UDの研究者が、生態学的により安全な殺虫剤を促進する可能性のある新しいバイオベースの殺虫成分を報告(UD researchers report new bio-based insecticidal ingredients with potential to drive ecologically safer pesticides)

2024-09-24 デラウェア大学 (UD)

＜関連情報＞

• https://www.udel.edu/udaily/2024/september/ecologically-safer-biobased-insecticidal-ingredients-Dionisios-Vlachos-Michael-Crossley/
• https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.202400824

バイオマス由来で標的を特定し、生態学的により安全な殺虫活性成分 Biomass-Derived, Target Specific, and Ecologically Safer Insecticide Active Ingredients

Tejas Goculdas, Maximus Ramirez, Michael Crossley, Sunitha Sadula, Dionisios G. Vlachos
ChemSusChem  Published: 26 June 2024
DOI:https://doi.org/10.1002/cssc.202400824

Graphical Abstract

A two-step strategy transforms biobased aldehydes into carbamate insecticides using benign chemistries and renewable materials. Furan-based carbamates show selective potency against target pests with positive ecological profiles. Synthesizing six additional carbamates proves the approach′s broad applicability. Techno-economic analysis confirms the method′s economic feasibility for producing carbamate insecticides.

Abstract

With the continuous increase in food production to support the growing population, ensuring agricultural sustainability using crop-protecting agents, such as pesticides, is vital. Conventional pesticides pose significant environmental risks, prompting the need for eco-friendly alternatives. This study reports the synthesis of new amide-based insecticidal active ingredients from biomass-derived monomers, specifically furfural and vanillin. The process involves reductive amination followed by carbonylation. The synthesis of the furfural-based carbamate yield reaches a cumulative 88 %, with catalysts Rh/Al₂O₃ and La(OTf)₃ being recyclable at each stage. Insecticidal activity assessments reveal that the furfural carbamate exhibits competitive performance, achieving an LC₅₀ of 254.22 μg/cm², compared to 251.25 μg/cm² for carbofuran. Ecotoxicity predictions indicate significantly lower toxicity levels toward non-target aquatic and terrestrial species. The importance of the low octanol-water partition coefficient of the biobased carbamate, attributed to the oxygen heteroatom and electron density of the furan ring, is discussed in detail. Building on these promising results, the synthesis strategy was extended to six other biobased aldehydes, resulting in a diverse portfolio of biomass-derived carbamates. A techno-economic analysis reveals a minimum selling price of 11.1 $/kg, only half that of comparable carbamates, demonstrating the economic viability of these new biobased insecticides.