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WO 2010/126794 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 4 November 2010 (04.11.2010) WO 2010/126794 Al (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every AOlN 41/02 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/US20 10/032242 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 23 April 2010 (23.04.2010) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (26) Publication Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/174,391 30 April 2009 (30.04.2009) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant (for all designated States except US): NOVUS GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, INTERNATIONAL INC. [US/US]; 20 Research Park ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, Drive, St. Charles, Missouri 63304 (US). TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, (72) Inventor; and MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, (75) Inventor/Applicant (for US only): ABOU-NEMEH, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Ibrahim [US/US]; 28 Serviceberry Court, Lake St. Louis, ML, MR, NE, SN, TD, TG). Missouri 63367 (US). Published: (74) Agents: DOTY, Kathryn et al; Polsinelli Shughart PC, 100 South Fourth Street, Suite 1100, St. Louis, Missouri — with international search report (Art. 21(3)) 63 102-1825 (US). (54) Title: METHODS FOR INCREASING GROWTH AND YIELD OF PLANTS WITH METHIONINE COMPOUNDS (57) Abstract: The present invention encompasses a method for increasing the growth and yield of plants. The method comprises administering to the plant a composition comprising an amount of a methionine compound that results in an increase in plant growth or yield compared to the growth or yield of the plant without the administration of the methionine compound. METHODS FOR INCREASING GROWTH AND YIELD OF PLANTS WITH METHIONINE COMPOUNDS FIELD OF THE INVENTION [0001] The invention provides methods for enhancing the growth and yield of plants by administering methionine compounds to the plant. BACKGROUND OF THE INVENTION [0002] Under natural growth conditions, plants use nutrients from the soil, water and solar energy to produce all the compounds needed for vegetative and productive development. Unfavorable weather conditions, poor soil fertility, pest attacks or diseases may impair the complicated metabolic processes of the plant, resulting in slower development and reduced yields, especially under intensive crop production techniques. Supplementing plants with compounds to help the plant overcome these stresses, as such, may provide a means to increase plant growth and yield. SUMMARY OF THE INVENTION [0003] Accordingly, one aspect of the invention encompasses a method for increasing the growth or yield of a plant. The method comprises administering to the plant a composition comprising an amount of a methionine compound that results in an increase in plant growth or yield compared to the growth or yield of the plant without the administration of the methionine compound. [0004] Other aspects and iterations of the invention are described more thoroughly below. DETAILED DESCRIPTION OF THE INVENTION [0005] The present invention provides compositions and methods for providing a methionine compound to a plant. Typically, the methionine compound increases the growth and/or yield of the plant. Suitable methionine compounds are described below. (I) Methionine Compounds [0006] One aspect of the invention encompasses compounds having a methionine derivative or methionine analog (hereinafter referred to as "methionine compound"). (a) Methionine Sulfoxides and Sulfones [0007] In one embodiment, the methionine compound is a methionine sulfoxide or methionine sulfone having formula (I): wherein: * is a chiral carbon; R1 is methyl or ethyl; R2 is oxygen or hydrogen; R3 is an acyl group or hydrogen; and n is an integer from 1 to 3 . [0008] Compounds corresponding to formula (I) may be a methionine sulfoxide (i.e., when R2 is hydrogen) or a methionine sulfone (i.e., when R2 is oxygen). Depending upon the embodiment, the compound having formula (I) may be normethionine (i.e., n is 1), methionine (i.e., n is 2) or homomethionine (i.e., n is 3). In certain embodiments, when R3 is an acyl group, the compound having formula (I) may be an acetyl methionine sulfoxide or an acetyl methionine sulfone. Examples of suitable acyl groups include formyl, acetyl, propionyl and succinyl. Exemplary acyl groups are formyl and acetyl. The compound having formula (I) may also be an ester derivative. Examples of suitable ester derivatives include methyl, ethyl, propyl, isopropyl, and butyl esters. For each embodiment with compounds having formula (I), both the D- and L-isomers are included within the scope of the invention. The invention also encompasses salts of compounds having formula (I). Suitable examples of salts include ammonium salts, alkaline earth metal salts (e.g., magnesium and calcium), alkali metal salts (e.g., lithium, sodium, and potassium), copper salts, zinc salts, cobalt salts, chromium salts, manganese salts, and iron salts. [0009] In one embodiment, the compound having formula (I) is L- methionine sulfoxide or D-methionine sulfoxide (i.e., Ri is methyl; R2 is hydrogen, R3 is hydrogen and n is 2). In an alternative embodiment, the compound having formula (I) is L-methionine sulfone or D-methionine sulfone (i.e., Ri is methyl; R2 is oxygen, R3 is hydrogen and n is 2). In a further embodiment, the compound having formula (I) is N-acetyl-L-methionine sulfoxide or N-acetyl-D-methionine sulfoxide (i.e., Ri is methyl; R2 is hydrogen, R3 is acetyl and n is 2). In another embodiment, the compound having formula (I) is N-formyl-L-methionine sulfoxide or N-formyl-D-methionine sulfoxide (i.e., Ri is methyl; R2 is hydrogen, R3 is formyl and n is 2). In still another embodiment, the compound corresponding to formula (I) is N-acetyl-L-methionine sulfone or N-acetyl-D-methionine sulfone (i.e., Ri is methyl; R2 is oxygen, R3 is acetyl and n is 2). In an additional embodiment, the compound corresponding to formula (I) is N-formyl-L- methionine sulfone or N-formyl-D-methionine sulfone (i.e., Ri is methyl; R2 is oxygen, R3 is formyl and n is 2). (b) Acyl Methionine Compounds [001 0] In an alternative embodiment, the methionine compound is an acyl methionine derivative having formula (II): wherein: * is a chiral carbon; R4 is methyl or ethyl; R5 is an acyl group; n is an integer from 1 to 3 . [001 1] The compound having formula (II) may be normethionine (i.e., n is 1), methionine (i.e., n is 2) or homomethionine (i.e., n is 3). Examples of suitable acyl groups (i.e., R5) include formyl, acetyl, propionyl and succinyl. Exemplary acyl groups are formyl and acetyl. The compound having formula (II) may also be an ester derivative. Examples of suitable ester derivatives include methyl, ethyl, propyl, isopropyl, and butyl esters. For each embodiment with compounds having formula (II), both the D- and L-isomers are included within the scope of the invention. The invention also encompasses salts of compounds having formula (II). Suitable examples of salts include ammonium salts, alkaline earth metal salts (e.g., magnesium and calcium), alkali metal salts (e.g., lithium, sodium, and potassium), copper salts, zinc salts, cobalt salts, chromium salts, manganese salts, and iron salts. [001 2] In one embodiment, the compound having formula (II) is N- acetyl-L-methionine or N-acetyl-D-methionine (i.e., R4 is methyl; R5 is acetyl and n is 2). In another embodiment, the compound having formula (I) is N-formyl-L- methionine or N-formyl-D-methionine (i.e., R4 is methyl; R5 is formyl and n is 2). In still another embodiment, the compound having formula (II) is N-propionyl-L- methionine or N-propionyl-D-methionine (i.e., R4 is methyl; R5 is propionyl and n is 2). In a further embodiment, the compound having formula (II) is N-succinyl-L- methionine or N-succinyl-D-methionine (i.e., R4 is methyl; R5 is succinyl and n is 2). (c) Peptides having Methionine [001 3] In a further alternative embodiment, the methionine compound may include more than one methionine amino acid residue. In this context, the methionine compound may be a peptide that includes from about 1 to about 5 methionine amino acid residues. In an additional embodiment, the methionine compound may be a peptide that has from about 2 to about 4 methionine amino acid residues. In a further embodiment, the methionine compound may be a peptide having three methionine amino acid residues. In an exemplary embodiment, the methionine compound may be a dipeptide corresponding to formula (III): (III) wherein: * is a chiral carbon; R6 and Ri2 are independently methyl or ethyl; R7, Rs, Rio and Rn are independently oxygen or hydrogen; Rg is an acyl group or hydrogen; n is an integer from 1 to 3; and m is an integer from 1 to 3 .
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