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(12) Patent Application Publication (10) Pub. No.: US 2014/0066307 A1 Poree Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0066307 A1 Poree Et Al US 20140.0663 O7A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0066307 A1 POree et al. (43) Pub. Date: Mar. 6, 2014 (54) USE OF Publication Classification N-(1,2,5-OXADIAZOL-3-YL)BENZAMIDES FOR CONTROLLING UNWANTED PLANTS (51) Int. Cl. IN AREAS OF TRANSGENC CROPPLANTS AOIN 43/82 (2006.01) BEING TOLERANT TO HPPD INHIBITOR (52) U.S. Cl. HERBCDES CPC ...................................... A0IN 43/82 (2013.01) USPC ............................ 504/139: 548/125; 504/265 (75) Inventors: Fabien Poree, Frankfurt (DE); Andreas Van Almsick, Karben (DE); Arnim (57) ABSTRACT Köhn, Klein-Winternheim (DE); Bernd Use of N-(1,2,5-Oxadiazol-3-yl)benzamides of formula (I) or Laber, Idstein (DE); Ruediger Hain, salts thereof Frankfurt (DE) (73) Assignee: Bayer Intellectual Property GmbH, (I) Monheim (DE) (21) Appl. No.: 14/006,282 (22) PCT Filed: Mar. 21, 2012 (86). PCT No.: PCT/EP2012/054978 S371 (c)(1), for controlling unwanted plants in areas of transgenic crop (2), (4) Date: Nov. 23, 2013 plants being tolerant to HPPD inhibitor herbicides by con taining one or more chimeric gene(s) comprising (I) a DNA Related U.S. Application Data sequence encoding hydroxyphenylpyruvate dioxygenase (60) Provisional application No. 61/467,631, filed on Mar. (HPPD) derived from a member of a group of organisms 25, 2011. consisting of (a) Avena, (b) Pseudomonas, (c) Synechococ coideae, (d) Blepharismidae, (e) Rhodococcus, (f) Picro (30) Foreign Application Priority Data philaceae, (g) Kordia, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before Mar. 25, 2011 (EP) .................................. 11159750.6 defined organisms. US 2014/0066307 A1 Mar. 6, 2014 USE OF the transformation of plants with a gene encoding a PDH N-(1,2,5-OXADIAZOL-3-YL)BENZAMIDES enzyme makes it possible to increase the tolerance of said FOR CONTROLLING UNWANTED PLANTS plants to HPPD inhibitors. IN AREAS OF TRANSGENC CROPPLANTS BEING TOLERANT TO HPPD INHIBITOR (0010. In WO 2002/046387, an gene obtained from Avena HERBCDES sativa encoding an HPPD was described to generate plants overexpressing Such gene and thereby causing tolerance to 0001. The invention relates to the use of N-(1,2,5-oxadia various HPPD-inhobitor herbicides. Zol-3-yl)benzamides for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor 0011. In WO 2008/150473, the combination of two dis herbicides. tinct tolerance mechanisms—a modified Avena sativa gene 0002 WO2011/035874 (being filed under PCT/EP2010/ coding for a mutant HPPD enzyme and a CYP450 Maize 0.05739 in the name of Bayer CropScience AG on Sep. 18, monooxygenase (nsf1 gene)—was exemplified in order to 2010) discloses several new N-(1,2,5-oxadiazol-3-yl)benza obtain an improved tolerance to HPPD inhibitor herbicides, mides whose phenyl ring is Substituted in the 2-, 3- and but no data have been disclosed demonstrating the Synergistic 4-position by selected radicals and their use as HPPD inhibi effects based on the combination of both proteins. tor herbicides for weed control. 0003. However, the herbicidal activity ofN-(1,2,5-oxadia 0012. In WO 2010/085705, several mutants of the Avena Zol-3-yl)benzamides whose phenyl ring is substituted in the sativa HPPD were described as well as plants comprising 2-, 3- and 4-position by selected radicals might cause dam genes encoding Such mutated HPPD and thereby causing an ages on several crop plants which limit their use in Such crop increased tolerance to various HPPD-inhibitor herbicides growing areas as herbicides for weed control. compared to non-mutated HPPD. 0004 HPPD inhibitor herbicides can be used against grass 0013 Recently, several new genes encoding HPPD and/or broad leaf weeds in crop plants that display metabolic enzymes from various organisms have been identified and tolerance. Such as maize (Zea mays) in which they are rapidly employed for obtaining crop plants that show an agronomi degraded (Schulz et al., (1993). FEBS letters, 318, 162-166; cally useful level of tolerance concerning the application of Mitchell et al., (2001) Pest Management Science, Vol 57, various HPPD inhibitor herbicides. 120-128; Garcia et al., (2000) Biochem., 39, 7501-7507: Pallett et al., (2001) Pest Management Science, Vol 57, 133 0014. The work concerning the implementation of such 142). In order to extend the scope of these HPPD inhibitor tolerance against HPPD inhibitor herbicides have extensively herbicides, several efforts have been developed in order to been described in the PCT-applications being filed in the confer to plants, particularly plants without or with an under name of Bayer CropScience AG on Dec. 22, 2010, having the performing metabolic tolerance, a tolerance level acceptable filing numbers PCT/EP2010/070561 (published as WO 2011/ under agronomic field conditions. 076877; relates to nucleic acid sequences encoding a hydrox 0005 Meanwhile transgeninc plants have been engi yphenylpyruvate dioxygenase (HPPD) obtained from bacte neered by by-passing HPPD-mediated production of ria belonging to the Subfamily Synechococcoideae and homogentisate (U.S. Pat. No. 6,812.010), overexpressing the sensitive enzyme so as to produce quantities of the target certain mutants thereof); PCT/EP2010/070567 (published as enzyme in the plant which are sufficient in relation to the WO 2011/076882; encoding a hydroxyphenylpyruvate herbicide has been performed (WO96/38567). dioxygenase obtained from protists belonging to the family 0006 Alternatively, transgenic plants have been generated Blepharismidae); PCT/EP2010/070578 (published as WO expressing HPPD proteins that have been mutated at various 2011/076892; encoding a hydroxyphenylpyruvate dioxyge positions in order to obtain a target enzyme which, while nase obtained from bacteria belonging to the genus Rhodo retaining its properties of catalysing the transformation of coccus and certain mutants thereof); PCT/EP2010/070570 HPP into homogentisate, is less sensitive to HPPD inhibitor (published as WO 2011/076885; encoding a hydroxyphe herbicides than is the native HPPD before mutation (for nylpyruvate dioxygenase obtained from Euryarchaeota example see at EP496630, WO 99/24585). belonging to the family Picrophilaceae and certain mutants 0007 More recently, the introduction of a Pseudomonas thereof); PCT/EP2010/070575 (published as WO 2011/ HPPD gene into the plastid genome of tobacco and soybean 076889; encoding a hydroxyphenylpyruvate dioxygenase has shown to be more effective than nuclear transformation, conferring eventolerance to post-emergence application of at obtained from bacteria belonging to the genus Kordia and least one HPPD inhibitor (Dufourmantel et al., 2007, Plant certain mutants thereof) and which are hereby incorporated Biotechnol J.5(1):118-33). by reference concerning the production of the respective 0008. In WO 2009/144079, a nucleic acid sequence transgenic plants conferring tolerance to HPPD inhibitor her encoding a mutated hydroxyphenylpyruvate dioxygenase bicides. (HPPD) at position 336 of the Pseudomonas fluorescens HPPD protein and its use for obtaining plants which are 0015. It has now been found that N-(1,2,5-oxadiazol-3-yl) tolerant to HPPD inhibitor herbicides is disclosed. benzamides whose phenyl ring is substituted in the 2-, 3- and 0009. In WO 04/024928, the inventors have sought to 4-position by selected radicals can be employed on transgenic increase the prenylduinone biosynthesis (e.g., synthesis of crop plants being tolerant to HPPD inhibitor herbicides by plastoquinones, tocopherols) in the cells of plants by increas containing one or more genes conferring tolerance to HPPD ing the flux of the HPP precursor into the cells of these plants. inhibitor herbicides. This has been done by connecting the synthesis of said pre 0016 Subject matter of the present invention is the use of cursor to the “shikimate” pathway by overexpression of the N-(1,2,5-oxadiazol-3-yl)benzamides of the formula (I) or prephenate-dehydrogenase (PDH). They have also noted that their salts US 2014/0066307 A1 Mar. 6, 2014 alkyl, phenyl or phenyl-(C-C)-alkyl, where the 12 last (I) mentioned radicals are substituted by s radicals selected from R N O X the group consisting of cyano, halogen, nitro, rhodano, OR, O S(O),R, N(R), NROR, COR, OCOR, SCOR, \ 2 Y, NRCOR, COR, COSR, CONCR), and (C-C)-alkoxy N N (C-C)-alkoxycarbonyl, H R is (C-C)-alkyl, (C-C)-alkenyl, (C-C)-alkynyl, (C- Z C)-cycloalkyl, (C-C)-cycloalkyl-(C-C)-alkyl, phenyl or phenyl-(C-C)-alkyl, where the seven last-mentioned radi cals are Substituted by S radicals from the group consisting of in which cyano, halogen, nitro, thiocyanato, OR, S(O),R, N(R), R is hydrogen, (C-C)-alkyl, (C-C)-cycloalkyl, halo-(C- NROR, COR, OCOR, SCOR, NRCOR, CO.R., C)-alkyl, (C-C)-alkoxy, halo-(C-C)-alkoxy, (C-C)- COSR, CONCR), and (C-C)-alkoxy-(C-C)-alkoxycar alkenyl, (C-C)-alkenyloxy, (C-C)-haloalkenyl, (C-C)- bonyl, alkynyl, (C-C)-alkynyloxy, (C-C)-haloalkynyl, cyano, R is hydrogen, (C-C)-alkyl, (C-C)-alkenyl or (C-C)- nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acety alkynyl, lamino, benzoylamino, methoxycarbonyl, ethoxy-carbonyl, R" is (C-C)-alkyl, (C-C)-alkenyl or (C-C)-alkynyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, R is methyl or ethyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbo n is 0, 1 or 2, nyl, halogen, amino, aminocarbonyl, methyl-aminocarbonyl, s is 0, 1, 2 or 3, dimethylaminocarbonyl, methoxymethyl or heteroaryl, het for controlling unwanted plants in areas of transgenic crop erocyclyl or phenyl, each of which is substituted by S radicals plants being tolerant to HPPD inhibitor herbicides by con selected from the group consisting of methyl, ethyl, methoxy, taining one or more chimeric gene(s) (I) comprising a DNA trifluoromethyl and halogen, sequence encoding hydroxyphenylpyruvate dioxygenase X and Zindependently of one another are in each case nitro, (HPPD) derived from a member of a group of organisms halogen, cyano, formyl, rhodano, (C-C)-alkyl, (C-C)-ha consisting of (a) Avena, preferably Avena sativa, more pref loalkyl, (C-C)-alkenyl, (C-C)-haloalkenyl, (C-C)-alky erably comprising a DNA sequence identical to SEQID No.
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