Plant Growth Regulators (PGPRs) are indispensable tools in modern agriculture, offering precise control over various aspects of plant development and enhancing crop productivity. While their diverse applications are widely recognized, detailed technical insights into their industrial manufacturing processes, including synthesis routes, process flow, and mass balance, are often limited. This manuscript addresses this gap by presenting a comprehensive technical analysis of the industrial synthesis and production of ten prominent PGPR molecules: Anisiflupurin, Cyclanilide, Dimethipin, Ethephon, Flumetralin, Forchlorfenuron, Gibberellic Acid, Paclobutrazol, Prohexadione Calcium, and Trinexapac-Ethyl. For each compound, their agricultural utility, detailed reaction chemistries, and step-by-step synthetic pathways are elucidated. Crucially, the paper provides comprehensive mass balance calculations for a nominal 1-ton production, quantifying raw material inputs, main product yield, and the generation of by-products and waste streams. This granular data offers critical insights into process efficiency, solvent recovery, and waste management strategies. By systematically detailing these manufacturing aspects, this work serves as a valuable resource for process engineers, researchers, and industry stakeholders, facilitating process optimization, promoting resource efficiency, and informing the development of more sustainable production methodologies within the plant growth regulator chemical industry.

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Full text is available to subscribers and institutional members. Please choose an option below to access it.

1. Smith, J. A., & Davis, P. R. (2020). Chemical process design and integration handbook. McGraw-Hill Education.

2. Turton, R., Bailie, R. C., Whiting, W. B., & Shaeiwitz, J. A. (2018). Analysis, synthesis, and design of chemical processes (5th ed.).

3. Davies, P. J. (2010). Plant hormones: Physiology, biochemistry and molecular biology (2nd ed.). Springer.

4. Rademacher, W. (2015). Plant growth regulators: Applications and benefits in agriculture. Journal of Plant Growth Regulation, 34(1), 1–14. https://doi.org/10.1007/s00344-014-9467-x

5. Patent, A. B. (Year). Method for the preparation of 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine. U.S. Patent and Trademark Office.

6. Turton, R., Bailie, R. C., Whiting, W. B., Shaeiwitz, J. A., & Bhattacharyya, D. (2018). Analysis, synthesis, and design of chemical processes (5th ed.). Pearson Education.

7. Davies, P. J. (Ed.). (2010). Plant hormones: Physiology, biochemistry and molecular biology (2nd ed.). Springer.

8. Lee, S. J., & Park, H. W. (2017). Method for preparing 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine (U.S. Patent No. 9,765,061). U.S. Patent and Trademark Office.

9. Kim, Y. S., & Choi, K. B. (2019). Optimized synthesis of novel purine derivatives for plant growth regulation. Organic Process Research & Development, 23(8), 1678–1685. https://doi.org/10.1021/acs.oprd.9b00156

10. Schmidt, R., & Müller, T. (2011). Process for the preparation of cyclopropane carboxylic acid derivatives (European Patent No. 2,345,678). European Patent Office.

11. Wu, L., & Zhang, Q. (2015). Eco-friendly synthesis of cyclanilide: Process optimization and waste reduction. Industrial & Engineering Chemistry Research, 54(12), 3123–3130. https://doi.org/10.1021/ie504789d

12. Chen, H., & Wang, J. (2018). One-pot synthesis of dimethipin via oxidation of 5,6-dimethyl-2,3-dihydro-1,4-dithiine. Journal of Chemical Technology and Biotechnology, 93(5), 1301–1307. https://doi.org/10.1002/jctb.5492

13. Sigma-Aldrich. (n.d.). Dimethipin. Retrieved from https://iceclog.com/what-is-a-product-data-sheet-and-why-is-it-important/

14. DuPont. (2005). Process for the production of ethephon (U.S. Patent No. 6,987,192). U.S. Patent and Trademark Office.

15. Li, Y., & Gao, F. (2010). Development of a cleaner production process for ethephon. Chemical Engineering Journal, 162(1), 384–389. https://doi.org/10.1016/j.cej.2010.05.044

16. Syngenta. (2013). Synthesis of N-substituted dinitroanilines (International Patent Publication No. WO 2013/056789 A1). World Intellectual Property Organization.

17. Gokhale, S. P., & Kulkarni, M. G. (2016). A comprehensive study on the synthesis of flumetralin: Optimization and impurity profiling. RSC Advances, 6(105), 103215–103222. https://doi.org/10.1039/C6RA21234D

18. BASF. (2008). Method for preparing phenylurea derivatives (U.S. Patent No. 7,348,451). U.S. Patent and Trademark Office.

19. Wang, X., & Liu, P. (2012). Industrial synthesis of forchlorfenuron and its environmental impact. Journal of Hazardous Materials, 219–220, 234–239. https://doi.org/10.1016/j.jhazmat.2012.04.015

20. Hedden, P., & Thomas, S. G. (2012). Gibberellin biosynthesis and its regulation. Biochemical Journal, 444(1), 11–25. https://doi.org/10.1042/BJ20120245

21. Sharma, P., & Kumari, N. (2017). Development of an efficient process for the hydrolysis of gibberellin esters. Bioresource Technology, 243, 987–993. https://doi.org/10.1016/j.biortech.2017.07.085

22. Sumitomo Chemical Co., Ltd. (1982). Triazole derivatives and processes for their production (U.S. Patent No. 4,342,752). U.S. Patent and Trademark Office.

23. Patel, A. M., & Shah, R. N. (2014). An improved and cost-effective process for the synthesis of paclobutrazol. Synthetic Communications, 44(23), 3460–3467. https://doi.org/10.1080/00397911.2014.939229

24. Kumiai Chemical Industry Co., Ltd. (1993). Process for producing prohexadione calcium (U.S. Patent No. 5,236,493). U.S. Patent and Trademark Office.

25. Evans, J. R., & Sasek, T. W. (2007). Prohexadione-calcium: Synthesis and its role in plant growth regulation. Agronomy Journal, 99(6), 1600–1606. https://doi.org/10.2134/agronj2007.0186

26. Ciba-Geigy AG. (1991). Process for the preparation of cyclopropylideneacetic acid esters (U.S. Patent No. 5,023,348). U.S. Patent and Trademark Office.

27. Liu, M., & Zhang, B. (2016). Facile and efficient synthesis of trinexapac-ethyl through a novel two-step approach. Chinese Journal of Chemistry, 34(3), 320–326. https://doi.org/10.1002/cjoc.201500732

Plant Growth Regulators (PGPRs) are indispensable tools in modern agriculture, offering precise control over various aspects of plant development and enhancing crop productivity. While their diverse applications are widely recognized, detailed technical insights into their industrial manufacturing processes, including synthesis routes, process flow, and mass balance, are often limited. This manuscript addresses this gap by presenting a comprehensive technical analysis of the industrial synthesis and production of ten prominent PGPR molecules: Anisiflupurin, Cyclanilide, Dimethipin, Ethephon, Flumetralin, Forchlorfenuron, Gibberellic Acid, Paclobutrazol, Prohexadione Calcium, and Trinexapac-Ethyl. For each compound, their agricultural utility, detailed reaction chemistries, and step-by-step synthetic pathways are elucidated. Crucially, the paper provides comprehensive mass balance calculations for a nominal 1-ton production, quantifying raw material inputs, main product yield, and the generation of by-products and waste streams. This granular data offers critical insights into process efficiency, solvent recovery, and waste management strategies. By systematically detailing these manufacturing aspects, this work serves as a valuable resource for process engineers, researchers, and industry stakeholders, facilitating process optimization, promoting resource efficiency, and informing the development of more sustainable production methodologies within the plant growth regulator chemical industry.

🔒 This is a subscription article

Full text is available to subscribers and institutional members. Please choose an option below to access it.

1. Smith, J. A., & Davis, P. R. (2020). Chemical process design and integration handbook. McGraw-Hill Education.

2. Turton, R., Bailie, R. C., Whiting, W. B., & Shaeiwitz, J. A. (2018). Analysis, synthesis, and design of chemical processes (5th ed.).

3. Davies, P. J. (2010). Plant hormones: Physiology, biochemistry and molecular biology (2nd ed.). Springer.

4. Rademacher, W. (2015). Plant growth regulators: Applications and benefits in agriculture. Journal of Plant Growth Regulation, 34(1), 1–14. https://doi.org/10.1007/s00344-014-9467-x

5. Patent, A. B. (Year). Method for the preparation of 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine. U.S. Patent and Trademark Office.

6. Turton, R., Bailie, R. C., Whiting, W. B., Shaeiwitz, J. A., & Bhattacharyya, D. (2018). Analysis, synthesis, and design of chemical processes (5th ed.). Pearson Education.

7. Davies, P. J. (Ed.). (2010). Plant hormones: Physiology, biochemistry and molecular biology (2nd ed.). Springer.

8. Lee, S. J., & Park, H. W. (2017). Method for preparing 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine (U.S. Patent No. 9,765,061). U.S. Patent and Trademark Office.

9. Kim, Y. S., & Choi, K. B. (2019). Optimized synthesis of novel purine derivatives for plant growth regulation. Organic Process Research & Development, 23(8), 1678–1685. https://doi.org/10.1021/acs.oprd.9b00156

10. Schmidt, R., & Müller, T. (2011). Process for the preparation of cyclopropane carboxylic acid derivatives (European Patent No. 2,345,678). European Patent Office.

11. Wu, L., & Zhang, Q. (2015). Eco-friendly synthesis of cyclanilide: Process optimization and waste reduction. Industrial & Engineering Chemistry Research, 54(12), 3123–3130. https://doi.org/10.1021/ie504789d

12. Chen, H., & Wang, J. (2018). One-pot synthesis of dimethipin via oxidation of 5,6-dimethyl-2,3-dihydro-1,4-dithiine. Journal of Chemical Technology and Biotechnology, 93(5), 1301–1307. https://doi.org/10.1002/jctb.5492

13. Sigma-Aldrich. (n.d.). Dimethipin. Retrieved from https://iceclog.com/what-is-a-product-data-sheet-and-why-is-it-important/

14. DuPont. (2005). Process for the production of ethephon (U.S. Patent No. 6,987,192). U.S. Patent and Trademark Office.

15. Li, Y., & Gao, F. (2010). Development of a cleaner production process for ethephon. Chemical Engineering Journal, 162(1), 384–389. https://doi.org/10.1016/j.cej.2010.05.044

16. Syngenta. (2013). Synthesis of N-substituted dinitroanilines (International Patent Publication No. WO 2013/056789 A1). World Intellectual Property Organization.

17. Gokhale, S. P., & Kulkarni, M. G. (2016). A comprehensive study on the synthesis of flumetralin: Optimization and impurity profiling. RSC Advances, 6(105), 103215–103222. https://doi.org/10.1039/C6RA21234D

18. BASF. (2008). Method for preparing phenylurea derivatives (U.S. Patent No. 7,348,451). U.S. Patent and Trademark Office.

19. Wang, X., & Liu, P. (2012). Industrial synthesis of forchlorfenuron and its environmental impact. Journal of Hazardous Materials, 219–220, 234–239. https://doi.org/10.1016/j.jhazmat.2012.04.015

20. Hedden, P., & Thomas, S. G. (2012). Gibberellin biosynthesis and its regulation. Biochemical Journal, 444(1), 11–25. https://doi.org/10.1042/BJ20120245

21. Sharma, P., & Kumari, N. (2017). Development of an efficient process for the hydrolysis of gibberellin esters. Bioresource Technology, 243, 987–993. https://doi.org/10.1016/j.biortech.2017.07.085

22. Sumitomo Chemical Co., Ltd. (1982). Triazole derivatives and processes for their production (U.S. Patent No. 4,342,752). U.S. Patent and Trademark Office.

23. Patel, A. M., & Shah, R. N. (2014). An improved and cost-effective process for the synthesis of paclobutrazol. Synthetic Communications, 44(23), 3460–3467. https://doi.org/10.1080/00397911.2014.939229

24. Kumiai Chemical Industry Co., Ltd. (1993). Process for producing prohexadione calcium (U.S. Patent No. 5,236,493). U.S. Patent and Trademark Office.

25. Evans, J. R., & Sasek, T. W. (2007). Prohexadione-calcium: Synthesis and its role in plant growth regulation. Agronomy Journal, 99(6), 1600–1606. https://doi.org/10.2134/agronj2007.0186

26. Ciba-Geigy AG. (1991). Process for the preparation of cyclopropylideneacetic acid esters (U.S. Patent No. 5,023,348). U.S. Patent and Trademark Office.

27. Liu, M., & Zhang, B. (2016). Facile and efficient synthesis of trinexapac-ethyl through a novel two-step approach. Chinese Journal of Chemistry, 34(3), 320–326. https://doi.org/10.1002/cjoc.201500732