Aryl chain analogues of the biotin vitamers as potential herbicides. Part 3.
Novel aryl chain isosters 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. In the greenhouse test the most active compounds were the fluorinated derivative 9d and the selenophenyl/furan mixture 17m/17p, which were most active against Foxtail millet. In the more sensitive Arabidopsis test the most active substances were 9a and 17m, which displayed GR(50) (concentration of active compound causing 50% growth inhibition) values of 0.2 and 0.5 mg kg(-1) respectively (values of < 50 mg kg(-1) are considered herbicidal).
Chemistry Department, Bar Ilan University, Ramat Gan 52900, Israel.
Tali
T
Ashkenazi
Dalia
D
Pinkert
Ayelet
A
Nudelman
Ayala
A
Widberg
Barry
B
Wexler
Vernon
V
Wittenbach
Dennis
D
Flint
Abraham
A
Nudelman
D000596:Amino Acids / Q000737:chemistry*; D000599:Amino Acids, Diamino / Q000737:chemistry*; D001710:Biotin / Q000096:biosynthesis; D006540:Herbicides / Q000138:chemical synthesis*; D019684:Magnoliopsida; D008968:Molecular Conformation
D000596:Amino Acids; D000599:Amino Acids, Diamino; D006540:Herbicides; C004720:7,8-diaminopelargonic acid; C001502:7-keto-8-aminopelargonic acid; D001710:Biotin