Diamides conformationally restricted with central amino acid: Design, synthesis, and biological activities

Chen, Rui‐Jia; Zhou, Cong; Dong, Lefeng; Feng, Tingting; Wang, Gangao; Wang, Junjie; Gu, Yu‐Cheng; Xu, Zhiping; Cheng, Jiagao; Shao, Xusheng; Xu, Xiaoyong; Zhong, Li

doi:10.1002/jhet.4443

Cited by 10 publications

(10 citation statements)

References 37 publications

(37 reference statements)

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“…The optimized structures of the complexes were generated by Pymol 1.7.6. 43,45 CoMFA Calculation. The CoMFA calculation was carried out using SYBYL-X 2.0 software.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study

Yang

Zhou

Wang

et al. 2023

J. Agric. Food Chem.

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In order to develop anthranilic diamides with novel chemotypes, a series of anthranilic diamides with acrylamide linkers were designed and synthesized. The results of preliminary bioassays indicated that compounds with a monofluoroalkene amide linker (Z-isomer) exhibited good larvicidal activity against lepidopteran pests. The LC50 values of compound A23 against Mythimna separata and Plutella xylostella were 1.44 and 3.48 mg·L–1, respectively, while those of chlorantraniliprole were 0.08 and 0.06 mg·L–1, respectively. Compound A23 also exhibited the same level of lethal potency against resistant and susceptible strains of Spodoptera frugiperda at 50 mg·L–1. Compound A23 exhibited similar symptoms as chlorantraniliprole in test larvae. Comparative molecular field analysis was conducted to demonstrate the structure–activity relationship. Central neuron calcium imaging experiments indicated that monofluoroalkene compounds were potential ryanodine receptor (RyR) activators and activated calcium channels in both the endoplasmic reticulum and the cell membrane. Molecular docking suggested that A23 had a better binding potency to P. xylostella RyR than chlorantraniliprole. The MM|GBSA dG bind value of A23 with P. xylostella RyR was 117.611 kcal·mol–1. Monofluoroalkene was introduced into anthranilic diamide insecticides for the first time and brought a novel chemotype for insect RyR activators. The feasibility of fluoroalkenes as insecticide fragments was explored.

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“…The optimized structures of the complexes were generated by Pymol 1.7.6. 43,45 CoMFA Calculation. The CoMFA calculation was carried out using SYBYL-X 2.0 software.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…The binding potencies of the superior complex were also evaluated by MM-GBSA free energy analysis encoded in the prime module of Maestro 10.2. The optimized structures of the complexes were generated by Pymol 1.7.6. , …”

Section: Methodsmentioning

confidence: 99%

Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study

Yang

Zhou

Wang

et al. 2023

J. Agric. Food Chem.

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“…When the reaction was complete, as monitored by TLC, the reaction mixture was concentrated in vacuum, the concentrate was adjusted to pH 7 with sodium bicarbonate, and then extracted with ethyl acetate. The combined organic phase was filtered after drying over anhydrous sodium sulfate and concentrated in vacuum to give intermediate 6 with yields of 95.3% to 96.4% [ 40 ].…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Fungicidal and Insecticidal Activities of Novel Diamide Compounds Combining Pyrazolyl and Polyfluoro-Substituted Phenyl into Alanine or 2-Aminobutyric Acid Skeletons

Feng²,

Liu³

et al. 2023

Molecules

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Thirty novel diamide compounds combining pyrazolyl and polyfluoro-substituted phenyl groups into alanine or 2-aminobutyric acid skeletons were designed and synthesized with pyflubumide as the lead compound to develop potent and environmentally friendly pesticides. The preliminary bioassay results indicated that the new compounds containing the para-hexa/heptafluoroisopropylphenyl moiety exhibit fungicidal, insecticidal, and acaricidal activities. This is the first time that the para-hexa/heptafluoroisopropylphenyl group is a key fragment of the fungicidal activity of new N-phenyl amide compounds. Most of the target compounds exhibited moderate to good insecticidal activity against Aphis craccivora at a concentration of 400 μg/mL, and some showed moderate activity at a concentration of 200 μg/mL; in particular, compounds I-4, II-a-10, and III-26 displayed higher than 78% lethal rates at 200 μg/mL. Compound II-a-14 exhibited a 61.1% inhibition at 200 μg/mL for Tetranychus cinnabarinus. In addition, some of the target compounds exhibited good insecticidal activities against Plutella xylostella at a concentration of 200 μg/mL; the mortalities of compounds I-1, and II-a-15 were 76.7% and 70.0%, respectively. Preliminary analysis of the structure–activity relationship (SAR) indicated that the insecticidal and acaricidal activities varied significantly depending on the type of substituent and substitution pattern. The fungicidal activity results showed that compounds I-1, II-a-10, II-a-17, and III-26 exhibited good antifungal effects. Enzymatic activity experiments and in vivo efficacy of compound II-a-10 were conducted and discussed.

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“…38 Compound 33 showed potential for further optimization as an insecticidal lead with the LC 50 value of 86.8 mg/L, and compound 34 was identified as a potential insecticidal candidate with LC 50 values of 34.920 mg/L against M. separata and 61.992 mg/against P. xylostella. 39 These results demonstrated that adding some electronwithdrawing groups (polyfluoro, cyano, and chlorine) to the benzene ring improves the insecticidal activities of the compounds; however, adding large volumes of the substituted groups might be unsuitable. Despite these findings, no suitable aromatic heterocyclic system has been found to replace the benzene ring.…”

Section: Part Amentioning

confidence: 99%

“…Moreover, Li Zhong’s group designed and synthesized diamide derivatives containing α-amino acids and found that most of the compounds containing an L -phenylglycine skeleton had good insecticidal activities at 500 mg/L . Compound 33 showed potential for further optimization as an insecticidal lead with the LC 50 value of 86.8 mg/L, and compound 34 was identified as a potential insecticidal candidate with LC 50 values of 34.920 mg/L against M. separata and 61.992 mg/against P. xylostella …”

Section: Diamide Derivatives Acting As Ryrs Activatorsmentioning

confidence: 99%

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

2023

J. Agric. Food Chem.

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The world’s hunger is continuously rising due to conflicts, climate change, pandemics (such as the recent COVID-19), and crop pests and diseases. It is widely accepted that zero hunger is impossible without using agrochemicals to control crop pests and diseases. Diamide insecticides are one of the widely used green insecticides developed in recent years and play important roles in controlling lepidopteran pests. Currently, eight diamine insecticides have been commercialized, which target the insect ryanodine receptors. This review summarizes the development and optimization processes of diamide derivatives acting as ryanodine receptor activators. The review also discusses pest resistance to diamide derivatives and possible solutions to overcome the limitations posed by the resistance. Thus, with reference to structural biology, this study provides an impetus for designing and developing diamide insecticides with improved insecticidal activities.

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Diamides conformationally restricted with central amino acid: Design, synthesis, and biological activities

Cited by 10 publications

References 37 publications

Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study

Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study

Design, Synthesis, Fungicidal and Insecticidal Activities of Novel Diamide Compounds Combining Pyrazolyl and Polyfluoro-Substituted Phenyl into Alanine or 2-Aminobutyric Acid Skeletons

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

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