Substituted thiophenecarboxamides and analogues as antibacterials agents

1. A compound of formula (III):

wherein

R 2 and R 2 are identical and are a bromine atom or a chlorine atom;

R 3 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a methyl.

2. The compound of formula (III) according to claim 1 wherein R 3 is a fluorine atom, a chlorine atom or a methyl.

3. The compound of formula (III) according to claim 1 wherein R 3 is different from R 1 and R 2 .

4. A composition comprising at least one compound of formula (III) according to claim 1 and at least one agriculturally suitable auxiliary.

5. A method for controlling bacterial diseases comprising the step of applying (i) at least one compound of formula (III) according to claim 1 , or (ii) a composition comprising at least one compound of formula (III) according to claim 1 and at least one agriculturally suitable auxiliary to plants, plant parts, seeds, fruits or to the soil in which the plants grow.

6. A process for preparing a compound of formula (III) according to claim 1 comprising the step of performing the cyclization of a compound of formula (XXI) or a salt thereof to provide a compound of formula (III):

wherein R 4 is a hydrogen atom;

R 1 , R 2 and R 3 as recited in claim 1 .

7. The process according to claim 6 further comprising the steps of:

(a) reacting a compound of formula (XXII) with a compound of formula (XXIII) or a salt thereof:

wherein

R 1 , R 2 and R 3 are as recited in claim 6 ;

R 4 is a hydrogen atom or C 1 -C 6 -alkyl; and

U 1 is a halogen atom, a hydroxy group or a C 1 -C 6 -alkoxy group;

to provide a compound of formula (XXI) as recited in claim 6 when R 4 is a hydrogen atom;

(b) performing an hydrolysis of the compound obtained in step (a) when R 4 is a C 1 -C 6 -alkyl to provide a compound of formula (XXI) as recited in claim 6 .

8. The process according to claim 6 further comprising the step(s) of:

(a) performing a diazotation of a compound of formula (XXIV) followed by an aromatic substitution:

wherein

R 1 , R 2 and R 3 are as recited in claim 6 ;

R 4 is a hydrogen atom or C 1 -C 6 -alkyl; and

U 19 is an amino group, a chlorine atom or a bromine atom and U 20 is an amino group, a chlorine atom or a bromine atom;

provided that at least one of U 19 or U 20 is an amino group;

to provide a compound of formula (XXI) as recited in claim 6 when R 4 is a hydrogen atom;

(b) performing a hydrolysis of the compound obtained in step (a) when R 4 is a C 1 -C 6 -alkyl to provide a compound of formula (XXI) as recited in claim 6 .

9. The process according to claim 8 further comprising the step of reacting a compound of formula (XXVI):

wherein

U 19 is an amino group, a chlorine atom or a bromine atom and U ° is an amino group, a chlorine atom or a bromine atom;

provided that at least one of U 19 or U 20 is an amino group; and

R 3 as recited in claim 6 ,

with a compound of formula (XXIII)

wherein

R 4 is a hydrogen atom or C 1 -C 6 -alkyl,

to provide a compound of formula (XXIV).

10. The process according to claim 6 further comprising the steps of performing a fluorination of a compound of formula (XXXV):

wherein

R 1 and R 2 are as recited in claim 6 ; and

R 4 is a hydrogen atom or a C 1 -C 6 -alkyl;

to provide a compound of formula (XXI).

11. A compound of formula (XXI):

wherein

R 1 and R 2 are identical and are a bromine atom or a chlorine atom;

R 3 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a methyl; and

R 4 is a hydrogen atom or a C 1 -C 6 -alkyl.

12. A compound of formula (XXIIa):

wherein

R 1 and R 2 are identical and are a bromine atom or a chlorine atom;

R 3 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a methyl; and

U 1a is a hydroxy group or a C 1 -C 6 -alkoxy group;

provided that R 3 is not a chlorine atom when R 1 and R 2 are chlorine atoms; and

provided that the compound of formula (XXIIa) does not represent:

methyl 4,5-dichloro-3-fluorothiophene-2-carboxylate [2166596-88-7],

4,5-dichloro-3-fluorothiophene-2-carboxylic acid [2166596-87-6],

ethyl 4,5-dibromo-3-fluorothiophene-2-carboxylate [2260624-98-2],

4,5-dibromo-3-fluorothiophene-2-carboxylic acid [1628447-64-2],

methyl 4,5-dibromo-3-chlorothiophene-2-carboxylate [1501789-47-4],

4,5-dibromo-3-iodothiophene-2-carboxylic acid [854626-46-3],

4,5-dibromo-3-chlorothiophene-2-carboxylic acid [503308-99-4],

ethyl 4,5-dibromo-3-chlorothiophene-2-carboxylate [503308-98-3],

methyl 4,5-dibromo-3-fluorothiophene-2-carboxylate [395664-58-1],

tert-butyl 3,4,5-tribromothiophene-2-carboxylate [62224-27-5],

ethyl 3,4,5-tribromothiophene-2-carboxylate [54113-44-9],

3,4,5-tribromothiophene-2-carboxylic acid [53317-05-8],

methyl 3,4,5-tribromothiophene-2-carboxylate [24647-80-1],

ethyl 4,5-dibromo-3-methylthiophene-2-carboxylate [2088257-63-8],

4,5-dichloro-3-methylthiophene-2-carboxylic acid [854626-34-9],

4,5-dibromo-3-methylthiophene-2-carboxylic acid [854626-32-7],

methyl 4,5-dichloro-3-methylthiophene-2-carboxylate [854626-27-0], and

methyl 4,5-dibromo-3-methylthiophene-2-carboxylate [648412-53-7].

13. A compound of formula (XXIVa) or (XXIVb):

wherein

R 1 or R 2 atom or a chlorine atom;

R 3 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a methyl; and

R 4 is a hydrogen atom or a C 1 -C 6 -alkyl.

14. A compound of formula (XXVIa) or (XXVIb):

wherein

R 1 or R 2 is a bromine atom or a chlorine atom;

R 3 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a methyl; and

U 1a is an hydroxy group or a C 1 -C 6 -alkoxy group;

provided that the compound of formula (XXVIa) does not represent:

ethyl 5-amino-4-bromo-3-methylthiophene-2-carboxylate [851443-15-7]; and

provided that the compound of formula (XXVIb) does not represent:

ethyl 4-amino-3,5-dibromothiophene-2-carboxylate [1394375-09-7].

15. A compound of formula (XXXV):

wherein

R 1 and R 2 are identical and are a bromine atom or a chlorine atom;

R 4 is a hydrogen atom or a C 1 -C 6 -alkyl.