European Journal of Chemistry

Efficient synthesis of azoxystrobin and its key intermediate using a newer DABCO-based catalyst

Crossmark


Main Article Content

Nilesh Dattatraya Dhande
Tushar Tulsidas Pansare
Uday Vasudev Baviskar
Hemant Prabhakar Narkhede

Abstract

A simple, convenient, and commercially feasible synthesis method has been developed for the synthesis of azoxystrobin and its intermediate using a DABCO-based catalyst. The methodology, which starts with coumaranone, uses a single catalyst for the two-step process, demonstrating high potential for industrial application. The catalyst synthesis and optimal catalyst concentration have been optimized to achieve maximum yield in the synthesis of the intermediate as well as technical azoxystrobin. The intermediate and final products, as well as the catalyst, were characterized by melting point, 1H NMR, 13C NMR, and high-resolution mass spectrometry. The HRMS analysis data supported the molecular formulae of the synthesized catalyst and product, showing the fragments m/z 143.1188 (M+H), C7H14N2O and 404.1262 (M+H), C22H17N3O5. The newer catalyst has the merits of being inexpensive, highly reactive, and environmentally friendly. The yield reached a high level, and this method can be considered a promising catalyst for the industrial-scale production of azoxystrobin and its key intermediate.


icon graph This Abstract was viewed 5 times | icon graph Article PDF downloaded 1 times

How to Cite
(1)
Dhande, N. D.; Pansare, T. T.; Baviskar, U. V.; Narkhede, H. P. Efficient Synthesis of Azoxystrobin and Its Key Intermediate Using a Newer DABCO-Based Catalyst. Eur. J. Chem. 2026, 17, 19-25.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. d'Hose, D.; Isenborghs, P.; Brusa, D.; Jordan, B. F.; Gallez, B. The Short-Term Exposure to SDHI Fungicides Boscalid and Bixafen Induces a Mitochondrial Dysfunction in Selective Human Cell Lines. Molecules 2021, 26 (19), 5842.
https://doi.org/10.3390/molecules26195842

[2]. Tsalidis, G. A. Human Health and Ecosystem Quality Benefits with Life Cycle Assessment Due to Fungicides Elimination in Agriculture. Sustainability 2022, 14 (2), 846.
https://doi.org/10.3390/su14020846

[3]. Chen, L.; Zhu, Y.; Fan, Z.; Guo, X.; Zhang, Z.; Xu, J.; Song, Y.; Yurievich, M. Y.; Belskaya, N. P.; Bakulev, V. A. Synthesis of 1,2,3-Thiadiazole and Thiazole-Based Strobilurins as Potent Fungicide Candidates. J. Agric. Food Chem. 2017, 65 (4), 745-751.
https://doi.org/10.1021/acs.jafc.6b05128

[4]. Bradshaw, M. J.; Boufford, D.; Braun, U.; Moparthi, S.; Jellings, K.; Maust, A.; Pandey, B.; Slack, S.; Pfister, D. H. An In-Depth Evaluation of Powdery Mildew Hosts Reveals One of the World's Most Common and Widespread Groups of Fungal Plant Pathogens. Plant Dis. 2024, 108 (3), 576-581.
https://doi.org/10.1094/PDIS-07-23-1471-RE

[5]. Chen, J.; Wang, W.; Chi, J.; Zhao, Y.; Deng, X.; Wang, L.; Chen, G. Methods for Preparing Azoxystrobin and Intermediate Thereof. U.S. Patent 10253001, 2019.

[6]. Jones, R. V. H.; Ewins, R. C.; Fleming, I. G. C.; McNeish, S.; Whitton, A. J. Process for the Preparation of Substituted Cyanophenoxy-Pyrimidinyloxy-Phenyl Acrylate Derivatives. WO Patent 9818767 A1, 1998.

[7]. Luo, Y.; Liu, Y.; Lu, Y.-G.; Yang, R.; Shi, G. Preparation Method of Fungicide Azoxystrobin Based on Suzuki Reaction. CN Patent 105566231 A, 2017.

[8]. Yue, C.; Peng, R.; Chen, B.; Pei, J. Preparation Method of Azoxystrobin. CN Patent 107698520 A, 2018.

[9]. Chen, B. A Method for Synthesizing Azoxystrobin. CN Patent 107235920 A, 2017.

[10]. Feng, Y. Preparation Method of Azoxystrobin for Stem and Leaf Spray, Seed Treatment and Soil Treatment. CN Patent 109320467 A, 2019.

[11]. Luo, J.; Yang, X.; Wang, Y.; Wang, Y. Synthesis of 2-[2-(4-Substituted-1,3,5-triazin-2-loxy)phenyl]-3,3-dimethoxypropanoate. Asian J. Chem. 2015, 27 (8), 2836-2840.
https://doi.org/10.14233/ajchem.2015.18227

[12]. Yang, X.; Zhang, Y.; Wang, Y.; Chen, T.; Luo, J. Synthesis of New Strobilurin Derivatives with Modified 1,3,5-Triazine Moiety. Asian J. Chem. 2013, 25 (16), 8897-8900.
https://doi.org/10.14233/ajchem.2013.14895

[13]. Liu, H.; Zhang, X.; Gao, Y.; Li, J.; Wang, H. Design, Synthesis, and Antifungal Activities of New β‐Methoxyacrylate Analogues. J. Chinese Chemical Soc 2012, 60 (1), 27-34.
https://doi.org/10.1002/jccs.201200295

[14]. Zhang, X.; Liu, H.; Gao, Y.; Wang, H.; Guo, B.; Li, J. Synthesis and Antifungal Activities of New Type β‐Methoxyacrylate‐Based Strobilurin Analogues. Chin. J. Chem. 2012, 30 (7), 1517-1524.
https://doi.org/10.1002/cjoc.201200101

[15]. Wang, J.; Zhao, H.; Hu, H.; Mei, Y.; Yang, L. Preparation of Azoxystrobin. CN Patent 114989099 A, 2022.

[16]. Xiao, H.; Xiao, L.; Feng, Y. Preparation Method of Azoxystrobin for Stem and Leaf Spray, Seed Treatment and Soil Treatment. CN Patent 109320467 A, 2018.

[17]. Li, B.; Xu, X.; Huang, X.; Liu, C.; Cheng, W.; Zhang, J.; Li, H.; Zhu, Z.; Wu, J.; Cao, J. Method for Synthesizing Azoxystrobin. CN Patent 109608405 A, 2019.

[18]. Li, H.; Guo, X.; Huang, X.; Cao, J.; Liu, C.; Xu, X.; Cheng, W.; Zhang, J.; Li, B.; Zhu, Z. Method for Synthesizing Abiotic to Prepare Azoxystrobin. CN Patent 109651262 A, 2019.

[19]. Lee, J. Y.; Kim, H. J.; Kim, H. H.; Choi, J. Y.; Jung, D. Y.; Choi, J. H.; Seo, Y. S.; Kang, M. G.; Kim, D. Y. Method for Preparing Azoxystrobin. KR Patent 2021023481 A, 2021.

[20]. Zhang, L.; Wei, Q.; Han, J.; Xiang, B.; Kang, Y.; Qiu, M.; Yang, J. Synthesis Method of Azoxystrobin Product. CN Patent 115043781 A, 2022.

[21]. David, A. J.; James, P. M.; Mark, R. S. Process for the Preparation of Azoxystrobin and its Intermediate. U.S. Patent 7084272, 2006.

[22]. Kini, P. V., Shelke, S. G. Process for preparation of azoxystrobin and intermediates thereof WO Patent 2020212919A1, 2020.

[23]. Yang, B.; Xue, W.; Yu, B.; Pang, H.; Yu, L.; Wang, Q.; Zhu, D. Development of a Trimethylamine-Catalyzed Novel Synthesis of Azoxystrobin. Org. Process Res. Dev. 2023, 27 (7), 1276-1282.
https://doi.org/10.1021/acs.oprd.3c00033

[24]. Beheshtia, Y. S.; Khorshidi, M.; Heravi, M. M.; Baghernejad, B. DABCO as an efficient catalyst for the synthesis of 3-cyano-2(1H)-pyridinones and their 2-imino analogues. Eur. J. Chem. 2010, 1 (3), 232-235.
https://doi.org/10.5155/eurjchem.1.3.232-235.112

[25]. Bita, B. 1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis. Eur. J. Chem. 2010, 1, 54-60.
https://doi.org/10.5155/eurjchem.1.1.54-60.2

[26]. Whitton, A. J., Boyd, E. C., & Vass, J. Processes for the preparation of azoxystrobin using dabco as a catalyst and novel intermediates used in the processes 20122012. U.S. Patent No. 8124761, 2012.

[27]. Gujral A.; Shah K. V.; Shah B. V., Kadam S.; Jani N. N.; Shinde R. Y. Process for the preparation of azoxystrobin WO Patent 2017060917A1, 2017.

[28]. Jones, J. D., Deboos, G. A., Wilkinson, P., Cox, B. G., & Fielden, J. M. Chemical process U.S. Patent No. 5847138 1998.

[29]. Ding, Y. L.; Dai, X. N.; Cai, Z. Y.; Deng, S. Q.; Han, D.; Yang, Y; Cao, C. Synthetic method of azoxystrobin and special intermediate for synthesis CN patent 102311392B, 2011.

[30]. Kini, P. V., Shelke, S. G. Process for the preparation of fungicidally active strobilurin compounds and intermediates thereof WO Patent 2020212928A1, 2020.

Supporting Agencies

Smt. Padamabai Kapurchandji Kotecha Mahila Mahavidyalaya, Bhusawal, District-Jalgaon, Maharashtra-425 201, India, Dadasaheb Devidas Namdeo Bhole College, Bhusawal, Dist.- Jalgaon, Maharashtra 425 201, India.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms
Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

License Terms

by-nc

Copyright © 2026 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).