Eckelbarger Joseph D, Parker Marshall H, Yap Maurice Ch, Buysse Ann M, Babcock Jonathan M, Hunter Ricky, Adelfinskaya Yelena, Samaritoni Jack G, Garizi Negar, Trullinger Tony K
Dow AgroSciences LLC, Indianapolis, IN, USA.
Sealed Air, Charlotte, NC, USA.
Pest Manag Sci. 2017 Apr;73(4):761-773. doi: 10.1002/ps.4359. Epub 2016 Aug 30.
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.
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).
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.
对高通量筛选（HTS）命中物的优化研究导致发现了一系列具有杀虫活性的N-（6-芳基哒嗪-3-基）酰胺。据推测，用1,3,4-噻二唑环等排取代哒嗪环可能会导致更强的生物活性和/或更广泛的吸食汁液害虫谱。由此产生的N-（5-芳基-1,3,4-噻二唑-2-基）酰胺被作为一类新型杀虫剂进行了研究。
使用了几种合成2-氨基-1,3,4-噻二唑的方法来制备关键合成中间体。随后与各种取代的羧酸结构单元偶联得到了最终目标化合物，并对其针对棉蚜（Aphis gossypii (Glover)）、桃蚜（Myzus persicae (Sulzer)）和烟粉虱（Bemisia tabaci (Gennadius)）敏感品系的杀虫活性进行了测试。
对新型N-（5-芳基-1,3,4-噻二唑-2-基）酰胺的酰胺尾部和芳基A环进行的构效关系（SAR）研究导致了一类对吸食汁液害虫有活性的新型杀虫分子。© 2016化学工业协会。
