Inhibitors of biotin biosynthesis as potential herbicides: part 2.
Isosteres and analogues of 7-keto-8-aminopelargonic acid (KAPA) and 7,8-diaminopelargonic acid (DAPA), the vitamer intermediates involved in the biosynthetic pathway of biotin, possessing chain lengths of eight carbon atoms, were prepared and evaluated as potential herbicides. The most active compounds, 7-amino-octanoic acid hydrochloride and 7-allyloxy-6-oxo-octanoic acid, displayed Arabidopsis GR50 (concentration of the active compound that causes a 50% growth inhibition) values of 5 and 10 mg kg(-1) respectively. The DAPA analog 6,7-diamino-octanoic acid dihydrochloride, when tested in the greenhouse against six weed species, displayed moderate activity against three species, being most active against foxtail millet.
Ashkenazi
Tali
T
Department of Chemistry, Bar Ilan University, Ramat Gan 52900, Israel.
Widberg
Ayala
A
Nudelman
Abraham
A
Wittenbach
Vernon
V
Flint
Dennis
D
D000596:Amino Acids / Q000737:chemistry* / Q000494:pharmacology; D000599:Amino Acids, Diamino / Q000737:chemistry* / Q000494:pharmacology; D001710:Biotin / Q000096:biosynthesis*; D006540:Herbicides / Q000494:pharmacology*; D015394:Molecular Structure; D010944:Plants / Q000187:drug effects
D000596:Amino Acids; D000599:Amino Acids, Diamino; D006540:Herbicides; C004720:7,8-diaminopelargonic acid; C001502:7-keto-8-aminopelargonic acid; D001710:Biotin