Ribofuranosyl triazolone: a natural product herbicide with activity on adenylosuccinate synthetase following phosphorylation.
2,4-Dihydro-4-(beta-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one (2) was identified as the principal phytotoxic component of a fermentation broth derived from an Actinomadura. The compound is a new natural product, but known by synthesis. Broad-spectrum herbicidal activity was demonstrated in greenhouse tests. Metabolite reversal studies suggested the target site was adenylosuccinate synthetase, which was confirmed by direct measurement of the activity of the 5'-phosphorylated derivative on the isolated enzyme.
Schmitzer
P R
PR
Dow AgroSciences, 9330 Zionsville Road, Indianapolis, Indiana 46268, USA.
Graupner
P R
PR
Chapin
E L
EL
Fields
S C
SC
Gilbert
J R
JR
Gray
J A
JA
Peacock
C L
CL
Gerwick
B C
BC
D000265:Adenylosuccinate Synthase / Q000037:antagonists & inhibitors*; D000818:Animals; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D006540:Herbicides / Q000494:pharmacology*; D006827:Hydantoins / Q000494:pharmacology; D010766:Phosphorylation; D011817:Rabbits; D012266:Ribose / Q000494:pharmacology*; D014230:Triazoles / Q000494:pharmacology*; D003313:Zea mays
D004791:Enzyme Inhibitors; D006540:Herbicides; D006827:Hydantoins; D014230:Triazoles; C068815:hydantocidin; D012266:Ribose; D000265:Adenylosuccinate Synthase