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Crystals 2018, 8(2), 75; https://doi.org/10.3390/cryst8020075

Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide

1
Long Ping Branch, Graduate School of Hunan University, Changsha 410000, China
2
Hunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410000, China
3
College of Plant Protection, Hunan Agricultural University, Changsha 410000, China
4
Hunan Institute of Humanities, Science and Technology, Loudi 417000, China
*
Authors to whom correspondence should be addressed.
Received: 22 January 2018 / Revised: 29 January 2018 / Accepted: 30 January 2018 / Published: 1 February 2018
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Abstract

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. View Full-Text
Keywords: synthesis; crystal structure; benzamide; herbicide safeners; antifungal activity synthesis; crystal structure; benzamide; herbicide safeners; antifungal activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Zheng, W.-N.; Zhu, Z.-Y.; Deng, Y.-N.; Wu, Z.-C.; Zhou, Y.; Zhou, X.-M.; Bai, L.-Y.; Deng, X.-L. Synthesis, Crystal Structure, Herbicide Safening, and Antifungal Activity of N-(4,6-Dichloropyrimidine-2-Yl)Benzamide. Crystals 2018, 8, 75.

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