Citation: Zhao Anlin, Liu Shu, Zhu Yongmei, Wang Tao, Luo Jin. Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2, 3-d]pyrimidin-4-ones[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1877-1882. doi: 10.6023/cjoc201612048 shu

Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2, 3-d]pyrimidin-4-ones

Zhao Anlin ^a ,
Liu Shu ^a ,
Zhu Yongmei ^b ,
Wang Tao ^a,, ,
Luo Jin ^a,b,,

a.
Jiangxi Province Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
b.
Analytical & Testing Center, Jiangxi Normal University, Nanchang 330022

Corresponding author: Wang Tao, wangtao@jxnu.edu.cn Luo Jin, jinluo@jxnu.edu.cn
Received Date: 19 December 2019
Revised Date: 19 February 2017
Available Online: 1 July 2017
Fund Project: the National Natural Science Foundation of China 21262018the Natural Science Foundation of Jiangxi Province 20161BAB213072Project supported by the National Natural Science Foundation of China (Nos. 21262018, 21562026) and the Natural Science Foundation of Jiangxi Province (Nos. 20161BAB203085, 20161BAB213072)the Natural Science Foundation of Jiangxi Province 20161BAB203085the National Natural Science Foundation of China 21562026

Figures(1)

In an attempt to discover novel fuse heterocyclic compound with high herbicidal activity, sixteen newly 2-alkythio-thieno[2, 3-d]pyrimidin-4(3H)-ones have been designed and synthesized by the reaction of 3-propyl-6-ethylthieno[2, 3-d]pyrimidine-2-thione with halo-hydrocarbon. Their structures were clearly verified by ¹H NMR, IR, LC-MS and elemental analysis. Preliminary bioassay results indicate that some target compounds have excellent inhibitory activities on barnyard grass and rape. 2-Cyclopentylthio-3-n-propyl-6-ethylthieno[2, 3-d]pyrimidin-4(3H)-one (4e) and 2-n-hexdecylthio-3-n-propyl-6-ethylthieno[2, 3-d]pyrimidin-4(3H)-one (4o) show 100% inhibition rate to barnyard grass at the concentration of 100 mg/L.
- thieno[2, 3-d]pyrimidin-4(3H)-ones,
- synthesis,
- herbicidal activitiess
1. [1]
  Ravindr, V. C.; Barsu, G. K.; Anil, S. B.; Rajesh, H. B. Eur. J Med. Chem. 2003, 34, 89.
2. [2]
  Temple, D. L. US 4054656, 1977[Chem. Abstr. 1977, 88, 37830].
3. [3]
  Panico, A. M.; Santagati, A.; Cardile, V. Colloids Surf. B 2003, 28, 77. doi: 10.1016/S0927-7765(02)00118-2
4. [4]
  Zeng, G. P.; Zheng, P. Acta Chim. Sinica 2012, 70, 759(in Chinese). doi: 10.3866/PKU.WHXB201202023
5. [5]
  Crespo, M. l.; Pages, L. L; Vega, A.; Segarra, V.; Lopez, M.; Domenech, T.; Miralpeix, M.; Beleta, J.; Ryder, H.; Palacios, J. M. J. Med. Chem. 1998, 41, 4021. doi: 10.1021/jm981012m
6. [6]
  Samsonova, N. V.; Kharizomenova, L. A.; Givenv, A. N.; Kaplina, E. K. Pharm. Chem. J. 1981, 15, 645. doi: 10.1007/BF00760666
7. [7]
  Tokio, O.; Katsutoshi, F.; Isamu, N. EP 0356158, 1990[Chem. Abst. 1990, 113, 59210].
8. [8]
  Rosowsky, A.; Chaykovsk, M.; Chen, K. K. N.; Lin, M.; Modest, E. J. J. Med. Chem. 1973, 16, 185. doi: 10.1021/jm00261a002
9. [9]
  Perspicace, E.; Ragno, R.; Ballante, F.; Hesse, S. Eur. J. Med. Chem. 2013, 63, 765. doi: 10.1016/j.ejmech.2013.03.022
10. [10]
  Chen, Y.; Bai, S.; He, W. H.; Yang, G. Z. Chin. J. Org. Chem. 2014, 34, 2362(in Chinese).
11. [11]
  Bozorov, K.; Zhao, J. Y.; Elmuradov, B.; Pataer, a.; Aisa, H. A. Eur. J. Med. Chem. 2015, 102, 552. doi: 10.1016/j.ejmech.2015.08.018
12. [12]
  John, G. R.; Joanne, L.; Elizabeth, D. C. WO 02055524, 2002[Chem. Abstr. 2002, 137, 109287].
13. [13]
  Leistner, S.; Wagner, G.; Guetscharo, M.; Glusa, E. Pharmazie, 1986, 41, 54.
14. [14]
  Wang, H. M.; Guo, S. B.; Hu, Y. G.; Zeng, X. H.; Yang, G. Y. Chin. J. Org. Chem. 2015, 35, 1075(in Chinese).
15. [15]
  Liu, H.; Wang, H. Q.; Liu, Z. J. Bioorg. Med. Chem. Lett. 2007, 38, 2203.
16. [16]
  Shield, M. Eur. J. Rheumatol. Inflammation 1993, 13, 7.
17. [17]
  Palmoski, M. J.; Brandt, K. D. Arthritis Rheum. 1983, 26, 528. doi: 10.1002/(ISSN)1529-0131
18. [18]
  Hess, E. V.; Herman, J. H. Am. J. Med. 1986, 81, 36.
19. [19]
  Redini, F.; Mauviel, A.; Loyau, G.; Pujol, J. P. Agents Actions 1990, 31, 358. doi: 10.1007/BF01997632
20. [20]
  Rainsford, K. D. Am. J. Med. 1999, 107, S27.
21. [21]
  Krell, R. D.; Aharony, D.; Buckner, C. K.; Keith, R. A.; Kusner, E.J.; Snyder, D. W.; Bernstein, P. R.; Matassa, V. G.; Yee, Y. K.; Gilles, R. E. Am. Rev. Respir. Dis. 1990, 141, 978. doi: 10.1164/ajrccm/141.4_Pt_1.978
22. [22]
  Jarvis, B.; Markham, A. Drugs 2000, 59, 891 doi: 10.2165/00003495-200059040-00015
23. [23]
  Krell, R. D.; Aharony, D.; Buckner, C. K; Keith, R. A.; Kusner, E. J.; Snyder, D. W.; Bernstein, P. R.; Matassa, V. G.; Yee, Y. K; Brown, F. J.; Hesp, B.; Giles, R. E. Am. Rev. Respir. Dis. 1990, 141, 978. doi: 10.1164/ajrccm/141.4_Pt_1.978
24. [24]
  Wang, T.; Zheng, C. H.; Liu, S.; Chen, H. Z. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 1543. doi: 10.1080/10426500903127565
25. [25]
  Wang, T. Ph.D. Dissertation, Central China Normal University, Wuhan, 2004(in Chinese).
26. [26]
  Guo, Y. C.; Li, J.; Ma, J. L.; Yu, Z. R.; Wang, H. W.; Zhu, W. J.; Liao, X. C.; Zhao, Y. F. Chin. Chem. Lett. 2015, 26, 755. doi: 10.1016/j.cclet.2015.03.026
1. [1]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
2. [2]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
3. [3]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
7. [7]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
10. [10]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
11. [11]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
12. [12]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C₃N₄ Nanosheets for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
13. [13]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . Simultaneously Improving Inter-Plane Crystallization and Incorporating K Atoms in g-C₃N₄ Photocatalyst for Highly-Efficient H₂O₂ Photosynthesis. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-0. doi: 10.3866/PKU.WHXB202406005
14. [14]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
15. [15]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
16. [16]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
18. [18]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
19. [19]
  Qi Wu , Changhua Wang , Yingying Li , Xintong Zhang . Enhanced photocatalytic synthesis of H₂O₂ by triplet electron transfer at g-C₃N₄@BN van der Waals heterojunction interface. Acta Physico-Chimica Sinica, 2025, 41(9): 100107-0. doi: 10.1016/j.actphy.2025.100107
20. [20]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1415)
HTML views(130)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142