Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

doi:10.6023/cjoc201508008

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 642-647.DOI: 10.6023/cjoc201508008 Previous Articles Next Articles

Notes

新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

温彦鹏^a, 张爽^b, 侯广峰^b, 于颖慧^a,b, 高金胜^a,b

a 黑龙江大学化学化工与材料学院哈尔滨 150080;
b 黑龙江大学农药工程中心哈尔滨 150080

收稿日期:2015-08-07 修回日期:2015-11-06 发布日期:2015-11-16
通讯作者: 于颖慧, 高金胜 E-mail:yuyinghui@hlju.edu.cn
基金资助:
国家自然科学基金(No. 21371052)和黑龙江省博士后科研启动基金(No. LBH-Q14138)资助项目.

Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

Wen Yanpeng^a, Zhang Shuang^b, Hou Guangfeng^b, Yu Yinghui^a,b, Gao Jinsheng^a,b

a School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080;
b Engineering Research Center of Pesticide of Heilongjiang University, Heilongjiang University, Harbin 150080

Received:2015-08-07 Revised:2015-11-06 Published:2015-11-16
Supported by:
Project supported by the the National Natural Science Foundation of China (No. 21371052) and the Heilongjiang Postdoctoral Scientific Research Foundation (No. LBH-Q14138).

1. Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group.PDF(1346KB)

Abstract

To obtain new herbicidal candidates with novel structure and high herbicidal activities, six new pyrazol compounds based on the structure of tembotrione were designed and synthesized. The meta substituent of benzene ring and the cyclohexadione ring in the original tembotrione structure are replaced. The six target compounds were achieved with 3-chloro-2-methylaniline as the starting material after nine steps reactions, namely diazotization, acetylization, oxidation, esterization, bromization, nucleophilic substitution, chlorination and condensation reactions. All the structures of target products and their intermediates are characterized and confirmed by ¹H NMR, ¹³C NMR, FTIR and elemental analysis. Herbicidal activity tests are also conducted for the six compounds. The results show that each compound exhibits certain herbicidal activity toward mustard, chickweed, amur foxtail, chenopodium and polypogon fugax.

Key words: pyrazol, methylsulfonyl, tembotrione, synthesis, reaction conditions, herbicidal activities

Cite this article

Wen Yanpeng, Zhang Shuang, Hou Guangfeng, Yu Yinghui, Gao Jinsheng. Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group[J]. Chin. J. Org. Chem., 2016, 36(3): 642-647.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Su, S.-Q. Modern Agrochem. 2002, (3), 1 (in Chinese). (苏少泉, 现代农药, 2002, (3), 1.)
[2] Beaudegnies, R.; Edmunds, A. J. F.; Fraser, T. E. M.; Hall, R. G.; Hawkes, T. R.; Mitchell G.; Schaetzer, J.; Wendeborn, S.; Wibley, J. Bioorg. Med. Chem. 2009, 17, 4134.
[3] Yang, L.; Zhang, R.-Q.; Ye, F. Modern Agrochem. 2003, (2), 1 (in Chinese). (杨丽, 张荣全, 叶非, 现代农药, 2003, (2), 1.)
[4] Yang, J.-C.; Wu, Q.; Reng, L.-H.; Liu, C.-L. Agrochemicals 2012, 51, 547 (in Chinese). (杨吉春, 吴峤, 任兰会, 刘长令, 农药, 2012, 51, 547.)
[5] Guo, S.; Yang, F.-M.; Zhang, L. Agrochemicals 2001, 40, 20 (in Chinese). (郭胜, 杨福民, 张林, 农药, 2001, 40, 20.)
[6] Cheng, Z.-Z.; Wang, Y.; Gong, K.; Wang, G-H.; Li, W.-B.; Ye, L. Agrochemicals 2013, 52, 328 (in Chinese). (程正载, 王洋, 龚凯, 王光华, 李文兵, 叶龙, 农药, 2013, 52, 328.)
[7] Zou, X.-J.; Gao, S.; Lin, C.-F.; Dong, H.; Zhang, Z.-J. Agrochemicals 2005, 44, 382 (in Chinese). (邹晓锦, 高爽, 林长福, 董海, 张宗俭, 农药, 2005, 44, 382.)
[8] Liu, Y.-X.; Zhou, B.-Q.; Chai, B.-S.; Liu, C.-L. Agrochemicals 2007, 46, 649 (in Chinese). (刘远雄, 邹本勤, 柴宝山, 刘长令, 农药, 2007, 46, 649.)
[9] Fellman, J. H. Methods Enzymol. 1987, 142, 148.
[10] Buckthal, D. J.; Roche, P. A.; Moorehead, T. J.; Forbes, B. J. R.; Hamilton, G. A. Methods Enzymol. 1987, 142, 132.
[11] Zhang, M.; Wei, J.-F.; Bai, Y.-J.; Gao, Y.; Wu, D.; Miao, Y.-Q.; Shi, Z. Chin. J. Org. Chem. 2006, 26, 207 (in Chinese). (张敏, 魏俊发, 白银娟, 高勇, 吴亚, 苗延青, 史真, 有机化学, 2006, 26, 207.)
[12] Sui, X.-F.; Yuan, J.-Y.; Zhou, M.; He, Y.-H. Chin. J. Org. Chem. 2006, 26, 1518 (in Chinese). (隋晓峰, 袁金颖, 周密, 何永洪, 有机化学, 2006, 26, 1518.)
[13] Nayak, M.; Batchu, H.; Batra, S. Tetrahedron Lett. 2012, 53, 4206.
[14] Markovic, V.; Eric, S.; Juranic, Z. D.; Stanojkovic, T.; Ljubinka, J. L.; Rankovic, B.; Kosanic, M.; Joksovic, M. D. Bioorg. Chem. 2011, 39, 18.
[15] Huang, Y. Y.; Lin, H. C.; Cheng, K. M.; Su, W. N.; Sung, K. C.; Lin, T. P.; Huang, J. J.; Lin, S. K.; Wong, F. F. Tetrahedron 2009, 65, 9592.
[16] Mei, S.-K.; Chen, Y.-Z.; Gao, Z.-C. Chin. J. Appl. Chem. 1985, 2, 8 (in Chinese). (梅盛开, 程渝祖, 高忠潮, 应用化学, 1985, 2, 8.)
[17] Cui, R.-R.; Zhang, X.-Z.; Zhang, M.-F. Shangdong Pestic. News 2009, (7), 18 (in Chinese). (崔蕊蕊, 张秀珍, 张梅凤, 山东农药信息, 2009, (7), 18.)
[18] Van Almsick, A.; Willms, L.; Auler, T.; Bieringer, H.; Rosinger, C. US 6376429, 2002 [Chem. Abstr. 2000, 132, 264966].

新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[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]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[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]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.