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US 8,013,132 B2Granted
Synthetic compounds useful as nodulation agents of leguminous plants and preparation processes thereof
AssigneesBayer Aktiengesellschaft, Institute National de la Recherche Agronomique, Centre National De La Recherche Scientifique
InventorsJean-Marie Beau, Jean Denarie, Alfred Grenier, Nathalie Grenouillat, Fabienne Maillet, Boris Vauzeilles
Life of this patent
Estimating the term…
Abstract
The present invention relates to synthetic compounds that are active on plants, especially as legume nodulation factors, and also as plant growth stimulators, and to methods for preparing such compounds, which are of formula (I).
Claims38
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 —CH2—;
- 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)OR14, C(O)NR15R16, CF3, OCF3, —NO2, N3, OR14, SR14, NR15R16 and C1-6-alkyl;
- C represents a substituent selected from the group consisting of —O—, —S—, —CH2—, and CH—(C1-C6-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)CH3 and NHC(O)CH3;
- R1 represents a substituent selected from the group consisting of H, C1-6-alkyl, C(O)H and C(O)CH3;
- R2, R3, R6, R14, R15, and R16 represent, independently of each other, a substituent selected from the group consisting of 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 and —C(NH)NHC1-6-alkyl;
- R4 represents a substituent selected from the group consisting of H, C1-6-alkyl and R21;
- R5 represents a substituent selected from the group consisting of H, C1-6-alkyl, fucosyl and R22;
- R7 represents a substituent selected from the group consisting of H, C1-6-alkyl, arabinosyl and R23;
- R8 represents a substituent selected from the group consisting of H, C1-6-alkyl, fucosyl, methylfucosyl, sulfofucosyl, acetylfucosyl, arabinosyl, SO3H, SO3L1, SO3Na, SO3K, SO3N(C1-8alkyl)4 and R24;
- R9 represents a substituent selected from the group consisting of H, C1-6-alkyl, mannose, glycerol and R25;
- R21, R22, R23, R24 and R25 represent, independently of each other, a substituent selected from the group consisting of 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 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.
19 more elements
Dependencies are inferred from the claim text.