Synthesis, Crystal Structure and Biological Activities of 3-Bromo-5-(4-chlorophenyl)-4-cyanopyrrole-N,N-ditnethyl-2-carboxamide

The title compound 3-bromo-5-(4-chlorophenyl)-4-cyanopyrrole-N,N-dimethyl-2-amide (3) was synthesized with 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile (1) and N,N-dimethylformamide (2) by the alpha-C acylation reaction catalyzed by potassium t-butoxide, and characterized by IR, H-1-NMR and X-ray single-crystal diffraction. It crystallizes in monoclinic, space group P2(1)/n with a = 12.789(2), b = 13.783(2), c = 17.980(3) angstrom, beta = 109.230(3)degrees, V = 2992.5 angstrom(3), M-r = 352.62, D-c = 1.565 mg/m(3), Z = 8, mu = 2.924 mm(-1), F(000) = 1408, the final R = 0.0424 and wR = 0.0973 for 3518 observed reflections with I > 2 sigma(I). A total of 23559 reflections were collected, of which 6242 were independent (R-int = 0.0566). The insecticidal, herbicidal and antibacterial activities of compound 3 were determined, and the experimental results showed that the mortality of 3 at the concentration of 100 ppm on the Fipronil against Linnaeus was 76.6%, the growth inhibition rate of 3 against Cynodon Dactylon under the condition of 100 ppm was 35.8% and the inhibitory activity of 3 at the concentration of 25 ppm against Fusarium graminearum reached 50.9%. Hence, the title compound has the value of further research and application prospect.