New Alkylitaconic Acid Derivatives from Nodulisporium sp. A21 and Their Auxin Herbicidal Activities on Weed Seeds.

Five alkylitaconic acid (AA) derivatives, including two novel compounds, epideoxysporothric acid (2) and sporochartine F (5), and three known compounds, deoxysporothric acid (1), deoxyisosporothric acid (3), and 1-undecen-2,3-dicarboxylic acid (4), were obtained from the fermentation culture of the endophytic fungus Nodulisporium sp. A21. The auxin herbicidal activities of compounds 1-4 against weed seeds were investigated under laboratory conditions. In general, the tested compounds displayed radicle growth promoting activity at low doses and inhibitory activity at higher doses. Compounds 1 and 2 could significantly inhibit the radicle growth of dicotyledon weeds, Eclipta prostrata and Veronica persica, at a concentration range from 50 to 200 μg mL, while 3 notably stimulated radicle growth at the same concentration range. The results suggested that these AA derivatives have the potential to be used as the lead scaffold for novel auxin herbicide development. In addition, the biosynthetic pathways of 1-4 were deduced based on C labeling experiment.