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Paramétrages

Paramétrages

1. WO2005063784 - COMPOSES SYNTHETIQUES UTILES COMME AGENTS DE NODULATION DES LEGUMINEUSES ET PROCEDES DE PREPARATION DE CES COMPOSES

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

Claims:

A compound of formula (I)


in which

► n represents 1 , 2 or 3;

► A represents a substituent chosen from -C(O)-, -C(S)-, -CH2-, -CHR10-, -CR10R11-,

-C(O)O-, -C(O)S-, -C(S)O-, -C(S)S-, -C(O)NH-, -C(NH)NH- and -C(S)NH-;

► B represents

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

∙ a naphthylene;

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from 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 chosen from nitrogen, oxygen and sulfur;

∙ a biphenylene;

∙ or a heterobiphenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2,

N3, OR14, SR14, NR15R16 and C1-6-alkyl;

► C represents a substituent chosen from -O-, -S-, -CH2-, -CHR17-, -CR17R18-, -NH- and

-NR19;

► 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 chosen from H, OH, OR20, NH2 and NHR20;

► R1 represents a substituent chosen from H, C1-6-alkyl, C(O)H and C(O)CH3;

► R2, R3, R6, R14, R15, R16 and R19 represent, independently of each other, a substituent chosen from H, C1-6-alkyl, C(O)01-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2,

-C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl and -C(NH)NHC1-6-alkyl;

► R4 represents a substituent chosen from H, C1-6-alkyl and R21;

► R5 represents a substituent chosen from H, C1-6-alkyl, fucosyl and R22;

► R7 represents a substituent chosen from H, C1-6-alkyl, arabinosyl and R23;

► R8 represents a substituent chosen from H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 and R24;

► R9 represents a substituent chosen from H, C1-6-alkyl, mannose, glycerol and R25;

► R10, R11, R17 and R18 represent, independently of each other, a substituent chosen from C1-6-alkyl and F;

► R20, R21, R22, R23, R24 and R25 represent, independently of each other, a substituent chosen from C(O)C1-6-alkyl, -C(S)C1-6-alkyl, - C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl and -C(NH)NHC1-6-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, which are agriculturally acceptable, such as lithium, sodium, potassium and tetraalkylammonium salts.

2. The compound of formula (I) as claimed in claim 1, having one or other of the following characteristics, taken separately or in combination:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► 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)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

3. The compound of formula (I) as claimed in claim 1 or 2, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► E and G represent NHC(O)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

4. The compound of formula (I) as claimed in any one of claims 1 to 3, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

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

► E and G represent NHC(O)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

5. The compound of formula (I) as claimed in any one of claims 1 to 4, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► 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)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

6. The compound of formula (I) as claimed in any one of claims 1 to 5, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► 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)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

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


in which

► n represents 1 , 2 or 3,

► B represents

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

∙ a naphthylene;

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from 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 chosen from nitrogen, oxygen and sulfur;

∙ a biphenylene;

∙ or a heterobiphenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2,

N3, OR14, SR14, NR15R16 and C1-6-alkyl;

► C represents a substituent chosen from -O-, -S-, -CH2- -CHR17-, -CR17R18-, -NH- or -NR19;

► 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 chosen from H, OH, OR20, NH2, NHR20;

► R1 represents a substituent chosen from H, C1-6-alkyl, C(O)H, and C(O)CH3;

R2, R3, and R6 represent, independently of each other, a substituent chosen from H, C1-6-alkyl, C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHCr6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R4 represents a substituent chosen from H, C1-6-alkyl or R21;

► R5 represents a substituent chosen from H, C1-6-alkyl, fucosyl or R22;

► R7 represents a substituent chosen from H, C1-6-alkyl, arabinosyl or R23;

► R8 represents a substituent chosen from H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 or R24;

► R9 represents a substituent chosen from H, C1-6-alkyl, mannose, glycerol or R25;

► R10, R11, R17 and R18 represent, independently of each other, a substituent chosen from C1-6-alkyl or F;

► R14, R15, R16 and R19 represent, independently of each other, a substituent chosen from

H or C1-6-alkyl, -C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHCrB-alkyl or -C(NH)NHC1-6-alkyl;

► R20, R21, R22, R23, R24 and R25 represent, independently of each other, a substituent chosen from C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-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, which are agriculturally acceptable. Among the compounds defined above, the most important compounds are the salts, more particularly the lithium, sodium, potassium or tetraalkylammonium salts.

8. The compound of formula (Ia) as claimed in claim 7, having one or other of the following characteristics, taken separately or in combination:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

9. The compound of formula (Ia) as claimed in claim 7 or 8, simultaneously having the following characteristics:

► n represents 2 or 3;

► E and G represent NHC(O)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

10. The compound of formula (Ia) as claimed in any one of claims 7 to 9, simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

11. The compound of formula (Ia) as claimed in any one of claims 7 to 10, simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

12. The compound of formula (Ia) as claimed in any one of claims 7 to 11, simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

13. The compound as claimed in claim 1 and of formula (Ib)


in which

► n represents 1, 2 or 3,

► B represents

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

∙ a naphthylene;

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from 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 chosen from nitrogen, oxygen and sulfur;

∙ a biphenylene;

∙ or a heterobiphenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR1SR16, CF3, OCF3, -NO2, N3, OR14, SR14, NR15R16 and C1-6-alkyl;

► C represents a substituent chosen from -O-, -S-, -CH2-, -CHR17-, -CR17R18-, -NH- or -NR19;

► 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 chosen from H, OH, OR20, NH2, NHR20;

► R1 represents a substituent chosen from H, C1-6-alkyl, C(O)H, and C(O)CH3;

► R2, R3, and R6 represent, independently of each other, a substituent chosen from H, C1-6-alkyl, C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R4 represents a substituent chosen from H, C1-6-alkyl or R21;

► R5 represents a substituent chosen from H, C1-6-alkyl, fucosyl or R22;

► R7 represents a substituent chosen from H, C1-6-alkyl, arabinosyl or R23;

► R8 represents a substituent chosen from H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 or R24;

► R9 represents a substituent chosen from H, C1-6-alkyl, mannose, glycerol or R25;

► R10, R11, R17 and R18 represent, independently of each other, a substituent chosen from C1-6-alkyl or F;

► R14, R15, R16 and R19 represent, independently of each other, a substituent chosen from H or C1-6-alkyl, -C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R20, R21, R22, R23, R24 and R25 represent, independently of each other, a substituent chosen from C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2,

-C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-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, which are agriculturally acceptable. Among the compounds defined above, the most important compounds are the salts, more particularly the lithium, sodium, potassium or tetraalkylammonium salts.

14. The compound of formula (Ib) as claimed in claim 13, having one or other of the following characteristics, taken separately or in combination:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

15. The compound of formula (Ib) as claimed in claim 13 or 14, simultaneously having the following characteristics:

► n represents 2 or 3;

► E and G represent NHC(O)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

16. The compound of formula (Ib) as claimed in any one of claims 13 to 15 simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

17. The compound of formula (Ib) as claimed in any one of claims 13 to 16 simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

18. The compound of formula (Ib) as claimed in any one of claims 13 to 17 simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or 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 chosen from -C(O)-, -C(S)-, -CH2-, -CHR10-, -CR10R11-, -C(O)O-, -C(O)S-, -C(S)O-, -C(S)S-, -C(O)NH-, -C(NH)NH- or -C(S)NH-;

► B represents

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

∙ a naphthylene;

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from 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 chosen from nitrogen, oxygen and sulfur;

∙ a biphenylene;

∙ or a heterobiphenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R18, CF3, OCF3, -NO2,

N3, OR14, SR14, NR15R16 and C1-6-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 chosen from H, OH, OR20, NH2, NHR20;

► R1 represents a substituent chosen from H, C1-6-alkyl, C(O)H, and C(O)CH3;

► R2, R3, and R6 represent, independently of each other, a substituent chosen from H, C1-6-alkyl, C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R4 represents a substituent chosen from H, C1-6-alkyl or R21;

► R5 represents a substituent chosen from H, C1-6-alkyl, fucosyl or R22;

► R7 represents a substituent chosen from H, C1-6-alkyl, arabinosyl or R23;

► R8 represents a substituent chosen from H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 or R24; ► R9 represents a substituent chosen from H, C1-6-alkyl, mannose, glycerol or R25;

► R10, R11, R17 and R18 represent, independently of each other, a substituent chosen from C1-6-alkyl or F;

► R14, R15, R16 and R19 represent, independently of each other, a substituent chosen from H or C1-6-alkyl, -C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R20, R21, R22, R23, R24 and R25 represent, independently of each other, a substituent chosen from C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2,

-C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-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, which are agriculturally acceptable. Among the compounds defined above, the most important compounds are the salts, more particularly the lithium, sodium, potassium or tetraalkylammonium salts.

20. The compound of formula (Ic) as claimed in claim 19, having one or other of the following characteristics, taken separately or in combination:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► 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)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

21. The compound of formula (Ic) as claimed in claim 19 or 20, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► E and G represent NHC(O)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

22. The compound of formula (Ic) as claimed in any one of claims 19 to 21, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

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

► E and G represent NHC(O)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

23. The compound of formula (Ic) as claimed in any one of claims 19 to 22, simultaneously having the following characteristics:

► n represents 2 or 3;

► A represents -C(O)- or -CH2-;

► 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)CH3;

► R1 represents H, CH3 or C(O)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

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


in which

► n represents 1 , 2 or 3;

► B represents

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

∙ a naphthylene;

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from 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 chosen from nitrogen, oxygen and sulfur;

∙ a biphenylene;

∙ or a heterobiphenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2,

N3, OR14, SR14, NR15R16 and C1-6-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 chosen from H, OH, OR20, NH2, NHR20;

► R1 represents a substituent chosen from H, C1-6-alkyl, C(O)H, and C(O)CH3;

► R2, R3, and R6 represent, independently of each other, a substituent chosen from H, C1-6-alkyl, C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R4 represents a substituent chosen from H, C1-6-alkyl or R21;

► R5 represents a substituent chosen from H, C1-6-alkyl, fucosyl or R22;

► R7 represents a substituent chosen from H, C1-6-alkyl, arabinosyl or R23;

► R8 represents a substituent chosen from H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 or R24; ► R9 represents a substituent chosen from H, C1-6-alkyl, mannose, glycerol or R25;

► R10, R11, R17 and R18 represent, independently of each other, a substituent chosen from C1-6-alkyl or F;

► R14, R15, R16 and R19 represent, independently of each other, a substituent chosen from H or C1-6-alkyl, -C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R20, R21, R22, R23, R24 and R25 represent, independently of each other, a substituent chosen from C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-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, which are agriculturally acceptable. Among the compounds defined above, the most important compounds are the salts, more particularly the lithium, sodium, potassium or tetraalkylammonium salts.

25. The compound of formula (Id) as claimed in claim 24, having one or other of the following characteristics, taken separately or in combination:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

26. The compound of formula (Id) as claimed in claim 24 or 25, simultaneously having the following characteristics:

► n represents 2 or 3;

► E and G represent NHC(O)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

27. The compound of formula (Id) as claimed in any one of claims 24 to 26, simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

28. The compound of formula (Id) as claimed in any one of claims 24 to 27, simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

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


(Ie)

in which

► n represents 1, 2 or 3;

► B represents

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

∙ a naphthylene;

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from 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 chosen from nitrogen, oxygen and sulfur;

∙ a biphenylene;

∙ or a heterobiphenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2, N3, OR14, SR14, NR15R16 and C1-6-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 chosen from H, OH, OR20, NH2, NHR20;

► R1 represents a substituent chosen from H, C1-6-alkyl, C(O)H, and C(O)CH3;

► R2, R3, and R6 represent, independently of each other, a substituent chosen from H, C1-6-alkyl, C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R4 represents a substituent chosen from H, C1-6-alkyl or R21;

► R5 represents a substituent chosen from H, C1-6-alkyl, fucosyl or R22;

► R7 represents a substituent chosen from H, C1-6-alkyl, arabinosyl or R23;

► R8 represents a substituent chosen from H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 or R24;

► R9 represents a substituent chosen from H, C1-6-alkyl, mannose, glycerol or R25;

► R10, R11, R17 and R18 represent, independently of each other, a substituent chosen from C1-6-alkyl or F;

► R14, R15, R16 and R19 represent, independently of each other, a substituent chosen from H or C1-6-alkyl, -C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2, -C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-alkyl;

► R20, R21, R22, R23, R24 and R25 represent, independently of each other, a substituent chosen from C(O)C1-6-alkyl, -C(S)C1-6-alkyl, -C(O)OC1-6-alkyl, -C(O)NH2, -C(S)NH2,

-C(NH)NH2, -C(O)NHC1-6-alkyl, -C(S)NHC1-6-alkyl or -C(NH)NHC1-6-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, which are agriculturally acceptable. Among the compounds defined above, the most important compounds are the salts, more particularly the lithium, sodium, potassium or tetraalkylammonium salts.

30. The compound of formula (Ie) as claimed in claim 29, having one or other of the following characteristics, taken separately or in combination:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

31. The compound of formula (Ie) as claimed in claim 29 or 30, simultaneously having the following characteristics:

► n represents 2 or 3;

► E and G represent NHC(O)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methyl- fucosyl.

32. The compound of formula (Ie) as claimed in any one of claims 29 to 31 , simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► Ra represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

33. The compound of formula (Ie) as claimed in any one of claims 29 to 32, simultaneously having the following characteristics:

► 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)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, R7 and R9 represent H;

► R4 represents H, C(O)CH3 or C(O)NH2;

► R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4, fucosyl or methylfucosyl.

34. The compound as claimed in any one of claims 1 to 33, for which

► B represents

∙ a naphthylene;

∙ an arylene;

∙ a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur; or

∙ a heteronaphthylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2, N3, OR14, SR14, NR15R16 and C1-6-alkyl.

35. The compound as claimed in any one of claims 1 to 34, for which

► B represents

∙ an arylene;

∙ or a heteroarylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2, N3, OR14, SR14, NR15R16 and C1-6-alkyl.

36. The compound as claimed in any one of claims 1 to 35, for which

► B represents

∙ a phenylene;

∙ or a heterophenylene comprising 1 or 2 hetero atoms chosen from nitrogen, oxygen and sulfur;

these groups possibly being substituted with one or two substituents R12 and R13 chosen, independently of each other, from halogen, CN, C(O)OR14, C(O)NR15R16, CF3, OCF3, -NO2, N3, OR14, SR14, NR15R16 and C1-6-alkyl.

37. The compound as claimed in any one of claims 1 to 33, for which

► B represents a substituent chosen from:

in which R12 and R13 represent two substituents chosen, independently of each other, from halogen, CN, CF3, OCF3, -NOz, N3, OR14, SR14, NR15R16 and C1-6-alkyl.

38. The compound as claimed in claim 37, for which B represents a phenylene B1 that may be substituted with one or two substituents R ι12 13

and R chosen, independently of each other, from halogen, CN, CF3, OCF3, -NO2, N3, OR14, SR14, NR15R16 and C1-6-alkyl.

39. The compound as claimed in one of the preceding claims, having one of the following characteristics, taken separately or in combination:

► n = 2 or 3;

► A represents -C(O)- or -CH2-;

► C represents -O-;

► E and G represent NHC(O)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, and R7 represent a hydrogen atom;

► R4 represents a substituent chosen from H, C(O)CH3 and C(O)NH2;

► R8 represents a substituent chosen from H, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K and SO3N(C1-8alkyl)4;

► R9 represents a hydrogen atom.

40. The compound as claimed in one of the preceding claims, having all of the following characteristics:

► n = 2 or 3;

► A represents -C(O)- or -CH2-;

► C represents -O-;

► E and G represent NHC(O)CH3;

► R1 represents H or C(O)CH3;

► R2, R3, R5, R6, and R7 represent a hydrogen atom;

► R4 represents a substituent chosen from H, C(O)CH3 or C(O)NH2;

► R8 represents a substituent chosen from H, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3Li, SO3Na, SO3K or SO3N(C1-8alkyl)4;

► R9 represents a hydrogen atom.

41. The compound as claimed in one of the preceding claims, for which R8 represents H, SO3H, SO3Li, SO3Na, SO3K, SO3N(C1-8alkyl)4 or a substituent of formula:


in which

► R26 represents a substituent chosen from H and CH3;

► R27 and R28 represent, independently of each other, a substituent chosen from H, C(O)CH3, SO3H, SO3Li, SO3Na, SO3K and SO3N(C1-8alkyl)4.

42. The compound as claimed in claim 41, for which R26, R27 and R28 represent a hydrogen atom.

43. The compound as claimed in one of the preceding claims, for which D represents a linear, saturated or unsaturated hydrocarbon-based chain containing from 7 to 15 carbon atoms.

44. The compound as claimed in one of the preceding claims, for which 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

► s = 5 to 13

with m+p≤ 12 and m+p≥ 4.

45. The compound as claimed in one of the preceding claims, for which 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;

46. The compound as claimed in one of the preceding claims, for which D represents a linear hydrocarbon-based chain containing 11 carbon atoms, which is saturated, or unsaturated between carbon atoms 4 and 5.

47. The compound as claimed in one of the preceding claims, corresponding to one of the following formulae:

+

in which, when it is present, M represents a cation chosen from H , Li+ , Na+, K+ and (C1-8alkyl)4N+.

48. The use of a compound as claimed in any one of claims 1 to 47, as a nodulation factor for a plant.

49. The use as claimed in claim 48, characterized in that said plant is a legume.

50. The use as claimed in claim 49, characterized in that said legume is soybean, pea, horse bean, groundnut, bean, lupin, alfalfa or clover.

51. The use of a compound as claimed in any one of claims 1 to 47, as a plant growth stimulation factor

52. A process for treating seeds, comprising the application, alone or as a combination with other active molecules, of one or more compound(s) as defined in any one of claims 1 to 47.