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Structures and pesticidal activities of derivatives of dinitrophenols. VIII. —effects of substitution with C 5 to C 13 ‐s‐alkyl groups and of esterification on the acaricidal activity of dinitrophenols
Author(s) -
Pianka M.,
Edwards J. D.
Publication year - 1968
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.2740190202
Subject(s) - alkyl , chemistry , tetranychus , phenols , organic chemistry , medicinal chemistry , stereochemistry , spider mite , mite , botany , biology
38 methyl‐, 37 ethyl‐ and 19 other alkyl‐carbonates, 37 crotonates, 10 acrylates and 17 other esters, and 15 methyl ethers of 2‐(C 5 to C 13 ‐s‐alkyl)‐4,6‐dinitro‐ and 4‐(C 4 t4 to C 13 ‐s‐alkyl)‐2,6‐dinitrophenols were synthesised, and their activities against Tetranychus telarius (greenhouse red spider mite) were investigated. 2‐s‐Alkyl‐4,6‐dinitrophenols and esters were more active than their 4‐s‐alkyl‐2,6‐dinitro‐ analogues, acaricidal activity remaining high with the 4,6‐dinitrophenols up to 2‐(C 11 ‐s‐alkyl). Generally compactness of the 2‐s‐alkyl group aided activity. Methyl ethers had very low activity. Esters of 2‐(C 3 to C 7 ‐s‐alkyl)‐4,6‐dinitrophenols were more acaricidal than the parent phenols, but the reverse was the case with C 8 to C 13 ‐s‐alkyl compounds. Crotonates and other esters were generally less active than methyl carbonates. The methyl carbonates of 2‐(1‐ethylhexyl)‐ and 2‐(1‐propylpentyl)‐4,6‐dinitrophenols were found to be of particular economic interest as acaricides.