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Synthesis and insecticidal activities of novel pyrazole oxime ether derivatives with different substituted pyridyl rings
Author(s) -
Fu Cuirong,
Pei Jiang,
Ning Yu,
Liu Min,
Shan Pengcheng,
Liu Jun,
Li Yongqiang,
Hu Fangzhong,
Zhu Youquan,
Yang Huazheng,
Zou Xiaomao
Publication year - 2014
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.3672
Subject(s) - pyrazole , oxime , chemistry , ether , stereochemistry , bioassay , proton nmr , medicinal chemistry , organic chemistry , biology , genetics
BACKGROUND Pyrazole oxime ether derivatives with different substituted pyridyl rings represent new types of compounds that possess good insecticidal and acarcidal activity against Aphis laburni Kaltenbach and Tetranychus cinnabarinus . RESULTS In total, 82 novel pyrazole oxime ether derivatives were synthesized and identified by 1 H NMR, elemental analysis or high‐resolution mass spectrometry, and their insecticidal and acarcidal activities were tested against A. laburni Kaltenbach and T. cinnabarinus . Bioassays showed that at a 200 mg L −1 dosage, one‐third of the compounds displayed high insecticidal activity against A. laburni Kaltenbach (> 90%), whereas most of of the compound II series exhibited excellent acarcidal activity against T. cinnabarinus (> 92%). Most compound II series exhibited good activity in both insecticidal and acarcidal tests. In addition, at a low concentration of 10 mg L −1 , the insecticidal activity of compounds IB9 and IE4 exceeded 90%, and the acarcidal activity of compounds IIB1 and IIB2 was ≥ 95% . CONCLUSION Structure–activity relationships were also examined. Results suggested that the tert ‐butoxycarbonyl group, as well as the position between tert ‐butoxycarbonyl and the atom N of the pyridyl ring, were essential to obtaining the acarcidal activity of the title compounds. © 2013 Society of Chemical Industry