Diamides conformationally restricted with central amino acid : Design, synthesis, and biological activities
Abstract Diamide insecticides, represented by chlorantraniliprole (CHL), were widely applied in the control of lepidopteran insects. In efforts to develop bioactive diamides with novel scaffolds, we design and synthesized a series of diamides containing central amino acids to conformationally simulate CHL. Bioassay results indicated that most compounds containing 1‐aminocyclopropane‐1‐carboxylic acid exhibited excellent larvacidal potency against Mythimna separate and Plutella xylostella. After a systematic structure–activity relationship study,1–23 was identified as a potential insecticidal candidate with LC50 values of 34.920 mg·L−1 against M. separate and 61.992 mg·L−1 on P. xylostella. Finally, molecular docking revealed the possible binding mode of1–23 with the target protein, ryanodine receptors..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2022 |
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| Erschienen: |
2022 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:59 |
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| Enthalten in: |
Journal of Heterocyclic Chemistry - 59(2022), 6, Seite 1045-1053 |
| Beteiligte Personen: |
Chen, Rui‐Jia [VerfasserIn] |
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| Anmerkungen: |
© 2022 Wiley Periodicals LLC. |
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| Umfang: |
9 |
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| doi: |
10.1002/jhet.4443 |
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| funding: |
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| 520 | |a Abstract Diamide insecticides, represented by chlorantraniliprole (CHL), were widely applied in the control of lepidopteran insects. In efforts to develop bioactive diamides with novel scaffolds, we design and synthesized a series of diamides containing central amino acids to conformationally simulate CHL. Bioassay results indicated that most compounds containing 1‐aminocyclopropane‐1‐carboxylic acid exhibited excellent larvacidal potency against Mythimna separate and Plutella xylostella. After a systematic structure–activity relationship study,1–23 was identified as a potential insecticidal candidate with LC50 values of 34.920 mg·L−1 against M. separate and 61.992 mg·L−1 on P. xylostella. Finally, molecular docking revealed the possible binding mode of1–23 with the target protein, ryanodine receptors. | ||
| 700 | 1 | |a Zhou, Cong |4 aut | |
| 700 | 1 | |a Dong, Le‐Feng |4 aut | |
| 700 | 1 | |a Feng, Ting‐Ting |4 aut | |
| 700 | 1 | |a Wang, Gang‐Ao |4 aut | |
| 700 | 1 | |a Wang, Jun‐Jie |4 aut | |
| 700 | 1 | |a Gu, Yu‐Cheng |4 aut | |
| 700 | 1 | |a Xu, Zhi‐Ping |4 aut | |
| 700 | 1 | |a Cheng, Jia‐Gao |4 aut | |
| 700 | 1 | |a Shao, Xu‐Sheng |4 aut | |
| 700 | 1 | |a Xu, Xiao‐Yong |4 aut | |
| 700 | 1 | |a Li, Zhong |4 aut | |
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