Synthesis and Bioactivity of 1,3,5-Substituted Pyrazol-4-methylene Cyclopropane Carboxylate

Abstract

Abstract: The title compounds were synthesized by the esterification reaction of 1,3,5-substituted-4-methylol pyrazole with substituted cyclopropane carbonyl chloride,their structure were confirmed by means of ¹H NMRand elementary analysis.The bioassay showed that the lethal of 1,2 against mosquito larvae at 1.5×10^-7mol/Lwere 100%,The killing activities of 1 and 2 were higher than those of pyrethroid insecticides phenothrin(2×10^-6mol/L)and phthalthrin (4×10^-6mol/L).The other compounds 3,5,12 showed a higher antiphytoviral activity against TMV(tobacco mosaic virus)compared with DHT(2.4-dioxohexahydro-1,3,5-triazine).

Key words: Pyrazol, Cyclopropane carboxylate, Insecticide, Virucide

TrendMD:

HUANG Run-Qiu, SONG Jian, FENG Lei. Synthesis and Bioactivity of 1,3,5-Substituted Pyrazol-4-methylene Cyclopropane Carboxylate[J]. Chem. J. Chinese Universities, 1996, 17(7): 1089.

[1]	LI Kangming, LI Yansai, YI Yangjie, XU Leitao, YE Jiao, OU Xiaoming, LI Jianming, HU Aixi. Design, Synthesis and Biological Activity of 5-Pyrazole Carboxamides ^† [J]. Chem. J. Chinese Universities, 2020, 41(4): 716.
[2]	DONG Xinrui, XIA Zhe, WANG Zhenxue, BIAN Qiang, LI Huabin. Design， Synthesis and Biological Activity of Pyrazole-4-carboxamides Compounds Containing 1，2，4，5-Tetrasubstituted Phenyl [J]. Chem. J. Chinese Universities, 2020, 41(12): 2759.
[3]	CUI Siqian, LU Junrui, XIE Zhiqiang, LU Bowei, LIU Jinbiao, LIU Mei, MA Yao, HU Xinlong, LI Jiadong. One-pot Fasion Synthesis of Pyrano[2,3-c]pyrazol-6-one Derivatives^† [J]. Chem. J. Chinese Universities, 2018, 39(4): 688.
[4]	ZHAO Guozheng, FAN Rongrong, YAN Xilin, TANG Wei, TANG Mingfeng, JIA Jianfeng, WU Haishun. Periodic DFT Study on Structural Transformations of Crystalline Hydrazinium 5-Nitramino-3,4-dinitropyrazolate Under High Pressures^† [J]. Chem. J. Chinese Universities, 2018, 39(2): 292.
[5]	HU Xiaoyang, SU Dongping, LI Shimeng, WANG Zhipeng, ZHANG Lirong, LIU Ying, SONG Lianjun, CHEN Zhili, DING Songdong. Extraction of Am(Ⅲ) and Eu(Ⅲ) from Nitric Acid Solution with the Pyridylpyrazole Based Ligand C8-BPP [J]. Chem. J. Chinese Universities, 2017, 38(8): 1324.
[6]	ZHANG Chenglu, SUN Xiaona, LI Chuanyin, CAI Jiying, WANG Jing, LI Yizheng, WANG Huayu. Synthesis and Bioactivities Evaluation of Novel 1-(1,3,5-Triazin-6-yl)-3-methyl-4-(5-phenyl-1,3,4-oxadiazol-2-yl) pyrazole^† [J]. Chem. J. Chinese Universities, 2017, 38(10): 1764.
[7]	ZHANG Luge, XUE Zexu, ZHANG Chong, YAN Hui. Molecular Dynamics Studies on the Selective Deposition of 3(5)-(9-Anthryl) Pyrazole onto Self-assembled Monolayers^† [J]. Chem. J. Chinese Universities, 2016, 37(3): 505.
[8]	WANG Zhinan, WANG Jixiao, SONG Jian, GAO Xue, FENG Xiaodong, SUN Lixian, XING Yongheng. Syntheses, Structures and Photocatalytic Activities of Coordinated Supramolecular Complexes Containing Triazin-pyrazole Ligand^† [J]. Chem. J. Chinese Universities, 2015, 36(8): 1478.
[9]	WANG Zijian, SUN Xiaohong, LIU Yuanfa, CHEN Bang, SHEN Shengqiang, JIN Ruyi, MA Haixia. Synthesis and Biological Activities of 1,2,4-Triazole Schiff Bases Containing Pyrazole Rings^† [J]. Chem. J. Chinese Universities, 2015, 36(7): 1315.
[10]	LI Heng-Dong, SU Xiao-Long, CHEN Ping-Hua, XIE Li-Li, YUAN Yao-Feng. Synthesis and Properties of 5-Ferrocenyl-pyrazoline Derivatives [J]. Chem. J. Chinese Universities, 2013, 34(7): 1653.
[11]	XING Na, SHAN Hui, SONG Ge, WEI Dong-Ming, LI Guang-Hua, SHI Zhan, XING Yong-Heng. Syntheses, Structures and Properties of Two Half-sandwich Cobalt Carboxylate Complexes with Tris(pyrazolyl)borate Ligand [J]. Chem. J. Chinese Universities, 2013, 34(5): 1041.
[12]	YAO Hong-Wei, CUI Can, LI Yong-Qiang, WANG Li-Zhong, LI Zheng-Ming, ZHAO Wei-Guang. Synthesis and Bioactivity of N-(2-Alkoxy-2-substituted phenyl-ethyl)phenyl Amide [J]. Chem. J. Chinese Universities, 2012, 33(07): 1481.
[13]	LI Chun-Yan, ZHUO Ji-Bin, XIE Li-Li, LI Heng-Dong, WANG Wen-Feng, YUAN Yao-Feng*. Synthesis and Crystal Structure of 3-Ferrocenyl-5-aryl-1-benzenesulfonyl Dihydropyrazole Derivatives [J]. Chem. J. Chinese Universities, 2011, 32(6): 1305.
[14]	CAO Yun-Zhu, LI Zhang-Peng, XING Yong-Heng*, WEI Dong-Ming, PU Zhi-Feng, GE Mao-Fa, SHI Zhan. Synthesis, Structure and Mimic Catalytic Activity of Novel Vanadium Haloperoxidase Model Complexes [J]. Chem. J. Chinese Universities, 2011, 32(5): 1025.
[15]	YANG An-Bo, WU Jing, XU Zhu-Xiong, WANG Bing-Xiang*. Studies of 1-Acetyl-3-(2-hydroxyl-4,6-dimethoxylphenyl)- 5-aryl-2-pyrazoline as Fluorescent Sensors for Cu2+ [J]. Chem. J. Chinese Universities, 2011, 32(10): 2306.

Synthesis and Bioactivity of 1,3,5-Substituted Pyrazol-4-methylene Cyclopropane Carboxylate

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments