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One‐pot synthesis of anilides, herbicidal activity and molecular docking study
Author(s) -
Sartori Suélen K,
Alvarenga Elson S,
Franco Cristiane A,
Ramos Danielle S,
Oliveira Denilson F
Publication year - 2018
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4855
Subject(s) - in silico , metolachlor , acetylation , docking (animal) , enzyme , histone deacetylase , biology , biochemistry , chemistry , histone , pesticide , agronomy , medicine , atrazine , nursing , gene
BACKGROUND In the context of the demand for more efficient herbicides, the aim of the present work was to synthesize anilides via simple methods, and evaluate their herbicidal activities through seed germination assays. In silico studies were carried out to identify the enzyme target sites in plants for the most active anilides. RESULTS A total of 18 anilides were prepared via one‐pot reaction in yields that varied from 36 to 98% through reactions of anilines with sorbic chloride and hexanoic anhydride. According to seed germination assays in three dicotyledonous and one monocotyledonous plant species, the most active anilides showed root and shoot growth inhibition superior to that of Dual ( S ‐metolachlor). In silico studies indicated that histone deacetylase was the probable enzyme target site in plants for these substances. The affinities of the most active anilides for the binding sites of this enzyme were equal to or higher than those calculated for its inhibitors. CONCLUSION Anilides 4d, 4e, 4 g, and 4 h are promising candidates for the development of novel herbicides. According to in silico studies, they inhibit histone deacetylase in plants, which can be exploited for the development of new weed control methods. © 2018 Society of Chemical Industry