Abstract
In order to discover new antifungal agrochemicals that could have highly active and novel motifs, thirty-six new 2-acylaminocycloalkylsulfonamides (IV) were synthesized. Their structures were characterized and confirmed by 1H NMR, 13C NMR, IR, MS, elemental analysis and X-ray single crystal diffraction. In vitro and in vivo activities against various Botrytis cinerea strains were evaluated. Bioassay results revealed that most of the title compounds exhibited excellent in vitro fungicidal activity, in which compound IV-26 showed the highest activity against sensitive, low-resistant, moderate-resistant and high-resistant strains of B. cinerea compared with the positive fungicide procymidone. Meanwhile in vivo fungicidal activity of compound IV-31 was better than the commercial fungicides procymidone and chesulfamide in greenhouse trial. The structure activity relationship (SAR) was also discussed and the results were of importance to the structural optimization and development of more potent sulfonamides antifungal agents.
Highlights
As very important sulfur-containing analogs of amino carboxylic acids, 2-aminoethanesulfonic acid was first isolated from ox bile in 19th century by Tiedemann and Gmelin, which name ‘taurine’ was attributed by Gmelin[3,4]
2-aminoethanesulfonic acid had been found as key structural moieties in some natural products, such as dimethyl arsenic aminosulfonate (A, Fig. 1), which was isolated from Sargassum lacerifolium[17]
The synthetic route of title compounds IV-1 to IV-36 was outlined in Fig. 4 using 2-oxycycloalkylsulfonamides as a starting material
Summary
As very important sulfur-containing analogs of amino carboxylic acids, 2-aminoethanesulfonic acid was first isolated from ox bile in 19th century by Tiedemann and Gmelin, which name ‘taurine’ was attributed by Gmelin[3,4]. 2-aminoethanesulfonic acid had been found as key structural moieties in some natural products, such as dimethyl arsenic aminosulfonate (A, Fig. 1), which was isolated from Sargassum lacerifolium[17]. Studies on the synthesis and biological activity of taurine analogues 2-acylaminoethylsulfonamides have been reported frequently. Our group reported a series of 2-oxycycloalkylsulfonamides (H-N, Figs 2 and 3), which possessed highly fungicidal activity[26,27,28,29], of which compound L (chesulfamide, Fig. 3) could be great promise and a lead compound in fungicide research and development. Based on the lead structure of compound L, compounds M and N (Fig. 3) were designed and synthesized with much higher fungicidal activity[30,31,32]
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