发现新的 (+) -诺卡基氨基衍生物作为潜在的杀虫剂候选物
Yong Guo1,2, Meiyue Han2, Yan Zhong1
1Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan 421001, China.
Journal of agricultural and food chemistry
|June 24, 2024
概括
新的 (+) -nootkatone氨基衍生物对关键农业害虫具有强大的杀虫活性. 这些新型绿色农药显示出显著的增长抑制和杀作用,为合成选项提供了有希望的替代品.
科学领域:
- 农业化学 农业化学
- 有机化学 有机化学
- 昆虫学 昆虫学是一门学科.
背景情况:
- 对于可持续农业而言,需要新型,有效和环保的杀虫剂至关重要.
- (+) -天然产品Nootkatone可以作为开发新农药的潜在支架.
研究的目的:
- 合成和评估基于 (+) -nootkatone的新型氨基衍生物的杀虫性能.
- 识别针对主要农业害虫的有力化合物,如Mythimna separata,Myzus persicae和Plutella xylostella.
主要方法:
- 一系列 (+) -nootkatone氨基衍生物 (化合物3a-t) 的合成.
- 杀虫剂生物测试以确定抑制生长 (GI),杀虫剂 (LD50) 和幼虫剂 (LC50) 的活性.
- 涉及氨酸S转移酶 (GST) 抑制和分子对接的初步机制研究.
- 对非标生物的毒性评估.
主要成果:
- 与母化合物相比,大多数 (+) -nootkatone衍生物表现出增强的杀虫活性.
- 化合物3a,3d,3h,3m,3n,3p和3r显示出对M的优越增长抑制. 这是一个独立的.
- 化合物3o对M.表现出强烈的杀虫活性. (LD50 = 0.011 微克/幼虫). 它们的
- 化合物3g和3n表现出显著的杀性活性,对P. xylostella (LC50分别为260和230毫克/升),性能优于罗.
- 衍生品3g和3n显示出对P的更好的现场疗效. xylostella和对非标生物的毒性较低.
- 发现衍生物3n抑制了P.P.中的GST活性. xylostella,具有分子对接,支持其与GST的相互作用.
结论:
- (+) -Nootkatone氨基衍生物代表了一类有前途的新型绿色杀虫剂.
- 化合物3g和3n特别有效地对抗P. xylostella,并表现出有利的安全概况.
- 由衍生品3n抑制GST,可以了解其杀虫机制.
相关概念视频
Physical Properties of Amines
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Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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2° Amines to N-Nitrosamines: Reaction with NaNO2
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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Amines: Introduction
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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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