Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide
The compound N-(4,6-dichloropyrimidine-2-yl)benzamide (C11H7Cl2N3O) was synthesized and the corresponding structure was confirmed by 1H NMR, 13C NMR, HRMS, IR, and single-crystal X-ray diffraction. The compound crystallized in a monoclinic system with space group P 21/c, where a = 14.9156(6), b = 16...
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MDPI AG
2018-02-01
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| Series: | Crystals |
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| Online Access: | http://www.mdpi.com/2073-4352/8/2/75 |
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| author | Wen-Na Zheng Zhe-Yuan Zhu Ya-Nan Deng Zhong-Chi Wu Yong Zhou Xiao-Mao Zhou Lian-Yang Bai Xi-Le Deng |
| author_facet | Wen-Na Zheng Zhe-Yuan Zhu Ya-Nan Deng Zhong-Chi Wu Yong Zhou Xiao-Mao Zhou Lian-Yang Bai Xi-Le Deng |
| author_sort | Wen-Na Zheng |
| collection | DOAJ |
| description | The compound N-(4,6-dichloropyrimidine-2-yl)benzamide (C11H7Cl2N3O) was synthesized and the corresponding structure was confirmed by 1H NMR, 13C NMR, HRMS, IR, and single-crystal X-ray diffraction. The compound crystallized in a monoclinic system with space group P 21/c, where a = 14.9156(6), b = 16.6291(8), c = 14.4740(6) Å, β = 95.160(2)°, V = 3575.5(3) Å3, Z = 12, Dc = 1.494 g∙cm−3, F(000) = 1632, μ(MoKa) = 3.182 mm−1, final R = 0.0870, and wR = 0.2331 with I > 2σ(I). The crystal structure was found to be stabilized by intermolecular hydrogen bonding interactions N–H···O and C–H···Cl. Furthermore, the results from biological assays indicated that the compound showed a similar protective effect on metolachlor injury in rice seedlings compared to fenclorim at a concentration of 4.0 mg∙L−1. Moreover, the compound exhibited an improved antifungal activity compared to pyrimethanil against S. sclerotiorum and F. oxysporum. Potentially, these results lay the foundation for the development of novel herbicide safeners and fungicides. |
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| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-14T05:22:18Z |
| publishDate | 2018-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-3208ec892c3f40e2b80a4e0b0be706172022-12-22T02:10:08ZengMDPI AGCrystals2073-43522018-02-01827510.3390/cryst8020075cryst8020075Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)BenzamideWen-Na Zheng0Zhe-Yuan Zhu1Ya-Nan Deng2Zhong-Chi Wu3Yong Zhou4Xiao-Mao Zhou5Lian-Yang Bai6Xi-Le Deng7Long Ping Branch, Graduate School of Hunan University, Changsha 410000, ChinaHunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410000, ChinaHunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410000, ChinaHunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410000, ChinaHunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410000, ChinaLong Ping Branch, Graduate School of Hunan University, Changsha 410000, ChinaLong Ping Branch, Graduate School of Hunan University, Changsha 410000, ChinaHunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410000, ChinaThe compound N-(4,6-dichloropyrimidine-2-yl)benzamide (C11H7Cl2N3O) was synthesized and the corresponding structure was confirmed by 1H NMR, 13C NMR, HRMS, IR, and single-crystal X-ray diffraction. The compound crystallized in a monoclinic system with space group P 21/c, where a = 14.9156(6), b = 16.6291(8), c = 14.4740(6) Å, β = 95.160(2)°, V = 3575.5(3) Å3, Z = 12, Dc = 1.494 g∙cm−3, F(000) = 1632, μ(MoKa) = 3.182 mm−1, final R = 0.0870, and wR = 0.2331 with I > 2σ(I). The crystal structure was found to be stabilized by intermolecular hydrogen bonding interactions N–H···O and C–H···Cl. Furthermore, the results from biological assays indicated that the compound showed a similar protective effect on metolachlor injury in rice seedlings compared to fenclorim at a concentration of 4.0 mg∙L−1. Moreover, the compound exhibited an improved antifungal activity compared to pyrimethanil against S. sclerotiorum and F. oxysporum. Potentially, these results lay the foundation for the development of novel herbicide safeners and fungicides.http://www.mdpi.com/2073-4352/8/2/75synthesiscrystal structurebenzamideherbicide safenersantifungal activity |
| spellingShingle | Wen-Na Zheng Zhe-Yuan Zhu Ya-Nan Deng Zhong-Chi Wu Yong Zhou Xiao-Mao Zhou Lian-Yang Bai Xi-Le Deng Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide Crystals synthesis crystal structure benzamide herbicide safeners antifungal activity |
| title | Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide |
| title_full | Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide |
| title_fullStr | Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide |
| title_full_unstemmed | Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide |
| title_short | Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide |
| title_sort | synthesis crystal structure herbicide safening and antifungal activity of n 4 6 dichloropyrimidine 2 yl benzamide |
| topic | synthesis crystal structure benzamide herbicide safeners antifungal activity |
| url | http://www.mdpi.com/2073-4352/8/2/75 |
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