设计,合成和生物活性的三甲基替代甲醇衍生物的设计,合成和生物活性
Lefeng Dong1, Weiguo Wang1, Liqi Zhou2
1Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
Journal of agricultural and food chemistry
|May 17, 2024
概括
新的甲酸杀虫剂被合成,以减少毒性. 化合物8d对斑马鱼的毒性比fipronil低14倍,为害虫控制提供了更安全的替代品.
科学领域:
- 农业化学科学 农业化学科学
- 有机化学 有机化学
- 毒理学 毒理学 毒理学
背景情况:
- 菲普罗尼尔是一种广泛的甲酸杀虫剂,由于其对水生生物和蜜蜂的高毒性,造成了严重的环境风险.
- 需要开发具有相似效率但环境影响较小的新型杀虫剂.
研究的目的:
- 设计和合成具有降低毒性的新型甲酸衍生物.
- 评估合成化合物的杀虫活性和毒性概况.
主要方法:
- 合成了35种含有三乙基在皮拉环的4位位置的甲基衍生物.
- 生物测试,以确定杀虫剂活性对艾迪斯 albopictus,普鲁特拉 xylostella,和阿菲斯 craccivora.
- 使用胚胎-幼年斑马鱼发育的毒性评估.
主要成果:
- 化合物7在0.125毫克/升的剂量下显示了69.7%的杀伤性对白斑虫.
- 化合物7,7g,8d和10j对Plutella xylostella表现出优越的杀虫活性.
- 化合物7显示出与菲普罗尼尔相比的杀虫活性,可以对抗Aphis craccivora.
- 与菲普罗尼尔 (LC50 = 1.05 mg/L) 相比,化合物8d对斑马鱼的毒性明显较低 (LC50 = 14.28 mg/L).
结论:
- 合成的甲衍生物显示出作为杀虫剂的潜力,具有更好的安全性.
- 化合物8d是开发更安全的防虫剂的有希望的候选物,因为它对水生生物的毒性降低了.
- 对结构-活性关系和结合机制的进一步研究可以优化未来的杀虫剂开发.
相关概念视频
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
5.9K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.9K
Directing and Steric Effects in Disubstituted Benzene Derivatives
3.1K
When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
3.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
3.0K
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
3.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Preparation and Reactions of Sulfides
4.8K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.8K


