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Molecules 2018, 23(1), 41; https://doi.org/10.3390/molecules23010041

Design, Synthesis and Structure-Activity Relationship of Novel Aphicidal Mezzettiaside-Type Oligorhamnosides and Their Analogues

1
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China
2
Key Laboratory of Crop Integrated Pest Management in South China, Ministry of Agriculture, Guangzhou 510642, China
3
Lab of Insect Toxicology, South China Agricultural University, Guangzhou 510642, China
4
Department of Human anatomy, School of Medicine, Jinan University, Guangzhou 510632, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 21 November 2017 / Revised: 16 December 2017 / Accepted: 22 December 2017 / Published: 26 December 2017
(This article belongs to the Section Natural Products Chemistry)
Full-Text   |   PDF [1907 KB, uploaded 26 December 2017]   |  

Abstract

Oligosaccharides have been used for an environmentally friendly insect control in the agricultural industry. In order to discover novel eco-friendly pesticides, a series of partially acetylated oligorhamnoses mezzettiasides, 28, and their analogues, 914, with biosurfactant characteristics were designed and synthesized, some of which exhibited comparable to or even stronger aphicidal activity than pymetrozine. Preliminary SAR studies demonstrated that the aphicidal activity of mezzettiasides analogs is highly dependent on their structures, including both the sugar length and the substitutes on the sugar. Among them, trirhamnolipid 9 displayed the strongest aphicidal activity, with an LC50 of 0.019 mmol/L, indicating that the biosurfactant 9 may have potential for use as an environmentally friendly agricultural pesticide. View Full-Text
Keywords: mezzettiaside; rhamnolipid; synthesis; aphicidal activity; structure–activity relationships mezzettiaside; rhamnolipid; synthesis; aphicidal activity; structure–activity relationships
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Zhao, H.; Wei, Z.; Jiang, Z.; Li, S.; Liao, Y.; Guo, Y.; Tang, Y.; Chen, W.; Zhong, G.; Song, G. Design, Synthesis and Structure-Activity Relationship of Novel Aphicidal Mezzettiaside-Type Oligorhamnosides and Their Analogues. Molecules 2018, 23, 41.

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