3′-alkynyl abscisic acid derivatives as ABA antagonists
The present application relates to novel 3′-unsaturated abscisic acid (ABA) derivatives of Formula (I) as ABA antagonists. For example, the present application relates to methods of using compounds of Formula (I) for reducing adverse effects of an ABA response in plants such as lentil and promoting germination. (I) The present application also relates to methods of using 3′-phenyl abscisic acid (ABA) derivatives of Formula (II) as ABA antagonists, for example, for reducing adverse effects of an ABA response in plants such as lentil and promoting germination. (II)
1. A compound of Formula (I) or an enantiomer, salt, and/or solvate thereof:
wherein
L is —C═C— or —C≡C—;
R 1 is C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, or (CH 2 ) 0-2 heteroaryl, each being optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl, or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl; and
R 2 is H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, cycloalkyl, aryl, heterocycloalkyl or heteroaryl, the latter 7 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl,
wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
2. The compound of claim 1 , wherein R 1 is (CH 2 ) 0-2 aryl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
3. The compound of claim 1 , wherein R 1 is aryl optionally substituted with one or more of OH, halo, C 1-10 alkyl, OC 1-6 alkyl, or O(CH 2 ) 0-2 aryl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
4. The compound of claim 1 , wherein R 1 is C 1-10 alkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl, or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
5. The compound of claim 4 , wherein R 1 is C 1-10 alkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
6. The compound of claim 1 , wherein R 1 is C 2-10 alkenyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
7. The compound of claim 1 , wherein R 1 is (CH 2 ) 0-2 C 3-10 cycloalkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl, or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
8. The compound of claim 7 , wherein R 1 is C 3-10 cycloalkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.
9. The compound of claim 1 , wherein R 2 is H or C 1-10 alkyl.
10. The compound of claim 1 , wherein L is —C═C—.
11. The compound of claim 1 , wherein L is —C≡C—.
12. The compound of Formula (I) or a salt, and/or solvate thereof of claim 1 , wherein the compound has the following stereochemistry:
13. The compound of Formula (I) of claim 1 selected from the compounds listed below:
Compound I.D
Structures
1018
1019
1021
1022
1023
1024
1025
1059
1063
1090
1091
1100
or a salt, and/or solvate thereof.
14. A method for reducing adverse effects of an ABA response in a plant in need thereof comprising administering an effective amount of one or more compounds of claim 1 or salt and/or solvate thereof to the plant.
15. The method of claim 14 , wherein the adverse effects of an ABA response include delayed or inhibited seed germination and/or plant dessication, over-ripening of fruit, slow bud breaking and/or slow plant growth.
16. The method of claim 14 , wherein the adverse effects of an ABA response occur under stress conditions.
17. A method for reducing adverse effects of an ABA response in a plant in need thereof comprising administering an effective amount of one or more compounds of the Formula (II) or an enantiomer, salt, and/or solvate thereof, to the plant,
wherein:
n is 0, 1, 2 or 3;
R 3 is selected from OH, halo, C 1-10 alkyl, OC 1-6 alkyl, and O(CH 2 ) 0-2 aryl, the latter 3 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl; and
R 4 is selected from H or C 1-10 alkyl,
wherein each alkyl, alkenyl, and alkynyl is optionally fluorosubstituted, and
provided the compound of Formula II is not
18. The method of claim 17 , wherein the effective amount of the compound is about 0.1 μM to about 600 μM.
19. The method of claim 14 , wherein the plant is canola, lentil, chickpea, Arabidopsis , faba bean, soybean, corn, rice, wheat, rye, barley, or fruit plant.
20. The method of claim 14 , wherein one or more compounds of claim 1 or salt and/or solvate thereof is administered in combination with other known agents useful for regulating plant development.
21. The method of claim 17 , wherein the effective amount of the compound is about 1 μM to about 500 μM.
22. The method of claim 17 , wherein the effective amount of the compound is about 5 μM to about 250 μM.