Inhibitors of biotin biosynthesis as potential herbicides: Part 2

• Published in: Pest management science Vol. 61; no. 10; pp. 1024 - 1033
• Main Authors: Ashkenazi, Tali, Widberg, Ayala, Nudelman, Abraham, Wittenbach, Vernon, Flint, Dennis
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.10.2005; Wiley; Wiley Subscription Services, Inc
• Subjects: Amino Acids - chemistry; Amino Acids - pharmacology; Amino Acids, Diamino - chemistry; Amino Acids, Diamino - pharmacology; Biological and medical sciences; biotin; Biotin - biosynthesis; biotin vitamers; Carbon; enzyme inhibition; Fundamental and applied biological sciences. Psychology; Herbicides; Herbicides - pharmacology; isosteres; Molecular Structure; Parasitic plants. Weeds; Phytopathology. Animal pests. Plant and forest protection; Plants - drug effects; Resistance to control; Weeds; enzyme inhibition; Pesticides; Enzyme inhibitor; Biosynthesis; Biotin; isosteres; biotin vitamers; Biological activity; Herbicide; herbicides
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.1075

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. Copyright © 2005 Society of Chemical Industry