Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Li, Shengkun; Li, Dangdang; Xiao, Taifeng; Zhang, Shasha; Song, Zehua; Ma, Hongyu

doi:10.1021/acs.jafc.6b03464

Cited by 91 publications

(95 citation statements)

References 22 publications

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“…In recent research, 1H‐pyrrole‐2‐carboxylic acid showed the significant activity of Pseudomonas by inhibiting QS and virulence determinants of P. aeruginosa PAO1 at the molecular level, which provides a useful scaffold for synthesis and construction of novel anti‐virulence drugs derived from natural sources (Ramadan et al ). A pyrrole compound developed by Syngenta, has been used for seed dressing and plant disease control (Li et al ). Amide compounds and their derivatives have attracted widespread attention in relation to their bacteriostasis and insecticidal aspects.…”

Section: Discussionmentioning

confidence: 99%

Identification of antimicrobial metabolites produced by a potential biocontrol Actinomycete strain A217

Hao

Zhou

et al. 2020

J Appl Microbiol

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Aims To extract and identify the metabolites of strain A217 as well as its antifungal spectrum and control effect on various plant pathogens. Methods and Results Strain A217 was identified as a Streptomyces sp. which was most similar to Streptomyces lienomycini. An antimicrobial spectrum test indicated that strain A217 inhibited several plant pathogenic fungi and strong antibacterial effect such as Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, Fusarium oxysporum, Pseudomonas syringae and Xanthomonas campestris. An in vivo tissue test demonstrated that the fermentation broth of strain A217 exerted therapeutic and protective effects of 49·47 and 61·60% respectively, on S. sclerotiorum. Additionally, the fermentation broth of A217 exerted control effects on walnut black spot disease in walnut leaves and branches amounting to 79·33 and 81·52% respectively. In a pot experiment, the fermentation broth exhibited a stronger protective and control effect (68·29%), as well as better bacteriostatic and disease control effects on Phytophthora blight of pepper, compared with Metalaxyl. Compounds possessing antifungal and antibacterial activities were obtained from the fermentation broth of strain A217, using column chromatography and HPLC. Chemical and structural analyses conducted using MS and nuclear magnetic resonance confirmed that these compounds were 1H‐pyrrole‐2‐carboxylic acid and 1H‐pyrrole‐2‐carboxamide. The EC50 values of compound 1H‐pyrrole‐2‐carboxylic acid1 for S. sclerotiorum and P. capsici were 20·13 and 50·36 μg ml−1 respectively. Compound 1H‐pyrrole‐2‐carboxamide2 showed significant antibacterial activity against different plant pathogenic bacteria. The MIC values of P. syringae, X. campestris and X. campestris pv. jugiandis were 7·5, 30 and 15·0 μg ml−1 respectively. Conclusions Actinomyces A217 fermentation products have a broad spectrum of bacteriostasis, and have good bacteriostasis activity to many plant pathogenic fungi and bacteria. Significance and Impact of the Study The present study revealed a new antimicrobial producing strain of Streptomyces and its potential application as a biological control agent for plant diseases.

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Section: Discussionmentioning

confidence: 99%

Identification of antimicrobial metabolites produced by a potential biocontrol Actinomycete strain A217

Hao

Zhou

et al. 2020

J Appl Microbiol

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“…The in vivo antifungal activity was determined on tomato fruits ( Lycopersicum esculentum ) infected by B. cinerea . Appropriate amounts of the tested compounds were dissolved in DMSO and then suspended in distilled water (containing 0.1% Tween 80) at a test concentration of 0.4 mg mL −1 .…”

Section: Methodsmentioning

confidence: 99%

“…The in vivo antifungal activity was determined on tomato fruits (Lycopersicum esculentum) infected by B. cinerea. 37 Appropriate amounts of the tested compounds were dissolved in DMSO and then suspended in distilled water (containing 0.1% Tween 80) at a test concentration of 0.4 mg mL −1 . Healthy fruits, which had been washed and treated with 75% aqueous ethanol in advance, were sprayed and the mixture evaporated under an ambient environment (∼ 28 ∘ C).…”

Section: In Vivo Antifungal Activitymentioning

confidence: 99%

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Wen

Jian

Shang

et al. 2018

Pest Management Science

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BACKGROUND Natural stilbenes (especially resveratrol and its derivatives) are well‐known phytoalexins that are active against many plant diseases. However, oxidative degradation and low bioavailability limit their exogenous application as fungicides on crops. In this study, a new class of resveratrol‐inspired thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit was synthesized and the derivatives' antifungal activities against phytopathogenic fungi were investigated. RESULTS The results revealed that compounds 5h and 5j exhibited improved antifungal activity against Botrytis cinerea with median effective concentrations (EC50) of 168.5 and 155.4 µg mL−1, respectively, which were superior to the EC50 of resveratrol (263.1 µg mL−1). Compound 5j was shown to effectively control disease development in B. cinerea‐infected tomatoes in vivo. Notably, considerably abnormal mycelial morphology and increased cell membrane conductivity were observed in the presence of compound 5j. CONCLUSION A new class of thiophene‐containing stilbene derivatives was designed and synthesized. Bioassay results showed that compound 5j exhibited promising antifungal activity, suggesting practical potential for fungal disease control. © 2018 Society of Chemical Industry

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“…Perhaps, this ‘de‐aromatization’ tends to optimize the hydrophobic moiety. Recently, the first exploration of chiral nicotinamides (boscalid analogues containing oxazolines) for the discovery of novel SDH‐inhibiting fungicides has been discussed . The SDH enzyme (succinate ubiquinone oxidoreductase; EC 1.3.5.1) is a mitochondrial hetero‐tetramer composed of four nuclear‐encoded subunits .…”

Section: Fungicidesmentioning

confidence: 99%

“…Recently, the first exploration of chiral nicotinamides (boscalid analogues containing oxazolines) for the discovery of novel SDH-inhibiting fungicides has been discussed. 51 The SDH enzyme (succinate ubiquinone oxidoreductase; EC 1.3.5.1) is a mitochondrial hetero-tetramer composed of four nuclear-encoded subunits. 52 The SDHA and SDHB subunits are exposed to the matrix of the mitochondria and SDHC and SDHD, which display a high degree of variation across species, are integral membrane proteins anchoring the SDHAB dimer to the integral membrane of the mitochondria.…”

Section: Fungicidal Succinate Dehydrogenase Inhibitorsmentioning

confidence: 99%

Current status of chirality in agrochemicals

Jeschke

2018

Pest Management Science

152

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The agrochemical industry is searching continuously for new pesticides to develop products that have optimal efficacy, lower application rates in the field, increased selectivity, favourable toxicological and environmental safety, enhanced user friendliness and better economic viability. One strategy by which to achieve these ambitious goals makes use of the unique properties of molecules containing asymmetric centres. In the past, many natural products and their congeners have been a source of inspiration in the design of new active ingredients, and the molecular structures of the resulting compounds have become increasingly complex; some 30% contain fragments with asymmetric centres. However, despite enormous progress in catalytic asymmetric processes over the past decade, few agrochemicals are produced in an enantiomerically pure or enriched form on an industrial scale. Since 2007, ∼ 43% of the 44 products launched (insecticides, acaricides, fungicides, nematicides and herbicides) contain one or more asymmetric centres in the molecule (∼ 47%) and most have been launched as racemic mixtures of enantiomers or diastereomers. This review provides an overview of the current status of chiral agrochemicals launched over the past 10 years and describes the inherently connected challenges of modern agricultural chemistry by managing important aspects resulting from the stereochemistry of these innovative products. © 2018 Society of Chemical Industry.

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Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Cited by 91 publications

References 22 publications

Identification of antimicrobial metabolites produced by a potential biocontrol Actinomycete strain A217

Identification of antimicrobial metabolites produced by a potential biocontrol Actinomycete strain A217

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Current status of chirality in agrochemicals

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