Substituted thiophene carboxamides and derivatives thereof as microbicides

1 . A compound of formula (I):

wherein

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

R 3 is methyl;

R 4 and R 5 are selected independently from one another from the group consisting of hydrogen, halogen, cyano, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, —O—C(═O)—C 1 -C 6 -alkyl, C 3 -C 6 -carbocycle, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C(═O)—NH 2 , —C(═O)—NH(C 1 -C 6 -alkyl), —C(═O)—N(C 1 -C 6 -alkyl) 2 , —C(═O)—OH, —C(═O)—O—C 1 -C 6 -alkyl, aryl, 5- to 9-membered heteroaryl, —C 1 -C 6 -alkyl-C 1 -C 6 -alkoxy, —C 1 -C 6 -alkyl-C 1 -C 6 -haloalkyl, —C 1 -C 6 -alkyl-C 3 -C 6 -carbocycle, —C 1 -C 6 -alkyl-4-, 5- or 6-membered non-aromatic heterocyclyl, —C 1 -C 6 -alkyl-aryl, —C 1 -C 6 -alkyl-hydroxyaryl, —C 1 -C 6 -alkyl-5- to 9-membered heteroaryl, —C 1 -C 6 -alkyl-S—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-S—C(═O)—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-O—(C═O)—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-C(═O)—NH 2 , —C 1 -C 6 -alkyl-C(═O)—NH(C 1 -C 6 -alkyl), —C 1 -C 6 -alkyl-C(═O)—N(C 1 -C 6 -alkyl) 2 , —C 1 -C 6 -alkyl-C(═O)—OH, —C 1 -C 6 -alkyl-C(═O)—O—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-NH—C(═NH)—NH 2 , —S—C 1 -C 6 -alkyl, —S—C(═O)—C 1 -C 6 -alkyl, —S—C(═O)—O—C 1 -C 6 -alkyl, —S—C(═S)—O—C 1 -C 6 -alkyl, —S—C(═O)—S—C 1 -C 6 -alkyl, —S—C(═O)—NH 2 , —S—C(═O)—NH(C 1 -C 6 -alkyl), —S—C(═O)—NH(C 1 -C 6 -alkyl) 2 , —S—C(═S)—NH 2 , —S—C(═S)—NH(C 1 -C 6 -alkyl), —S—C(═S)—NH(C 1 -C 6 -alkyl) 2 , —C 1 -C 6 -alkyl-S—C(═O)—O—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-S—C(═O)—S—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-S—C(═O)—NH 2 , —C 1 -C 6 -alkyl-S—C(═O)—NH(C 1 -C 6 -alkyl), —C 1 -C 6 -alkyl-S—C(═O)—NH(C 1 -C 6 -alkyl) 2 , —C 1 -C 6 -alkyl-S—C(═S)—NH 2 , —C 1 -C 6 -alkyl-S—C(═S)—NH(C 1 -C 6 -alkyl), and —C 1 -C 6 -alkyl-S—C(═S)—NH(C 1 -C 6 -alkyl) 2 , wherein acyclic R 4 and R 5 radicals may be substituted with one or more R w substituents, wherein cyclic R 4 and R 5 radicals may be substituted with one or more R x substituents, wherein at least one of R 4 and R 5 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -carbocycle, or

R 4 and R 5 form, together with the carbon atom to which they are attached, a carbonyl, a thiocarbonyl, a C 3 -C 6 -carbocycle, or a 3- to 6-membered heterocycle, wherein said C 3 -C 6 -carbocycle and 3- to 6-membered heterocycle may be substituted with one or more R x substituents;

each R w is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6 -sulfanyl, formyl, carbamoyl, carbamate, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbamoyl, di-C 1 -C 8 -alkylcarbamoyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyloxy, C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfinyl, C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfonylamino, C 1 -C 8 -halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, C 1 -C 8 -alkylsulfamoyl, and di-C 1 -C 8 -alkylsulfamoyl;

each R x is independently selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ 6 -sulfanyl, formyl, carbamoyl, carbamate, C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbamoyl, di-C 1 -C 8 -alkylcarbamoyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyloxy, C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfinyl, C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfonylamino, C 1 -C 8 -halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, C 1 -C 8 -alkylsulfamoyl, and di-C 1 -C 8 -alkylsulfamoyl;

R 6 and R 7 are independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -carbocycle, or

R 6 and R 7 form, together with the carbon atom to which they are attached, a C 3 -C 6 -carbocycle or a 3- to 6-membered heterocycle;

n is 0 or 1;

W is oxygen or sulfur;

Y is NR 8 , wherein R 8 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -cyanoalkyl, hydroxy, C 1 -C 6 -alkoxy or C 3 -C 6 -carbocycle;

Z is selected from the group consisting of cyano, —C(═O)—OR a , —C(═O)—SR a , —C(═O)—NR b R c , —C(═S)—NR b R c , and —C(═O)—NH—CR d R e —C(═O)—OR a ;

R a is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C 1 -C 6 -alkyl-Si(C 1 -C 6 -alkyl) 3, —C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, 5- to 9-membered heteroaryl, and —C 1 -C 6 -alkyl-5- to 9-membered heteroaryl, or

R a forms, together with R 4 and with the atoms to which they are attached, a 4- to 7-membered heterocycle;

R b and R c are independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, hydroxyl, C 1 -C 6 -alkoxy, cyano, and C 1 -C 6 -cyanoalkyl, or

R b forms, together with R 4 and with the atoms to which they are attached, a 4- to 7-membered heterocycle;

R d and R e are independently selected from the group consisting of hydrogen, cyano, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, —O—C(═O)—C 1 -C 6 -alkyl, C 3 -C 6 -carbocycle, —C(═O)—NH 2 , —C(═O)—NH(C 1 -C 6 -alkyl), —C(═O)—N(C 1 -C 6 -alkyl) 2 , —C(═O)—OH, —C(═O)—O—C 1 -C 6 -alkyl, aryl, 5- to 9-membered heteroaryl, —C 1 -C 6 -alkyl-C 1 -C 6 -alkoxy, —C 1 -C 6 -alkyl-C 3 -C 6 -carbocycle, —C 1 -C 6 -alkyl-aryl, —C 1 -C 6 -alkyl-hydroxyaryl, —C 1 -C 6 -alkyl-5- to 9-membered heteroaryl, —C 1 -C 6 -alkyl-S—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-S—C(═O)—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-O—(C═O)—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-C(═O)—NH 2 , —C 1 -C 6 -alkyl-C(═O)—NH(C 1 -C 6 -alkyl), —C 1 -C 6 -alkyl-C(═O)—N(C 1 -C 6 -alkyl) 2 , —C 1 -C 6 -alkyl-C(═O)—OH, —C 1 -C 6 -alkyl-C(═O)—O—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-NH—C(═NH)—NH 2 , wherein at least one of R d and R e is hydrogen, C 1 -C 6 -alkyl, or C 3 -C 6 -carbocycle, or

R d and R e form, together with the carbon atom to which they are attached, a carbonyl, C 3 -C 6 -carbocycle, or a 3- to 6-membered heterocycle;

wherein if W is oxygen, Y is NH, n=0, and R 4 is hydrogen, C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-aryl, —C 1 -C 6 -alkyl-hydroxyaryl, or —C 1 -C 6 -alkyl-S—C 1 -C 6 -alkyl, and R 5 is hydrogen, or R 4 and R 5 form together with the carbon atom to which they are attached a cyclopropyl, then Z is selected from the group consisting of cyano, —C(═O)—SR a , —C(═O)—NR b R c , —C(═S)—NR b R c , and —C(═O)—NH—CR d R e —C(═O)—OR a ;

provided that the compound is not

ethyl {[(4,5-dibromo-3-methyl-2-thienyl) carbonyl]amino}(phenyl) acetate or

ethyl {[(4,5-dichloro-3-methyl-2-thienyl) carbonyl]amino}(phenyl) acetate.

2 . The compound according to claim 1 , wherein

R 1 and R 2 are chlorine; and

R 3 is methyl.

3 . The compound according to claim 1 , wherein

R 1 and R 2 are bromine; and

R 3 is methyl.

4 . The compound of claim 1 , wherein

R 4 and R 5 are independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 3 -C 6 -carbocycle, aryl, —C 1 -C 6 -alkyl-C 1 -C 6 -alkoxy, —C 1 -C 6 -alkyl-C 3 -C 6 -carbocycle, C 1 -C 6 -alkyl-O—(C═O)—C 1 -C 6 -alkyl, —C 1 -C 6 -alkyl-C(—O)—OH; —C 1 -C 6 -alkyl-aryl, and —C 1 -C 6 -alkyl-S—C 1 -C 6 -alkyl, wherein acyclic R 4 and R 5 radicals may be substituted with one or more R w substituents, cyclic R 4 and R 5 radicals may be substituted with one or more R x substituents, and at least one of R 4 and R 5 is hydrogen, C 1 -C 6 -alkyl, or C 3 -C 6 -carbocycle, or R 4 and R 5 form, together with the carbon atom to which they are attached, a C 3 -C 6 -carbocycle or a 3- to 6-membered heterocycle, wherein said C 3 -C 6 -carbocycle and 3- to 6-membered heterocycle may be substituted with one or more R x substituents.

5 . The compound of claim 1 , wherein W is oxygen.

6 . The compound of claim 1 , wherein Y is NR 8 , wherein R 8 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -cyanoalkyl, hydroxy, C 1 -C 6 -alkoxy, or C 3 -C 6 -carbocycle.

7 . The compound of claim 1 , wherein Z is selected from the group consisting of cyano, —C(═O)—SR a , —C(═O)—NR b R c , —C(═S)—NR b R c , and —C(═O)—NH—CR d R e —C(═O)—OR a .

8 . A composition comprising at least one compound of claim 1 , and at least one agriculturally suitable auxiliary.

9 . A method for controlling bacterial and/or fungal diseases in plants comprising the step of applying at least one compound of claim 1 to a plant, plant part, seed, fruit, or soil in which a plant grows.

10 . The compound of claim 1 , wherein R 8 is hydrogen.

11 . The compound of claim 1 , wherein Z is C(═O)—OR a .

12 . A method for controlling bacterial and/or fungal diseases in plants comprising the step of applying a composition according to claim 8 to a plant, plant part, seed, fruit, or soil in which a plant grows.