Synthesis and Fungicide Activity on<i>Asperisporium caricae</i>of Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Lima, Ângela; Teixeira, Róbson Ricardo; Moraes, Willian Bucker; Rocha, Matheus Ricardo da; Moraes, Arlan Figueiredo Carvalho; Gomes, Sâmela Cansi; Gazolla, Poliana; Silva, Silma Francielle; Queiroz, Vagner Tebaldi de; Fonseca, Victor R.; Romão, Wanderson; Morais, Pedro Alves Bezerra; Lacerda, Valdemar; Abreu, Lucas M.; Oliveira, Fabrício Marques de; Oliveira, Osmair Vital de; Costa, Adílson Vidal

doi:10.1021/acs.jafc.2c08941

Cited by 5 publications

(1 citation statement)

References 48 publications

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“…gloeosporioides. − , The relevance of triazoles in agricultural disease management extends to phytopathogen genera of global importance including Fusarium, Aspergillus, Corynespora, Pseudocercospora, and Asperisporum. Triazoles exhibit notable effectiveness against fungal diseases. − …”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Almeida lima,

Moreira,

Gazolla

et al. 2024

J. Agric. Food Chem.

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A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper(I)-catalyzed azide–alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. Triazoles 2k, 2m, 2l, and 2n, at 100 ppm, were the most effective, reducing mycelial growth by 88.3, 85.5, 82.4, and 81.4%, respectively. Molecular docking calculations allowed us to elucidate the binding mode of these derivatives in the catalytic pocket of C. gloeosporioides CYP51. The best-docked compounds bind closely to the heme cofactor and within the channel access of the lanosterol (LAN) substrate, with crucial interactions involving residues Tyr102, Ile355, Met485, and Phe486. From such studies, the antifungal activity is likely attributed to the prevention of substrate LAN entry by the 1,2,3-triazole derivatives. The triazoles derived from natural eugenol represent a novel lead in the search for environmentally safe agents for controlling C. gloeosporioides.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Almeida lima,

Moreira,

Gazolla

et al. 2024

J. Agric. Food Chem.

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Phytotoxic and Cytogenetic Assessment of Glycerol Triazole Derivatives in Model Plants and Weeds

de Assis Alves,

Gazolla

et al. 2024

Chemistry & Biodiversity

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Weed invasion represents a challenge for farmers, who typically manage it with herbicides. However, this approach raises concerns about environmental and human health, as well as increasing resistance in these plants with continued use. Therefore, exploring alternative methods, such as heterocyclic compounds, triazoles, is essential due to their biological and environmental relevance. This study aimed to evaluate the effects of twelve 1,2,3‐triazoles on the germination and early development of Lactuca sativa, Bidens pilosa, and Lolium multiflorum, as well as their impact on cell division in the cells of L. sativa. Triazole derivatives 4a, 4b, 4c, 4g, 4h, 4i, 4k, and 4l exhibited phytotoxicity, showing varying levels of inhibition in germination, germination speed index, and root growth. Chlorinated compounds were the most detrimental to lettuce development. B. pilosa was notably affected by compounds 4h, 4i, 4k, and 4l, while L. multiflorum responded most to triazoles 4c and 4l, with effectiveness comparable to that of the herbicide glyphosate. All derivatives, except 4l, exhibited aneugenic mechanisms of action, and 4a, 4b, 4c, 4e, 4f, and 4g showed clastogenic effects. This study demonstrated the potential of triazoles as effective agents against weed growth, with mechanisms that warrant further investigation for agricultural applications.

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1,2,4‐Triazole benzamide derivative TPB against Gaeumannomyces graminis var. tritici as a novel dual‐target fungicide inhibiting ergosterol synthesis and adenine nucleotide transferase function

Wang,

Song,

Cheng

et al. 2023

Pest Management Science

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BACKGROUNDIsopropyl 4‐(2‐chloro‐6‐(1H‐1,2,4‐triazol‐1‐yl)benzamido)benzoate (TPB) was a 1,2,4‐triazole benzoyl arylamine derivative with excellent antifungal activity, especially against Gaeumannomyces graminis var. tritici (Ggt). Its mechanism of action was investigated by transmission electron microscopy (TEM) observation, assays of sterol composition, cell membrane permeability, intracellular ATP and mitochondrial membrane potential, and mPTP permeability, ROS measurement, RNA sequencing (RNA‐seq) analysis.RESULTSTPB interfered with ergosterol synthesis, reducing ergosterol content, increasing toxic intermediates, and finally causing biomembrane disruption such as increasing cell membrane permeability and content leakage, and destruction of organelle membranes such as coarse endoplasmic reticulum and vacuole. Moreover, TPB destroyed the function of adenine nucleotide transferase (ANT), leading to ATP transport obstruction in mitochondria, inhibiting mPTP opening, inducing intracellular ROS accumulation and mitochondrial membrane potential loss, finally resulting in mitochondrial damage including mitochondria swelled, mitochondrial membrane dissolved, and cristae destroyed and reduced. RNA‐seq analyses showed that TPB increased the expression of ERG11, ERG24, ERG6, ERG5, ERG3 and ERG2 genes in ergosterol synthesis pathway, interfered with the expression of genes (NDUFS5, ATPeV0E, NCA2 and Pam17) related to mitochondrial structure, and inhibited the expression of genes (WrbA and GST) related to anti‐oxidative stress.CONCLUSIONSTPB exhibited excellent antifungal activity against Ggt by inhibiting ergosterol synthesis and destroying ANT function. So, TPB was a novel compound with dual‐target mechanism of action and can be considered a promising novel fungicide for the control of wheat Take‐all. The results provided new guides for the structural design of active compounds and powerful tools for pathogen resistance management. © 2023 Society of Chemical Industry.

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

Cited by 5 publications

References 48 publications

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Phytotoxic and Cytogenetic Assessment of Glycerol Triazole Derivatives in Model Plants and Weeds

1,2,4‐Triazole benzamide derivative TPB against Gaeumannomyces graminis var. tritici as a novel dual‐target fungicide inhibiting ergosterol synthesis and adenine nucleotide transferase function

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