Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activity of 5-Cyclohexylidene-2- aminoimidazolin-4-one Derivatives
Received date: 2012-04-25
Revised date: 2012-05-30
Online published: 2012-06-06
Supported by
Project supported by the National Key Technologies R&D Program (No. 2011BAE06B04), the National Natural Science Foundation of China (No. 201172254) and the National Key Laboratory of Elemento-Organic Chemistry in Nankai University (Nos. 0902, 201003).
A series of new 5-cyclohexylidene-2-aminoimidazolin-4-one derivatives 3a～3r were synthesized via Knoevenagel condensation, methylation and substitution reaction using cyclohexanone and 2-thiohydantoin as starting material. Their structures of compounds 3a～3r were confirmed by 1 H NMR, IR, MS techniques and X-ray diffraction. 5-Cyclohexylidene- 2-p-chlorobenzylaminoimidazolin-4-one (3q): Mr＝335.83, C16H18ClN3O·CH4O, Monoclinic, P2(1)/n, ρ＝1.264 g/cm3, F(000)＝712, Z＝4, a＝0.59895(12) nm, b＝1.2161(2) nm, c＝2.4289(5) nm, β＝94.03(3)°. The preliminary bioassay shows that some of the compounds have certain fungicidal activities at the concentration of 50 μg/mL. The EC50 value of 5-cyclohexylidene-2-p-fluorobenzylaminoimidazolin-4-one (3p) against Sclerotinia scleotiorum is 24.37 μg/mL, and that of 3q against Phytophthora capsici is 28.68 μg/mL, respectively.
Lei Jianping , Han Jintao , Xu Zhihong , Dong Hongbo , Wang Mingan . Synthesis and Fungicidal Activity of 5-Cyclohexylidene-2- aminoimidazolin-4-one Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1993 -1998 . DOI: 10.6023/cjoc201204026
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