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 heteroarylene comprising 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur;

a heteronaphthylene comprising 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur;

a divalent radical derived from 2 fused aromatic rings containing 5 or 6 atoms each;

a divalent radical derived from 2 fused aromatic or heteroaromatic rings containing 5 or 6 atoms each and comprising 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur;

these groups 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 L 1 , 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′ is selected from the group consisting of H, CH 3 and C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , R 2 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.

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 3 wherein C represents —O—.

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

6. The compound of claim 5 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 L 1 , SO 3 Na, SO 3 K, SO 3 N(C 1-8 alkyl) 4 , fucosyl and methylfucosyl.

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

8. The compound of claim 7 wherein C represents —O—.

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

10. The compound of claim 9 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.

11. The compound of claim 10 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

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

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

14. The compound of claim 13 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 L 1 , SO 3 Na, SO 3 K, SO 3 N(C 1-8 alkyl) 4 , fucosyl and methylfucosyl.

15. The compound of claim 14 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

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

17. The compound of claim 16 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 L 1 , SO 3 Na, SO 3 K, SO 3 N(C 1-8 alkyl) 4 , fucosyl and methylfucosyl.

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

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

20. The compound of claim 19 wherein:

n represents 2 or 3;

E and G represent NHC(O)CH 3 ;

R 1 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 selected from the group consisting of H, C(O)CH 3 and C(O)NH 2 ; and

R 8 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.

21. The compound of claim 20 wherein D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms.

22. The compound of claim 1 wherein B is selected from the group consisting of

a heteroarylene comprising 1 or 2 hetero atoms selected from the group consisting of from nitrogen, oxygen and sulfur; and

a heteronaphthylene comprising 1 or 2 hetero atoms selected from the group consisting of from nitrogen, oxygen and sulfur;

these groups 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.

23. The compound of claim 1 wherein B represents a heteroarylene comprising 1 or 2 hetero atoms selected from the group consisting of from nitrogen, oxygen and sulfur, optionally 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.

24. The compound of claim 23 wherein the heteroarylene is a heterophenylene.

25. The compound of claim 1 wherein B represents a substituent selected from the group consisting of:

wherein R 12 and R 13 represent two substituents independently selected from the group consisting of halogen, CN, CF 3 , OCF 3 , —NO 2 , N 3 , OR 14 , SR 14 , NR 15 R 16 and C 1-6 -alkyl.

26. 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 Li, SO 3 Na, SO 3 K and SO 3 N(C 1-8 alkyl) 4 .

27. 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 .

28. The compound of claim 1 wherein 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 and a substituent of formula:

wherein

R 26 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 .

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

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

31. 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.

32. 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 to 11

q=6 to 14

with m+p≦12 and m+p≧4.

33. 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.

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

35. The nodulation factor of claim 34 wherein said plant is a legume.

36. The nodulation factor of claim 35 wherein said legume is soybean, pea, horse bean, groundnut, bean, lupin, alfalfa or clover.

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

38. 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 .