Phytogrowth-inhibitory activities of 2-thiophenecarboxylic acid and its related compounds.
2-Thiophenecarboxylic acid (I) exhibited growth-inhibitory activity in five kinds of plants. In particular, I strongly inhibited the growth of the roots of Lactuca sativa L. var. longifolia LAM and Echinochloa utilis OHWI et YABUNO, even at the low concentration of 5.0 x 10(-3) M. Furthermore, all of the I-related compounds (II-V and VII-X) except for VI, showed more or less obvious inhibitory activity on the seeds of Sesamum indicum L. Compounds VII-X, in which the carboxyl group of I was replaced by acetic acid, propionic acid, butyric acid and acrylic acid, and exhibited more potent phytogrowth-inhibitory activity than I. Among these compounds, 2-thiophenebutyric acid (IX) showed the strongest activity. Esterification of the carboxyl group in I increased the inhibitory activity relative to that of I, while amidation and reduction of this group markedly decreased its inhibitory activity. The radicles of the plants treated with each of the compounds except for VI showed negative geotropism, even though germination occurred.
Inamori
Y
Y
Osaka University of Pharmaceutical Sciences, Japan.
Muro
C
C
Funakoshi
Y
Y
Usami
Y
Y
Tsujibo
H
H
Numata
A
A
D002264:Carboxylic Acids; D063245:Plant Development; D010937:Plant Growth Regulators / Q000494:pharmacology*; D010944:Plants / Q000187:drug effects*; D012639:Seeds / Q000187:drug effects; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000494:pharmacology*
D002264:Carboxylic Acids; D010937:Plant Growth Regulators; D013876:Thiophenes; C550746:2-thiophene carboxylic acid