BACKGROUND Optimization studies on a high-throughput screening (HTS) hit led to the discovery of a series of N-(6-arylpyridazin-3-yl)amides with insecticidal activity. It was hypothesized that the isosteric replacement of the pyridazine ring with a 1,3,4-thiadiazole ring could lead to more potent biological activity and/or a broader sap-feeding pest spectrum. The resulting N-(5-aryl-1,3,4-thiadiazol-2-yl)amides were explored as a new class of insecticides. RESULTS Several methods for 2-amino-1,3,4-thiadiazole synthesis were used for the preparation of key synthetic intermediates. Subsequent coupling to variously substituted carboxylic acid building blocks furnished the final targets, which were tested for insecticidal activity against susceptible strains of Aphis gossypii (Glover) (cotton aphid), Myzus persicae (Sulzer) (green peach aphid) and Bemisia tabaci (Gennadius) (sweetpotato whitefly). CONCLUSION Structure-activity relationship (SAR) studies on both the amide tail and the aryl A-ring of novel N-(5-aryl-1,3,4-thiadiazol-2-yl)amides led to a new class of insecticidal molecules active against sap-feeding insect pests. © 2016 Society of Chemical Industry.

中文翻译：

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新型杀虫剂：N-（5-芳基-1,3,4-噻二唑-2-基）酰胺的合成及生物活性。

背景技术对高通量筛选（HTS）命中的优化研究导致发现了一系列具有杀虫活性的N-（6-芳基吡啶并嗪-3-基）酰胺。据推测，用1,3,4-噻二唑环等位取代哒嗪环可导致更强的生物学活性和/或更宽泛的汁液喂养害虫谱。研究了所得的N-（5-芳基-1,3,4-噻二唑-2-基）酰胺作为一类新型的杀虫剂。结果几种2-氨基-1,3,4-噻二唑合成方法被用于制备关键的合成中间体。随后与各种取代的羧酸构件的偶联提供了最终的靶标，并测试了其对棉蚜（Glover）（棉蚜）易感菌株的杀虫活性，桃蚜（Sulzer）（桃蚜）和烟粉虱（Gennadius）（粉虱粉虱）。结论新型N-（5-芳基-1,3,4-噻二唑-2-基）酰胺的酰胺尾部和芳基A环的结构-活性关系（SAR）研究导致了一类新的杀虫分子积极抑制树液喂养的害虫。©2016年化学工业协会。