Design, synthesis and evaluation of novel cis - p -menthane type Schiff base compounds as effective herbicides

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

“…The monoterpene amine derivatives of α / β ‐pinene from turpentine have been extensively used in various fields due to their special properties and excellent bioactivities. cis‐ 1,8‐ p ‐Menthane‐diamine ( 8 , Scheme 1) is one of the most important products during turpentine processing, which can be efficiently synthesized using alkali hydrolysis of N , N '‐diacetyl‐ p ‐menthane‐1,8‐diamines ( 3 ) from α / β ‐pinene [18] . p‐ Menth‐3‐enylamine ( 5 ) is a novel monoterpene amine synthesized in very recent years, which can be prepared from N , N '‐diacetyl‐ p ‐menthane‐1,8‐diamines ( 8 ) by two steps as an acid‐catalyzed elimination and alkaline‐catalyzed hydrolysis [20] .…”

“…cis-1,8-p-Menthane-diamine (8, Scheme 1) is one of the most important products during turpentine processing, which can be efficiently synthesized using alkali hydrolysis of N,N'-diacetyl-p-menthane-1,8-diamines (3) from α/β-pinene. [18] p-Menth-3enylamine ( 5) is a novel monoterpene amine synthesized in very recent years, which can be prepared from N,N'-diacetyl-p-menthane-1,8-diamines (8) by two steps as an acid-catalyzed elimination and alkalinecatalyzed hydrolysis. [20] Our previous research has successfully synthesized a series of amine derivatives of cis-1,8-p-menthane-diamine and p-menth-3-enylamine and found the secondary amine derivatives (6a -6l, 9a-9i), such as N-(4-fluorobenzyl)-4-isopropyl-1-methylcyclohexane-3-enamine (6a), exhibited excellent herbicidal activities toward some noxious weeds.…”

“…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.…”

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

“…Among them, p -menth-3-enylamine and cis -1,8- p -menthane-diamine type Schiff base compounds showed herbicidal activities against ryegrass and barnyard grass superior to those of commercial herbicide glyphosate. 21–23 However, the imine group (C N) of Schiff base compounds is usually unstable in storage and herbicidal assays because it can be easily oxidized by air, hydrolyzed in an acidic environment, and subjected to transamination by nucleophiles. 24,25 Therefore, it is necessary to convert the Schiff bases into a more stable secondary amines using the reduction.…”

Synthesis of Anthranilic Diamide Derivatives Containing Moieties of Trifluoromethylpyridine and Hydrazone as Potential Anti-Viral Agents for Plants

“…13−15 This fragment is an ideal substructure for developing agrochemicals including antiviral agents, 16 insecticides, 17 bacteriostasis, 18 and herbicides. 19 In recent years, several series of novel derivatives containing hydrazone substructure have been designed and synthesized by introducing spiro-epoxy, 20,21 bipyrazole, 22,23 and trans-ferulic acid, 24 all of which have excellent anti-TMV activity. Fluorinated pesticides play an important role in the existing commercial agrochemicals.…”