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The permeation barrier of plant cuticles: uptake of active ingredients is limited by very long-chain aliphatic rather than cyclic wax compounds.

Abstract

BACKGROUND

The barrier to diffusion of organic solutes across the plant cuticle is composed of waxes consisting of very long-chain aliphatic (VLCA) and, to varying degrees, cyclic compounds like pentacyclic triterpenoids. The roles of both fractions in controlling cuticular penetration by organic solutes, e.g. the active ingredients (AI) of pesticides, are unknown to date. We studied the permeability of isolated leaf cuticular membranes from Garcinia xanthochymus and Prunus laurocerasus for lipophilic azoxystrobin and theobromine as model compounds for hydrophilic AIs.

RESULTS

The wax of P. laurocerasus consists of VLCA (12%) and cyclic compounds (88%), whereas VLCAs make up 97% of the wax of G. xanthochymus. We show that treating isolated cuticles with methanol almost quantitatively releases the cyclic fraction while leaving the VLCA fraction essentially intact. All VLCAs were subsequently removed using chloroform. In both species, the permeance of the two model compounds did not change significantly after methanol treatment, whereas chloroform extraction had a large effect on organic solute permeability.

CONCLUSION

The VLCA wax fraction makes up the permeability barrier for organic solutes, whereas cyclic compounds even in high amounts have a negligible role. This is of significance when optimizing the foliar uptake of pesticides. © 2019 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Authors+Show Affiliations

University of Würzburg, Julius von Sachs Institute of Biosciences, Chair of Botany II - Ecophysiology and Vegetation Ecology, Würzburg, Germany.University of Würzburg, Julius von Sachs Institute of Biosciences, Chair of Botany II - Ecophysiology and Vegetation Ecology, Würzburg, Germany.University of Würzburg, Julius von Sachs Institute of Biosciences, Chair of Botany II - Ecophysiology and Vegetation Ecology, Würzburg, Germany.University of Würzburg, Julius von Sachs Institute of Biosciences, Chair of Botany II - Ecophysiology and Vegetation Ecology, Würzburg, Germany.Syngenta Crop Protection, Application Technology Group, Münchwilen, Switzerland.University of Würzburg, Julius von Sachs Institute of Biosciences, Chair of Botany II - Ecophysiology and Vegetation Ecology, Würzburg, Germany.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31436379

Citation

Staiger, Simona, et al. "The Permeation Barrier of Plant Cuticles: Uptake of Active Ingredients Is Limited By Very Long-chain Aliphatic Rather Than Cyclic Wax Compounds." Pest Management Science, 2019.
Staiger S, Seufert P, Arand K, et al. The permeation barrier of plant cuticles: uptake of active ingredients is limited by very long-chain aliphatic rather than cyclic wax compounds. Pest Manag Sci. 2019.
Staiger, S., Seufert, P., Arand, K., Burghardt, M., Popp, C., & Riederer, M. (2019). The permeation barrier of plant cuticles: uptake of active ingredients is limited by very long-chain aliphatic rather than cyclic wax compounds. Pest Management Science, doi:10.1002/ps.5589.
Staiger S, et al. The Permeation Barrier of Plant Cuticles: Uptake of Active Ingredients Is Limited By Very Long-chain Aliphatic Rather Than Cyclic Wax Compounds. Pest Manag Sci. 2019 Aug 22; PubMed PMID: 31436379.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The permeation barrier of plant cuticles: uptake of active ingredients is limited by very long-chain aliphatic rather than cyclic wax compounds. AU - Staiger,Simona, AU - Seufert,Pascal, AU - Arand,Katja, AU - Burghardt,Markus, AU - Popp,Christian, AU - Riederer,Markus, Y1 - 2019/08/22/ PY - 2019/07/15/received PY - 2019/08/15/accepted PY - 2019/8/23/pubmed PY - 2019/8/23/medline PY - 2019/8/23/entrez KW - active ingredients KW - cuticular permeability KW - cyclic compounds KW - pesticides KW - very long-chain aliphatic compounds JF - Pest management science JO - Pest Manag. Sci. N2 - BACKGROUND: The barrier to diffusion of organic solutes across the plant cuticle is composed of waxes consisting of very long-chain aliphatic (VLCA) and, to varying degrees, cyclic compounds like pentacyclic triterpenoids. The roles of both fractions in controlling cuticular penetration by organic solutes, e.g. the active ingredients (AI) of pesticides, are unknown to date. We studied the permeability of isolated leaf cuticular membranes from Garcinia xanthochymus and Prunus laurocerasus for lipophilic azoxystrobin and theobromine as model compounds for hydrophilic AIs. RESULTS: The wax of P. laurocerasus consists of VLCA (12%) and cyclic compounds (88%), whereas VLCAs make up 97% of the wax of G. xanthochymus. We show that treating isolated cuticles with methanol almost quantitatively releases the cyclic fraction while leaving the VLCA fraction essentially intact. All VLCAs were subsequently removed using chloroform. In both species, the permeance of the two model compounds did not change significantly after methanol treatment, whereas chloroform extraction had a large effect on organic solute permeability. CONCLUSION: The VLCA wax fraction makes up the permeability barrier for organic solutes, whereas cyclic compounds even in high amounts have a negligible role. This is of significance when optimizing the foliar uptake of pesticides. © 2019 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. SN - 1526-4998 UR - https://www.unboundmedicine.com/medline/citation/31436379/The_permeation_barrier_of_plant_cuticles:_uptake_of_active_ingredients_is_limited_by_very_long_chain_aliphatic_rather_than_cyclic_wax_compounds_ L2 - https://doi.org/10.1002/ps.5589 DB - PRIME DP - Unbound Medicine ER -