Synthesis, Crystal Structure and Insecticidal Activity of N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8- hexahydrocyclohepta[c]pyrazole-3-carboxamide
邓希乐;周小毛;王赞永;芮昌辉;杨新玲
a (Hunan Agriculture Biotechnology Research Institute,Hunan Academy of Agricultural Sciences, Changsha 410125, China)
b (Department of Applied Chemistry, College of Science,China Agricultural University, Beijing 100193, China)
c (Laboratory of Integrated Pest Management in Crops, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China)
Synthesis, Crystal Structure and Insecticidal Activity of N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8- hexahydrocyclohepta[c]pyrazole-3-carboxamide
DENG Xi-Le;ZHOU Xiao-Mao;WANG Zan-Yong;RUI Chang-Hui;YANG Xin-Ling
a (Hunan Agriculture Biotechnology Research Institute,Hunan Academy of Agricultural Sciences, Changsha 410125, China)
b (Department of Applied Chemistry, College of Science,China Agricultural University, Beijing 100193, China)
c (Laboratory of Integrated Pest Management in Crops, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China)
The title compound N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8-hexahydrocy- clohepta[c]pyrazole-3-carboxamide 5 (C21H22N4O, Mr = 346.42) has been synthesized and structurally characterized by IR, 1H NMR, 13C NMR, H RMS and single-crystal X-ray diffraction. The crystal crystallizes in monoclinic system, space group P21/n with a = 8.668(2), b = 22.236(4), c = 9.539(2) Å, β = 108.68(3)°, V = 1786.4(7) Å3, Z = 4, Dx = 1.288 g/cm-3, F(000) = 736, μ(MoKa) = 0.649 mm-1, the final R = 0.0354 and wR = 0.0933 with 3234 observed reflections with I > 2σ(I). The benzene and pyrazole rings are nearly coplanar with a dihedral angle of 50.977(46)°. The dihedral angle between the central pyrazole and pyridine rings is 11.688(46)°. No classical hydrogen bonds were found in the molecules. Two adjacent molecules in crystal packing of compound 5 were linked by two intramolecular hydrogen-bonding interactions C(15)–H(15)•••O(1) to generate a stable structure. Compound 5 had weak insecticidal activity against the diamondback moth (Plutella xylostella), but exhibited good activity against cotton bollworm (Helicoverpa armigera).
The title compound N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8-hexahydrocy- clohepta[c]pyrazole-3-carboxamide 5 (C21H22N4O, Mr = 346.42) has been synthesized and structurally characterized by IR, 1H NMR, 13C NMR, H RMS and single-crystal X-ray diffraction. The crystal crystallizes in monoclinic system, space group P21/n with a = 8.668(2), b = 22.236(4), c = 9.539(2) Å, β = 108.68(3)°, V = 1786.4(7) Å3, Z = 4, Dx = 1.288 g/cm-3, F(000) = 736, μ(MoKa) = 0.649 mm-1, the final R = 0.0354 and wR = 0.0933 with 3234 observed reflections with I > 2σ(I). The benzene and pyrazole rings are nearly coplanar with a dihedral angle of 50.977(46)°. The dihedral angle between the central pyrazole and pyridine rings is 11.688(46)°. No classical hydrogen bonds were found in the molecules. Two adjacent molecules in crystal packing of compound 5 were linked by two intramolecular hydrogen-bonding interactions C(15)–H(15)•••O(1) to generate a stable structure. Compound 5 had weak insecticidal activity against the diamondback moth (Plutella xylostella), but exhibited good activity against cotton bollworm (Helicoverpa armigera).
This study was financially supported by the National Key Research and Development Plan (No. 2017YFD0200504) and Hunan Provincial Science and Technology Plan Project (No. 2016RS2012)
通讯作者:
yangxl@cau.edu.cn
E-mail: yangxl@cau.edu.cn
引用本文:
邓希乐;周小毛;王赞永;芮昌辉;杨新玲. Synthesis, Crystal Structure and Insecticidal Activity of N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8- hexahydrocyclohepta[c]pyrazole-3-carboxamide[J]. 结构化学, 2018, 37(4): 551-556.
DENG Xi-Le;ZHOU Xiao-Mao;WANG Zan-Yong;RUI Chang-Hui;YANG Xin-Ling. Synthesis, Crystal Structure and Insecticidal Activity of N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8- hexahydrocyclohepta[c]pyrazole-3-carboxamide. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 37(4): 551-556.
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