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.
Highlights
Herbicides are frequently used for the control of weeds both in an effort to ensure the adequate production of food crops and to meet increased production requirements
[4,31], we have evaluated the antifungal activity of serve as fungicides [4,31], we have evaluated the antifungal activity of Compound 1
Fenclorim exhibited fungicidal activities, with an IC50 of 18.11 mg·L−1 against Sclerotinia sclerotiorum, 27.33 mg·L−1 against Fusarium oxysporum, 39.53 mg·L−1 against Fusarium graminearum, and 28.46 mg·L−1 against Thanatephorus cucumeris. These results indicated that fenclorim could be further used as a lead compound to develop novel fungicides
Summary
Herbicides are frequently used for the control of weeds both in an effort to ensure the adequate production of food crops and to meet increased production requirements. In order to protect crops from potential injuries caused by herbicides, the use of herbicide safeners is the most straightforward and cost-effective method [8,9]. In 1970, the first commercialized herbicide safener (1,8-naphthalic anhydride, NA) was reported by Hoffman et al and was designed to protect corn from thiocarbamate herbicide injury [11,12,13]. Reports onorfenclorim or itscan derivatives beliterature found inthat the offer guidance to further identify novel herbicide safeners. Andand even herbicide safener activities [30] For this reason and to further fungicide [28],. (1) was synthesized via insertion of an amide group the chlorinated substituted pyrimidine ring and the phenyl ring of fenclorim The herbicide safener activity protect rice rice from from chloroacetanilide herbicide metolachlor injury was tested.
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