Substituted thiophene carboxamides and derivatives thereof

A method for controlling bacterial diseases on plants or plant parts, comprising administering a compound of formula (I):

• wherein
• R1, R2 and R3 are each chlorine;
• R4 and R5 are selected independently from one another from the group consisting of hydrogen, halogen, cyano, hydroxyl, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkyl, —O—C(═O)—C1-C6-alkyl, C3-C6-carbocycle, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C(═O)—NH2, —C(═O)—NH(C1-C6-alkyl), —C(═O)—N(C1-C6-alkyl)2, —C(═O)—OH, —C(═O)—O—C1-C6-alkyl, aryl, 5- to 9-membered hetero aryl, —C1-C6-alkyl-C1-C6-alkoxy, —C1-C6-alkyl-C1-C6-halo alkyl, —C1-C6-alkyl-C3-C6-carbocycle, —C1-C6-alkyl-4-, 5- or 6-membered non-aromatic heterocyclyl, —C1-C6-alkyl-aryl, —C1-C6-alkyl-hydroxyaryl, —C1-C6-alkyl-5- to 9-membered hetero aryl, —C1-C6-alkyl-S—C1-C6-alkyl, —C1-C6-alkyl-S—C(═O)—C1-C6-alkyl, —C1-C6-alkyl-O—(C═O)—C1-C6-alkyl, —C1-C6-alkyl-C(═O)—NH2, —C1-C6-alkyl-C(═O)—NH(C1-C6-alkyl), —C1-C6-alkyl-C(═O)—N(C1-C6-alkyl)2, —C1-C6-alkyl-C(═O)—OH, —C1-C6-alkyl-C(═O)—O—C1-C6-alkyl, —C1-C6-alkyl-NH—C(═NH)—NH2, —S—C1-C6-alkyl, —S—C(═O)—C1-C6-alkyl, —S—C(═O)—O—C1-C6-alkyl, —S—C(═S)—O—C1-C6-alkyl, —S—C(═O)—S—C1-C6-alkyl, —S—C(═O)—NH2, —S—C(═O)—NH(C1-C6-alkyl), —S—C(═O)—NH(C1-C6-alkyl)2, —S—C(═S)—NH2, —S—C(═S)—NH(C1-C6-alkyl), —S—C(═S)—NH(C1-C6-alkyl)2, —C1-C6-alkyl-S—C(═O)—O—C1-C6-alkyl, —C1-C6-alkyl-S—C(═O)—S—C1-C6-alkyl, —C1-C6-alkyl-S—C(═O)—NH2, —C1-C6-alkyl-S—C(═O)—NH(C1-C6-alkyl), —C1-C6-alkyl-S—C(═O)—NH(C1-C6-alkyl)2, —C1-C6-alkyl-S—C(═S)—NH2, —C1-C6-alkyl-S—C(═S)—NH(C1-C6-alkyl), and —C1-C6-alkyl-S—C(═S)—NH(C1-C6-alkyl)2, wherein cyclic R4 and R5 radicals may be substituted with one or more Rx substituents, wherein at least one of R4 and R5 is hydrogen, C1-C6-alkyl or C3-C6-carbocycle, or R4 and R5 are taken together with the carbon atom to which they are attached to form a C3-C6-carbocycle or a 3- to 6-membered heterocycle, wherein said C3-C6-carbocycle and 3- to 6-membered heterocycle may be substituted with one or more Rx substituents, wherein Rx is independently selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ6-sulfanyl, formyl, carbamoyl, carbamate, C1-C8-alkyl, C3-C7-cycloalkyl, C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C3-C7-halogenocycloalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C1-C8-alkylsulfinyl, C1-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonyl, C1-C8-halogenoalkylsulfonyl having 1 to 5 halogen atoms;
• C1-C8-alkylsulfonylamino, C1-C8-halogenoalkylsulfonylamino having 1 to 5 halogen atoms;
• sulfamoyl;
• C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl;
• R6 and R7 are independently selected from the group consisting of hydrogen, C1-C6-alkyl, and C3-C6-carbocycle;
• or R6 and R7 are taken together with the carbon atom to which they are attached to form a C3-C6-carbocycle or a 3- to 6-membered heterocycle;
• n is 0 or 1;
• W is oxygen or sulfur;
• Y is NR8 wherein R8 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, hydroxy, C1-C6-alkoxy or C3-C6-carbocycle;
• Z is selected from the group consisting of cyano, —C(═O)—ORa, —C(═O)—SRa, —C(═O)—NRbRc, —C(═S)—NRbRc and —C(═O)—NH—CRdRe—C(═O)—ORa, wherein Ra is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-cyanoalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C1-C6-alkyl-Si(C1-C6-alkyl)3, —C1-C6-alkyl-C3-C8-cycloalkyl, 5- to 9-membered heteroaryl and —C1-C6-alkyl-5- to 9-membered heteroaryl, or
• Ra is taken together with R4 and with the atoms to which they are attached to form a 4- to 7-membered heterocycle,
• Rb and Rc are independently selected from the group consisting of hydrogen, C1-C6-alkyl, hydroxyl, C1-C6-alkoxy, cyano, and C1-C6-cyanoalkyl, or
• Rb is taken together with R4 and with the atoms to which they are attached to form a 4- to 7-membered heterocycle,
• Rd and Re are independently selected from the group consisting of hydrogen, cyano, hydroxyl, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, —O—C(═O)—C1-C6-alkyl, C3-C6-carbocycle, —C(═O)—NH2, —C(═O)—NH(C1-C6-alkyl), —C(═O)—N(C1-C6-alkyl)2, —C(═O)—OH, —C(═O)—O—C1-C6-alkyl, aryl, 5- to 9-membered heteroaryl, —C1-C6-alkyl-C1-C6-alkoxy, —C1-C6-alkyl-C3-C6-carbocycle, —C1-C6-alkyl-aryl, —C1-C6-alkyl-hydroxyaryl, —C1-C6-alkyl-5- to 9-membered heteroaryl, —C1-C6-alkyl-S—C1-C6-alkyl, —C1-C6-alkyl-S—C(═O)—C1-C6-alkyl, —C1-C6-alkyl-O—(C═O)—C1-C6-alkyl, —C1-C6-alkyl-C(═O)—NH2, —C1-C6-alkyl-C(═O)—NH(C1-C6-alkyl), —C1-C6-alkyl-C(═O)—N(C1-C6-alkyl)2, —C1-C6-alkyl-C(═O)—OH, —C1-C6-alkyl-C(═O)—O—C1-C6-alkyl, and —C1-C6-alkyl-NH—C(═NH)—NH2, wherein at least one of Rd and Re is hydrogen, C1-C6-alkyl or C3-C6-carbocycle, or
• Rd and Re are taken together with the carbon atom to which they are attached to form a carbonyl, C3-C6-carbocycle, or a 3- to 6-membered heterocycle;
• provided that 3,4,5-trichloro-N-(2-cyanoethyl)-N-cyclohexylthiophene-2-carboxamide [24504-23-2], 3,4,5-trichloro-N,N-bis(2-cyanoethyl)thiophene-2-carboxamide [24467-28-5], and 3,4,5-trichloro-N-(2-cyanoethyl)-N-methylthiophene-2-carboxamide [24417-82-1] are excluded from the compounds of formula (I),
• wherein if W is oxygen, and Y is NR8, and R8 is hydrogen or C1-C6-alkyl, and n=0, and R4 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkyl-aryl, C1-C6-alkyl-hydroxyaryl, and cyclopropyl and R5 is hydrogen or R4 and R5 are taken together with the carbon atom to which they are attached to form a cyclopropyl, then Z is selected from the group consisting of cyano, —C(═O)—SRa, —C(═O)—NRbRc, —C(═S)—NRbRc, and —C(═O)—NH—CRdRe—C(═O)—ORa,
• to the plant or plant parts.