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Design, synthesis and structure–activity relationship of novel oxime ether strobilurin derivatives containing substituted benzofurans
Author(s) -
Xie YaQiang,
Huang YiBing,
Liu JianShe,
Ye LiYi,
Che LiMing,
Tu Song,
Liu ChangLing
Publication year - 2015
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.3819
Subject(s) - strobilurin , chemistry , benzofuran , ether , pyricularia , erysiphe graminis , stereochemistry , fungicide , organic chemistry , azoxystrobin , biology , botany , poaceae , hordeum vulgare
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. CONCLUSION The present work demonstrates that oxime ether strobilurin derivatives containing benzofurans can be used as possible lead compounds for developing novel fungicides. © 2014 Society of Chemical Industry