Facile synthesis and nematicidal activity evaluation of thiophosphinyl amide [(Pz)2P(S)NHR] and thiophosphonyl diamide [(Pz)P(S)(NHR)2] (Pz = 1,3,5-trimethylpyrazole, R = biphenyl derivatives)?

RSC Advances Pub Date: 2021-11-10 DOI: 10.1039/D1RA06232H

Abstract

A series of thiophosphinyl amide [(Pz)2P(S)NHR] and thiophosphonyl diamide [PzP(S)(NHR)2] compounds, where Pz = 1,3,5-trimethylpyrazole and N(H)R = derivatives of 2-aminobiphenyl, were synthesized via a facile two-step process. Reaction of pyrazolyl substituted bromophosphine with 2-aminobiphenyl derivatives and further reaction with elemental sulphur affords the corresponding thiophosphinyl amide and thiophosphonyl diamide. The intermediate species was used without prior purification for reaction with sulphur to yield the target compounds. The nematicidal activity evaluation suggests that some compounds could manifest moderate nematicidal activity towards Meloidogyne incogita, which is higher than that of their amide analogue bixafen.

Graphical abstract: Facile synthesis and nematicidal activity evaluation of thiophosphinyl amide [(Pz)2P(S)NHR] and thiophosphonyl diamide [(Pz)P(S)(NHR)2] (Pz = 1,3,5-trimethylpyrazole, R = biphenyl derivatives)
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