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    Synergistic Herbicidal Composition Containing Flur

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    vtkiet2003

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    © All Rights Reserved
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    «2 United States Patent Mann et al. US 8,420,571 B2 Apr. 16,2013 (10) Patent No.t (4s) Date of Patent: (58) SYNERGISTIC HERBICIDAL COMPOSITION CONTAINING FLUROXYPYR AND CYHALOFOR, METAMIFOP OR PROFOXYDIM. (75) loveotors: Richard K. Mann, rank, IN (US): Monte R, Weimer, Pitabor, IN (US): Andrea Christine MeVeigh-Nekon, Indianpotis IN (US) (73) Assignee: Dow AgroSetences, LLC, Indianapolis, IN(US) () Notice: Subject to any diselaimer, the term ofthis patent is extended or adjusted under 35, U.S.C. 1540) by Odays. (21) Appl.Nos 129913,285 (22) Filed: Oet.27, 2010 (6) Prior Publication Data US 2011/0008181 Al Apr. 28, 2011 Related US. Application Data (60) Provisional application No, 61/255, 685, fied on Oct. 28,2008, (5) mec AOIN 4340 (2) Us.c. usec (58) Field of Classification Search ‘See application file for complete search history. (2006.01) 04/130 ‘None 66) References Cited POREIGN PATENT DOCUMENTS: ox lotowss7 A 2007 roy ToLSi0 104 A 9.2000 oN loisiolog + 92009 roy oLSos875 a 122000 ox Lotgeas7 Aa Wo wosTioTI0 AL 31997 WO Woosna7Mz AL 2003 (OTHER PUBLICATIONS, US. Appl No, 12913002; Synergistic Hebicidal Composition Conaning Furoxypyr and Pesoxslam, Halosaliron Methyl Inazamos or Iza led Oct. 2, 2005 Inventors Richard K, “Mana, Monte K. Weimer, AndieaC, MeVeigh-Neson, an Andrew Todd Eis US. Appl No, 12913152; Synergistic Hebicidal Composition Conaning Farosyp and Quincorc lad Oct. 7, 2010: inen- tors Richard K. Mana and Andrea C. MVlgh-Nelon “McCullough ea. "Fuoxypyr Compatibility with Fenosaprop for Smooth rabarass and White Clover Control in Tal Fessue" pid Turfgrass Science, XP 055022757 20), Metlioy et al, “Trlopyr Safes the Use of Fhuvifop and Fenoxapeop on Zoysigrss While Maintaining Bermudagras Sup- pression” XP 055022791 (2006). Dovoh & a, “Tilopy Enhances Metamifop and Cloinafop Con- tol of Bemaagiss and Reduces Zoysiaguass Injury” 2009 Pro- ceedings, Southern Weed Science Society, Orlando, Fovida, 62:2, XP 002672283 (209). Tym etal, “Leafy spurge contol with various picoinc aid ebi- «des Leafy Spurge Symposium, Riverton, WY, fu 9-10, 1986, XP 0550227901986), * cited by examiner Primary Examiner — Alton Pryor (14) Attorney, Agent, or Firm — Robe Chang on ABSTRACT Anherbicidal composition containing (a) uoroxypyrand () ephalofop, metamifop or proloxydim provides synergistic control of selected weeds patculrly on rice. 20 Claims, No Drawings US 8,420,571 B2 1 ‘SYNERGISTIC HERBICIDAL COMPOSITION ‘CONTAINING FLURONYPYR AND ‘CYHALOFOP, METAMIFOP OR PROFOXYDIM FIELD OF THE INVENTION ‘This application claims the benefit of U.S. Provisional Application Ser. No 61/255 685 fled on 28 Oct. 2008, This invention concerns a synergistic herbicidal composition coa- taining (a) fuoroxypyrand (bat easton herbicide selected from the group consisting of cybalofop, metamifop oF pro foxydim for controlling weeds in crops, paricularly in rice, but also otter monocot ropssuctas com, wheat, barley, at, rye, sorghum tort pastures, grasslands, rangelands fallow~ fand and indsteial vegetation management (IVM). These ‘compositions provide improved postemerzence herbicidal weed control BACKGROUND OF THE INVENTION “The protetion of eros from weeds and other vegetation “which inhibit crop growth and adversely impact crop quality and yield isa constantly recurring problem in agriculture. To help combat this problem, searchers in the feld of syaetic chemistry bave produced an extensive variety of chemicals and chemical formulations effective inthe contro of such ‘unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in ‘commercial use. Tn some cases, herbicidal active ingredients have been shown to be more eflctvein combination than when applied individually and this is referred to as “synergism” As described in the Herbicide Handbook of the Weed Science Society of America, Eighth Eution, 2002, p. 462 *'synee- ism’ [is] an interecton of two or more factors such thatthe cffect when combined is greater than the predicted effect hased onthe response to each factor appiod separately” The present invention is based on the discavery that fuoeoxypy, ‘ylalofop, metamifop and profoxydim,aleady known indi- Vidually for their herbicidal efficacy, display a synergistic effet when applied in combination. SUMMARY OF THE INVENTION ‘The present invention concems a synersstic herbicidal nnixtue comprising an herbicidal effective amount of (a) fiuooxypye and (b) an scp CoA carboxylase (ACCase) inhibitor herbicide. ACCase inhibitor herbicides include ‘compounds from the classes of aryloxyphenoxyprpionic cis and derivatives and eyelohexanediones. Parculaly usefil ACCas inbiitor herbicides inlude, but ae notin ited to, eyalofop, metamifop and poforyim. The compo siionsmay also continan agriculturally aeceptble avant andlor cari. “The preset invention also concerns herbicidal composi tions forand matnasofeontlingthegrowthof undesinble vegetation, particularly ince, but lo other monocot cops such cor whet bryos, ye, sorghum, tr, pasts, grasslands, rangelands, fllowland and IVM, and the use oF these synergistic compositions “The species species of ACCase inhibitors ik cyalotop suetamifop and profoxydin, i, the weed species which the respective compounds cont arehroad and highly comple mentary with hat of fuooxypye. For example, ites been surprisingly found that mixture of eal and ducroxy- yt exhibits @ synergistic action in the contol of bam- 2 yardgrass (Echinochloa crus-eaill; ECHCG), tighthead ‘sprangletop (Leprochloa panicoides (L.); LEFPA), Chinese sprangletop (Leptochloa chinensis (L.); LERCH), broadleat sgnalgrass (Brachiaria playphylla (GRISEB,) NASH BRAPP), winklegrass (schaemum rugosum SALISB. ISCRU), and giant foxtil (Setaria faberi; SETA) at applic cation rte equal to of lower than the rates ofthe individual compounds. Similarly, thas been surprisingly found that 2 nixture of metamifop and fluoroxypyr exhibits a synergistic action in the contol of bamyandgrass (Echinochloa erase «gall; HCG), Chinese sprangletop (Leptochloa chinensis (L); LEFCH), and broadleaf signalgrass (Brachiaria play. lpia (GRISEB,) NASH; BRAPP) a application rates equal 'o of lower than the rates of the individual compounds, In tuditon, it has been surprisingly found that a mixture of profoxydim and fluoroxypyr exhibits a synergistic action in the control of. amyardgrass (Echinochloa crus-gall ECHCG) and Chinese sprangletop (Leptochloa chinensis (L); LEECH) a application rates equal to or lower than the rates ofthe individual compounds. DETAILED DESCRIPTION OF THE INVENTION Cyhalofop isthe common name for (2R)-2-[4-(4-eyan0-2- ffuorophenoxy}phenoxy|-propanoie acid. Its herbicidal setivity is described in The Pesticide Manval, Fourteenth Edition, 206. Cybalofop provides post-emerpence conirlof zrass weeds in rice. Tt can be used as te aid ise or as an agriculturally acceptable salt or ester Use a am ester is pre= Jered, with the butyl ester being most prefered “Meéamifop isthe common name for 2R)-244-(6-chloro- 2-benzoxazoly!)oxy|-phenoxy]-N+2-fooropheny|)-N-me- thylpropanamide, lis herbicidal ativity is described in The Pesticide Manual, Fourteenth Fdition, 2006, Metamifop pro- Vides post-emergence control of grass Weeds ince and trl. Profoxyidim is the common name for 2-[1-[[244-chlo- rophenoxy propoxyJasno]-buy!]3-hydroxy-5-(etmay- dro-2H-thiopyraa-3-y1)-2-cyelohexen-L-one. Is herbicidal setivity is described in The Pesticide Manual, Fourtoonth Edition, 2006, Profoxydim provides post-emergence control of grass woods in ce Fluoroxypyr is the common name for ((-amino-3.5- Aichloro-6-Auogo-2-pyridinyJoxy]acetic ac, Its herbicidal activity is described ia The Pesticide Manual, Fouroeath Edition, 2006. Eluoroxypyr controls a Wide range of eco- rnomically important broadleaf woods. It can be used 38 the acid itself oras an agriculturally acceptable salt reser Use as an ester is preferred, with the meptyl ester being most prefered, ‘The term herbicide suse herein to mean an active ingre dieu that Kills, contols or otherwise adversely mosis the growth of plats. herbicidal elective or vegetation con trolling ammount is an amount of active ingredient which causes an adversely moifying effet and includes deviations fiom natural developmen, killing, regulation, desiccation, retardation, and the like. The tems plants and vegetation include germinant seods, emerging seedings, pants emerg~ ing from vegetative propagules, and established vegetation. Herbcidal activity is exhibited by the compounds of the synergistic mixture when they are applied directly totheplant orto the Tocus ofthe plant at any stage of growth or before planting oremergence. The eft observed depenls upon the plan species to be controlled, the stage of growth ofthe pla the application parameters of dilution and spay deop size, the parle size of solid components, the environmental condi- tions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, ax US 8,420,571 B2 3 the ike, swells the amouat of chemical applied. These and ‘other factors ea be adjusted sis kaown a the a to promote norseletve or soecive herbicidal action. Generally, itis prelemed to apply the composition ofthe preset invention Pesiemergenceo relatively iamatre undesirable vegetation to achieve the maximum con! of weeds In the composition ofthis invention the weight ratio of Siuroxypye acd equivalent to ehaloop (acid equivalent) at which the herbicidal eat is synergistic lies within the range ofberween aboot I:12and about 16:1. The weight ratio of furoxypyr (cd equivalent to metamiop and profoxy- ‘ian (active ingredient at which the herbicidal efecis yn- exist les within the range ofbeteen abut I:10andabout 75. ‘The rate at which the synergistic composition is applied ‘will depend upon the parla ype of weed tbe contd, the depree of contol require, and theming and method of pplication. ln genera, the composition ofthe iavetion ean beappied a an application ae ofeyaafop between about 32 gaetha and about 430 g sea and an application rate oF fiuoonypyrbetveen about 35 paths and about 540 gach. Ingenerathe composition a the invention can be applied at an application eate of metamifop or pefoxydim between about S gait andabout350 gaia andan pplication ate ‘of fvoroypyr between about 35 g arb and about 560 g sha The components ofthe synergistic mixtre of the present invention ean be applied either separately or as par ofa multipart herbicidal system “The synergistic mixture of the present aveaton can be applied in eonunetion with one or more ar herbicides to conto wider varity ofundesinble vegetation, When wed in conjunction with other herbicides, the composition canbe formulated wit the other erbicie or herbicides, tak mixed withthe other herbicide or herbicides or applied sequentially withthe ther herbicide or herbicides. Some of the herbicides that can be employed in cojunetion withthe synergistic composition of the present iaveation inelude 24D, ‘sectochlo.acifurfe,alonifen, 0172747 alachlor ami ‘sulfa, aminoriazoe, ammonium thioeyanae, ais, azine, AVE 301, aimsulfuvo, bafurst, besa nc, Beatwenc, benthiocar, benmbicyclon, Bifenox, bispyibaesodium. bromacil, brmoxynil, buachlor, batafencl, butalia, cafentvle, carbetamide, arena 2one-thyl, elorureool,chlrisiron,elogpropbatn ino sulfa, cletodim, clomazone, clopyaid, clorasulam- neti, yeosfamtron, yeioxydim, dam, dchlbeni, Aichlorpop-. dilosulam, dilufsican, ditenzopy, inthenanid, dinethenamid-p, digua, dkiopy. dura, FK2612, EPIC, esproarh,BI-75ethoxysl fron, thhen- anid, £7967, fenoxapop,lenoxaprop-thyl, Lenoxapop- ctbylsisoxatfentiyh feniazanide, fazasilivon, forest lam, focifop, fuzfop-?-buyl, aceosulfuron (LGC. 42183), fofenaeet, fufenpyratyl,umetslam, fhuniclerae-peny, unioxarin, Muometue, doprslia: ro fomesafe,fransuliua,fuelos,lufsinat fosinate-ammoninn, slyphosste, halosulfaron,haloxyfop- ney, haloxyfop-R,imazamethabenz, " imazamox, imazapicimazapy.imazayuin,imazebapyeinazsuliaon, indanofan inde, odosuifuron, ioxynl,ipfenearbezone (HOK-201, IR 579, soprotuon,ioxaben, isoxalutole, KUH-021,lctofen, linuron, MCPS, MCPA ester & amine recopmop.P mefenacet, mescsllro, mesolone acti sulforon (NC-620}, metolahlor, metosulam, metribuzn, mesure, molinate, MSMA, napropamide,nicosliuon, norfurazon, OK-9701,onhasifamuron,oyzali,oxaliae ay] oxadiazon, oxazichlomefone, oxyMlurien, paraquat, 4 pendimethalin, penoxsnlam, pentoxazone, pethoxamid, picloram, picolinafen piperophos, pretlchlr,primisulfve ron, propaclor,prpanil, propyrislfuron (TH-S47), pro~ pyzamide, prosllocarb, prosufuron, pyraclonil pyrazey pyrazoulluron, pyeibenzoxim (LGC-40863),_pyrtaid Pyriminoboc-mmethy,pyrimisulfan (KUH-021),pyroxsulam, Pyrxasulfone (KIH-485), quinelorae, quzalofop0.05 level using “Tukey's Test, me a wn eee ‘Space Acti of eid Compton ca Colby’ equstion was wed deere he Herbicdal | _ xu slug Reade facts expect fom the mixtures (Colby, R.Clelaton ™ : secon ofthesynriticand antagonist response ofherbicidecom- binations. Weeds 1967, 15,2022). sols Ricienia — _LiERA gcc The bllowingenuaon vasused ocala tbeerpected cusp eer Bh ctv of mints containing two ative ingens A and 23 - 5 Py ool lt om a > F Bonin 5-10) OR observed efficuey of active ingredient A tthe same BS os elm ‘concentration as used inthe mixture. g ao oS Beobsered efficacy of active ingredient B a the same on a om @ concentration assed inthe mixture. “ape * rapLe4 ‘Sas aay oe Gp Sms cy oi enon Ky Ome ctinapyemt Neo ooh sine Grane sgn aera DU Kec Was sR nh eng 21D pin cont io —Ambsionbae scons Hocigich) __CHCG BRA NOW Maniop—Muoypyr _ECHCG BRA sc eee eee Om eee Se or a 4 nm owlol> lll oo » So S 7 sf2llit ° a i ee eee “ ° wot es i @e 2222 8 3 Ts 3 a eee eee =i 8 Ce ee wo em ae >> oo (eee ot ee ca a * f of wD ee ar ae i 7 BPD lg ls f wo wl aS te i a 2s ¢ 2 oo ee i ee ea ea kata ONL RR od od rr 8 eee 23 0 Sm oe a eo = ee oo oe SS Le a ee ce a = oa 6 oem om we US 8,420,571 B2 9 TABLES Serie Acti Mei Campostons of Fhecepyenep rfoxsin om Key scout icin a Pray uraypyr _ECHCG src a s . ss ° os 9 2 DL s So & DF Bs 0 a 4 OT % oH ° am 3 oF s oleae 9a se oo 30 20 = me Mo Brcko ppa ee LECH Ltn ms Cone rep EPA lec patel pn What is claimed is: 1. A synergistic herbicidal mixture comprising an herbi-

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