Strigolactone formulations and uses thereof
Disclosed herein plant propagation materials, methods of manufacturing, formulations and uses thereof. The plant propagation materials disclosed herein may comprise a strigolactone obtained by a biosynthetic process. The plant propagation material may comprise a chemical mimic of a strigolactone. The strigolactone may be 5-deoxystrigol. Methods of manufacturing the plant propagation materials may comprise a chemical process. Alternatively, methods of manufacturing the plant propagation material may comprise a biosynthetic process. The methods may comprise use of one or more polynucleotides. The polynucleotides may encode a metabolite. The polynucleotides may comprise one or more genes encoding one or more components of a strigolactone pathway.
1. A compound of Formula (I), a salt, solvate, diastereoisomer, stereoisomer, or isomer thereof:
wherein:
a, b, and c are one of the following:
i) a is 0 or 2, and b and c are each independently 0, 1, or 2;
ii) a is 1, b is 0, and c is 0 or 2;
iii) a is 1, b is 1, and c is 1 or 2; or
iv) a is 1, b is 2, and c is 0, 1, or 2;
each A is independently O, or S;
each E is independently O, S, or —NR 18 ;
each G is independently C;
R 5 , R 6 , R 11 , R 12 , R 14 , R 15 and R 17 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ;
R 2 , R 3 , R 7 , R 8 , R 9 , and R 10 are each independently H, alkyl, haloalkyl, amino, halo, —OR 18 or a lone electron pair;
R 1 and R 16 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 1 and R 16 together form a direct bond to provide a double bond;
R 4 and R 13 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 4 and R 13 together form a direct bond to provide a double bond;
each R 18 is independently H, alkyl, haloalkyl, aryl, heteroaryl, —C(O)R 19 or
and
each R 19 is independently H, alkyl, haloalkyl, aryl, or heteroaryl.
2. A compound of Formula (II), a salt, solvate, diastereoisomer, stereoisomer, or isomer thereof:
wherein:
a, b, c are each independently 0, 1, or 2;
each A is independently O, or S;
each E is independently O, S, or —NR 18 ;
each G is independently C;
R 5 , R 6 , R 11 , R 12 , R 14 , R 15 and R 17 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ;
R 2 , R 3 , R 7 , R 8 , R 9 , and R 10 are each independently H, alkyl, haloalkyl, amino, halo, —OR 18 or a lone electron pair;
R 1 and R 16 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 1 and R 16 together form a direct bond to provide a double bond;
R 4 and R 13 are each independently H, alkyl, haloalkyl, amino, halo, or —OR 18 ; or R 4 and R 13 together form a direct bond to provide a double bond;
each R 18 is independently H, alkyl, haloalkyl, aryl, heteroaryl, —C(O)R 19 or
and
each R 19 is independently H, alkyl, haloalkyl, aryl, or heteroaryl.
3. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein a is 1, b is 2, and c is 0.
4. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein each A is independently O.
5. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein each E is independently O.
6. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 1 , R 11 , R 12 , and R 16 are each independently H.
7. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein R 5 , R 6 , R 13 , and R 17 are each independently alkyl.
8. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 7 , wherein R 5 , R 6 , R 13 , and R 17 are each independently methyl.
9. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 8 , having the structure of Formula (III):
10. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 8 , having the structure of Formula (IV):
11. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein the compound, salt, solvate, diastereoisomer, stereoisomer, or isomer has a diastereomeric excess of at least 50%.
12. A formulation comprising the compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 .
13. A method comprising contacting a plant with the compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 or the formulation of claim 12 .
14. A method of making a formulation comprising forming the formulation with the compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 .
15. A method of producing the compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 comprising alkylating
or a salt thereof, wherein R 17 is H, alkyl, halo, or haloalkyl and X is Cl, Br, or I.
16. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein in the moiety:
the stereocenter * is selected from the group consisting of: (S), (R), racemic, and a non-racemic mixture of (R) and (S).
17. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 9 or 10 , wherein in the moiety:
the stereocenter * is selected from the group consisting of: (S), (R), racemic, and a non-racemic mixture of (R) and (S).
18. A plant, food, or seed comprising the compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 or the formulation of claim 12 .
19. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein a is 1, b is 2, and c is 0, 1, or 2.
20. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein a is 1, b is 1, and c is 1 or 2.
21. The formulation of claim 12 , further comprising an excipient.
22. The formulation of claim 21 , wherein the excipient comprises water, a surfactant, an alcohol, or any combination thereof.
23. The formulation of claim 22 , comprising the surfactant, wherein the surfactant comprises a sulfosuccinate, a naphthalene sulfonate, a sulfated ester, a phosphate ester, a sulfated alcohol, an alkyl benzene sulfonate, a polycarboxylate, a naphthalene sulfonate condensate, a phenol sulfonic acid condensate, a lignosulfonate, a methyl oleyl taurate, a polyvinyl alcohol, or any combination thereof.
24. The formulation of claim 12 , further comprising a fertilizer.
25. The formulation of claim 24 , wherein the fertilizer comprises nitrogen fertilizer, phosphate fertilizer, potassium fertilizer, calcium fertilizer, magnesium fertilizer, sulfur fertilizer, compound fertilizer, organic fertilizer, or any combination thereof.
26. The formulation of claim 12 , further comprising an insecticide, a fungicide, a herbicide, or any combination thereof.
27. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , wherein a is 1, b is 0, and c is 0 or 2.
28. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , comprising the salt of the compound of Formula (I).
29. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , comprising the solvate of the compound of Formula (I).
30. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , comprising the diastereoisomer of the compound of Formula (I).
31. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , comprising the stereoisomer of the compound of Formula (I).
32. The compound, salt, solvate, diastereoisomer, stereoisomer, or isomer of claim 1 , comprising the isomer of the compound of Formula (I).