Synthesis and Herbicidal Activity of O‐(2,6‐Bis(4,6‐dimethoxypyrimidin‐2‐yloxy) benzoyl)oxime 3‐Trifluoromethylacetophenone

Abstract

O‐(2,6‐bis(4,6‐dimethoxypyrimidin‐2‐yloxy)benzoyl)oxime 3‐trifluoromethylacetophenone (HB‐002) was synthesized as potential acetolactate synthetase (ALS)‐inhibiting herbicides. HB‐002 was characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, high resolution mass spectrometer (HRMS), and X‐ray single‐crystal diffraction. The herbicidal activities of HB‐002 against four weeds were studied in greenhouse. The results show that the control effects of HB‐002 on Eclipta prostrata L. and Cyperus difformis are very weak. However, HB‐002 exhibits higher herbicidal activity against Leptochloa chinensis (L.) Nees than that of Pyribenzoxim. HB‐002 also shows certain control effect on Echinochloa oryzoides (Ard.) Flritsch. Molecular docking simulation was performed to study the binding affinity and probable binding modes of HB‐002 with ALS. In the binding mode, the trifluoromethyl group of HB‐002 forms two halogen bonds (fluorine) with ALS, contributing to the lower binding free energy of HB‐002 (‐45.336 kcal/mol) as compared to Pyribenzoxim (‐40.1286 kcal/mol) and m‐trifluoromethyl Pyribenzoxim (‐44.451 kcal/mol). The present work suggests that HB‐002 may serve as a new candidate for potential herbicides.

Synthesis, antiproliferative activity, 3D‐QSAR, and molecular docking studies of novel L‐carvone‐derived pyrimidine‐urea compounds

“…Pyrimidine is a nitrogen-containing heterocyclic ring that can be easily synthesized from beta-dicarbonyl compounds, and its derivatives have been focused on because of their extensive biological activities, such as antibacterial [20], herbicidal [21][22][23], antitumor [24,25], and insecticidal activities [26]. In addition, the urea motif exhibited a more potent capacity in the formation of hydrogen bonds than the amide group and served as a desirable bridge for linking double chemical substructures.…”

Synthesis, Herbicidal Activity against Barnyard Grass, and Photolytic Behavior of Aryl 2,6-Dipyrimidinoxybenzoates

“…21,25,26 also exhibited good herbicidal performance. 22,23 Previously, we synthesized diaryl oxime esters of bispyribac acid bearing a pyridine moiety, exhibiting excellent herbicidal activity in greenhouse and field conditions. These compounds function as pro-herbicide activated via both enzyme-catalyzed hydrolysis and photolysis.…”

“…Methyl esterification of 2-(pyrimidin-2-yloxy)­benzoic acid minimally impacts the activity of PYB herbicides. However, when esterified with other fatty alcohols or phenol, there is a dramatic decrease in its herbicidal activity. ,,, Moreover, pyribenzoxim, an oxime esterification product of bispyribac acid, has proven successful as a light-activated herbicide, altering some characteristics of bispyribac-sodium, such as application period and safety. ,, Other oxime esters have also exhibited good herbicidal performance. , Previously, we synthesized diaryl oxime esters of bispyribac acid bearing a pyridine moiety, exhibiting excellent herbicidal activity in greenhouse and field conditions. These compounds function as pro-herbicide activated via both enzyme-catalyzed hydrolysis and photolysis .…”

Synthesis, antiproliferative activity, 3D-QSAR and molecular docking studies of novel L-carvone-derived pyrimidine-urea compounds

“…Pyrimidine is a nitrogen-containing hetero-aromatic ring that can be easily synthesized from betadicarbonyl compounds, and its derivatives had been focused because of their extensive biological activities, such as antibacterial [20], herbicidal [21][22][23], antitumor [24,25], and insecticidal activities [26]. For example, Dasatinib containing pyrimidine structure has been developed into a commercial anticancer drug (Fig.…”