Synthetic compounds useful as nodulation agents of leguminous plants and preparation processes thereof

1. A compound of formula (I)

(I)

in which

n represents 1, 2 or 3;

A represents a substituent selected from the group consisting of —C(O)—, —C(S)—, and —CH 2 —;

B is selected from the group consisting of

a biphenylene;

this group optionally being substituted with one or two substituents independently selected from the group consisting of halogen, CN, C(O)OR 14 , C(O)NR 15 R 16 , CF 3 , OCF 3 , —NO 2 , N 3 , OR 14 , SR 14 , NR 15 R 16 and C 1-6 -alkyl;

C represents a substituent selected from the group consisting of —O—, —S—, —CH 2 —, and CH—(C 1 -C 6 -alkyl);

D represents a linear or branched, saturated or unsaturated hydrocarbon-based chain containing from 2 to 20 carbon atoms;

E and G represent, independently of each other, a substituent selected from the group consisting of H, OH, OC(O)CH 3 and NHC(O)CH 3 ;

R 1 represents a substituent selected from the group consisting of H, C 1-6 -alkyl, C(O)H and C(O)CH 3 ;

R 2 , R 3 , R 6 , R 14 , R 15 , and R 16 represent, independently of each other, a substituent selected from the group consisting of H, C 1-6 -alkyl, C(O)C 1-6 -alkyl, —C(S)C 1-6 -alkyl, —C(O)OC 1-6 -alkyl, —C(O)NH 2 , —C(S)NH 2 , —C(NH)NH 2 , —C(O)NHC 1-6 -alkyl, —C(S)NHC 1-6 -alkyl and —C(NH)NHC 1-6 -alkyl;

R 4 represents a substituent selected from the group consisting of H, C 1-6 -alkyl and R 21 ;

R 5 represents a substituent selected from the group consisting of H, C 1-6 -alkyl, fucosyl and R 22 ;

R 7 represents a substituent selected from the group consisting of H, C 1-6 -alkyl, arabinosyl and R 23 ;

R 8 represents a substituent selected from the group consisting of H, C 1-6 -alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 alkyl) 4 and R 24 ;

R 9 represents a substituent selected from the group consisting of H, C 1-6 -alkyl, mannose, glycerol and R 25 ;

R 21 , R 22 , R 23 , R 24 and R 25 represent, independently of each other, a substituent selected from the group consisting of C(O)C 1-6 -alkyl, —C(S)C 1-6 -alkyl, —C(O)OC 1-6 -alkyl, —C(O)NH 2 , —C(S)NH 2 , —C(NH)NH 2 , —C(O)NHC 1-6 -alkyl, —C(S)NHC 1-6 -alkyl and —C(NH)NHC 1-6 -alkyl;

and the possible geometrical or optical isomers, enantiomers or diastereoisomers, tautomers, salts, N-oxides, sulfoxides, sulfones, and metal or metalloid complexes thereof that are agriculturally acceptable.

2. The compound of formula (I) of claim 1 wherein:

n represents 2 or 3;

A is selected from the group consisting of —C(O)— and —CH 2 —;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H, CH 3 and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent H;

R 4 is selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 is selected from the group consisting of H, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 alkyl) 4 , fucosyl and methylfucosyl.

3. The compound of claim 2 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

4. The compound of claim 1 wherein A is —C(O)—.

5. The compound of claim 4 wherein:

n represents 2 or 3;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H and CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent H;

R 4 is selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 is selected from the group consisting of H, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 -alkyl) 4 , fucosyl and methylfucosyl.

6. The compound of claim 5 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

7. The compound of claim 1 wherein A is —CH 2 —.

8. The compound of claim 7 wherein

n represents 2 or 3;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent H;

R 4 is selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 is selected from the group consisting of H, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 -alkyl) 4 , fucosyl and methylfucosyl.

9. The compound of claim 8 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

10. The compound of claim 9 wherein C represents —O—.

11. The compound of claim 1 wherein C represents —O—.

12. The compound of claim 11 wherein:

n represents 2 or 3;

A is selected from the group consisting of —C(O)— and —CH 2 —;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H, CH 3 and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent H;

R 4 is selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 is selected from the group consisting of H, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 -alkyl) 4 , fucosyl and methylfucosyl.

13. The compound of claim 12 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

14. The compound of claim 1 wherein A is —C(O)— and C is —O—.

15. The compound of claim 14 wherein:

n represents 2 or 3;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H and CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent H;

R 4 is selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 is selected from the group consisting of H, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 -alkyl) 4 , fucosyl and methylfucosyl.

16. The compound of claim 15 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

17. The compound of claim 1 wherein A is —CH 2 — and C is —O—.

18. The compound of claim 17 wherein:

n represents 2 or 3;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent H;

R 4 is selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 is selected from the group consisting of H, SO 3 H, SO 3 L 1 , SO 3 Na, SO 3 K, SO 3 N(C 1-8 alkyl) 4 , fucosyl and methylfucosyl.

19. The compound of claim 18 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

20. The compound of claim 1 , having at least one of the following characteristics:

n=2 or 3;

A is selected from the group consisting of —C(O)— and —CH 2 —;

C represents —O—;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent a hydrogen atom;

R 4 represents a substituent selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ;

R 8 represents a substituent selected from the group consisting of H, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO 3 H, SO 3 L 1 , SO 3 Na, SO 3 K and SO 3 N(C 1-8 alkyl) 4 .

21. The compound of claim 1 wherein:

n=2 or 3;

A is selected from the group consisting of —C(O)— and —CH 2 —;

C represents —O—;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 7 and R 9 represent a hydrogen atom;

R 4 represents a substituent selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 represents a substituent selected from the group consisting of H, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K and SO 3 N(C 1-8 -alkyl) 4 .

22. The compound of claim 1 wherein R 8 is selected from the group consisting of H, SO 3 H, SO 3 Li, SO 3 Na, SO 3 K, SO 3 N(C 1-8 -alkyl) 4 and a substituent of formula:

wherein

R 26 K represents a substituent selected from the group consisting of H and CH 3 ; and

R 27 and R 28 represent, independently of each other, a substituent selected from the group consisting of H, C(O)CH 3 , SO 3 H, SO 3 Li, SO 3 Na, SO 3 K and SO 3 N(C 1-8 -alkyl) 4 .

23. The compound of claim 22 wherein R 26 , R 27 and R 28 each represents a hydrogen atom.

24. The compound of claim 1 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 7 to 15 carbon atoms.

25. The compound as claimed in claim 1 , for which D represents a hydrocarbon-based chain according to one of the formulae represented below

wherein

m=1 to 12

p=0 to 11

q=6 to 14

s=5 to 13

with m+p≧12 and m+p≧4.

26. The compound of claim 1 wherein D represents a hydrocarbon-based chain according to one of the formulae represented below

in which

m=1 to 12

p=0 toll

q=6 to 14

with m+p≦12 and m+p≧4.

27. The compound of claim 1 wherein D represents a linear hydrocarbon-based chain comprising 11 carbon atoms that is saturated, or unsaturated between carbon atoms 4 and 5.

28. The compound of claim 1 used as a nodulation factor for a plant.

29. The nodulation factor of claim 28 wherein said plant is a legume.

30. The nodulation factor of claim 29 wherein said legume is soybean, pea, horse bean, groundnut, bean, lupin, alfalfa or clover.

31. The compound of claim 1 used as a plant growth stimulation factor.

32. A process for treating seeds, comprising applying thereto, alone or in combination with other active molecules, one or more compound(s) as defined in claim 1 .