Novel non-coding heterocyclic amino acids (NCHAA) and their use as herbicides

Abstract

To provide new compounds having herbicidal activity which are more effective, less costly and environmentally safe.SOLUTION: The invention relates to a novel substituted amino acids, agricultural compositions comprising the novel substituted amino acids, and their use for controlling undesired plant growth alone or in combination with crop protection agents such as pesticides or plant growth regulators.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to novel compounds having herbicidal activity, to processes for their preparation and to their use in crop protection. [Background technology]

[0002] The fidelity of protein synthesis is crucial because it ensures the functional activity of cellular proteins. However, some non-encoded amino acids are found in proteins despite not being encoded by the genetic code. The error rate of in vivo translation is 10 -3 ~10 -4 However, high synthesis rates impose precision constraints, which lead to an increased number of erroneous cellular proteins. Thus, nascent proteins in rapidly growing organs, such as plant meristems during germination and early development, are more prone to amino acid misincorporation.

[0003] The incorporation of non-encoded amino acids into peptide chains can render proteins dysfunctional or toxic. Furthermore, it has been suggested that the herbicidal activity of the natural non-encoded amino acid metatyrosine and some of its derivatives is related to its incorporation into plant proteins. Bertin et al., 2007b; WO2017141253. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2017 / 141253 [Non-patent literature]

[0005] [Non-Patent Document 1] Bertin et al., 2007b Summary of the Invention [Problem to be solved by the invention]

[0006]

[0003] There is a constant need for new compounds that are effective in suppressing the growth of undesirable vegetation. In the most common situations, such compounds are required to selectively suppress the growth of weeds in useful crops such as cotton, rice, corn, wheat, and soybeans, to name a few. Failure to suppress weed growth in such crops can cause significant losses, reducing farm revenues and increasing costs to consumers. In other situations, herbicides that suppress the growth of all plants are desired. Examples of areas where complete suppression of all vegetation is desired are areas around railroad tracks, storage tanks, and industrial storage areas. The identification of new compounds with more effective, less costly, and environmentally safe herbicidal activity remains a long-standing unmet need. [Means for solving the problem]

[0007] The primary object of the present invention is to provide novel non-encoded amino acids as potent herbicides.

[0008] The present invention provides a compound having the following structure or a salt thereof:

[0009] [ka] During the ceremony, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of the heteroatoms is independently selected from the group consisting of N, S, and O; one or more of the carbon atoms of the ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is an EDG, at least one carbon of the ring is substituted with an EWG; when a heteroatom of the ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0010] [ka] and; R1 is selected from the group consisting of carboxyl groups, carbamoyl groups, esters of saturated or unsaturated alcohols having linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, carboxamides substituted with sulfonamides and phosphoramides; and R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides.

[0011] The present invention further provides an agricultural composition comprising a compound having the structure: or a salt thereof, and at least one agriculturally acceptable carrier.

[0012] [ka] During the ceremony, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of the heteroatoms is independently selected from the group consisting of N, S, and O; one or more of the carbon atoms of the ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is EDG, at least one carbon of the ring is substituted with EWG; when one or more heteroatoms of the ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0013] [ka] and; R1 is selected from the group consisting of carboxyl groups, carbamoyl groups, esters of saturated or unsaturated alcohols having linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sulfonamides, and carboxamides substituted with phosphoramides; and R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides.

[0014] The present invention provides a method for controlling undesirable plant growth which comprises applying to the locus of the undesirable plant growth a herbicidally effective amount of a compound having the structure: or a salt thereof.

[0015] [ka] During the ceremony, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more of the carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is EDG, at least one carbon of said ring is substituted with EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkyl and aryl amines, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0016] [ka] and; R1 is selected from the group consisting of a carboxyl group, a carbamoyl group, an ester having a saturated or unsaturated aliphatic straight, branched, cyclic or aromatic chain, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, a straight, branched, cyclic aliphatic or aromatic chain, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, a carboxamide substituted with a sulfonamide; and a phosphoramide; and R2 is selected from the group consisting of a primary amine, a secondary amine, a tertiary amine, a carboxamide, a sulfonamide, and a phosphoramide, which may be substituted.

[0017] The present invention further comprises: a. A first herbicide or a salt thereof having the structure:

[0018] [ka] [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more of the carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is EDG, at least one carbon of said ring is substituted with EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0019] [ka] and; R1 is selected from the group consisting of a carboxyl group, a carbamoyl group, a saturated or unsaturated aliphatic straight-chain, branched or cyclic chain ester, ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol; R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, and amide derivatives of carboxylic acids or inorganic acids; and b. Second herbicide to the locus of undesired plant growth, thereby inhibiting said undesired plant growth. DETAILED DESCRIPTION OF THE INVENTION

[0020] The present invention will now be described more fully hereinafter with reference to the accompanying examples, in which embodiments of the invention are shown. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.

[0021] In one embodiment, the present invention provides a compound having the structure:

[0022] [ka] During the ceremony, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is an EDG, at least one carbon of said ring is substituted with an EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0023] [ka] and; R1 is selected from the group consisting of carboxyl groups, carbamoyl groups, esters of saturated or unsaturated alcohols having linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sulfonamides, and carboxamides substituted with phosphoramides; and R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides. In one embodiment, A is selected from the group consisting of pyrrole, pyrazole, imidazole, triazole, thiophene, dithiol, trithiol, thiazole, dithiazole, trithiazolidine, thiadiazole, dithiadiazole, thiatriazole, oxazole, furan, oxathiol, pyridine, pyridazine, pyrimidine, pyrazine, triazine, thiazine, dithiazine, thiadiazine, 2H-1,3,4,5-thiatriazine, dithiadiazine, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, thiopyranopyrrole, pyrrolothiazine, pyrrolodithiazine, and thienopyridine. In yet another embodiment, A is selected from the group consisting of thiophene, 2H-1,3-dithiol, 3H-1,2-dithiol, 1H-pyrrole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 1,3-thiazole, 1,2,5-thiadiazole, 1,2,4-thiadiazole, 1,3-oxazole, furan, and pyridine. In one embodiment, the EWG is selected from the group consisting of triflyl (trifluoromethanesulfonyl), trihalide, cyano, sulfonate, nitro, ammonium, quaternary amine, aldehyde, ketone, carboxylic acid, ester, amide, and halide. As used herein, the term "electron-withdrawing group" (EWG) refers to, but is not limited to, an atom or group that withdraws electron density from a neighboring atom or aromatic ring, usually by resonance or inductive effects.As used herein, the term "electron-donating group" (EDG) refers to, but is not limited to, an atom or group that donates electron density to a neighboring atom or aromatic ring, usually by resonance or inductive effects. In one embodiment, the EDG is selected from the group consisting of phenoxide, tertiary amine, secondary amine, primary amine, ether, alkyl, phenyl, and vinyl. In yet another embodiment, R2 is a primary, secondary, or tertiary amine substituted with a group selected from hydrogen, aliphatic compounds with straight or branched chains, aliphatic compounds with non-aromatic rings, straight or branched alcohols, alcohols with non-aromatic rings, terminal carbons of phosphoric acid, phosphonic acid, phosphonate, ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol. In another embodiment, R2 is selected from the group consisting of carboxamides, sulfonamides, and phosphoramides with saturated or unsaturated straight, branched, or cyclic chains.

[0024] In one embodiment, the present invention provides a compound having the structure:

[0025] [ka] wherein R1 is COOH, COOCH3, COOC2H5, COOC3H7; R2 is NH2; R3 and R7 are independently selected from H, CF3, CCl3, Cl, and F; and R4 and R6 are independently selected from H, Cl, and Br.

[0026] In another embodiment, the present invention provides a compound having the structure:

[0027] [ka] wherein R1 is selected from COOH, COOCH3, COOC2H5, and COOC3H7; R2 is NH2; R3 and R4 are independently selected from H, Br, and Cl; and R6 and R7 are independently selected from H, Cl, NO2, CF3, and CCl3.

[0028] In yet another embodiment, the present invention provides a compound having the structure:

[0029] [ka] wherein R1 is selected from COOH, COOCH3, COOC2H5, COOC4H9, CONHCH2COOH, and COO(CH2)3CH3; R2 is selected from NH2, NHCOCH3, NHCO, and NH(CH2)2O(CH2)2)OH; R3 and R4 are independently selected from H, Cl, Br, CN, CHF2, CF3, CCl3; and R6 is H or CF3. In one embodiment, the invention provides a compound having the structure:

[0030] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is NH2; R3 and R4 are independently selected from H, Br and Cl; and R6 is selected from H, F, Cl, Br, CF3, CCl3.

[0031] In one embodiment, the present invention provides a compound having the structure:

[0032] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R4 are each independently selected from H, Br, Cl, and NH2.

[0033] In another embodiment, the present invention provides a compound having the structure:

[0034] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R4 and R6 are each independently selected from H, Br, Cl, CF3, CHF2, and CCl3.

[0035] In one embodiment, the present invention provides a compound having the structure:

[0036] [ka] wherein R1 is COOH; R2 is NH2; and R6 is H. In yet another embodiment, the present invention provides a compound having the following structure:

[0037] [ka] wherein R1 is OH; R2 is NH2; and R3 and R6 are both H.

[0038] In another embodiment, the present invention provides a compound having the structure:

[0039] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R6 is selected from H, Br, Cl, CF3, CCl3, and NH2.

[0040] In one embodiment, the present invention provides a compound having the structure:

[0041] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R6 is selected from H, Br, Cl, CF3, CCl3, and NH2.

[0042] In one embodiment, the present invention provides a compound having the structure:

[0043] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R5 are independently selected from H, Br, Cl, CF3, CCl3; and R6 is selected from CH3, OH, and NH2. In one embodiment, the present invention provides a compound having the structure:

[0044] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R5 are independently selected from H, Br, Cl, CF3, CCl3; R4 is selected from CH3, OH, and NH2.

[0045] In one embodiment, a compound having the structure:

[0046] [ka] [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more of the carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is an EDG, at least one carbon of said ring is substituted with an EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0047] [ka] and; R1 is selected from the group consisting of a carboxyl group, a carbamoyl group, an ester of a saturated or unsaturated alcohol having a straight, branched, cyclic, or aromatic chain, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, a carboxamide substituted with a straight, branched, cycloaliphatic chain, a cycloaromatic chain, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sulfonamide, and phosphoramide; and R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides.]; and an agricultural composition comprising at least one agriculturally acceptable carrier is provided. In one embodiment, A is selected from the group consisting of pyrrole, pyrazole, imidazole, triazole, thiophene, dithiol, trithiol, thiazole, dithiazole, trithiazolidine, thiadiazole, dithiadiazole, thiatriazole, oxazole, furan, oxathiol, pyridine, pyridazine, pyrimidine, pyrazine, triazine, thiazine, dithiazine, thiadiazine, 2H-1,3,4,5-thiatriazine, dithiadiazine, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, thiopyranopyrrole, pyrrolothiazine, pyrrolodithiazine, and thienopyridine. In yet another embodiment, A is selected from the group consisting of thiophene, 2H-1,3-dithiol, 3H-1,2-dithiol, 1H-pyrrole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 1,3-thiazole, 1,2,5-thiadiazole, 1,2,4-thiadiazole, 1,3-oxazole, furan, and pyridine. In one embodiment, the EWG is selected from the group consisting of triflyl (trifluoromethanesulfonyl), trihalide, cyano, sulfonate, nitro, ammonium, quaternary amine, aldehyde, ketone, carboxylic acid, ester, amide, and halide. In one embodiment, the EDG is selected from the group consisting of phenoxide, tertiary amine, secondary amine, primary amine, ether, alkyl, phenyl, and vinyl.In yet another embodiment, R2 is a primary, secondary, or tertiary amine substituted with a group selected from hydrogen, a linear or branched aliphatic compound, a non-aromatic cyclic aliphatic compound, a linear or branched alcohol, a non-aromatic cyclic alcohol, a terminal carbon of a phosphoric acid, a phosphonic acid, a phosphonate, ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol. In another embodiment, R2 is selected from the group consisting of saturated or unsaturated linear, branched, or cyclic carboxamides, sulfonamides, and phosphoramides.

[0048] In one embodiment, the composition comprises a compound having the structure:

[0049] [ka] wherein R1 is COOH, COOCH3, COOC2H5, COOC3H7; R2 is NH2; R3 and R7 are independently selected from H, CF3, CCl3, Cl, and F; and R4 and R6 are independently selected from H, Cl, and Br. In another embodiment, the composition comprises a compound having the following structure:

[0050] [ka] wherein R1 is selected from COOH, COOCH3, COOC2H5, and COOC3H7; R2 is NH2; R3 and R4 are independently selected from H, Br, and Cl; and R6 and R7 are independently selected from H, Cl, NO2, CF3, and CCl3. In yet another embodiment, the composition comprises a compound having the following structure:

[0051] [ka] wherein R1 is selected from COOH, COOCH3, COOC2H5, COOC4H9, CONHCH2COOH, and COO(CH2)3CH3; R2 is selected from NH2, NHCOCH3, NHCO, and NH(CH2)2O(CH2)2)OH; R3 and R4 are independently selected from H, Cl, Br, CN, CHF2, CF3, and CCl3; and R6 is H or CF3. In one embodiment, the composition comprises a compound having the following structure:

[0052] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is NH2; R3 and R4 are independently selected from H, Br and Cl; and R6 is selected from H, F, Cl, Br, CF3, CCl3. In one embodiment, the composition comprises a compound having the following structure:

[0053] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R4 are each independently selected from H, Br, Cl, and NH2. In another embodiment, the composition comprises a compound having the structure:

[0054] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R4 and R6 are each independently selected from H, Br, Cl, CF3, CHF2, and CCl3. In one embodiment, the composition comprises a compound having the following structure:

[0055] [ka] wherein R1 is COOH; R2 is NH2; and R6 is H. In yet another embodiment, the composition comprises a compound having the following structure:

[0056] [ka] wherein R1 is OH; R2 is NH2; and R3 and R6 are both H. In another embodiment, the composition comprises a compound having the following structure:

[0057] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; and R6 is selected from H, Br, Cl, CF3, CCl3, and NH2. In one embodiment, the composition comprises a compound having the following structure:

[0058] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; and R6 is selected from H, Br, Cl, CF3, CCl3, and NH2. In one embodiment, the composition comprises a compound having the following structure:

[0059] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R5 are independently selected from H, Br, Cl, CF3, CCl3; and R6 is selected from CH3, OH, and NH2. In one embodiment, the composition comprises a compound having the following structure:

[0060] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R5 are independently selected from H, Br, Cl, CF3, or CCl3; and R4 is selected from CH3, OH, and NH2.

[0061] In one embodiment, the agricultural composition further comprises at least one crop protection agent. In another embodiment, the at least one crop protection agent is selected from the group consisting of a fungicide, an insecticide, a herbicide, and a plant growth regulator. In yet another embodiment, the crop protection agent is a herbicide. In yet another embodiment, the crop protection agent is a plant growth regulator. In one embodiment, the at least one crop protection agent is atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl, prosulfuron, primisulfuron-methyl, dicamba, fluthiacet-methyl, pyridate, 2,4-D, clopyralid, diflufenzopyr, fluroxypyr, MCPA, MCPB, mecoprop (MCPP), metobenzuron, thifensulfuron-methyl, aclonifen, EPTC, glyphosate, glufosinate, sulfosate, cyanazine, propaquizafop, metamitron, pyramine, phenmedipham, desmedipham, ethofumesate, triasulfuron, chloridazon, lenacil, triallate, fluazifop, sethoxydim, quizalofop, clopyralid, clethodim, oxasulfuron, acifluorfen, benazolin-ethyl, sulfentrazone, chlorimuron-ethyl, chloransulam-methyl, fomesafen, imazamox, imazaquin, imazethapyr, imazapyr, lactofen, fenoxaprop (p-ethyl), thidiazuron, tribu Phos, trifluralin, dimetachlor, napropamide, quinmerac, metazachlor, carbetamide, dimefuron, propyzamide, ethametsulfuron-methyl, tebutam, fluometuron, prometryn, norflurazon, pyrithiobac-sodium, MSMA, DSMA, diuron, flurochloridone, dithiopyr, thiazopyr, oxyfluorfen, ethalfluralin, clodinafop, amidosulfuron, diclofop-methyl, diflufenican, ethoxysulfuron, fentrazamide, flazasulfuron, florasulam, fluazolate, flucarbazone, flupyrsulfuron-methyl sodium, flutamone, iodosulfuron, isoproturon, chlortoluron, chlorsulfuron, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, 2,4-DB, 2,4-DP, Bifenox, Flamprop-M, Imazamethabenz-methyl, Ioxynil, Trakoxydim, Fluoroglycofen-ethyl, Methabenzthiazuron, Isoxaben, Prosulfocarb, Difenzoquat-methylsulfate, Pretilachlor, Cinosulfuron, Fenclorim, Bensulfuron-methyl, Imazosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Esprocarb, Mefenacet, Molinate, Propanil, Pyrazolate, Cyhalofop-butyl, Bispyribac-sodium, Pyriminobac-methyl, Caffentrol, Oxadiargyl, Oxadiazon, Bromobutide, MY-100, Dimron, NB 061, MK243, HW-52, AC 014, ametryn, hexazinone, asulam, azafenidin, tebuthiuron, ethametsurfuron-methyl, or a combination thereof.

[0062] In one embodiment of the present invention, there is provided a method for inhibiting unwanted plant growth, comprising administering to a locus of the unwanted plant growth a compound having the following structure or a salt thereof:

[0063] [ka] [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is EDG, at least one carbon of said ring is substituted with EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0064] [ka] and; wherein R1 is selected from the group consisting of a carboxyl group, a carbamoyl group, an ester of a saturated or unsaturated alcohol having a straight, branched, cyclic, or aromatic chain, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, a carboxamide substituted with a straight, branched, cycloaliphatic chain, a cycloaromatic chain, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sulfonamide, and phosphoramide; and R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides; and at least one agriculturally acceptable carrier. In one embodiment, A is selected from the group consisting of pyrrole, pyrazole, imidazole, triazole, thiophene, dithiol, trithiol, thiazole, dithiazole, trithiazolidine, thiadiazole, dithiadiazole, thiatriazole, oxazole, furan, oxathiol, pyridine, pyridazine, pyrimidine, pyrazine, triazine, thiazine, dithiazine, thiadiazine, 2H-1,3,4,5-thiatriazine, dithiadiazine, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, thiopyranopyrrole, pyrrolothiazine, pyrrolodithiazine, and thienopyridine. In yet another embodiment, A is selected from the group consisting of thiophene, 2H-1,3-dithiol, 3H-1,2-dithiol, 1H-pyrrole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 1,3-thiazole, 1,2,5-thiadiazole, 1,2,4-thiadiazole, 1,3-oxazole, furan, and pyridine. In one embodiment, the EWG is selected from the group consisting of triflyl (trifluoromethanesulfonyl), trihalide, cyano, sulfonate, nitro, ammonium, quaternary amine, aldehyde, ketone, carboxylic acid, ester, amide, and halide. In one embodiment, the EDG is selected from the group consisting of phenoxide, tertiary amine, secondary amine, primary amine, ether, alkyl, phenyl, and vinyl.In yet another embodiment, R2 is selected from the group consisting of hydrogen, aliphatic compounds having a straight or branched chain, aliphatic compounds having a non-aromatic ring, a straight or branched chain alcohol, an alcohol having a non-aromatic ring, a terminal carbon of a carboxylic acid, a phosphoric acid, a phosphonic acid, a phosphonate, a primary, secondary, and tertiary amine substituted with a group selected from ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol. In another embodiment, R2 is selected from the group consisting of carboxamides, sulfonamides, and phosphoramides having a saturated or unsaturated straight, branched, or cyclic chain.

[0065] In one embodiment, the composition comprises a compound having the structure:

[0066] [ka] wherein R1 is COOH, COOCH3, COOC2H5, COOC3H7; R2 is NH2; R3 and R7 are independently selected from H, CF3, CCl3, Cl, and F; and R4 and R6 are independently selected from H, Cl, and Br.

[0067] In another embodiment, the composition comprises a compound having the structure:

[0068] [ka] wherein R1 is selected from COOH, COOCH3, COOC2H5, and COOC3H7; R2 is NH2; R3 and R4 are independently selected from H, Br, and Cl; and R6 and R7 are independently selected from H, Cl, NO2, CF3, and CCl3.

[0069] In yet another embodiment, the composition comprises a compound having the structure:

[0070] [ka] wherein R1 is selected from COOH, COOCH3, COOC2H5, COOC4H9, CONHCH2COOH, and COO(CH2)3CH3; R2 is selected from NH2, NHCOCH3, NHCO, and NH(CH2)2O(CH2)2)OH; R3 and R4 are independently selected from H, Cl, Br, CN, CHF2CF3, CCl3; and R6 is H or CF3. In one embodiment, the composition comprises a compound having the following structure:

[0071] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is NH2; R3 and R4 are independently selected from H, Br and Cl; and R6 is selected from H, F, Cl, Br, CF3, CCl3.

[0072] In one embodiment, the composition comprises a compound having the structure:

[0073] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R4 are each independently selected from H, Br, Cl, and NH2.

[0074] In another embodiment, the composition comprises a compound having the structure:

[0075] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R4 and R6 are each independently selected from H, Br, Cl, CF3, CHF2, and CCl3.

[0076] In one embodiment, the composition comprises a compound having the structure:

[0077] [ka] wherein R1 is COOH; R2 is NH2; and R6 is H.

[0078] In yet another embodiment, the composition comprises a compound having the structure:

[0079] [ka] wherein R1 is OH; R2 is NH2; and R3 and R6 are both H.

[0080] In another embodiment, the composition comprises a compound having the structure:

[0081] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; and R6 is selected from H, Br, Cl, CF3, CCl3, and NH2. In one embodiment, the composition comprises a compound having the following structure:

[0082] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; and R6 is selected from H, Br, Cl, CF3, CCl3, and NH2. In one embodiment, the composition comprises a compound having the following structure:

[0083] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R5 are independently selected from H, Br, Cl, CF3, CCl3; and R6 is selected from CH3, OH, and NH2. In one embodiment, the composition comprises a compound having the following structure:

[0084] [ka] In the formula, R1 is COOH, COOCH3, COOC2H5, COOC5H 11 and COO(CH2)2(CH2)2CH3; R2 is selected from NH2, NHCOCH3, or NHCOC2H5; R3 and R5 are independently selected from H, Br, Cl, CF3, CCl3; and R4 is selected from CH3, OH, and NH2.

[0085] In one embodiment, the method further comprises applying at least one crop protection agent to the locus of undesired plant growth. In one embodiment, the crop protection agent is selected from the group consisting of herbicides, fungicides, insecticides, and plant growth regulators. In one embodiment, the crop protection agent is a herbicide. In one embodiment, the crop protection agent is an amino acid synthesis inhibitor herbicide. In another embodiment, the amino acid synthesis inhibitor herbicide is selected from the group consisting of sulfonylurea herbicides, imidazolinone herbicides, sulfonamide herbicides, and amino acid derivatives, or combinations thereof. In one embodiment, the amino acid synthesis inhibitor herbicide is selected from the group consisting of imazamox, imazapic, imazethapyr, imazaquin, imazapyr, and imazamethabenz, or combinations thereof. In one embodiment, the amino acid synthesis inhibitor herbicide is selected from the group consisting of chlorimuron, primisulfuron, thifensulfuron, triasulfuron, nicosulfuron, metsulfuron, tribenuron, rimsulfuron, and triflusulfuron, or combinations thereof. In another embodiment, the amino acid synthesis inhibitor herbicide is glyphosate. In yet another embodiment, the crop protection agent is a plant growth regulator. In one embodiment, the plant growth regulator is selected from the group consisting of dicamba, 2,4-D, clopyralid, and fluroxypyr.

[0086] In one embodiment, the present invention provides a method for treating a locus of unwanted plant growth with: a. A first herbicide or salt thereof having the following structure:

[0087] [ka] [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is EDG, at least one carbon of said ring is substituted with EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0088] [ka] and; R1 is selected from the group consisting of a carboxyl group, a carbamoyl group, a saturated or unsaturated aliphatic ester having a straight, branched or cyclic chain, ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol; R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, and amide derivatives of carboxylic acids or inorganic acids; and b. A second herbicide to effectively suppress undesirable plant growth. and a method for controlling undesirable plant growth comprising applying a

[0089] In one embodiment, the second herbicide is an amino acid synthesis inhibitor herbicide. In one embodiment, the second herbicide is selected from the group consisting of sulfonylurea herbicides, imidazolinone herbicides, sulfonamide herbicides, and amino acid derivatives. In another embodiment, the second herbicide is selected from the group consisting of imazamox, imazapic, imazethapyr, imazaquin, imazapyr, imazamethabenz, chlorimuron, primisulfuron, thifensulfuron, triasulfuron, nicosulfuron, metsulfuron, tribenuron, rimsulfuron, triflusuron, and glyphosate. In one embodiment, the second herbicide is atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl, prosulfuron, primisulfuron-methyl, dicamba, fluthiacet-methyl, pyridate, 2,4-D, clopyralid, diflufenzopyr, fluroxypyr, MCPA, MCPB, mecoprop (MCPP), metobenzuron, thifensulfuron-methyl, aclonifen, EPTC, glyphosate, glufosinate, sulfosate, cyanazine, propaquizafop, metamitron, pyramine, phenmedipham, desmedipham, ethofumesate, triasulfuron, chloridazon, lenacil, triallate, fluazifop, sethoxydim, quizalofop, clopyralid, clethodim, oxasulfuron, acifluorfen, benazolin-ethyl, sulfentrazone, chlorimuron-ethyl, chloransulam-methyl, fomesafen, imazamox, imazaquin, imazethapyr, imazapyr, lactofen, fenoxaprop (p-ethyl), thidiazuron, tribu Phos, trifluralin, dimetachlor, napropamide, quinmerac, metazachlor, carbetamide, dimefuron, propyzamide, ethametsulfuron-methyl, tebutam, fluometuron, prometryn, norflurazon, pyrithiobac-sodium, MSMA, DSMA, diuron, flurochloridone, dithiopyr, thiazopyr, oxyfluorfen, ethalfluralin, clodinafop, amidosulfuron, diclofop-methyl, diflufenican, ethoxysulfuron, fentrazamide, flazasulfuron, florasulam, fluazolate, flucarbazone, flupyrsulfuron-methyl sodium, flutamone, iodosulfuron, isoproturon, chlortoluron, chlorsulfuron, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, 2,4-DB, 2,4-DP, Bifenox, Flamprop-M, Imazamethabenz-methyl, Ioxynil, Trakoxydim, Fluoroglycofen-ethyl, Methabenzthiazuron, Isoxaben, Prosulfocarb, Difenzoquat-methylsulfate, Pretilachlor, Cinosulfuron, Fenclorim, Bensulfuron-methyl, Imazosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Esprocarb, Mefenacet, Molinate, Propanil, Pyrazolate, Cyhalofop-butyl, Bispyribac-sodium, Pyriminobac-methyl, Caffentrol, Oxadiargyl, Oxadiazon, Bromobutide, MY-100, Dimron, NB 061, MK243, HW-52, AC 014, ametryn, hexazinone, asulam, azafenidin, tebuthiuron, and ethametsurfuron-methyl. In one embodiment, the method for controlling undesirable plant growth further comprises controlling a third herbicide or plant growth regulator.

[0090] In one embodiment, the present invention provides a method for producing a pharmaceutical composition comprising: a. A compound having the following structure or a salt thereof:

[0091] [ka] [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; one or more carbon atoms of said ring may be substituted with R3, R4, R6, and R7; each of R3, R4, R6, or R7 is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); when R3, R4, R6, or R7 is EDG, at least one carbon of said ring is substituted with EWG; when one or more heteroatoms of said ring is N or S, each may be independently substituted with R3, R4, R6, and R7; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is

[0092] [ka] and; R1 is selected from the group consisting of carboxyl groups, carbamoyl groups, esters of saturated or unsaturated alcohols having linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, carboxamides substituted with sulfonamides and phosphoramides; and R2 is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides. b. Atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl, prosulfuron, primisulfuron-methyl , dicamba, fluthiacet-methyl, pyridate, 2,4-D, clopyralid, diflufenzopyr, fluroxypyr, MCPA, MCPB, mecoprop (MCPP), metobenzuron, thifensulfuron-methyl, aclonifen, EPTC, glyphosate, glufosinate, sulfosate, cyanazine, propaquizafop, metamitron, pyramine, phenmedipham, desmedipham, ethofumesate, triasulfuron, chloridazon, lenacil, triallate, fluazifop, sethoxydim, quizalofop, clopyralid, chloazon Letodim, oxasulfuron, acifluorfen, benazolin-ethyl, sulfentrazone, chlorimuron-ethyl, chloransulam-methyl, fomesafen, imazamox, imazaquin, imazethapyr, imazapyr, lactofen, fenoxaprop (P-ethyl), thidiazuron, tribufos, trifluralin, dimetachlor, napropamide, quinmerac, metazachlor, carbetamide, dimefuron, propyzamide, ethametsulfuron-methyl, tebutam, fluometuron, prometryn, norflurazon, pyrithiobac-sodium um, MSMA, DSMA, diuron, flurochloridone, dithiopyr, thiazopyr, oxyfluorfen, ethalfluralin, clodinafop, amidosulfuron, diclofop-methyl, diflufenican, ethoxysulfuron, fentrazamide, flazasulfuron, florasulam, fluazolate, flucarbazone, flupyrsulfuron-methyl sodium, flutamone, iodosulfuron, isoproturon, chlortoluron, chlorsulfuron, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, 2,4-DB, 2,4-DP, Bifenox, Flamprop-M, Imazamethabenz-methyl, Ioxynil, Trakoxydim, Fluoroglycofen-ethyl, Methabenzthiazuron, Isoxaben, Prosulfocarb, Difenzoquat-methylsulfate, Pretilachlor, Cinosulfuron, Fenclorim, Bensulfuron-methyl, Imazosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Esprocarb, Mefenacet, Molinate, Propanil, Pyrazolate, Cyhalofop-butyl, Bispyribac-sodium, Pyriminobac-methyl, Caffentrol, Oxadiargyl, Oxadiazon, Bromobutide, MY-100, Dimron, NB 061, MK243, HW-52, AC 014, ametryn, hexazinone, asulam, azafenidin, tebuthiuron, ethametsurfuron-methyl or at least one herbicide selected from the group consisting of, or a combination thereof; and c. at least one agriculturally acceptable carrier The present invention provides a composition for suppressing undesirable plant growth comprising a mixture of:

[0093] In one embodiment, A is selected from the group consisting of pyrrole, pyrazole, imidazole, triazole, thiophene, dithiol, trithiol, thiazole, dithiazole, trithiazolidine, thiadiazole, dithiadiazole, thiatriazole, oxazole, furan, oxathiol, pyridine, pyridazine, pyrimidine, pyrazine, triazine, thiazine, dithiazine, thiadiazine, 2H-1,3,4,5-thiatriazine, dithiadiazine, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, thiopyranopyrrole, pyrrolothiazine, pyrrolodithiazine, and thienopyridine. In yet another embodiment, A is selected from the group consisting of thiophene, 2H-1,3-dithiol, 3H-1,2-dithiol, 1H-pyrrole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 1,3-thiazole, 1,2,5-thiadiazole, 1,2,4-thiadiazole, 1,3-oxazole, furan, and pyridine. In one embodiment, the EWG is selected from the group consisting of triflyl (trifluoromethanesulfonyl), trihalide, cyano, sulfonate, nitro, ammonium, quaternary amine, aldehyde, ketone, carboxylic acid, ester, amide, and halide. In one embodiment, the EDG is selected from the group consisting of phenoxide, tertiary amine, secondary amine, primary amine, ether, alkyl, phenyl, and vinyl. In yet another embodiment, R2 is a primary, secondary, or tertiary amine substituted with a group selected from hydrogen, a linear or branched aliphatic compound, a non-aromatic cyclic aliphatic compound, a linear or branched alcohol, a non-aromatic cyclic alcohol, a terminal carbon of a phosphoric acid, a phosphonic acid, a phosphonate, ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol. In another embodiment, R2 is selected from the group consisting of saturated or unsaturated linear, branched, or cyclic carboxamides, sulfonamides, and phosphoramides.

[0094] According to some embodiments, the present invention provides 2-amino-3-(thiophen-2-yl)propanoic acid; 2-amino-3-(thiophen-3-yl)propanoic acid; 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine; 2 -Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid;3-Amino-3-(4-bromothiophen-3-yl)propanoic acid;2-Amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid;Butyl 2-amino-3-(thiophen-3-yl)propanoate;2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(2-chlorothiophene) 2-Amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid;2-Amino-3-(5-chlorothiophen-3-yl)propanoic acid;2-Amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,3-thiazol-5-yl)propanoic acid;2-Amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid;2-Amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(2,5-dichloro-4-(trifluoromethyl)thiophene-3-yl) ...Methyl 2 -Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;[2-(Carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid;2-Amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid;2-Amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid;2-Amino-3-(furan-3-yl)propanoic acid;2-Amino-3-(1,3-oxazol-4-yl)propanoic acid;2-Formamido-3-(thiophen-3-yl)propanoic acid;Methyl 2-amino-3-(thiophen-3-yl)propanoate;Ethyl 2-amino-3-(thiophen-3-yl)propanoate 2-Amino-3-(thiophen-3-yl)propanamido]acetic acid;2-Amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide;Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate;2-Butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;2-Amino-3-(2,5-dibromothiophen-3-yl)propanoic acid;2-Amino-3-(5-nitrothiophen-3-yl)propanoate 2-Amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid;(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid;2-Amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(5-chloro-2- 2-Amino-3-(2-bromothiophen-3-yl)propanoic acid;2-Amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid;2-Amino-3-(thiolan-3-yl)propanoic acid;[2-Amino-2-(thiophen-3-yl)ethyl]phosphonic acid;2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid;3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid;2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid;Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;Methyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;2-(2-Methoxyethoxy)ethyl-2-acetamido 2-Amino-3-(thiophen-3-yl)propanoate;Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate;Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate;Propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate;4-(2-acetamido 2-(2-Ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate;Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)thiophene]-3-sulfonyl 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate;2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl];2-Amino-3-(pyridazin-4-yl)propanoic acid;2-Amino-3-(pyridin-4-yl)propanoic acid;2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-Hydroxy-3-pyridinyl)alanine;2-Amino-3-(5-methylpyridin-3-yl)propanoic acid;2-Amino-3-(4-aminopyridin-2-yl)propanoic acid;2-Amino-3-(2-aminopyridin-4-yl)propanoic acid;2-Amino-3-(6-aminopyridin-2-yl)propanoic acid;2-Amino-3-(5-aminopyridin-3-yl)propanoic acid;2-Amino-3-(5-sulfanylpyridin-3-yl)propanoic acid;2-Amino-3-(2-sulfanylpyridin-4-yl)propanoic acid;2- Amino-3-(pyrimidin-5-yl)propanoic acid;2-Amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid;2-Amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride;2-Amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid;2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid;2-Amino-3-(pyrazin-2-yl)propanoic acid;2-Amino-3-(5-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2 ,5-Dichloropyridin-3-yl)propanoic acid;2-Amino-3-(pyrimidin-4-yl)propanoic acid;2-Amino-3-(5-fluoropyridin-3-yl)propanoic acid;2-Amino-3-(6-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-difluoropyridin-4-yl)propanoic acid;2-Amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid Panic acid;2-amino-3-(2-bromopyridin-4-yl)propanoic acid;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid;2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid;2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid;2-amino-3-(5-(trifluoromethyl)pyridin-3-yl)propanoic acid;2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid;2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid;2-Amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid;2-Amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid 2-Amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate;2-Amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate;2-Amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid;Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid 2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoate;Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate;Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate;2-Amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid;2-Amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid;Methyl 2-amino-3-(2-bromopyridin-4-yl) Propanoate;3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium;3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium;2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid;Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate;Ethyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Ethyl-2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate;2-(2-methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;2-(2-ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium;2-Amino-3-[2-(trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride[H Cl];Ethyl 3-[(2-bromopyridin-4-yl)oxy]-2-acetamidopropanoate;Ethyl 2-acetamido-3-(pyridin-4-yloxy)propanoate;2-Amino-4-(1H-pyrrol-3-yl)butanoic acid;2-Amino-3-(1H-pyrrol-2-yl)propanoic acid;2-Amino-3-(1H-pyrrol-3-yl)propanoic acid;2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid;(2S)-2-Hydroxy-3-(1 H-Imidazol-4-yl)propanoic acid;Ethyl 2-{[(benzyloxy)carbonyl]amino}-3-(1H-1,2,4-triazol-3-yl)propanoate;2-Amino-3-(4-methyl-4H-1,2,4-triazol-3-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,4-triazol-5-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride;2- Provided is a compound or a salt thereof selected from the group consisting of amino-3-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)propanoic acid hydrochloride; 2-amino-3-(dimethyl-4H-1,2,4-triazol-3-yl)propanoic acid hydrochloride; (2S)-2-amino-3-[5-(trifluoromethyl)-1H-pyrazol-4-yl]propanoic acid; and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate.

[0095] According to some embodiments, the present invention provides 2-amino-3-(thiophen-2-yl)propanoic acid; 2-amino-3-(thiophen-3-yl)propanoic acid; 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine; 2 -Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid;3-Amino-3-(4-bromothiophen-3-yl)propanoic acid;2-Amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid;Butyl 2-amino-3-(thiophen-3-yl)propanoate;2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(2-chlorothiophene) 2-Amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid;2-Amino-3-(5-chlorothiophen-3-yl)propanoic acid;2-Amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,3-thiazol-5-yl)propanoic acid;2-Amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid;2-Amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(2,5-dichloro-4-(trifluoromethyl)thiophene-3-yl) ...Methyl 2 -Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;[2-(Carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid;2-Amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid;2-Amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid;2-Amino-3-(furan-3-yl)propanoic acid;2-Amino-3-(1,3-oxazol-4-yl)propanoic acid;2-Formamido-3-(thiophen-3-yl)propanoic acid;Methyl 2-amino-3-(thiophen-3-yl)propanoate;Ethyl 2-amino-3-(thiophen-3-yl)propanoate 2-Amino-3-(thiophen-3-yl)propanamido]acetic acid;2-Amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide;Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate;2-Butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;2-Amino-3-(2,5-dibromothiophen-3-yl)propanoic acid;2-Amino-3-(5-nitrothiophen-3-yl)propanoate 2-Amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid;(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid;2-Amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(5-chloro-2- 2-Amino-3-(2-bromothiophen-3-yl)propanoic acid;2-Amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid;2-Amino-3-(thiolan-3-yl)propanoic acid;[2-Amino-2-(thiophen-3-yl)ethyl]phosphonic acid;2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid;3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid;2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid;Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;Methyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;2-(2-Methoxyethoxy)ethyl-2-acetamido 2-Amino-3-(thiophen-3-yl)propanoate;Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate;Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate;Propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate;4-(2-acetamido 2-(2-Ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate;Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)thiophene]-3-sulfonyl 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate;2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl];2-Amino-3-(pyridazin-4-yl)propanoic acid;2-Amino-3-(pyridin-4-yl)propanoic acid;2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-Hydroxy-3-pyridinyl)alanine;2-Amino-3-(5-methylpyridin-3-yl)propanoic acid;2-Amino-3-(4-aminopyridin-2-yl)propanoic acid;2-Amino-3-(2-aminopyridin-4-yl)propanoic acid;2-Amino-3-(6-aminopyridin-2-yl)propanoic acid;2-Amino-3-(5-aminopyridin-3-yl)propanoic acid;2-Amino-3-(5-sulfanylpyridin-3-yl)propanoic acid;2-Amino-3-(2-sulfanylpyridin-4-yl)propanoic acid;2- Amino-3-(pyrimidin-5-yl)propanoic acid;2-Amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid;2-Amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride;2-Amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid;2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid;2-Amino-3-(pyrazin-2-yl)propanoic acid;2-Amino-3-(5-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2 ,5-Dichloropyridin-3-yl)propanoic acid;2-Amino-3-(pyrimidin-4-yl)propanoic acid;2-Amino-3-(5-fluoropyridin-3-yl)propanoic acid;2-Amino-3-(6-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-difluoropyridin-4-yl)propanoic acid;2-Amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid Panic acid;2-amino-3-(2-bromopyridin-4-yl)propanoic acid;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid;2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid;2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid;2-amino-3-(5-(trifluoromethyl)pyridin-3-yl)propanoic acid;2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid;2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid;2-Amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid;2-Amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid 2-Amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate;2-Amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate;2-Amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid;Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid 2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoate;Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate;Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate;2-Amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid;2-Amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid;Methyl 2-amino-3-(2-bromopyridin-4-yl) Propanoate;3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium;3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium;2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid;Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate;Ethyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Ethyl-2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate;2-(2-Methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;2-(2-Ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;5-(2-Amino-2-carboxyethyl)-1-methylpyrimidin-1-ium;2-Amino-3-[2-(trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride [HCl];Ethyl 3-[(2-Bromopyridin-4-yl)oxy]-2-acetamidopropanoate;Ethyl 2-acetamido-3-(pyridin-4-yloxy)propanoate;2-Amino-4-(1H-pyrrol-3-yl)butanoic acid;2-Amino-3-(1H-pyrrol-2-yl)propanoic acid;2-Amino-3-(1H-pyrrol-3-yl)propanoic acid;2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid;(2S)-2-Hydroxy-3-(1H-imidazol-4-yl) Propanoic acid;Ethyl 2-{[(benzyloxy)carbonyl]amino}-3-(1H-1,2,4-triazol-3-yl)propanoate;2-Amino-3-(4-methyl-4H-1,2,4-triazol-3-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,4-triazol-5-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride;2-Amino-3-(2-methyl-2H-1,2,3 and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate, or a salt thereof, and at least one agriculturally acceptable carrier.

[0096] According to some embodiments, the present invention provides 2-amino-3-(thiophen-2-yl)propanoic acid; 2-amino-3-(thiophen-3-yl)propanoic acid; 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine; 2 -Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid;3-Amino-3-(4-bromothiophen-3-yl)propanoic acid;2-Amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid;Butyl 2-amino-3-(thiophen-3-yl)propanoate;2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(2-chlorothiophene) 2-Amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid;2-Amino-3-(5-chlorothiophen-3-yl)propanoic acid;2-Amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,3-thiazol-5-yl)propanoic acid;2-Amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid;2-Amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(2,5-dichloro-4-(trifluoromethyl)thiophene-3-yl) ...Methyl 2 -Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;[2-(Carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid;2-Amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid;2-Amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid;2-Amino-3-(furan-3-yl)propanoic acid;2-Amino-3-(1,3-oxazol-4-yl)propanoic acid;2-Formamido-3-(thiophen-3-yl)propanoic acid;Methyl 2-amino-3-(thiophen-3-yl)propanoate;Ethyl 2-amino-3-(thiophen-3-yl)propanoate 2-Amino-3-(thiophen-3-yl)propanamido]acetic acid;2-Amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide;Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate;2-Butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;2-Amino-3-(2,5-dibromothiophen-3-yl)propanoic acid;2-Amino-3-(5-nitrothiophen-3-yl)propanoate 2-Amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid;(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid;2-Amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(5-chloro-2- 2-Amino-3-(2-bromothiophen-3-yl)propanoic acid;2-Amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid;2-Amino-3-(thiolan-3-yl)propanoic acid;[2-Amino-2-(thiophen-3-yl)ethyl]phosphonic acid;2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid;3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid;2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid;Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;Methyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;2-(2-Methoxyethoxy)ethyl-2-acetamido 2-Amino-3-(thiophen-3-yl)propanoate;Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate;Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate;Propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate;4-(2-acetamido 2-(2-Ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate;Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)thiophene]-3-sulfonyl 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate;2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl];2-Amino-3-(pyridazin-4-yl)propanoic acid;2-Amino-3-(pyridin-4-yl)propanoic acid;2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-Hydroxy-3-pyridinyl)alanine;2-Amino-3-(5-methylpyridin-3-yl)propanoic acid;2-Amino-3-(4-aminopyridin-2-yl)propanoic acid;2-Amino-3-(2-aminopyridin-4-yl)propanoic acid;2-Amino-3-(6-aminopyridin-2-yl)propanoic acid;2-Amino-3-(5-aminopyridin-3-yl)propanoic acid;2-Amino-3-(5-sulfanylpyridin-3-yl)propanoic acid;2-Amino-3-(2-sulfanylpyridin-4-yl)propanoic acid;2- Amino-3-(pyrimidin-5-yl)propanoic acid;2-Amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid;2-Amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride;2-Amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid;2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid;2-Amino-3-(pyrazin-2-yl)propanoic acid;2-Amino-3-(5-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2 ,5-Dichloropyridin-3-yl)propanoic acid;2-Amino-3-(pyrimidin-4-yl)propanoic acid;2-Amino-3-(5-fluoropyridin-3-yl)propanoic acid;2-Amino-3-(6-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-difluoropyridin-4-yl)propanoic acid;2-Amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid Panic acid;2-amino-3-(2-bromopyridin-4-yl)propanoic acid;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid;2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid;2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid;2-amino-3-(5-(trifluoromethyl)pyridin-3-yl)propanoic acid;2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid;2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid;2-Amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid;2-Amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid 2-Amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate;2-Amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate;2-Amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid;Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid 2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoate;Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate;Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate;2-Amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid;2-Amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid;Methyl 2-amino-3-(2-bromopyridin-4-yl) Propanoate;3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium;3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium;2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid;Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate;Ethyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Ethyl-2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate;2-(2-methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;2-(2-ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium;2-Amino-3-[2-(trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride [HCl];Ethyl 3-[ (2-Bromopyridin-4-yl)oxy]-2-acetamidopropanoate;Ethyl 2-acetamido-3-(pyridin-4-yloxy)propanoate;2-Amino-4-(1H-pyrrol-3-yl)butanoic acid;2-Amino-3-(1H-pyrrol-2-yl)propanoic acid;2-Amino-3-(1H-pyrrol-3-yl)propanoic acid;2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid;(2S)-2-Hydroxy-3-(1H-imidazol-4-yl)propanoic acid;Ethyl 2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride;2-Amino-3-(2-methyl-2H-1,2,3,4-tetrazole-5 and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate, or a salt thereof, to the locus of the undesired plant growth.

[0097] According to some embodiments, the present invention provides a) 2-amino-3-(thiophen-2-yl)propanoic acid; 2-amino-3-(thiophen-3-yl)propanoic acid; 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine ;2-Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid;3-Amino-3-(4-bromothiophen-3-yl)propanoic acid;2-Amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid;Butyl 2-amino-3-(thiophen-3-yl)propanoate;2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(2-chlorothio 2-Amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid;2-Amino-3-(5-chlorothiophen-3-yl)propanoic acid;2-Amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,3-thiazol-5-yl)propanoic acid;2-Amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid;2-Amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid;Methyl 2 -Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;[2-(Carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid;2-Amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid;2-Amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid;2-Amino-3-(furan-3-yl)propanoic acid;2-Amino-3-(1,3-oxazol-4-yl)propanoic acid;2-Formamido-3-(thiophen-3-yl)propanoic acid;Methyl 2-amino-3-(thiophen-3-yl)propanoate;Ethyl 2-amino-3-(thiophen-3-yl)propanoate 2-Amino-3-(thiophen-3-yl)propanamido]acetic acid;2-Amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide;Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate;2-Butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;2-Amino-3-(2,5-dibromothiophen-3-yl)propanoic acid;2-Amino-3-(5-nitrothiophen-3-yl)propanoate 2-Amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid;(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid;2-Amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(5-chloro-2- 2-Amino-3-(2-bromothiophen-3-yl)propanoic acid;2-Amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid;2-Amino-3-(thiolan-3-yl)propanoic acid;[2-Amino-2-(thiophen-3-yl)ethyl]phosphonic acid;2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid;3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid;2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid;Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;Methyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;2-(2-Methoxyethoxy)ethyl-2-acetamido 2-Amino-3-(thiophen-3-yl)propanoate;Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate;Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate;Propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate;4-(2-acetamido 2-(2-Ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate;Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)thiophene]-3-sulfonyl 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate;2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl];2-Amino-3-(pyridazin-4-yl)propanoic acid;2-Amino-3-(pyridin-4-yl)propanoic acid;2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-Hydroxy-3-pyridinyl)alanine;2-Amino-3-(5-methylpyridin-3-yl)propanoic acid;2-Amino-3-(4-aminopyridin-2-yl)propanoic acid;2-Amino-3-(2-aminopyridin-4-yl)propanoic acid;2-Amino-3-(6-aminopyridin-2-yl)propanoic acid;2-Amino-3-(5-aminopyridin-3-yl)propanoic acid;2-Amino-3-(5-sulfanylpyridin-3-yl)propanoic acid;2-Amino-3-(2-sulfanylpyridin-4-yl)propanoic acid;2- Amino-3-(pyrimidin-5-yl)propanoic acid;2-Amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid;2-Amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride;2-Amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid;2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid;2-Amino-3-(pyrazin-2-yl)propanoic acid;2-Amino-3-(5-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2 ,5-Dichloropyridin-3-yl)propanoic acid;2-Amino-3-(pyrimidin-4-yl)propanoic acid;2-Amino-3-(5-fluoropyridin-3-yl)propanoic acid;2-Amino-3-(6-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-difluoropyridin-4-yl)propanoic acid;2-Amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid Panic acid;2-amino-3-(2-bromopyridin-4-yl)propanoic acid;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid;2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid;2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid;2-amino-3-(5-(trifluoromethyl)pyridin-3-yl)propanoic acid;2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid;2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid;2-Amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid;2-Amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid 2-Amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate;2-Amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate;2-Amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid;Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid 2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoate;Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate;Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate;2-Amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid;2-Amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid;Methyl 2-amino-3-(2-bromopyridin-4-yl) Propanoate;3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium;3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium;2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid;Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate;Ethyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Ethyl 2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate;2-(2-methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;2-(2-ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium;2-Amino-3-[2-(trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride [HCl];Ethyl 3-[(2-bu 2-Amino-3-(1H-pyrrol-2-yl)propanoic acid;2-Amino-3-(1H-pyrrol-3-yl)propanoic acid;2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid;(2S)-2-Hydroxy-3-(1H-imidazol-4-yl)propanoic acid;Ethyl 2-{[( Benzyloxy)carbonyl]amino}-3-(1H-1,2,4-triazol-3-yl)propanoate;2-Amino-3-(4-methyl-4H-1,2,4-triazol-3-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,4-triazol-5-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride;2-Amino-3-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)propanoic acid salt and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate; a) a second herbicide; and c) at least one agriculturally acceptable carrier.

[0098] According to some embodiments, the present invention provides a) 2-amino-3-(thiophen-2-yl)propanoic acid; 2-amino-3-(thiophen-3-yl)propanoic acid; 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine ;2-Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid;3-Amino-3-(4-bromothiophen-3-yl)propanoic acid;2-Amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid;Butyl 2-amino-3-(thiophen-3-yl)propanoate;2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(2-chlorothio 2-Amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid;2-Amino-3-(5-chlorothiophen-3-yl)propanoic acid;2-Amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,3-thiazol-5-yl)propanoic acid;2-Amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid;2-Amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid;Methyl 2 -Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;[2-(Carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid;2-Amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid;2-Amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid;2-Amino-3-(furan-3-yl)propanoic acid;2-Amino-3-(1,3-oxazol-4-yl)propanoic acid;2-Formamido-3-(thiophen-3-yl)propanoic acid;Methyl 2-amino-3-(thiophen-3-yl)propanoate;Ethyl 2-amino-3-(thiophen-3-yl)propanoate 2-Amino-3-(thiophen-3-yl)propanamido]acetic acid;2-Amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide;Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate;2-Butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;2-Amino-3-(2,5-dibromothiophen-3-yl)propanoic acid;2-Amino-3-(5-nitrothiophen-3-yl)propanoate 2-Amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid;(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid;2-Amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(5-chloro-2- 2-Amino-3-(2-bromothiophen-3-yl)propanoic acid;2-Amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid;2-Amino-3-(thiolan-3-yl)propanoic acid;[2-Amino-2-(thiophen-3-yl)ethyl]phosphonic acid;2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid;3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid;2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid;Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;Methyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;2-(2-Methoxyethoxy)ethyl-2-acetamido 2-Amino-3-(thiophen-3-yl)propanoate;Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate;Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate;Propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate;4-(2-acetamido 2-(2-Ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate;Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)thiophene]-3-sulfonyl 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate;2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl];2-Amino-3-(pyridazin-4-yl)propanoic acid;2-Amino-3-(pyridin-4-yl)propanoic acid;2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-Hydroxy-3-pyridinyl)alanine;2-Amino-3-(5-methylpyridin-3-yl)propanoic acid;2-Amino-3-(4-aminopyridin-2-yl)propanoic acid;2-Amino-3-(2-aminopyridin-4-yl)propanoic acid;2-Amino-3-(6-aminopyridin-2-yl)propanoic acid;2-Amino-3-(5-aminopyridin-3-yl)propanoic acid;2-Amino-3-(5-sulfanylpyridin-3-yl)propanoic acid;2-Amino-3-(2-sulfanylpyridin-4-yl)propanoic acid;2- Amino-3-(pyrimidin-5-yl)propanoic acid;2-Amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid;2-Amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride;2-Amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid;2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid;2-Amino-3-(pyrazin-2-yl)propanoic acid;2-Amino-3-(5-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2 ,5-Dichloropyridin-3-yl)propanoic acid;2-Amino-3-(pyrimidin-4-yl)propanoic acid;2-Amino-3-(5-fluoropyridin-3-yl)propanoic acid;2-Amino-3-(6-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-difluoropyridin-4-yl)propanoic acid;2-Amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid Panic acid;2-amino-3-(2-bromopyridin-4-yl)propanoic acid;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid;2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid;2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid;2-amino-3-(5-(trifluoromethyl)pyridin-3-yl)propanoic acid;2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid;2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid;2-Amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid;2-Amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid 2-Amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate;2-Amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate;2-Amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid;Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid 2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoate;Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate;Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate;2-Amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid;2-Amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid;Methyl 2-amino-3-(2-bromopyridin-4-yl) Propanoate;3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium;3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium;2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid;Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate;Ethyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Ethyl-2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate;2-(2-methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;2-(2-ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium;2-Amino-3-[2-(trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride [HCl] ;Ethyl 3-[(2-bromopyridin-4-yl)oxy]-2-acetamidopropanoate;Ethyl 2-acetamido-3-(pyridin-4-yloxy)propanoate;2-Amino-4-(1H-pyrrol-3-yl)butanoic acid;2-Amino-3-(1H-pyrrol-2-yl)propanoic acid;2-Amino-3-(1H-pyrrol-3-yl)propanoic acid;2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid;(2S)-2-Hydroxy-3-(1H-imidazoline) 2-Amino-3-(1-methyl-1H-1,2,4-triazol-5-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride;2-Amino-3-(2- and b) a compound selected from the group consisting of methyl-2H-1,2,3,4-tetrazol-5-yl)propanoic acid hydrochloride; 2-amino-3-(dimethyl-4H-1,2,4-triazol-3-yl)propanoic acid hydrochloride; (2S)-2-amino-3-[5-(trifluoromethyl)-1H-pyrazol-4-yl]propanoic acid; and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate; and a second herbicide.

[0099] According to some embodiments, the present invention provides a) 2-amino-3-(thiophen-2-yl)propanoic acid; 2-amino-3-(thiophen-3-yl)propanoic acid; 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine ;2-Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid;3-Amino-3-(4-bromothiophen-3-yl)propanoic acid;2-Amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid;Butyl 2-amino-3-(thiophen-3-yl)propanoate;2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(2-chlorothio 2-Amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid;2-Amino-3-(5-chlorothiophen-3-yl)propanoic acid;2-Amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,3-thiazol-5-yl)propanoic acid;2-Amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid;2-Amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid;Methyl 2 -Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate;[2-(Carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid;2-Amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid;2-Amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid;2-Amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid;2-Amino-3-(furan-3-yl)propanoic acid;2-Amino-3-(1,3-oxazol-4-yl)propanoic acid;2-Formamido-3-(thiophen-3-yl)propanoic acid;Methyl 2-amino-3-(thiophen-3-yl)propanoate;Ethyl 2-amino-3-(thiophen-3-yl)propanoate 2-Amino-3-(thiophen-3-yl)propanamido]acetic acid;2-Amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide;Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate;2-Butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;2-Amino-3-(2,5-dibromothiophen-3-yl)propanoic acid;2-Amino-3-(5-nitrothiophen-3-yl)propanoate 2-Amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid;(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid;2-Amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid;2-Amino-3-(5-chloro-2- 2-Amino-3-(2-bromothiophen-3-yl)propanoic acid;2-Amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid;2-Amino-3-(thiolan-3-yl)propanoic acid;[2-Amino-2-(thiophen-3-yl)ethyl]phosphonic acid;2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid;3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid;2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid;Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate;Methyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate;2-(2-Methoxyethoxy)ethyl-2-acetamido 2-Amino-3-(thiophen-3-yl)propanoate;Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate;Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate;Propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate;4-(2-acetamido 2-(2-Ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate;Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate;Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)thiophene]-3-sulfonyl 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate;2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl];2-Amino-3-(pyridazin-4-yl)propanoic acid;2-Amino-3-(pyridin-4-yl)propanoic acid;2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-Hydroxy-3-pyridinyl)alanine;2-Amino-3-(5-methylpyridin-3-yl)propanoic acid;2-Amino-3-(4-aminopyridin-2-yl)propanoic acid;2-Amino-3-(2-aminopyridin-4-yl)propanoic acid;2-Amino-3-(6-aminopyridin-2-yl)propanoic acid;2-Amino-3-(5-aminopyridin-3-yl)propanoic acid;2-Amino-3-(5-sulfanylpyridin-3-yl)propanoic acid;2-Amino-3-(2-sulfanylpyridin-4-yl)propanoic acid;2- Amino-3-(pyrimidin-5-yl)propanoic acid;2-Amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid;2-Amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride;2-Amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid;2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid;2-Amino-3-(pyrazin-2-yl)propanoic acid;2-Amino-3-(5-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2 ,5-Dichloropyridin-3-yl)propanoic acid;2-Amino-3-(pyrimidin-4-yl)propanoic acid;2-Amino-3-(5-fluoropyridin-3-yl)propanoic acid;2-Amino-3-(6-chloropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-dichloropyridin-4-yl)propanoic acid;2-Amino-3-(3,5-difluoropyridin-4-yl)propanoic acid;2-Amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid Panic acid;2-amino-3-(2-bromopyridin-4-yl)propanoic acid;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid;2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid;2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid;2-amino-3-(5-(trifluoromethyl)pyridin-3-yl)propanoic acid;2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid;2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid;2-Amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid;2-Amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyrimidin-3-yl)propanoic acid;2-Amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid;2-Amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid 2-Amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate;2-Amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid;Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate;2-Amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid;Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid 2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoate;Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate;Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate;2-Amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid;2-Amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid;2-Amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid;Methyl 2-amino-3-(2-bromopyridin-4-yl) Propanoate;3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium;3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium;2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid;Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate;Ethyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate;Ethyl-2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate;2-(2-methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;2-(2-ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate;5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium;2-Amino-3-[2-(trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride [HCl] ;Ethyl 3-[(2-bromopyridin-4-yl)oxy]-2-acetamidopropanoate;Ethyl 2-acetamido-3-(pyridin-4-yloxy)propanoate;2-Amino-4-(1H-pyrrol-3-yl)butanoic acid;2-Amino-3-(1H-pyrrol-2-yl)propanoic acid;2-Amino-3-(1H-pyrrol-3-yl)propanoic acid;2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid;(2S)-2-Hydroxy-3-(1H-imidazoline) 2-Amino-3-(1-methyl-1H-1,2,4-triazol-5-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid dihydrochloride;2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride;2-Amino-3-(2- The present invention provides a mixture comprising a compound selected from the group consisting of methyl-2H-1,2,3,4-tetrazol-5-yl)propanoic acid hydrochloride; 2-amino-3-(dimethyl-4H-1,2,4-triazol-3-yl)propanoic acid hydrochloride; (2S)-2-amino-3-[5-(trifluoromethyl)-1H-pyrazol-4-yl]propanoic acid; and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate; and b) a plant growth regulator. [Example]

[0100] In the following examples, if an abbreviation is not defined above, it has its generally accepted meaning. Furthermore, all temperatures are in degrees Celsius (unless otherwise stated). The following methods were used to prepare the compounds listed as indicated below.

[0101] Example 1: Synthesis of ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate (code 567)

[0102] [ka] Step A: To a stirred mixture of NaH (44 g, 1.1 mol, 60% in silicone oil) and diethyl acetamidomalonate 1 (217 g, 1.0 mol) in dry DMF (2.50 L) was added 2,3-dibromopropene (240 g, 1.2 mol). The reaction mixture was stirred overnight at room temperature to give diethyl 2-acetamido-2-(2-bromoallyl)malonate. After completion of the reaction (confirmed by H NMR), the reaction mixture was used in Step B.

[0103] Step B: To a solution of diethyl 2-acetamido-2-(2-bromoallyl)malonate (336 g) obtained in Step A, water (45 mL, 2.5 mol) and LiBr (102 g, 1.2 mol) were added in that order, and the mixture was heated to reflux under argon for 6 h. The mixture was then evaporated to remove DMF and quenched with EtOAc (1.5 L) and HO (1 L). The mixture was stirred for 10 min, extracted with EtOAc (3 x 0.5 L), and the combined organic layers were washed with brine (3 x 0.5 L), dried over anhydrous NaSO, and concentrated under reduced pressure. The resulting oily residue (210 g, 93% purity) was used in the next step without further purification.

[0104] Step C: To a cold (0 °C) stirred solution of 3 (210 g, 93% purity, 0.74 mol) in a 2:1 mixture of acetonitrile / water (1.68 L) under nitrogen, solid N-bromosuccinimide (193 g, 1.08 mol) was added in three portions over a 15 min period. The resulting orange-red mixture was stirred at 0 °C for 1 h. The reaction mixture was treated with 10% aqueous sodium thiosulfate in ethyl acetate (1.5 L) at room temperature and washed with water (4 x 300 mL) and brine (4 x 300 mL). Evaporation of the organic solvent gave compound 4 (122 g, 0.43 mol), which was used in the next step without purification.

[0105] Step D: Compound 4 (122 g, 0.43 mol) and thiourea (33 g, 0.44 mol) were dissolved in EtOH (1.5 L) and stirred under reflux overnight. After the reaction was complete (confirmed by H NMR), the organic solvent was evaporated and the crude residue was partitioned with EtOAc / HO (1 L:1 L). The lower layer was carefully basified with 10% aqueous NaOH to pH = 9 and extracted with CHCl (3 x 150 mL). The combined organic layer was washed with brine (2 x 100 mL), dried over anhydrous NaSO, and evaporated to give compound 5 (80 g, 0.28 mol).

[0106] Step E: Compound 5 (80 g, 0.28 mol) and N-chlorosuccinimide (56 g, 0.42 mol) were dissolved in acetonitrile (1.5 L). The mixture was stirred at ambient temperature for 1 hour. After completion of the reaction, acetonitrile was evaporated under reduced pressure, and the residue was partitioned with water / ethyl acetate (400 mL:400 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 x 150 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give compound 6 (60 g, crude, 70% purity), which was used immediately in the next step without purification.

[0107] Step F: A round-bottom flask was charged with crude compound 6 (60 g, crude, 70% purity), copper(II) chloride (38 g, 0.28 mol), and tert-butyl nitrite (35.6 mL, 0.3 mol) in CHCN (1 L). The mixture was heated to 40 °C for 2 h, then the mixture was diluted with 1 N HCl and extracted with EtOAc. The organic extract was washed with water (2 x 100 mL), brine (2 x 100 mL), dried over anhydrous NaSO, filtered, and concentrated under reduced pressure to give the title compound, which was purified by CC to 95% purity (5.5 g, 0.018 mol).

[0108] Analysis data: 1 H NMR (400MHz, CDCl3) δ6.42(s, 1H), 4.99-4.75(m, 1H), 4.17(q, J=6.7Hz, 2H), 3.30-2.99(m, 2H), 2.00(s, 1H), 1.24(t, J=7.1Hz, 3H); EδI: Calculated value [M + ](C 10 H 12 O3SN2Cl2) m / z: 311 and 313. Measured value [Me - ] + , 311 and 312.9 [M+Cl - ] - =346.8 and 348.7.

[0109] Example 2: Synthesis of ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate (code 569)

[0110] [ka]

[0111] Step 1: To a flame-dried flask containing At-BuOK (12.3 g, 109 mmol, 1.10 equiv.) and anhydrous DMF (900 mL) under argon at 0 °C, ethyl 2-((diphenylmethylene)amino)acetate 2 (27.9 g, 104 mmol, 1.05 equiv.) was added. After 10 min, chloride 1 (20 g, 99 mmol, 1.0 equiv.) was added. The resulting reaction mixture was stirred at 0 °C for 10 min and then at room temperature overnight. The reaction mixture was then slowly poured into water and extracted with DCM. The combined organic layers were dried over anhydrous NaSO, filtered, and concentrated under reduced pressure to give compound 3 (29.0 g, 67.6%).

[0112] Step B. Compound 3 (29.0 g, 67 mmol) was treated with a mixture (700 mL) of EtOH / concentrated HCl (25:1 volume ratio). The resulting solution was stirred at room temperature for 2 hours. After evaporation of the solvent, the residue was rinsed with water, washed with hexane, and concentrated under reduced pressure to give the target product (16.9 g, 83.0%).

[0113] Analysis data: 1 H NMR(DMSO-d6)δ H (ppm):1.12(t, 3H, CH3), 3.02-3.14(dd, 2H, CH2), 4.07-4.16(m, 2H, CH2), 4.20- 4.26 (m, 1H, CH), 7.20 (s, 1H, HetAr.H), 8.67-8.78 (brs, 3H, NH2 HCl) EδI: Calculated value [M + ](C9H 11 O2NSCl2) m / z: 268.0 and 270.0. Measured value [Me - ] + , 268.0 and 270.0.

[0114] Example 3: Synthesis of 2-amino-3-(2,5-dibromothiophen-3-yl)propanoic acid (code 552)

[0115] [ka]

[0116] A. Sodium borohydride (2.0 g, 53 mmol, 0.5 equiv) was added to a solution of aldehyde 1 (12.0 g, 107 mmol, 1 equiv) in methanol (150 mL) at 0 °C. The reaction mixture was stirred at room temperature for 4 h and then partitioned with 5% HCl (300 mL) and ethyl acetate (150 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 150 mL). The combined organic phases were dried over NaSO, filtered, and concentrated to dryness to give product 2 (10.1 g, 83%).

[0117] B. NBS (30.7 g, 173 mmol, 1.95 equiv.) was slowly added to compound 2 (10.1 g, 88 mmol, 1 equiv.) in THF (300 mL). The mixture was kept at room temperature overnight, filtered, and the THF was removed by rotary evaporation. The product was dissolved in diethyl ether and then rinsed with 1 M sodium hydroxide solution and water. The organic layer was dried over Na2SO4, and the product was eluted on silica gel with hexane:ethyl acetate (80:20). The solvent was removed by rotary evaporation to give the desired product 3 (18.5 g, 77% yield).

[0118] C. Compound 3 (17.3 g, 64 mmol, 1 equiv.) in DCM (200 mL) was added to a 500 mL flask and the flask was placed in an ice-water bath. Phosphorus tribromide (6.6 mL, 70 mmol, 1.1 equiv.) was added dropwise to the solution. The reaction was carried out at room temperature for 5 hours and then quenched with 10% sodium bicarbonate solution. The organic solution was washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give compound 4 (18.5 g, 87% yield).

[0119] To a flame-dried flask containing Dt-BuOK (6.8 g, 61 mmol, 1.10 equiv.) and anhydrous DMF (500 mL) under argon at 0 °C, ethyl 2-((diphenylmethylene)amino)acetate 2 (15.5 g, 58 mmol, 1.05 equiv.) was added. After 10 min, bromide 4 (18.5 g, 55 mmol, 1.0 equiv.) was added. The resulting reaction mixture was stirred at 0 °C for 10 min, warmed to room temperature, stirred overnight, and then slowly poured into water and extracted with DCM. The combined organic layers were dried over anhydrous NaSO, filtered, and concentrated under reduced pressure to give compound 5 (21.3 g, 74%).

[0120] E. Compound 5 (21.3 g, 41 mmol) was treated with a mixture of EtOH / concentrated HCl (25:1 volume ratio) (400 mL). The resulting solution was stirred at room temperature for 2 hours. The solvent was evaporated, and the residue was basified to pH > 10 with 2N K2CO3 solution. The combined organic layers extracted with DCM were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:20 CH3OH / DCM) to yield product 6 (11.0 g, 75%).

[0121] F. Product 6 (11.0 g, 31 mmol) was dissolved in 3N hydrochloric acid (250 mL). The mixture was stirred at 70° C. for 12 hours. The solvent was removed under reduced pressure to give the title compound (11.25 g, 99%).

[0122] Analysis data: 1 H NMR(DMSO-d6)δ H (ppm):3.08(m, 2H, CH2), 4.05(t, 1H, CH), 7.24(s, 1H, HetAr.H);8.2-9.1(br.s, 2H, NH2);EδI: Calculated value [M + ](C7H7O2NSBr2) m / z: 328.86. Measured value [M+H + ]=329.8 and 327.8, [MH + ], 327.80 and 325.8.0.

[0123] Example 4: Synthesis of 5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium (code 676)

[0124] [ka]

[0125] A. Compound 1 and methyl 2-{[(tert-butoxy)carbonyl]amino}-2-(dimethylphosphonoacetate) (1.2 equivalents) were dissolved in DCM. The reaction mixture was then cooled, and 2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine (1.4 equivalents) was slowly added. The reaction mixture was stirred overnight at room temperature. It was then washed with water (three times) and brine, dried over anhydrous NaSO, and evaporated to yield crude compound 2.

[0126] B. Compound 2 in MeOH was added to Pd / C 5% (0.1 equivalent). The reaction mixture was stirred overnight at room temperature under H atmosphere, filtered, and the resulting solution was evaporated to give crude compound 3. Crude compound 3 was purified by column chromatography (Hex-EtOAc as the eluent mixture).

[0127] C. Compound 3 was dissolved in MeCN and MeI (7 equiv.) was added dropwise. The reaction was stirred at room temperature overnight. It was then evaporated to give crude compound 4, which was used in the next step without further purification.

[0128] D. Compound 4 was dissolved in HCl / dioxane and the reaction was refluxed overnight, after which it was evaporated to give crude compound 5, which was stirred with MeCN, filtered, and dried to give the target compound.

[0129] Analysis data: 1 H NMR (DMSO-d), δ H(ppm): 3.40-3.60(d, 2H, CH2), 4.50-4.60(br.s, 1H, CH), 8.80-8.95(br.s, 3H, CH3), 9.40(s, 1H, PyrH), 9.65(s, 1H, PyrH), 9.70(s, 1H, PyrH). 13 C NMR(DMSO-d6)δ H (ppm): 30.12 (CH2), 45.5 (CH3), 52.3 (CH), 132.2 (PyrCq), 153.0 (PyrCH), 154.3 (PyrCH), 165.0 (PyrCH), 169.8 (COOH). EδI: Calculated value [M + ](C8H 12 O2N3) m / z: 182.0. Measured value [Me - ] + , 182.0.

[0130] Example 5: Synthesis of methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate (Code 670)

[0131] [ka]

[0132] A. Compound 1 (16.0 g, 60 mmol, 1 equiv.) in DCM (200 mL) was added to a 500 mL flask and the flask was placed in an ice-water bath. Phosphorus tribromide (6.8 mL, 72 mmol, 1.2 equiv.) was added dropwise to the solution. The reaction was carried out at room temperature for 5 hours and then quenched with 10% sodium bicarbonate solution. The organic solution was washed with water, dried over Na2SO4, and concentrated under reduced pressure to give compound 2 (18.5 g, 94.0% yield).

[0133] To a flame-dried flask containing Bt-BuOK (6.9 g, 62 mmol, 1.10 equiv) and anhydrous DMF (500 mL) under argon at 0 °C, methyl 2-((diphenylmethylene)amino)acetate (14.9 g, 59 mmol, 1.05 equiv) was added. After 10 min, bromide 2 (18.5 g, 55 mmol, 1.0 equiv) was added. The resulting reaction mixture was stirred at 0 °C for 10 min, warmed to room temperature, and stirred overnight. The reaction mixture was then slowly poured into water and extracted with DCM. The combined organic layers were dried over anhydrous NaSO, filtered, and the compound was concentrated under reduced pressure to give 3 (24.5 g, 87.0%).

[0134] C. Compound 3 (24.5 g, 49 mmol) was treated with a mixture of EtOH / 48% HBr (25:1 volume ratio) (600 mL). The resulting solution was stirred at room temperature for 2 hours. After evaporation of the solvent, the residue was rinsed with water, washed with hexane, and concentrated under reduced pressure to yield the target product 4 (19.7 g, 81.0%).

[0135] Analysis data: 1 H NMR (DMSO-d), δ H (ppm):3.00-3.10(m, 1H, CH2), 3.15-3.23(m, 1H, CH2), 3.75(s, 3H, CH3), 4.50-4.58(t, 1H, CH), 7.70(s, 2H, PyrH), 8.30-8.40(br.s, 3H, NH2 H + );EδI: Calculated value [M + ](C9H 10 O2N2Br2) m / z: 338.0 (Br79 and 81). Measured value [Me - ] + , 339.0 and 341.0.

[0136] Example 6: Synthesis of ethyl 2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoate (Code 580)

[0137] [ka]

[0138] Step AN-Boc-3-amino-alanine 1 (50 g, 0.23 mol, 2.3 equiv.) was suspended in 2 L of anhydrous acetone in a flame-dried 4 L flask under argon. TEA (70 mL, 0.5 mol, 5.1 equiv.) was then added, and the reaction mixture was stirred at room temperature for 30 min. Compound 2 was dissolved in anhydrous acetone and added dropwise to the reaction mixture at -5 to +5 °C. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured onto ice, acidified with aqueous citric acid, and extracted with ethyl acetate (5 x 500 mL). The combined organic layers were washed with water (2 x 200 mL), dried over anhydrous NaSO, and evaporated under reduced pressure. The resulting crude compound 3 was purified by column chromatography. The mass of product 3 (90% purity) was isolated (9 g, 18% yield).

[0139] Step B. In a flame-dried 1 L three-neck flask, DCC (2.6 g, 0.0124 mol, 1.1 equiv.) and DMAP (0.014 g, 0.00114 mol, 0.01 equiv.) were treated with a solution of sulfamide 3 (5.8 g, 0.0114 mol, 1 equiv.) in 500 mL of anhydrous methylene chloride. Then, anhydrous ethanol (approximately 2 mL, 0.022 mol, approximately 2 equiv.) was added to the reaction mixture. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then evaporated under reduced pressure. Water was added to the residue, and the target compound was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and evaporated. The crude compound was purified by column chromatography (yield: 2.5 g of 90% pure target compound, 40% yield).

[0140] Step C. HCl / dioxane (100 mL) was added to sulfamide 4 (2.5 g, 0.0046 mol, 1 equiv.) dissolved in 20 mL of dry chloroform in a flame-dried 250 mL flask. The reaction mixture was stirred overnight. The solvent was evaporated. The target compound was purified by HPLC. Yield 0.7959 g (approximately 36%).

[0141] Analytical Data: Solid 1H NMR δH(ppm): 1.28-1.37(t, 3H, CH3), 3.35-3.45(m, 1H, CH2), 3.51-3.55(m, 1H, CH2), 4.04-407(br.s, 1H, CH), 4.20-4.30(m, 2H, CH2), 7.30(s, 1H, thiophene H); EδI: Calculated value [M] + (C9H 12 O4N2S2Br2) m / z = 404 (Br79 / 81) and 406 (Br=81). Found values [M+H + ]=406.8 (Br=79 / 81) and 468.8 (Br81 / 81).

[0142] Example 7: Synthesis of ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate (code 573)

[0143] [ka]

[0144] To a flame-dried flask containing At-BuOK (9.2 g, 82 mmol, 1.10 equiv.) and anhydrous DMF (700 mL) under argon at 0 °C, ethyl 2-((diphenylmethylene)amino)acetate 2 (20.9 g, 78 mmol, 1.05 equiv.) was added. After 10 min, chloride 1 (15 g, 74 mmol, 1.0 equiv.) was added. The resulting reaction mixture was stirred at 0 °C for 10 min, and then the mixture was stirred at room temperature overnight. The reaction mixture was then slowly poured into water and extracted with DCM. The combined organic layers were dried over anhydrous NaSO, filtered, and concentrated under reduced pressure to give compound 3 (21 g, 65.2%).

[0145] B. Compound 3 (21.0 g, 49 mmol) was treated with a mixture (500 mL) of EtOH / concentrated HCl (25:1 volume ratio). The resulting solution was stirred at room temperature for 2 hours. After evaporation of the solvent, the residue was basified to pH > 10 with 2N K2CO3 solution and extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:20 CH3OH / DCM) to give compound 4 (12.7 g, 86%).

[0146] C. To a stirred solution of compound 4 (12.7 g, 47 mmol, 1.0 equiv.) in 300 mL of DCM was added 13.2 mL of TEA (95 mmol, 2 equiv.), followed by 4.9 mL of acetic anhydride (52 mmol, 1.1 equiv.). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then diluted with 150 mL of NaHCO3 and extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:4 EtOAc / hexanes) to give compound 5 (13.3 g, 91%).

[0147] Analysis data: 1 H NMR (400 MHz, CDCl) δ H (ppm): 1.2-1.3 (t, 3H, CH), 1.95 (s, 3H, CH), 2.95-3.10 (dd, 2H, CH-thiophene), 4.10-4.25 (m, 2H, CH-ethyl), 4.75-4.80 (d, 1H, CH), 6.00 (s, 1H, H-thiophene), 6.60 (s, 1H, NH); EδI: calculated [M + ](C 11 H 13 O3NSCl2) m / z: 310.0 and 312.0. Measured value [Me - ] + , 310.0 and 312.0.

[0148] Example 8: Synthesis of 2-ethoxyethyl 3-(dichloro-1,3-thiazol-4-yl)-2-acetamidopropanoate (code 555)

[0149] [ka]

[0150] To a stirred mixture of NaH (44 g, 1.1 mol, 60% in silicone oil) in dry DMF (2.50 L) was added diethyl acetamidomalonate 1 (217 g, 1.0 mol) and 2,3-dibromopropene (240 g, 1.2 mol). The reaction mixture was stirred overnight at room temperature. After completion of the reaction (controlled by H NMR), the mixture was used in the next step without quenching.

[0151] B. To a solution of diethyl 2-acetamido-2-(2-bromoallyl)malonate 2 (336 g) in DMF (2.5 L) was subsequently added HO (45 mL, 2.5 mol) and LiBr (102 g, 1.2 mol), and the mixture was heated to reflux under argon for 6 h. The mixture was then evaporated to remove DMF and quenched with EtOAc (1.5 L) and HO (1 L). The mixture was stirred for 10 min, extracted with EtOAc (3 x 0.5 L), and the combined organic layers were washed with brine (3 x 0.5 L), dried over NaSO, and concentrated under reduced pressure. The resulting oily residue 3 (210 g, 93% purity) was used in the next step without purification.

[0152] C. Under nitrogen, to a cold (0 °C) stirred solution of 3 (210 g, 93% purity, 0.74 mol) in a 2:1 mixture of acetonitrile / water (1.68 L), solid N-bromosuccinimide (193 g, 1.08 mol) was added in three portions over a 15-minute period. The resulting orange-red mixture was stirred at 0 °C for an additional 1 h and then warmed to room temperature. After 4 h, the reaction mixture was treated with 10% aqueous sodium thiosulfate, diluted with ethyl acetate (1.5 L), and washed with water (4 x 300 mL) and brine (4 x 300 mL). The organic solvent was evaporated to give compound 4 (122 g, 0.43 mol), which was used in the next step without purification.

[0153] D. Compound 4 (122 g, 0.43 mol) and thiourea (33 g, 0.44 mol) were dissolved in EtOH (1.5 L) and stirred under reflux overnight. After the reaction was complete (confirmed by H NMR), the organic solvent was evaporated and the crude residue was partitioned with EtOAc / HO (1 L:1 L). The lower layer was carefully basified with 10% aqueous NaOH to pH = 9 and extracted with CHCl (3 x 150 mL). The combined organic layers were washed with brine (2 x 100 mL), dried over NaSO, and evaporated to give product 5 (80 g, 0.28 mol).

[0154] A solution of E.5 (80 g, 0.28 mol) and N-chlorosuccinimide (56 g, 0.42 mol) in acetonitrile (1.5 L) was stirred at room temperature for 1 hour. After completion of the reaction, acetonitrile was evaporated under reduced pressure, and the residue was partitioned between water (400 mL) and ethyl acetate (400 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 x 150 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give product 6 (60 g, crude, 70% purity), which was used immediately in the next step without purification.

[0155] F. A round-bottom flask was charged with crude compound 6 (60 g, crude, 70% purity), copper(II) chloride (38 g, 0.28 mol), and tert-butyl nitrite (35.6 mL, 0.3 mol) in CHCN (1 L). The mixture was heated to 40 °C for 2 h, then diluted with 1 N HCl and extracted with EtOAc. The organic extract was washed with water (2 x 100 mL), brine (2 x 100 mL), dried over NaSO, filtered, and concentrated under reduced pressure to give compound 7, ethyl 2-acetamido-3-(2,5-dichlorothiazol-4-yl)propanoate. The product was purified by CC (5.5 g, 0.018 mol).

[0156] To a solution of G.7 (5.5 g, 0.018 mol) in CHOH (30 mL) was added KOH (1.1 g, 0.0198 mol) in water (5 mL) in small portions, and the resulting mixture was stirred overnight. After the reaction was complete (confirmed by H NMR), the organic solvent was evaporated, and the crude residue was partitioned with MTBE / HO (30 mL:50 mL). The organic layer was discarded. The aqueous layer was acidified with 10% aqueous NaHSO to pH = 3 and extracted with DCM (3 x 50 mL). The combined organic layers were dried over NaSO and evaporated under reduced pressure to give compound 8 (3.2 g, 0.011 mol), which was used in the next step without purification.

[0157] H. 2-Acetamido-3-(2,5-dichlorothiazol-4-yl)propanoic acid 8 (3.2 g, 0.011 mol) was dissolved in DCM (30 mL), followed by the addition of CDI (1.9 g, 0.012 mol) in small portions. After gas evolution ceased, 2-ethoxyethan-1-ol (5.3 mL, 0.055 mol) was added, and the mixture was stirred overnight. After the reaction was complete, the mixture was diluted with DCM (50 mL) and washed with 1 N HCl (3 x 15 mL), saturated aqueous NaHCO (3 x 20 mL), and brine (2 x 10 mL), dried over NaSO, and evaporated under reduced pressure. The crude product was purified by CHCl3 to give the target compound as a beige solid (1.5 g, 4.2 mmol).

[0158] Analysis data: 1 H NMR (CDCl), δ H (ppm):1.20(t, 3H, CH3), 2.01(s, 3H, CH3), 3.22(d, 2H, CH2), 3.50(d, 2H, CH2), 3.6 3(t, 2H, CH2), 4.28(t, 2H, CH2), 4.95(d, 1H, CH), 6.40(br.s, 1H, NH); EδI: Calculated value [M](C 12 H 16 , O4, N2SCl2), m / z = 354 (Cl = 35.0), 356 (1Cl = 35.0 and 2Cl = 35.6). Measured value [M+H + ]=355.1.

[0159] Example 9: Testing the post-emergence herbicidal activity of selected non-encoded heterocyclic amino acids (NCHAAs) Tests were conducted on romaine lettuce (Lactuca sativa L.) plants at the 2- to 3-leaf stage. Plants were grown in 300-well trays with well dimensions of 2 x 2 x 5 cm filled with soil. Test dilutions containing the test materials are listed in Tables 1, 2, and 3. Each compound was dissolved in a 0.1% aqueous solution of Silwet, an agriculturally acceptable surfactant, to give final concentrations ranging from 0.0% (control) to 0.5%. Two weeks after treatment, the herbicidal efficacy of each test material was evaluated visually in comparison with control plants. Additionally, the above-ground parts of the plants were cleaned and weighed (wet weight). Each test was performed on 20 to 40 plants. Test compounds are listed in Table 1.

[0160] Table 1: Chemical names and code names of test compounds

[0161] [Table 1] TIFF2025122033000064.tif203170TIFF2025122033000065.tif193170TIFF202 5122033000066.tif208170TIFF2025122033000067.tif204170TIFF20251220330 00068.tif209168TIFF2025122033000069.tif209168TIFF2025122033000070.t if209168TIFF2025122033000071.tif207170TIFF2025122033000072.tif191170

[0162] The degree of growth inhibition and injury was assessed according to the parameters in Table 2. Plant development at 7, 14, and 21 DAA (days after application) was assessed on a scale of 0 to 100, with a score of 0 representing dead plants and a score of 100 representing healthy plants according to plant vigor, height, and leaf color. Each test included 20 to 40 plants.

[0163] Table 2: Activity index

[0164] [Table 2]

[0165] result: The observed activities are shown in Table 3.

[0166] Table 3: Post-emergence herbicidal activity of test compounds

[0167] [Table 3] TIFF2025122033000075.tif209160TIFF2025122033000076.tif99170

[0168] Example 10: Testing the herbicidal activity of selected non-encoded heterocyclic amino acids (NCHAAs) against weed and crop development The experiment included 225 pots. Weed seeds were sown in 0.3 L pots containing medium-weight clay loam soil from the Newe Ya'ar Research Center's organic field (55% clay, 23% silt, 20% sand, 2% organic matter, pH 7.1). The experiment was conducted using a completely randomized design. Each treatment was replicated five times (five pots). Herbicides were applied at 200 L / ha using an electric sprayer (Spraying Systems Co., North Ave., Wheaton, IL 60188, USA) fitted with a Tee Jet 8001E nozzle, operated at a pressure of 300 kPa. Twenty-four hours after herbicide application, the pots were transferred to a greenhouse and irrigated with sprinklers to bring the soil to field capacity. Plants were grown in the greenhouse throughout the experiment. Plant development at 6, 12, 19, 26, and 32 days after application (DAA) was assessed on a scale of 0–100%, with 0 representing plant death and 100% representing a healthy plant according to plant vigor, height, and leaf color.

[0169] Weeds and crops examined: Phalaris minor (reed canary grass); Setaria verticillata (green foxtail); Solanum nigrum (nightshade); Sinapis arvensis (mustard); Silybum marianum (milk thistle); Chenopodium album (lamb's weed); Amaranthus; Fodder corn; Avena sativa (cultured oat).

[0170] Plant development at 32 days after application (DAA) is shown in Table 4. Plant development was rated on a 0-100% scale, with 0 representing plant death and 100% representing a healthy plant according to plant vigor, height, and leaf color.

[0171] Table 4: Effect of NCHAA on selected weed and crop development

[0172] [Table 4]

[0173] Example 11: Herbicidal activity testing of selected non-encoded heterocyclic amino acids (NCHAAs) on seed germination and early plant development

[0174] seed: Lettuce R. (Super Jericho, non-sterile) seeds were obtained with 99% purity from Ben Shahar Moshe Ltd. NCHAAs were selected from the compounds listed in Table 1.

[0175] Lettuce seed filter paper bioassay: The protocol was based on Bertin et al., 2009 and Movellan et al., 2014, with specific modifications as described below.

[0176] Seeds were placed on Whatman No. 1 filter paper (Whatman, Middlesex, UK) in Petri dishes supplemented with 2.0 mL of water (control) or solutions containing 1 mM, 0.1 mM, 0.01 mM, and 0.001 mM test material (10 seeds / plate). The Petri dishes containing the seeds were placed in trays at a 45° angle. The trays were kept in the dark for 48 hours and then transferred to a growth chamber (22°C, 0.045 mmol × m-2 × s-1 photosynthetic photon flux density; 6 / 18 dark / light cycle) for an additional 4 days. Each experiment was performed at least twice. Radicle and shoot development of experimental and control plants was visually evaluated 6 days after the start of the experiment to determine the minimum effective concentration (MEC) of the test material. In the context of this invention, the MEC is defined as the lowest concentration level of the test material that caused a deviation from the development of the control plants (lack of germination or malformed radicle and shoot). The MEC is expressed as an activity score in arbitrary units, as shown in Table 5.

[0177] Table 5: MEC as activity score

[0178] [Table 5]

[0179] Table 6: Herbicidal activity of selected non-encoded heterocyclic amino acids (NCHAAs) on seed germination and early plant growth

[0180] [Table 6] TIFF2025122033000080.tif254154

[0181] Consideration: The design of non-encoded heterocyclic amino acids (NCHAAs) was intended to mimic natural aromatic amino acids such as phenylalanine, tyrosine, histidine, and tryptophan. These compounds were tested in a variety of experimental settings, including experiments involving seeds placed on filter paper and pre- or post-emergence treatment of weeds and crops. Experimental data suggest that, despite their diverse chemical structures, NCHAAs as a group possess significant herbicidal activity. Surprisingly, selected NCHAAs exhibited herbicidal activity significantly superior to natural (e.g., m-tyrosine) and synthetic non-encoded amino acids with "non-heterocyclic, all-carbon" aromatic rings, such as the m-tyrosine compound described by Leslie A. Weston et al., U.S. Patent No. 8,461,085 (Cornell Business & Technology Park). NCHAAs have emerged as a new class of compounds useful in crop protection, particularly those used to destroy unwanted vegetation.

[0182] Unless otherwise defined, all technical and / or scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of this invention, exemplary methods and / or materials are described below. In case of conflict, the patent specification, including definitions, will control. Furthermore, the materials, methods, and examples are illustrative only and are not intended to be necessarily limiting.

[0183] As used herein, the words "comprises," "comprising," "includes," "including," "having," and combinations thereof, mean "including but not limited to."

[0184] The term "consisting of" means "including and limited to."

[0185] As used herein, the singular forms "a," "an," and "the" include the plural forms unless the context clearly dictates otherwise. For example, the term "a compound" or "at least one compound" may include a plurality of compounds, including mixtures.

[0186] When an element is referred to as "touching," "connected to," "coupled to," "bonded to," "contacting," etc., with respect to another element, it can be directly touching, connected to, coupled to, bonded to, and / or in contact with the other element, or intervening elements can be present. In contrast, when an element is referred to as, for example, "directly touching," "directly connected to," "directly coupled," "directly bonded to," or "in direct contact with" another element, there are no intervening elements. It will also be understood by those skilled in the art that a reference to a structure or feature located "adjacent to" another feature can have portions that overlap or underlie the adjacent feature.

[0187] In this specification, terms such as first and second may be used to describe various elements, components, regions, layers, and / or sections, but these elements, components, regions, layers, and / or sections should not be limited by these terms. Rather, these terms are used only to distinguish one element, component, region, layer, and / or section from another element, component, region, layer, and / or section.

[0188] As will be understood by those skilled in the art, compounds of the various formulas disclosed herein may contain chiral centers, e.g., asymmetric carbon atoms. Accordingly, the present disclosure pertains to the synthesis of both (i) racemic mixtures of active compounds and (ii) enantiomeric forms of active compounds. Resolution of racemates into enantiomeric forms and racemization of optically active enantiomeric forms can be performed according to procedures known in the art. Geometric isomers, such as double bonds, may also exist in the compounds disclosed herein, and all such stable isomers are included in the present disclosure unless otherwise specified. The compounds of the present disclosure also include tautomers (e.g., tautomers of triazoles and / or imidazoles) and rotational isomers. All chains defined by the formulas herein containing three or more carbons can be saturated or unsaturated unless otherwise specified.

[0189] It is understood that the substituents and substitution patterns on the compounds used in the methods of the present invention can be selected by one of ordinary skill in the art to provide compounds that are chemically stable and that can be easily synthesized from readily available starting materials by techniques known in the art. It is understood that when a substituent is itself substituted with multiple groups, these multiple groups can be on the same carbon or on different carbons, so long as a stable structure results.

[0190] An "optionally substituted" group refers to a functional group in which one or more bonds to a hydrogen atom are replaced with a bond to a non-hydrogen or non-carbon atom, provided that the normal valence is maintained and the substitution results in a stable compound. Substituted groups also include groups in which one or more bonds to a carbon or hydrogen atom are replaced with one or more bonds (including double or triple bonds) to a heteroatom. Where multiple substituent moieties are disclosed or claimed, the substituted compound can be singly or multiply independently substituted with one or more of the disclosed or claimed substituent moieties. By independently substituted, it is meant that the (two or more) substituents can be the same or different. In selecting compounds of the present invention, one of ordinary skill in the art will recognize that the various substituents should be selected according to known principles of chemical structure connectivity.

[0191] As used herein, "H" refers to a hydrogen atom. "C" refers to a carbon atom. "N" refers to a nitrogen atom. "O" refers to an oxygen atom. "Halo" refers to F, Cl, Br, or I. As used herein, the term "hydroxy" refers to an -OH moiety. "Br" refers to a bromine atom. "Cl" refers to a chlorine atom. "I" refers to an iodine atom. "F" refers to a fluorine atom. "Acyl group" refers to the group -C(O)-R, where R is a suitable substituent, such as an acetyl group, a propionyl group, a butyroyl group, a benzoyl group, or an alkylbenzoyl group. As used herein, "alkyl" refers to a straight or branched chain hydrocarbon containing 1 or 2 to 10 or 20 or more carbon atoms (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, etc.). In some embodiments, alkyl can be a lower alkyl. "Lower alkyl" refers to a straight or branched chain alkyl having 1 to 3, or 1 to 5, or 1 to 8 carbon atoms. Representative examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n-nonyl, n-decyl, and the like. As used herein, identification of a carbon number range, e.g., C1-C12 alkyl, is intended to include each of the component carbon number moieties within such range, such that subranges of carbon numbers within a specified carbon atom range can be independently designated by including each intervening carbon number and any other stated or intervening carbon number within that stated range. For example, C1-C12 alkyl includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl, and as noted above includes straight-chain and branched groups, and the carbon number range C1-C12 alkyl can also be more specifically specified as subranges such as C1-C4 alkyl, C2-C8 alkyl, C2-C4 alkyl, C3-C5 alkyl, or other subranges within a broader carbon number range.Additionally, carbon number ranges that specifically exclude one or more carbon numbers are contemplated, as are subranges that exclude either or both of the carbon number ranges within the specified range. As generally understood by those skilled in the art, "saturated" refers to a state in which all available valence bonds of an atom (e.g., carbon) are attached to other atoms. Similarly, "unsaturated" refers to a state in which not all available valence bonds are attached to other atoms. In such compounds, the extra bonds typically take the form of double or triple bonds (usually to carbon). For example, a carbon chain is "saturated" (e.g., carbonyl) when there are no double or triple bonds along the chain or directly attached to the chain, and is "unsaturated" when there is at least one double or triple bond along the chain or directly attached to the chain (e.g., carbonyl). Furthermore, those skilled in the art will understand that the presence or absence of a substituent determined by chain saturation is determined by the valence requirements of the atom or atoms (e.g., carbon) to which the substituent is attached. As used herein, "alkenyl" refers to a straight or branched chain hydrocarbon group containing 1 or 2 to 10 or 20 or more carbon atoms and structurally containing at least one carbon-carbon double bond, for example, formed by the replacement of two hydrogens. Representative examples of "alkenyl" include, but are not limited to, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, 2-heptenyl, 2-methyl-1-heptenyl, and 3-decenyl. As used herein, "alkynyl" refers to a straight or branched chain hydrocarbon group containing 1 or 2 to 10 or 20 or more carbon atoms and containing at least one carbon-carbon triple bond. Representative examples of alkynyl include, but are not limited to, acetylenyl, 1-propynyl, 2-propynyl, 3-butynyl, 2-pentynyl, and 1-butynyl. As used herein, the term "cycloalkyl" refers to a saturated cyclic hydrocarbon group containing 3 to 8 or more carbons.

[0192] As understood in the art, the term "optionally substituted" indicates that the specified group is unsubstituted or substituted with one or more suitable substituents. A "substituted" "substituent" is an atom or group that replaces a hydrogen atom on a parent chain or ring of an organic molecule. As used herein, "heterocycle" refers to a monocyclic, bicyclic, or tricyclic ring system. Monocyclic heterocyclic ring systems are exemplified by any 5- to 9-membered ring containing 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, N, and S. As used herein, "aryl" refers to a ring system containing one or more aromatic rings. Representative examples of aryl include azulenyl, indanyl, indenyl, naphthyl, phenyl, and tetrahydronaphthyl. "Heteroaryl" refers to a cyclic aromatic hydrocarbon in which one or more carbon atoms are replaced by a heteroatom (e.g., N, O, or S). When a heteroaryl group contains multiple heteroatoms, the heteroatoms may be the same or different. As used herein, "alkoxy" refers to an alkyl group, as defined herein, attached to the parent molecular moiety through an oxy group, as defined herein. "Amine" or "amino" refers to the group -NH. A "primary amine" is one in which one of the three hydrogen atoms is replaced with an alkyl or aromatic group. A "secondary amine" has two organic substituents attached to the nitrogen with one hydrogen. A "tertiary amine" has three organic substituents attached to the nitrogen. As used herein, "amide" refers to a functional group having a carbonyl group (C=O) attached to the nitrogen atom (N), or an organic compound containing this group, and is generally depicted as follows:

[0193] [ka] where R and R' can independently be any covalently linked atom or atoms. As used herein, the term "oxo" refers to a =O moiety. As used herein, the term "oxy" refers to a -O- moiety. "Nitro" refers to NO, a functional group of organic compounds. "Carbonyl" is a functional group having a carbon atom double-bonded to an oxygen atom (-C=O). As used herein, "carboxy" refers to a -COOH functional group, written as -COH or -(C=O)-OH.

[0194] It will be understood that the compounds, compositions, and methods provided herein may, in some embodiments, be further specified by conditions or limitations that exclude, where applicable, particular substituents, groups, moieties, structures, components, steps, or conditions related to the various broader designations and examples set forth herein.

[0195] "Agriculturally acceptable carriers" of the present invention include, but are not limited to, adjuvants, mixers, accelerators, and the like useful in the application of the formulas. Suitable carriers should not be phytotoxic to valuable crops and should not chemically react with the compounds of the formulas herein or other composition components, particularly at concentrations used in applying the compositions for selective weed control in the presence of crops. Such mixtures can be designed for direct application to weeds or their locus, or can be concentrates or formulations that are typically diluted with additional carriers and adjuvants before application. They can contain inert or active ingredients and can be solids, such as dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as emulsifiable concentrates, solutions, emulsions, or suspensions. Suitable agricultural carriers useful for formulating the agricultural compositions of the present invention are known to those skilled in the art. For example, liquid carriers that can be used include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, etc. Water is generally the carrier of choice for diluting concentrates. Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgas clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonire clay, acid clay, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, etc.

[0196] It is often desirable to incorporate one or more surfactants into the compositions of the present invention. Such surfactants are advantageously used in both solid and liquid compositions, especially those designed to be diluted with a carrier before application. Surfactants can be anionic, cationic, or nonionic in character and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Representative surfactants include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts, such as calcium dodecylbenzene sulfonate; nonylphenol-C 18 Alkylphenol-alkylene oxide adducts such as ethoxylates; Tridecyl alcohol-C 16 alcohol-alkylene oxide adducts such as ethoxylate; soaps such as sodium stearate; sodium dibutylnaphthalenesulfonate alkylnaphthalenesulfonate salts; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters.

[0197] Other adjuvants commonly utilized in agricultural compositions include antifoaming agents, compatibilizers, sequestering agents, neutralizing and buffering agents, corrosion inhibitors, dyes, odorants, penetration aids, spreading agents, adhesives, dispersants, thickeners, freezing point depressants, antimicrobial agents, etc. The compositions may also contain other compatible ingredients, such as other herbicides, plant growth regulators, fungicides, insecticides, etc., and may be formulated with liquid fertilizers or solid particulate fertilizer carriers such as ammonium nitrate, urea, etc.

[0198] "Agriculturally acceptable salts" is intended to mean salts that retain the biological effectiveness of the free acid and free base of the particular compound and that are not biologically or otherwise undesirable. Examples of agriculturally acceptable salts include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, phosphate, monohydrogenphosphate, dihydrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, acetate, propionate, decanoate, caprylate, acrylate, formate, isobutyrate, caprylate, heptanoate, propiolate, oxalate, malonate, succinate, suberate, sebacate, fumarate, maleate, butyne-1,4-iodide, hexyne, and the like. benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, hydroxybenzoate, methoxybenzoate, phthalate, sulfonate, xylenesulfonate, phenylacetate, phenylpropionate, phenylbutyrate, citrate, lactate, gamma-hydroxybutyrate, glycolate, tartrate, methanesulfonate, propanesulfonate, naphthalene-1-sulfonate, naphthalene-2-sulfonate, and mandelate salts.

[0199] Throughout this application, various embodiments of the present invention may be presented in a range format. It should be understood that the description in range format is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the invention. Accordingly, the description of a range should be considered to specifically disclose all possible subranges as well as individual numerical values within that range. For example, description of a range such as 1 to 6 should be considered to specifically disclose subranges such as 1 to 3, 1 to 4, 1 to 5, 2 to 4, 2 to 6, 3 to 6, etc., as well as individual numerical values within that range, e.g., 1, 2, 3, 4, 5, and 6. This applies regardless of the breadth of the range.

[0200] Whenever a numerical range is given herein, it is meant to include any recited number (fractional or integer) within the range given. The phrases "ranging within / between" a first designated number and a second designated number and "ranging within / between" a first designated number "to" a second designated number are used interchangeably herein and include the first and second designated numbers and all fractional and integer numbers therebetween.

[0201] For clarity, certain features of the invention that are described in the context of separate embodiments may also be provided in combination in a single embodiment. Conversely, various features of the invention that are, for brevity, described in the context of a single embodiment may also be provided separately or in any suitable subcombination, or in any other described embodiment of the invention, as appropriate. Certain features described in the context of various embodiments are not to be considered essential features of those embodiments, unless the embodiment is inoperable without those elements.

[0202] As used herein, the term "method" refers to methods, means, techniques, and procedures for performing a given task, including, but not limited to, methods, means, techniques, and procedures known to or readily developed from known methods, means, techniques, and procedures by practitioners in the chemical, agricultural, biological, and biochemical arts.

[0203] As used herein, the term "plant growth regulator" refers to, but is not limited to, a compound, either natural or synthetic, that modifies or controls one or more specific physiological processes in a plant.

[0204] As used herein, the term "plant" refers to, but is not limited to, whole plants, plant ancestors and progeny, and plant parts such as seeds, shoots, stems, roots (including tubers), and plant cells, tissues, and organs. Plants can be in any form, such as suspension cultures, embryos, meristematic regions, callus tissue, leaves, gametophytes, sporophytes, pollen, and microspores.

[0205] As used herein, the term "crop protection agent" refers to, but is not limited to, an agent that is a pesticide (or a mixture of pesticides) or a plant growth regulator.

[0206] As used herein, the term "pesticide" refers to, but is not limited to, a chemical or biological agent that deters, neutralizes, kills, or otherwise discourages pests.

[0207] The compounds of the present invention are generally used as herbicidal active ingredients in compositions. As used herein, the term "composition" refers to a formulation containing at least one additional ingredient selected from the group consisting of surfactants, solid diluents that function as carriers, and liquid diluents, but is not limited thereto. The formulation or composition ingredients are selected to match the physical properties of the active ingredient, the application form, and environmental factors, such as the type of oil, moisture, and temperature. Useful compositions can include both liquid and solid formulations. Liquid formulations can include solutions (including emulsifiable concentrates), suspensions, emulsions (such as aqueous emulsions, oil-in-water emulsions, flowables, and / or suspensions), which can be thickened to form gels. Common types of water-based liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, aqueous emulsions, oil-in-water emulsions, flowables, and suspoemulsions. Common types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions.

[0208] Common types of solid formulations include dusts, powders, granules, pellets, prills, lozenges, tablets, and fill films (such as seed coatings), which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatments. Active ingredients can be (micro)encapsulated and further formed into suspensions or solid formulations. Alternatively, the entire formulation of the active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Spray formulations are typically extended with a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted with the spray vehicle, usually water, but can also be another suitable vehicle such as an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about one to several thousand liters per hectare, but more typically range from about tens to several hundred liters per hectare. Spray formulations can be tank-mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the plant's growing medium. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.

[0209] Formulations typically contain effective amounts of active ingredient, diluent, and surfactant within the approximate ranges below which total 100 weight percent (eight).

[0210] The compounds of the present invention have herbicidal activity (both pre-emergence and post-emergence). As used herein, the term "controlling undesirable plant growth" refers to killing, damaging, or reducing the growth of vegetation.

[0211] The compounds and compositions of this invention can be usefully applied by a variety of methods which involve contacting a herbicidally effective amount of a compound of this invention, or a composition comprising said compound and at least one surfactant, solid diluent, or liquid diluent, with the leaves or other parts of the undesirable plants, or with the environment in which the undesirable plants are growing, such as the soil or water in which the undesirable plants are growing or surrounding seeds or other propagations of the undesirable plants.

[0212] The herbicidally effective amount of the compounds of the present invention will depend on many factors: the formulation selected, the method of application, the amount and type of undesired plant growth present, growing conditions, etc. Generally, the herbicidally effective amount of the compounds of the present invention will be about 0.001 to 20 kg / ha, with a preferred range being about 0.004 to 1 kg / ha. One of ordinary skill in the art can readily determine the herbicidally effective amount required to achieve the desired level of weed control.

[0213] The compounds of the invention, typically in the form of a formulated composition, are applied to a locus containing desired vegetation (e.g., crops) and undesired plant growth (i.e., weeds), both of which may be seeds, seedlings, and / or larger plants in contact with a growing medium (e.g., soil). At this locus, a composition containing a compound of the invention can be applied directly to the plant or any part of the plant, particularly any part of the undesired plant growth, and / or to the growing medium in contact with the plant.

[0214] The compounds of the present invention can also be mixed with one or more other bioactive compounds or agents, such as herbicides, herbicide safeners, fungicides, insecticides, nematicides, bactericides, acaricides, plant growth regulators such as insect molting inhibitors and root stimulants, chemical sterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other bioactive compounds, or bacteria, viruses, or fungi, to form multi-component pesticides that provide a broader agricultural protection spectrum. Mixtures of the compounds of the present invention with other herbicides can further expand the spectrum of activity against additional weed species and suppress the growth of resistant biotypes.

[0215] Throughout this application, various publications, published patent applications and published patents are cited. The disclosures of these publications in their entireties are hereby incorporated by reference into this application in order to more fully describe the state of the art to which this invention pertains.

[0216] Certain features of the invention that are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any suitable subcombination, or as suitable with any other described embodiment of the invention. Certain features described in the context of various embodiments are not to be considered essential features of those embodiments, unless the embodiment cannot function without those elements.

Claims

1. A compound having the following structure or a salt thereof: 【Chemical 1】 [In the formula, A is a 5-, 6-, or 9-membered ring containing 1 to 3 heteroatoms; each heteroatom is independently selected from the group consisting of N, S, and O; and one or more of the carbon atoms of the ring is R ３ , R ４ , R ６ and R ７ may be substituted with R ３ , R ４ , R ６ or R ７ each of R is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); ３ , R ４ , R ６ or R ７ is EDG, then at least one carbon of said ring is replaced with EWG; and one to three heteroatoms of said ring are N or S, each independently R ３ , R ４ , R ６ and R ７ may be substituted with; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyl, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is 【Chemistry 2】 and R １ is selected from the group consisting of esters of saturated or unsaturated alcohols with carboxyl groups, carbamoyl groups, linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, carboxamides substituted with sulfonamides and phosphoramides; R ２ is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides.

2. 2. The compound of claim 1, wherein A is selected from the group consisting of pyrrole, pyrazole, imidazole, triazole, thiophene, dithiol, trithiol, thiazole, dithiazole, trithiazolidine, thiadiazole, dithiadiazole, thiatriazole, oxazole, furan, oxathiol, pyridine, pyridazine, pyrimidine, pyrazine, triazine, thiazine, dithiazine, thiadiazine, 2H-1,3,4,5-thiatriazine, dithiadiazine, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, thiopyranopyrrole, pyrrolothiazine, pyrrolodithiazine, and thienopyridine.

3. 3. The compound of claim 2, wherein A is selected from the group consisting of thiophene, 1H-pyrazole, 2H-1,3-dithiol, 3H-1,2-dithiol, 1H-pyrrole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 1,3-thiazole, 1,2,5-thiadiazole, 1,2,4-thiadiazole, 1,3-oxazole, furan, and pyridine.

4. 4. The compound according to any one of claims 1 to 3, wherein EWG is selected from the group consisting of triflyl (trifluoromethanesulfonyl), trihalide, cyano, sulfonate, nitro, ammonium, quaternary amine, aldehyde, ketone, carboxylic acid, ester, amide, and halide.

5. The compound of any one of claims 1 to 4, wherein EDG is selected from the group consisting of phenoxide, tertiary amine, secondary amine, primary amine, ether, alkyl, phenyl, and vinyl.

6. R ２ is selected from the group consisting of primary, secondary, and tertiary amines substituted with a group selected from hydrogen, a linear or branched aliphatic compound, a non-aromatic ring-containing aliphatic compound, a linear or branched alcohol, a non-aromatic ring-containing alcohol, a terminal carbon of a carboxylic acid, a phosphoric acid, a phosphonic acid, a phosphonate, ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol.

7. R ２ is selected from the group consisting of carboxamides, sulfonamides, and phosphoramides with saturated or unsaturated straight, branched, or cyclic chains.

8. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 3】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ３ H ７ and R ２ is NH ２ and R ３ and R ７ are independently H, CF ３ , CCl ３ , Cl and F; R ４ and R ６ are independently selected from H, Cl, and Br.

9. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 4】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , and COOC ３ H ７ is selected from: R ２ is NH ２ and R ３ and R ４ are independently selected from H, Br, and Cl; R ６ and R ７ are independently H, Cl, NO ２ , C.F. ３ and CCl ３ is selected from.

10. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 5】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ４ H ９ , CONHCH ２ COOH, and COO(CH ２ ) ３ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , NHCO, and NH(CH ２ ) ２ O (CH ２ ) ２ ) OH; R ３ and R ４ are independently H, Cl, Br, CN, CHF ２ , C.F. ３ , CCl ３ is selected from: R ６ is H or CF ３ It is.]

11. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 6】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ and R ３ and R ４ are independently selected from H, Br, and Cl; R ６ are H, F, Cl, Br, and CF ３ , CCl ３ is selected from.

12. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 7】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ３ and R ４ are each independently H, Br, Cl, and NH ２ is selected from.

13. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 8】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ or NHCOC ２ H ５ is selected from: R ４ and R ６ are each independently H, Br, Cl, or CF ３ , CHF ２ , and CCl ３ is selected from.

14. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 9】 [In the formula, R １ is selected from the group consisting of COOH; R ２ is NH ２ and R ６ is H.]

15. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 10】 [In the formula, R １ is selected from the group consisting of OH; R ２ is NH ２ and R ３ and R ６ are both H.]

16. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 11】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ６ is H, Br, Cl, CF ３ , CCl ３ and N.H. ２ is selected from.

17. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 12】 [In the formula, R １ is OH; R ２ is NH ２ and R ３ , R ４ and R ６ are independently H, Br, Cl, CF ３ , CCl ３ , and N.H. ２ is selected from.

18. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 13】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ６ is H, Br, Cl, CF ３ , CCl ３ and N.H. ２ is selected from.

19. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 14】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ３ and R ５ are independently H, Br, Cl, CF ３ , CCl ３ is selected from: R ６ is CH ３ , OH and NH ２ is selected from.

20. The compound of any one of claims 1 to 7, having the structure: 【Chemistry 15】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ or NHCOC ２ H ５ is selected from: R ３ and R ５ are independently H, Br, Cl, CF ３ , CCl ３ is selected from: R ４ is CH ３ , OH and NH ２ is selected from.

21. 21. An agricultural composition comprising a compound according to any one of claims 1 to 20 and at least one agriculturally acceptable carrier.

22. 22. The agricultural composition of claim 21, further comprising at least one crop protection agent.

23. 23. The agricultural composition of claim 22, wherein the at least one crop protection agent is selected from the group consisting of fungicides, insecticides, herbicides, and plant growth regulators.

24. 24. The agricultural composition of claim 23, wherein the crop protection agent is a herbicide.

25. 24. The agricultural composition of claim 23, wherein the crop protection agent is a plant growth regulator.

26. the at least one crop protection agent is atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl, prosulfuron , primisulfuron-methyl, dicamba, fluthiacet-methyl, pyridate, 2,4-D, clopyralid, diflufenzopyr, fluroxypyr, MCPA, MCPB, mecoprop (MCPP), metobenzuron, thifensulfuron-methyl, aclonifen, EPTC, glyphosate, glufosinate, sulfosate, cyanazine, propaquizafop, metamitron, pyramine, phenmedipham, desmedipham, ethofumesate, triasulfuron, chloridazon, lenacil, triallate, fluazifop, sethoxydim, quizalofol clopyralid, clethodim, oxasulfuron, acifluorfen, benazolin-ethyl, sulfentrazone, chlorimuron-ethyl, chloransulam-methyl, fomesafen, imazamox, imazaquin, imazethapyr, imazapyr, lactofen, fenoxaprop (P-ethyl), thidiazuron, tribufos, trifluralin, dimethachlor, napropamide, quinmerac, metazachlor, carbetamide, dimefuron, propyzamide, ethametsulfuron-methyl, tebutam, fluometuron, prometryn, norflurazon, pyrimidin Thiobac-sodium, MSMA, DSMA, diuron, flurochloridone, dithiopyr, thiazopyr, oxyfluorfen, ethalfluralin, clodinafop, amidosulfuron, diclofop-methyl, diflufenican, ethoxysulfuron, fentrazamide, flazasulfuron, florasulam, fluazolate, flucarbazone, flupyrsulfuron-methyl sodium, flutamone, iodosulfuron, isoproturon, chlortoluron, chlorsulfuron, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, 2,4-DB, 2,4-DP, Bifenox, Flamprop-M, Imazamethabenz-methyl, Ioxynil, Trakoxydim, Fluoroglycofen-ethyl, Methabenzthiazuron, Isoxaben, Prosulfocarb, Difenzoquat-methylsulfate, Pretilachlor, Cinosulfuron, Fenclorim, Bensulfuron-methyl, Imazosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Esprocarb, Mefenacet, Molinate, Propanil, Pyrazolate, Cyhalofop-butyl, Bispyribac-sodium, Pyriminobac-methyl, Caffentrol, Oxadiargyl, Oxadiazon, Bromobutide, MY-100, Dimron, NB 061, MK243, HW-52, AC 25. The agricultural composition according to claim 24, wherein the active ingredient is selected from the group consisting of 014, ametryn, hexazinone, asulam, azafenidin, tebuthiuron, ethametsurfuron-methyl, or a combination thereof.

27. 27. A method for controlling undesired plant growth, comprising applying to the locus of said undesired plant growth an agricultural composition according to any one of claims 21 to 26.

28. 1. A method for controlling undesirable plant growth, comprising applying to the locus of said undesirable plant growth a herbicidally effective amount of a compound having the structure: or a salt thereof. 【Chemistry 16】 [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each heteroatom is independently selected from the group consisting of N, S, and O; and one or more of the carbon atoms of said ring is R ３ , R ４ , R ６ and R ７ may be substituted with R ３ , R ４ , R ６ or R ７ each of R is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); ３ , R ４ , R ６ or R ７ is EDG, then at least one carbon of said ring is replaced with EWG; and when one or more heteroatoms of said ring are N or S, then each is independently R ３ , R ４ , R ６ and R ７ may be substituted with; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyls, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is 【Chemistry 17】 and R １ is selected from the group consisting of esters of saturated or unsaturated alcohols with carboxyl groups, carbamoyl groups, linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, carboxamides substituted with sulfonamides and phosphoramides; R ２ is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides.

29. 29. The method of claim 28, wherein A is selected from the group consisting of pyrrole, pyrazole, imidazole, triazole, thiophene, dithiol, trithiol, thiazole, dithiazole, trithiazolidine, thiadiazole, dithiadiazole, thiatriazole, oxazole, furan, oxathiol, pyridine, pyridazine, pyrimidine, pyrazine, triazine, thiazine, dithiazine, thiadiazine, 2H-1,3,4,5-thiatriazine, dithiadiazine, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, thiopyranopyrrole, pyrrolothiazine, pyrrolodithiazine, and thienopyridine.

30. 30. The method of claim 28 or 29, wherein A is selected from the group consisting of thiophene, 2H-1,3-dithiol, 3H-1,2-dithiol, 1H-pyrrole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 1,3-thiazole, 1,2,5-thiadiazole, 1,2,4-thiadiazole, 1,3-oxazole, furan, and pyridine.

31. 31. The method of any one of claims 28 to 30, wherein the EWG is selected from the group consisting of triflyl (trifluoromethanesulfonyl), trihalide, cyano, sulfonate, nitro, ammonium, quaternary amine, aldehyde, ketone, carboxylic acid, ester, amide, and halide.

32. 32. The method of any one of claims 28 to 31, wherein the EDG is selected from the group consisting of phenoxide, tertiary amine, secondary amine, primary amine, ether, alkyl, phenyl, and vinyl.

33. R ２ is selected from the group consisting of hydrogen, aliphatic compounds having a straight or branched chain, aliphatic compounds having a non-aromatic ring, straight or branched alcohols, alcohols having a non-aromatic ring, terminal carbon atoms of phosphoric acid, phosphonic acid, phosphonate, primary, secondary, and tertiary amines substituted with a group selected from ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol.

34. R ２ is selected from the group consisting of carboxamides, sulfonamides, and phosphoramides with saturated or unsaturated straight, branched, or cyclic chains.

35. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemistry 18】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ３ H ７ and R ２ is NH ２ and R ３ and R ７ are independently H, CF ３ , CCl ３ , Cl and F; R ４ and R ６ are independently selected from H, Cl and Br.

36. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemistry 19】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , and COOC ３ H ７ is selected from: R ２ is NH ２ and R ３ and R ４ are independently selected from H, Br, and Cl; R ６ and R ７ are independently H, Cl, NO ２ , C.F. ３ and CCl ３ is selected from.

37. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemistry 20】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ４ H ９ , CONHCH ２ COOH, and COO(CH ２ ) ３ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , NHCO, and NH(CH ２ ) ２ O (CH ２ ) ２ ) OH; R ３ and R ４ are independently H, Cl, Br, CN, CHF ２ , C.F. ３ , CCl ３ is selected from: R ６ is H or CF ３ It is.]

38. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical 21】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ and R ３ and R ４ are independently selected from H, Br, and Cl; R ６ are H, F, Cl, Br, and CF ３ , CCl ３ is selected from.

39. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical 22】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ３ and R ４ are each independently H, Br, Cl, and NH ２ is selected from.

40. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical 23】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ or NHCOC ２ H ５ is selected from: R ４ and R ６ are each independently H, Br, Cl, or CF ３ , CHF ２ , and CCl ３ is selected from.

41. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemistry 24】 [In the formula, R １ is COOH; R ２ is NH ２ and R ６ is H.]

42. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemistry 25】 [In the formula, R １ is OH; R ２ is NH ２ and R ３ and R ６ are both H.]

43. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical 26】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ６ is H, Br, Cl, CF ３ , CCl ３ and N.H. ２ is selected from.

44. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical 27】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ６ is H, Br, Cl, CF ３ , CCl ３ and N.H. ２ is selected from.

45. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical formula 28】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ , or NHCOC ２ H ５ is selected from: R ３ and R ５ are independently H, Br, Cl, CF ３ , CCl ３ is selected from: R ６ is CH ３ , OH and NH ２ is selected from.

46. 35. The method of any one of claims 28 to 34, comprising applying to the locus of undesired plant growth a herbicidally effective amount of a compound having the structure: 【Chemical 29】 [In the formula, R １ COOH, COOCH ３ , COOC ２ H ５ , COOC ５ H １１ , and COO(CH ２ ) ２ (CH ２ ) ２ CH ３ is selected from: R ２ is NH ２ , NHCOCH ３ or NHCOC ２ H ５ is selected from: R ３ and R ５ are independently H, Br, Cl, CF ３ , CCl ３ is selected from: R ４ is CH ３ , OH and NH ２ is selected from.

47. 47. The method of any one of claims 28 to 46, further comprising applying at least one crop protection agent to the locus of undesired plant growth.

48. 48. The method of claim 47, wherein the at least one crop protection agent is selected from the group consisting of herbicides, fungicides, insecticides, and plant growth regulators.

49. 49. The method of claim 48, wherein the crop protection agent is a herbicide.

50. 50. The method of claim 49, wherein the crop protection agent is an amino acid synthesis inhibitor herbicide.

51. 51. The method of claim 50, wherein the amino acid synthesis inhibitor herbicide is selected from the group consisting of sulfonylurea herbicides, imidazolinone herbicides, sulfonamide herbicides and amino acid derivatives, or combinations thereof.

52. 52. The method of claim 51, wherein the amino acid synthesis inhibitor herbicide is selected from the group consisting of imazamox, imazapic, imazethapyr, imazaquin, imazapyr, and imazamethabenz, or combinations thereof.

53. 52. The method of claim 51 , wherein the amino acid synthesis inhibitor herbicide is selected from the group consisting of chlorimuron, primisulfuron, thifensulfuron, triasulfuron, nicosulfuron, metsulfuron, tribenuron, rimsulfuron, and triflusulfuron, or combinations thereof.

54. 52. The method of claim 51, wherein the amino acid synthesis inhibitor herbicide is glyphosate.

55. 51. The method of claim 50, wherein the crop protection agent is a plant growth regulator.

56. 58. The method of claim 57, wherein the plant growth regulator is selected from the group consisting of dicamba, 2,4-D, clopyralid, and fluroxypyr.

57. 1. A method of controlling undesired plant growth, comprising administering to a locus of said undesired plant growth: a. a first herbicide or a salt thereof having the following structure: 【Chemistry 30】 [In the formula, A is a 5-, 6-, or 9-membered ring containing one or more heteroatoms; each of said heteroatoms is independently selected from the group consisting of N, S, and O; and one or more carbon atoms of said ring are bonded to R ３ , R ４ , R ６ and R ７ may be substituted with R ３ , R ４ , R ６ or R ７ each is independently selected from an electron withdrawing group (EWG) or an electron donating group (EDG); ３ , R ４ , R ６ or R ７ is EDG, then at least one carbon of said ring is replaced with EWG; and when one or more heteroatoms of said ring are N or S, then each is independently R ３ , R ４ , R ６ and R ７ may be substituted with; T is selected from the group consisting of sulfonyl, ammonium, alkylamine; arylamine, phosphonium, nitro, cyano, dihalomethyl, acyl, formyl, haloformyls, carboxyl, alkoxycarbonyl, and aminocarbonyl; n is 0 or 1; y is 0 to 8; X is 【Chemical 31】 and R １ is selected from the group consisting of carboxamides substituted with carboxyl groups, carbamoyl groups, esters of saturated or unsaturated alcohols having aliphatic linear, branched, cyclic or aromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, linear, branched, cycloaliphatic chains, cycloaromatic chains, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, sulfonamides, and phosphoramides; R ２ is selected from the group consisting of optionally substituted primary amines, secondary amines, tertiary amines, carboxamides, sulfonamides, and phosphoramides; and b. a second herbicide to effectively control said undesired plant growth. applying a

58. 58. The method of claim 57, wherein the second herbicide is an amino acid synthesis inhibitor herbicide.

59. 59. The method of claim 58, wherein the second herbicide is selected from the group consisting of sulfonylurea herbicides, imidazolinone herbicides, sulfonamide herbicides, and amino acid derivatives.

60. 60. The method of any one of claims 57 to 59, wherein the second herbicide is selected from the group consisting of imazamox, imazapic, imazethapyr, imazaquin, imazapyr, imazamethabenz, chlorimuron, primisulfuron, thifensulfuron, triasulfuron, nicosulfuron, metsulfuron, tribenuron, rimsulfuron, triflusulfuron, and glyphosate.

61. the second herbicide is atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metoslam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl, prosulfuron, primisulf Lon-methyl, dicamba, fluthiacet-methyl, pyridate, 2,4-D, clopyralid, diflufenzopyr, fluroxypyr, MCPA, MCPB, mecoprop (MCPP), metobenzuron, thifensulfuron-methyl, aclonifen, EPTC, glyphosate, glufosinate, sulfosate, cyanazine, propaquizafop, metamitron, pyramine, phenmedipham, desmedipham, ethofumesate, triasulfuron, chloridazon, lenacil, triallate, fluazifop, sethoxydim, quizalofop, clopyra Lid, clethodim, oxasulfuron, acifluorfen, benazolin-ethyl, sulfentrazone, chlorimuron-ethyl, chloransulam-methyl, fomesafen, imazamox, imazaquin, imazethapyr, imazapyr, lactofen, fenoxaprop (P-ethyl), thidiazuron, tribufos, trifluralin, dimethachlor, napropamide, quinmerac, metazachlor, carbetamide, dimefuron, propyzamide, ethametsulfuron-methyl, tebutam, fluometuron, prometryn, norflurazon, pyrithiobac-na Thorium, MSMA, DSMA, diuron, flurochloridone, dithiopyr, thiazopyr, oxyfluorfen, ethalfluralin, clodinafop, amidosulfuron, diclofop-methyl, diflufenican, ethoxysulfuron, fentrazamide, flazasulfuron, florasulam, fluazolate, flucarbazone, flupyrsulfuron-methyl sodium, flutamone, iodosulfuron, isoproturon, chlortoluron, chlorsulfuron, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, 2,4-DB, 2,4-DP, Bifenox, Flamprop-M, Imazamethabenz-methyl, Ioxynil, Trakoxydim, Fluoroglycofen-ethyl, Methabenzthiazuron, Isoxaben, Prosulfocarb, Difenzoquat-methylsulfate, Pretilachlor, Cinosulfuron, Fenclorim, Bensulfuron-methyl, Imazosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Esprocarb, Mefenacet, Molinate, Propanil, Pyrazolate, Cyhalofop-butyl, Bispyribac-sodium, Pyriminobac-methyl, Caffentrol, Oxadiargyl, Oxadiazon, Bromobutide, MY-100, Dimron, NB 061, MK243, HW-52, AC The method according to any one of claims 57 to 59, wherein the active ingredient is selected from the group consisting of 014, ametryn, hexazinone, asulam, azafenidin, tebuthiuron, and ethametsurfuron-methyl.

62. 62. The method of any one of claims 57 to 61, further comprising applying a third herbicide or plant growth regulator.

63. 1. A composition for controlling undesirable plant growth, comprising: a. The compound according to any one of claims 1 to 22: b. atrazine, terbuthylazine, (S)-metolachlor, metolachlor, terbutryn, simazine, dimethenamid, (S)-dimethenamid, flufenacet, acetochlor, alachlor, isoxaflutole, isoxachlortole, mesotrione, sulcotrione, metosulam, flumetsulam, pendimethalin, bromoxynil, bentazone, carfentrazone-ethyl, clomazone, nicosulfuron, rimsulfuron, halosulfuron-methyl, metribuzin, flumiclorac-pentyl, prosulfuron, primisulfuron-methyl, Dicamba, fluthiacet-methyl, pyridate, 2,4-D, clopyralid, diflufenzopyr, fluroxypyr, MCPA, MCPB, mecoprop (MCPP), metobenzuron, thifensulfuron-methyl, aclonifen, EPTC, glyphosate, glufosinate, sulfosate, cyanazine, propaquizafop, metamitron, pyramine, phenmedipham, desmedipham, ethofumesate, triasulfuron, chloridazon, lenacil, triallate, fluazifop, sethoxydim, quizalofop, clopyralid, cleopyralid, Thodim, oxasulfuron, acifluorfen, benazolin-ethyl, sulfentrazone, chlorimuron-ethyl, chloransulam-methyl, fomesafen, imazamox, imazaquin, imazethapyr, imazapyr, lactofen, fenoxaprop (P-ethyl), thidiazuron, tribufos, trifluralin, dimethachlor, napropamide, quinmerac, metazachlor, carbetamide, dimefuron, propyzamide, ethametsurofuron-methyl, tebutam, fluometuron, prometryn, norflurazon, pyrithiobac-sodium um, MSMA, DSMA, diuron, flurochloridone, dithiopyr, thiazopyr, oxyfluorfen, ethalfluralin, clodinafop, amidosulfuron, diclofop-methyl, diflufenican, ethoxysulfuron, fentrazamide, flazasulfuron, florasulam, fluazolate, flucarbazone, flupyrsulfuron-methyl sodium, flutamone, iodosulfuron, isoproturon, chlortoluron, chlorsulfuron, metsulfuron-methyl, sulfosulfuron, tribenuron-methyl, 2,4-DB, 2,4-DP, Bifenox, Flamprop-M, Imazamethabenz-methyl, Ioxynil, Trakoxydim, Fluoroglycofen-ethyl, Methabenzthiazuron, Isoxaben, Prosulfocarb, Difenzoquat-methylsulfate, Pretilachlor, Cinosulfuron, Fenclorim, Bensulfuron-methyl, Imazosulfuron, Pyrazosulfuron-ethyl, Azimsulfuron, Esprocarb, Mefenacet, Molinate, Propanil, Pyrazolate, Cyhalofop-butyl, Bispyribac-sodium, Pyriminobac-methyl, Caffentrol, Oxadiargyl, Oxadiazon, Bromobutide, MY-100, Dimron, NB 061, MK243, HW-52, AC At least one herbicide selected from the group consisting of 014, ametryn, hexazinone, asulam, azafenidin, tebuthiuron, and ethametsurfuron-methyl, or combinations thereof; and c. at least one agriculturally acceptable carrier A composition comprising a mixture of:

64. 1. A composition for controlling undesirable plant growth, comprising: a) a compound according to any one of claims 1 to 22; b. at least one plant growth regulator; and c. at least one agriculturally acceptable carrier A composition comprising:

65. 2-Amino-3-(thiophen-2-yl)propanoic acid; 2-Amino-3-(thiophen-3-yl)propanoic acid; 2-Amino-3-[(thiophene-3-sulfonyl)amino]propanoic acid; 2-Amino-3-[(4-fluorothiophene-3-sulfonyl)amino]propanoic acid; Methyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; Pentyl 2-amino-3-[(thiophene-3-sulfonyl)amino]propanoate; 3-(5-cyano-3-thienyl)alanine; 2-Amino-3-[4-(trifluoromethyl)thiophen-2-yl]propanoic acid; 3-amino-3-(4-bromothiophen-3-yl)propanoic acid; 2-amino-3-(2,4,5-trimethylthiophen-3-yl)propanoic acid; Butyl 2-amino-3-(thiophen-3-yl)propanoate; 2-Amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoic acid; 2-Amino-3-[(2,5-dichloro-4-methylthiophene-3-sulfonyl)amino]propanoic acid; 2-Amino-3-(2-chlorothiophene 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid; 2-amino-3-(5-chlorothiophen-3-yl)propanoic acid; 2-amino-3-(2,5-dihydro-1,3-thiazol-4-yl)propanoic acid; 2-amino-3-(1,3-thiazol-5-yl)propanoic acid; 2-amino-3-{[2,5-dichloro-4-(trifluoromethyl)thiophene-3-sulfonyl]amino}propanoic acid; 2-amino-3-(2-amino-1,3-thiazol-4-yl)propanoic acid; Methyl 2-amino 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate; Ethyl 2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate; 2-Propoxyethyl-2-amino-3-[(2,5-dichlorothiophene-3-sulfonyl)amino]propanoate; [2-(carboxyamino)-3-ethoxy-3-oxopropyl](2,5-dichlorothiophene-3-sulfonyl)carbamic acid; 2-amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid; 2-amino 2-amino-3-(5-chloro-1,3-thiazol-4-yl)propanoic acid; 2-amino-3-(1,2,5-thiadiazol-3-yl)propanoic acid; 2-amino-3-(1,2,4-thiadiazol-5-yl)propanoic acid; 2-amino-3-(furan-3-yl)propanoic acid; 2-amino-3-(1,3-oxazol-4-yl)propanoic acid; 2-formamido-3-(thiophen-3-yl)propanoic acid; methyl 2-amino-3-(thiophen-3-yl)propanoate; ethyl 2-amino-3-(thiophen-3-yl)propanoate;[2-amino-3-(thiophen-3-yl)propanamido]acetic acid; 2-amino-N-[2-(2-hydroxyethoxy)ethyl]-3-(thiophen-3-yl)propenamide; Ethyl 2-butanamido-3-(dichloro-1,3-thiazol-4-yl)propanoate; 2-butoxyethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate; 2-amino-3-(2,5-dibromothiophen-3-yl)propanoic acid; 2-amino-3-(5-nitrothiophen-3-yl)propanoic acid; Butyl 3-(dichloro-1,3-thiazol-4-yl)-2-acetamidopropanoate; 2-ethoxyethyl 3-(dichloro-1,3-thiazol-4-yl)-2-acetamidopropanoate; 2-amino-3-[5-(trifluoromethyl)thiophen-3-yl]propanoic acid; (2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid; 2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoic acid; 2-amino-3-(5-chloro-2-methylthiophen-3-yl)propanoic acid; 2-amino-3-(2-bromothiophen-3-yl)propanoic acid; 2-amino-3-(1,1-dioxo-116-thiolan-3-yl)propanoic acid; 2-amino-3-(thiolan-3-yl)propanoic acid; [2-amino-2-(thiophen-3-yl)ethyl]phosphonic acid; 2-Amino-3-(2,5-dimethyl-1,1-dioxo-1H-116-thiophen-3-yl)propanoic acid; 3-(2,5-dioxo-2,5-dihydrothiophen-3-yl)-2-(phosphonoamino)propanoic acid; 2-Amino-3-[4-(trifluoromethyl)thiophen-3-yl]propanoic acid; Ethyl 2-acetamido-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoate; Methyl Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate; Ethyl 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoate; 2-(2-methoxyethoxy)ethyl-2-amino-3-(thiophen-3-yl)propanoate; Ethyl 2-acetamido-3-(thiophen-3-yl)propanoate; Ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamido 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate; ethyl 3-(2,5-dichlorofuran-3-yl)-2-acetamidopropanoate; propyl 2-amino-3-(2,5-dichlorofuran-3-yl)propanoate; 4-(2-acetamido-3-ethoxy-3-oxopropyl)-3-methyl-1,3-thiazol-3-ium chloride; 2-(2-ethoxyethoxy)ethyl 3-(2,5-dichlorothiophen-3-yl)-2-acetamidopropanoate Amidopropanoate; Pentyl 2-acetamido-3-(1,3,4-oxadiazol-2-yl)propanoate; Ethyl-2-amino-3-[(2,5-dibromothiophene-3-sulfonyl)amino]propanoate; Butyl 3-(5-chloro-1,2,4-thiadiazol-3-yl)-2-acetamidopropanoate; 2-Amino-3-(1H-indazol-3-yl)propanoic acid hydrochloride [HCl]; 2-Amino-3-(pyridazin-4-yl)propanoic acid; 2-Amino-3-(pyridin-4-yl)propanoic acid; 2-Amino-3-(pyridin-3-yl)propanoic acid dihydrochloride; 3-(5-hydroxy-3-pyridinyl)alanine; 2-amino-3-(5-methylpyridin-3-yl)propanoic acid; 2-amino-3-(4-aminopyridin-2-yl)propanoic acid; 2-amino-3-(2-aminopyridin-4-yl)propanoic acid; 2-amino-3-(6-aminopyridin-2-yl)propanoic acid; 2-amino-3-(5-aminopyridin-3-yl)propanoic acid; 2-amino-3-(5-sulfanylpyridin-3-yl)propanoic acid; 2-amino-3-(2-sulfanylpyridin-4-yl)propanoic acid; 2-amino-3-(pyrimidin-5-yl)propanoic acid; 2-amino 2-amino-3-(4-amino-6-chloropyrimidin-2-yl)propanoic acid; 2-amino-3-(pyrimidin-2-yl)propanoic acid dihydrochloride; 2-amino-3-(4-hydroxypyrimidin-2-yl)propanoic acid; 2-amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanoic acid; 2-amino-3-(pyrazin-2-yl)propanoic acid; 2-amino-3-(5-chloropyridin-3-yl)propanoic acid; 2-amino-3-(2,5-dichloropyridin-3-yl)propanoic acid; 2-amino-3 -(pyrimidin-4-yl)propanoic acid; 2-amino-3-(5-fluoropyridin-3-yl)propanoic acid; 2-amino-3-(6-chloropyridin-3-yl)propanoic acid; 2-amino-3-(2,6-dichloropyridin-4-yl)propanoic acid; 2-amino-3-(3,5-dichloropyridin-4-yl)propanoic acid; 2-amino-3-(3,5-difluoropyridin-4-yl)propanoic acid; 2-amino-3-[2-(dimethylamino)pyridin-4-yl]propanoic acid; 2-amino-3-(2-bromopyridin-4-yl)propanoic acid ;2-amino-3-(5,6-dibromopyridin-3-yl)propanoic acid; 2-amino-3-(2,6-dibromopyridin-4-yl)propanoic acid; 2-amino-3-(2,3-dibromopyridin-4-yl)propanoic acid; 2-amino-3-[5-(trifluoromethyl)pyridin-3-yl]propanoic acid; 2-amino-3-(5,6-dichloropyridin-3-yl)propanoic acid; 2-amino-3-(2-oxo-1,2-dihydropyridin-4-yl)propanoic acid; 2-amino-3-[4-(dimethylamino)pyridin-3-yl]propanoic acid; 2-amino-3-(2-oxo-1,2-dihydropyridin-3-yl)propanoic acid; 2-amino-3-(6-oxo-1,6-dihydropyrimidin-4-yl)propanoic acid; 2-amino-3-(6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid; 2-amino-3-(6-oxo-1,6-dihydropyridin-3-yl)propanoic acid; 2-amino-3-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)propanoic acid; 2-amino-3-(6-oxo-2-sulfanyl-1,6-dihydropyrimidin-4-yl)propanoic acid; Propyl 2-amino-3-(2-bromopyridin-4-yl)propanoate; 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoic acid; Propyl 2-amino-3-(2-bromo-3,5-difluoropyridin-4-yl)propanoate; 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoic acid; Propyl 2-amino-3-[(2-bromopyridine-4-sulfonyl)amino]propanoate; Ethyl 2-amino-3-(5,6-dibromopyridin-3-yl)propanoate; Ethyl 2-amino-3-(2,3-dibromopyridin-4-yl)propanoate acid; 2-amino-3-[2-chloro-5-(trifluoromethyl)pyridin-3-yl]propanoic acid; 2-amino-3-(2-amino-6-oxo-1,6-dihydropyrimidin-5-yl)propanoic acid; 2-amino-3-(6-hydroxy-5-nitropyridin-3-yl)propanoic acid 2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid; Methyl 2-amino-3-(2-bromopyridin-4-yl)propanoate; 3-(2-amino-2-carboxyethyl)-1-methylpyridin-1-ium; 3-(2-amino-2-carboxyethyl)-1-hydroxypyridin-1-ium; 2-Amino-3-(4-amino-6-hydroxy-2-methylpyrimidin-5-yl)propanoic acid; Methyl 2-amino-3-(2,6-dibromopyridin-4-yl)propanoate; Ethyl 3-(6-bromopyridin-3-yl)-2-acetoacetate Amidopropanoate; Methyl 3-(6-bromopyridin-3-yl)-2-acetamidopropanoate; Ethyl-2-acetamido-3-(2-methoxypyrimidin-4-yl)propanoate; 2-(2-methoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate; 2-(2-ethoxyethoxy)ethyl 2-amino-3-(6-bromopyridin-3-yl)propanoate; 5-(2-amino-2-carboxyethyl)-1-methylpyrimidin-1-ium; 2-amino-3-[ 2-(Trifluoromethyl)pyridin-4-yl]propanoic acid hydrochloride [HCl]; Ethyl 3-[(2-bromopyridin-4-yl)oxy]-2-acetamidopropanoate; Ethyl 2-acetamido-3-(pyridin-4-yloxy)propanoate; 2-Amino-4-(1H-pyrrol-3-yl)butanoic acid; 2-Amino-3-(1H-pyrrol-2-yl)propanoic acid; 2-Amino-3-(1H-pyrrol-3-yl)propanoic acid; 2-Amino-3-(4H-1,2,4-triazol-3-yl)propanoic acid; (2S)-2-Hydroxy-3-(1H-imidazol-4-yl)propanoic acid; Ethyl 2-{[(benzyloxy)carbonyl]amino}-3-(1H-1,2,4-trimethylamino)propanoate 2-Amino-3-(4-methyl-4H-1,2,4-triazol-3-yl)propanoate; 2-Amino-3-(4-methyl-4H-1,2,4-triazol-3-yl)propanoic acid; 2-Amino-3-(1-methyl-1H-1,2,4-triazol-5-yl)propanoic acid dihydrochloride; 2-Amino-3-(1-methyl-1H-1,2,3-triazol-4-yl)propanoic acid hydrochloride; 2-Amino-3-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)propanoic acid hydrochloride; 2-Amino-3-(dimethyl-4H-1,2,4-triazol-3-yl)propanoic acid hydrochloride; (2S)-2-Amino-3-[5-(trifluoromethyl)-1H-pyrazol-4-yl]propanoic acid; and 2-(2-butoxyethoxy)ethyl 2-amino-3-(2H-1,2,3-triazol-4-yl)propanoate, or an agriculturally acceptable salt thereof.

66. 66. An agricultural composition comprising a compound of claim 65 and at least one agriculturally acceptable carrier.

67. 66. A method for controlling undesired plant growth, comprising applying to the locus of said undesired plant growth a herbicidally effective amount of the compound of claim 65.

68. 67. A method for controlling undesired plant growth, comprising applying to the locus of said undesired plant growth a herbicidally effective amount of the agricultural composition of claim 66.

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