Quantitative structure–activity relationship of 2,6-dimethoxy-N-(3-(4-substituted phenyl)isoxazol-5-yl)benzamide for the inhibition of chitin synthesis

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Journal of Pesticide Science Pub Date : 2024-05-17 DOI:10.1584/jpestics.d24-004
Kotaro Mori, Masahiro Miyashita, Soichirou Mori, Norio Shibata, Yoshiaki Nakagawa
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Abstract

Previously, we found that 5-(2,6-dimethoxybenzoylamino)-3-phenylisoxazoles (IOXs) inhibit chitin synthesis in the cultured integument of Chilo suppressalis. In this study, IOXs with various substituents at the para-position of the 3-phenyl ring were synthesized, and the concentrations required to inhibit chitin synthesis to 50% (IC50) were determined for all compounds. The introduction of halogens—such as F, Cl, and Br—and small alkyls—such as Me, Et, Pr, and n-Bu—at the 3-phenyl ring slightly enhanced the activity. However, the activity decreased drastically with the introduction of NO2, CF3, and t-Bu. The quantitative analysis of the substituent effect at the 3-phenyl ring on chitin-synthesis inhibition using the Hansch-Fujita method showed that the hydrophobic substituent with the optimum value was favored for the activity, but the bulky substituent in terms of Es was detrimental to the activity.

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抑制甲壳素合成的 2,6-二甲氧基-N-(3-(4-取代苯基)异恶唑-5-基)苯甲酰胺的定量结构-活性关系
此前,我们发现 5-(2,6-二甲氧基苯甲酰氨基)-3-苯基异噁唑(IOXs)可抑制抑虱培养体中几丁质的合成。本研究合成了在 3-苯基环的对位上具有不同取代基的 IOXs,并测定了所有化合物抑制几丁质合成至 50%所需的浓度(IC50)。在 3-苯基环上引入卤素(如 F、Cl 和 Br)和小烷基(如 Me、Et、Pr 和 n-Bu)会略微提高活性。然而,引入 NO2、CF3 和 t-Bu 后,活性急剧下降。利用 Hansch-Fujita 方法定量分析了 3-苯基环上的取代基对甲壳素合成抑制作用的影响,结果表明,具有最佳值的疏水取代基有利于活性的提高,而以 Es 计的笨重取代基则不利于活性的提高。
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来源期刊
Journal of Pesticide Science
Journal of Pesticide Science 农林科学-昆虫学
CiteScore
4.30
自引率
4.20%
发文量
28
审稿时长
18-36 weeks
期刊介绍: The Journal of Pesticide Science publishes the results of original research regarding the chemistry and biochemistry of pesticides including bio-based materials. It also covers their metabolism, toxicology, environmental fate and formulation.
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