Approach to thiazole-containing tetrahydropyridines via Aza–Rauhut–Currier reaction and their potent fungicidal and insecticidal activity. Issue 113 (29th November 2016)

• Record Type: Journal Article
• Authors: Zhu, Yu-Jie; Guo, Xiao-Feng; Fan, Zhi-Jin; Chen, Lai; Ma, Liu-Yong; Wang, Hai-Xia; Wei, Yu; Xu, Xuan-Ming; Lin, Jian-Ping; Bakulev, Vasiliy A.
• Is Part Of: RSC advances. Volume 6:Issue 113(2016)
• Page Start: 112704
• Page End: 112711
• Publication Date: 2016-11-29
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra24342h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Insecticidal and fungicidal active thiazole-containing tetrahydropyridine derivatives with accurately predicted 3D QSAR model against Aphis Laburni Kaltenbach and predicted potential anti-fungus target of fumarate reductase without cross resistance were synthesized. Abstract : A convenient and efficient synthesis of multi-substituted thiazole-containing tetrahydropyridine moieties was reported using the phosphine-catalyzed Aza–Rauhut–Currier reaction with excellent yields and diastereoselectivity. Thiazole-containing tetrahydropyridines were further transformed into the corresponding piperidine derivatives. The biological activity of the title compounds was explored; they exhibited moderate insecticidal activity against Aphis laburni Kaltenbach at 100 μg mL. A 3D QSAR model accurately predicted the insecticidal activity of the structurally diverse set of test compounds. Thiazole-containing tetrahydropyridines were active against normal fungi and also had good activity against resistant fungi mutations without cross resistance; thus, these compounds will be valuable for resistance management. The predicted potential fungicidal target of the title compounds is fumarate reductase.