Brassinosteroid mimetics
View Patent ↗The disclosure provides brassinosteroid mimetics and method of using such mimetics.
1. A method to activate the brassinosteroid response in a plant, comprising applying a compound of Formula I(a) to the plant or in the root zone of the plant, wherein Formula I(a) comprises:
wherein,
R 2 , R 3 , R 5 , R 7 , R 10 -R 14 are independently selected from H, D, NH 2 , —O-alkyl, —O-ether, SH, optionally substituted (c 1 -C 12 )alkyl, optionally substituted hetero(C 1 -C 12 )alkyl, optionally substituted (C 2 -C 12 )alkenyl, optionally substituted hetero(C 2 -C 12 )alkenyl, optionally substituted (C 2 -C 12 )alkynyl, optionally substituted hetero(C 2 -C 12 )alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, hydroxyl, halo, imine, amide, nitro, nitroso, nitrile, isocyanate, ester, aldehyde, ketone, carboxyl, thiol, thionyl, and sulfonyl; and
R 15 is an optionally substituted (C 1 -C 6 )alkyl, an optionally substituted hetero-(C 1 -C 6 )alkyl, an optionally substituted (C 2 -C 6 )alkenyl, an optionally substituted hetero-(C 2 -C 6 )alkenyl, an optionally substituted (C 2 -C 6 )alkynyl, or an optionally substituted hetero-(C 1 -C 6 )alkynyl, a cycloalkyl, an aryl, and a heterocycle.
2. A composition for promoting plant growth comprising a brassinosteroid mimetic as set forth in Formula I(a) in a suitable delivery vehicle, wherein Formula I(a) comprises:
wherein,
R 2 , R 3 , R 5 , R 10 -R 14 are independently selected from H, D, NH 2 , —O-alkyl, —O-ether, SH, optionally substituted (c 1 -C 12 )alkyl, optionally substituted hetero(C 1 -C 12 )alkyl, optionally substituted (C 2 -C 12 )alkenyl, optionally substituted hetero(C 2 -C 12 )alkenyl, optionally substituted (C 2 -C 12 )alkynyl, optionally substituted hetero(C 2 -C 12 )alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, hydroxyl, halo, imine, amide, nitro, nitroso, nitrile, isocyanate, ester, aldehyde, ketone, carboxyl, thiol, thionyl, and sulfonyl;
R 7 is selected from D, NH 2 —O-alkyl, —O-ether, SH, optionally substituted (c 1 -C 12 )alkyl, optionally substituted hetero(C 1 -C 12 )alkyl, optionally substituted (C 2 -C 1 )alkenyl, optionally substituted hetero(C 2 -C 1 )alkenyl, optionally substituted (C 2 -C 1 )alkynyl, optionally substituted hetero(C 2 -C 1 )alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, hydroxyl, halo, imine, amide, nitro, nitroso, nitrile, isocyanate, ester, aldehyde, ketone, carboxyl, thiol, thionyl, and sulfonyl; and
R 15 is an optionally substituted (C 1 -C 6 )alkyl, an optionally substituted hetero-(C 1 -C 6 )alkyl, an optionally substituted (C 1 -C 6 )alkenyl, an optionally substituted hetero-(C 1 -C 6 )alkenyl, an optionally substituted (C 1 -C 6 )alkynyl, or an optionally substituted hetero-(C 1 -C 6 )alkynyl, a cycloalkyl, an aryl, and a heterocycle.
3. The composition of claim 2 further comprising a formulating agent.
4. A method of promoting plant growth by applying to a plant an effective amount of the composition of claim 2 .
5. A method of promoting a desired tissue morphology and/or physiological state in a higher plant, wherein said desired tissue morphology or physiological state is selected from at least one of: shoot growth, grain, seed or fruit yield enhancement, root (radicle) growth retardation, improved fruit set and fruit quality or other desired tissue morphology or physiological state that is promoted by a brassinosteroid, the method comprising applying to the plant an effective amount of a brassinosteroid mimetic of Formula I(a):
wherein,
R 2 , R 3 , R 5 , R 7 , R 10 -R 14 are independently selected from H, D, NH 2 , —O-alkyl, —O-ether, SH, optionally substituted (C 1 -C 12 )alkyl, optionally substituted hetero(C 1 -C 12 )alkyl, optionally substituted (C 2 -C 12 )alkenyl, optionally substituted hetero(C 2 -C 12 )alkenyl, optionally substituted (C 2 -C 12 )alkynyl, optionally substituted hetero(C 2 -C 12 )alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, hydroxyl, halo, imine, amide, nitro, nitroso, nitrile, isocyanate, ester, aldehyde, ketone, carboxyl, thiol, thionyl, and sulfonyl; and
R 15 is an optionally substituted (C 1 -C 6 )alkyl, an optionally substituted hetero-(C 1 -C 6 )alkyl, an optionally substituted (C 2 -C 6 )alkenyl, an optionally substituted hetero-(C 2 -C 6 )alkenyl, an optionally substituted (C 2 -C 6 )alkynyl, or an optionally substituted hetero-(C 1 -C 6 )alkynyl, a cycloalkyl, an aryl, and a heterocycle.
6. The method of claim 5 wherein the brassinosteroid mimetic is applied in conjunction with a plant growth regulator and a formulating agent.
7. A composition for promoting plant growth comprising a brassinosteroid mimetic as set forth in Formula I(a) in a suitable delivery vehicle, wherein Formula I(a) comprises:
wherein,
R 2 , R 3 , R 5 , R 7 , R 10 -R 14 are independently selected from H, D, NH 2 , —O-alkyl, —O-ether, SH, optionally substituted (c 1 -C 12 )alkyl, optionally substituted hetero(C 1 -C 12 )alkyl, optionally substituted (C 2 -C 12 )alkenyl, optionally substituted hetero(C 2 -C 12 )alkenyl, optionally substituted (C 2 -C 12 )alkynyl, optionally substituted hetero(C 2 -C 12 )alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl, optionally substituted heterocycle, hydroxyl, halo, imine, amide, nitro, nitroso, nitrile, isocyanate, ester, aldehyde, ketone, carboxyl, thiol, thionyl, and sulfonyl; and
R 15 is an optionally substituted hetero-(C 1 -C 6 )alkyl, an optionally substituted (C 2 -C 6 )alkenyl, an optionally substituted hetero-(C 2 -C 6 )alkenyl, an optionally substituted (C 2 -C 6 )alkynyl, or an optionally substituted hetero-(C 2 -C 6 )alkynyl, a cycloalkyl, an aryl, and a heterocycle.
8. The composition of claim 7 further comprising a formulating agent.
9. A method of promoting plant growth by applying to a plant an effective amount of the composition of claim 7 .