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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #380121

Research Project: Novel Weed Management Tools from Natural Product-Based Discoveries

Location: Natural Products Utilization Research

Title: Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid

Author
item YU, CHEN-SHENG - Zhejiang University Of Technology
item WANG, QIAO - Zhejiang University Of Technology
item MIN, LI-JING - Huzhou University
item Bajsa Hirschel, Joanna
item HUA, XUE-WEN - Liaocheng University
item Cantrell, Charles
item DUKE, STEPHEN - Retired ARS Employee
item 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.
DOI: 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.