Discovery of novel iminosydnone compounds with insecticidal activities based on the binding mode of triflumezopyrim

Du, Shaoqing; Hu, Xueping; Li, Mengnan; Jiang, Xian; Xu, Xiaoyong; Cheng, Jiagao; Qian, Xuhong

doi:10.1016/j.bmcl.2021.128120

Cited by 8 publications

(8 citation statements)

References 29 publications

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“…[1][2][3][4][5][6][7] Recently, there has been interest in the use of these compounds in agriculture. Several sydnones and sydnone imines have insecticidal, [8,9] herbicidal, [10] and growth-stimulating properties. [11,12] Derivatives of 3-benzyl-4-phenylsidnones have demonstrated fungicidal activity.…”

Section: Introductionmentioning

confidence: 99%

Ferrocenyl alkylation of 4‐mercapto derivatives of sydnones and sydnone imines. New antidotes for sulfonylurea herbicides

Shevaldina

Tsyganov

Kalganova

et al. 2022

Applied Organom Chemis

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Section: Introductionmentioning

confidence: 99%

Ferrocenyl alkylation of 4‐mercapto derivatives of sydnones and sydnone imines. New antidotes for sulfonylurea herbicides

Shevaldina

Tsyganov

Kalganova

et al. 2022

Applied Organom Chemis

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“…It can be used to study the mode of action of insecticides that acts on nAChR. 29 The crystal structure (3C79) of nAChBP with imidacloprid (IMI) was selected for molecular docking research. The docking results are shown in Figures 8 and 9…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…nAChBP, the homologous protein of a nicotinic acetylcholine receptor (nAChR), had the same acetylcholine binding site and similar functions with nAChR. It can be used to study the mode of action of insecticides that acts on nAChR . The crystal structure (3C79) of nAChBP with imidacloprid ( IMI ) was selected for molecular docking research.…”

Section: Resultsmentioning

confidence: 99%

New Synthetic Method and Insecticidal Activities of Novel Imidazopyridine Mesoionic Derivatives Containing an Ester Group

Liu

Song

Zhang

et al. 2022

J. Agric. Food Chem.

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To develop novel insecticides with high efficiency, a new mode of action, and safety to nontarget organisms and the environment, a series of imidazopyridine mesoionic compounds containing an ester group have been designed and synthesized via a new synthetic method discovered by our group. The bioactivity results showed that most of the target compounds exhibited significant insecticidal activities against Aphis craccivora, and some of them showed moderate insecticidal activities against Sogatella furcifera. Among them, compounds C2, C4−C11, and D3 showed excellent insecticidal activities against A. craccivora (LC 50 values were lower than 4.5 μg/mL), which were superior to those of pymetrozine (LC 50 = 6.19 μg/mL) and triflumezopyrim (LC 50 = 4.68 μg/mL). Remarkably, the insecticidal activity of compound C9 was 5.9-fold greater than that of triflumezopyrim with an LC 50 value of 0.8 μg/mL. Proteomics and molecular docking results indicated that compound C9 may affect the nervous system of A. craccivora and act on nicotinic acetylcholine receptors like triflumezopyrim.

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“…The nAChBPs and nAChRs are homologous proteins with similar acetylcholine combination sites and analogous functions, which makes them ideal alternative structures . The crystal structures of Lymnaea stagnalis acetylcholine binding protein (Ls-AChBP) complexed with Imidacloprid (PDB ID: 2ZJU) − obtained from the Protein Data Bank (PDB, ) were used as templates in molecular docking.…”

Section: Methodsmentioning

confidence: 99%

Discovery of Pyrido[1,2-a]pyrimidine Mesoionic Compounds Containing Benzo[b]thiophene Moiety as Potential Pesticide Candidates

Zhang

Liu

et al. 2022

J. Agric. Food Chem.

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The increasing evolution of insect resistance has made it challenging for traditional insecticides to control the bean aphid (Aphis craccivora Koch). To address this pending issue, a range of pyrido[1,2-a]pyrimidine mesoionic compounds containing benzo[b]thiophene were designed and synthesized. The biological activity test results of the target compounds indicated that they had moderate to outstanding insecticidal activity against the bean aphid (Aphis craccivora) and moderate insecticidal activity against the white-backed planthopper (Sogatella f urcifera). Compound L14 exhibited significant insecticidal activity against A. craccivora, with an LC 50 value of 1.82 μg/mL, which was superior to triflumezopyrim (LC 50 = 4.76 μg/mL). The results of enzyme activity assay showed that compound L14 had a definite inhibitory effect on ATPase. Moreover, the proteomics and docking findings of compound L14 suggested that it may act on the central nervous system of aphids and interact with nicotinic acetylcholine receptors. Therefore, compound L14 is a potentially novel insecticide candidate for further utilization.

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Discovery of novel iminosydnone compounds with insecticidal activities based on the binding mode of triflumezopyrim

Cited by 8 publications

References 29 publications

Ferrocenyl alkylation of 4‐mercapto derivatives of sydnones and sydnone imines. New antidotes for sulfonylurea herbicides

Ferrocenyl alkylation of 4‐mercapto derivatives of sydnones and sydnone imines. New antidotes for sulfonylurea herbicides

New Synthetic Method and Insecticidal Activities of Novel Imidazopyridine Mesoionic Derivatives Containing an Ester Group

Discovery of Pyrido[1,2-a]pyrimidine Mesoionic Compounds Containing Benzo[b]thiophene Moiety as Potential Pesticide Candidates

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