Education
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Education
7>t- ,'-t^,U 7 ã n*'e I99?. Volunc ll:384 393 weedTeclìnology. i a L V Education í. ] ,' t. i' .l , , r ; ll l r : i , , .' . . _ l : ì i ;r' ' Classlffcationof llerbicides by Site ôf Action for Weed Resistance ManagementStrategies' E. JAMESRETZINGER,JR andCAROL MALLORY-SMITH' of heÍbicidessccordinglo their sitesof âction wâs developedto help abstract: A classification of herbicidesas â tooì iD cropproductionto delaythe selectionof helbicide_ maintainthe usefulness *""a". The classificationincludes a numbering systemfor the site of action' úe chemical t"rir"" pâckage fo,nifv, u"a *r..omm"n rìâmeof the herbicide.The United Stâtesof Americatradenameand mixêsalsosÍe inolldêd. sytthase;HRAC' Herbìcide synthase;AHAS, acetohydroxyacid Abbreviations: ALS, acetolactate ResistanceAction CorÌìmittee. L.), sugaÍ beet (Betarulgaris L.), and rough and Íìne INTRODUCTION ' Coppersalts,iron sulfate,andsuÌfuricacidwereused The incteaseduse of herbicìdesfor weed controì led \_--, as herbicidesas eally as 1896to control broâdleafweeds ro the selectionof heíbicide-resistant weeds.Herbicide in cereals.but it was the discoveryof the phenoxyher- resistanceis the heritabÌeability of a weedbiotype to bicidesthât usheredin Ìhe modemageofchemicalweed survivean herbicidetreatment to whichtheoriginalpopconrrol(Robbinset â1.1952).In thelate 1930sandearÌy ülâtionwâs susceptible. In 1968,RyanÍìIst reportedheÍ1940s,hundredsof úousandsof hectareswerc trcaled bicide resistance,in commonSroundsel(^S?teciotú184,'with sulfuricacid;however,in 1949in Canadâalone3 3 ir L.) resistantto simazine(Ryan 1970) By 1990,resismiÌlion h€ctares(8.2 milìion acres)werc treatedwith tance had been reportedto most herbicidechemical 2.4-IJ.ChemicalnamesofheÍbicidesmcntionedaregivclassesandin 99 weedspecies(Hoh andLeBaron1990). en in an Appendix.Althoughno accüaterecordof arcas weedsprompteduni AwaÍenessof herbicìde-resistant treâtedwith 2.4-D is available,9 l million kg werc man- versity and agro-chemical personnelto developguide' ufacturedin úe U.S. in 1949and the averageÍale was growe$ on how to minimizethe risks to educate lines Fobably lessthân0.5 kg. weeds.rTheseguidelines of seìectingherbicide-resistant Today, high yield agriculture rcÌies on herbicidesas include similar recommendations:(a) Scout fields pdor an integÌal part of weed conüol placlices that pÍoduces to the application of any herbicideto detemine the spemore on fewe. hectares(LeBaÌon 1990).osteen and cies and if economiclevelsjustify an herbicideapPliSzmedraí1989)discussedúe shiftsirl herbicideusage practices' cation.(b) Use altemativeweedmanagement from the phenoxy heÈicides to h€rbicidessuch as thc such as mechanicâlcullivaÌion,detayedpìanting.and dinitroanilines,and triazines The amides.carbamates, weed-freecrop seeds.(c) Rotatecropswith an accomv introductionin 1982of the herbicidesthat inhibit acepanying rotation of herbicidesto avoid usìng herbicides tolacÌatesynthase(ALS), also calÌedacetohydroxyacid with the samesite of âction on the samefield. (d) Limit synúase (AHAS), c.eated ânother shift. These broadthe number of applicationsof a single herbicide or herspeclrum classesof herbicides are now labeled for all bicideswiú the sâmesite of actionin a singlegrcwing Ínajor conìmodities,including cereals,soybean(Glycine season.(e) Use nxxturesol sequentialtreatmentsof her_ max L.), íce (Oryu satfuaL.), com (Zeanots L.), col' bicides that eachcontrol the weedsin question,but have ton (Gossypiutuhirsutun L.), pè Í\t l (Arachìt hypoSítea a different site of action.(f) Scoutfields after application --iÃ!Eiiãro. rom Novenb€r 1ee6, and in relised outti"urion.rpÌil23, to detectweed escapesor shifts. Il a potentially resistant r8. 199ó. weed or weed population has been detected,use avail_ , AnericanCymmid, weÍ DesMoin$, lA SeniorField ^eric!]I!Ìií, 5026óândAssislanlPrôf$sor,CropandSoil Science'OÈgo! StaleUniv€tsnv.Corlallis,oR 9?33l respetiveLt. --aifiãF"i"ne 384 so"i"rv ot .qneilcaNewsletE.,1995.vr'ssA, 23i21-23 WEED ]'ECt{NOLOOY (Biiger and Sandman able control meÍhodsto avoid seeddepositionin the cide sitesof actionand iesistance et â1. lg93; Dodge Devine field. (g) Clealì equipmenÍbefore leaving fields infested 1989;Caseleyet â1. 19911 1989rPowlesand Holtum 1994) to haveÍesistantweêds. with or suspected to families Shaoer(1995)reviewedthe niÍìeherbicide which resistancehâ6 devclopedwotld-wide.At Ìeâst hE6ULÍ6 ANO DISGÚ6SION to herbicideshavebeen of resistance tbÌeemechanisms irÌ Table1. The is presented The WSSA clâ$sificâtion observed in plâíts. These are alteled sites of action, site ol numbér, includes úe cÌâssificâtion tabÌe Sroup of theherbicide,ând in úe râteof detoxi6câtìon changes U S trade ingredient, family, active action, chemicâl modificationsin the uptake and translocationof the heraddition, the name, and packagemix trade names. In bicide. designationfor úe gÌoup is included KnowingtlÌe site of actionis key to planningan her- HRAC alphabetic parenthesis under the wSsA classificationgroup in biciderotationstrâtegyto reducethe potentialfor selecI lists U.S. tradenamesfor package Appendix in Mân- numbeÍ tion of Íesistan!weeds.In 1991,weedscientists to statndardize mix products.The sectionnumbet in Appendix I refe$ itoba.Cânada.developeda classincation the WssA-approved conÌnon name oi the hetbicide the hetbicidegroups.This clâssiflcationwas first pub- to as it occurs in Table I and the packageÍúx paÍners guide in 1992 lishedin the provincerecomÌnendation Aooendix 2 containsthe herbicide'schemicalnameas (Anonymous1992).The guidelistedeachherbicide,the reúrreO in the Chemicat Absracts Servìce (Atuens group(1,2, 3, etc.),âlonglvift weedspecicswiú pop' to tÌÌaÌ group,âncl 1994), ulationsthat haveevolvedresistance A review of the Australian(GiÌl et al. 1994) and for delayingthe onsetof we€dresisa recoÌnmendation WSSA systemsshowsthat the AustraÌiansyslemtencls tance.Beginningin June 1994,labelsof all herbicides place more herbicideswithin a gÍoup (e.9., Ps II inregisteredin Australiawere requiÍedto identify which to \-heÍbicide gtoupor grcupsthe prcductbelonged.Hetbi- hibitors, triazinesalong with the benzothiadiazoles), whereasthe WSSAsysleú plâcesúese two PSII inllibcideswete groupedA, B, c, etc.,by modeof actìonto for poisons itors in sepaÍategroups. Separatingthese groups more avoid confusionwith numericdesignations closelyreflectsobservedresultsindicatingbentazoncan aÌreadyusedin Australia(CiIl et aÌ. 1994)to bercsislaiìtÍo atrazine(Gronconúolweedssuspected wald 1994). PROCEDURES The classificationcould have wider utility with the At the 1995WeedScienceSocietyof AmeÍicameea inclusion of the following herbisidescurÌentÌy rcgist€red ComÍÌútteecommissioned in EuroperGroup 12 additions:diflufenican,flurochloring, ttÌe HerbicideResistance idone, and flurtamone,and Group 15 additions: mefensystem,draw' the draftingof an heÍbicideclassincâdon ing fÍom tìe Canadianaod Australian systems.The clâs- acel and BAY FOE 5043.Herbicidesin Groups27 and 28 are cunentlyutilizedin Europebut not registeredin sincationwas reviewedby weed scientistsin the U.S , registered with a new mode Canada,and Europe,and was developediviú the co- the U.S.The nextherbicides of actionshouldstaÍ wilh Group29. opeÉtion of the Herbicide ResistanceAcdon commi$ee is the ability of a biotype Targetsite cÌoss-resistance (HRAC).HRAC wâs formedin 1989by technicalrePto herbicides from different chemical to be rcsistant indusüy to deveÌop from the agro-chenücal resentatives site of actionand is úe Íesult a cohesivemanagementplan to adúess herbicideresis- classesbut willÌ Ìhe saDìe system of a changein the targetsite. Wiúin heÍbicide Group 2, . ,ance.HRAC supportstheherbicideclassification (R. R úe inhibitorsof ALS/AHAS, variablelevelsof c.ossresistance ad&ess herbicide as one meansto In addition,HRAC Êsistance lìave been reportedamong úe sulfonylureas, Schmidt,personalcoÍnmunicâlion). imidazolinones, and pyribenzoates, systemfor use triazolopyrimidine is developingan hcrbicideclassiÍìcation (Bumet et al. et â1.1994; dine thiobenzoates 1994; Saari HRAC systems differ in the The wsSA and ir Europea conservalive 1995). This classilìcalion takes ShaÌÌer cloup designation.Groupsin úe wsSA ând the HRAC by numbersand letteÍs,respec- approachin groupingall iúibitors of ALS/AHAS within systemsâre designâted one group. úvely. is úe ability of a bioherNonlaÌget site cross-resistance No attemptwâs madeto cile referenceslor evety bicide and its site of âction since much of it is common type to be rcsistant to herbicideswiú different target . knowledge and the rcferences would be exìaustive. sites. Wild oat (Atena fatua L.) resistant to lhe prcemersenceherbicide ariallateand rcsistant to úe herbiHowever. úere are several teviews availabÌeon herbivolünê I l. Issüe2 (^pril June)199? 385 BY OF HERBICTDES RETZINGERAND M U-oRY_SMITH: CI-ASSIFIC^TION STRÀTEGILS SÍIE OF ACnON FOR WEED RFSISTANCEMANÀOEMENT âccoÌdingto prìmrv sit€ofãdion' Iarl, Ì, He.bìcideclâssiôcation GÍoup I,IRAC Inhibitois ol acetYlCoA 1 2 (B) ^ryloxyphenoxtPopic lnhibitÕ* ot scetoìâctàlc sy has ALs and ãÌso, call€drcê@hvdmrv,cio MON 12000 Bask(2) MON 37500 AC 299.263 Lìghtning^ m'x) Gold only ãs Páckage PyrimidiÍyìthiobcnzoe MicÍotubuleassenblYin DCPA (o) lite indolcâc€lic acid) 2.4 D 2!-DB MCPA MCPB 5 (c,) 386 lnhibitionoi phorósynlhê_ E!ik' VolulÌe ll, hsu€ 2 (Apnl-Jüne)199? WEEDTECHNOI-OGY TiRAC Hylar X 6 (c,) lúibÍion of Photosytlhe_ slhe snediflè!€ntbihding Inhibitionof photosvnücsane snediffelentbindjíg Inhibirion of liPid sYÍthc si*not ACCase innibnion EPTC (z) I (c) (Hl |l l2 (F,) at .arorenoidhiosYntbesis srcp(PDsl l3 Vt,t lnhibitio. of alì Bleacbing: Irhibitio! ol Protopo+hyË íE) (ì) cc^-248?5? l5 vollde I l/ Issue2 (APÍil-hnd 1997 Hdesí, Sutpassì,Topnoìch" 25 Secrior 38? ' AY SnE OF ACTION FOR WEID RESISTANCEMANAGEMENI STR'ATEGIES REÌZINCER AND MALLORY sMtÌH: CI-\SSIIICATION OF HERBICIDES HRAC ;õ u.s, irâde nôFe sne oÍ 'dion chcmicallãmiì' Pâckagehix u s mde lame Úilh Acüve insredienr Oxv.cetânides ' natúpâmide mencúacel BÂY FOE 5M] Devn.ol! elhofümesâte Noíron" {N) Opmosehicâls ' \z) DSMA MSM l8 (l) InhibitionDg! (dihvdloP slep) tcroalesYnthase Cdbânab l9 lohibÍioÍ of iidoleacêric PhÌhálanst€ 20 lrnlblrro[ gl..lltjlo!ç rtn" Nirúlô 2l (L) Inhibitionofcèll wátl.yn' tftesissireB I'elecÌrond! Photosysrcn B.í2àfride lDhibnionof úiiosis carbanares Uncouplrng Mcmbrâned^rupto6 Ditritophenol di.osb AÌyladinopopionicacid ilnpÌoP'retbvl None Tca 22 23 (K,) t'-ú4) BiPvlidvìluns dlquál (z) (N) tz) 28 (FJ Triketone Inhibitionol4_hydrcxy phenylpyruvate'dioxtgen_Isoxa@lc PY@olc de (4-HPPD) .BASF " Afreri.ãn cyanafrid CFMC 388 Volune tl, Issüe2 (Ap.il-tune) 1997 WEED1ECHNOLOCY cidê difenzoquat has bee'l documented ]n numerous fioldsin ^lberta,Canada(O'Donovarìet 41 1994)These two different herbicide groups are in Group 8 (unkrown site of action) but almost certainly do no: havedìe same site of action (B6ger ând Sândmân1989).Furúer studies bv Blackshawet al. (1996)haveiídicatedthls t€sistant wild oat is mote susceptibÌeto applications of EPTC, wild oat. thanis the susceFtible anoúer thiocaÍbamate, âs re_ be reported FuÍther exceptionsto úe tule will seaÍchcontinues.To note all exceptionsin úis chaÍt will which is to belie the true purposeof this classjficâtion, of helbicides úe classifrcation üovide a framework for üy úeir site of action.The rotationof herbicideswith lheprevention s;lcsof âctionwill noÌgììârsnlee diflerent resistance asdemMetabolism_based of weedresistance. (Lolium ìgidum C^adin) ií onstrâtedby rigid ryegrass Austrâliacrossesseverâlherbìcidegroupslistèdin úis (Buntotèt â1.1994), ,JlassiÍìcation is but one aid in the mânagement This clâssification The moredive$ity in toolsused of heÍbicideÍesistance. to conrol weeds,úe less Íisk ol selectingresistant 'ceds- ACKNOWLEDGMÊNTS The authorsacknowledgeall of úe weed scientists DaÌeShanelAmerican who reviewedthe classilìcation, RobertSchmìdt,BâyCyanâmidfoÍ vâluableâssistânce, er AG Germany,for inputfrom the HerbicideResistance Action Committee, and Wilüam AÌÌÍens, NoaÍh Dakota in preparing for providin8assistance S(rtelJniversiÌy. manuscíipt. this 199? volümeÌ1. Issúe2 (APril-June) CITED LITERATURE lL;Weed ?lh ed ChanPaign, Ahrcrs,W H.. ed. 1994.HerbicideHandbook. sciênceSo.ietvof amenca l52 P Anonynou' lÔo2. lcal Cuidero C'op Pmrectioí CámÚ MB: Mrnituba Deo.rrnebtof AsÍi(ullue l88 P Blactjiw. R. E., t. r o Donoran M P Sfma. K N Hdret ríJ D Mrlrìcè, 1996 Rèstõn3eÒr tri lâtc ÈÉidftt wild o.t (-4!"' /'r"d) lÕ Àlbddúvè heiblcid;í WéedT.chnol.l0r?5E-2ó2 Bôser. P H, ând C, Sahdnsn, eds. 1989 Tüeet Silês of tl€rbicidê A'liÓn' Bcá Raton,FLrCRC Pre$ 295 P. Bum.r. M WM., Q. Hd. J A M Hokutr,ãndS B Powles 1994Re'islance lo nioe herbicide(lã$e. rn a populdlionoÍ risid 4eglas ír'ri!ã ri3 ,d!ú). We€dSci.42i369-3?7andR K Àtlon,€ds l99l HerbicideResis_ CNley. J, C., C, W Cussans, ranc. in w*ds ând Crcts. Oxford: Butlerwoíì 513 P. Devjnú,M. D.. S. o. Dukc.and C- Fcdtkc 1993 Phvsiologyof Hèibicide AôlióÍ, Êoglesood Clirfs, NJ: Prcntice Hâil. 'l4l pDods.. A, D., ú. 1989.Húbicid.s andPlantMetabolismSocielvofExPerlnenúl Biolosy.Senioú Scries38 Canbidee Cobridge Unive6nv a Ref€Énce Cill, G., J. Holnes, ând R. Kelly. 1994 HeÌbicideR.sislaoce. Manual.Depanneniof AsriclltuE WestemAuslralia Misceuaneous Pubkaüon 16194.0.3-7. coíw!ìd, J. C. t99c. tiesnrrncelo nhorostqedll inhibhlnShe'hiridc' Ì, s. B. loqles and J.À.M nohtn, eds HeÌblcideResi$lánc ii Planc' BiotoÊv.ndÀiochófihrv. Èúa R!toí, FL CRC Pt.s p )t-ó0 Holr.,.s.;;dH.M.LcBmn. laooslEtuíìcinc.ríddh{lbullÒnôíhêtblcldo W€edTechnol..l:l4l-1,19. Ésisrance. LêBen, ll. M lS9O.Weedsciencein rhê 1990s:Pil! it be forwâÍdor in wad Technol.4:671-689, @verse? O Donován.,. T, M. P ShÊma.K. N. Ha.kei D. Maurìcc,M N Baig dnd R. !. Blxckslì.w.1994.wild o.r ('4fuíalar!/) popll ionsÈshmnrto w€ed sci.42:195-199 trial!.t€arealsoEsislânttô difenzoquat. usolrendsand OsÈen,C, D. and P L Sznedü, 1989.ABriclltuialPesticide policy issues.USDA. Asricllllral Ë.onomic Repon 622 p. in Plan*. Powis. S. B. andr.^.M. rbXln, eds 1994 HeÌòicideResistânce BiolosyâÍd Bioch€misry.BocaRaron,FL: CRC Prcss.353 p Roübnr. W W. A. S. Crafb. and R. N. Raynoi 1952 WeêdConüol.New York McCÍaw-HiU.503p. Ryúr, C. E 1970.ResÌlanceoi codmon eoündsello sinüin€ ândâtrâzine WeedSci. 18:614616. late S*ri- L. L..J. C. Cotleman,ândD.C. Thill. I 994.Resiíancero ac€tÔlâc S B PowlesandJ.ÀM Holtufr.eds. syrú6€ inhibninenerbicid€s.1" in Plaits.BioloevandBiochenisúv BocaRaton, HerhicìdeResisrance FL: CRC Pr€ss.p. l4l-170. ofÊshlance: thcir D. L. 1995.Studieson ncchmisns andCenetics Shanqr, contribuiion ro herblcide rcsisranc€nanaeen€nt PÌúc Bíi8lìton CÍop Pot. Coni 2:53? 545 389 BY SrÍE OF ACÍON FOR \Ã'EEDRESISTANCEMANAGEÌ\'ENT STR-\TECIES RE'IZINCERAND MÂLI-oRY-SMITÌI: Ci-ASSIFICAIoN OF HËRBICIDES ÁplendiÌ ./. PackaÊe,nìxtures listed bv útivê ingiedienr MCPA(4) MCPA(4) MCPA(4) zt,D (4) Tiller BASF Nnúa[n i3) LiBhtning 2,4D (4) FMC 2 . 1 . D( 4 ) MCPA(4) MCPA(4) .-,.2 t3 MCPA (4) Tilìe. 2,4-D(4) 2A-D(4) 2A-D(4J ganvel520 BASF BASF 2.4 D (4) 15 390 2A-D (4) 2.+D (4) Votumell, hsuc2 (April-June) 1997 WEÊDTECHNOLOCY 2A-D(4) CIBA CIBA CIBÁ CIBÀ Laddots-12 EitrazineII BASF BASF BASF BÁSF MCIA (.1) 2.4-D(4) BASF BASF EPTC 21 CIBÀ CIBA CIBA BASF 199? voluÍe 11,ksue2 (APril-Jlne) 391 - BY SITE OF ÁCIlON FOR WEED RESISTANCEMANACEMENÌ STMTEGIÈS RETANGER AND MT\LLORY SMITIT:CLASSIFICATIONOF HERBICiDES Árpddú 2, Alphabetical list of chenical .a]É (2,.4iichìorcPhênaxy)acêtic.cid 2.4-D rcid 4.r2.4.dichlorcphenoxr)buranoic 2,4.DD Ì_'rethvlerhvl)_5_oxo_ (iJ.2-t4,s-dihydrc-4'nerhy!'l_{ AC 263,222 lic lfi .imrddol-2 yll_!merhy!3_pvridinecsbo\J AC 299.263 di noseb dimethónanid l ncrhvlelh'l!5 oro (l)-2 14,5-d rhydrc-4-mêúyl_4_i pvídinecaF I d-imidazol2.yll-5ímerhoxymerhvll3 2-chb;-N-(erhoxynethyl)_|r''(2{üvt'GnethvlPhen- EPIC 5-i2-chloo-4'(rifiúoonethyl)phenoivl-2_nitobenrcic 2,chìoro-,v-(2.6-dieÌhylph.nyl)-lv-(nelhorvne_ &{lnyl t'-(l-nethybtnyl) ç(methvlúio)_13.5 tnâ_ lt- l.2,41riabl3-ónine mcthylÍ(4-aúinopknyl,sulÍonyUc*bãmrk r l c r h y l e r h ) l lL5l Ú t d n ' . 2 4 ' Ò . c h l o r o 'ê/ vr h y l - r ' ú :m 3.4_thladl BÀYFOE5043 4rnuorc-NlsopÌopyl-2-(5ìnduoóneúvll ael2-yloxy)acetânilide N-buryl,Nrihy!'2,ó-dinÍro-41lÍifuloódeüvll_ 2'tÍt(l(4.ó-dìdethyoxy'2.pynúidinvl)ani.olcebóítll ácid âÍinolsuÌfonyUmethyllbenzoic O.O-bn(l-nerhylcrhyl)S [2_Í(phenylsullõn_ yl)arinolethrÌlphosphorodiÌhioaÈ b€nólhildiuin_4{31t' 3-il neúylerhyl)-(lrD-2,1,3 reíoxapop Rúãzifor-P o^!Ìo.oornoicacid N.(2.;.li|ììorcphenrlfs_mdh) Il I .2 4ìháelol ' 5' ,lplmldlíe.2aulrônsnido núniclorrc t2{hloó'4'lluoro-5'(1,3.4,5,6,?_hexúvdo_1.3'dioxoeid 2lÌ-isoindol-2-yl)phenoxylacetìc t . {4-chloo- 3-[( 2.2,],l.:i_Pcntal uooptôpox, )nethv Iì í upoÍaú phenyll_5_rhen]| IH_' !.'lrÍiarole_Jcaroo\!irdc N,i.dimdhlIN:LLuifluoíome'hJIrphenvllúEa fluodeuÌoì 'ìutucblolidon€ 3 chloro-+(chlorondhvl)-l'[3-(rifluoronerhvì) pnenyu2 pYrolidinon€ 2_pyndi.yl)orvÌãceric t(4"adìÍo-3.5'dichlorc_6_lìüorc 3.5-dibroEo-4'hydrcxyb.nzonnÍile lr'-Outoxym€thyl)-2-chloro-N12,6_dieôylphen S-eú)l bk(2 6crh)Ìprcprlrübãmorhioatê | (,1-dcrhoxÌô-meúyl lÍrazin2_yl)_lJ2rl l,3rnfruo' ÍoprcpyU-phenYkuìtonYl I uFa hhydÌo I oxô lH.3lr' merhyltt2{hloÍo.J.nuoo.5_lit I l,3.4lthiadiazoÌo{3.4-alPyriddin'l_ylidene) adìnoìphenylÌhiolacerare 2-tltl(4-chlorc-ó-merhoxy_2_pyrinidi_ acid nyl)âminÕlcdbonyUaninohulfonyllbenzoic l-netbrlethylI-chlorophe.ylcarbamate l,S,5rriuin_2 2{hloro'N It(4rnelhoxy-ó-nerbyf yl)anioolcdboiyllbcnzenesuìlonmide eroll) I nelìyÌ-4'(l-deúylethyD'2 l(2'merhylphen yl)merhoxyl'Tixabicyclo[2.2. llheptanê (8,4)-(r)-2{l lÍ(3{hloro-2-prcp€nyl)ôxylini'ol pÌopyll-5-[2-(3eúyhboi)prcprlÌ_3-hydorv'2'cv' 'iT*''" dinclhyl3-isoxdolidi_ 2-t(2-chloophenrl)netnyll-4,4 DCPA {1)-2-(2,4-dichlorophenoxy)prcpanoicacid (a)-2-l+(2,4-dichlorcphdoxy)phenort]pÍopanoic (t)-5'(6eÌhylamino)'2phehyl-4-[3_(tdíuoom* thyl)phenrll3(2,Ií)-r!dnone iíuoronethyl)phenoxyì'rv"(nerhvku'_ 5 J2-cnloo-4-(tr íonyì)-2-nnóbenzâmide acid 2-aninó-4-(hydroxynethyìphosphinyl)buranoic Nlphosphononethrl)Clycine 3,5ìria' 3-cyclohexyl-ó-(din€rhylanirìo)_l{Ì€íryl_1 zine-2.4(ll/3Ír-dione (:)-2-t.l.l-dibydro-4{ìeúyl'4-(l-mcthylethyì)-5_oxo_ acid 2-ylÌ-4(ãnd5)-melhrlbenzoic l,Y-imidazol (3r2) (r) 2 [.15-dihydro-4-rethyl4-( I'deüylethyl)'5_oxo' UJ iúid.zol-2-yÌl 3 Pyijdinccârbotyli.rcid -neIhtìeúyl)_5_oxo_ tt2-t4.5-dihydro-4-meúy1.1.(l acid inidüol2-lll 3-quinolinecaÌboxylic IÍl l-nelhylerhyl)_5_oxo_ 2-[4,5dihydro-4'úeúyl-4-( jc acid imidazol-2yìl-5-clbyl'JpyrìdinecaÍboxyl ile 4-hydrcxy-1.5'diiodobenzoíift dinnGMlVìiprcpylbonzena4-(l-meúylelhyD'2.6 À Í3.(l<tbyl-l'meúy!pÍopyll-s-isoiuolylJ-2,6-dime 2 py.idyloxy) 2 p,opyDyl-(A)-2-[4-(5-cnìorc-3-rlnorc acid 3.6-dichloro-z{yrdinecarborylic 1,3,5'triúìn-2-yllaninol_ 2-l{4-chloo-6-(eúylam'no)2-ncúylpúpan€nitriìe s ethyl cycloh4ylcthylc.rbamorhioat€ benz€nediceboiylâE dimethyl2,3,5,61€trachloó-1,4 acld disodiumsaltof nerhaúedsonic 2.2-dichloop.opanôic acid eìhyl[]-ft (pheÍylâmino)cübonylÌoÌylphenyll.úbamte 3,6-dichloro-2-nethoxybenzoicacid (1)-2-t4't(6{hlorc'2_benzoxuoltl)oxvlph€íoxrl propa.oic acid 'Ì4-I 15-(aií úobhethy nvlloxvjphci D_2-pvridì {À)-2 nunehúÌem 5-brono-6-methyl-l-(l-methyltópvl)2,4(lIt 3r)pyrìfr i'litcdionê z-brono 3.3-dimeúyliv_(l nethyl_l_Phenyl- ccA-152005 rv-(2,.1 diíluo,ophenrl)-2{3-(ttidúoromerhvl)phenox!J_ 3_Pyridinêcarboxâhide initiophcnól 2(I . nethylpÍôpyll-4.6-d 2-cnbrc-N(2,4_dimethvl'31hicnvl)',!_(2-nethoxv_Ìmêthylerhyl)'âcêìamide bcnaneJcer3m,óe N,|';-dinerhyl-d-phcn)ì iun clpyrazinediium 6,7-dihydodipyridoll.2.o:2'.1' ,{L(3,4ìichlooph€nyl),{,{_dideúvluÉa S{rhyl dipropylcaÌbamorhioak dini!rc'4ítrifruo N{rhyl-À-L2.melhyl-2-prcpenvlr'2.6 rohethyl)ber*íamiue 1,3.5ìdâzin_2_ 2-ÍltJ[+erhoxy-6-(reúylanino)ylhriiolcdbonylhniroìsnlforyllbenzoic a.id (l:)-2'erhoxy-2,3'dihydro 3,3-direüyls-benzofutanvl MCPB MON 12000 MSMA merolachlôr meÌdbuzin íJ)-2-ethoxyì-nelnyl-2ox@lhyls-[2{hlorc 4 (tri 0uorcnerhyì)phenoxyl'2-nittubêhzoale ÀL(3,4-dichloóphenyl)-Ir'-deúoxy-lv-m€thyhrea (4 chloo-2-nethylphenoxy)aceric &id acid 4-{,L€nlorc-2 methylpheÍoxy)butlnoic mthyì 5-tl(4.ó-dinôrhÕry-2-py.ihidinyl)âúiiolcdbonyladinosulfonyU-3-chlócl_neú_ y! l.It'trrazole-4-caÍbotylâlc acid sall ol mctbylaBonic monosodium ( :t !214-chloro-2-ne lhylphcnoxy )pó pâíoicâcid 2í2'benzothieol yloÍy)-N ! henylaceknide neüyl-1,2,+ôxâdiazolidire_ 2-(3,4-dichlorcphcDyl)-4 3.5'diôn€ 2-chloro-N-(2-e!h!l-6-nelhylphenyl)-d-(2-neúoxy-l neúYlethyl)ac€tmide 4Ìnino-ó-(l,l-dinerhyleúyD_3-(neúyllhio)_1,2,4_ riain,5(4Ir-oie 1,2-diúethyl3,5-diphenyl llt-pymliüD 392 volunc ll, lssue2 (April-June)199? WEEDTF.CHNOLOCY 22 tÍli(4 nerhoxy-6-mêthyl-l,r,5rriâ,in âcid vl)anìnolcdbonylhÍioolsulfonvllb€nzoic S-eúyl hcxúydD-llt'âzepine-l câibothioate N,{-dierfiyl-2-(l-naphthale.yloxy)propanamtd€ laúino).dbÒivllbe.mic acid 2.1(1'naphtbaleny 2- IL(4,ô-Lrhèüory2.PyÌimiJinyì) NN dlnerhrl_l aminoicdbon)llromolsulÍonyll pyridinc.srbohmid. 4-chlorc's'(déthyìami.o)_2_(3_(tiifruorcmc_ úyl)ph.nyl) 3(2s)_Prridszinône ltdroíopylamrnoIS,5.dinrrcbenÈíesulfonamide 3-Í2,4d;hÌôÍo 5 r l-neúykúor y rphenvlltl l.l di_ íethyleúyl)-1.3,4-oxadiDal2_(3lr-one 2-chlorc-l-í3ethorv_4_nitrophenoxv)_4_(ÌníuoÓdê- 2.tLtl(+meúo{y6 ncúyl 1.1.5kiazin_2vlì acrd meúylâminolcáóonyllâninolsultonvUb€nzoic acid 1(3,5,6-rrichlorc-2-pyridinyl)oxvlacetic 2.6-dinit.o-rv,N-diprcpyl-4_(lrjfluorone:-lLltl4.(dihcthylmino' 6 (11.2 trinrcrcêth.\-11 . inolcüboíyìl 0m'íoFUrróivrI 1,1,5.úìazin-2-yllfl s-popyl dipÌopYlcarbanoihioaie ion l lldiúethyl-,1,4'-bipyridinium 5 propylburtlerhylcúbamo'hiÕate !(Ì eúyloÍopylIl.4-dimeúy12,ódinitobcnanamine ncrbylphen' 3-ÍúnErlìoxycabonll)âdinoiphcnll(3 {id 4 aniÍo-:1,5,6-trichlorc-2-pyndintrrboxrlic 2 Íllt[4,6'bh(dif,uÒbdetboxy)-2-pyrihidi_ ac'd nvUaninol.arbonylhnìiokullonyllbéÍzoic inuoíiméthvl).1,3.bèiì2.4'dinitio'M,M'dipÌõptl-ó"(|r 6rndhory Mt'rbk( ì -rérhylcrhrl)-1,3.5fÍìâzirc_2-4úiuinc14,{lbis(l merb}lcrhyl)-ó l,nedìylrhio)-1.3,5 Ì. l-dnÌ€ìbrl-2.prcPyoyl)benzôúide 3.5-dichlorc{N2-chìoro-d'('-meúylethyl)-rv-Pbenyleotmide À-(3.4-di.hÌôroplÌ.nyl)pro@óatnid€ di_ 6'ct orc-rv,N'-bis(lmethylcthyl)-1,3,5_!dazite_23 \- l-n€ihyleúll phenylcãrbada.e (2.3-dichlôrôpheoyl)[,!-dihethyl 5 ll(4-nethylphe'_ y!)sulfonylloxyl-llr'pyrseì-4-yllôethanone 2-py.inidinrl)thioÌbenrcic 2-chlorcó-Í(4.6-dim€thoxy cübonô0'(6 chloÌo-3-phèíyl-4-pyf,duinyl)s-@lyl 3,? dichloo-8'quinoliíe.aóoxylicdcid (,{)-2Ia [(ó{hÌorô-2-q!iioxaìinyì) acid oxrlphenoxylpropnnóic N{t(4.6-dimeúoxy-2!triridinyÌ)aminolcaibonylì_3(erhykullonyl)-2-pyridinesulfonanide 2-tl-(erhoxyimino)butyll'5 12(eúyÌhio)popyll_3_hy_ droxy-2crcìohexen-l-one .{-(2-methylcyclohexyl)-rVLphenyluea diaoite 6 chloo-N,x'-diethyll,:1,5-rriazine'2,4 N-[2,4-dichloÌo'5'14-(diflüorcnethyl)-4,5-dihydro-3_ n.thy!5-oxcllr-1,2,4rÌiazo!l-yll-phüyllnetha.esülfoÍdide 2 [[[[(4,6 direúyl'2'pyÌinnìdinyl) miDolcúbonyllaninolsüllo.yllbenzoic a.id TCA X'15 (l,t-dineúyletbyl)l,3,4thiadiúô12 yll_lYM_di E,3tt' 5-chloo-3-(r,l dineúylerhyl)'6nell'ryr2,4(t 3 [[[[(4-neúoxy-6-methyl-1,3,5'üidin-2y!)minolarbonyllffi inolsulfoíyll-2-úioph.húúJ,t(4{hloúphenyl)nelbylidieúylcârbânorhioate 2-( l(€thoxy'dino)propyll'3-hydtury-5-(3í,6rdneüylphdyl)'2{yclohexên- l -oie 5'(2,3,3tichloro'2-PlopenyÌ)bis(l -nethyls 1.3,5'lda. 2(2-chlo!ôeúoxy),ry-[(4'neúoxy-6-nelhyf ziÍ-2-yl)anino jc&bonyll-benen*ulfonamide voìuoe I I, lssue2 rAfil-Juneì 1997 393 .