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

1. A compound of formula (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 an arylene and a naphthylene, 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, wherein R 14 , R 15 , and R 16 are independently 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;

C represents a substituent selected from the group consisting of —O—, —S—, —CH 2 —, and CH—(C 1-6 -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 , and R 6 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 also the possible geometrical and/or optical isomers, enantiomers and/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 , having at least one of the following characteristics:

n represents 2 or 3;

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

B represents a phenylene;

C represents —O—;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 or C(O)NH 2 ;

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 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.

4. 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 —;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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.

5. 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 —;

C represents —O—;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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.

6. 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 —;

B represents a phenylene;

C represents —O—;

D represents a linear hydrocarbon-based chain containing 11 carbons, which is saturated, or unsaturated between carbons 4 and 5;

E and G represent NHC(O)CH 3 ;

R 1 is selected from the group consisting of H, CH 3 or 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

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.

7. The compound as claimed in claim 1 and of formula (Ia)

in which

n represents 1, 2 or 3,

B is selected from the group consisting of

an arylene

and a naphthylene;

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 , and R 6 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 also the possible geometrical and/or optical isomers, enantiomers and/or diastereoisomers, tautomers, salts, N-oxides, sulfoxides, sulfones, and metal or metalloid complexes thereof.

8. The compound of formula (Ia) of claim 7 , having at least one or other of the following characteristics:

n represents 2 or 3;

B represents a phenylene;

C represents —O—;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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 formula (Ia) 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 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 ;

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.

10. The compound of formula (Ia) of claim 7 wherein:

n represents 2 or 3;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

11. The compound of formula (Ia) of claim 7 wherein:

n represents 2 or 3;

C represents —O—;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

12. The compound of formula (Ia) of claim 7 wherein:

n represents 2 or 3;

B represents a phenylene;

C represents —O—;

D represents a linear hydrocarbon-based chain containing 11 carbons, which is saturated, or unsaturated between carbons 4 and 5;

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 ;

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 as claimed in claim 1 and of formula (Ib)

in which

n represents 1, 2 or 3,

B is selected from the group consisting of

an arylene; and

a naphthylene;

C represents a substituent selected from the group consisting of —O—, —S—, —CH 2 —,and CH—(C 1-6 -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, OCO(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 , and R 6 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 14 , R 15 , R 16 and R 19 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 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 also the possible geometrical and/or optical isomers, enantiomers and/or diastereoisomers, tautomers, salts, N-oxides, sulfoxides, sulfones, and metal or metalloid complexes thereof that are agriculturally acceptable.

14. The compound of formula (Ib) of claim 13 , having at least one of the following characteristics:

n represents 2 or 3;

B represents a phenylene;

C represents —O—;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

15. The compound of formula (Ib) of claim 13 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 ;

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 formula (Ib) of claim 13 wherein:

n represents 2 or 3;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

17. The compound of formula (Ib) of claim 13 wherein:

n represents 2 or 3;

C represents —O—;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

18. The compound of formula (Ib) of claim 13 wherein:

n represents 2 or 3;

B represents a phenylene;

C represents —O—;

D represents a linear hydrocarbon-based chain containing 11 carbons, which is saturated, or unsaturated between carbons 4 and 5;

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 ;

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.

19. The compound as claimed in claim 1 and of formula (Ic)

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

an arylene

and a naphthylene;

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 chosen from H, C 1-6 -alkyl, C(O)H, and C(O)CH 3 ;

R 2 , R 3 , and R 6 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 also the possible geometrical and/or optical isomers, enantiomers and/or diastereoisomers, tautomers, salts, N-oxides, sulfoxides, sulfones, and metal or metalloid complexes thereof that are agriculturally acceptable.

20. The compound of formula (Ic) of claim 19 , having at least one of the following characteristics:

n represents 2 or 3;

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

B represents a phenylene;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

21. The compound of formula (Ic) of claim 19 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 ;

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.

22. The compound of formula (Ic) of claim 19 wherein:

n represents 2 or 3;

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

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

E and G represent NHC(O)CH 3 ;

R l 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 ;

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.

23. The compound of formula (Ic) of claim 19 wherein:

n represents 2 or 3;

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

B represents a phenylene;

D represents a linear hydrocarbon-based chain containing 11 carbons, which is saturated, or unsaturated between carbons 4 and 5;

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 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 ;

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.

24. The compound as claimed in claim 1 and of formula (Id)

in which

n represents 1, 2 or 3;

B is selected from the group consisting of

an arylene

and a naphthylene;

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 , and R 6 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 also the possible geometrical and/or optical isomers, enantiomers and/or diastereoisomers, tautomers, salts, N-oxides, sulfoxides, sulfones, and metal or metalloid complexes thereof, that are agriculturally acceptable.

25. The compound of formula (Id) of claim 24 , having at least one of the following characteristics:

n represents 2 or 3;

B represents a phenylene;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 9 ;

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.

26. The compound of formula (Id) of claim 24 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 ;

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.

27. The compound of formula (Id) of claim 24 wherein:

n represents 2 or 3;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

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 ;

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.

28. The compound of formula (Id) of claim 24 wherein:

n represents 2 or 3;

B represents a phenylene;

D represents a linear hydrocarbon-based chain containing 11 carbons, which is saturated, or unsaturated between carbons 4 and 5;

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 ;

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.

29. The compound of claim 1 and of formula (Ie)

in which

n represents 1, 2 or 3;

B is selected from the group consisting of

an arylene; and

a naphthylene;

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 , and R 6 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 14 , R 15 , R 16 and R 19 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 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 also the possible geometrical and/or optical isomers, enantiomers and/or diastereoisomers, tautomers, salts, N-oxides, sulfoxides, sulfones, and metal or metalloid complexes thereof that are agriculturally acceptable.

30. The compound of formula (Ie) of claim 29 , having at least one of the following characteristics:

n represents 2 or 3;

B represents a phenylene;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

E and G represent NHC(O)CH 3 ;

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

R 8 is selected 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 or methylfucosyl.

31. The compound of formula (Ie) of claim 29 wherein:

n represents 2 or 3;

E and G represent NHC(O)CH 3 ;

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

R 8 is selected 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.

32. The compound of formula (Ie) of claim 29 wherein:

n represents 2 or 3;

D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 3 to 17 carbon atoms;

E and G represent NHC(O)CH 3 ;

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

R 8 is selected 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 or methylfucosyl.

33. The compound of formula (Ie) of claim 29 wherein:

n represents 2 or 3;

B represents a phenylene;

D represents a linear hydrocarbon-based chain containing 11 carbons, which is saturated, or unsaturated between carbons 4 and 5;

E and G represent NHC(O)CH 3 ;

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

R 8 is selected 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.

34. The compound of claim 1 wherein B represents an arylene 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, wherein R 14 , R 15 , and R 16 are independently 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)NHC1-6-alkyl and —C(NH)NHC 1-6 -alkyl.

35. The compound of claim 1 wherein B represents a phenylene 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, wherein R 14 , R 15 , and R 16 are independently 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.

36. The compound as claimed in 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 , and R 7 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 ;

R 9 represents a hydrogen atom.

37. 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 or C(O)CH 3 ;

R 2 , R 3 , R 5 , R 6 , and R 7 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 ; and

R 9 represents a hydrogen atom.

38. 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 represents a substituent selected from the group consisting of H and CH 3 ;

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 and SO 3 N(C 1-8 alkyl) 4 .

39. The compound of claim 38 wherein R 26 , R 27 and R 28 each represents a hydrogen atom.

40. The compound as claimed in claim 1 , for which D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 7 to 15 carbon atoms.

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

D1

D2

D3

D4

D5

D6

in which

m=1 to 12

p=0 to 11

q=6 to 14

s=5 to 13

with m+p≦12 and m+p≧4.

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

D1

D2

D3

in which

m=1 to 12

p=0 to 11

q=6 to 14

with m+p≦12 and m+≧4.

43. 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.

44. The compound of claim 1 , corresponding to one of the following formulae:

in which, when it is present, M represents a cation selected from the consisting of H + , Li + , Na + , K + and (C 1-8 alkyl) 4 N + .

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

46. The nodulation factor of claim 45 wherein said plant is a legume.

47. The nodulation factor of claim 46 wherein said legume is soybean, pea, horse bean, groundnut, bean, lupin, alfalfa or clover.

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

49. The compound of claim 1 wherein B is 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.

50. The compound of claim 49 wherein B is