Synthesis, herbicidal activity and in silico analysis of novel pyrido[2,3-d]pyrimidine compounds

Authors: LIANG, WEI - Zhejiang University Of Technology; WANG, QIAO - Zhejiang University Of Technology; MIN, LI-JING - Huzhou University; HAN, LIANG - Zhejiang University Of Technology; Cantrell, Charles; Bajsa-Hirschel, Joanna; DUKE, STEPHEN - University Of Mississippi; YE, PENG - Shanghai Souguo Science & Technology Co Ltd; LIU, XING-HAI - Zhejiang University Of Technology

Submitted to: Molecules
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/29/2023
Publication Date: 10/31/2023
Citation: Liang, W., Wang, Q., Min, L., Han, L., Cantrell, C.L., Bajsa Hirschel, J.N., Duke, S.0., Ye, P., Liu, X. 2023. Synthesis, herbicidal activity and in silico analysis of novel pyrido[2,3-d]pyrimidine compounds. Molecules. https://doi.org/10.3390/molecules28217363.
DOI: https://doi.org/10.3390/molecules28217363

Interpretive Summary: Heterocyclic molecules are important scaffolds for natural and synthetic compounds due to their wide range of biological activities. Pyrimidines are an important class of heterocyclic molecules, which have received extensive attention in the field of agricultural and medicinal chemistry, due to their outstanding biological activities, such as insecticidal, fungicidal and herbicidal activity. In order to discover lead compounds with high herbicidal activity, a series of novel compounds were designed and synthesized using 2-chloronicotinic acid as the starting material. The results showed that most of the target compounds have no obvious inhibitory effect on lettuce; however, most of the compounds exhibited good activity against bentgrass. Among them, the most active compound was as active as the positive control, the commercial herbicide clomazone.

Technical Abstract: In order to discover lead compounds with high herbicidal activity, a series of novel pyrido[2,3-d] pyrimidine compounds were designed and synthesized using 2-chloronicotinic acid as the starting material. Their structures were characterized by proton nuclear magnetic resonance spectroscopy (1HNMR) and high-resolution mass spectroscopy (HRMS), and the herbicidal activity against dicotyledonous lettuce and monocotyledon bentgrass was tested. The results showed that most of the target compounds have no obvious inhibitory effect on lettuce at 1 mM. However, most of the compounds exhibited good activity against bentgrass at 1 mM. Among them, the most active compound, 3-methyl-1-(2,3,4-trifluorophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dionewas as active as the positive control, the commercial herbicide clomazone.