Pa. Marchand et al., Convenient synthesis of 2,4-diacetylphloroglucinol, a natural antibiotic involved in the control of take-all disease of wheat, J AGR FOOD, 48(5), 2000, pp. 1882-1887
2,4-Diacetylphloroglucinol (DAPG) is an antibiotic with broad-spectrum anti
bacterial and antifungal activities. It is a major determinant in the biolo
gical control of several plant diseases. DAPG is produced by Pseudomonas fl
uorescens both in vitro and in the rhizosphere of wheat. It is involved in
the natural suppression of take-all disease known as take-all dec line, whi
ch develops in soils following extended monoculture of wheat or barley. A o
ne-step synthesis of DAPG from the commercially available 2-acetylphloroglu
cinol is described. This reaction involves the direct alkylation of 2-acety
lphloroglucinol using acetic anhydride as the acetylation reagent, with bor
on trifluoride-etherate as the catalyst. This synthesis is simple and produ
ces higher yields of DAPG (90%) as compared with previously described proce
dures. As ecological concerns are gaining equal status with agricultural co
ncerns, the demand for natural biocontrol measures is increasing. There is
tremendous pressure from society on agriculture to reduce the use of pestic
ides. A discussion is given on the agricultural and ecological importance o
f this natural antibiotic and its application as an alternative to reduce t
he use of synthetic pesticides.