Drazepinone, a trisubstituted tetrahydronaphthofuroazepinone with herbicidal activity produced by Drechslera siccans.
When grown in a minimal-defined medium, a strain of Drechslera siccans, a pathogenic fungus isolated from seeds of Lolium perenne, produced phytotoxic metabolites. This strain is one of the best toxin producers among several grass pathogenic fungal strains collected and tested to find phytotoxins to be used as natural herbicides of monocot weeds. From the culture filtrates of D. siccans, we isolated a new phytotoxic trisubstituted naphthofuroazepinone, named drazepinone, and characterised it as a 3,5,12a-trimethyl-2,5,5a,12a-tetrahydro-1H-naphtho[2',3':4,5]furo[2,3-b]azepin-2-one. Assayed at 2 microg microl(-1) solution the novel metabolite proved to have broad-spectrum herbicidal properties, without antibacterial and antifungal activities, and low zootoxic activity. Its original chemical structure and the interesting biological properties make drazepinone a potential natural herbicide.
Evidente
Antonio
A
Dipartimento di Scienze del Suolo della Pianta e dell'Ambiente, Università di Napoli Federico II, Via Università 100, I-80055 Portici, Italy. evidente@unina.it
Andolfi
Anna
A
Vurro
Maurizio
M
Fracchiolla
Mariano
M
Zonno
Maria Chiara
MC
Motta
Andrea
A
D001203:Ascomycota / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006540:Herbicides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves
D001381:Azepines; D006540:Herbicides; D009281:Naphthalenes; C501249:drazepinone