Design, synthesis, and herbicidal activity of sec-p-menthane-7-amine derivatives as botanical herbicides

Abstract

In this study, a series of novel p-menthane type secondary amines (sec-p-menthane-7-amine derivatives 3a–3y) were synthesized and then characterized by FTIR, ¹H NMR, ¹³C NMR, and HRMS. The post-emergence herbicidal activities of these amines against barnyard grass and rape were evaluated by the culture dish method. Most of the sec-p-menthane-7-amine derivatives showed excellent herbicidal activities equivalent to or even higher than either diuron or glyphosate. The alkyl-substituted derivatives were more active than the phenyl-substituted derivatives. The herbicidal activities of compounds 3p, 3r, 3u, and 3w against the root growth of barnyard grass were 404% higher, respectively, than those of glyphosate. The herbicidal activities of compounds 3q, 3v, 3w, and 3x against the root growth of rape were 561%, 494%, 491%, and 544% higher, respectively, than those of diuron, and 484%, 760%, 423%, and 665% higher respectively, than those of diuron against shoot growth of rape. In addition, compounds 3p, 3u, and 3v are almost harmless to rice, wheat, sorghum, maize, and peanuts at a concentration of 100 mg L⁻¹. Most of the compounds are nontoxic to HUVEC-C and BALB/c 3T3 cells. It is indicated that the title compounds could be utilized as botanical herbicides for future weed control.