Synthesis of Novel (9<i>S</i>)‐Acyloxy Derivatives of Quinidine and Dihydroquinidine as Insecticidal Agents

Che, Zhiping; Yang, Jinming; Sun, Di; Tian, Yuee; Liu, Shengming; X, Lin; Jiang, Jia; Chen, Genqiang

doi:10.1002/cbdv.201900696

Cited by 7 publications

(6 citation statements)

References 37 publications

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“…We take toosendanin as the positive control 58 . The symptoms of M. separata at the three stages (larval, pupal, and adult) of target compound treatment were consistent with those previously reported 45,50,55–57 . The body surface of some larvae shrank and could not molt normally and died (Fig.…”

Section: Resultssupporting

confidence: 85%

“…The stomach action of target compounds against the pre‐third‐instar larvae of M. separata was determined by using the leaf‐dipping method at a concentration of 1 mg mL −1 55–57 . We take toosendanin as the positive control 58 .…”

Section: Resultsmentioning

confidence: 99%

“…The stomach action of target compounds against the pre-thirdinstar larvae of M. separata was determined by using the leafdipping method at a concentration of 1 mg mL −1 . [55][56][57] We take toosendanin as the positive control. 58 The symptoms of M. separata at the three stages (larval, pupal, and adult) of target compound treatment were consistent with those previously reported.…”

Section: Insecticidal Activitymentioning

confidence: 99%

“…58 The symptoms of M. separata at the three stages (larval, pupal, and adult) of target compound treatment were consistent with those previously reported. 45,50,[55][56][57] The body surface of some larvae shrank and could not molt normally and died (Fig. 4); some larvae formed abnormal pupae (half pupae and half larvae) and died (Fig.…”

Section: Insecticidal Activitymentioning

confidence: 99%

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Synthesis of paeonol ester derivatives and their insecticidal, nematicidal, and anti‐oomycete activities

Che

Guo

et al. 2022

Pest Management Science

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Background: Paeonol is extracted and isolated as a rich and sustainable natural bioresource from the root bark of Paeonia suffruticosa, the derivatives of which exhibit numerous biological activities. It is well known that ester compounds play a very important role in pest control, such as organophosphorus, carbamate and pyrethroid pesticides.Results: To discover biorational natural product-based pesticides, three series of (60) paeonol ester derivatives (7a-t, 8g,p, 9g,p, 10g-j,n-u, 11g,u, 12g,u, 13a-p, 14b,c, and 15b,c) were prepared by structural modification of paeonol, and their structures were well characterized by proton nuclear magnetic resonance ( 1 H-NMR), carbon-13 nuclear magnetic resonance ( 13 C-NMR), high-resolution mass spectrometry (HRMS), and melting point. Furthermore, we assessed the compounds as insecticidal, nematicidal, and antioomycete agents against three serious agricultural pests, Mythimna separata, Heterodera glycines, and Phytophthora capsici. Among all tested compounds: (i) compound 8p showed more significant insecticidal activity than toosendanin, and the final mortality rates of 8p and toosendanin against M. separata (1 mg mL −1 ) were 70.4%, and 51.9%, respectively; (ii) compound 7a exhibited more promising nematicidal activity than paeonol, and the median lethal concentration (LC 50 ) values of 7a and 1 against H. glycines were 15.47 and 50.80 mg L −1 , respectively; (iii) compounds 7n and 13m displayed more significant anti-oomycete activity compared to zoxamide against Phytophthora capsici, and the median effective concentration (EC 50 ) values of 7n, 13m, and zoxamide were 23.72, 24.51, and 26.87 mg L −1 , respectively; and the protective effect of the compounds against Phytophthora capsici in vivo further confirmed the effectiveness of the agents.Conclusion: This study suggested that the introduction of a nitro at the C5 or C3 position of paeonol could improve its bioactivity against M. separata, H. glycines, and Phytophthora capsici.

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Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Insecticidal Activitymentioning

confidence: 99%

Section: Insecticidal Activitymentioning

confidence: 99%

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Synthesis of paeonol ester derivatives and their insecticidal, nematicidal, and anti‐oomycete activities

Che

Guo

et al. 2022

Pest Management Science

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“…The Cl atom on the quinoline ring is essential for the insecticidal activity of the compounds. Although compound 53 has one more double bond structure than compound 54 , they have the same scaffold structure with comparable insecticidal activity against stick insects . In addition, compound 55 showed LC 50 values of 75.7 and 129.7 mg/L against Tribolium castaneum and Sitophilus zeamais …”

Section: Insecticidal and Acaricidal Activitymentioning

confidence: 99%

Quinoline Derivatives in Discovery and Development of Pesticides

Cai,

Song,

Zhang

et al. 2024

J. Agric. Food Chem.

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Finding highly active molecular scaffold structures is always the key research content of new pesticide discovery. In the research and development of new pesticides, the discovery of new agricultural molecular scaffold structures and new targets still faces great challenges. In recent years, quinoline derivatives have developed rapidly in the discovery of new agriculturally active molecules, especially in the discovery of fungicides. The unique quinoline scaffold has many advantages in the discovery of new pesticides and can provide innovative and feasible solutions for the discovery of new pesticides. Therefore, we reviewed the use of quinoline derivatives and their analogues as molecular scaffolds in the discovery of new pesticides since 2000. We systematically summarized the agricultural biological activity of quinoline compounds and discussed the structure–activity relationship (SAR), physiological and biochemical properties, and mechanism of action of the active compounds, hoping to provide ideas and inspiration for the discovery of new pesticides.

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Synthesis, Anti‐Oomycete and Anti‐fungal Activities of Novel Cinchona Alkaloid Derivatives Containing Sulfonate Moiety

Che

Chen

Zhang

et al. 2023

Chemistry & Biodiversity

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Using cinchona alkaloid as the lead compound, twenty-four cinchona alkaloid sulfonate derivatives (1 a-l, 2 a-c, 3 a-c, 4 ac, and 5 a-c) were designed and prepared by modifying their C9 position, and structurally confirmed by 1 H-NMR, 13 C-NMR, HR-MS and melting points. Moreover, the stereochemical configurations of compounds 1 f and 1 l were unambiguously confirmed by single-crystal X-ray diffraction. Furthermore, we determined the anti-oomycete and anti-fungal activities of these target compounds against Phytophthora capsici and Fusarium graminearum in vitro. The results showed that two compounds 4 b and 4 c exhibited prominent anti-oomycete activity, and the median effective concentration (EC 50 ) values of 4 b and 4 c against P. capsici were 22.55 and 16.32 mg/L, respectively. This study suggested that when the C9 position of cinchona alkaloid sulfonate derivatives is in the S configuration and the 6'-position methoxy group is not present, the anti-oomycete activity is superior. In addition, five compounds 1 e, 1 f, 1 k, 3 c and 4 c displayed significant anti-fungal activity, with EC 50 values of 43.64, 45.07, 80.18, 48.58 and 41.88 mg/L against F. graminearum, respectively. This result indicates that only when a specific substituent is introduced into the structural framework of the target compound, the corresponding compound exhibits significant inhibitory activity against fungi.

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Synthesis of Novel (9S)‐Acyloxy Derivatives of Quinidine and Dihydroquinidine as Insecticidal Agents

Cited by 7 publications

References 37 publications

Synthesis of paeonol ester derivatives and their insecticidal, nematicidal, and anti‐oomycete activities

Synthesis of paeonol ester derivatives and their insecticidal, nematicidal, and anti‐oomycete activities

Quinoline Derivatives in Discovery and Development of Pesticides

Synthesis, Anti‐Oomycete and Anti‐fungal Activities of Novel Cinchona Alkaloid Derivatives Containing Sulfonate Moiety

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