New Synthesis and Fungicidal Activity of a Phosphinic Analogue of Glycine.

Abstract

New Synthesis and Fungicidal Activity of a Phosphinic Analogue of Glycine. -Compound (II) exhibits fungicidal activity towards Pyricularia oryzae, a pathogen of rice. -(ZHUKOV, Y. N.; VAVILOVA, N. A.; OSIPOVA, T. I.; KHURS, E. N.; DZHAVAKHIYA, V. G.; KHOMUTOV*, R. M.; Mendeleev Commun. 2004, 3, 93; Engelhardt Inst. Mol. Biol., Russ. Acad. Sci., Moscow 117984, Russia; Eng.) -M. Bohle 43-180

Design, Synthesis, and Evaluation of Novel Organophosphorus Inhibitors of Bacterial Ureases

“…Although the synthesis of 1-aminomethylphosphinic acid 9 (the analogue of glycine) has been intensively studied, − none of these methods were successful in our hands either because of multistep character and thus very low total yield of the process or because of toxic and expensive reagents required. Therefore, a recently described method was attempted and proved to be successful. In this procedure, aqueous solution of NaH 2 PO 2 and formaldoxime was added to hot methanolic solution of HCl, and the product was separated by ion-exchange chromatography (Scheme ).…”

Bis(aminomethyl)phosphinic Acid, a Highly Promising Scaffold for the Development of Bacterial Urease Inhibitors

“…The phosphorus component of the condensation and the precursor of the unsubstituted N−C−P portion, N-benzyloxycarbonylaminomethyl-H-phosphinic acid (28), was obtained by addition of sodium hypophosphite to a mixture of hydroxylamine hydrochloride and formaldehyde, followed by hydrolysis and Nprotection as described elsewhere. 38,39 As proven in our previous study, the phospha-Mannich condensation was not efficient for primary amines and produced a complex mixture of the desired product and byproducts. 40 Therefore, obtaining monosubstituted bis-(aminomethyl)phosphinic acid analogues demanded the use of the appropriate N-benzyl-N-alkylamines as secondary precursors.…”

“…A three-component phospha-Mannich type reaction of an N-protected aminomethyl- H -phosphinic acid, formaldehyde, and a secondary amine was used to build the additional (substituted) aminomethylene fragment of the target molecules 29 – 40 (Scheme ). The phosphorus component of the condensation and the precursor of the unsubstituted N–C–P portion, N -benzyloxycarbonylaminomethyl- H -phosphinic acid ( 28 ), was obtained by addition of sodium hypophosphite to a mixture of hydroxylamine hydrochloride and formaldehyde, followed by hydrolysis and N-protection as described elsewhere. , …”