Thymol as an Interesting Building Block for Promising Fungicides against <i>Fusarium solani</i>

Eloy, Mariana Alves; Ribeiro, Rayssa; Meireles, Leandra Martins; Cutrim, Thiago Antonio de Sousa; Francisco, Carla Santana; Javarini, Clara L.; Borges, Warley de Souza; Costa, Adílson Vidal; Queiroz, Vagner Tebaldi de; Scherer, Rodrigo; Lacerda, Valdemar; Morais, Pedro Alves Bezerra

doi:10.1021/acs.jafc.0c07439

Cited by 8 publications

(2 citation statements)

References 54 publications

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“…Moreover, the 1,2,3-triazole nucleus can act as a pharmacophoric group, that is, the portion of the substance responsible for its biological activity. Thus, 1,2,3-triazole fragments have been introduced into the skeleton of numerous molecules, resulting in the discovery of compounds with important biological activities. − For example, the connection of 1,2,3-triazole and glycerol fragments resulted in triazole derivatives with significant fungicidal activity against Colletotrichum gloeosporioides. These derivatives showed efficacy compared to the commercial fungicide tebuconazole. , …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Lima

Teixeira

Moraes

et al. 2023

J. Agric. Food Chem.

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In agriculture, the control of fungal infections is essential to improve crop quality and productivity. This study describes the preparation and fungicidal activity evaluation of 12 glycerol derivatives bearing 1,2,3-triazole fragments. The derivatives were prepared from glycerol in four steps. The key step corresponded to the Cu(I)-catalyzed alkyne−azide cycloaddition (CuAAC) click reaction between the azide 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes (57−91% yield). The compounds were characterized by infrared spectroscopy, nuclear magnetic resonance ( 1 H and 13 C), and high-resolution mass spectrometry. The in vitro assessment of the compounds on Asperisporium caricae, that is, the etiological agent of papaya black spot, at 750 mg L −1 showed that the glycerol derivatives significantly inhibited conidial germination with different degrees of efficacy. The most active compound 4-(3-chlorophenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl) methyl)-1H-1,2,3-triazole (4c) presented a 91.92% inhibition. In vivo assays revealed that 4c reduced the final severity (70.7%) and area under the disease severity progress curve of black spots on papaya fruits 10 days after inoculation. The glycerol-bearing 1,2,3-triazole derivatives also present agrochemicallikeness properties. Our in silico study using molecular docking calculations show that all triazole derivatives bind favorably to the sterol 14α-demethylase (CYP51) active site at the same region of the substrate lanosterol (LAN) and fungicide propiconazole (PRO). Thus, the mechanism of action of the compounds 4a−4l may be the same as the fungicide PRO, blocking the entrance/ approximation of the LAN into the CYP51 active site by steric effects. The reported results point to the fact that the glycerol derivatives may represent a scaffold to be explored for the development of new chemical agents to control papaya black spot.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Lima

Teixeira

Moraes

et al. 2023

J. Agric. Food Chem.

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“…In common bean, persistent biotic pressures, such as the fungal pathogens Rhizoctonia solani, Pythium spp., Fusarium solani, and Fusarium oxysporum, are responsible for poor stand establishment and yield reductions. These pathogens are soilborne, and are generally controlled through fungicidal seed coatings, crop rotations, cultural management, and planting of resistant cultivars (Mohamed et al, 2016;Bartholomäus et al, 2017;Alves Eloy et al, 2021). Not all soil microorganisms are detrimental to host plants, however, and a growing number of beneficial plantassociated species have been identified.…”

Section: Introductionmentioning

confidence: 99%

Influence of organic plant breeding on the rhizosphere microbiome of common bean (Phaseolus vulgaris L.)

Park,

Nebert,

King

et al. 2023

Front. Plant Sci.

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IntroductionWe now recognize that plant genotype affects the assembly of its microbiome, which in turn, affects essential plant functions. The production system for crop plants also influences the microbiome composition, and as a result, we would expect to find differences between conventional and organic production systems. Plant genotypes selected in an organic regime may host different microbiome assemblages than those selected in conventional environments. We aimed to address these questions using recombinant inbred populations of snap bean that differed in breeding history.MethodsRhizosphere microbiomes of conventional and organic common beans (Phaseolus vulgaris L.) were characterized within a long-term organic research site. The fungal and bacterial communities were distinguished using pooled replications of 16S and ITS amplicon sequences, which originated from rhizosphere samples collected between flowering and pod set.ResultsBacterial communities significantly varied between organic and conventional breeding histories, while fungal communities varied between breeding histories and parentage. Within the organically-bred populations, a higher abundance of a plant-growth-promoting bacteria, Arthrobacter pokkalii, was identified. Conventionally-bred beans hosted a higher abundance of nitrogen-fixing bacteria that normally do not form functional nodules with common beans. Fungal communities in the organically derived beans included more arbuscular mycorrhizae, as well as several plant pathogens.DiscussionThe results confirm that the breeding environment of crops can significantly alter the microbiome community composition of progeny. Characterizing changes in microbiome communities and the plant genes instrumental to these changes will provide essential information about how future breeding efforts may pursue microbiome manipulation.

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Discovery of novel piperidine‐containing thymol derivatives as potent antifungal agents for crop protection

Yang,

Jiang,

Zhang

et al. 2024

Pest Management Science

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BACKGROUNDPlant fungal diseases pose a significant threat to crop production. The extensive use of chemical pesticides has led to growing environmental safety risks and pesticide resistance of various plant pathogens. Therefore, it is an urgent task to explore novel eco‐friendly fungicidal agents with high efficacy to combat fungal infection.RESULTSIn this study, we rationally designed a series of novel thymol derivatives by incorporation of the sulfonamide moiety and evaluated their biological activities against plant pathogenic fungi. The bioassay results underscored the remarkable in vitro antifungal activity of compounds 5m and 5t against Phytophthora capsici (P. capsici), with EC50 values of 8.420 and 8.414 μg/mL, respectively. Their efficacies were superior to that of widely used commercial fungicides azoxystrobin (AZO, 20.649 μg/mL) and cabendazim (CAB, 251.625 μg/mL). Furthermore, compound 5v exhibited excellent in vitro antifungal activity against Sclerotinia sclerotiorum (S. sclerotiorum), with an EC50 value of 12.829 μg/mL, significantly outperforming AZO (63.629 μg/mL). In vivo bioassays demonstrated the impactful activity of compound 5v against S. sclerotiorum, achieving over 98% curative and protective efficacies at the concentration of 200 μg/mL. Further mechanistic investigations unveiled that compound 5v induced mycelial shrinkage and collapse in S. sclerotiorum, resulting in organelle damage and the accumulation of antioxidant enzyme activity.CONCLUSIONThe significant antifungal efficacy of the prepared thymol derivatives shall encourage further exploration of compound 5v as a promising candidate to develop novel fungicides for crop protection. © 2024 Society of Chemical Industry.

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Thymol as an Interesting Building Block for Promising Fungicides against Fusarium solani

Cited by 8 publications

References 54 publications

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Influence of organic plant breeding on the rhizosphere microbiome of common bean (Phaseolus vulgaris L.)

Discovery of novel piperidine‐containing thymol derivatives as potent antifungal agents for crop protection

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