Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel

Chen, You‐Wei; Li, Yuxin; Li, Pan; Liu, Jingbo; Wan, Yingying; Chen, Wei; Xiong, Lixia; Yang, Na; Song, Haibin; Li, Zhengming

doi:10.1016/j.bmc.2014.09.052

Cited by 9 publications

(7 citation statements)

References 23 publications

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“…Calcium imaging experiments were performed to determine the insecticidal mechanism of the target compound CN06 by using our previously reported method. , The third instars of M. separata larval were obtained from the Bioassay Department, Nankai University, and experiments were carried out under laboratory conditions (temperature 27 ± 1 °C, relative humidity 75 ± 5%, 16:8 h of light:darkness) after two generations of rearing on agar-based semisynthetic food. After anesthetizing the third instar larvae of M. separata under aseptic conditions, the thoracic and abdominal ganglia were taken at 28 °C and placed first in saline and then transferred to a solution containing 0.3% trypsin.…”

Section: Methodsmentioning

confidence: 99%

Improving Insecticidal Activity of Chlorantraniliprole by Replacing the Chloropyridinyl Moiety with a Substituted Cyanophenyl Group

Zhang

Ren

et al. 2022

J. Agric. Food Chem.

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Insect ryanodine receptors (RyRs) are molecular targets of the anthranilic diamide insecticides. In the present study, a new series of anthranilic diamides containing a cyanophenyl pyrazole moiety were rationally designed by active-fragment assembly and computer-aided design using the 3D structure of Plutella xylostella RyRs as a receptor and chlorantraniliprole as a ligand. Most of the titled compounds showed good toxicity against Mythimna separate, P. xylostella, and Spodoptera frugiperda. Compounds CN06, CN11, and CN16 with corresponding LC50 values of 0.15, 0.29, and 0.52 mg·L–1, respectively, against M. separate showed comparable activity to that of chlorantraniliprole (0.13 mg·L–1). Surprisingly, CN06, CN11, and CN16 with corresponding LC50 values of 1.6 × 10–5, 3.0 × 10–5, and 2.8 × 10–5 mg·L–1, respectively, against P. xylostella were at least 5-fold more active than chlorantraniliprole (1.5 × 10–4 mg·L–1). In the case of S. frugiperda, CN06, CN11, and CN16 had good potency but lower than chlorantraniliprole in terms of LC50 values (0.58, 0.54, and 0.56 mg·L–1 versus 0.31 mg·L–1). Molecular docking of CN06 and chlorantraniliprole to P. xylostella RyRs validated the molecular design, and the calcium imaging technique further proved the potential target of CN06 as RyRs. Compounds CN06, CN11, and CN16 could be more effective than chlorantraniliprole in targeting the resistant RyR mutants of S. frugiperda (G4891E, I4734M) through the binding mode and energy obtained by molecular docking. Density functional theory calculations (DFT) and electrostatic potential (ESP) studies gave the structure–activity relationship. Compounds CN06, CN11, and CN16 could be used as potent insecticide leads for further optimization.

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Section: Methodsmentioning

confidence: 99%

Improving Insecticidal Activity of Chlorantraniliprole by Replacing the Chloropyridinyl Moiety with a Substituted Cyanophenyl Group

Zhang

Ren

et al. 2022

J. Agric. Food Chem.

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“…The insecticideal mechanism of these novel compounds was investigated according to calcium imaging experiment reported by our previous work. 13,32 ■ RESULTS AND DISCUSSION Chemistry. Compound 1e was prepared by referring to the literature with some modification as shown in Figure 2.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…The insecticideal mechanism of these novel compounds was investigated according to calcium imaging experiment reported by our previous work. , …”

Section: Methodsmentioning

confidence: 99%

Novel Anthranilic Diamide Scaffolds Containing N-Substituted Phenylpyrazole as Potential Ryanodine Receptor Activators

Liu

Zhang

et al. 2016

J. Agric. Food Chem.

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To discover potent insecticides targeting ryanodine receptors (RyRs), a series of novel anthranilic diamides analogues (12a-12u) containing N-substituted phenylpyrazole were designed and synthesized. These compounds were characterized by (1)H NMR, (13)C NMR, and HRMS, and the structure of compound 12u was confirmed by X-ray diffraction. Their insecticidal activities indicated that these compounds displayed moderate to excellent activities. In particular, 12i showed 100 and 37% larvicidal activities against oriental armyworm (Mythimna separata) at 0.25 and 0.05 mg L(-1), equivalent to that of chlorantraniliprole (100%, 0.25 mg L(-1); and 33%, 0.05 mg L(-1)). The activity of 12i against diamondback moth (Plutella xylostella) was 95% at 0.05 mg L(-1), whereas the control was 100% at 0.05 mg L(-1). The calcium-imaging technique experiment results showed that the effects of 12i on the intracellular calcium ion concentration ([Ca(2+)]i) in neurons were concentration-dependent. After the central neurons of Helicoverpa armigera were dyed by loading with fluo-5N and treated with 12i, the free calcium released in endoplasmic reticulum indicated the target of compound 12i is RyRs or IP3Rs. The activation of RyRs by natural ryanodine completely blocked the calcium release induced by 12i, which indicated that RyRs in the central neurons of H. armigera third-instar larvae is the possible target of compound 12i.

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“…Besides, the iodobenzyl analogues 10 and 11 had no insecticidal activity. Multiple studies have demonstrated that the introduction of a fluorine atom was useful for increasing insecticidal activity because of its unique properties such as electronegativity, size, and electrostatic interactions [21][22][23][24][25]. Herein, 12-21 were modified by fluorinated benzyl and most exhibited stronger activity (16 and 19 were inactive).…”

Section: Insecticidal Activity Against Helicoverpa Armigera Hübnermentioning

confidence: 99%

Design, Semisynthesis, Insecticidal and Antibacterial Activities of a Series of Marine-Derived Geodin Derivatives and Their Preliminary Structure–Activity Relationships

et al. 2022

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To enhance the biological activity of the natural product geodin (1), isolated from the marine-derived fungus Aspergillus sp., a series of new ether derivatives (2–37) was designed and semisynthesized using a high-yielding one-step reaction. In addition, the insecticidal and antibacterial activities of all geodin congeners were evaluated systematically. Most of these derivatives showed better insecticidal activities against Helicoverpa armigera Hübner than 1. In particular, 15 showed potent insecticidal activity with an IC50 value of 89 μM, comparable to the positive control azadirachtin (IC50 = 70 μM). Additionally, 5, 12, 13, 16, 30 and 33 showed strong antibacterial activity against Staphylococcus aureus and Aeromonas salmonicida with MIC values in the range of 1.15–4.93 μM. The preliminary structure–activity relationships indicated that the introduction of halogenated benzyl especially fluorobenzyl, into 1 and substitution of 4-OH could be key factors in increasing the insecticidal and antibacterial activities of geodin.

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Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel

Cited by 9 publications

References 23 publications

Improving Insecticidal Activity of Chlorantraniliprole by Replacing the Chloropyridinyl Moiety with a Substituted Cyanophenyl Group

Improving Insecticidal Activity of Chlorantraniliprole by Replacing the Chloropyridinyl Moiety with a Substituted Cyanophenyl Group

Novel Anthranilic Diamide Scaffolds Containing N-Substituted Phenylpyrazole as Potential Ryanodine Receptor Activators

Design, Semisynthesis, Insecticidal and Antibacterial Activities of a Series of Marine-Derived Geodin Derivatives and Their Preliminary Structure–Activity Relationships

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