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作为昆虫生长调节剂的保幼激素类似物的磺酰基乙酰肼衍生物。

Sulfonyl-acetohydrazide derivatives as juvenile hormone mimics to be insect growth regulators.

作者信息

Kumari Neetika, Chaudhary Manisha, Awasthi Pamita

机构信息

Department of Chemistry, National Institute of Technology, Hamirpur 177005, Himachal Pradesh, India.

Department of Entomology, College of Agriculture, CSKHPKV Palampur, Palampur 176062, Himachal Pradesh, India.

出版信息

Bioorg Chem. 2024 Dec;153:107781. doi: 10.1016/j.bioorg.2024.107781. Epub 2024 Sep 5.

Abstract

The need for targeted pest control strategies has led to the development of juvenile hormone (JH) mimics that selectively disrupt the life cycles of harmful insect species. Present study focuses on the synthesis, characterization and evaluation of sulfonyl-acetohydrazide derivatives (H1-H8) as novel JH mimics on two different insect species, with an emphasis on their insect-specific action. The yellow fever mosquito, Aedes aegypti and cabbage leaf borer, Spodoptera litura, were selected for this investigation. Our results indicate that while these compounds exhibit negligible effects on the development of Aedes aegypti, they demonstrate a potent and specific action against Spodoptera litura. The sulfonyl-acetohydrazide derivatives induced significant developmental abnormalities and increased mortality rates in Spodoptera litura larvae, leading to a marked disruption in their life cycle. Additionally, Density Functional Theory methods were employed to elucidate the electronic structure and corelate the reactivity of the synthesized compounds with the insect growth regulating activity (IGR). The DNA-binding study of synthesized JH analogs has been carried out using UV-vis spectroscopy for toxicity assessment against biomolecule DNA. All the synthesized JH analogs (H1-H8) show IGR action and exhibit better reactivity and reduced toxicity as compared to the commercial in use IGR, pyriproxyfen.

摘要

对靶向害虫控制策略的需求促使了保幼激素(JH)类似物的开发,这些类似物可选择性地破坏有害昆虫物种的生命周期。本研究聚焦于磺酰基乙酰肼衍生物(H1-H8)作为新型JH类似物在两种不同昆虫物种上的合成、表征及评估,重点关注其昆虫特异性作用。本研究选取了埃及伊蚊和斜纹夜蛾作为研究对象。我们的结果表明,虽然这些化合物对埃及伊蚊的发育影响可忽略不计,但它们对斜纹夜蛾表现出强效且特异的作用。磺酰基乙酰肼衍生物在斜纹夜蛾幼虫中诱导了显著的发育异常并提高了死亡率,导致其生命周期明显中断。此外,采用密度泛函理论方法阐明合成化合物的电子结构,并将其反应活性与昆虫生长调节活性(IGR)相关联。已使用紫外可见光谱法对合成的JH类似物进行DNA结合研究,以评估其对生物分子DNA的毒性。所有合成的JH类似物(H1-H8)均表现出IGR作用,并且与市售IGR吡丙醚相比,具有更好的反应活性和更低的毒性。

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