Design, synthesis and structure-activity relationship of novel oxime ether strobilurin derivatives containing substituted benzofurans.
BACKGROUND
Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with broad spectrum and high activity, a series of novel oxime ether strobilurin derivatives containing substituted benzofurans in the side chain were synthesised and bioassayed.


RESULTS
The synthesised compounds were characterised by (1) H NMR, (13) C NMR, MS and HRMS. Bioassays demonstrated that most target compounds possessed good or excellent fungicidal activities, especially against Erysiphe graminis and Pyricularia oryzae. Furthermore, methyl 3-methoxypropenoate oxime ethers exhibited remarkably higher activities against E. graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. Notably, (E,E)-methyl 3-methoxy-2-{2-[({[5-fluoro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF2) and (E,E)-methyl 3-methoxy-2-{2-[({[5-chloro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF3) were identified as the most promising candidates for further study.


CONCLUSIONS
The present work demonstrates that oxime ether strobilurin derivatives containing benzofurans can be used as possible lead compounds for developing novel fungicides.
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China.
Ya-Qiang
YQ
Xie
Yi-Bing
YB
Huang
Jian-She
JS
Liu
Li-Yi
LY
Ye
Li-Ming
LM
Che
Song
S
Tu
Chang-Ling
CL
Liu
D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008689:Methacrylates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D005231:Fatty Acids, Unsaturated; D005659:Fungicides, Industrial; D008689:Methacrylates; D010091:Oximes
benzofuran; fungicidal activities; oxime ether; strobilurins; structure-activity