Zinc-mediated reactions on salicylaldehyde for Botrytis cinerea control

Franche, Antoine; Imbs, Claire; Fayeulle, Antoine; Merlier, Franck; Billamboz, Muriel; Léonard, Estelle

doi:10.1016/j.cclet.2019.08.053

Cited by 11 publications

(7 citation statements)

References 29 publications

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“…Figure 6 also illustrates one exemplary reaction from this cluster. 53 A similar trend, but less marked, is detectable for titanium, which promoted the same reaction types. This observation may signify that these two metals are often employed to catalyze the same class of reactions, in some cases even as a combination.…”

Section: Chemical Science Accepted Manuscriptmentioning

confidence: 80%

Navigating chemical reaction space – application to DNA-encoded chemistry

et al. 2022

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Section: Chemical Science Accepted Manuscriptmentioning

confidence: 80%

Navigating chemical reaction space – application to DNA-encoded chemistry

et al. 2022

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“…Botrytis cinerea is a commercially necrotrophic pathogenic fungus, affecting devastating diseases and significant crop losses in a wide variety of plant species. 1,2 The complex interactions between this necrotrophic pathogenic fungus, the plants it infects, and significant crop losses caused by B. cinerea on over 1400 species of cultivated plants attract particular attention from the main global agrochemical researchers and companies. 3 Pyrazole carboxamide derivatives showed a broad spectrum of antifungal activities as the succinate dehydrogenase inhibitor (SDHI), 4−7 and some of them reached the market in the past decade, such as penthiopyrad, penflufen, sedaxane, bixafen, fluxapyroxad, and pydiflumetofen (Scheme 1A).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Pathogenic fungus has been regarded as a worldwide threat for plant growth and food security. Botrytis cinerea is a commercially necrotrophic pathogenic fungus, affecting devastating diseases and significant crop losses in a wide variety of plant species. , The complex interactions between this necrotrophic pathogenic fungus, the plants it infects, and significant crop losses caused by B. cinerea on over 1400 species of cultivated plants attract particular attention from the main global agrochemical researchers and companies …”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Pyrazole Carboxylate Derivatives Containing Thiazole as Potential Fungicides

Xia

Cheng

Liu

et al. 2021

J. Agric. Food Chem.

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Inspired by commercially established fluxapyroxad as the lead compound of novel efficient antifungal ingredients, novel pyrazole carboxylate derivatives containing a flexible thiazole backbone were successfully designed, synthesized, and detected for their in vitro and in vivo biological activities against eight agricultural fungi. The antifungal bioassay results showed that compound 24 revealed excellent bioactivities against Botrytis cinerea and Sclerotinia sclerotiorum, with median effective concentrations (EC 50 ) of 0.40 and 3.54 mg/L, respectively. Compound 15 revealed remarkable antifungal activity against Valsa mali, with an EC 50 value of 0.32 mg/L. For in vivo fungicide control against B. cinerea and V. mali, compounds 3 and 24 at 25 mg/L, respectively, displayed prominent efficacy on cherry tomatoes and apple branches. Molecular docking results demonstrated that compound 15 could form an interaction with several crucial residues of succinate dehydrogenase (SDH), and the in vitro enzyme assay indicated that the target compound 15 displayed an inhibitory effect toward SDH, with an IC 50 value of 82.26 μM. The experimental results indicated that phenyl pyrazole carboxylate derivatives displayed a weak antifungal property and low activity compared to the other title substituent pyrazole carboxylate derivatives. Compounds 3, 15, and 24 are promising antifungal candidates worthy of further fungicide development due to their prominent effectiveness.

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“…Thanks to their numerous biological activities and their ability to permeate the skin, monoterpenes and monophenols constitute a significant part of the whole group of the aforementioned secondary metabolites 9–12 . As a consequence, and following our continuous interest in developing new antimicrobial agents, 13–23 a selection of 20 natural terpenoid candidates have been selected as potential crop protection compounds against Z. tritici for in vitro evaluation. Among them, three subgroups can be defined: (i) terpenes, (ii) terpenoic alcohols and ethers, and (iii) phenolic derivatives (Table 1).…”

Section: Introductionmentioning

confidence: 99%

Sesamol‐based terpenoids as promising bio‐sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici

Damiens

Léonard

Fayeulle

et al. 2021

Pest Management Science

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BACKGROUND Research into environmentally friendly alternatives to conventional plant protection products, to promote sustainable agriculture and healthy food, is strongly encouraged. RESULTS In this context, 20 naturally occurring terpenoids and phenolic compounds were selected and evaluated in vitro as crop protection compounds against Zymoseptoria tritici, the causal agent of Septoria tritici blotch of wheat. After selection of the most active compounds, some hemisynthetic modifications were conducted to modify their lipophilicity. These modifications led to the discovery of sesamol esters as promising antifungal agents, with IC50 around 10 μg/mL and a total absence of cytotoxicity against human cells. CONCLUSION These sesamol‐based derivatives should be selected for further evaluations in planta to validate their use as wheat crop protection agents. Moreover, the importance of a balanced hydrophily/lipophilicity ratio should be further studied. © 2021 Society of Chemical Industry

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Zinc-mediated reactions on salicylaldehyde for Botrytis cinerea control

Cited by 11 publications

References 29 publications

Navigating chemical reaction space – application to DNA-encoded chemistry

Navigating chemical reaction space – application to DNA-encoded chemistry

Discovery of Novel Pyrazole Carboxylate Derivatives Containing Thiazole as Potential Fungicides

Sesamol‐based terpenoids as promising bio‐sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici

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