Synthesis and insecticidal activity of sulfonate derivatives of sesamol against <i>Mythimna separata in vivo</i>

Che, Zhiping; Yang, Jinming; Shan, Xijie; Tian, Yuee; Liu, Shengming; X, Lin; Jiang, Jia; Mei, Hu; Chen, Genqiang

doi:10.1080/10286020.2019.1616289

Cited by 14 publications

(9 citation statements)

References 23 publications

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“…For example, the CMRs of 4k against M. separata after 10, 20 and 30 days were 6.7 %, 34.5 % and 75.0 %, respectively, i. e., the CMRs of 30 days were more than 11 times of that of 10 days. Additionally, the symptoms of death of the tested M. separata during the whole process of growth were similar to our previous reports: owing to feeding too many compounds coated leaves during the first 2 days, some larvae of the tested M. separata exhibited developmental abnormalities during three stages (larval, pupation, and adult emergence) ( Figures –). Specifically, the larval stage was mainly manifested as wrinkled bodies caused by ecdysial stasis, and slim bodies attributed to antifeedant ( Figure ); even though the tested insects were normal in larval stage, deformed pupae or half‐larva and half‐pupae appeared in the pupation process ( Figure ); certainly, some of the tested insects can reach the adult stage, but there were malformed moths, such as imperfect wing or half‐pupae and half moth ( Figure ).…”

Section: Resultssupporting

confidence: 88%

“…As depicted in Scheme , dihydroquinidine ( 2 ) was obtained in 92 % yield by catalytic hydrogenolysis of 1 in the presence of 10 % Pd/C under 3 atm of hydrogen . Novel (9 S )‐acyloxy derivatives ( 3a – 3u , and 4b , 4c , 4f , 4h , 4k , 4l , 4q – 4s ) of quinidine and dihydroquinidine were smoothly obtained by reactions of 1 or 2 with the corresponding carboxylic acids ( 5 ) in the presence of DCC and DMAP . Their structures were well characterized by 1 H‐NMR, HR‐MS, and melting points.…”

Section: Resultsmentioning

confidence: 99%

“…When the reaction was complete, checked by TLC, the mixture was filtered to remove urea from the reaction, and the filtrate was diluted by dichloromethane (45 mL). Subsequently, the diluted organic phase was washed by saturated aqueous NaHCO 3 (30 mL), and brine (30 mL), dried over anhydrous Na 2 SO 4 , concentrated in vacuo, and purified by CC to give the pure (9 S )‐acyloxy derivatives 3a – 3u , and 4b , 4c , 4f , 4h , 4k , 4l , 4q – 4s of quinidine and dihydroquinidine . The data of target compounds are shown in the Supporting Information .…”

Section: Methodsmentioning

confidence: 99%

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

Che

Yang

Sun

et al. 2020

Chemistry & Biodiversity

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Endeavor to discover biorational natural products-based insecticides, two series (30) of novel (9S)-acyloxy derivatives of quinidine and dihydroquinidine were prepared and assessed for their insecticidal activity against Mythimna separata in vivo by the leaf-dipping method at 1 mg/mL. Among all the compounds, especially four derivatives exhibited the best insecticidal activity with final mortality rates of 71.4 %, 75.0 %, 71.4 %, and 75.0 %, respectively. Relatively speaking, 9-hydroxy group is well tolerated, and the results showed that after modification of the hydroxy group with an acyloxy group, the insecticidal activity was significantly increased; the configuration at C8/9 position is important for insecticidal activity, and the (9S)-configuration is optimal; modification of the out-ring double bond is acceptable, and hydrogenation of the double bond enhances insecticidal activity. These preliminary results will pave the way for further modification of quinidine in the development of potential new insecticides.

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Section: Resultssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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

Che

Yang

Sun

et al. 2020

Chemistry & Biodiversity

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“…Essential oils (Eos) do not have any obvious physiological significance for the growth of the plant itself but function mainly as defense mechanisms against a variety of pathogenic infections, including oomycetes, fungi, bacteria, and virus [10] . Eos play a very important role in the discovery of new fungicides [11–13] . Thus, it is in line with the development trend of pesticide science to develop botanical fungicides with plant secondary metabolites with antifungal activity as leading compounds [14] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Oomycete Activity of 1‐Sulfonyloxy/Acyloxydihydroeugenol Derivatives

Chen

Zhu

et al. 2021

Chemistry & Biodiversity

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Endeavor to discover biorational natural products‐based fungicides, two series (26) of novel 1‐sulfonyloxy/acyloxydihydroeugenol derivatives (3a–p and 5a–j) were prepared and assessed for their fungicidal activity against P. capsici Leonian, in vitro. Results of fungicidal activity revealed that, among all compounds, especially compounds 3a, 5c, and 5e displayed the most potent anti‐oomycete activity against P. capsici with EC50 values of 69.33, 68.81, and 67.77 mg/L, respectively. Overall, the anti‐oomycete activities of 1‐acyloxydihydroeugenol derivatives (5a–j) were higher than that of 1‐sulfonyloxydihydroeugenol derivatives (3a–p). It is proved that the introduction of the acyl group at hydroxy position of dihydroeugenol is more beneficial to improve its anti‐oomycete activity than that of the sulfonyl group. These preliminary results will pave the way for further modification of dihydroeugenol in the development of potential new fungicides.

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“…Previous studies have shown that paeonol has a wide range of pharmacological effects and biological activities, such as anti-inflammatory activity, anti-diabetic activity, anticancer activity, antioxidant and immune regulatory activity. [34][35][36][37][38] Meanwhile, paeonol has the following biological activities in agriculture: inhibition of plant pathogenic fungi, bacteria, viruses and oomycetes [39][40][41][42] ; preservation effect on fruits and vegetables 43,44 ; fumigation and contact action on pests and repellent effects on their eggs [45][46][47][48][49] ; and good plant parasitic nematode activity. 50,51 Furthermore, studies have shown that paeonol can act on acetylcholinesterase (AChE) and significantly affect the normal transmission of nerve impulses at synapses.…”

Section: Introductionmentioning

confidence: 99%

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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Synthesis and insecticidal activity of sulfonate derivatives of sesamol against Mythimna separata in vivo

Cited by 14 publications

References 23 publications

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

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

Synthesis and Anti‐Oomycete Activity of 1‐Sulfonyloxy/Acyloxydihydroeugenol Derivatives

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

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