Novel sulfonamides against Botrytis cinerea with no positive cross-resistance to commercial fungicides: Design, synthesis and SAR study. Issue 4 (15th February 2020)

• Record Type: Journal Article
• Authors: Cai, Nan; He, Lu; Wang, Kai; Feng, Zhihui; Cui, Zining; Ji, Mingshan; Qi, Zhiqiu; Qin, Peiwen; Li, Xinghai
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 30:Issue 4(2020)
• Publication Date: 2020-02-15
• Subjects: Cycloalkylsulfonamides -- Reductive amination -- Botrytis cinerea -- Fungicidal activity -- SAR -- Cross resistance; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2019.126859
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Thirty-four novel compounds were synthesized using chesulfamide ( N -(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1 H NMR, 13 C NMR, MS and elemental analysis. Additionally, the structure of ( 1S, 2R )-2-((3-bromophenethyl)amino)- N -(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9 ) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea . Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.