Construction and agrochemical efficacy of novel indolo[2,3-b]andrographolide derivatives

To find new pesticide candidates, by using of a natural product andrographolide as the precursor, a series of novel indolo[2,3-b]andrographolide derivatives were semisynthesized by Fischer-indole rearrangement reaction. Their structures were identified by 1H NMR, IR, mp, and HRMS, and the steric con...

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Bibliographic Details
Published inAdvanced Agrochem Vol. 2; no. 4; pp. 349 - 355
Main Authors Hao, Meng, Lv, Min, Li, Tianze, Xu, Hui
Format Journal Article
LanguageEnglish
Published KeAi Communications Co., Ltd 01.12.2023
Subjects
Andrographolide
Indole
Insecticidal activities
SEM
Structural modifications
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Summary:To find new pesticide candidates, by using of a natural product andrographolide as the precursor, a series of novel indolo[2,3-b]andrographolide derivatives were semisynthesized by Fischer-indole rearrangement reaction. Their structures were identified by 1H NMR, IR, mp, and HRMS, and the steric configuration of compound Ic was further determined on single-crystal analysis. Compounds If and IIb showed 5.9 and 7.0 times potent acaricidal activity compared to andrographolide against Tetranychus cinnabarinus. Compound Ib displayed 4.2 folds higher aphicidal activity compared to andrographolide against Eriosoma lanigerum. In addition, the pronounced insecticidal activity of compound IIc against Aphis citricola was 4.2 folds of that of andrographolide. Scanning electron microscopy revealed that compound IIb can destroy the epidermis of T. cinnabarinus. These results can provide a basis for future research on botanical agrochemicals.
ISSN:2773-2371
2773-2371
DOI:10.1016/j.aac.2023.07.004