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Phytotoxicity of aminobisphosphonates targeting both δ 1 ‐pyrroline‐5‐carboxylate reductase and glutamine synthetase
Author(s) -
Giberti Samuele,
Bertazzini Michele,
Liboni Mattia,
Berlicki Łukasz,
Kafarski Paweł,
Forlani Giuseppe
Publication year - 2017
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4299
Subject(s) - proline , glutamine synthetase , glutamine , biochemistry , reductase , biology , amino acid , enzyme
BACKGROUND Dual‐target inhibitors may contribute to the management of herbicide‐resistant weeds and avoid or delay the selection of resistant biotypes. Some aminobisphosphonates inhibit the activity of both glutamine synthetase and δ 1 ‐pyrroline‐5‐carboxylate ( P5C ) reductase in vitro , but the relevance of the latter in vivo has yet to be proven. This study aimed at demonstrating that these compounds can also block proline synthesis in planta . RESULTS Two aminophosphonates, namely 3,5‐dichlorophenylamino‐methylenebisphosphonic acid and 3,5‐dibromophenylaminomethylenebis phosphonic acid ( Br 2 PAMBPA ), showed inverse effectiveness against the two partially purified target enzymes from rapeseed. The compounds showed equipotency in inhibiting the growth of rapeseed seedlings and cultured cells. The analysis of amino acid content in treated cells showed a strong reduction in glutamate and glutamate‐related amino acid pools, but a milder effect on free proline. In the case of Br 2 PAMBPA , toxic P5C levels accumulated in treated seedlings, proving that the inhibition of P5C reductase takes place in situ . CONCLUSIONS Phenyl‐substituted aminobisphosphonates may be regarded as true dual‐target inhibitors. Their use to develop new active principles for crop protection could consequently represent a tool to address the problem of target‐site resistance among weeds. © 2016 Society of Chemical Industry