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

Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibite...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2021-06, Vol.69 (23), p.6423-6430
Main Authors: Yu, Chen-Sheng, Wang, Qiao, Bajsa-Hirschel, Joanna, Cantrell, Charles L, Duke, Stephen O, Liu, Xing-Hai
Format: Article
Language:English
Subjects:
Agricultural and Environmental Chemistry
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Summary:Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)­oxy)­nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure–activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.0c07538