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The discovery of HNPC‐A3066: a novel strobilurin acaricide
Author(s) -
Liu Aiping,
Wang Xiaoguang,
Chen Can,
Pei Hui,
Mao Chunhui,
Wang Yongjiang,
He Haijun,
Huang Lu,
Liu Xinping,
Hu Zhibin,
Ou Xiaoming,
Huang Mingzhi,
Yao Jianren
Publication year - 2009
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.1673
Subject(s) - strobilurin , trifluoromethyl , acaricide , chemistry , stereochemistry , ether , substituent , fungicide , medicinal chemistry , alkyl , organic chemistry , biology , azoxystrobin , botany
BACKGROUND: Although more than ten strobilurin analogues have been commercialized since 1996 as fungicides, only one was available as an acaricide as of 2003. To search for novel strobilurin analogues with unique biological activities, a synthetic screening programme was carried out. RESULTS: Syntheses of compounds analogous to the commercialized fungicide metominostrobin and the acaricide fluacrypyrim led to the discovery of a lead compound, ( E )‐2‐{2‐[[3,5‐bis(trifluoromethyl)phenoxy]methyl]phenyl}‐2‐(methoxyimino)‐ N ‐methylacetamide (3b), that showed moderate acaricidal activity against Tetranychus urticae Koch. Compound 3b has a 3,5‐(CF 3 ) 2 ‐phenoxymethyl group instead of the unsubstituted phenoxy substituent in metominostrobin. Optimization of compound 3b was achieved by introducing an oxime ether bridge along with an alkylthio(alkyl) branch in place of the oxymethylene chain between two aromatic moieties, as well as by replacing the methoxyiminoacetamide group with a methoxyacrylate structure, leading to ( E )‐ methyl 2‐{2‐[[[( Z )[1‐(3,5‐bis(trifluoromethyl)phenyl)‐2‐methylthioethylidene]amino]oxy] methyl]phenyl}‐3‐methoxyacrylate (6c) and ( E )‐ methyl 2‐{2‐[[[( Z )[1‐(3,5‐bis(trifluoromethyl)phenyl)‐1‐methylthiomethylidene]amino]oxy]methyl]phenyl}‐3‐methoxyacrylate (9a, HNPC‐A3066). CONCLUSION: The above two compounds (6c, 9a) were shown to exhibit potent acaricidal and fungicidal activity. Compound 9a (HNPC‐A3066) also exhibits larvicidal and ovicidal activities against various acarids. The acaricidal potency is comparable with those of commercial acaricides such as fluacrypyrim, tebufenpyrad and chlorfenapyr. Copyright © 2008 Society of Chemical Industry