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Studies on plant growth‐regulating substances. XL. 2‐Chloro‐3‐phenylpropionitriles
Author(s) -
KEMP M. S.,
WAIN R. L.
Publication year - 1976
Publication title -
annals of applied biology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.677
H-Index - 80
eISSN - 1744-7348
pISSN - 0003-4746
DOI - 10.1111/j.1744-7348.1976.tb00595.x
Subject(s) - propionitrile , coleoptile , biology , auxin , propanoic acid , plant growth , phenylacetic acid , metabolism , ring (chemistry) , stereochemistry , biochemistry , botany , organic chemistry , chemistry , acetonitrile , gene
SUMMARY The complete series of chloro‐, dichloro‐, methyl‐, dimethyl‐ and chloro‐methyl‐ring substituted 2‐chloro‐3‐phenylpropionitriles and several related compounds have been prepared. Their auxin activities have been assessed in the wheat coleoptile, pea segment and pea curvature tests, and the results, which are discussed in relation to molecular structure, support the suggestion by other workers that the observed activity is due to rapid uptake of the nitriles by the plant tissues, followed by metabolism to the corresponding phenylacetic acid. The high growth promoting activity of 2‐chloro‐3‐(3‐chloro‐2‐methyl‐phenyl)propionitrile (orthonil) is confirmed but 2‐chloro‐3‐(2,3‐dichloro‐phenyl)propionitrile and 2‐chloro‐3‐(2,3‐dichlorophenyl)butyronitrile are shown to be the most active members of the series.