5-Methyl-1,2,3-thiadiazoles Synthesized via Ugi Reaction and Their Fungicidal and Antiviral Activities

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 13; pp. 7846 - 7855
• Main Authors: Zheng, Qingxiang, Mi, Na, Fan, Zhijin, Zuo, Xiang, Zhang, Haike, Wang, Huan, Yang, Zhikun
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 14.07.2010; Amer Chemical Soc
• Subjects: 5-methyl-1,2,3-thiadiazoles; Agriculture; Agriculture, Multidisciplinary; antifungal properties; Antiviral Agents - chemical synthesis; Antiviral Agents - chemistry; Antiviral Agents - pharmacology; antiviral properties; Biological and medical sciences; chemical reactions; Chemistry; Chemistry, Applied; Crop and Animal Protection Chemistry; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Fungi - drug effects; fungicides; Fungicides, Industrial - chemical synthesis; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; Life Sciences & Biomedicine; pesticides; Physical Sciences; Science & Technology; Structure-Activity Relationship; structure-activity relationships; synthesis; Thiadiazoles - chemical synthesis; Thiadiazoles - chemistry; Thiadiazoles - pharmacology; Ugi reaction; Viruses - drug effects; systemic acquired resistance; fungicide; Ugi reaction; 5-Methyl-1,2,3-thiadiazole; HERPES VIRUSES; 1,2,3-THIADIAZOLE; ELICITORS; BIOLOGICAL-ACTIVITY; RESISTANCE; THIOUREA INHIBITORS; CMV; Resistance; Pesticides; Antiviral; Fungicide
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf1006193

1,2,3-Thiadiazoles, an important synthetic active substructure, are nowadays becoming one of the important branches in novel pesticide development. To develop pesticide candidates with diverse biological activities and probe their structure−activity relationship, three series of 5-methyl-1,2,3-thiadiazoles were rationally designed and synthesized using a simple and convenient one-step synthetic procedure via Ugi reaction. Biological activities of the target compounds including fungicidal activity, antivirus activity in vitro and in vivo, and systemic acquired resistance were systematically evaluated. The results indicated that compound III10 showed broad-spectrum of activities against most fungi tested, and compounds I10 and II17 showed excellent potential antivirus activities as compared to positive control agent ribavirin. The preliminary structure−activity relationship was also discussed. The results of these studies indicated that the 5-position-substituted 1,2,3-thiadiazoles exhibited good antivirus activity and were worthy of further study in pesticide development.