Synthesis, Insecticidal Activities, Toxicity Assessment, and Environmental Implications of (R)- and (S)-Proline-Derived Chiral Neonicotinoid Derivatives

IF 2.3 Q1 AGRICULTURE, MULTIDISCIPLINARY ACS agricultural science & technology Pub Date : 2024-08-11 DOI:10.1021/acsagscitech.4c0035010.1021/acsagscitech.4c00350
Tushar Janardan Pawar, Ivette Bravo-Espinoza, Enrique Delgado-Alvarado, Fernando R. Ramos-Morales, Yoshajandith Aguirre-Vidal and José Luis Olivares-Romero*, 
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Abstract

Neonicotinoid insecticides are widely employed in pest control, but their potential environmental implications demand the exploration of safer and more sustainable alternatives. This study encompasses a comprehensive assessment of the synthesis and toxicity of potential insecticide proline-derived chiral neonicotinoid derivatives, explicitly focusing on elucidating their environmental implications. Toxicity evaluation contained multiple models, including brine shrimp (Artemia salina), zebrafish (Danio rerio), and murine models compared with the commonly used insecticide dinotefuran. Enantioselective toxicity was observed in the brine shrimp assay, with the R-enantiomer demonstrating lesser toxicity compared to the S-enantiomer and dinotefuran. In the zebrafish model, dinotefuran induced developmental abnormalities, such as delayed hatching and vertebral column malformation, while the R-enantiomer exhibited relatively lower sensitivity. The murine LD50 study in mice revealed lower toxicity levels for proline-derived insecticides than dinotefuran. Moreover, these chiral neonicotinoid derivatives were successfully synthesized by optimizing the synthetic routes. The synthesis involved specific starting materials and reaction steps, following established protocols. This study contributes valuable insights into the toxicity profiles of proline-derived chiral neonicotinoid derivatives and underscores the significance of assessing their environmental implications. The synthesized compounds provide a foundation for developing safer and more sustainable insecticides to mitigate the environmental risks associated with prevailing pest control practices.

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(R)-和(S)-脯氨酸衍生手性新烟碱衍生物的合成、杀虫活性、毒性评估和环境影响
新烟碱类杀虫剂被广泛用于害虫控制,但其潜在的环境影响要求人们探索更安全、更可持续的替代品。本研究对潜在杀虫剂脯氨酸手性新烟碱类衍生物的合成和毒性进行了全面评估,明确侧重于阐明其对环境的影响。毒性评估包含多种模型,包括卤虾(Artemia salina)、斑马鱼(Danio rerio)和小鼠模型,并与常用杀虫剂克百威进行了比较。在盐水虾试验中观察到了对映体选择性毒性,与 S-对映体和克百威相比,R-对映体的毒性较低。在斑马鱼模型中,地诺呋喃会诱发发育异常,如孵化延迟和脊椎柱畸形,而R-对映体的敏感性相对较低。小鼠半数致死剂量研究表明,脯氨酸衍生杀虫剂的毒性水平低于克百威。此外,通过优化合成路线,成功合成了这些手性新烟碱类衍生物。合成过程涉及特定的起始材料和反应步骤,并遵循既定的操作规程。这项研究有助于深入了解脯氨酸手性新烟碱衍生物的毒性特征,并强调了评估其环境影响的重要性。合成的化合物为开发更安全、更可持续的杀虫剂奠定了基础,以减轻当前害虫控制方法带来的环境风险。
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