Strigolactone analogues and their use

Patent metadata

Field	Value
Publication number	US-9326510-B2
Application number	US-201514645823-A
Country	US
Kind code	B2
Filing date	Mar 12, 2015
Priority date	Apr 28, 2011
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

Novel compounds of formula (I)

their use as germination trap for parasitic weeds, for the regulation of branching, tillering and root development, for enhancement of cambium growth, for the regulation of hyphal growth of mycorrhizal fungi and compositions comprising compounds of formula (I) and insecticides and/or fungicides.

First claim

The invention claimed is:

1. A compound of general formula I:

wherein:
R a is hydrogen;
R b is hydrogen;
R c is C 1 -C 8 alkyl,
R f is hydrogen;
R d is C 1 -C 8 alkyl, wherein the hydrogen atoms of the alkyl may be partly replaced by other groups or atoms;
R e represents a substituent R 1 which represents C 1 -C 8 -alkyl, C 2 -C 8 alkenyl, C 2 -C 8 -alkinyl, C 3 -C 8 -cycloalkyl or C 1 -C 8 -alkoxy, in each of which the hydrogen atoms may be partly replaced by other groups or atoms; or —CH═CH—R 7 , wherein R 7 represents a hydrogen atom, C 1 -C 8 -alkyl or a 4-, 5- 6- or 7-membered saturated or unsaturated, aromatic or non-aromatic carbocyclic or heterocyclic ring or a fused ring system containing more than one of those rings.

2. A compound in accordance with claim 1 , wherein R c is a C 1 -C 4 alkyl group.

3. A compound in accordance with claim 1 , wherein R c is methyl.

4. A compound in accordance with claim 1 , wherein R d is methyl.

5. A compound in accordance with claim 1 , wherein R c is methyl and R d is methyl.

6. A compound in accordance with claim 1 , wherein R e is represented by —CH═CH—R 7 , wherein R 7 represents a hydrogen atom, C 1 -C 8 -alkyl or a 4-, 5- 6- or 7-membered saturated or unsaturated, aromatic or non-aromatic carbocyclic or heterocyclic ring, or a fused ring system containing more than one of those rings.

7. A compound in accordance with claim 1 , wherein R e is represented by —CH═CH—R 7 , wherein R 7 is a five- or six-membered carbocyclic ring which may be saturated or unsaturated.

8. A compound in accordance with claim 1 , wherein R e is represented by —CH═CH—R 7 , wherein R 7 is represented by a cyclohexenyl ring which may be substituted.

9. A compound in accordance with claim 1 , wherein R e is represented by —CH═CH—R 7 , wherein R 7 is represented by a cyclohexenyl ring which is substituted with a hydroxyl group, a C 1 -C 8 alkyl, a C 1 -C 8 alkoxy, or acetyl group.

10. A compound in accordance with claim 1 , wherein R e represents a C 1 -C 8 alkyl or a C 2 -C 8 alkenyl group, optionally substituted with a hydroxyl group or a carbonyl group or a cycloalkyl group which itself might be substituted.

11. A composition comprising at least one compound according to claim 1 and also at least one insecticide, fungicide, or herbicide.

12. A method for controlling the germination of parasitic root plants, wherein a compound is used as a germination trap in which the compound is represented by the following:

wherein R a , R b and R c , independently from each other, represent:
a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyloxy group, a formylamino group or a carbamate group,
a substituent R 1, wherein R 1 represents C 1 -C 8 -alkyl-, C 2 -C 8 alkenyl, C 2 -C 8 -alkinyl, C 3 -C 8 -cycloalkyl or C 1 -C 8 -alkoxy, in each of which the hydrogen atoms may be partly replaced by other groups or atoms,
a substituent —OR 2 , wherein R 2 represents a hydrogen atom, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 -alkinyl, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -alkylaminocarbonyl, or C 1 -C 8 -alkoxycarbonyl, in each of which the hydrogen atoms may be partly replaced by other groups or atoms
a substituent —NR 3 R 4 , wherein R 3 and R 4 , independently from each other, represent a hydrogen atom, C 1 -C 8 alkyl, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl, phenyl or benzyl, in each of which the hydrogen atoms may be partly replaced by other groups or atoms,
a substituent—C(O)—R 5 , wherein R 5 represents a hydrogen atom, C 1 -C 8 -alkyl or C 1 -C 8 -alkyloxy, in each of which the hydrogen atoms may be partly replaced by other groups or atoms,—NH2, NHR 5 or NR 5 R 5 (where the two substituents R 5 may be the same or different), —NR 5 (OH),
a substituent —S(O)n-R 6 , wherein n is 0, 1 or 2 and R6 represents C 1 -C 8 -alkyl in which the hydrogen atoms may be partly replaced by other groups or atoms, —NH 2 , —NHR 6 or NR 6 R 6 (where the two substituents R 6 may be the same or different),
or a 4-, 5-, 6- or 7-membered heterocyclic ring comprising up to 4 heteroatoms selected from nitrogen, oxygen or sulfur, where in each of these rings the hydrogen atoms may be partly replaced by other groups or atoms,
R d represents
C 1 -C 8 alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkinyl, wherein the hydrogen atoms may be partly replaced by other groups or atoms,
R e represents
a substituent R 1 as defined above, or —CH═CH-R 7 , wherein R 7 represents a hydrogen atom, C 1 -C 8 -alkyl or a 4-, 5- 6- or 7-membered saturated or unsaturated , aromatic or non-aromatic carbocyclic or heterocyclic ring or a fused ring system containing more than one of those rings
R d and R e together form a 4-,5-6- or 7-membered saturated or unsaturated , aromatic or non-aromatic carbocyclic or heterocyclic ring, which may be fused to another saturated or unsaturated , aromatic or non-aromatic carload ie or heterocyclic ring with the proviso that the carbon atom carrying substituents R d and R e is not part of an enone-structural element, and
R f represents
a hydrogen atom, halogen atom, a nitro group, a cyano group or C 1 -C 8 -alkyl-, C 2 -C 8 alkenyl, C 2 -C 8 -alkinyl or C 3 -C 8 -cycloalkyl.

13. A method according to claim 12 , wherein for the compound of formula I R a and R b are hydrogen and R c is a substituent R 1 .

14. A method according to claim 12 , wherein the R c is C 1 -C 8 -alkyl.

15. A method according to claim 12 , the compound is represented by one of the following formulae:

16. A method according to claim 12 , wherein the compound is represented by formula IA:

17. The method of claim 12 , wherein the compound is a compound according to claim 1 .

18. The method of claim 12 , wherein the parasitic root plant is a parasitic weed.

19. The method according to claim 12 , wherein the parasitic root plant is a Striga or a Orobanche plant.

Assignees

• Univ King Abdullah Sci & Tech

Inventors

• Al-Babili Salim
• Alder Adrian

Classifications

• C12P17/04

  containing a five-membered hetero ring, e.g. griseofulvin {, vitamin C} · CPC title

• C07D307/58 Primary

  One oxygen atom, e.g. butenolide · CPC title

• A01N43/08 Primary

  with oxygen as the ring hetero atom · CPC title

• C12P5/002

  cyclic (compounds containing at least three condensed carbocyclic rings C12P15/00) · CPC title