Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups
2017
Wang, J.J. ((Nanjing Agricultural University, Nanjing (China). College of Science, Department of Chemistry), (Nanjing Agricultural University, Nanjing (China). Jiangsu Key Laboratory of Pesticide Science)) | Si, W.J. | Chen, M. | Lu, A.M. | Zhang, W.H. | Yang, C.L.
Substituted phenylhydrazone moieties and two carbonate groups were merged in one molecule scaffold to obtain 48 novel compounds. sup(1)H and sup(13)C NMR, MS, elemental analysis, and X-ray single-crystal diffraction were used to confirm their structures. Bioassay results revealed that some of the compounds have strong antifungal activities against Botrytis cinerea, Rhizoctonia solani, and Colletotrichum capsici (especially Rhizoctonia solani). Compound 5H1 is the most promising of the tested compounds against R. solani with an ECsub(50) value of 1.91 mg/L, which is comparable with the positive control fungicide drazoxolon (1.94 mg/L). The structure-activity relationships against R. solani formed three rules: 1) small carbonate groups may improve the antifungal activity of the title compounds; 2) electron-withdrawing groups at the phenyl ring of phenylhydrazone are preferable to their non-substituted counterparts; and 3) halogen at the para position is more beneficial than at the ortho or meta position.
Show more [+] Less [-]AGROVOC Keywords
Bibliographic information
This bibliographic record has been provided by Agriculture, Forestry and Fisheries Research Information Technology Center