925234-63-5Relevant academic research and scientific papers
Novel sulfonamides against Botrytis cinerea with no positive cross-resistance to commercial fungicides: Design, synthesis and SAR study
Cai, Nan,He, Lu,Wang, Kai,Feng, Zhihui,Cui, Zining,Ji, Mingshan,Qi, Zhiqiu,Qin, Peiwen,Li, Xinghai
, (2020)
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 1H NMR, 13C 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.
Synthesis and biological activities of 2-oxocycloalkylsulfonamides
Li, Xinghai,Yang, Xinling,Liang, Xiaomei,Kai, Zhenpeng,Yuan, Huizu,Yuan, Dekai,Zhang, Jianjun,Wang, Ruiqing,Ran, Fuxiang,Qi, Shuhua,Ling, Yun,Chen, Fuheng,Wang, Daoquan
, p. 4538 - 4544 (2008/09/21)
A series of novel 2-oxocycloalkylsulfonamides (4) were synthesized and their structures confirmed by IR, 1H NMR, and elemental analysis. The bioassay showed that they have fair to excellent fungicidal activities against Botrytis cinerea Pers and Sclerotinia sclerotiorum. Among them, compounds 4A10, 4A11, 4A12, 4B2, and 4B3, the EC50 values of which were 2.12, 3.66, 3.96, 2.38, and 2.43 μg/mL, respectively, displayed excellent fungicidal activity against B. cinerea Pers, and are comparable with commercial fungicide procymidone (the EC50 value is 2.45 μg/mL). 3D QSAR against B. cinerea Pers was studied, a statistically significant and chemically meaningful CoMFA model was developed and some compounds which have a high predicted activity were forecasted. In addition, the bioassay also showed that the compounds have good inhibitory activities against human tumor cells HL-60, BGC-823, Bel-7402 and KB. It is interesting to point out that the antitumor activities of compounds 4 are in accordance with their fungicidal activity to a great extent: compounds having relatively best antitumor activities (4A10, 4A11, 4A12, and 4B3) also displayed excellent fungicidal activity.
