameters of a = 15.3316(16) Å, b = 16.7139(16) Å, c = 19.6687(19) Å, V = 4835.2(8) Å 3 , and Z = 4. Moreover, its density = 1.605 g/m 3 , F(000) = 2328.0, µ = 2.17 mm −1 , and 26933 reflections were measured (2.992° 2θ 51.998°).

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“…7 Once neurologic symptoms appear, the mortality rate is almost 100%. 8 RABV is a single-stranded negative-chain RNA virus. The 12-kb genome encodes five structural proteins including nucleoprotein (N), matrix protein (M), phosphoprotein (P), glycoprotein (G), and RNA-dependent RNA polymerase (L).…”

Section: Introductionmentioning

confidence: 99%

The study of anti‐rabies virus effect of Shougong powder

Zhang,

Fan,

Wang

et al. 2024

VIEW

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Rabies is a lethal infectious disease caused by rabies virus (RABV). The mortality rate is very high after the appearance of clinical symptoms, with a survival rate of almost 0%. There is presently no cure for rabies. In the present study, we investigated whether the extract of Shougong powder—a calcium powder prepared from gecko that has demonstrated immunomodulatory properties in mice—is an effective treatment for rabies. The antiviral effects of the extract were evaluated both in vitro and in vivo with the cytotoxicity and antiviral assays and by immunofluorescence analysis, quantitative real‐time (qRT)‐PCR, and western blotting. The results showed that Shougong powder and its extract increased survival rate in RABV‐infected mice is up to 60% and 50%, respectively, even in 20 times of LD50, whereas the control groups treated with isoprinosine (IPS) or saline are only 20% and 0% survival (p = .011). qRT‐PCR and western blotting analyses showed that the extract strongly inhibited viral mRNA expression and protein synthesis in vitro: expression of the N, P, M, G, and L genes of RABV was decreased by 28.8%–45.0% in the IPS group (p < .05) and by 50.1%–59.0% in the extract group (p < .05) relative to the control group. These results demonstrate that Shougong powder has certain antiviral effects against RABV and can potentially be used for the treatment for rabies.

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Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity

Cited by 7 publications

References 16 publications

Screening for a Fenpropidin Enantiomer with High Activity and Low Toxicity

Screening for a Fenpropidin Enantiomer with High Activity and Low Toxicity

Study on the process of simultaneous oxidation of acyl chloride of novel insecticide tetrachlorantraniliprole using in situ FTIR

The study of anti‐rabies virus effect of Shougong powder

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