title: Design, synthesis and fungicidal activity of novel 2-substituted aminocycloalkylsulfonamides.
abstract: A series of novel 2-substituted aminocycloalkylsulfonamides were designed and synthesized by highly selective N-alkylation reaction, whose structures were characterized by1H NMR,13C NMR and HRMS. Among them, the configuration of compounds III12 and III20 were confirmed by X-ray single crystal diffraction. Bioassays demonstrated that the title compounds had considerable effects on different strains of Botrytis cinerea and Pyricularia grisea. Comparing with positive control procymidone (EC50=10.31mg/L), compounds III28, III29, III30 and III31 showed excellent fungicidal activity against a strain of B. cinerea (CY-09), with EC50values of 3.17, 3.04, 2.54 and 1.99mg/L respectively. Their in vivo fungicidal activities were also better than the positive controls cyprodinil, procymidone, boscalid and carbendazim in pot experiments. Moreover, the fungicidal activity of III28 (EC50=4.62mg/L) against P. grisea was also better than that of the positive control isoprothiolane (EC50=6.11mg/L). Compound III28 would be great promise as a hit compound for further study based on the structure-activity relationship.
authors.affiliation: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China.
authors.forename: Caixiu
authors.initials: C
authors.lastname: Liu
authors.affiliation: Key Laboratory of Integrated Pest Management in Crops, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China.
authors.forename: Xiaojing
authors.initials: X
authors.lastname: Yan
authors.affiliation: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China.
authors.forename: Minlong
authors.initials: M
authors.lastname: Wang
authors.affiliation: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China.
authors.forename: Peiwen
authors.initials: P
authors.lastname: Qin
authors.affiliation: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China.
authors.forename: Zhiqiu
authors.initials: Z
authors.lastname: Qi
authors.affiliation: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China.
authors.forename: Mingshan
authors.initials: M
authors.lastname: Ji
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Xingyu
authors.initials: X
authors.lastname: Liu
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, China.
authors.forename: P Vijaya
authors.initials: PV
authors.lastname: Babu
authors.affiliation: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China. Electronic address: xinghai30@163.com.
authors.forename: Xinghai
authors.initials: X
authors.lastname: Li
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, China. Electronic address: ziningcui@scau.edu.cn.
authors.forename: Zi-Ning
authors.initials: ZN
authors.lastname: Cui
mesh_terms: D020171:Botrytis / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D055685:Pyricularia grisea / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D005659:Fungicides, Industrial; C000620853:N-(2-trifluoromethyl-4-chlorophenyl)-2-((2-chlorothiazol-5-yl-methyl)amino)cyclohexylsulfonamide; D013449:Sulfonamides; D013844:Thiazoles
keywords: 2-Aminocycloalkylsulfonamides; Botrytis cinerea; Fungicidal activity; Structure-activity relationship