The design and synthesis of the broad-spectrum fungicide, florylpicoxamid, embodies multiple Green Chemistry principles. The active ingredient was strategically designed to deliver maximum biological activity and rapidly degrade after application to minimize its enviromental impact. Unlike many chiral crop protection chemicals, florylpicoxamid was purposely developed as a single stereoisomer to minimize the dose rate of this product in field applications and avoid any potential environmental burdens of its less active stereoisomers. Fortunately, the most efficacious stereoisomer of the natural product-inspired active ingredient can be derived from the natural antipodes of lactic acid and alanine. The principles of Green Chemistry were also used to improve the synthetic route originally developed for structure–activity relationship studies, resulting in a convergent stereoselective synthesis that is more sustainable and cost-effective. The streamlined 2^nd generation route decreases the use of protecting groups and utilizes safer reaction solvents. Development of a novel synthetic sequence to the 2,3,4-trisubstituted pyridine motif from furfural further increased the renewable carbon content of the active ingredient to nearly 50%. Throughout process development, improved reaction conditions and industrially-preferred alternatives were identified to replace hazardous reagents for key transformations. In all, the holistic use of Green Chemistry principles in the design and synthesis of florylpicoxamid will provide farmers with a highly sustainable product for crop disease management.

中文翻译：

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衍生自可再生原料的杀菌剂florylpicoxamid的设计与合成

广谱杀菌剂florylpicoxamid的设计和合成体现了多种绿色化学原理。该活性成分经过战略性设计，可提供最大的生物活性并在施用后迅速降解，以最大程度地降低其对环境的影响。与许多手性农作物保护化学品不同，氟吡草胺是作为单一的立体异构体开发的，目的是最大程度地减少田间应用中该产品的剂量率，并避免其活性较低的立体异构体对环境造成的任何潜在负担。幸运的是，天然产物启发的活性成分中最有效的立体异构体可以衍生自乳酸和丙氨酸的天然对映体。绿色化学原理还被用于改善最初为结构-活性关系研究而开发的合成途径，导致聚合的立体选择性合成更可持续和更具成本效益。精简2^第一种生成途径减少了保护基的使用，并使用了更安全的反应溶剂。从糠醛向2,3,4-三取代吡啶基序的新合成序列的开发进一步将活性成分的可再生碳含量提高到近50％。在整个工艺开发过程中，确定了改善的反应条件和行业首选的替代品，以替代用于关键转化的危险试剂。总之，在设计和合成氟吡草胺中全面使用绿色化学原理将为农民提供一种高度可持续的作物病害管理产品。