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Pestic Biochem Physiol

Title:		Predicting herbicide movement across semi-permeable membranes using three phase partitioning
Author(s):		Takano HK; Patterson EL; Nissen SJ; Dayan FE; Gaines TA;
Address:		"Department of Bioagricultural Sciences and Pest Management, Colorado State University, 1177 Campus Delivery, Fort Collins, CO 80523, USA. Electronic address: Hudson.Takano@colostate.edu. Department of Plant and Environmental Sciences, Clemson University, 171 Poole Agricultural Center, Clemson, SC 29634, USA. Electronic address: elpatte@clemson.edu. Department of Bioagricultural Sciences and Pest Management, Colorado State University, 1177 Campus Delivery, Fort Collins, CO 80523, USA. Electronic address: Scott.Nissen@colostate.edu. Department of Bioagricultural Sciences and Pest Management, Colorado State University, 1177 Campus Delivery, Fort Collins, CO 80523, USA. Electronic address: Franck.Dayan@colostate.edu. Department of Bioagricultural Sciences and Pest Management, Colorado State University, 1177 Campus Delivery, Fort Collins, CO 80523, USA. Electronic address: Todd.Gaines@colostate.edu"
Journal Title:		Pestic Biochem Physiol
Year:		2019
Volume:		20190517
Issue:
Page Number:		22 - 26
DOI:		10.1016/j.pestbp.2019.05.009
ISSN/ISBN:		1095-9939 (Electronic) 0048-3575 (Linking)
Abstract:		"Herbicide efficacy depends on herbicides crossing cell and organelle membranes. We evaluated an artificial membrane system to understand how herbicides cross biological membranes. This understanding aids in predicting herbicide behavior in planta and, consequently, efficacy, mode of action, and whether active transporter-based herbicide resistance mechanisms may be possible. Five herbicides with different log K(ow) and pK(a) values were assessed: glyphosate, 2,4-D, clopyralid, sulfentrazone and glufosinate. The artificial membrane apparatus included four semipermeable membranes containing buffers with pH?ª+2.7, 5 and/or 7.4, floating in a bath of diethyl ether. These conditions were based on the pH from different cellular compartments and the pK(a) for these herbicides. Changes in herbicide concentration due to movement were measured using radioactivity or liquid chromatography mass spectrometry. In general, herbicide behavior followed the pattern predicted by their calculated pK(a) and log K(ow). Herbicides added to an acidic phase (pH?ª+2.7) were more mobile than when they were added to the more basic phase (pH?ª+7.4), except when herbicide's pK(a) was lower than the pH of the starting phase. Clopyralid, 2,4-D, and sulfentrazone showed significant acid trapping behavior due to their weak acid functional groups. Sulfentrazone and 2,4-D had a high affinity for the nonpolar, diethyl ether bath, especially when they were protonated at low pH. Our findings illustrate the robustness of the system to provide predictions about herbicide behavior at the subcellular level"
Keywords:		"2, 4-Dichlorophenoxyacetic Acid/metabolism Aminobutyrates/metabolism Glycine/analogs & derivatives/metabolism Herbicides/*metabolism Hydrogen-Ion Concentration Membranes, Artificial Picolinic Acids/metabolism Sulfonamides/metabolism Triazoles/metabolism Ab;"
Notes:		"MedlineTakano, Hudson K Patterson, Eric L Nissen, Scott J Dayan, Franck E Gaines, Todd A eng 2019/08/12 Pestic Biochem Physiol. 2019 Sep; 159:22-26. doi: 10.1016/j.pestbp.2019.05.009. Epub 2019 May 17"