Synthesis and fungicidal activity of tubulin polymerisation promoters. Part 2: Pyridazines

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• 作者：Clemens Lamberth ; ^{clemens.lamberth@syngenta.com} ; Stephan Trah ; Sebastian Wendeborn ; Raphael Dumeunier ; Mikael Courbot ; Jeremy Godwin ; Peter Schneiter
• 关键词：Tubulin ; Pyridazine ; Heterocycle ; Fungicide ; Crop protection
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2012
• 期刊代码：9_09680896
• 类别：ch
• 出版时间：1 May, 2012
• 卷：20
• 期：9
• 页码：2803-2810
• 文件大小：1516 K

摘要

Special tetrasubstituted pyridazines are potent fungicides by promoting the tubulin polymerisation, hereby disrupting the microtubule dynamics in the fungus. They are monocyclic analogs of similar substituted triazolopyrimidines and pyridopyrazines with the same mode of action. The fungicidal activity of these pyridazines was evaluated against the plant pathogens Botrytis cinerea (grey mould), Mycosphaerella graminicola (wheat leaf blotch) and Alternaria solani (potato and tomato early blight). Structure-activity relationship studies revealed the importance of a methyl and a chlorine substituent next to both ring nitrogen atoms and two aryl or heteroaryl groups in the other two pyridazine positions.