Strigolactone analogues and the use thereof for the treatment of plants

Patent metadata

Field	Value
Publication number	US-9532569-B2
Application number	US-201314403132-A
Country	US
Kind code	B2
Filing date	May 23, 2013
Priority date	May 23, 2012
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

A compound of general formula (I):

in which X represents O, S, NH or an N-alkyl radical, R 1 and R 2 , identical or different, each represent H or a C 1 -C 10 hydrocarbon radical, R 1 and R 2 not both representing H, R 3 represents a C 1 -C 10 hydrocarbon radical, and R represents a phenyl radical monosubstituted or disubstituted by a substituent Y and, if applicable, a substituent Z, chosen from Cl, Br, I and CF 3 , or R represents a C═R 4 (R 5 ) radical in which R 4 represents an hydrocarbon radical and R 5 represents a linear or branched, saturated or unsaturated, hydrocarbon radical, optionally substituted, a COR 6 group or a CO 2 R 6 group, where R 6 represents a hydrogen atom or a linear or branched, saturated or unsaturated, hydrocarbon radical. This compound can be used for the treatment of higher plants for controlling their growth and architecture.

First claim

The invention claimed is:

1. A compound of general formula (I):

in which:
X represents an oxygen atom, a sulfur atom, NH or an N-alkyl radical,
R 1 and R 2 are identical or different, each representing a hydrogen atom or a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical,
provided that R 1 and R 2 not both representing a hydrogen atom,
R 3 represents a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical, and
R represents a phenyl radical monosubstituted with a substituent Y chosen from Cl, Br, I and CF 3 , or a phenyl radical disubstituted with a substituent Y and a substituent Z, Y and Z, which are identical or different, being each chosen from Cl, Br, I and CF 3 , or forming together a saturated or unsaturated or aromatic, optionally substituted, ring which may contain one or more heteroatoms, or
R represents a radical:

where R 4 represents a linear or branched, saturated or unsaturated, C 1 -C 15 hydrocarbon-based radical, and
R 5 represents a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical, optionally substituted, a COR 6 group or a CO 2 R 6 group, where R 6 represents a hydrogen atom or a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical.

2. The compound as claimed in claim 1 , wherein R 3 represents a linear C 1 -C 10 alkyl radical.

3. The compound as claimed in claim 2 , wherein R 3 represents a methyl radical.

4. The compound as claimed in claim 1 , wherein R 1 and R 2 each represent a hydrogen atom or a linear or branched C 1 -C 10 alkyl radical.

5. The compound as claimed in claim 4 , wherein R 1 represents a hydrogen atom and R 2 represents a linear or branched C 1 -C 10 alkyl radical.

6. The compound as claimed in claim 5 , wherein R 2 represents a methyl radical.

7. The compound as claimed in claim 1 , wherein X represents a sulfur atom or an oxygen atom.

8. The compound as claimed in claim 1 , wherein R represents a phenyl radical substituted at least in the para-position.

9. The compound as claimed in claim 1 , of general formula (II):

in which Y is chosen from Cl, Br, I and CF 3 .

10. The compound as claimed in claim 9 , in which Y is a chlorine atom.

11. The compound as claimed in claim 1 , of general formula (II″):

in which:
X represents an oxygen atom, a sulfur atom, NH or an N-alkyl radical,
R 1 and R 2 are identical or different, each representing a hydrogen atom or a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical,
provided that R 1 and R 2 not both representing a hydrogen atom,
R 3 represents a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical,
R 8 , R 9 , R 10 and R 11 , which are identical or different, each representing a hydrogen atom, Cl, Br, I, CF 3 , CHO, CN, NO 2 , a linear or branched, saturated or unsaturated, optionally substituted, hydrocarbon-based radical, or a CO 2 R 12 group, where R 12 represents a hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 10 hydrocarbon-based radical.

12. The compound as claimed in claim 11 , wherein R 12 represents a linear or branched, saturated or unsaturated, C 1 -C 10 hydrocarbon-based radical.

13. The compound as claimed in claim 11 , of general formula (II″) in which R 8 , R 9 , R 10 and R 11 each represent a hydrogen atom.

14. The compound as claimed in claim 1 , wherein R represents a radical:

where R 4 represents a linear or branched C 1 -C 15 alkyl radical or alkenyl radical, and
R 5 represents a linear or branched, C 1 -C 10 , optionally substituted, hydrocarbon-based radical, a COR 6 group or a CO 2 R 6 group, where R 6 represents a linear or branched, C 1 -C 10 hydrocarbon-based radical.

15. The compound as claimed in claim 14 , wherein R 5 represents a linear or branched, C 1 -C 5 , optionally substituted, hydrocarbon-based radical.

16. The compound as claimed in claim 14 , wherein R 5 represents a COR 6 group or a CO 2 R 6 group, where R 6 represents a linear or branched C 1 -C 5 hydrocarbon-based radical.

17. The compound as claimed in claim 14 , in which R 5 represents a linear or branched, C 1 -C 10 hydrocarbon-based radical, which is substituted with an electron-withdrawing group.

18. The compound as claimed in claim 17 , in which R 5 represents a linear or branched unsaturated C 1 -C 10 hydrocarbon-based radical, which is substituted with an electron-withdrawing group.

19. The compound as claimed in claim 17 , in which R 5 represents a linear or branched C 1 -C 5 hydrocarbon-based radical which is substituted with an electron-withdrawing group.

20. The compound as claimed in claim 17 , in which R 5 represents a linear or branched C 1 -C 10 hydrocarbon-based radical, which is substituted at its free end with an electron-withdrawing group.

21. The compound as claimed in claim 17 , wherein said electron-withdrawing group is chosen from: CHO, CN, NO 2 and CO 2 R 7 , where R 7 represents a linear or branched, C 1 -C 10 hydrocarbon-based radical.

22. The compound as claimed in claim 21 , wherein R 7 represents a linear or branched C 1 -C 5 hydrocarbon-based radical.

23. A composition for the treatment of higher plants, comprising a compound as claimed in claim 1 .

24. The composition as claimed in claim 23 , wherein the concentration of said compound is between 0.1 and 1000 nM.

25. The composition as claimed in claim 24 , wherein the concentration of said compound is between 1 and 100 nM.

26. The use of a compound as claimed in claim 1 , for the treatment of a higher plant with a view to controlling the growth and the architecture of said plant.

27. The use as claimed in claim 26 , wherein an appropriate amount of said compound is brought into contact with the plant so as to inhibit the formation of at least one branch.

28. The use as claimed in claim 27 , wherein a composition comprising said compound is applied to an at least partial portion of the aerial part of the plant.

29. The use as claimed in either of claim 27 , wherein a composition comprising said compound is applied to axillary buds of the plant.

30. The use as claimed in claim 27 , wherein a composition comprising said compound is injected into an aerial part of said plant.

31. The use as claimed in claim 27 , wherein a composition comprising said compound is introduced via at least one root of said plant.

32. The use as claimed in claim 27 , wherein the concentration of said compound in said composition is between 0.1 and 1000 nM.

33. The use as claimed in claim 32 , wherein the concentra

Assignees

• Agronomique Inst Nat Rech
• Centre Nat Rech Scient
• Univ De Paris Xi Paris Sud

Inventors

• Boyer Francois-Didier
• Rameau Catherine
• Pillot Jean-Paul
• Servajean Vincent
• De Saint Germain Alexandre
• Beau Jean-Marie
• Pouvreau Jean-Bernard
• Clave Guillaume

Classifications

• C07D307/60

  Two oxygen atoms, e.g. succinic anhydride · CPC title

• C07D307/58

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

• A01N43/08 Primary

  with oxygen as the ring hetero atom · CPC title

• C07D307/56 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D307/68

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title