Journal
TETRAHEDRON
Volume 60, Issue 8, Pages 1731-1748Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.12.047
Keywords
biotin; biotin vitamers; 7-keto-8-aminopelerginic acid (KAPA); 7,8-diaminopelargonic acid (DAPA); desthiobiotin (DTB); herbicides; enzyme inhibitors
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Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR(50) (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity. (C) 2003 Elsevier Ltd. All rights reserved.
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