Location: Natural Products Utilization ResearchTitle: Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
|YU, CHEN-SHENG - Zhejiang University Of Technology|
|WANG, QIAO - Zhejiang University Of Technology|
|MIN, LI-JING - Huzhou University|
|Bajsa Hirschel, Joanna|
|HUA, XUE-WEN - Liaocheng University|
|DUKE, STEPHEN - Retired ARS Employee|
|LIU, XING-HAI - Zhejiang University Of Technology|
Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/22/2021
Publication Date: 6/4/2021
Citation: Yu, C., Wang, Q., Min, L., Bajsa Hirschel, J.N., Hua, X., Cantrell, C.L., Duke, S., Liu, X. 2021. Synthesis, Crystal Structure and Herbicidal Activity of Novel N-(aryloxy)-2-chloronicotinamides Derived from the Natural Product Niacin. Journal of Agricultural and Food Chemistry. https://doi.org/10.1021/acs.jafc.0c07538.
Interpretive Summary: Nicotinic acid (niacin or vitamin B3) is a natural product first extracted from tobacco (Nicotiana spp.) and its derivatives can be found in many plants, such as tobacco, Areca catechu, seeds of Ricinus communis, and seed coats of cereal grains. Niacin contains an important pyridine motif and derivatives of such have been used in the synthetic design of agrochemicals, with many pesticides containing this pyridine motif such as the herbicide nicosulfuron. Fifteen niacin derivatives were synthesized in the aim of uncovering a new leading compound with phytotoxic activity. Some of the compounds displayed excellent herbicidal activity against both bentgrass and duckweed.
Technical Abstract: Nicotinic acid is a natural product, which is widely found in plants and animals. In order to discover novel natural product derivative herbicides, a series of N-(aryloxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(aryloxy)-2-chloronicotinamides exhibited excellent herbicidal activity against bentgrass at 100 µM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against duckweed, with an IC50 value of 7.8 µM, whereas the commercial herbicide clomazone had a value of 125 µM. The structure-activity relationships reported in this paper could be used for development of new herbicides against monocotyledonous weeds.