Chemistry Department, College of Science, Jouf University, P.O. Box 2014, Sakaka, Saudi Arabia.
Chemistry Department, Faculty of Science, Aswan University, P.O. Box81528, Aswan, Egypt.
Chem Biodivers. 2023 Jul;20(7):e202300559. doi: 10.1002/cbdv.202300559. Epub 2023 Jul 4.
Treatment of p-tosyloxybenzaldehyde (1) with ethyl cyanoacetate afforded ethyl 2-cyano-3-(4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)acrylate (2) which reacted with some active methylene derivatives under microwave irradiation in presence of ammonium acetate yielded pyridine derivatives 3-7. On the other hand, when treatment of compound 1 with thiosemicarbazide gave 4-tosyloxybenzylidenethiosemicarbazone (8), which allowed to react with some active methylene compounds, such as: ethyl bromoacetate, chloroacetonitrile or phenacyl bromide derivatives gave thiazole derivatives 9-13. The structure of all products were confirmed by elemental and spectroscopic analyses such as IR, H-NMR, CNMR and mass spectra. The advanced of this method are short reaction time (3-7 min), excellent yield, pure products, and low-cost processing. In the final category, the toxicological characteristics of all compounds were tested towards Saissetia oleae (Olivier, 1791) (Hemiptera: Coccidae). With respect to the LC values. It has been found that compound 3 possesses the highest insecticidal bioefficacy compared with other products, with values of 0.502 and 1.009 ppm, for nymphs and adults female, respectively. This study paves the way towards discovering new materials for potential use as insecticidal active agents.
对对甲苯磺酰基苯甲醛（1）进行氰乙酸乙酯处理，得到乙酯 2-氰基-3-（4-（（4-甲基苯磺酰基）氧基）苯基）丙烯酸酯（2），在微波辐射下，该酯与一些活泼亚甲基衍生物在醋酸铵存在下反应生成吡啶衍生物 3-7。另一方面，当化合物 1 与硫代卡巴肼反应时，得到 4-对甲苯磺酰基亚苄基硫代卡巴腙（8），该腙可以与一些活泼亚甲基化合物反应，如：溴乙酸乙酯、氯乙腈或苯甲酰溴衍生物，生成噻唑衍生物 9-13。所有产物的结构均通过元素和光谱分析（如 IR、1H-NMR、13C-NMR 和质谱）得到证实。该方法的优点是反应时间短（3-7 分钟）、产率高、产物纯净、加工成本低。在最后一类中，对所有化合物的毒理学特征进行了测试Saissetia oleae（Olivier，1791）（半翅目：盾蚧科）。就 LC 值而言。已发现化合物 3 与其他产物相比，具有最高的杀虫生物功效，对若虫和成虫雌虫的 LC 值分别为 0.502 和 1.009 ppm。本研究为发现潜在的杀虫活性物质铺平了道路。
