Organophosphorus Compounds as Potential Fungicides. Part Ii. Aminoalkane-, Guanidinoalkane-, and Thioureidoalkane-Phosphonic Acids: Preparation, Spectroscopy, and Fungicidal Activity

Preparation of carbon‐14 labelled ampropylfos (1‐[14C]‐α‐aminopropanephosphonic acid)

“…7 This modified procedure was used in the present synthesis to give a product with 1-[ 14 C] labelling (Scheme 1) and with no detectable contaminants. The melting point found for the recrystallized product (275-2768C) was some 108C higher than that which we had previously observed for the unlabelled compound 5,7 and that reported by Tyka,…”

“…Of the various methods that are available for the preparation of a-aminoalkanephosphonic acids, 4 we have generally found it convenient 5 to use the one-pot procedure described by Oleksyszyn and Tyka,6 based on the interaction of triphenyl phosphite, an aliphatic aldehyde, and ethyl (or benzyl) carbamate in glacial acetic acid, followed by hydrolysis of the first-formed phosphonate ester with hydrochloric acid. The free aminophosphonic acid is then liberated by treatment with propylene oxide.…”

A theoretical study of medium effects on the structure of the glycine analogue aminomethylphosphonic acid

“…23,24 Aminophosphonic acids are also well-known for their herbicide and antifungal activity. [25][26][27][28][29] Recent work 30 has explored the analogy with phospholipids after a substitution with hydrophobic groups that confer an amphiphilic character and might enhance their coordinating and biological properties. Hence, not surprisingly, many efforts have been devoted to develop synthetic methods for these compounds.…”

Synthesis and Antiproliferative Activity of Novel α-Aminophosphonates

“…Generally, low mammalian toxicity of these compounds makes them attractive for use in agriculture and medicine. [6][7][8][9] Numerous of them possess antifungal, pesticidal, herbicidal and plant growth regulatory activity and are of particular interest for agrochemistry. [8][9][10][11][12] α-Aminophosphonates have also been found to act as enzyme inhibitors, haptens of catalytic antibiotics, inhibitors of serine hydrolases, uridine 5′-diphosphate (UDP)-galactopyranose mutase, human immunodeficiency virus (HIV) protease, and antitumor agents.…”

“…[6][7][8][9] Numerous of them possess antifungal, pesticidal, herbicidal and plant growth regulatory activity and are of particular interest for agrochemistry. [8][9][10][11][12] α-Aminophosphonates have also been found to act as enzyme inhibitors, haptens of catalytic antibiotics, inhibitors of serine hydrolases, uridine 5′-diphosphate (UDP)-galactopyranose mutase, human immunodeficiency virus (HIV) protease, and antitumor agents. [13][14][15][16][17][18][19][20] On the other hand, carbazole derivatives exhibit diverse biological activities such as antimalarial, antibacterial, anti-tuberculosis (TB), anti-HIV, anti-inflammatory, antihistaminic, and antitumor activities.…”