Hostname: page-component-8448b6f56d-qsmjn Total loading time: 0 Render date: 2024-04-24T16:32:20.173Z Has data issue: false hasContentIssue false

Relationships between compound lipophilicity on seed coat permeability and embryo uptake by soybean and corn

Published online by Cambridge University Press:  22 May 2018

Daibin Yang
Affiliation:
School of Integrated Plant Science, Section of Horticulture, NYSAES, Cornell University, Geneva, NY 14456, USA Institute of Plant Protection, Chinese Academy of Agricultural Science, Beijing 100193, China
Stephen Donovan
Affiliation:
Agricultural Chemist
Bruce C Black
Affiliation:
Chemical Entomologist
Lailiang Cheng
Affiliation:
School of Integrated Plant Science, Section of Horticulture, Cornell University, Ithaca, NY 14853, USA
Alan G Taylor*
Affiliation:
School of Integrated Plant Science, Section of Horticulture, NYSAES, Cornell University, Geneva, NY 14456, USA
*
Author for correspondence: Alan G. Taylor, Email: agt1@cornell.edu

Abstract

Systemic uptake of organic compounds from roots to leaves follows a Gaussian distribution in relation to the lipophilicity, as measured by the log Kow. Quantification of compound uptake with different lipophilicities, and applied as a seed treatment that diffuses through the seed coat into the embryo during imbibition, has not been reported. The aim of this investigation was to quantify the uptake of non-ionic compounds into seeds of soybean and corn. A series of fluorescent piperonyl amides were synthesized and a novel combinatorial pharmacodynamic technique was developed that provided a range of compounds from log Kow 0.02 to 5.7. Seeds were treated with a mixture of amides, imbibed and compounds chemically extracted and quantified by high-performance liquid chromatography using a fluorescence detector. The maximum uptake efficiency of the applied amide mixture from whole soybean and corn seeds was 67% at log Kow 2.9, and 43% at log Kow 3.4, respectively. The critical partition coefficient for uptake for both species was <4.2 log Kow. Seeds were dissected and separated as soybean embryo and testa, and corn internal tissues (embryo + endosperm) or seed covering layers (pericarp + testa), and >75% of the amides were found in the soybean embryo or corn internal tissues compared with the covering layers at log Kow <4.2. The distribution of amides showed that the corn seed covering layer had similar hydrophilic/lipophilic properties as internal tissues, while soybean tissues had different hydrophilic/lipophilic properties. Collectively, the Gaussian uptake pattern for systemic uptake into plants was not found for either seed species.

Type
Research Paper
Copyright
Copyright © Cambridge University Press 2018 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Aajoud, A, et al. (2006) Uptake and xylem transport of fipronil in sunflower. Journal of Agricultural and Food Chemistry 54, 50555060.Google Scholar
Anastassiades, M et al. (2003) Fast and easy multiresidue method employing acetonitrile extraction/partitioning and “dispersive solid-phase extraction” for the determination of pesticide residues in produce. Journal of AOAC International 86, 412431.Google Scholar
Avram, S et al. (2014) Quantitative estimation of pesticide-likeness for agrochemical discovery. Journal of Cheminformatics 6, 42.Google Scholar
Beresniewicz, M et al. (1995) Chemical nature of a semipermeable layer in seed coats of leek, onion (Liliaceae), tomato and pepper (Solanaceae). Seed Science and Technology 23, 135145.Google Scholar
Brandl, F (2001) Seed treatment technologies: evolving to achieve crop genetic potential. British Crop Protection Council Symposium Proceedings 76, 318.Google Scholar
Braumann, T (1986) Determination of hydrophobic parameters by reversed-phase liquid chromatography: theory, experimental techniques, and application in studies on quantitative structure-activity relationships. Journal of Chromatography A 373, 191225.Google Scholar
Briggs, GG, Bromilow, RH and Evans, AA (1982) Relationships between lipophilicity and root uptake and translocation of non-ionised chemicals by barley. Pesticide Science 13, 495504.Google Scholar
Collins, C, Fryer, M and Grosso, A (2006) Plant uptake of non-ionic organic chemicals. Environmental Science and Technology 40, 4552.Google Scholar
Dias, MAN, Taylor, AG and Cicero, SM (2014) Uptake of systemic seed treatments by maize evaluated with fluorescent tracers. Seed Science and Technology 42, 101107.Google Scholar
Donovan, SF and Pescatore, MC (2002) Method for measuring the logarithm of the octanol–water partition coefficient by using short octadecyl–poly(vinyl alcohol) high-performance liquid chromatography columns. Journal of Chromatography A 952, 4761.Google Scholar
Elbert, A et al. (2008) Applied aspects of neonicotinoid uses in crop protection. Pest Management Science. 64, 10991105.Google Scholar
Hao, G, Dong, Q and Yang, G (2011) A comparative study on the constitutive properties of marketed pesticides. Molecular Informatics. 30, 614622.Google Scholar
Hsieh, M-M and Dorsey, JG (1995) Bioavailability estimation by reversed-phase liquid chromatography: high bonding density C-18 phases for modeling biopartitioning processes. Analytical Chemistry 67, 4857.Google Scholar
Hsu, FC, Marxmiller, RL and Yang, AYS (1990) Study of root uptake and xylem translocation of cinmethylin and related compounds in detopped soybean roots using a pressure chamber technique. Plant Physiology 93, 15731578.Google Scholar
Koizumi, M and Kano, H (2014) Water entry in dry soybeans at imbibition observed by dedicated micro-magnetic resonance imaging. American Journal of Life Sciences 2, 611.Google Scholar
Koizumi, M et al. (2008) Role of seed coat in imbibing soybean seeds observed by micro-magnetic resonance imaging. Annals of Botany 102, 343352.Google Scholar
Lipinski, CA, Lombardo, F, Dominy, BW and Feeney, PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews 46, 326.Google Scholar
Maienfisch, P et al. (2001) Chemistry and biology of thiamethoxam: a second generation neonicotinoid. Pest Management Science 57, 906913.Google Scholar
McDonald, M, Sullivan, J and Lauer, M (1994) The pathway of water uptake in maize seeds. Seed Science and Technology 22, 7990.Google Scholar
Niemann, S et al. (2013) Aqueous pathways dominate permeation of solutes across Pisum sativum seed coats and mediate solute transport via diffusion and bulk flow of water. Plant, Cell and Environment 36, 10271036.Google Scholar
Rowland, M and Tozer, TN (2011) Clinical Pharmacokinetics and Pharmacodynamics: Concepts and Applications (4th edition). Philadelphia, USA: Lippincott Williams and Wilkins.Google Scholar
Salanenka, YA and Taylor, AG (2009) Uptake of model compounds by soybean, switchgrass and castor seeds applied as seed treatments, pp. 7681 in Symposium Proceedings of the British Crop Protection Council: Seed Production and Treatment in a Changing Environment. Alton, Hampshire, UK: British Crop Protection Council.Google Scholar
Salanenka, YA and Taylor, AG (2011) Seedcoat permeability: uptake and post-germination transport of applied model tracer compounds. HortScience 46, 622626.Google Scholar
Salanenka, YA, Goffinet, MC and Taylor, AG (2009) Structure and histochemistry of the micropylar and chalazal regions of the perisperm–endosperm envelope of cucumber seeds associated with solute permeability and germination. Journal of the American Society for Horticultural Science 134, 479487.Google Scholar
Satchivi, NM (2014) Modeling xenobiotic uptake and movement: a review, pp. 41–74 in Retention, Uptake, and Translocation of Agrochemicals in Plants. American Chemical Society. Symposium Series, vol. 1171.Google Scholar
Schwab, AP, Al-Assi, A and Banks, M (1998) Adsorption of naphthalene onto plant roots. Journal of Environmental Quality 27, 220224.Google Scholar
Taylor, AG and Salanenka, YA (2012) Seed treatments: phytotoxicity amelioration and tracer uptake. Seed Science Research 22, S8690.Google Scholar
Tice, CM (2001) Selecting the right compounds for screening: does Lipinski's rule of 5 for pharmaceuticals apply to agrochemicals? Pest Management Science 57, 316.Google Scholar
Trapp, S (2004) Plant uptake and transport models for neutral and ionic chemicals. Environmental Science and Pollution Research 11, 3339.Google Scholar
Uchida, M (1980) Affinity and mobility of fungicidal dialkyl dithiolanylidenemalonates in rice plants. Pesticide Biochemistry and Physiology 14, 249255.Google Scholar
Veber, DF et al. (2002) Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry 45, 26152623.Google Scholar
Yang, D et al. (2017) Compound lipophilicity and implications for seed treatment efficacy, 32nd Annual Tomato Disease Workshop. Tampa, Florida, USA.Google Scholar