Preparation of terpene-derived fungicidal candidates with a 1,3,4-thiadiazole moiety for natural product-inspired agrochemical discovery

Geng, Yuanxiao; Gui, Kuo; Pan, Tingmin; Ye, Jiuhui; Li, Jian; Feng, Juntao; Ma, Zhiqing; Lei, Peng; Gao, Yanqing

doi:10.1016/j.indcrop.2022.115889

Cited by 6 publications

(5 citation statements)

References 26 publications

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“…citricolor pseudopilei was not established, and the effects of 18 , 20 , 21 , 25 , 34, 36 , and 38 remain unknown. Nonetheless, some works report effective fungicidal effects using terpenes obtained from plants and fungi and some modified derivatives using the disc diffusion method, ,, as well as by adding the essential oils directly into the culture media where conidia from pathogenic fungi have been previously inoculated …”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the actual effect of this type of components on M. citricolor pseudopilei was not established, and the effects of 18, 20, 21, 25, 34, 36, and 38 remain unknown. Nonetheless, some works report effective fungicidal effects using terpenes obtained from plants and fungi and some modified derivatives using the disc diffusion method, 36,66,67 as well as by adding the essential oils directly into the culture media where conidia from pathogenic fungi have been previously inoculated. 68 Comparing the pseudopilei morphology under SEM, notable changes were observed on the surface of the apical portion when they were exposed to 1,8-dimethoxynaphthalene (37).…”

Section: ■ Introductionmentioning

confidence: 99%

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Differential Volatile Organic Compound Expression in the Interaction of Daldinia eschscholtzii and Mycena citricolor

Escudero-Leyva,

Quirós-Guerrero,

Vásquez-Chaves

et al. 2023

ACS Omega

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Fungi exhibit a wide range of ecological guilds, but those that live within the inner tissues of plants (also known as endophytes) are particularly relevant due to the benefits they sometimes provide to their hosts, such as herbivory deterrence, disease protection, and growth promotion. Recently, endophytes have gained interest as potential biocontrol agents against crop pathogens, for example, coffee plants (Coffea arabica). Published results from research performed in our laboratory showed that endophytic fungi isolated from wild Rubiaceae plants were effective in reducing the effects of the American leaf spot of coffee (Mycena citricolor). One of these isolates (GU11N) from the plant Randia grandifolia was identified as Daldinia eschscholtzii (Xylariales). Its antagonism mechanisms, effects, and chemistry against M. citricolor were investigated by analyzing its volatile profile alone and in the presence of the pathogen in contactless and dual culture assays. The experimental design involved direct sampling of agar plugs in vials for headspace (HS) and headspace solid-phase microextraction (HS-SPME) gas chromatography-mass spectrometry (GC-MS) analysis. Additionally, we used ultrahigh-performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-HRMS/MS) to identify nonvolatile compounds from organic extracts of the mycelia involved in the interaction. Results showed that more volatile compounds were identified using HS-SPME (39 components) than those by the HS technique (13 components), sharing only 12 compounds. Statistical tests suggest that D. eschscholtzii inhibited the growth of M. citricolor through the release of VOCs containing a combination of 1,8-dimethoxynapththalene and terpene compounds affecting M. citricolor pseudopilei. The damaging effects of 1,8-dimethoxynaphthalene were corroborated in an in vitro test against M. citricolor pseudopilei; scanning electron microscopy (SEM) photographs confirmed structural damage. After analyzing the UHPLC-HRMS/MS data, a predominance of fatty acid derivatives was found among the putatively identified compounds. However, a considerable proportion of features (37.3%) remained unannotated. In conclusion, our study suggests that D. eschscholtzii has potential as a biocontrol agent against M. citricolor and that 1,8-dimethoxynaphthalene contributes to the observed damage to the pathogen’s reproductive structures.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Differential Volatile Organic Compound Expression in the Interaction of Daldinia eschscholtzii and Mycena citricolor

Escudero-Leyva,

Quirós-Guerrero,

Vásquez-Chaves

et al. 2023

ACS Omega

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“…Effect of Co. 5h-1 on Defense Enzyme Activity. According to a method, 38 we measured the enzymatic activity of sterol 14 alphademethylase (CYP51), superoxide dismutase (SOD), peroxidase (POD), and catalase (CAT) using kits (Solarbio Science Co., Ltd., Beijing, China).…”

Section: Effect Of Co 5h-1 On Nucleus Reactive Oxygen Species (Ros) A...mentioning

confidence: 99%

Discovery of Potential Rosin-Based Triazole Antifungal Candidates to Control Valsa mali for Sustainable Crop Protection

Xu,

Han,

Lou

et al. 2024

J. Agric. Food Chem.

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To investigate the potential application value of dehydroabietic acid, 27 novel dehydroabietyl-1,2,4-triazole-5thioether-based derivatives were designed and characterized by IR, 1 H NMR, 13 C NMR, and LC-MS. Their antifungal activities were evaluated against five plant fungi, namely, Valsa mali, Colletotrichum orbiculare, Fusarium graminearum, Sclerotinia sclerotiorum, and Gaeumannomyces graminis; the results showed that compound 5h-1 (Co. 5h-1) exhibited a considerable inhibitory effect against V. mali. Moreover, in vivo experiments indicated that Co. 5h-1 had a certain protective effect on apple branches. The preliminary structure−activity relationship analysis suggested that the electron-withdrawing group on the benzyl group was significantly better than that of other substituent derivatives. Through electron microscopy analysis, it was found that Co. 5h-1 hindered the growth of mycelia, damaged their cell structure, and caused the large accumulation of reactive oxygen species (ROS). Preliminary research on the mode of action indicated that Co. 5h-1 could affect the activity of CAT by increasing the α-helix (0.790%), decreasing the βsheet (0.170%), which led to the accumulation of ROS. In addition, Co. 5h-1 also affected the activity of CYP51, hindered the biosynthesis of ergosterol, and increased cell membrane permeability. Overall, this above research proposed that Co. 5h-1 can be a novel leading structure for development of a fungicide agent.

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“…In order to alleviate the problems mentioned above, while in line with the concept of green development, high quality, and sustainable development, researchers have done a lot of scientific research. For example, the development of nanopreparations in fungicides could effectively improve the utilization rate, increase the efficacy of the original drug, and reduce the impact on the environment. , In addition, the discovery and fungicidal application of microbial pesticides, natural products, RNA interference, and polypeptides could also meet the needs of green development. − Furthermore, the development of new green ecological fungicides could also delay the increase of pathogen resistance. , Meanwhile, structural modification based on natural products has become an effective way to develop new green agrochemicals, such as natural strobilurin A-derived methoxyacrylate fungicides, natural cinnamic acid-derived dimethomorph, and so on. − At present, although commercial fungicides have various structures, the fungicidal targets are same for the similar structures, which results in the existence of cross-resistance. Therefore, the discovery of new pharmacophores and the exploration of new targets are also very important for the development of fungicides …”

Section: Summary and Future Prospectsmentioning

confidence: 99%

A Comprehensive Investigation of Hydrazide and Its Derived Structures in the Agricultural Fungicidal Field

Chang

Liu

Zhang

et al. 2023

J. Agric. Food Chem.

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Hydrazides are present in many bioactive molecules and exhibit a variety of biological activities, such as insecticidal, herbicidal, antifungal, antitumor, and antiviral effects. In this Review, we review the application of hydrazide and its derived structures in the agricultural fungicidal field, including monohydrazides, diacylhydrazines, hydrazide-hydrazones, and sulfonyl hydrazides. In addition, the antifungal mechanism of action of the hydrazide derivatives was analyzed and summarized, mainly involving succinate dehydrogenase inhibitors, laccase inhibitors, and targeting plasma membranes. Finally, based on the structural analysis of the novel fungicidal lead compounds, the structure−activity relationship of the hydrazide derivatives was constructed and the development trend of hydrazide structures in fungicidal applications was prospected. It is hoped that this Review can provide some significant guidance for the development of new hydrazide fungicides in the future.

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Preparation of terpene-derived fungicidal candidates with a 1,3,4-thiadiazole moiety for natural product-inspired agrochemical discovery

Cited by 6 publications

References 26 publications

Differential Volatile Organic Compound Expression in the Interaction of Daldinia eschscholtzii and Mycena citricolor

Differential Volatile Organic Compound Expression in the Interaction of Daldinia eschscholtzii and Mycena citricolor

Discovery of Potential Rosin-Based Triazole Antifungal Candidates to Control Valsa mali for Sustainable Crop Protection

A Comprehensive Investigation of Hydrazide and Its Derived Structures in the Agricultural Fungicidal Field

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