Chinese Journal of Organic Chemistry >
Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety
Received date: 2015-04-13
Revised date: 2015-05-29
Online published: 2015-06-04
Supported by
Project supported by the Science and Technology Development Plan of Shandong Province (No. ZR2013GZX20109).
A series of benzimidazol-2-ylcyanoketone oxime ethers containing morpholine moiety (4a～4h) were synthesized from 2-benzimidazolyl acetonitrile, sodium nitrite, chloroacetyl morpholine and haloalkane/benzyl chloride via sequential reactions of oximation, substitution and etherification. The structures of the target compounds were elucidated by IR, NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum by the mycelium growth rate test, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim, among which the compounds containing 4-fluorobenzyl or 4-chlorobenzyl moiety (4e, 4f) have excellent activity.
Key words： oxime ether; benzimidazole; morpholine; antifungal activity
Qu Zhiqiang , Li Fubo , Xing Chengyuan , Jiang Lin . Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2229 -2233 . DOI: 10.6023/cjoc201504018
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