Synthesis of 1,2,3-Thiadiazole and Thiazole-Based Strobilurins as Potent Fungicide Candidates / Chen Lai,Zhu Yu-Jie,Fan Zhi-Jin,Guo Xiao-Feng,Zhang Zhi-Ming,Xu Jing-Hua,Song Ying-Qi,Yurievich Morzherin Y.,Belskaya Nataliya P.,Bakulev Vasiliy A. // JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - 2017. - V. 65, l. 4. - P. 745-751.

ISSN/EISSN:

0021-8561 / 1520-5118

Type:

Article

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 mu g/mL, respectively; it was much more active than positive controls enestroburin, kresoxim-methyl, and azoxystrobin with EC50 between 0.06 and 15.12,mu g/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.

Author keywords:

fungicide; strobilurin; 1,2,3-thiadiazole; thiazole; antifungal activity CYTOCHROME BC(1) COMPLEX; DERIVATIVES; DESIGN; AGENTS; INHIBITORS; DISCOVERY; CHEMISTRY; ANALOGS

DOI:

10.1021/acs.jafc.6b05128

Web of Science ID:

ISI:000393355200008

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB 1
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
EISSN	1520-5118
Keywords-Plus	CYTOCHROME BC(1) COMPLEX; DERIVATIVES; DESIGN; AGENTS; INHIBITORS; DISCOVERY; CHEMISTRY; ANALOGS
Research-Areas	Agriculture; Chemistry; Food Science \& Technology
Web-of-Science-Categories	Agriculture, Multidisciplinary; Chemistry, Applied; Food Science \& Technology
Author-Email	fanzj@nankai.edu.cn v.a.bakulev@urfu.ru
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916
Funding-Acknowledgement	National Natural Science Foundation of China {[}21372132]; International Science \& Technology Cooperation Program of China {[}2014DFR41030]; Tianjin Natural Science Foundation {[}14JCYBJC20400]; ``111{''} Project of the Ministry of Education of China {[}B06005]; Ministry of Education and Science of the Russian Federation {[}4.1626.2014/K]
Funding-Text	This work was supported in part by the National Natural Science Foundation of China (Grant No. 21372132), the International Science \& Technology Cooperation Program of China (Grant No.2014DFR41030), the Tianjin Natural Science Foundation (No. 14JCYBJC20400), and the ``111{''} Project of the Ministry of Education of China (Project B06005). V.A.B. thanks the Ministry of Education and Science of the Russian Federation (State Task 4.1626.2014/K).
Number-of-Cited-References	32
Usage-Count-Last-180-days	11
Usage-Count-Since-2013	18
Journal-ISO	J. Agric. Food Chem.
Doc-Delivery-Number	EJ6UP