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US010392630B2 (12 ) United States Patent ( 10 ) Patent No. : US 10 , 392 ,630 B2 Aponte et al. (45 ) Date of Patent: Aug. 27 , 2019 ( 54 ) PLANTS HAVING INCREASED TOLERANCE (56 ) References Cited TO HERBICIDES U . S . PATENT DOCUMENTS ( 71 ) Applicant: BASF AGRO B . V ., EA Arnheim (NL ) 5 , 169 ,770 A 12 / 1992 Chee et al . 5 , 198 ,013 A 3 / 1993 Hirai et al. (72 ) Inventors : Raphael Aponte , Mannheim (DE ) ; 5 , 322 , 783 A 6 / 1994 Tomes et al. 5 , 366 , 892 A 11/ 1994 Foncerrada et al. Stefan Tresch , Kirchheim (DE ) ; 5 , 376 ,543 A 12 / 1994 Chee et al. Matthias Witschel , Bad Duerkheim 5 , 380 ,831 A 1 / 1995 Adang et al. (DE ); Jens Lerchl, Golm (DE ) ; Dario 5 ,436 , 391 A 7 / 1995 Fujimoto et al . Massa , Mannheim (DE ) ; Tobias Seiser , 5 , 485 , 192 A 1 / 1996 Nagahata et al . Mannheim (DE ) ; Thomas Mietzner , 5 , 593 , 881 A 1 / 1997 Thompson et al . 5 , 723 , 756 A 3 / 1998 Peferoen et al. Annweiler (DE ) ; Jill Marie Paulik , 5 , 737 ,514 A 4 / 1998 Stiffler Cary , NC (US ) ; Chad Brommer , 5 , 747 , 450 A 5 / 1998 Ohba et al . Raleigh , NC (US ) 5 , 767 , 373 A 6 / 1998 Ward et al. 5 , 773 ,702 A 6 / 1998 Penner et al. 5 , 859 , 348 A 1 / 1999 Penner et al. ( 73 ) Assignee : BASF AGRO B . V . , Arnhem (NL ) 5 , 939 , 360 A 8 / 1999 Adachi et al . 5 ,939 ,602 A 8 / 1999 Volrath et al . ( * ) Notice : Subject to any disclaimer, the term of this 5 , 948 , 917 A 9 / 1999 Adachi et al. patent is extended or adjusted under 35 5 , 990 , 387 A 11/ 1999 Tomes et al . 6 ,018 , 105 A 1 / 2000 Johnson et al. U . S . C . 154 (b ) by 0 days . 6 ,027 , 945 A 2 / 2000 Smith et al . 6 ,084 , 155 A 7 / 2000 Volrath et al . (21 ) Appl. No. : 14 /911 , 814 6 , 160 , 206 A 12 / 2000 Sato et al . 6 , 308 ,458 B1 10 / 2001 Volrath et al. Aug . 12 , 2014 6 , 368 , 800 B1 4 /2002 Smith et al. ( 22 ) PCT Filed : 6 ,653 , 529 B2 11 /2003 Peng et al . ( 86 ) PCT No. : PCT/ IB2014 / 063877 (Continued ) $ 371 (c ) ( 1 ) , FOREIGN PATENT DOCUMENTS ( 2 ) Date : Feb . 12 , 2016 CA 2382090 A1 2 / 2001 (87 ) PCT Pub. No. : W02015 /022640 CA 2807035 AL 2 / 2012 PCT Pub . Date : Feb . 19 , 2015 (Continued ) (65 ) Prior Publication Data OTHER PUBLICATIONS Maniatis et al. , 1982 , Molecular Cloning : A Laboratory Manual , US 2016 /0201078 A1 Jul. 14 , 2016 Cold Spring Harbor Laboratory , pp . 324 - 343 and 387 -389 . * Keskin et al . , 2004 , Protein Science 13 : 1043 - 1055 . * Guo et al. , 2004 , Proceedings of the National Academy of Sciences Related U . S . Application Data USA 101 : 9205 - 9210 . * Thornton et al. , 2000 , Nature Structural Biology , structural genomic ( 60 ) Provisional application No . 61/ 866 , 067, filed on Aug . supplement , Nov. 2000 : 991 - 994 . * 15 , 2013 , provisional application No . 61/ 864, 671 , Brachypodium distachyon protoporphyrinogen oxidase with UniProt filed on Aug. 12 , 2013 , provisional application No . accession No. I1IZ42 , published on Jun . 13 , 2012 . * 61/ 864, 672 , filed on Aug. 12 , 2013 . Koch et al. , 2004 , EMBO J . 23 : 1720 - 1728 . * (Continued ) (51 ) Int. Ci. C12N 15 / 82 ( 2006 . 01 ) Primary Examiner — Bratislav Stankovic AOIN 37 / 48 ( 2006 .01 ) (74 ) Attorney, Agent, or Firm — Marshall , Gerstein & AOIN 43 /54 ( 2006 .01 ) Borun LLP A01N 43 /653 ( 2006 .01 ) (57 ) ABSTRACT A01N 43 /84 ( 2006 . 01 ) The invention refers to plants comprising wild -type or AOIN 57/ 16 ( 2006 . 01 ) mutated Alopecurus PPO enzymes, and methods of obtain C12N 9 / 02 ( 2006 .01 ) ing such plants . The present invention further refers to a (52 ) U .S . CI. method for controlling weeds at a plant cultivation site , the CPC .. .. .. C12N 15 /8274 ( 2013 .01 ) ; A01N 37 / 48 method comprising the steps of providing , at said site , a ( 2013 .01 ) ; AOIN 43 / 54 (2013 .01 ) ; AOIN plant that comprises at least one nucleic acid comprising a 43 /653 (2013 .01 ) ; AOIN 43 /84 ( 2013 .01 ) ; nucleotide sequence encoding a wild - type or a mutated AOIN 57/ 16 ( 2013 .01 ) ; C12N 9 /001 Alopecurus PPO enzyme which is resistant or tolerant to a ( 2013 .01 ) ; C12N 9 /0071 ( 2013 .01 ) ; C12Y PPO - inhibiting herbicide by applying to said site an effec 103 /03004 ( 2013 .01 ) tive amount of said herbicide . (58 ) Field of Classification Search None 7 Claims, 6 Drawing Sheets See application file for complete search history . Specification includes a Sequence Listing . US 10 ,392 ,630 B2 Page 2 (56 ) References Cited WO WO - 2015 /022636 A2 2 / 2015 WO W O - 2015 /022639 A2 2 / 2015 U . S . PATENT DOCUMENTS WO WO - 2015 /092706 A1 6 / 2015 6 ,905 , 852 B1 6 / 2005 Horikoshi et al . 7 ,671 , 254 B23 / 2010 Tranel et al . OTHER PUBLICATIONS 7 ,705 ,200 B2 4 / 2010 Dam et al . Arnould et al. , The domain structure ofprotoporphyrinogen oxidase , 7 ,745 ,699 B2 6 / 2010 Nakajima et al . the molecular target of diphenyl ether -type herbicides . Proc. Natl . 7 , 842 , 856 B2 11/ 2010 Tranel et al . 8 ,097 ,774 B2 1 / 2012 Hawkes et al. Acad . Sci. USA , 95 : 10553 - 8 (1998 ). 8 , 129 ,589 B2 3 / 2012 Tanaka et al. Che et al. , Molecular characterization and subcellular localization of 8 ,338 ,337 B2 12 / 2012 Song et al . protoporphyrinogen oxidase in spinach chloroplasts . Plant Physiol. 2003 /0236208 Al 12/ 2003 Kmiec et al. 124 : 59 - 70 ( 2000 ) . 2004 / 0082770 A1 4 /2004 Castle et al . Choi et al. , Generation of resistance to the diphenyl ether herbicide , 2005 /0084859 AL 4 / 2005 Nakajima et al . oxyfluorfen , via expression of the Bacillus subtilis protoporphyrinogen 2007 /0039067 A1 * 2 / 2007 Feldmann .. .. .. .. .. CO7K 14 /415 oxidase gene in transgenic tobacco plants . Biosci. Biotechnol. 800 / 278 Biochem . 62 ( 3 ) : 558 -60 ( 1998 ) . 2007 / 0050863 A1 3 / 2007 Tranel et al . Corradi et al. , Crystal structure of protoporphyrinogen oxidase from 2007 /0214515 Al 9 / 2007 Dam et al. Myxococcus xanthus and it complex with the inhibitor acifluorfen . 2009 / 0049567 A1 2 /2009 Olhoft et al . J Biol Chem . 281( 50 ) : 38625 - 33 ( 2006 ) . 2010 /0100988 Al Dayan et al ., Phytotoxicity of Protoporphyrinogen Oxidase Inhibi 4 / 2010 Tranel et al. tors : Phenomenology , Mode of Action and Mechanisms of Resis 2011 /0201501 A1 8 / 2011 Song et al . tance , Herbicide Activity : Toxicology , Biochemistry and Molecular 2012 /0122223 AL 5 / 2012 Gocal et al. Biology , eds. Roe et al. , pp . 11 - 35 ( 1997 ) . 2013 /0184155 Al 7 / 2013 Newton et al. Extended European Search Report , issued in co -assigned applica 2014 / 0123340 A1 5 / 2014 Aponte et al . tion No . 11848519 . 2 , dated Apr. 23 , 2014 . 2014 / 0189906 A1 7 / 2014 Gocal et al . GenBank Accession No. AX084732 , submitted on Mar. 9 , 2001 . 2015 / 0299725 Al 10 / 2015 Lerchl et al . Ha et al . , The plastidic Arabidopsis protoporphyrinogen IX oxidase 2016 /0194654 AL 7 / 2016 Aponte et al. gene, with or without the transit sequence , confers resistance to the 2016 / 0201078 AL 7 / 2016 Aponte et al . diphenyl ether herbicide in rice . Plant Cell Environ . 27 : 79 - 88 ( 2003 ) . FOREIGN PATENT DOCUMENTS Hanin et al ., Gene targeting in Arabidopsis . Plant J . 28 : 671 - 7 ( 2001 ) . CN 1150820 A 5 /1997 CN 1036571 C 12 / 1997 Hao et al. , Protoporphyrinogen oxidase inhibitor : An ideal target for CN 1212724 A 3 / 1999 herbicide discovery . Chimia , 65 ( 12 ) : 961 - 9 (2011 ) . CN 1175107 C 11/ 2004 Heinemann et al. , Functional definition of the tobacco CN 1894408 A 1 / 2007 protoporphyrinogen IX oxidase substrate -binding site . Biochem . J . CN 101215289 A 7 / 2008 402 : 575 - 80 ( 2007 ) . CN 101437844 A 5 /2009 Holmberg, A fine line : New herbicide - tolerant crops blur the fine CN 101998988 A 3 / 2011 line between weed control and crop injury . Successful Farm . 98 ( 5 ) : DE 19505995 A1 8 / 1996 25 - 7 (2000 ) . EP 0397687 Al 11 / 1990 Huang et al . , Synthesis and herbicidal activity of isoindoline - 1 , 3 EP 0424047 A1 4 / 1991 dione substituted benzoxazinone derivatives containing a carbox EP 0900795 A1 3 / 1999 WO WO - 93 /07256 Al 4 / 1993 ylic ester group . J . Agric . Food Chem . 57 : 9585 - 92 ( 2009 ) . WO WO - 95 / 34659 Al 12 / 1995 International Preliminary Report on Patentability , issued in PCT/ WO WO - 96 / 26202 A1 8 / 1996 IB2011 /055701 , dated Jun . 27 , 2013 . WO WO - 1997 / 004088 A1 2 / 1997 International Search Report , corresponding International Applica WO WO - 1997 /032011 A1 9 / 1997 tion No . PCT/ EP2013 / 062744 , dated Dec. 10 , 2014 . WO WO - 97 /41116 A1 11 / 1997 International Search Report, issued in PCT/ IB2011/ 055701 , dated WO WO - 97 /41117 A1 11 / 1997 May 3 , 2012 . WO WO - 97 /41118 Al 11 / 1997 Jung et al . , Dual targeting ofMyxococcus xanthus protoporphyrinogen WO WO - 1998 /029554 A1 7 / 1998 oxidase into chloroplasts and mitochondria and high level oxyfluorfen wo WO - 1998 /033927 A1 8 / 1998 resistance . Plant Cell Environ . 27 : 1436 - 46 ( 2004 ) . WO WO - 2001/ 012815 A1 2 / 2001 Jung et al. , Resistance mechanisms in protoporphyrinogen oxidase WO WO - 2001 /068826 A2 9 / 2001 WO WO -01 / 83459 A2 11 /2001 (PROTOX ) inhibitor- resistant transgenic rice . J . Plant Biol. 50 ( 3 ) : WO WO - 02 / 068607 A2 9 / 2002 586 - 94 ( 2007) . WO WO - 2005 / 107437 A2 11/ 2005 Koch et al. , Crystal structure of protoporphyrinogen IX oxidase : A WO WO - 2006 /024820 A1 3 / 2006 key enzyme in Haem and chlorophyll biosynthesis . EMBO J . 23 : WO WO - 2006 /037945 A1 4 / 2006 1720 - 8 ( 2004 ) . WO WO - 2007 /024739 A2 3 / 2007 Layer et al ., Structure and function of enzymes in Heme biosyn WO WO - 2007 /071900 Al 6 / 2007 thesis .
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    J. Aquat. Plant Manage. 45: 132-136 Comparison of Imazapyr and Imazamox for Control of Parrotfeather (Myriophyllum aquaticum (Vell.) Verdc.) RYAN M. WERSAL1 AND JOHN D. MADSEN1,2 INTRODUCTION techniques (Moreira et al. 1999). To date, chemical control has been the most effective method for controlling infesta- Parrotfeather (Myriophyllum aquaticum (Vell. Verdc) is an in- tions of M. aquaticum. Contact herbicides such as diquat vasive aquatic plant to the United States that is native to South (6,7-dihydrodipyrido (1,2-a:2’,1’-c) pyrazinedium dibro- America. Myriophyllum aquaticum is described as “stout, stems mide) and endothall (7-oxabicyclo (2.2.1) heptane-2,3-dicar- moderately elongate, partially submersed but with portions of boxylic acid) have been evaluated with mixed results leafy branches emersed (Godfrey and Wooten 1981). Emer- (Moreira et al. 1999, Westerdahl and Getsinger 1988). Con- gent leaves are whorled, stiff, usually with 20 or more linear fil- tact herbicides are typically effective for short-term control, iform divisions, appearing feather-like and grayish green. but significant regrowth of M. aquaticum typically occurs and Submersed shoots are comprised of whorls of four to six fila- multiple applications are necessary (Moreira et al. 1999). mentous, pectinate, red or orange, leaves arising from each Therefore, the use of a systemic herbicide may be more ef- node. Flowers are all pistillate, borne in the axils of unreduced fective in controlling this species. leaves (Godfrey and Wooten 1981). Myriophyllum aquaticum is Imazapyr (2-[4,5-dihydro-4-methyl-4-(1-methylethyl)5-oxo- dioecious, however only pistillate plants are found outside of 1H-imazol-2-yl]-3-pyridinecarboxylic acid) is a systemic herbi- its native range (Sutton 1985).
  • Imazapyr Human Health and Ecological Risk Assessment FINAL REPORT

    Imazapyr Human Health and Ecological Risk Assessment FINAL REPORT

    SERA TR-052-29-03a Imazapyr Human Health and Ecological Risk Assessment FINAL REPORT Submitted to: Paul Mistretta, COR USDA/Forest Service, Southern Region 1720 Peachtree RD, NW Atlanta, Georgia 30309 USDA Forest Service Contract: AG-3187-C-06-0010 USDA Forest Order Number: AG-43ZP-D-11-0012 SERA Internal Task No. 52-29 Submitted by: Patrick R. Durkin Syracuse Environmental Research Associates, Inc. 8125 Solomon Seal Manlius, New York 13104 E-Mail: [email protected] Home Page: www.sera-inc.com December 16, 2011 Table of Contents LIST OF FIGURES ...................................................................................................................... vii LIST OF TABLES ........................................................................................................................ vii LIST OF APPENDICES ............................................................................................................... vii ACRONYMS, ABBREVIATIONS, AND SYMBOLS .............................................................. viii COMMON UNIT CONVERSIONS AND ABBREVIATIONS .................................................... x CONVERSION OF SCIENTIFIC NOTATION ........................................................................... xi EXECUTIVE SUMMARY .......................................................................................................... xii 1. INTRODUCTION ...................................................................................................................... 1 1.1. Chemical Specific Information
  • Use of Mesotrione for Annual Bluegrass (Poa Annua L.) at Cool

    Use of Mesotrione for Annual Bluegrass (Poa Annua L.) at Cool

    USE OF MESOTRIONE FOR ANNUAL BLUEGRASS (POA ANNUA L.) AT COOL- SEASON TURFGRASS ESTABLISHMENT by KATELYN A. VENNER A Thesis submitted to the Graduate School-New Brunswick Rutgers, The State University of New Jersey in partial fulfillment of the requirements for the degree of Master of Science Graduate Program in Plant Biology written under the direction of Stephen E. Hart Ph.D. and approved by ________________________ ________________________ ________________________ New Brunswick, New Jersey October, 2011 ABSTRACT OF THE THESIS USE OF MESOTRIONE AT COOL-SEASON TURFGRASS ESTABLISMENT By Katelyn Anne Venner Thesis director: Stephen E. Hart Annual bluegrass is a problematic weed in highly maintained turfgrass environments, and is difficult to control due to its adaptability to highly maintained turfgrass environments and lack of highly effective chemical control options. Mesotrione is a relatively new herbicide which has been found to show some level of control of annual bluegrass, and is safe to use at cool season turfgrass establishment. Thus, mesotrione has potential to be utilized for weed control in cultivated sod production. The objectives of this research were to evaluate mesotrione to determine: 1) tolerance of selected tall fescue cultivars, an important turfgrass species cultivated for sod, to applications of mesotrione; 2) the length of residual of mesotrione versus prodiamine, bensulide and dithiopyr for control of annual bluegrass; and 3) potential of mesotrione to control winter annual broadleaf weeds at Kentucky bluegrass establishment. Tall fescue cultivars were found to be tolerant to mesotrione applications made preemergence and preemergence plus 4 weeks after emergence at higher rates than required for weed control.