Strigolactone derivatives

Abstract

The present disclosure relates to derivatives of strigolactone and formulations thereof. The present disclosure also relates to methods of treating a plant to improve, for example, the yield, growth, or vigor of a plant. The disclosed strigolactone derivatives and formulations may be combined with a plant growth regulator, a fertilizer, an insecticide, an herbicide, a fungicide, a urease inhibitor, a nitrification inhibitor, and/or an excipient.

That which is claimed is: 
     
         1 . A formulation comprising:
 (i) a compound of Formula (II):   
       
         
           
           
               
               
           
         
         wherein 
         X and Y are independently O, S, or —NR 7 ; 
         Z is O, S, —NH, or A; 
         R 1 , R 2 , and R 3  are each independently H, amino, halo, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, —OR 8 , —SR 8 , —C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , —C(O)NR 8 ; 
         R 7  and R 8  are each independently H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl; 
         A is a substituted or unsubstituted heterocyclic group or substituted or unsubstituted heteroaryl group; 
         R 9  is H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, —C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , or —C(O)NR 8 ; and 
         n is 1, 2, or 3; 
         or a salt or solvate thereof; and 
         (ii) at least one selected from the group consisting of a plant growth regulator, a fertilizer, an insecticide, an herbicide, a fungicide, a urease inhibitor, a nitrification inhibitor, an excipient, and any combination thereof. 
       
     
     
         2 . The formulation of  claim 1 , wherein R 3  is a substituted or unsubstituted alkyl. 
     
     
         3 . The formulation of  claim 2 , wherein R 9  is H, —C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , or —C(O)NR 8 . 
     
     
         4 . The formulation of  claim 1 , wherein X is O or —NR 7 ; Y and Z are each O; and R 1  and R 2  are each independently H, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. 
     
     
         5 . The formulation of  claim 1 , wherein X is O or —NR 7 ; Y and Z are each O; R 1  and R 2  are each independently H or alkyl; and R 8  is H, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. 
     
     
         6 . The formulation of  claim 1 , wherein X is O or —NR 7 ; Y and Z are each O; and R 1  and/or R 2  is methyl. 
     
     
         7 . The formulation of  claim 1 , wherein X is O or —NR 7 ; Y and Z are each O; R 3  is methyl; and R 8  is H or alkyl. 
     
     
         8 . The formulation of  claim 1 , wherein X is O or —NR 7 ; Y and Z are each O; and R 3  is methyl. 
     
     
         9 . The formulation of  claim 1 , wherein X is O; Y and Z are each O; and R 3  is methyl. 
     
     
         10 . The formulation of  claim 1 , wherein the compound of Formula (II) is present in an amount ranging from about 1% to 99% by weight of the total weight of the formulation. 
     
     
         11 . The formulation of  claim 1 , further comprising water, a surfactant, an alcohol, or any combination thereof. 
     
     
         12 . The formulation of  claim 1 , wherein the formulation comprises the fertilizer and the fertilizer is nitrogen-containing fertilizer, phosphate-containing fertilizer, potassium-containing fertilizer, calcium-containing fertilizer, magnesium-containing fertilizer, sulfur-containing fertilizer, compound fertilizer, and/or organic fertilizer. 
     
     
         13 . The formulation of  claim 1 , wherein the formulation comprises the urease inhibitor and the urease inhibitor is N-(n-butyl)thiophosphoric triamide (NBPT), N-(n-butyl)phosphoric triamide, thiophosphoryl triamide, phenyl phosphorodiamidate, N-cyclohexyl phosphoric triamide, N-cyclohexyl thiophosphoric triamide, phosphoric triamide, hydroquinone, p-benzoquinone, hexamidocyclotriphosphazene, thiopyridines, thiopyrimidines, thiopyridine-N-oxides, N,N-dihalo-2-imidazolidinone, N-halo-2-oxazolidinone, N-(2-nitrophenyl)thiophosphoric triamide, or N-(2-nitrophenyl)phosphoric triamide. 
     
     
         14 . A method for hydraulic enhancement of a plant, comprising contacting a plant with a formulation comprising (i) a compound of Formula (II): 
       
         
           
           
               
               
           
         
         wherein 
         X and Y are independently O, S, or —NR 7 ; 
         Z is O, S, —NH, or A; 
         R 1 , R 2 , and R 3  are each independently H, amino, halo, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, —OR 8 , —SR 8 , —C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , —C(O)NR 8 ; 
         R 7  and R 8  are each independently H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl; 
         A is a substituted or unsubstituted heterocyclic group or substituted or unsubstituted heteroaryl group; 
         R 9  is H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, —C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , or —C(O)NR 8 ; and 
         n is 1, 2, or 3; 
         or a salt or solvate thereof; and 
         (ii) at least one selected from the group consisting of a plant growth regulator, a fertilizer, an insecticide, an herbicide, a fungicide, a urease inhibitor, a nitrification inhibitor, an excipient, and any combination thereof. 
       
     
     
         15 . The method of  claim 14 , wherein R 3  is a substituted or unsubstituted alkyl. 
     
     
         16 . The method of  claim 15 , wherein R 9  is H, C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , or —C(O)NR 8 . 
     
     
         17 . The method of  claim 14 , wherein the crop yield of the contacted plant is increased as compared to crop yield of a plant of the same species that is not contacted with the compound of Formula (II). 
     
     
         18 . The method of  claim 14 , wherein transpiration of the contacted plant is increased as compared to transpiration of a plant of the same species that is not contacted with the compound of Formula (II). 
     
     
         19 . The method of  claim 14 , wherein the method comprises contacting the plant with an effective amount of the compound of Formula (II) or a salt or solvate thereof. 
     
     
         20 . A compound of Formula (I): 
       
         
           
           
               
               
           
         
       
       wherein:
 X, Y, and Z are independently O, S, or —NR 7 ; 
 R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are each independently H, amino, halo, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, —OR 8 , —SR 8 , —C(O)R 8 , —C(O)OR 8 , —C(S)R 8 , —C(S)OR 8 , —C(S)SR 8 , —C(O)NR 8 ; 
 or R 4  and R 5  together with the carbons to which they are attached form a cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl ring, which is optionally substituted with one or more substituents selected from amino, halo, alkyl, cycloalkyl, aryl, and oxo; and 
 R 7  and R 8  are each independently H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl; 
 or a salt or solvate thereof.