Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives

doi:10.6023/cjoc201406017

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 422-427.DOI: 10.6023/cjoc201406017 Previous Articles Next Articles

Articles

含二氟甲基取代的吡唑酰胺类化合物的合成及杀菌活性

刘婷婷^a, 倪芸^a, 钟良坤^a, 黄红英^b, 胡伟群^b, 许天明^b, 谭成侠^a

a 浙江工业大学化学工程学院杭州 310014;
b 中化蓝天集团有限公司浙江省化工研究院有限公司杭州 310023

收稿日期:2014-06-13 修回日期:2014-09-22 发布日期:2014-10-22
通讯作者: 谭成侠 E-mail:tanchengxia@zjut.edu.cn
基金资助:
“十二五”国家科技支撑计划(No. 2011BAE06B03-01)、浙江省重点科技创新团队(No. 2010R50018)资助项目.

Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives

Liu Tingting^a, Ni Yun^a, Zhong Liangkun^a, Huang Hongying^b, Hu Weiqun^b, Xu Tianming^b, Tan Chengxia^a

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
b Sinochem Lantian Zhejiang Research Institute of Chemical Industry Co. Ltd, Hangzhou 310023

Received:2014-06-13 Revised:2014-09-22 Published:2014-10-22
Supported by:
Supported by the Key Innovation Team of Science and Technology in Zhejiang Province (No. 2010R50018), and the Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03-01).

1. Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives.PDF(3735KB)

Abstract

In the course of discovering novel fungicidal lead compounds with high activity and safety, 13 new difluoromethyl substituted carboxamide derivatives were designed and synthesized according to the principle of bioactive substructure combination. Their structures were confirmed by ¹H NMR, MS and HRMS. The fungicidal activities of these compounds were evaluated. Preliminary bioassay showed that most of the title compounds showed good fungicidal activity at 200 mg/L.

Key words: isoxazole, pyrazole amides, synthesis, fungicidal activity

Cite this article

Liu Tingting, Ni Yun, Zhong Liangkun, Huang Hongying, Hu Weiqun, Xu Tianming, Tan Chengxia. Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives[J]. Chin. J. Org. Chem., 2015, 35(2): 422-427.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Liu, X. H.; Zhao, W. G.; Wang, B. L.; Li, Z. M. Res. Chem. Intermed. 2012, 28, 1999.
[2] Tong, J. Y.; Shi, Y. X.; Liu, X. H.; Sun, N. B.; Li, B. J. Chin. J. Org. Chem. 2012, 32, 2373 (in Chinese). (童建颖, 石延霞, 刘幸海, 孙娜波, 李宝聚, 有机化学, 2012, 32, 2373.)
[3] Su, N. N.; Li, Y.; Yu, S. J.; Zhang, X.; Liu, X. H.; Zhao, W. G. Res. Chem. Intermed. 2013, 39, 759.
[4] Tong, J. Y.; Wu, H. K.; Sun, N. B.; Liu, X. H. Chin. J. Struct. Chem. 2013, 32, 607.
[5] Hu, L.-M.; Li, X.-S.; Chen, Z.-Y.; Liu, Z.-J. Chin. J. Org. Chem. 2003, 23, 1131 (in Chinese). (胡利明, 李学恕, 陈致远, 刘钊杰, 有机化学, 2003, 23, 1131.)
[6] (a) Xe, F.; Liu, T.-T.; Yang, G.; Yuan, J.; Kong, X.-L.; Xu, T.-M.; Tan, C.-X. Chin. J. Org. Chem. 2013, 33, 2596 (in Chinese). (谢峰, 刘婷婷, 杨果, 袁静, 孔小林, 许天明, 谭成侠, 有机化学, 2013, 33, 2596.)
(b) Ma, Q.-S.; Liu, X.-H.; Weng, J.-Q.; Li, Y.-S.; Zhang, M.; Zhang, X.-Y.; Tan, C.-X. Chin. J. Org. Chem. 2013, 33, 1749 (in Chinese). (马青森, 刘幸海, 翁建全, 李永曙, 张旻, 张向阳, 谭成侠, 有机化学, 2013, 33, 1749.)
[7] Ohuchi, S.; Okada, S. JP 10338589, 1998 [Chem. Abstr. 1998, 130, 120912y].
[8] Liu, C.-L. Pesticide 1998, 37(8), 1 (in Chinese). (刘长令, 农药, 1998, 37(8), 1.)
[9] Doyle, F. P.; J. C.; Long, A. A. W.; Nayler, J. H. C.; Stove, E. R. J. Am. Chem. Soc. 1963, 85, 5845.
[10] Kang, Y. K.; Shin, K. J.; Yoo, K. H.; Seo, K. J.; Hong, C. Y.; Lee, C. S.; Park, S. Y.; Kim, D. T.; Park, S. W. Bioorg. Med. Chem. Lett. 2000, 10, 95.
[11] Josef, E.; Harald, W.; Camilla, C.; Hans, T. WO 2007065661, 2007 [Chem. Abstr. 2007, 147, 72747].
[12] Dunkel, R.; Beeck, S.; Greul, J. N.; Wachendorf-Neumann, U.; Dahmen, P.; Voerste, A. WO 2008014905, 2008 [Chem. Abstr. 2008, 148, 239197].
[13] Stierli, D.; Taylor, J. J.; Walter, H.; Worthington, P. A.; Rajan, R. WO 2007141009, 2007 [Chem. Abstr. 2007, 148, 55044].
[14] Stierli, D.; Taylor, J. J.; Walter, H.; Worthington, P. A. WO 2007134799, 2008 [Chem. Abstr. 2008, 148, 168714].
[15] EP 1997808, 2008 [Chem. Abstr. 2008, 150, 5730].
[16] (a) Du, G.-J.; Chen, D.-L.; Lu, R.-J.; Wang, X.-J.; Yan, M. Chin. J. Org. Chem. 2009, 29, 1576 (in Chinese). (杜光剑, 陈东亮, 卢锐炯, 王晓军, 鄢明, 有机化学, 2009, 29, 1576.)
(b) Zhou, Y.-L.; Shen, S.-W.; Liu, F.-M. Chin. J. Org. Chem. 2010, 30, 1343 (in Chinese). (周英雷, 沈松伟, 刘方明, 有机化学, 2010, 30, 1343.)
[17] Hu, W.-Q.; Zhu, W.-G.; Chen, D.-H. Chin. J. Pestic. Sci. 2007, 9, 240 (in Chinese). (胡伟群, 朱卫刚, 陈定花, 农药学学报, 2007, 9, 240.)
[18] Stierli, D.; Walter, H.; Rajan, R. WO 2009127726, 2009 [Chem. Abstr. 2009, 151, 470195].

含二氟甲基取代的吡唑酰胺类化合物的合成及杀菌活性

Synthesis and Fungicidal Activity of Difluoromethy Substituted Carboxamide Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.