Synthesis, Herbicidal Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-Methyl- 1,2,4-triazole-thioether Compounds Containing Natural Styrene Structure

Li, Chengfei; Cen, Bo; Duan, Wengui; Lin, Guo‐Qiang; Wang, Xiu; Li, Baoyu

doi:10.6023/cjoc202011023

Cited by 6 publications

(7 citation statements)

References 27 publications

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“…According to the report (Li, Cen, et al 2021), the inhibitory rates of all title compounds against the root-growth of rape(Brassica campestris L.) and seedling growth of barnyard grass(Echinochloa crusgalli L.) were tested by the rape petri dish method and the barnyard grass beaker method, respectively. In brief, the compounds to be tested were emulsified by TW-80 at concentrations of 10 and 100 µg /mL.…”

Section: Herbicidal Activity Evaluationmentioning

confidence: 99%

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High value-added application of natural forest product α- pinene: design, synthesis and 3D-QSAR study of novel α- campholenic aldehyde-based 4-methyl-1,2,4-triazole-thioether compounds with significant herbicidal activity

Yin

et al. 2022

Natural Product Research

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For exploring novel natural product-derived herbicides, 16 novel α-campholenic aldehyde-based 4methyl-1,2,4-triazole-thioether compounds were designed, synthesized, and characterized by FT-IR, 1 H NMR, 13 C NMR, ESI-MS and elemental analysis. The preliminary bioassay showed that, at 100 µg/mL, most of the target compounds displayed significant inhibition activity against root-growth of rape(Brassica campestris L.), with inhibition rates of 85.0%～98.2%(A-class activity level), much better than that of the positive control flumioxazin. In addition, an effective and reasonable 3D-QSAR model was established by CoMFA method in SYBYL-X 2.1.1 software. It was found that, the steric field was the major factor towards the herbicidal activity of the target compounds against B. campestris L., and the introduction of bulky groups into m-and p-position of the benzene ring was favourable to increase the herbicidal activity. This kind of title compounds deserved further study as potential leading compounds for the discovery and development of novel herbicidal agents.

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Section: Herbicidal Activity Evaluationmentioning

confidence: 99%

“…In order to further investigate the structure-herbicidal activity relationship of target compounds bearing different R groups, 3D-QSAR analysis was carried out by CoMFA method in SYBYL-X 2.1.1 software(Tripos, Inc., St. Louis, MO, USA), according to the literatures (Li et al 2022, Li, Cen, et al 2021.…”

Section: D-qsar Analysismentioning

confidence: 99%

High value-added application of natural forest product α- pinene: design, synthesis and 3D-QSAR study of novel α- campholenic aldehyde-based 4-methyl-1,2,4-triazole-thioether compounds with significant herbicidal activity

Yin

et al. 2022

Natural Product Research

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“…In view of the above‐mentioned clues and our previous works for discovery of natural product‐based bioactive compounds, [35–40] taking SDH as the target enzyme and using the principle of active group splicing, a series of novel anisaldehyde‐derived amide‐thiourea derivatives, which kept the phenylpropanoid C6–C3 active structural skeleton of ( E )‐anethole, were designed and synthesized by integrating bioactive amide and thiourea groups into the skeleton of anisaldehyde. In vitro antifungal evaluation and structure‐activity relationship of all target compounds were also carried out.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel Anisaldehyde‐Derived Amide‐Thiourea Compounds

Duan

et al. 2022

Chemistry & Biodiversity

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Succinate dehydrogenase (SDH) is an important target enzyme for designing agricultural chemical fungicides. In order to explore novel natural product‐based antifungal agents, twenty‐one unreported anisaldehyde‐derived amide‐thiourea compounds were designed and synthesized using the principle of active splicing, and structurally confirmed by 1H‐NMR, 13C‐NMR, ESI‐MS, FT‐IR, and element analysis. In vitro antifungal activity of the target compounds was evaluated by the agar dilution method. The results showed that some target compounds exhibited better or comparable antifungal activity than that of the commercial fungicide chlorothalonil, in which compounds 5c, 5o, and 5r displayed excellent antifungal activity of 92.6 %, 92.6 % and 99.1 % against P. piricola, respectively, better than that of the positive control. In addition, 3D‐QSAR analysis was carried out by the CoMFA method to reveal the relationship between the structures of the target compounds and their inhibitory activities. The simulative binding mode of the target compounds and SDH was also studied by molecular docking.

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“…All of these clues above enlightened us to look for some photoresponsive molecules with herbicidal activity for decreasing the amount of residual active compounds in the environment. Based on the experience in longstanding research for natural product-based agrochemicals, − using the oxime ether group as a trigger switch, a series of ( E ) and ( Z )-verbenone oxime ether compounds were synthesized using α-pinene as the starting material, which is the main constituent of the abundant natural product turpentine oil. Their structures were characterized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (E)/(Z)-Verbenone Oxime Ethers and Photoresponsive Behavior to Herbicidal Activity

Cui

Wang

Lin

et al. 2022

J. Agric. Food Chem.

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The accumulation of residual active herbicides in the environment can cause a series of problems. It is thus meaningful to explore a photoresponsive herbicide, whose activity can be weakened under the action of light to reduce the negative effect. To this purpose, a series of (E)/(Z)-verbenone oxime ethers were designed, synthesized, and characterized. Oxime ether groups were adopted as the trigger switches. The preliminary screening for herbicidal activity showed that some of them exhibited better or comparable effects than that of the commercial herbicide flumioxazin against Brassica campestris and Echinochloa crusgalli. Meanwhile, five pairs of the target compounds with significantly different herbicidal effects between E- and Z-forms were further investigated for their reversible isomerization reaction and the accompanying variation of herbicidal activity. As a result, the maximum conversion rates were around 50%, and the herbicidal effect of the resulting mixture of E- and Z-isomers decreased outstandingly. The phototransformation mechanism of a pair of isomers (E)-4a and (Z)-4a was preliminarily explored. Besides, a reasonable and effective 3D-quantitative structure–activity relationship model (r 2 = 0.984 and q 2 = 0.571) was established and the binding mode was also investigated by molecular docking.

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Synthesis, Herbicidal Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-Methyl- 1,2,4-triazole-thioether Compounds Containing Natural Styrene Structure

Cited by 6 publications

References 27 publications

High value-added application of natural forest product α- pinene: design, synthesis and 3D-QSAR study of novel α- campholenic aldehyde-based 4-methyl-1,2,4-triazole-thioether compounds with significant herbicidal activity

High value-added application of natural forest product α- pinene: design, synthesis and 3D-QSAR study of novel α- campholenic aldehyde-based 4-methyl-1,2,4-triazole-thioether compounds with significant herbicidal activity

Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel Anisaldehyde‐Derived Amide‐Thiourea Compounds

Synthesis of (E)/(Z)-Verbenone Oxime Ethers and Photoresponsive Behavior to Herbicidal Activity

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