Synthesis and biological activities of 4-chloroindole-3-acetic acid and its esters.
4-Chloroindole-3-acetic acid (4-Cl-IAA) and its esters were synthesized from 2-chloro-6-nitrotoluene as the starting material. The biological activities of 4-CI-IAA and its esters were determined by four bioassays. Except for the tert-butyl ester, 4-Cl-IAA and its esters had stronger elongation activity toward Avena coleoptiles than had indole-3-acetic acid. The biological activities of the methyl, ethyl and allyl esters were as strong as the activity of the free acid. All the esters, except for the tert-butyl, inhibited Chinese cabbage hypocotyl growth more than the free acid did, and all the esters induced severe swelling and formation of numerous lateral roots in black gram seedlings even at a low concentration. Furthermore, adventitious root formation was strongly promoted in Serissa japonica cuttings by all the esters. The root formation-promoting activities of the ethyl and allyl esters were about three times the value for indole-3-butyric acid which is used to promote and accelerate root formation in plant cuttings.
Katayama
M
M
Department of Chemistry, National Industrial Research Institute of Nagoya, Japan. katayama@nirin.go.jp
D018554:Avena / Q000254:growth & development; D001937:Brassica / Q000254:growth & development; D004952:Esters / Q000138:chemical synthesis / Q000378:metabolism*; D007210:Indoleacetic Acids / Q000138:chemical synthesis / Q000378:metabolism*; D018517:Plant Roots / Q000254:growth & development
D004952:Esters; D007210:Indoleacetic Acids; C096198:4-chloroindole-3-acetic acid