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

Abstract

Abstract:The compound N-(4,6-dichloropyrimidine-2-yl)benzamide (C 11 H 7 Cl 2 N 3 O) was synthesized and the corresponding structure was confirmed by 1 H NMR, 13 C NMR, HRMS, IR, and single-crystal X-ray diffraction. The compound crystallized in a monoclinic system with space group P 2 1 /c, where a = 14.9156(6), b = 16.6291(8), c = 14.4740(6) Å, β = 95.160(2) • , V = 3575.5(3) Å 3 , 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.

The Effect of Salicylic Acid and 20 Substituted Molecules on Alleviating Metolachlor Herbicide Injury in Rice (Oryza sativa)

“…The phytotoxicity of compounds a-u on rice and the herbicide safening activities of SA and 20 substituted SA compounds (a-u) were evaluated by agar culture methodology under laboratory conditions according to a previous method [42]. A 12 g agar strip was added to 3 L of deionized water at 100 • C. The mixture was then constantly stirred over heat until the agar strip had completely dissolved.…”

“…Agar media were as follows: 0.25 µM M; 8 mg L −1 of compounds a-u; 8 mg L −1 F with 0.25 µM M; 8 mg L −1 compounds a-u with 0.25 µM M; and no additional compounds. Seedlings were collected and planted according to previous methods [41,42]. Fifty seedlings were added to each plastic box and incubated for 14 h at 30 • C under a grow light (intensity 110-130 µE m -2 s −1 ), followed by a 10 h dark photoperiod at 25 • C. After 7 days, indexes related to herbicide safener activity (plant height, root length, and fresh weight) of the seedlings in each box were measured.…”

“…The structure-activity relationship (SAR) of these compounds was also studied. These were tested against a metolachlor (M) herbicide using agar culture methodology, as reported in our previous articles [41,42]. Fenclorim (F), a commercial herbicide safener, was used as the positive control [43].…”

Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

“…The great number of heterocyclic compounds is used in medicine as drugs for miscellaneous diseases. The drugs that have the heterocyclic core in their frame have some specific activity such as antifungal activity, anti‐inflammation, antibacterial, antioxidants, anticonvulsant, antiallergic, herbicidal activity, and and anticancer …”

“…The great number of heterocyclic compounds is used in medicine as drugs for miscellaneous diseases. The drugs that have the heterocyclic core in their frame have some specific activity such as antifungal activity, 46 anti-inflammation, 47 antibacterial, 48 antioxidants, 49 anticonvulsant, 50 antiallergic, 51 herbicidal activity, 52 and and anticancer. 49 Although a number of studies have been reported on bioactivity of ferrocene and xanthone individually, 1-6,44,53-55 based on our knowledge, there is still no report on anticancer polymers bearing ferrocene and xanthone in the main chain.…”