title: Synthesis of 2-amino-6-oxocyclohexenylsulfonamides and their activity against Botrytis cinerea.
abstract: BACKGROUND
  With the objective of exploring the fungicidal activity of 2-oxocyclohexylsulfonamides (2), a series of novel 2-amino-6-oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo.
  
  
  RESULTS
  The compounds were characterised by IR, 1H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N-(2-methylphenyl)-2-(2-methylphenylamino)-4,4-dimethyl-6-oxocyclohexenylsulfonamide (13) and N-(2-chlorophenyl)-2-(2-chlorophenylamino)-6-oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC50 values of 8.05 and 10.56 µg mL(-1) respectively. Commercial fungicide procymidone provided an EC50 value of 0.63 µg mL(-1) . The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ-tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N-cyclohexyl-2-(cyclohexylamino)-4,4-dimethyl-6-oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone.
  
  
  CONCLUSIONS
  The present work demonstrated that 2-amino-6-oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea.
authors: Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang, Liaoning, PR China. lixinghai30@yahoo.cn
authors: Xing-Hai
authors: XH
authors: Li
authors: Ming-Shan
authors: MS
authors: Ji
authors: Zhi-Qiu
authors: ZQ
authors: Qi
authors: Xiu-Wei
authors: XW
authors: Li
authors: Yu-Xia
authors: YX
authors: Shen
authors: Zu-Min
authors: ZM
authors: Gu
authors: Yang
authors: Y
authors: Zhang
authors: Song-Hong
authors: SH
authors: Wei
authors: Ying-Zi
authors: YZ
authors: Wang
authors: Dao-Quan
authors: DQ
authors: Wang
mesh_terms: D020171:Botrytis; D003512:Cyclohexanones / Q000138:chemical synthesis*; D005659:Fungicides, Industrial / Q000138:chemical synthesis*; D025282:Mycelium; D013172:Spores, Fungal; D013449:Sulfonamides / Q000138:chemical synthesis*
chemical_list: D003512:Cyclohexanones; D005659:Fungicides, Industrial; D013449:Sulfonamides