title: Synthesis of 1,2,3-Thiadiazole and Thiazole-Based Strobilurins as Potent Fungicide Candidates.
abstract: Strobilurin fungicides play a crucial role in protecting plants against different pathogens and securing food supplies. A series of 1,2,3-thiadiazole and thiazole-based strobilurins were rationally designed, synthesized, characterized, and tested against various fungi. Introduction of 1,2,3-thiadiazole greatly improved the fungicidal activity of the target molecules. Compounds 8a, 8c, 8d, and 10i exhibited a relatively broad spectrum of fungicidal activity. Compound 8a showed excellent activities against Gibberella zeae, Sclerotinia sclerotiorum, and Rhizoctonia cerealis with median effective concentrations (EC50) of 2.68, 0.44, and 0.01 μg/mL, respectively; it was much more active than positive controls enestroburin, kresoxim-methyl, and azoxystrobin with EC50between 0.06 and 15.12 μg/mL. Comparable or better fungicidal efficacy of compound 8a compared with azoxystrobin and trifloxystrobin against Sphaerotheca fuliginea and Pseudoperonspera cubensis was validated in cucumber fields at the same application dosages. Therefore, compound 8a is a promising fungicidal candidate worthy of further development.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Lai
authors.identifier: http://orcid.org/0000-0002-0722-1514
authors.initials: L
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Yu-Jie
authors.initials: YJ
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Zhi-Jin
authors.identifier: http://orcid.org/0000-0001-5565-0949
authors.initials: ZJ
authors.lastname: Fan
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Xiao-Feng
authors.initials: XF
authors.lastname: Guo
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Zhi-Ming
authors.initials: ZM
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Jing-Hua
authors.initials: JH
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
authors.forename: Ying-Qi
authors.initials: YQ
authors.lastname: Song
authors.affiliation: The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU , 620002 Ekaterinburg, Russia.
authors.forename: Morzherin Y
authors.identifier: http://orcid.org/0000-0002-1333-6676
authors.initials: MY
authors.lastname: Yurievich
authors.affiliation: The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU , 620002 Ekaterinburg, Russia.
authors.forename: Nataliya P
authors.identifier: http://orcid.org/0000-0002-2509-7916
authors.initials: NP
authors.lastname: Belskaya
authors.affiliation: The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU , 620002 Ekaterinburg, Russia.
authors.forename: Vasiliy A
authors.initials: VA
authors.lastname: Bakulev
mesh_terms: D001203:Ascomycota / Q000187:drug effects / Q000502:physiology; D018553:Cucumis sativus / Q000382:microbiology; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010935:Plant Diseases / Q000382:microbiology; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D005659:Fungicides, Industrial; D013830:Thiadiazoles
keywords: 1,2,3-thiadiazole; antifungal activity; fungicide; strobilurin; thiazole