Synthesis and insecticidal activity of novel 1,2,4-triazole derivatives containing trifluoroacetyl moieties

Zhao, Fenghai; Tang, Xianjun; Liu, Min; Qin, Z. H.; Li, Jiaqi; Xiao, Yumei

doi:10.1007/s11030-021-10321-4

Cited by 6 publications

(6 citation statements)

References 25 publications

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“…At a concentration of 500 mg/L, the insecticidal activity of compound 98 against Aphis gossypii was 96.4% [113]. At 100 mg/L concentration, the activity of compounds 99–101 against Nilaparvata lugens were 93.5%, 94.1%, and 95.5%, respectively [114]. At a concentration of 500 mg/L, compounds 102–104 showed good insecticidal activity against Aphis fabae , with a fatality rate of more than 80% [115].…”

Section: Insecticidal Activitymentioning

confidence: 99%

Research progress of triazole derivatives in the discovery of agricultural chemicals

Song,

Wang,

Cai

et al. 2023

Journal of Heterocyclic Chem

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Triazole groups play an important role in the construction of agricultural bioactive molecules, often acting as linking units to organically graft different pharmacophore groups, so as to obtain efficient and broad‐spectrum pesticide molecules. After decades of development, triazole derivatives have made remarkable achievements in the discovery of pesticides, especially the discovery of fungicides. In addition, highly effective triazole insecticides, herbicides, and anti‐plant virus agents have also been found, and commercial triazole pesticides have occupied a large market share. At present, the study of triazole compounds has become one of the important fields in the development of new pesticides. We systematically reviewed the application of triazole derivatives in the discovery of new pesticides since 2010, summarized the antifungal, antibacterial, insecticidal, herbicidal, and anti‐plant virus activities of triazole derivatives, and discussed the structure–activity relationship and mechanism of action in order to provide inspiration and ideas for the discovery of new triazole agrochemicals.

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Section: Insecticidal Activitymentioning

confidence: 99%

Research progress of triazole derivatives in the discovery of agricultural chemicals

Song,

Wang,

Cai

et al. 2023

Journal of Heterocyclic Chem

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“…4,5 Triazole is a kind of five-membered heterocyclic compounds containing three N atoms, 6 which have a high electron cloud density. Thus, it also exhibits excellent insecticidal, 7 herbicidal, 8 antifungal, 9 antibacterial, 10 antiglycating, 11 and antiepileptic 12 activities.…”

Section: ■ Introductionmentioning

confidence: 99%

“…What is exciting is that rosin-based derivatives have the advantages of environmental compatibility and low toxicity, so the development of rosin-based derivates aroused widespread concern among scientific researchers. , Triazole is a kind of five-membered heterocyclic compounds containing three N atoms, which have a high electron cloud density. Thus, it also exhibits excellent insecticidal, herbicidal, antifungal, antibacterial, antiglycating, and antiepileptic activities.…”

Section: Introductionmentioning

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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“…Nitrogen-containing heterocyclic compounds with high biological activities are considered as important pharmaceutical or pesticide intermediates. , Among them, triazole compounds that contain a high electron cloud density at the three N atoms of their rings also have high antifungal, insecticidal, herbicidal, and other agricultural biological activities. , Since Bayer AG reported the first commercial triazole fungicide-triazolone in 1973, triazole scaffolds have become widely used as pesticides. − In addition, thiophene heterocycle and a Schiff-based group are reported to have extensive antifungal activities, as thiophene heterocycle contains a S atom and the Schiff-based group (CN) contains N atoms; both S and N atom contain lone pair electrons, which can easy to form interactions with amino acid residues, resulting in lethal effect. − …”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Antifungal Candidates Containing Triazole Scaffold from Natural Rosin against Valsa mali for Crop Protection

Chen

et al. 2023

J. Agric. Food Chem.

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Two series of dehydroabietyl-1,2,4-triazole-4-Schiff-based derivatives were synthesized from rosin to control plant fungal diseases. In vitro evaluation and screening of the antifungal activity were performed using Valsa mali, Colletotrichum orbiculare, Fusarium graminearum, Sclerotinia sclerotiorum, and Gaeumannomyces graminis. Compound 3f showed excellent fungicidal activity against V. mali (EC50 = 0.537 μg/mL), which was significantly more effective than the positive control fluconazole (EC50 = 4.707 μg/mL). Compound 3f also had a considerable protective effect against V. mali (61.57%–92.16%), which was slightly lower than that of fluconazole (85.17–100%) at 25–100 μg/mL. Through physiological and biochemical analyses, the preliminary mode of action of compound 3f against V. mali was explored. Ultrastructural observation of mycelia showed that compound 3f hindered the growth of the mycelium and destroyed the ultrastructure of V. mali seriously. Conductivity analysis and laser scanning confocal microscope staining showed that compound 3f changed cell-membrane permeability and caused accumulation of reactive oxygen species. The enzyme activity results showed that compound 3f significantly inhibited the activity of CYP51 (59.70%), SOD (76.9%), and CAT (67.86%). Molecular docking identified strong interaction energy between compound 3f and crystal structures of CYP51 (−11.18 kcal/mol), SOD (−9.25 kcal/mol), and CAT (−8.79 kcal/mol). These results provide guidance for the discovery of natural product-based antifungal pesticide candidates.

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Synthesis and insecticidal activity of novel 1,2,4-triazole derivatives containing trifluoroacetyl moieties

Cited by 6 publications

References 25 publications

Research progress of triazole derivatives in the discovery of agricultural chemicals

Research progress of triazole derivatives in the discovery of agricultural chemicals

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

Design and Synthesis of Antifungal Candidates Containing Triazole Scaffold from Natural Rosin against Valsa mali for Crop Protection

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