Novel method for synthesizing n-alkyl-glycosyl(di)amine derivatives and uses of same against phytopathogens

A method for treating a bacterical or fungal infection comprising administering to a subject in need thereof an effective amount of an N-alkyl-glycosyl(di)amine derivative corresponding to general formula (I) below:

• in which:
• R1 is a glycosyl radical,
• R2 represents a hydrogen atom, a glycosyl radical, or a C1-C22 alkyl radical,
• n is an integer ranging from 0 to 22,
• X represents a halogen atom, an alkyl, alkenyl or alkynyl radical, a hydroxyl group, a carboxyl or carbaldehyde group, an aryl or heteroaryl group, or an —NR3R4 group, in which R3 represents a hydrogen atom or a glycosyl radical, and R4 represents a hydrogen atom or a C1-C12 alkyl radical, with the proviso that n is different from 0 when X is an —NR3R4 group, wherein the bacterical or fungal infection is caused by one or more of the following phytopathogens:
• Agrobacterium tumefaciens, Pectobacterium atrosepticum, Dickeya dianthicola, Fusarium sambucinum, Fusarium roseum and Phytophthora infestans.

A method for treating a bacterical or fungal infection comprising administering to a subject in need thereof an effective amount of a quaternary N-alkyl-glycosyl(di)ammonium salt corresponding to general formula (II) below:

• in which:
• R1 is a glycosyl radical,
• R2 represents a hydrogen atom, a glycosyl radical, or a C1-C22 alkyl radical,
• n is an integer ranging from 0 to 22,
• X represents a halogen atom, an alkyl, alkenyl or alkynyl radical, a hydroxyl group, a carboxyl or carbaldehyde group, an aryl or heteroaryl group, or an -NR3R4 group, in which R3 represents a hydrogen atom or a glycosyl radical, and R4 represents a hydrogen atom or a C1-C12 alkyl radical,
• R5 represents a hydrogen atom or a C1-C22 alkyl radical, and
• Y represents a halide ion, a sulfate ion R6O—SO2—O− or a sulfonate ion R6—SO2—O−, in which R6 is a C1-C12 alkyl radical,
• with the proviso that n is different from 0 when X is an —NR3R4 group, wherein the bacterical or fungal infection is caused by phytopathogens.

A method for treating a bacterical or fungal infection comprising administering to a subject in need thereof an effective amount of an N-alkyl-glycamine derivative corresponding to general formula (III) below:

• in which:
• n is an integer ranging from 0 to 22,
• X represents a halogen atom, an alkyl, alkenyl or alkynyl radical, a hydroxyl group, a carboxyl or carbaldehyde group, an aryl or heteroaryl group, or an —NR3R4 group, in which R3 represents a hydrogen atom or a glycosyl radical, and R4 represents a hydrogen atom or a C1-C12 alkyl radical,
• R7 represents a hydrogen atom or an —OH or —NH2 group, and
• R8 represents a hydrogen atom or a —CH(OR9)R10 group in which R9 represents a hydrogen atom or a glycosyl radical, and R10 represents a hydrogen atom, or a —CH2OH or —CH(OH)R11 group in which R11 represents a —CH2OH group or a C1-C4 alkyl radical,
• wherein the bacterical or fungal infection is caused by one or more of the following phytopathogens:
• Agrobacterium tumefaciens, Pectobacterium atrosepticum, Dickeya dianthicola, Fusarium sambucinum, Fusarium roseum and Phytophthora infestans.