Retention, uptake, and translocation of agrochemicals in plants

218 Pages·2014·10.52 MB·English

by  Kingston

Retention, Uptake, and
Translocation of
Agrochemicals in Plants

In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
1171
ACS SYMPOSIUM SERIES
Retention, Uptake, and
Translocation of
Agrochemicals in Plants
Kyung Myung, Editor
Dow AgroSciences
Indianapolis, Indiana
Norbert M. Satchivi, Editor
Dow AgroSciences
Indianapolis, Indiana
Coleen K. Kingston, Editor
DuPont Crop Protection
Newark, Delaware
Sponsored by the
ACS Division of Agrochemicals

AmericanChemicalSociety,Washington,DC
DistributedinprintbyOxfordUniversityPress
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
LibraryofCongressCataloging-in-PublicationData
Retention,uptake,andtranslocationofagrochemicalsinplants/KyungMyung,editor,
DowAgroSciences, Indianapolis,Indiana,NorbertM.Satchivi,editor,DowAgroScences,
Indianapolis,Indiana,ColeenK.Kingston,editor,DupontCropProtection,Newark,
Delaware ;sponsoredbytheACSDivisionofAgrochemicals.
pagescm.-- (ACSsymposiumseries;1171)
Includesbibliographicalreferencesandindex.
ISBN978-0-8412-2972-3(alk.paper)
1. Plants--Effectofagriculturalchemicalson.2. Planttranslocation. I.Myung,Kyung.
II.AmericanChemicalSociety.DivisionofAgrochemicals.
QK746.R482014
580--dc23
2014035822
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In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
Foreword
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In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
Preface
Fundamental understanding of the uptake, translocation, and distribution
of agrochemicals is of great interest among scientists in industry and academia,
because biological activities of pesticides against their target species can be
significantlyinfluencedbythebiokineticsofthepesticides. Biologicalactivityof
pesticides is initially identified during the courses of in vitro bioassays, but the
activemoleculesoftenlosetheirbiologicalactivityingreenhousetests. Thelack
oftranslationofactivitybetweeninvitroassaysandgreenhousetestsisgenerally
associated with many factors, including poor retention on plant surface, lack of
foliar or root uptake, and limited systemicity within plants. Therefore, a clear
understanding of the factors that govern the effectiveness of pesticides is key to
overcome certain barriers for the expression of biological activity, and this can
leadtoastrategytoimprovebiologicalperformance.
This ACS symposium book is based on a symposium that was held at the
246thAmericanChemicalSocietyNationalMeeting&ExpositioninIndianapolis,
Indiana from September 8-12, 2013. Although uptake, translocation, and
distribution of agrochemicals in plants have been extensively studied over the
years, there are still many unanswered questions that need to be addressed.
This book aims to update current knowledge with new studies that contain new
findingsontheuptake,translocation,anddistributionofagrochemicalsinplants
as well as provide review-style chapters that summarize existing information on
specificsubjects.
It is hoped that this book will serve as a valuable resource for researchers
who study uptake, translocation, and distribution of pesticides in plants. As
researchers involved in discovery and development of agrochemicals want to
understand a broad range of biological factors, it is also hoped that this book
promotes researchers in other scientific disciplines to generate new ideas and
technologies in the process of new product development. Knowledge of the
biokineticswillhelpusfurtherunderstandtheuseofagrochemicalsonourplanet.

We thank the presenters and authors for their invaluable contributions to
the symposium and this book. We gratefully acknowledge ACS division of
agrochemicalsandDowAgroSciencesforfinancialassistanceforthesymposium.
We would like to express our sincere thanks to many other colleagues who
reviewed chapters for their timely and critical assessment. We are also thankful
forexcellentsupportsofstaffmembersinACSBooksDivision.
ix
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
KyungMyung
CropProtectionBiology,DiscoveryResearch,DowAgroSciences
9330ZionsvilleRoad,Indianapolis,IN46268,USA
317-337-7104(telephone)
317-337-3205(fax)
[email protected](e-mail)
NorbertM.Satchivi
CropProtectionBiology,DiscoveryResearch,DowAgroSciences
9330ZionsvilleRoad,Indianapolis,IN46268,USA
317-337-4128(telephone)
317-337-3265(fax)
[email protected](e-mail)
ColeenK.Kingston
DuPontCropProtection
ElktonRoad,Newark,DE19714,USA
302-451-3335(telephone)
302-451-3570(fax)
[email protected](e-mail)

x
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
Editors’ Biographies
Kyung Myung
KyungMyungreceivedhisB.S.andM.S.degreesinHorticulturefromKyung
HeeUniversity,SouthKoreaandPennsylvaniaStateUniversity,respectively,and
his Ph.D. degree in Plant Physiology from University of Kentucky. Since then
hehasworkedforNorthernIllinoisUniversityandUSDA-ARSandthenjoined
DiscoveryResearchDepartmentatDowAgroSciences. Heiscurrentlyengaged
in research in biokinetics of pesticides in biological matrices. He has published
over20researcharticlesinthefieldofagriculturalbiologyandchemistry.
Norbert M. Satchivi
Norbert M. Satchivi obtained his Bachelor degree in Plant Physiology from
the Université d’Abidjan (Cote-d’Ivoire) and his Doctorate from the Université
de Perpignan in France (Agrochemistry). He was a Postdoctoral Scientist at the
UniversityofIllinoisatUrbana-Champaignwhereheworkedonthedevelopment
ofcomputersimulationmodelsforthemovementofxenobioticsinplant. Healso
worked at the University of Guelph (Ontario, Canada) as a Research Scientist
focusing on the mechanisms of herbicide antagonism. He is currently a Senior
Research Scientist with Dow AgroSciences with a focus in herbicide discovery.
Publications included the areas of herbicide characterization, xenobiotic uptake
andtransport,andmodelingxenobioticmovement.
Coleen K. Kingston

Coleen K. Kingston obtained her Bachelor degree from the University of
Wisconsin (Biochemistry, Math) and her Doctorate from Purdue University in
Indiana (Analytical Chemistry). Subsequent posts have included research and
development scientific positions within the pharmaceutical and agrochemical
industries. SheiscurrentlyaseniorscientistwithDuPontCropProtectionwitha
specialty in crop residue human safety assessment. Publications over the years
haveincludedtheareasofpharmaceuticalanalysismethoddevelopmentinhuman
matrices and the prediction of residues in food and feedstuffs yielded following
foliarandsystemicdeliveryapplicationofcropprotectionchemicals.
©2014AmericanChemicalSociety
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
Chapter 1
Spray Retention of Crop Protection
Agrochemicals on the Plant Surface
ChenglinYao,*KyungMyung,NickWang,andAlexandriaJohnson
DowAgroSciences,9330ZionsvilleRoad,Indianapolis,Indiana46268
*E-mail: [email protected].
Retention efficiency of crop protection products, one of the
importantattributesfordeliveringbiologicalefficacy,ismainly
determined by the physicochemical properties of the spray
formulations and the surface characteristics of target plants.
In this chapter, effects of plant leaf surface characteristics,
developmental stages and canopy density on leaf wettability
and spray retention are reviewed. Factors modifying the
physicochemical properties of spray liquids, including active
ingredients, formulation types, and a variety of adjuvants
are also discussed. Using a quantitative structure-activity
relationship (QSAR) analysis, we have developed a model
based on four calculated physicochemical properties of a
training set of 17 fungicides to predict compound retention
rates on wheat seedling plants. The model was validated by a

strongcorrelationbetweenexperimentallydeterminedretention
ratesandpredictedvaluesofasmalltestset,whichincludedsix
additional fungicide compounds. Retention efficiency of three
epoxiconazoleformulationswasalsoevaluated,andsignificant
differences in retention were observed for the products Ignite
(8 % EC, w/w), Opus (12.1% SC, w/w), and a generic lab SC
(10%w/w).
©2014AmericanChemicalSociety
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;
Introduction
Highefficiencysprayretentionontheplantsurfaceisrequiredformaximizing
activitydeliveryofcropprotectionagrochemicalsbecauseitincreasestheamount
ofactiveingredientpotentiallyavailableforreachingthebiologicalsiteofaction.
Retention is the overall capture of spray droplets by a plant and determines the
amountofactiveingredientonaplant. Itisdependentonthecomplexinterfacial
interaction of spray droplets and the plant surface. The factors considered to be
important for spray liquid adhesion and retention include: 1) physicochemical
properties of the spray solutions; 2) diameter spectra and impaction velocity of
spray droplets; and 3) characteristics of plant surface, shape and orientation of
the target leaves and density of plant canopy. While the impact of adjuvants on
theinteractionofsprayliquidsandleafsurfacehasbeenextensivelystudiedand
reviewed(1–4),specificallytheeffectofmajoradditivesinthesprayformulations
such as solvents, surfactants, oil and polymer adjuvants, attention to the active
ingredients has not been the focus for the majority of the studies. For plants,
wettabilityoftheleafsurfaceistypicallygovernedbysurfaceroughnesscaused
bydifferentmicrostructures(trichomes,cuticularfoldsandwaxcrystals),together
with the hydrophobic properties of the epicuticular wax. Hydrophobicity of
epicuticular wax and the microstructures can efficiently reduce the deposition
andretentionofspraydropletsbyincreasingcontactanglesandreducingcontact
areawithplantleafsurface(4,5). Greenhousegrownseedlingsandyoungplants
havebeenthemajortargetsinearlierstudies. Surfacepropertiesandplantcanopy
structures change dramatically as plants grow, and ultimately affect the quantity
ofspraydepositedandredistributedovertheentireplantcanopy(6,7).
In this paper, we present the results of our investigations on the effect of
the physicochemical properties of fungicides on retention by seedling wheat
plants,andthedevelopmentandvalidationofaQSARmodeltopredictfungicide
retention. The impact of three epoxiconazole formulations on retention and
the relationship to fungicidal activity were also investigated. The relationship
betweenretentionofspraydropletsandthewettingcharacteristicsoftargetplants
and their canopy structure, as well as the physicochemical properties of spray
liquids,arereviewedbasedonthepublishedliterature.

Effect of Plant Surface Characteristics and Canopy Structures
on Spray Retention

ThePlantCuticleandLeafWettability
Allaerialsurfacesofterrestrialplantsarecoveredbyacuticle,whichserves
astheinterfaceofplantstotheirabovegroundenvironment. Theprimaryfunction
ofthecuticleistopreventwaterlossfromplantssothatphysiologicalprocesses
can proceed under water-limiting conditions. In addition, the cuticle acts as an
effectivebarriertotheentryofxenobioticsandmicroorganismsintotheplants.
Theplantcuticleconsistsoftwomajorcomponents: cutinandwaxes. Cutin
isapolymercomplexconsistingofmanylong-chainfattyacidsthatareattachedto
oneanotherbyesterlinkages,whichcreatearigidthree-dimensionalnetwork(8).
2
In Retention, Uptake, and Translocation of Agrochemicals in Plants; Satchivi, et al.;