Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
A series of novel analogues of pyrrolnitrin containing a thiophene moiety were designed and synthesized by a facile method, and their structures were characterized by (1)H nuclear magnetic resonance (NMR) and high-resolution mass spectrometry. The isomers IV-h and V-h were isolated, and their structures were identified by 2D NMR, including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectrometry (NOESY) spectra. Their fungicidal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed excellent fungicidal activities in vitro against Alternaria solani , Gibberella zeae , Physalospora piricola , Fusarium omysporum , and Cercospora arachidicola at the dosage of 50 microg mL(-1). Some compounds shown moderate activity at low dosage. Compound V-h could be considered as a leading structure for further design of agricultural fungicides.
Wang
Ming-Zhong
MZ
State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Xu
Han
H
Feng
Qi
Q
Wang
Li-Zhong
LZ
Wang
Su-Hua
SH
Li
Zheng-Ming
ZM
D000528:Alternaria / Q000187:drug effects; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001203:Ascomycota / Q000187:drug effects; D005670:Fusarium / Q000187:drug effects; D005874:Gibberella / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011764:Pyrrolnitrin / Q000031:analogs & derivatives* / Q000737:chemistry
D000935:Antifungal Agents; D011764:Pyrrolnitrin