title: Design, synthesis, and fungicidal activity of macrolactones and macrolactams with a sulfonamide side chain.
abstract: Four series of novel macrolactones and macrolactams12-alkylsulfonamido-1,15-pentadecanlactones ( 5), 12-alkylsulfonamido-15-methyl-1,15-pentadecanlactones ( 6), 12-alkylsulfonamido-1,15-pentadecanlactams ( 7), and N-(alkylsulfonamidoethyl)-1,12-dodecanlactams ( 8)were designed and synthesized from readily available 2-nitrocyclododecanone or cyclododecanone. Their structures were confirmed by (1)H NMR, IR, and elemental analysis. The bioassay showed that these compounds displayed fair to excellent fungicidal activity against Rhizoctonia solani Kuhn and have a gradual increase of fungicidal activity in the order of 6, 7, 8, and 5. Among them, compounds 5a, 5b, and 5c displayed excellent fungicidal activity against R. solani comparable with the commercial fungicide carbendazim. Above results illustrated that the rule on the relationship between the activity and hydrogen-bonding, namely the macrocyclic compounds with a hydrogen-bonding acceptor and a hydrogen-bonding donor on the ring and having a three methylenes distance between two polarizable groups have the best fungicidal activity against R. solani, has a general suitability to the macrocyclic compounds, and pesticide molecules may combine with a target enzyme by hydrogen-bonding. The facts, which compound 6 has a much lower fungicidal activity against R. solani than compound 5 but their difference in chemical structure is only that there is a methyl group on the C15 for compound 6 and none but hydrogen atom on the C15 for compound 5, indicated that a methyl group plays an inhibitory role to the fungicidal activity. It suggests that the existence of a methyl group with a great volume between two polarizable groups would interfere in the interaction of pesticide molecules and the target enzyme.
authors.affiliation: Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, and Institute of Plant Protection, Chinese Academy of Agricultural Science Beijing, People's Republic of China.
authors.forename: Wei-Juan
authors.initials: WJ
authors.lastname: Zhu
authors.forename: Peng
authors.initials: P
authors.lastname: Wu
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Liang
authors.forename: Yan-Hong
authors.initials: YH
authors.lastname: Dong
authors.forename: Jian-Jun
authors.initials: JJ
authors.lastname: Zhang
authors.forename: Hui-Zu
authors.initials: HZ
authors.lastname: Yuan
authors.forename: Shu-Hua
authors.initials: SH
authors.lastname: Qi
authors.forename: Xiang-Qing
authors.initials: XQ
authors.lastname: Meng
authors.forename: Jin-Ping
authors.initials: JP
authors.lastname: Wu
authors.forename: Fu-Heng
authors.initials: FH
authors.lastname: Chen
authors.forename: Dao-Quan
authors.initials: DQ
authors.lastname: Wang
mesh_terms: D001562:Benzimidazoles / Q000494:pharmacology; D002219:Carbamates / Q000494:pharmacology; D015195:Drug Design; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology; D006860:Hydrogen Bonding; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D012232:Rhizoctonia / Q000187:drug effects
chemical_list: D001562:Benzimidazoles; D002219:Carbamates; D005659:Fungicides, Industrial; D047029:Lactams, Macrocyclic; D007783:Lactones; D047028:Macrocyclic Compounds; C006698:carbendazim