The mobility in phloem of several substituted phosphonic acids and a sulfonic acid was studied in the castor bean plant, Ricinus communis L. For a series of14C‐labelled phosphonate mono‐esters applied to the petioles of mature leaves, phloem transport was modest, becoming poor over longer distances in the plant. Substituted phenylphosphonic acids were more efficiently moved in phloem; uptake from the petiole and subsequent redistribution were slow, but these dibasic compounds were very stable in plants and substantial amounts reached the roots after 72 to 120 h. Glyphosate was very efficiently transported to phloem sinks even within 24 h, with high concentrations in phloem sap. Toluene‐4‐sulfonic acid moved predominantly in the xylem to the mature leaves and its phloem transport was poor. Transport patterns are considered in relation to the physico‐chemical properties of the compounds. Ion trapping appears to play little part in the phloem transport of these strong acids, though the good accumulation and transport in phloem of the complex molecule glyphosate cannot at present be explained.
The movement of [14C]pyridinecarboxylic acids was investigated in the castor bean plant Ricinus communis L. after application by petiole injection. The three isomeric unsubstituted acids appeared in similar concentrations in phloem sap taken from the upper main stem over a period of 6 h after application, but nicotinic acid occurred at higher concentrations than its isomers in phloem sap from the lower stem indicating better retention in the phloem sieve tubes. After 24 h, nicotinic acid had accumulated to a greater extent in the phloem sinks than had picolinic or isonicotinic acids. Phloem transport of substituted analogues, including dihalopyridinecarboxylic acids and imidazolinone herbicides, was measured in short‐term tests, and attempts made to relate such transport to the lipophilicity and pK,a of the compounds. Analogues of the imidazolinone, imazapyr, were less well transported than imazapyr itself, and were also much less well taken up by barley roots from nutrient solution compared to the herbicidal imidazolinone, and this could explain their low herbicidal efficacy despite a high intrinsic activity against the target enzyme acctolactate synthase.
A series of 14C‐labelled benzoic acids, chosen to permit assessment of the role of pKa and lipophilicity in determining movement in plants of these herbicide analogues, was synthesised and their phloem translocation investigated. Following application of substituted benzoic acids to castor bean, Ricinus communis L., by injection into the petioles, the compounds of intermediate lipophilicity (2‐fluoro‐, 4‐chloro‐ and 3,4‐dichlorobenzoic acids) gave highest concentrations in phloem exudates; 4‐methyl‐2,3,5,6‐tetrafluoro‐ and pentafluorobenzoic acids were less well translocated, perhaps because their pKa values are much less than those of the other benzoic acids studied. The polar 4‐ureidobenzoic acid and the lipophilic 3‐(4‐methylphenoxy)benzoic acid were much less efficiently translocated in phloem. These results are similar to those previously obtained for phenoxyacetic acids, and provide further support for the role of ionisation in the accumulation and retention of chemicals in phloem sieve tubes.
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