Convenient synthesis of 2,4-diacetylphloroglucinol, a natural antibiotic involved in the control of take-all disease of wheat

Citation
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
Citations number
20
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis
Journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN journal
00218561 → ACNP
Volume
48
Issue
5
Year of publication
2000
Pages
1882 - 1887
Database
ISI
SICI code
0021-8561(200005)48:5<1882:CSO2AN>2.0.ZU;2-O
Abstract
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.