Synthesis and biological activity of a new class of insecticides: theN-(5-aryl-1,3,4-thiadiazol-2-yl)amides
| Autor: | Jack G Samaritoni, Maurice Ch Yap, Ricky Hunter, Eckelbarger Joseph D, Jonathan M. Babcock, Negar Garizi, Marshall H. Parker, Buysse Ann M, Yelena Adelfinskaya, Trullinger Tony K |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
0106 biological sciences
Aphid biology 010405 organic chemistry Stereochemistry Aryl Biological activity General Medicine biology.organism_classification 01 natural sciences 0104 chemical sciences Pyridazine 010602 entomology chemistry.chemical_compound chemistry Insect Science Amide Aphis gossypii Botany Structure–activity relationship Myzus persicae Agronomy and Crop Science |
| Zdroj: | Pest Management Science. 73:761-773 |
| ISSN: | 1526-498X |
| Popis: | 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 |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text