Crystal structure and Hirshfeld surface analysis of the fungicide metconazole
Metconazole is a systemic triazole fungicide that inhibits the ergosterol biosynthesis pathway. It is widely used in agriculture to control fungal infections, including rusts, fusarium and septoria diseases. The molecular structure is a three-ring system, namely, 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1...
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International Union of Crystallography
2025-05-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S205698902500310X |
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| author | Thaluru M. Mohan Kumar Chaluvarangaiah Sowbhagya Hemmige S. Yathirajan Sean Parkin |
| author_facet | Thaluru M. Mohan Kumar Chaluvarangaiah Sowbhagya Hemmige S. Yathirajan Sean Parkin |
| author_sort | Thaluru M. Mohan Kumar |
| collection | DOAJ |
| description | Metconazole is a systemic triazole fungicide that inhibits the ergosterol biosynthesis pathway. It is widely used in agriculture to control fungal infections, including rusts, fusarium and septoria diseases. The molecular structure is a three-ring system, namely, 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol, C17H22ClN3O, consisting of a cyclopentan-1-ol with 1,2,4-triazol-1-ylmethyl, gem-dimethyl and 4-chlorobenzyl groups attached at the 1-, 2- and 5-positions of the cyclopentanol ring. It has two stereocentres (cyclopentanol positions 1 and 5) leading to four stereoisomers, with the (1S,5R) form being the most bioactive. Despite its agricultural significance, detailed crystallographic data remain scarce. This study reports the crystal structure and Hirshfeld surface analysis of racemic cis-metconazole [(1S,5R)/(1R,5S)], determined in the monoclinic space group P21/c with two independent molecules in the asymmetric unit (Z′ = 2). Both exhibit similar conformations, with minor differences in the cyclopentanol ring puckering and the torsion angles between the three rings. The crystal packing consists of 21-screw-related hydrogen-bonded chains parallel to the b axis, with additional weak C—H...N and C—H...Cl contacts linking adjacent molecules. Hirshfeld surface analysis indicates that intermolecular interactions are dominated by contacts involving hydrogen (96.1 and 96.7% for the two molecules). |
| format | Article |
| id | doaj-art-9341cf7453ad40be9f68fdb1f0b60afe |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-9341cf7453ad40be9f68fdb1f0b60afe2025-08-20T03:52:10ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-05-0181538538810.1107/S205698902500310Xvm2312Crystal structure and Hirshfeld surface analysis of the fungicide metconazoleThaluru M. Mohan Kumar0Chaluvarangaiah Sowbhagya1Hemmige S. Yathirajan2Sean Parkin3Department of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru 560 035, IndiaDepartment of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru 560 035, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, IndiaDepartment of Chemistry, University of Kentucky, Lexington, KY 40506-0055, USAMetconazole is a systemic triazole fungicide that inhibits the ergosterol biosynthesis pathway. It is widely used in agriculture to control fungal infections, including rusts, fusarium and septoria diseases. The molecular structure is a three-ring system, namely, 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol, C17H22ClN3O, consisting of a cyclopentan-1-ol with 1,2,4-triazol-1-ylmethyl, gem-dimethyl and 4-chlorobenzyl groups attached at the 1-, 2- and 5-positions of the cyclopentanol ring. It has two stereocentres (cyclopentanol positions 1 and 5) leading to four stereoisomers, with the (1S,5R) form being the most bioactive. Despite its agricultural significance, detailed crystallographic data remain scarce. This study reports the crystal structure and Hirshfeld surface analysis of racemic cis-metconazole [(1S,5R)/(1R,5S)], determined in the monoclinic space group P21/c with two independent molecules in the asymmetric unit (Z′ = 2). Both exhibit similar conformations, with minor differences in the cyclopentanol ring puckering and the torsion angles between the three rings. The crystal packing consists of 21-screw-related hydrogen-bonded chains parallel to the b axis, with additional weak C—H...N and C—H...Cl contacts linking adjacent molecules. Hirshfeld surface analysis indicates that intermolecular interactions are dominated by contacts involving hydrogen (96.1 and 96.7% for the two molecules).https://journals.iucr.org/paper?S205698902500310Xmetconazolefungicideconazoletriazolecrystal structurehirshfeld surface analysis |
| spellingShingle | Thaluru M. Mohan Kumar Chaluvarangaiah Sowbhagya Hemmige S. Yathirajan Sean Parkin Crystal structure and Hirshfeld surface analysis of the fungicide metconazole Acta Crystallographica Section E: Crystallographic Communications metconazole fungicide conazole triazole crystal structure hirshfeld surface analysis |
| title | Crystal structure and Hirshfeld surface analysis of the fungicide metconazole |
| title_full | Crystal structure and Hirshfeld surface analysis of the fungicide metconazole |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of the fungicide metconazole |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of the fungicide metconazole |
| title_short | Crystal structure and Hirshfeld surface analysis of the fungicide metconazole |
| title_sort | crystal structure and hirshfeld surface analysis of the fungicide metconazole |
| topic | metconazole fungicide conazole triazole crystal structure hirshfeld surface analysis |
| url | https://journals.iucr.org/paper?S205698902500310X |
| work_keys_str_mv | AT thalurummohankumar crystalstructureandhirshfeldsurfaceanalysisofthefungicidemetconazole AT chaluvarangaiahsowbhagya crystalstructureandhirshfeldsurfaceanalysisofthefungicidemetconazole AT hemmigesyathirajan crystalstructureandhirshfeldsurfaceanalysisofthefungicidemetconazole AT seanparkin crystalstructureandhirshfeldsurfaceanalysisofthefungicidemetconazole |