Synthesis and Herbicidal Activities of p-Menth-3-en-1-amine and Its Schiff Base Derivatives

Abstract

p-Menth-3-en-1-amine, 4, and its Schiff base derivatives, 5a-l, were designed and synthesized. They were characterized by FT-IR, ESI-MS, HRMS, H NMR, andC NMR spectral analyses, and their pre-emergence herbicidal activities against ryegrass were evaluated. All of the compounds showed excellent herbicidal activity. The Schiff bases showed stronger herbicidal activities than the original amine 4. These compounds showed herbicidal activities comparable to that of glyphosate. The herbicidal activities of 5k and 5l against ryegrass shoot growth were 78.3 and 355.6% higher than that of glyphosate, respectively. Furthermore, the introduction of a chlorine or bromine atom into the Schiff base derivatives containing a furan or benzene ring was beneficial to increase the activity. However, the herbicidal activities were not clearly affected when the heteroatom of the five-membered heterocyclic Schiff base or the position of the substituent on pyridine Schiff base was altered.

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

“…Chemical herbicides play an important role in the development of agricultural production practice by providing a great convenience for weeds control as well as ensuring steady crop production 1,2 . However, the global application of herbicides has caused weed resistance and several environment problems, which requires the continuous discovery of new herbicidal molecules 3,4 . No new herbicide target has been found over the past 30 years, and most new herbicides based on current herbicidal targets have the trend of inducing rapid weed resistance 5–7 .…”

Synthesis, Herbicidal Activity and Toxicity Evaluation of Secondary Ammonium Salts from Turpentine Oil for Sustainable Weed Control

“…According to our previous study, p‐ menthane and p‐ menthene secondary amine compounds, including sec ‐ p ‐menth‐3‐enylamines, sec ‐ is ‐1,8‐ p ‐menthane‐diamines, and sec ‐ p ‐menthene‐7‐amines all possess low toxicity, potential herbicidal efficacy, and a broad spectrum against some noxious weeds [16–20] . However, the poor water‐solubility of these amine derivatives caused concerns in herbicidal applications, such as the overdose of herbicidal active substances and the excessive use of organic solvents and additives, which will have adverse effects on large‐scale application and sustainable development.…”

Biological Evaluation and Theoretical Study of Bi-dentate Ligand for Amoxicillin Derivative with Some Metal Ions

“…The significance of nitrogen-containing complexes in their application as high-efficiency biopharmaceuticals to many fungi is significant, for nitrogen possesses a high degree of consistency with metal in a base or neutral medium because it owns a single electronic pair that can be shared with another atom (1) .Schiff bases form a crucial class of the best and extensively used organic compounds and have a wide range of applications in numerous fields comprising analytical and biological fields (2). Schiff bases have distinction in medicinal and pharmaceutical arenas due to their expansive spectrum of biological activity such as antibacterial, antifungal (2,3), anticancer (4) and herbicidal activities (5). Amoxicillin (C 16 H 19 N 3 O 5 S) is a semi synthetic penicillin type antibiotic which has little effect toward gram-negative bacteria and high effect toward gram-positive bacteria (6).…”