Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones

doi:10.6023/cjoc201410041

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1166-1172.DOI: 10.6023/cjoc201410041 Previous Articles Next Articles

Notes

新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮的合成及杀菌活性

阮铃莉^a, 范人杰^a, 刘幸海^a, 陈杰^b, 翁建全^a

a 浙江工业大学化学工程学院杭州 310032;
b 国家南方农药创制中心浙江基地生测部杭州 310023

收稿日期:2014-10-31 修回日期:2014-12-14 发布日期:2015-01-07
通讯作者: 翁建全 E-mail:jqweng@zjut.edu.cn
基金资助:
国家自然科学基金(No.30900959)和浙江省公益性(No.2014C31127)资助项目.

Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones

Ruan Lingli^a, Fan Renjie^a, Liu Xinghai^a, Chen Jie^b, Weng Jianquan^a

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032;
b Bioassay Department, Zhejiang Branch of National Southern Pesticide Research Centre, Hangzhou 310023

Received:2014-10-31 Revised:2014-12-14 Published:2015-01-07
Supported by:
Project supported by the National Natural Science Foundation of China (No.30900959) and Public Project of Zhejiang Province (No.2014C31127).

1. Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones.PDF(581KB)

Abstract

In order to find novel biologically active pesticide lead compounds, twenty-one novel 3-[(5-benzylthio-1,3,4- oxadiazol-2-yl)methyl]benzo[d]thiazol(oxazol)-2(3H)-ones were synthesized by 2-benzothiazolinone/benzoxazolone as starting materials via substitution, hydrazine, cyclization and the last benzylation reaction. The structures of the title compounds were characterized by ¹H NMR, IR, EI-MS and elemental analysis. The preliminary bioassay results indicated that most of them showed moderate inhibition activity against Colletotrichum orbiculare, Botrytis cinerea and Rhizoctonia solani at 50 mg/L, and the inhibition rate of compound 5b against Botrytis cinerea and Rhizoctonia solani reached above 85%.

Key words: 2-benzothiazolinone/benzoxazolone, thioether, 1,3,4-oxadiazole, microwave synthesis, antifungal activity

Cite this article

Ruan Lingli, Fan Renjie, Liu Xinghai, Chen Jie, Weng Jianquan. Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones[J]. Chin. J. Org. Chem., 2015, 35(5): 1166-1172.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Strange, R. N.; Scott, P. R. Annu. Rev. Phytopathol. 2005, 43, 83.
[2] Li, B.; Liu, B.-P.; Yu, R.-R.; Lou, M.-M.; Wang, Y.-L.; Xie, G.-L.; Li, H.-Y.; Sun, G.-C. World J. Microbiol. Biotechnol. 2011, 27, 2305.
[3] Groth, D. E. Crop Prot. 2008, 27, 1125.
[4] Mahran, M. A.; Einassry, S. M.; Allam, S. R. Pharmazie 2003, 58, 527.
[5] Sidoova, E.; Loos, D.; Bujdakova, H. Molecules 1997, 2, 36.
[6] Wang, W.; Zhang, G.-P.; Song, B.-A.; Wang, H.; Jin, L.-H.; Hu, D.-Y.; Yang, S. Chin. J. Org. Chem. 2007, 27, 279 (in Chinese). (王伟, 张国平, 宋宝安, 汪华, 金林红, 胡德禹, 杨松, 有机化学, 2007, 27, 279.)
[7] Ganzer, M.; Dorfmeister, G.; Franke, W.; Johann, G.; Rees, R. DE 4117508, 1992 [Chem. Abstr. 1993, 118, 101946].
[8] David, P. C.; Roy, V. E.; Roy, T. H. J. Agric. Food Chem. 1981, 29, 640.
[9] Gewehr, M.; Dietz, J.; Grote, T.; Haden, E. WO 2009147205, 2009 [Chem. Abstr. 2010, 152, 113128].
[10] Michel, S. US 3922281, 1975 [Chem. Abstr. 1975, 82, 170877].
[11] Toyabe, K.; Shimizu, K.; Hirata, M.; Ikeda, T. JP 0217187, 1990 [Chem. Abstr. 1990, 113, 59158].
[12] Kraus, A.; Ishikawa, K. WO 2004095930, 2004 [Chem. Abstr. 2004, 141, 390414].
[13] Sidoova, E.; Loos, D.; Bujdakova, H.; Kallova, J. Molecules 1997, 2, 36.
[14] Koci, J.; Klimesova, V.; Waisser, K. Bioorg. Med. Chem. Lett. 2002, 12, 22.
[15] Hutchinson, I.; Chua, M. S.; Browne, H. L. J. Med. Chem. 2001, 4, 9.
[16] Huang, Q.-C.; Qian, X.-H.; Song, G.-H.; Cao, S. Pest Manage. Sci. 2003, 59, 933.
[17] Mo, Q.-J.; Duan, W.-G.; Li, X.-R.; Huang, D.-P.; Luo, D.-C. Chin. J. Org. Chem. 2011, 31, 1114 (in Chinese). (莫启进, 段文贵, 李行任, 黄丹平, 罗德城, 有机化学, 2011, 31, 1114.)
[18] Omar, F.-A.; Mahfouz, N.-M.; Rahman, M.-A. Eur. J. Med. Chem. 1996, 31, 819.
[19] Li, C.; Tan, Z.-L.; Li, X.-W.; Zhang, X. Chin. J. Org. Chem. 2005, 25, 5 (in Chinese). (李超, 覃章兰, 李秀文, 张欣, 有机化学, 2005, 25, 5.)
[20] Li, Q.-Z.; Song, B.-A.; Chen, J. Agrochemicals 2005, 44, 12 (in Chinese). (李黔柱, 宋宝安, 陈江, 农药, 2005, 44, 12.)
[21] Weng, J.-Q.; Liu, X.-H.; Huang, H.; Tan, C.-X.; Chen, J. Molecules 2012, 17, 989.
[22] Che, C.; Mao, S.-F.; Tan, Z.-H. Chin. Appl. Chem. 2002, 19, 8 (in Chinese). (车超, 毛淑芬, 覃兆海, 应用化学, 2002, 19, 8.)
[23] Elwahy, A. H.; Abbas, A. A. Tetrahedron 2000, 56, 885.
[24] Chen, H.-S.; Li, Z.-M.; Han, Y.- F. J. Agric. Food Chem. 2000, 48, 5312.
[25] Bao, X.-P.; Lin, X.-F.; Zhang, F.; Zhou, L.-B. Chin. J. Org. Chem. 2013, 33, 995 (in Chinese). (鲍小平, 林选福, 张峰, 邹林波, 有机化学, 2013, 33, 995.)
[26] Zhong, B.; Fan, Z.-J.; Li, Z.-M. Chin. Appl. Chem. 2003, 20, 7 (in Chinese). (钟斌, 范志金, 李正名, 应用化学, 2003, 20, 7.)
[27] De Sousa, G.; Nawaz, A.; Cravedi, J. P.; Rahmani, R. Toxicol. Sci. 2014, 141, 1.
[28] Chen, W.-B.; Jin, G.-Y. Acta Chim. Sinica 2001, 22, 1147 (in Chinese). (陈文彬, 金桂玉, 化学学报, 2001, 22, 1147.)
[29] Wang, L.; Asimakopoulos, A. G.; Moon, H. B.; Nakata, H.; Kannan, K. Environ. Sci. Technol. 2013, 47, 9.
[30] Amico, D. J.; Bollinger, F. G. Heterocycl. Chem. 1988, 25, 1183.
[31] Li, Y.-J.; Li, C.-Y.; Sun, S.-Q.; Zhou, X.-X. Acta Chim. Sinica 2012, 70, 2 (in Chinese). (李英俊, 李春燕, 孙淑琴, 周晓霞, 化学学报, 2012, 70, 2.)

新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮的合成及杀菌活性

Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lingna Wang, Xiaoqing Liu, Gang Lin, Hongying Jin, Minjun Jiao, Xuefen Liu, Shuping Luo. Photocatalytic Activation of C(sp³)—H Bonds to Form C—S Bonds Catalyzed by (Oxybis(4,1-phenylene))bis(phenylmethanone) [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2848-2854.
[2]	Feng Wang, Yu Chen, Hongyan Pei, Jing Zhang, Lixin Zhang. Design, Synthesis and Antifungal Activities of Novel 1,2,4-Oxadiazole Derivatives Containing Piperidine [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2826-2836.
[3]	Xiantao Ma, Xiaoyu Yan, Yingying Zhu, Shuanglin Niu, Yuxuan Wang, Chao Yuan. Water-Promoted Green Synthesis of Heteroaryl Thioether [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2136-2142.
[4]	Meng Li, Dongguo Xia, Yunxiao Wang, Xiang Cheng, Jiexiu Gong, Yao Chen, Xianhai Lü. Design, Synthesis and Antifungal Bioactivity Evaluation of Thiazole Benzoate Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 686-696.
[5]	Wei Chen, Simin Lei, Yuxin Lan, Haojian Xu, Pingbin Yu, Rui Zhang, Run Wu, Yang Chen. Design, Synthesis and Antifungal Activities of Novel Quinazolinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2164-2171.
[6]	Xiu Wang, Wengui Duan, Guishan Lin, Baoyu Li, Wenjing Zhang, Fuhou Lei. Synthesis, Antifungal Activity, Three-Dimensional Quantitative Structure-Activity Relationship and Molecular Docking Study of 4-Acyl-3-amino-1,2,4-triazole-thioether Derivatives Containing Natural Pinene Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 871-883.
[7]	Wei Wang, Furan Wu, Yidan Ma, Dan Xu, Gong Xu. Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 607-618.
[8]	Yucheng Cui, Meihua Chen, Guishan Lin, Wengui Duan, Qingmin Li, Renxuan Zou, Bo Cen. Synthesis, Antifungal Activity and Molecular Docking Study of 1,3,4-Thiadiazole-Urea Compounds Containing gem-Dimethylcyclopropane Ring Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3784-3797.
[9]	Hua Li, Jingxiang Pang, Huazheng Liu, Changyin Zhao, Song Li, Hengshan Wang, Xigong Liu. Sc(OTf)₃-Catalyzed 1,6-Conjugate Addition of Thiols to δ-CF₃-δ-aryl-disubstituted para-Quinone Methides: Efficient Construction of Diarylmethane Thioethers [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3134-3143.
[10]	Xingyue Wang, Changlin Xu, Hongyu Guan, Mi Lin, Peng Huang. Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3330-3334.
[11]	Weiwei Wang, Yu Zhao, Xinlei Liu, Jiazhen Jiang, Ming'an Wang. Synthesis and Antifungal Activity of 3-Aryl-7-methyl- 7-hydroxy-2-octen-6-olide [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2343-2353.
[12]	Chengfei Li, Bo Cen, Wengui Duan, Guishan Lin, Xiu Wang, Baoyu Li. Synthesis, Herbicidal Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-Methyl- 1,2,4-triazole-thioether Compounds Containing Natural Styrene Structure [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2485-2495.
[13]	Yanan Wu, Jianyu Du, Wenjuan Hao, Bo Jiang. Synthesis of Fused Pyridines via Microwave-Assisted [3+3] Cyclization [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1563-1571.
[14]	Hongbo Dong, Weiwei Wang, Yu Zhao, Xinlei Liu, Ming'an Wang. Synthesis and Antifungal Activity of 3,7-Dimethyl-7-hydroxy-2-octen-6-olide Analogues [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1646-1657.
[15]	Qi Wang, Boran Zhu, Guang Yang, Xiantao Ma, Qing Xu. Selective Synthesis of Unsymmetrical N-Heteroaryl Thioethers byBase-Free Direct Multi-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1193-1199.