Design, synthesis and fungicidal activity of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines.
A series of novel compounds (5-8) was designed and synthesized by integrating the active pharmacophore of the N-phenylpyrimidin-2-amine fungicide with the structure of strobilurin fungicide. The rationale of this approach was to determine if these new compounds exhibit unique biological activity (selectivity and potency) compared with the commercial standards. The title compounds were prepared from 2-(phenylamino)pyrimidin-4-ols (3) by treatment with one equivalent of intermediates (4) containing strobilurin pharmacophores. 2-(Phenylamino)pyrimidin-4-ols (3) were in turn prepared from phenylguanidines (1) and substituted beta-ketoesters (2). Biological activities evaluated in the greenhouse indicated that compounds 5a, 6a and 7a have good fungicidal activity at 25 mg/L, comparable with that of the commercial standards, cyprodinil and azoxystrobin.
Li
Hui-Chao
HC
Agrochemical Discovery Department, Shenyang Research Institute of Chemical Industry, Shenyang 110021, China.
Liu
Chang-Ling
CL
Chai
Bao-Shan
BS
Li
Miao
M
Li
Zhi-Nian
ZN
Yang
Ji-Chun
JC
D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008689:Methacrylates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
D005659:Fungicides, Industrial; D008689:Methacrylates; D011743:Pyrimidines